Aqueous seed coating composition

Abstract

An aqueous seed coating composition includes water and a formulation that includes a polymer component including a particular acrylate copolymer and a particular polyurethane that includes the reaction product of a 2,2-hydroxymethyl-substituted carboxylic acid, a component including active hydrogen atoms, and a diisocyanate. The composition is used to coat seeds such that the coated seeds produce minimal dust when transported and / or utilized.

Description

PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PCAQUEOUS SEED COATING COMPOSITIONCROSS-REFERENCE TO RELATED APPLICATION

[0001] This application claims the benefit of U.S. Provisional Application No. 63 / 713,154 filed on October 29, 2024, which is hereby expressly incorporated herein by reference in its entirety.TECHNICAL FIELD

[0002] The present disclosure generally relates to an aqueous seed coating composition. More specifically, this disclosure relates to an aqueous seed coating composition that includes a polymer component including an acrylate copolymer and a polyurethane that reduces dust production when applied to seeds.BACKGROUND

[0003] As seeds are stored, transported and handled in the agricultural industry, motion and vibration can produce a substantial amount of seed dust. When this dust is allowed to escape into the atmosphere, it can disturb the environment. The environmental costs and concerns of dust-off are many. For example, costs may be increased relative to materials intended to remain on the seed but that dust off. Moreover, an amount of product remaining on the seed as it is planted into the soil may not meet the required rate for effectiveness, which could lead to decreased pest resistance.

[0004] During the past 10 years, awareness has developed concerning the potential environmental hazards caused by fugitive seed treatment dust escaping into the surrounding air. Some mechanical stewardship measures, such as adding dust deflectors to planting equipment, have been used with varying levels of success. These deflectors can include baffles and other mechanical elements to reduce dust. However, such options can be too expensive for famers to use in the field.

[0005] As an alternative, seed treatment technologies have been used by farmers as an effective tool to provide the necessary protection of seeds for a strong, healthy start. Using seed treatments delivers a very precise application of chemical and biological treatments that shield seeds from the insects and diseases that exist in the soil during germination and seedling development. For example, these seed treatments can increase germination, protect seeds and seedlings from many seed-bome and soil-borne pathogens, assist in achieving more uniform planting by coating thePCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC seeds to improve flowability, enhance seedling growth, enhance seedling emergence, and enhance crop performance during the growing season.

[0006] Research and development has been completed to develop seed treatment polymers to bind treatments to seeds and reduce the amount of dust off. For example, for crops such as corn, soybeans and cotton, thin film coatings that act like a binder and lock in active ingredients on to the seed to prevent the abrasion and dust-off or rub-off can be used. However, different seeds react differently to treatment. For example, a soybean seed does not act like a corn seed once it is treated with a liquid seed coating. Moreover, many seed treatments are considered plastics and, as such, are subject to microplastic regulations.

[0007] Developing new seed coating technologies to reduce dust-off is an important, ongoing industry. Accordingly, there remains opportunity for improvement. Furthermore, other desirable features and characteristics of the present disclosure will become apparent from the subsequent detailed description of the disclosure and the appended claims, taken in conjunction with the accompanying drawings and this background of the disclosure.BRIEF SUMMARY

[0008] This disclosure provides an aqueous seed coating composition that includes: about 1 to about 80 weight percent of water based on a total weight of the coating composition; and about 1 to about 50 weight percent actives of a formulation based on a total weight of the coating composition, wherein said formulation comprises:A. a polymer component present in an amount of from about 0.5 to about 55 weight percent actives based on a total weight of said coating composition and comprising:(1) an acrylate copolymer present in an amount of from about 20 to about 40 weight percent based on a total weight of the polymer component and comprising the reaction product of(a) butyl acrylate;(b) methyl methacrylate; and(c) methacrylic acid; and(2) a single polyurethane present in an amount of from about 60 to about 80 weight percent based on a total weight of the polymer component and that is the reaction product of:PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC(i) a 2,2-hydroxymethyl-substituted carboxylic acid of the structure:wherein R is a C1-C3 alkyl group,(ii) an active hydrogen containing component, other than the 2,2- hydroxymethyl-substituted carboxylic acid, comprising: a polyalkylene glycol, a polyalkoxylated bisphenol A, an isosorbide, a polyether polyol, a polyester polyol, a poly ether amine; or combinations thereof; and(iii) a diisocyanate;B. a filler present in an amount of from about 0 to about 40 weight percent actives based on a total weight the coating composition;C. a wetting agent present in an amount of from about 0 to about 15 weight percent actives based on a total weight the coating composition;D. a dispersing agent present in an amount of from about 0.1 to about 5 weight percent actives based on a total weight the coating composition.BRIEF DESCRIPTION OF THE DRAWINGS

[0009] The patent or application file contains at least one drawing executed in color. Copies of this patent or patent application publication with color drawing(s) will be provided by the Office upon request and payment of the necessary fee.

[0010] The present disclosure will hereinafter be described in conjunction with the following drawing figures, wherein like numerals denote like elements, and

[0011] FIG. 1 is a line graph of dust rate vs. weight percent of polyurethane in Example 5;

[0012] FIG. 2 is a cross-sectional view of a coated seed including the seed itself and also including a protective layer disposed about an entirety of the seed;PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0013] FIG. 3 is a cross-sectional view of a coated seed including the seed itself and also including a protective layer disposed about at least a portion of the seed; and

[0014] FIG. 4 generally illustrates various thicknesses of the protective layer disposed about at least a portion of the seed at various points.DETAILED DESCRIPTION

[0015] The following detailed description is merely exemplary in nature and is not intended to limit the current aqueous seed coating composition. Furthermore, there is no intention to be bound by any theory presented in the preceding background or the following detailed description.

[0016] Embodiments of the present disclosure are generally directed to aqueous seed coating compositions and methods for forming the same. For the sake of brevity, conventional techniques related to aqueous seed coating composition processing may not be described in detail herein. Moreover, the various tasks and process steps described herein may be incorporated into a more comprehensive procedure or process having additional steps or functionality not described in detail herein. In particular, various steps in the manufacture of aqueous seed coating compositions are well-known and so, in the interest of brevity, many conventional steps will only be mentioned briefly herein or will be omitted entirely without providing the well-known process details.

[0017] In this disclosure, the terminology “about” can describe values ± 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10%, in various embodiments. Moreover, it is contemplated that, in various non-limiting embodiments, it is to be appreciated that all numerical values as provided herein, save for the actual examples, are approximate values with endpoints or particular values intended to be read as “about” or “approximately” the value as recited. It is also contemplated that all isomers and chiral options for each compound described herein are hereby expressly contemplated for use herein in various non-limiting embodiments.

[0018] Throughout this disclosure, the terminology percent "actives" is well recognized in the art and means the percent amount of active or actual compound or molecule present as compared to, for example, a total weight of a diluted solution of a solvent and such a compound. Some compounds, such as a solvent, are not described relative to a percent actives because it is well known to be approximately 100% actives. Any one or more of the values described herein may be alternatively described as percent actives as would be understood by the skilled person.

[0019] In various embodiments, the terminology “free of’ describes embodiments that include less than about 5, 4, 3, 2, 1, 0.5, or 0.1, weight percent (or weight percent actives) of the compoundPCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC or element at issue using an appropriate weight basis as would be understood by one of skill in the art. In other embodiments, the terminology “free of’ describes embodiments that have zero weight percent of the compound or element at issue.

[0020] The terminology “consists essentially of’ may describe various non-limiting embodiments that are free of one or more optional compounds described herein and / or free of one or more polymers, surfactants, additives, solvents, etc.

[0021] It is to be understood that the subscripts of polymers are typically described as average values because the synthesis of polymers typically produces a distribution of various individual molecules.

[0022] The polymers and compositions disclosed herein may suitably comprise, consist of, or consist essentially of the components, elements, and process delineations described herein. The embodiments illustratively disclosed herein suitably may be practiced in the absence of any element which is not specifically disclosed herein.Aqueous Seed Coating Composition

[0023] This disclosure provides an aqueous seed coating composition comprising: about 1 to about 80 weight percent of water based on a total weight of the coating composition; and about 1 to about 50 weight percent actives of a formulation based on a total weight of the coating composition, wherein said formulation comprises:A. a polymer component present in an amount of from about 0.5 to about 55 weight percent actives based on a total weight of said coating composition and comprising:(1) an acrylate copolymer present in an amount of from about 20 to about 40 weight percent based on a total weight of the polymer component and comprising the reaction product of(a) butyl acrylate;(b) methyl methacrylate; and(c) methacrylic acid; and(2) a single polyurethane present in an amount of from about 60 to about 80 weight percent based on a total weight of the polymer component and that is the reaction product of:(i) a 2,2-hydroxymethyl-substituted carboxylic acid of the structure:PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PCwherein R is a C1-C3 alkyl group,(ii) an active hydrogen containing component, other than the 2,2- hydroxymethyl-substituted carboxylic acid, comprising: a polyalkylene glycol, a polyalkoxylated bisphenol A, an isosorbide, a polyether polyol, a polyester polyol, a poly ether amine; or combinations thereof; and(iii) a diisocyanate;B. a filler present in an amount of from about 0 to about 40 weight percent actives based on a total weight the coating composition;C. a wetting agent present in an amount of from about 0.1 to about 15 weight percent actives based on a total weight the coating composition;D. a dispersing agent present in an amount of from about 0.1 to about 5 weight percent actives based on a total weight the coating composition.

[0024] In various embodiments, the coating composition is, includes, consists essentially of, or consists of, the water and the formulation. In other embodiments, the coating composition is, includes, consists essentially of, or consists of, the water and the formulation wherein the formulation itself may be, include, consist essentially of, or consists of, the polymer component, the polyurethane, the filler, the wetting agent, and the dispersing agent. It is also contemplated that a dye and / or a pesticide and / or any one or more additives described herein may be included in one or more of the above embodiments. The terminology “consist essentially of’ describes various embodiments that are free or, or include less than about 1, 0.9, 0.8, 0.7, 0.6, 0.5, 0.4, 0.3, 0.2, 0.1, or 0.05, weight percent actives, based on a total weight of coating composition and / or formulation, of one or more optional additives described herein, one or more pesticides, herbicides, insecticides,PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC fungicides, etc., one or more polymers different from those described herein, one or more polymers described as optional herein, one or more solvents known in the art, one or more polyurethanes known in the art but not required herein, one or more acrylate (co)polymers known in the art but not required herein, one or more surfactants known in the art, one or more fillers, and / or one or more colorants, bio stimulants, nutrients (e.g. micronutrients), growth regulators, defoamers, antifreeze, rheology modifiers, pigments, wetting agents not required herein, dispersing agents not required herein, dyes, hydrogels, binders, antimicrobials, clay minerals, anti-caking agents, adhesives, as known in the art, etc.Water

[0025] Typically, the coating composition is described as an aqueous coating composition. For example, in various embodiments, the coating composition includes about 0.1 to about 80 weight percent of water based on a total weight of the coating composition. This may or may not include amounts of water that are present in various components themselves, e.g. if the polymer component is present in or as its own aqueous solution. In various embodiments, the water is present in an amount of from about 1 to about 80, about 5 to about 75, about 10 to about 70, about 15 to about 65, about 20 to about 60, about 25 to about 55, about 30 to about 50, about 35 to about 45, or about 40 to about 45, weight percent based on a total weight of the coating composition. In various embodiments, the water is present in an amount of from about 5 to about 45, about 10 to about 40, about 15 to about 35, about 20 to about 30, or about 25 to about 30, weight percent based on a total weight of the coating composition. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.Formulation

[0026] The coating composition also includes about 1 to about 50 weight percent actives of a (coating) formulation based on a total weight of the coating composition. Again, one or more components of the formulation may be supplied and / or present as aqueous compositions themselves. In various embodiments, the formulation is present in an amount of from about 5 to about 45, about 10 to about 40, about 15 to about 35, about 20 to about 30, or about 25 to about 30, weight percent actives based on a total weight of the coating composition. In various nonlimiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0027] The formulation may be, include, consist essentially of, or consist of (A) the polymer component, (B) the filler, (C) the wetting agent, (D) the dispersing agent and optionally (E) a dye, and / or (F) an active ingredient. The terminology “consist essentially of’ may be as described above. Each of (A)-(F) is described below in greater detail.Polymer Component

[0028] The polymer component is present in the coating composition in an amount of from about 1 to about 98 weight percent actives based on a total weight of the coating composition. In various embodiments, the polymer component is present in an amount of from about 5 to about 95, about 10 to about 90, about 15 to about 85, about 20 to about 80, about 25 to about 75, about 30 to about 70, about 35 to about 65, about 40 to about 55, or about 45 to about 50, weight percent actives based on a total weight of the coating composition. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0029] The polymer component may be, include, consist essentially of, or consist of the acrylate polymer and the polyurethane. The terminology “consist essentially of’ may be as described above.Acrylate Polymer

[0030] In various embodiments, the acrylate copolymer is present in an amount of from about 20 to about 40, about 25 to about 35, or about 25 to about 30, weight percent actives based on a total weight of the polymer component. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0031] The acrylate copolymer may be, include, consist essentially of, or consist of, the reaction product of : (a) butyl acrylate; (b) methyl methacrylate; and (c) methacrylic acid. The terminology “consist essentially of’ may be as described above.

[0032] The particular weight or molar ratio of reactions (a) : (b) : (c) is not particularly limited and may be, for example about (1-99) : about (1-99) : about (1-99), wherein the terminology “consist essentially of’ may be as described above. In other embodiments, the weight or molar percents of each of (a), (b), and (c) that are reacted to form the acrylate copolymer, such that a total of (a) + (b) + (c) is about 100 percent (either weight or molar), is each independently from about 1 to about 99, about 5 to about 90, about 10 to about 85, about 15 to about 80, about 20 toPCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC about 75, about 25 to about 70, about 30 to about 65, about 35 to about 60, about 40 to about 55, or about 45 to about 50. In other embodiments, one or more of these amounts may be from about 25 to about 50, about 30 to about 45, or about 30 to about 40, weight percent actives. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0033] In various embodiments, the molar or weight percent of (a) is from about 30 to about 50, about 32 to about 48, about 34 to about 46, about 36 to about 44, about 38 to about 42, or about 40. In further embodiments, the molar or weight percent of (b) is from about 38 to about 54, about 40 to about 52, about 42 to about 50, about 44 to about 48, or about 46 to about 48. In other embodiments, the molar or weight percent of (c) is from about 10 to about 20, about 12 to about 18, or about 14 to about 16. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0034] The acrylate copolymer is not particularly limited relative to molecular weight. In various embodiments, the weight average molecular weight (Mw) is from about 5 to about 100, about 10 to about 95, about 15 to about 90, about 20 to about 85, about 25 to about 80, about 30 to about 75, about 35 to about 70, about 40 to about 65, about 45 to about 60, or about 50 to about 55, kDa. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0035] In one embodiment, the acrylate copolymer has a weight average molecular weight of from about 70 to about 100 kDa and is the reaction product of: (a) about 30 to 50 weight percent of the butyl acrylate based on a total weight of the reaction product; (b) about 30 to about 50 weight percent of the methyl methacrylate based on a total weight of the reaction product; and (c) about 5 to about 25 weight percent of the methacrylic acid based on a total weight of the reaction product. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0036] The reaction conditions used to form the acrylate copolymer are not particularly limited and may be chosen by one of skill in the art.PCT PATENT APPLICATION Attorney Docket No.: 364.1538PCPolyurethane

[0037] Referring back, the polyurethane is a single polyurethane. Typically, in various embodiments, this means that only one polyurethane is utilized and a combination of two or more polyurethanes is not utilized. In various embodiments, the single polyurethane is free of one or more additional polyurethanes. Similarly, the coating composition as a whole and / or the formulation may include the single polyurethane and be free of one or more additional polyurethanes. In other embodiments, the coating composition and / or the formulation may be described as free of a mixture, or combination, of two or more polyurethanes. In other embodiments, the terminology “free of’ may describe an amount of any second or additional polyurethane of zero or less than about 10, 9, 8, 7, 6, 5, 4, 3, 2, 1, 0.5, or 0.1, weight percent based on a total weight of the polymer component.

[0038] In various embodiments, the polyurethane is present in an amount of from about 60 to about 80, about 65 to about 75, or about 70 to about 75, weight percent actives based on a total weight of the polymer component. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0039] The polyurethane may be, include, consist essentially of, or consist of, the reaction product of (i) a 2,2-hydroxymethyl-substituted carboxylic acid, (ii) an active hydrogen containing component, other than the 2,2-hydroxymethyl-substituted carboxylic acid, and (iii) a diisocyanate, wherein the terminology “consist essentially of’ may be as described above. Each of (i), (ii), and (iii) are described below. The reaction conditions used to form the polyurethane are not particularly limited and may be chosen by one of skill in the art.

[0040] The polyurethane may be described as a fully reacted carboxylated polymer. The incorporation / use of the 2,2-hydroxymethyl-substituted carboxylic acid introduces pendant carboxylic acid groups into the polymer chain which, after neutralization, renders the polyurethane soluble or dispersible in water or in mixtures of water with other polar solvents. This allows for formation of high solids content compositions with low viscosity.

[0041] In various embodiments, the 2,2-hydroxymethyl-substituted carboxylic acid has the structure:PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PCwherein R is hydrogen or a Ci -C20 alkyl group and wherein the carboxylic acid provides about 0.35 to about 2.25 milliequivalents of carboxyl functionality per gram of polyurethane. In various embodiments, the alkyl group has 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, carbon atoms. In various non-limiting embodiments, all values and ranges thereof, including and between those set forth above are hereby expressly contemplated for use herein.

[0042] Specific examples include 2,2-di(hydroxymethyl)acetic acid, 2,2- di(hydroxymethyl)propionic acid, 2,2-di-(hydroxy-methyl)butyric acid, 2,2- di(hydroxymethyl)pentanoic acid, and the like. In one embodiment, the acid is 2,2-di- (hydroxymethyl)propionic acid. The 2,2-hydroxymethyl-substituted carboxylic acids are typically utilized / present in an amount to give 0.35 to 2.25, typically 0.5 to 1.85, milliequivalents of carboxyl functionality per gram of polyurethane, e.g. about 3 to 30% by weight of the polyurethane. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0043] Referring now to (ii) the active hydrogen containing component, this component includes about 5 to about 90% actives by weight, based on the weight of the polyurethane, of an active hydrogen containing component, other than the 2,2-hydroxymethyl-substituted carboxylic acid. The compound of (ii) typically has at least two active hydrogen atoms (as determined by the Zerewitinoff method). The active hydrogen atoms are usually attached to oxygen, nitrogen or sulfur atoms. This compound may be present / utilized in an amount of about 10 to 90% by weight of the polyurethane, typically in an amount of 15 to 70% by weight and may have a weight average molecular weight of greater or less than about 1000 Da. Typically, this compound is linear so that gelling during polymerization is minimized or prevented. However, small amounts of non-linear components may be used to enhance properties provided use does not cause gelling. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0044] One or more different compounds can be used. Alternatively, such compounds can be combined into one component, e.g. components (A), (B) and (C). For example, this component may include a combination of: a component (A) and a component (B); or (b) a component (C) in combination with component (A) and / or component (B); or component (C), wherein component (A) comprises a polymer having at least two active hydrogen atoms and has a Tg less than about 5° C; wherein component (B) comprises a first active hydrogen containing component comprising an about 5 to about 14-membered ring that is heterocyclic, aliphatic, aromatic, cyclic, alicyclic, and / or spiro, and is substituted with zero to about sixteen alkoxylate units; and wherein component (C) comprises a second active hydrogen containing component comprising an about 5 to about 14- membered ring that is heterocyclic, aliphatic, aromatic, cyclic, alicyclic, and / or spiro, and is substituted with greater than about sixteen alkoxylate units. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0045] In various embodiments, Component (A) is a polymer with at least two active hydrogen atoms having a Tg less than about 5, 0, -5, or -10°C. In various embodiments, component (A) may be, but is not limited to, a poly(alkylene oxide), e.g., a polyethoxylate, a polypropoxylate, a polyethoxylate / propoxylate, polymethylene oxide, polybutylene oxide, poly etherdiols, polyesterdiols, polyolefin diols, poly (meth) acrylate diols, polysiloxanediamines, poly siloxanediols, and / or combinations thereof.

[0046] Component (B) typically includes a cyclic ring structure. For example, component (B) typically is or includes active hydrogen components including at least one 5 to 14-membered ring, wherein the ring may be heterocyclic, aliphatic, aromatic, cyclic, alicyclic, and / or a spiro, ring. Non-limiting examples of such rings include cyclohexyl, cyclopentyl, norbornyl, phenyl, biphenyl, phenyl ether, Bisphenol A, hydrogenated bisphenol A, morpholino, pyrrolidine, piperidine, pyridine, pyrrole, tetrahydropyran, furan, isosorbide, and oxazole rings. In various embodiments, this description includes aromatic diols and their saturated hydrocarbon analogs as disclosed in, for example, U.S. Pat. Nos. 3,477,990 and 3,948,855, each of which are expressly incorporated herein in their entirety in various non-limiting embodiments. The ring(s) of component (B) are typically substituted with zero to about sixteen alkoxylate units. In various embodiments, one or more of the alkoxylate units are ethoxylate, propoxylate, or butoxylate units. Moreover, the total number of each of such units may independently be about 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13,PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC14, 15, or 16, which may be an actual number or an average number. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0047] Referring now to Component (C), this component may be used in place of, or in addition to, the combination of components (A) and (B), in addition to the aforementioned compounds described above. Component (C) may be or include any one or more of the cyclic ring structures described above with respect to component (B), however substituted with greater than about sixteen alkoxylate units, either as actual numbers or as an average. In various embodiments, the maximum number of alkoxylate units is about 20, 25, 30, 35, 40, 45, or 50. In various nonlimiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0048] The ring structures of components (B) and (C) can be substituted with H or with lower alkyl substituents of 1, 2, 3, or 4 carbon atoms. To prevent unwanted side reactions, crosslinking and gelling of the polyurethane, typically there is no acid substitution on the rings. However, substitution is possible.

[0049] In one embodiment, the ring(s) of component (B) is chosen from cyclohexyl, cyclopentyl, norbornyl, phenyl, biphenyl, phenyl ether, Bisphenol A, hydrogenated Bisphenol A, morpholino, pyrrolidine, piperidine, pyridine, pyrrole, tetrahydropyran, furan, isosorbide, and oxazole rings substituted with zero to about sixteen alkoxylate units. In another embodiment, component (B) is chosen from Bisphenol A, hydrogenated bisphenol A, and combinations thereof substituted with zero to about sixteen alkoxylate units.

[0050] In one embodiment, the ring(s) of component (C) is chosen from cyclohexyl, cyclopentyl, norbornyl, phenyl, biphenyl, phenyl ether, Bisphenol A, hydrogenated Bisphenol A, morpholino, pyrrolidine, piperidine, pyridine, pyrrole, tetrahydropyran, furan, isosorbide, and oxazole, rings substituted with zero to about sixteen alkoxylate units. In another embodiment, component (C) is chosen from Bisphenol A, hydrogenated Bisphenol A, and combinations thereof substituted with greater than about sixteen alkoxylate units.

[0051] In various embodiments, various uses and / or combinations of components (A), (B), and / or (C) are contemplated, e.g. (A)+(B); (A)+(C); (B)+(C); (A)+(B)+(C); or (C). Any one or more of the components and / or combinations may be used alone or with one or more others. In various embodiments, each of components (A), (B) and / or (C) may be reacted such that they makePCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC up about 5 to about 90, about 10 to about 85, about 15 to about 80, about 20 to about 75, about 25 to about 70, about 30 to about 65, about 35 to about 60, about 40 to about 55, or about 45 to about 50, weight percent of the final polyurethane. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0052] In various embodiments, the polyurethane will have a Tg value less than about 5, 4, 3, 2, 1, -1. -2, -3, -4, -5, -6, -7, -8, -9, or -10° C, or any range thereof. In various embodiments, the polyurethane is prepared from a major amount of (A) and (B), one or more of which has a weight average molecular weight of greater or less than about 1000 Da. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0053] In preparing the polyurethane, it may be desirable to chain extend the polyurethane using an additional component also having active hydrogen atoms. Typical chain extending agents include, but are not limited to, water, saturated or unsaturated glycols, such as, ethylene glycol, diethylene glycol, triethylene glycol and the like; amino alcohols, such as, ethanolamine, propanolamine, butanolamine, hydroxyaminobutane, and the like; mono- and dialkoxylated aliphatic, cycloaliphatic, aromatic and heterocyclic primary amines, such as, N- methyldiethanolamine, N-oleyl diethanolamine, N-cyclohexyl diisopropanolamine, N,N- dihydroxyethyl-p-toluidine, N,N-dihydroxy-propylnaphthylamine and the like; amines, such as ethylene diamine, diethylene tetramine, triethylenetetramine, piperazine, N-N-bis-gamma- aminopropyl-N-methyl-amine, taurine, silicone diamine, Jeffamines® and the like; ethoxylated polyamines such as Jeffamines® D and T series; carboxylic acids including aliphatic, cycloaliphatic, aromatic and heterocyclic dicarboxylic acids, such as, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, terephthalic acid, 1,5-dicarboxylic naphthalic acid, maleic acid, fumaric acid, diglycolic acid, quinolinic acid, lutidinic acid and the like; amino carboxylic acids, such as, glycine, lysine, aspartic acid, iminodiacetic acid, alpha and beta-alanine, 6-aminocaproic acid, 4-aminobutyric acid, p-aminobenzoic acid, 5 -aminonaphthoic acid and the like; and amino acids such as glucamine, maltoamine and lactamine and the like.

[0054] Chain extenders may also be saccharide amines based on reducing sugars or those composed of glycosyl units connected by glycosidic linkages which are disclosed in U.S. Pat. No. 5,494,602, which is expressly incorporated herein by reference in its entirety in various non-PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC limiting embodiments. In still other embodiments, the chain extenders can be linear or branched, and may be composed of a single type of glycosyl unit or may be composed of two or more different types of glycosyl units. Non-limiting exemplary saccharides according to the present invention include, without limitation, starches, hydrolyzed starches, glucose, galactose, maltose, lactose, maltodextrins, com syrup solids, cellulose, hydrolyzed cellulose, dextran, hydrolyzed dextran, guar gum, hydrolyzed guar gum, locust bean gum and hydrolyzed locust bean gum. Such starches include, for example, corn, potato, tapioca and rice starches. Various saccharides that can be used herein are described in U.S. Pat. No. 5,494,602, which is incorporated herein by reference in its entirety in various non-limiting embodiments.

[0055] The polyurethane may also be chain terminated. Typical chain terminating agents include ethanol, isopropanol, taurine, and the like. Also included are amino acids such as glucamine, maltamine, lactamine and the like.

[0056] Referring now to the (iii) diisocyanate, this compound may be singular or may include more than one compound. For example, this compound may include organic polyisocyanates or mixtures of polyisocyanates which may be or include aliphatic and / or aromatic polyisocyanates, and / or combinations thereof. Use of polyisocyanates, such as diisocyanates, tend to produce a linear polyurethane although minor amounts of trifunctional isocyanates may be used in conjunction with the diisocyanates. In this disclosure, the diisocyanate is utilized in a sufficient amount to react with the aforementioned compounds, excepting the hydrogen on the carboxylate of the 2,2-hydroxymethyl-substituted carboxylic acid, which is understood by the skilled person. This amount of the (iii) diisocyanate will vary depending on the amounts of the reacting components that are utilized.

[0057] Non-limiting exemplary diisocyanates include, but are not limited to, methylene di-p- phenyl diisocyanate, methylene-bis(4-cyclohexylisocyanate), isophorone diisocyanate, toluene diisocyanate, 1,5-naphthalene diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,2'-dimethyl- 4,4'-diphenylmethane diisocyanate, 4,4'-dibenzyldiisocyanate, 1,3-phenylene diisocyanate, 1,4- phenylene diisocyanate, mixtures of 2,4- and 2,6-toluene diisocyanate, 2,2'-dichloro-4,4'- diisocyanato diphenylmethane, 2,4-dibromo-l,5-diisocyanato naphthalene, butane- 1,4- diisocyanate, hexane- 1,6-diisocyanate, cyclohexane- 1,4-diisocyanate, bis(l-isocyanato-l- mcthylcthylj-bcnzcnc, trimethylhexamethylenediisocyanate, and combinations thereof. In one embodiment, the (iii) diisocyanate is chosen from methylene-di-p-phenyl diisocyanate, methylene-PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC bis-(4-cyclohexylisocyanate), isophorone diisocyanate, toluene diisocyanate, and combinations thereof.

[0058] If it is desired not to chain extend the polyurethane, the reaction of the diisocyanate can be quenched by the addition of a monofunctional active hydrogen-including component to consume any residual isocyanate functionality. Examples of these quenching components are well known in the art and include, but are not limited to, monofunctional alcohols, monofunctional amines, monofunctional low molecular weight polymers, and combinations thereof. A typical quenching component is ethanol.

[0059] In various embodiments, the active hydrogen containing component, other than the 2,2- hydroxymethyl-substituted carboxylic acid, is chosen from a polyalkylene glycol, a polyalkoxylated bisphenol A, an isosorbide, a polyether polyol, a polyester polyol, a polyether amine, and combinations thereof. Any of these may be any known in the art.

[0060] In one embodiment, the poly alkylene glycol is chosen from polyethylene glycol (PEG), polypropylene glycol (PPG), polytetramethylene ether glycol (PTMEG), and combinations thereof. For example, the polyalkylene glycol may be chosen from low molecular weight (Mw < 1,000 Da) compounds such as PEG 200, PEG 400, and PEG 600; medium molecular weight (Mw 1,000 - 10,000 Da) compounds such as PEG 1,000, PEG 3,350 and PEG 8,000; high molecular weight (Mw > 10,000 Da) compounds such as PEG 12,000, PEG 20,000, PEG 35,000, PEG 100,000, and combinations thereof. For example, the polyalkylene glycol may be chosen from low molecular weight (Mw < 1,000 Da) compounds such as PPG 200 and PPG 400; medium molecular weight (Mw 1,000 - 4,000 Da) compounds such as PPG 1,000, PPG 2,000, and PPG 4,000; high molecular weight (Mw > 4,000 Da) compounds such as PPG 6,000 and PPG 10,000, and combinations thereof. For example, the polyalkylene glycol may be chosen from low molecular weight (Mw < 1,000 Da) compounds such as PTMG 250 and PTMG 650; medium molecular weight (Mw 1,000 - 2,000 Da) compounds such as PTMG 1,000, PTMG 1,400, and PTMG 2,000; high molecular weight (Mw > 2,000 Da) compounds such as PTMG 2,900 and PTMG 3,400, and combinations thereof.

[0061] In other embodiments, the polyalkoxylated bisphenol A may be chosen from ethoxylated bisphenol A compounds such as bisphenol A ethoxylate (1-2 moles EO), bisphenol A ethoxylate (4-5 moles EO), and bisphenol A ethoxylate (10-15 moles EO); propoxylated bisphenol A compounds such as bisphenol A propoxylate (1-2 moles PO), bisphenol A propoxylate (4-5PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC moles PO), and bisphenol A propoxylate (10-15 moles PO); ethoxylated / propoxylated bisphenol A compounds with varying ratios of ethylene oxide and propylene oxide, and combinations thereof.

[0062] In other embodiments, the isosorbide may be chosen from pure isosorbide; isosorbide diesters formed with acids like adipic acid and succinic acid; ethoxylated isosorbide compounds such as isosorbide monoethoxylate and isosorbide diethoxylate; propoxylated isosorbide compounds such as isosorbide monopropoxylate and isosorbide dipropoxylate; ethoxylated / propoxylated isosorbides, or specialized derivatives like isosorbide dimethyl ether (IDME), and combinations thereof. The isosorbide may be alkoxylated, e.g. propoxylated and / or ethoxylated. In various embodiments, the number of moles of EO and / or PO may be independently be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10... up to about 50. In various embodiments, the number of moles of EO and / or PO may be about 1 to about 50, about 5 to about 45, about 10 to about 40, about 15 to about 35, about 20 to about 30, or about 25 to about 30. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0063] Relative to polyether polyols, any can be used herein. For example, the production of the polyether polyols can be carried out according to known methods, e.g. by base-catalyzed polyaddition of an alkylene oxide to an active hydrogen atom-containing polyfunctional starting compound (e.g. alcohol or amine). The following may be mentioned as examples: ethylene glycol, diethylene glycol, 1,2-propylene glycol, 1,4-butanediol, hexamethylene glycol, bisphenol A, trimethylolpropane, glycerol, pentaerythritol, sorbitol, candy sugar, degraded starch, water, methylamine, ethylamine, propylamine, butylamine, aniline, benzylamine, o- and p-toluidine, a, P-naphthylamine, ammonia, ethylenediamine, propylenediamine, 1,4-butylenediamine, 1, 2-, 1,3- , 1,4-, 1,5- and / or 1,6-hexamethylenediamine, o-, m- and p-phenylenediamine, 2,4-, 2,6-toluylene diene Amines, 2,2'-, 2,4- and 4,4'-diaminodiphenyl meta And di-ethylene diamine. As alkylene oxide, preferably ethylene oxide, propylene oxide, butylene oxide and mixtures thereof are used. The extension of the polyether chain by alkoxylation can be carried out statistically or in a blocklike manner using not only one monomer epoxide but also two or three different monomer epoxides.

[0064] Relative to polyester polyols, any can be used herein. For example, polyester polyols can be produced by polycondensation of polyfunctional carboxylic acids or their derivatives (e.g.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC acid chlorides or anhydrides) with polyfunctional hydroxyl compounds. As polyfunctional carboxylic acids, for example, the following can be used: adipic acid, phthalic acid, isophthalic acid, terephthalic acid, oxalic acid, succinic acid, glutaric acid, azelaic acid, sebacic acid, fumaric acid or maleic acid. As polyfunctional hydroxyl compounds, for example, the following may be used: ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, dipropylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, 1,12-dodecanediol, neopentyl glycol, trimethylolpropane, triethylolpropane or glycerol. Furthermore, the polyester polyol can also be produced by ring-opening polymerization of a lactone (e.g. caprolactone) with a starting diol and / or triol.

[0065] Relative to the polyether amine, any type in the art may be used. For example, the polyether amine may be chosen from monoamine compounds such as JEFF AMINE® M-600, JEFF AMINE® M-1000, and JEFF AMINE® M-2005; diamine compounds such as JEFF AMINE® D-230, JEFF AMINE® D-400, and JEFF AMINE® D-2000, as well as Baxxodur® EC 301 and Baxxodur® EC 302; triamine compounds such as JEFFAMINE® T-403 and JEFF AMINE® T-3000; and other polyether amines such as Versalink® P-650, Versalink® P- 1000, Versalink® P-2000, DEXIN® PEA D230, DEXIN® PEA D400, DEXIN® PEA T403, and combinations thereof. In one embodiment, the polyether amine has the formula H2N- (CHCH3CH2O)y(CH2CH2O)z-CH3, wherein each of y and z is independently 1 to 20, 2 to 19, 3 to 18, 4 to 17, 5 to 16, 6 to 15, 7 to 14, 8 to 13, 9 to 12, 10 to 11, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 12, 13, 14, 15, 16, 17, 18, 29, or 20. In another embodiment, the polyether amine has the formula H2N- (CHCH3CH2O)i9(CH2CH2O)3-CH3. In various non-limiting embodiments, all values and ranges thereof including and between those set forth above are hereby expressly contemplated for use herein.

[0066] Reaction of the aforementioned compounds, i.e., a urethane polymerization reaction, is typically carried out in a reaction medium with or without typical urethane reaction catalysts known in the art. Suitable catalysts include, but are not limited to, dibutyl tin dilaurate; the stannous salts of carboxylic acids having from 2 to 18 carbon atoms, such as stannous laurate, stannous stearate, stannous acetate, stannous butyrate, stannous octoate and the like, and combinations thereof. Other suitable catalysts include dibutyl tin oxide, dibutyl tin sulfide, lead resinate, lead benzoate, lead salicylate, lead 2-ethyl hexoate, lead oleate, iron acetyl acetonate, cobalt benzoate, tetra (2-ethyl hexyl) titanate, tetra butyl titanate, and the like. Those skilled in the art will choosePCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC a specific catalyst to confer desired characteristics to individual urethane reactions. In addition, any suitable tertiary amine may be used alone or with a metallic catalyst, for example, triethylene diamine, N-ethyl morpholine, N-methyl morpholine, or 4-dimethyl amino ethyl piperazine, triethylamine, diazabicyclooctane.

[0067] Typically, polyurethane polymerization is carried out according to techniques known in the art. With respect to the proportion of reactants, the reactants can be selected so that the molar ratio of the isocyanate groups to active hydrogen atoms is between 0.5:1 and 2:1, also referred to herein as a isocyanate / hydroxyl ratio. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0068] Polymerizations reactions may be either solvent-free or may be carried out in the presence of solvent. In addition, polymerization reactions may be carried out in the presence of surfactant or may be surfactant free. In systems where a solvent is use, techniques commonly known in the art may be used to remove the solvent, e.g. steam distillation, vacuum stripping.

[0069] In various embodiments, the polyurethane can be neutralized or non-neutralized. Typical levels of neutralization are greater than 30%, and in some cases greater than a stoichiometric amount of neutralant may be used depending on the acidity of the polymer. The typical bases are sodium hydroxide, potassium hydroxide, 2-amino-2-methyl-l -propanol, hydroxyaminobutanes such as 3-amino-2-methyl-l -propanol, histidine, tris(hydroxymethyl)aminomethane, triisopropanolamine, stearamine, triethanolamine and triethylamine. In various embodiments, the polyurethane may be as described in one or both of US 5,968,494 and / or US 6,291,580, each of which is expressly incorporated by reference in its entirety in various non-limiting embodiments.

[0070] In one embodiment, an isosorbide and / or an alkoxylated isosorbide may be used. For example, the molar composition of such a polyurethane may be about: 20-30 mol% DMPA; 1 to 5 mol% PPG; 15 to 25 mol% isosorbide; and 45 to 55 mol% IPDI. In other embodiments, the molar composition of such a polyurethane may be about 20 to 30 mol% DMPA; 5 to 10 mol% PPG; 15 to 20 mol% propoxylated isosorbide; and 45 to 55 mol% IPDI. In still other embodiments, the polyurethane may be formed using an aromatic polyester polyol from diethylene glycol and phthalic anhydride (Stepanpol PD-320) wherein the molar composition of such a polyurethane may be about 20 to about 30 mol% DMPA; 1 to 10 mol% PPG; 15 to 25 mol% polyester polyol;PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC and 45 to 55 mol% IPDI. Moreover, any one or more of the above components may be substituted for any one or more other components described herein. In various embodiments, one or more of the above values may be about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10...up to about 55. In other embodiments, one or more of the above values may be about 1 to about 55, about 5 to about 50, about 10 to about 45, about 15 to about 40, about 20 to about 35, or about 25 to about 30. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0071] As first described above, the formulation also includes (B) the optional filler, (C) the optional wetting agent, and (D) the dispersing agent.Filler

[0072] The filler is optional such that the coating composition and / or the formulation may include, or be free of, the filler. In various embodiments, the filler is present in an amount of from about 0 to about 50, about 1 to about 50, about 5 to about 45, about 10 to about 40, about 15 to about 30, or about 20 to about 25, weight percent actives based on a total weight the coating composition. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0073] The filler is not particularly limited and may be chosen by one of skill in the art. In one embodiment, the filler is quartz. In various embodiments, the filler can be chosen from quartz, talc, clay, limestone, silica, diatomaceous earth, calcium carbonate, starch, vermiculite, gypsum, perlite, and combinations thereof.Wetting Agent

[0074] The wetting agent is optional such that the coating composition and / or the formulation may include, or be free of, the wetting agent. In various embodiments, the wetting agent is present in an amount of from about 0 to about 10, about 0.1 to about 10, about 0.5 to about 9.5, about 1 to about 9, about 1.5 to about 8.5, about 2 to about 8, about 2.5 to about 7.5, about 3 to about 7, about 3.5 to about 6.5, about 4 to about 6, about 4.5 to about 5.5, or about 5 to about 5.5, weight percent actives based on a total weight the coating composition. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0075] The wetting agent is not particularly limited and may be any known in the art. In one embodiment, the wetting agent is naphthalene sulfonate and / or an alkyl naphthalene sulfonate blend. In various embodiments, the wetting agent may be alternatively described as a surfactant, polyacrylamide, glycerol, lecithin, polysorbate, sodium lauryl sulfate, fatty alcohol ethoxylate, silicone-based agent, alkylphenol ethoxylate, block copolymer, or combinations thereof.Dispersing Agent

[0076] The dispersing agent is present in an amount of from about 0.1 to about 10, about 0.5 to about 9.5, about 1 to about 9, about 1.5 to about 8.5, about 2 to about 8, about 2.5 to about 7.5, about 3 to about 7, about 3.5 to about 6.5, about 4 to about 6, about 4.5 to about 5.5, or about 5 to about 5.5, weight percent actives based on a total weight the coating composition. In various nonlimiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0077] The dispersing agent is not particularly limited and may be any known in the art. In one embodiment, the dispersing agent is an alkoxylated phosphate ester. In various embodiments, the dispersing agent may be alternatively described as a lignosulfonate, polyacrylate, sulfonated naphthalene formaldehyde, polyphosphate, ammonium polyacrylate, sodium hexametaphosphate, sodium lignin sulfonate, alkylbenzene sulfonate, polycarboxylate, modified polyurethane, or combinations thereof.Dye

[0078] The formulation may also include the (E) dye and / or pigment as first introduced above. While for formulation a dye or pigment is not obligatory, it may be used to distinguish treated seeds from non-treated seeds. The dye and / or pigment may be present in an amount of from about 1 to about 25, about 5 to about 25, about 10 to about 20, or about 15 to about 20, weight percent actives based on a total weight of the coating composition. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0079] The dye and / or pigment is not particularly limited and may be any known in the art. For example, the dye and / or pigment may be chosen from titanium dioxide, iron oxide, carbon black, phthalocyanine blue, phthalocyanine green, azo dyes, anthraquinone dyes, ultramarine blue, dioxazine violet, quinacridone red, and combinations thereof.PCT PATENT APPLICATION Attorney Docket No.: 364.1538PCActive Ingredient

[0080] The formulation may also include the (F) active ingredient as first introduced above. The active ingredient may be present in an amount of from about 1 to 60, about 1 to about 55, about 1 to about 50, about 1 to about 45, about 1 to about 40, about 1 to about 35, about 1 to about 30, about 1 to about 25, about 1 to about 20, about 1 to about 15, about 5 to about 55, about 10 to about 50, about 15 to about 45, about 20 to about 40, about 25 to about 35, about 25 to about 30, about 1 to about 10, about 2 to about 9, about 3 to about 8, about 4 to about 7, or about 5 to about 6, weight percent actives based on a total weight of the coating composition. In various nonlimiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0081] The active ingredient is not particularly limited and may be further defined as a pesticide, e.g. a herbicide, insecticide, fungicide, etc. or combinations thereof. In various embodiments, the active ingredient is chosen from imidacloprid, tebuconazole, fludioxonil, metalaxyl-M, and combinations thereof.

[0082] In various embodiments, the active ingredient is chosen from insecticides, fungicides, nematicides and / or other pesticides such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, and / or abamectin. In other embodiments, the active ingredient is chosen from one or more insecticides, fungicides, nematicides and / or other pesticides comprises acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, and / or abamectin. In further embodiments, the active ingredient is chosen from alpha-cypermethrin, beta-cyfluthrin, beta-cypermethrin, bifenthrin, bioresmethrin, cycloprothrin, cyfluthrin, cypermethrin, deltamethrin, esfenvalerate, fenpropathrin, fenvalerate, flucythrinate, gamma cyhalothrin, lambda cyhalothrin, permethrin, phenothrin (and isomers thereof), resmethrin, tau-fluvalinate, tefluthrin, tralomethrin, zeta-cypermethrin, and ZXI-8901. In further embodiments, the active ingredient is chosen from thiamethoxam, fipronil, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, and thiacloprid. In still other embodiments, the active ingredient is chosen from Benomyl (also known as Benlate), Bitertanol, Captan, Carbendazim, Carboxin (also known as Carbathiin), Capropamid, Cymoxanil, Cyprodinil, Difenoconazole, Ethirimol, Fenpiclonil, Fenpropimorph, Fludioxonil, Fluquinconazole, Flutolanil, Flutriafol, Fosetyl- aluminum, Fuberidazole, Guazatine, Hymexanol, Kasugamycin, Imazalil, Imibenconazole, Iminoctadine-triacetate, Ipconazole, Iprodione, Mancozeb, Maneb,PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PCMepronil, Metalaxyl, Metalaxyl-M (Mefenoxam), Metconazole, Metiram, MON 65500, Myclobutanil, Nuarimol, Oxadixyl, Oxine-copper, Oxolinic acid, Pefurazoate, Pencycuron, Prochloraz, Propamocarb hydrochloride, Pyroquilon, Quintozene (also known as PCNB), Silthiopham, Tebuconazole, Tecnazene, Telraconazole, Thiabendazole, Thifluzamide, Thiophenate-methyl, Thiram, Tolclofos- methyl, Triadimenol, Triazoxide, Triflumizole and Triticonazole. In other embodiments, the active ingredient is chosen from azoxystrobin, thiram, chlorothalonil, carboxin, metalaxyl, mefenoxam, and fludioxonil. In still further embodiments, the active ingredient is chosen from pesticides, nematicides, fungicides, inoculants, bio stimulants, biologically active compounds, fertilizers, micronutrients, and combinations thereof. In further embodiments, the active ingredient is chosen from imidacloprid, tebuconazole, and combinations thereof.

[0083] It is contemplated that the active ingredient may also, or alternatively, be utilized independently from the coating composition. For example, the active ingredient may be utilized or applied as part of the coating composition, separately from the coating composition, or both.Other Additives

[0084] The coating composition and / or the formulation may also include, or be free of, any one or more additives such as one or more polymers different from those described herein, one or more surfactants known in the art, one or more fillers, and / or one or more colorants, bio stimulants, biocides, nutrients (e.g. micronutrients), growth regulators, defoamers, antifreeze, rheology modifiers, pigments, wetting agents not required herein, dispersing agents not required herein, dyes, hydrogels, binders, antimicrobials, clay minerals, anti-caking agents, adhesives, as known in the art, etc. Any of these may be as known in the art and used in amounts selected by one of skill in the art.Coated Seed and System for Coating Seeds

[0085] This disclosure also provides a coated seed 20 and a system for coating seeds 22, wherein the system includes a seed 22 and the aforementioned coating composition. The seed 22 is not particularly limited and may be any known in the art. For example, the seed 22 may be a monocotyledonous seed or a dicotyledonous seed or a combination thereof. In various embodiments, the seed 22 is a sunflower seed. In other embodiments, the seed is a com, soybean, vegetable, cereal, cotton, rice or canola, seed 22. The seed 22 may alternatively be described as any type of agricultural seed 22. In various embodiments, the seed 22 is chosen from corn, wheat,PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC soybean, canola, sunflower, alfalfa, edible beans, grains sorghum, turf, forage grass, peas, and combinations thereof. In other embodiments, the seed 22 is chosen from corn seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugarbeet seed, rice, sunflower seed, lettuce seed, and spinach seed, and combinations thereof. In other embodiments, the seed 22 is chosen from com, wheat, barley, oat, rye, spelt, vegetable, soybean, rape seeds, and combinations thereof. In other embodiments, the seed 22 is chosen from rice seed, wheat seed, soybean seeds, corn seeds, and combinations thereof. In still other embodiments, the seed 22 is chosen from corn, wheat, rye, soybean, canola, sunflower, alfalfa, edible beans, barley, oat, spelt, and combinations thereof. In various embodiments, the seed 22 is chosen from corn; Oilseed rape; sugar beet; sunflower; cereals; carrots, endives; onions; sweet com; green and seeded beans; vegetable peas; cotton; and combinations thereof.

[0086] As shown in the Figures, the coated seed 20 includes the seed 22 itself and a protective layer 24 disposed about at least a portion of the seed and including the formulation of this disclosure. For example, the coating composition can be used to coat the seed 22 such that formulation that is part of the coating composition can form the protective layer 24, e.g. upon optional removal of part or all of the water. It is to be understood that the terminology “disposed about” encompasses both partial and complete covering of the seed by the protective layer 24. In one embodiment, the protective layer 24 completely encompasses the seed 22, as set forth in FIG. 2. In another embodiment, the protective layer 24 only partially encompasses the seed 22, as set forth in FIG. 3. Typically, the protective layer 24 is disposed on and in direct contact with the seed 22. Also, the protective layer 24 is typically an outermost layer of the encapsulated seed 20.

[0087] The protective layer 24 can improve the physical properties of the seed 22. For example, the protective layer 24 may preserve the integrity of the seed 22 when sold, and minimizes dust when transported and used. Furthermore, the protective layer 24 can provide an excellent finish and appearance to the seed 22. Even further, the polymers of the protective layer 24 are generally not subject to microplastic regulations thereby decreasing costs and increasing ease of use.

[0088] In various embodiments, the protective layer 24 is typically present in an amount of from 0.1 to 20, more typically in an amount of from 1 to 15, still more typically in an amount of from 3 to 15, and even more typically present in an amount of from 3 to 5, parts by weight per 100 parts by weight of the seed 22. In various embodiments, the protective layer 24 is present in anPCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC amount of from 3 to 6, from 3 to 7, from 3 to 8, from 3 to 9, from 3 to 10, from 3 to 11, from 3 to 12, from 3 to 13, from 3 to 14, from 9 to 12, or from 9 to 15, parts by weight per 100 parts by weight of the seed 22. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0089] The protective layer 24 may have any thickness. The protective layer 24 may have varying thicknesses at differing points of the seed 22, e.g. at various points A-H as shown in FIG. 4. Alternatively, the protective layer 24 may have a uniform thickness at one or more points of the seed 22 or at all or almost all points of the seed 22. Alternatively, the protective layer 24 may be uniform at some points and vary in thickness at other points of the seed 22. This disclosure is not limited by the aforementioned thicknesses as the protective layer 24 may have any thickness. Also, the protective layer 24 is not limited to the thicknesses described above as specifically related to the approximate weight percentages. Said differently, the protective layer 24 may have one or more of the aforementioned thicknesses, or any thickness at all, at any one or more of the aforementioned approximate weight percentages or at different weight percentages than those described above.Dust-Off Minimization

[0090] In various embodiments, the coated seed 20 produces or includes less than about 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1, g / dust per 100 kg / seed. In other embodiments, the coated seed 20 produces or includes less than 14.5, 13.5, 12.5, 11.5, 10.5, 9.8, 8.5, 7.5, 6.5, 5.5, 4.5, 3.5, 2.5, or 1.5, g / dust per 100 kg / seed. In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0091] In still further embodiments, the coated seed 20 produces less than the following approximate amounts of dust, per seed type:Corn: < 0.75g of dust / 100000 seeds;Oilseed rape: < 0.50g of dust / 700 000 seeds;Sugar beet: < 0.25g of dust / 100 000 seed pellets;Sunflower: < 0.40g of dust / 75 000 seeds;Cereals: < 4 g of dust / 100 kg;Carrots, endives: < 0.1 g of dust / 100000 seeds;PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PCOnions: < 0.2 g of dust / 100 000 seeds;Sweet corn: < 0.75 g of dust / 100000 seeds;Green and seeded beans: < 0.4 g of dust / 100000 seeds;Vegetable peas: < 0.2 g of dust / 100000 seeds; and / orCotton: < 6 g of dust / 100 kg.In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0092] The method used to determine the amount of dust (such as any amount described above) may be described as the European Seed Association Heubach Test method, more specifically titled “Assessment of free floating dust and abrasion particles of treated seeds as a parameter of the quality of treated seeds” Authors: ESA STAT Dust Working Group; Version: 1.0 (or 1.1) Date: 23.03.2011; © ESA European Seed Association aisbl.Method of Coating Seeds

[0093] This disclosure also provides a method of coating seeds. The method includes the step of providing the seed and the step of coating at least a portion of the seed with the protective layer including the formulation. The seed may be coated using any method known in the art.

[0094] Seed coating methods vary in complexity depending on the purpose of the coating, the size of the seed, and the specific additives being applied.

[0095] In one embodiment, a film coating method is used. This method applies a thin, uniform layer of the coating composition over the surface of the seed, without significantly altering its size or shape. The process is often used for precision planting. In such a method, seeds are tumbled in a rotating drum or coating pan. The coating composition is then sprayed onto the seeds as they rotate. The tumbling ensures that the coating composition is evenly distributed across the seed surface. Warm air is often introduced to dry the coating composition quickly, ensuring it adheres properly and forms a smooth layer.

[0096] In another embodiment, an encrusting method is used which builds up layers around the seed, increasing its size and weight. This method is typically used for small, lightweight seeds that are difficult to handle or plant individually. In this method, seeds are placed in a rotating drum or fluidized bed system. The coating composition may be applied, followed by the addition of powdered materials such as fillers (e.g., talc, clay, or diatomaceous earth) and active ingredients (nutrients, pesticides, etc.). Layers are built up gradually, and drying occurs intermittently toPCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC solidify the coating. The encrusting continues until the desired size, weight, and shape are achieved. Once coated, the seeds are typically polished for smoother texture.

[0097] In another embodiment, a pelleting method is used which involves surrounding the seed with a thick layer of the coating composition to create a uniform size and shape, often resulting in a spherical or rounded pellet. This method is especially useful for small or irregularly shaped seeds. In this process, seeds are placed in a rotary drum or fluidized bed system. The coating composition may then be applied. Layers of powdered material (e.g., clay, limestone, or other fillers) can then be added gradually, building up to the desired size and weight. The pellet is then dried and hardened to ensure durability. Pellets may also be coated with nutrients, pesticides, or other beneficial substances.

[0098] In another embodiments, a fluidized bed coating method is used which involves suspending seeds in an air stream to coat them uniformly. It is often used for more sophisticated coatings where precision is required. More specifically, seeds are placed in a chamber where they are suspended and agitated by an upward flow of air. The coating composition is sprayed onto the seeds while they are airborne. The seeds are coated uniformly as they move within the fluidized air bed. Drying air is introduced to remove moisture and solidify the coating.

[0099] In another embodiment, a centrifugal coating (e.g. pan coating) method is used which utilizes centrifugal force to apply coatings to seeds, commonly used for encrusting or pelleting. In this process, seeds are placed in a rotating chamber or pan. The coating composition and optional powdered additives are sequentially applied. The rotation of the chamber creates centrifugal force, which helps to evenly distribute the coating compositions over the seeds. The seeds are dried during or after the coating process to ensure that the layers adhere properly.

[0100] In another embodiment, a slurry coating method is used wherein seeds are mixed with a slurry containing the coating composition, and other ingredients. This method is often used for applying liquid-based coatings, such as nutrients or pesticides, and is less focused on changing the size of the seed. More specifically, seeds are tumbled in a mixing chamber. A slurry is poured onto the seeds. The seeds are stirred or tumbled to ensure an even coating. Drying occurs either by airflow or through heat application.

[0101] In another embodiment, an electrostatic coating method is used which uses electrostatic charges to apply the coating composition to the seeds. It is relatively new and less common but can provide high precision in the application. More specifically, seeds are charged with anPCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC opposite electrical charge to the coating composition. The coating composition is applied, and it adheres to the seeds due to electrostatic attraction. Seeds are tumbled to ensure uniform distribution. The coating composition is then fixed through heat or air drying.Additional Embodiments

[0102] In additional embodiments, this disclosure also provides coating compositions as follows, wherein each value is approximate or “about”:In various non-limiting embodiments, all values and ranges thereof, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein. It is also contemplated that these values may vary by ±5%, ±10%, ±15%, ±20%, ±25%, ±30%, etc.

[0103] In additional embodiments, this disclosure also provides coating compositions as follows, wherein each value is approximate or “about”:Coating Composition 1:30 to 40 wt% water;0.05 to 0.2 wt% actives defoamer (e.g. a silicone defoamer);0.1 to 0.3 wt% actives biocide (e.g. bronopol and CMIT / MIT chemistry)20 to 30 wt % actives of the polymer component;10 to 20 wt % actives pigment;1 to 5 wt % actives dispersing agent (e.g. alkoxylated phosphate ester);0.05 to 5 wt% actives xanthan gum; and20 to 30 wt% actives filler (e.g. quartz).PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PCIn various embodiments, it is contemplated that one or more of the aforementioned values may be any value or range of values, both whole and fractional, within the aforementioned ranges and / or may vary by ±5%, ±10%, ±15%, ±20%, ±25%, ±30%, etc.Coating Composition 2:30 to 40 wt% water;0.05 to 0.2 wt% actives defoamer (e.g. a silicone defoamer);0.5 to 5 wt% actives fungicides (e.g. Fludioxanile and / or Metalaxyl-M)5 to 15 wt % actives of the polymer component;10 to 20 wt % actives pigment;1 to 5 wt % actives dispersing agent (e.g. alkoxylated phosphate ester);0.05 to 5 wt% actives xanthan gum; and20 to 30 wt% actives filler (e.g. quartz).In various embodiments, it is contemplated that one or more of the aforementioned values may be any value or range of values, both whole and fractional, within the aforementioned ranges and / or may vary by ±5%, ±10%, ±15%, ±20%, ±25%, ±30%, etc.EXAMPLES

[0104] A series of coated seeds are created and evaluated for dust-off values as shown below.Example 1

[0105] In a first experiment, treated soybean seeds are evaluated. A first group of seeds is coated with a commercial benchmark. A second group of seeds is coated with an aqueous seed coating composition according to this disclosure (Coating 1). The seeds are coated using the following procedure:1. 500 g of seeds are conditioned in conditions of about 50 % relative humidity and about 25 °C for a minimum of 18 hours. The seeds are poured into an automatic coating machine (Concept ML200, Satec) and exposed to about 6- 6.5 ml of the coating composition, injected by automatic pipette. Drum rotation is set to 4500 rpm and spreading disk rotation to 5000 rpm. The seeds are removed 2 min after injection of the coating composition.2. After coating, the seeds are again subjected to conditions of about 50 % relative humidity and 25 °C for a minimum of 18 hours. This forms the coated seeds.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC3. 475g of the coated seeds are then placed in the drum of Heubach dustmeter type1 and subjected to the dusting evaluation that is described in greater detail below.

[0106] The dust-off evaluation is carried out pursuant to the European Seed Association Heubach Test method, more specifically titled “Assessment of free floating dust and abrasion particles of treated seeds as a parameter of the quality of treated seeds” Authors: ESA STAT Dust Working Group; Version: 1.0 Date: 23.03.2011; © ESA European Seed Association aisbl, which is hereby expressly incorporated herein by reference. An average of two measurements is reported below:

[0107] The Commercial Benchmark 1 is a polyvinyl acetate copolymer dispersion that is commercially available from Cheminova Deutschland GmbH & Co. Kg under the tradename of FKL XL.

[0108] The Coating 1 includes the following:PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0109] The Alkoxylated Phosphate Ester is as is described in at least US Pat. No. 11,632,952, which is expressly incorporated herein by reference in its entirety in various non-limiting embodiments.

[0110] The Polymer Component 1 is a mixture of:(1) an acrylate copolymer present in 30 weight percent based on a total weight of the polymer component and comprising the reaction product of:(a) butyl acrylate;(b) methyl methacrylate; and(c) methacrylic acid; in a molar ratio of about [(35-40):(45-50):(15-20)]; and(2) a single polyurethane present in 70 weight percent based on a total weight of the polymer component and that is the reaction product of:(i) a 2,2-hydroxymethyl-substituted carboxylic acid of the structure:wherein R is methyl,(ii) polypropylene glycol having a Mw of about lOOOg / mol; bisphenol A alkoxylated with 1 mole of ethylene oxide and2 moles of propylene oxide on each flank;H2N-(CHCH3CH2O) i9(CH2CH2O)3-CH3; and(iii) IPDI

[0111] The data set forth above shows dusting performance that is comparable to the market benchmark polyvinyl acetate copolymer and does so while not be considered a microplastic andPCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC thus not subject to microplastic regulations. Thus, the aqueous seed coating composition of this disclosure is superior to the commercial benchmark. Moreover, for crops such as com, soybeans and cotton, thin film coatings that act like a binder and lock in active ingredients on to the seed to prevent the abrasion and dust-off or rub-off can be used. However, different seeds react differently to treatment. For example, soybean seeds are sensitive to water during coating. However, the aqueous seed coating composition according to this disclosure still has a positive effect on dusting performance of the binder, which is unexpected to those of skill in the art.Example 2

[0112] In a second experiment, treated corn seeds are evaluated. A third group of seeds is coated with a commercial benchmark. A fourth group of seeds is coated with an aqueous seed coating composition according to this disclosure (Coating 2). After formation, the seeds are evaluated to determine dust-off using the aforementioned method wherein an average of two measurements is reported below:

[0113] The Commercial Benchmark 1 is the same as described above.

[0114] The Coating 2 includes the following:PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0115] The Alkoxylated Phosphate Ester is the same as described above.

[0116] The Polymer Component 1 is the same as described above.

[0117] Just as above, the data set forth above shows dusting performance that is comparable to the market benchmark polyvinyl acetate copolymer and does so while not be considered a microplastic and thus not subject to microplastic regulations. Moreover, com seed have highly hydrophobic surfaces but the aqueous coating composition according to this disclosure performs unexpectedly well in terms of dusting and delivers results well below the market required threshold, which is superior to what is known.Example 3

[0118] In a third experiment, treated corn seeds are evaluated. A fifth group of seeds is coated with a commercial benchmark. A sixth group of seeds is coated with an aqueous seed coating composition according to this disclosure (Coating 3). After formation, the seeds are evaluated to determine dust-off using a modification of the aforementioned method, where dusting was performed using rotation speed of 40 rpm for 10 min at airflow of 20 l / min. The results of a single measurement per treatment is reported below:

[0119] The Commercial Benchmark 1 is the same as described above.

[0120] The Coating 3 includes the following:PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0121] The Acrylate Copolymer is a hydrophobically modified comb polymer as is described in at least PCT / EP2023 / 078411, which is expressly incorporated herein by reference in its entirety in various non-limiting embodiments.

[0122] The Polymer Component 1 is the same as described above.

[0123] Just as above, the data set forth above shows dusting performance that is superior to the market benchmark polyvinyl acetate copolymer and does so while not be considered a microplastic and thus not subject to microplastic regulations. Moreover, this coating composition includes a high dose of imidacloprid to show dusting performance with a challenging formulation. Unexpectedly, the coating composition without addition of wetting agent showed remarkable dusting performance on the com weed with hydrophobic irregular surface. This is both superior to what is known and unexpected to the person of skill in the art.Example 4

[0124] In a fourth experiment, treated sunflower seeds are evaluated. A seventh group of seeds is coated with a commercial benchmark. An eighth group of seeds is coated with an aqueous seed coating composition according to this disclosure (Coating 4). After formation, the seeds are evaluated to determine dust-off using the aforementioned method wherein an average of two measurements is reported below:PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0125] The Commercial Benchmark 2 is Liquid Coat Sapphire Blue by Ad Terrain which is a film coating used in agricultural applications, specifically designed for seed treatments.

[0126] The Coating 4 includes the following:

[0127] The Alkoxylated Phosphate Ester is the same as described above.

[0128] The Polymer Component 1 is the same as described above.

[0129] Just as above, the data set forth above shows dusting performance that is superior to the market benchmark polyvinyl acetate copolymer and does so while not be considered a microplastic and thus not subject to microplastic regulations. Surprisingly, the aqueous seed coating composition of this disclosure also exhibits marked dust reduction if applied as a liquid coat.Example 5

[0130] In a fifth experiment, treated com seeds are evaluated. Groups of seeds labeled samples 9 to 14 below are coated with aqueous seed coating compositions according to this disclosure (Coatings 5-10). The Coatings 5-10 include the following and are the same but for the Polymer Component.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0131] The Polymer Components 5-10 are each the same as Polymer Component 1 with the following changes in amounts of the acrylate copolymer and the single polyurethane:

[0132] After coating, the seeds are evaluated to determine dust-off using the modification of the aforementioned method, where dusting was performed during 5 min at rotation of speed of 40 rpm at airflow of 20 l / min. The results of a single measurement per treatment is reported below.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0133] The results are also visually depicted in the line graph of Figure 1 and demonstrate that the combination of polymeric components (1) and (2) exhibits unexpected synergies leading to a dust reduction effect that is more than 2 times higher compared to results achieved using the single components alone. This is clearly superior to, and unexpected over, what is known.Additional Examples

[0134] In additional experiments, treated com seeds are evaluated. Groups of seeds are coated with aqueous seed coating compositions according to this disclosure. The Coatings include the following for the Imidacloprid examples and are the same as each other but for the Polymer Component.

[0135] The Coatings include the following for the Tebuconazole examples and are the same as each other but for the Polymer Component.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0136] The Polymer Components used for these experiments are the same as Polymer Component 1 relative to the acrylate but differ from Polymer Component 1 relative to the polyurethane, as set forth in detail below.

[0137] The Polymer Components are as follows:Polymer Component A: is a mixture of:(1) an acrylate copolymer comprising the reaction product of:(a) butyl acrylate;(b) methyl methacrylate; and(c) methacrylic acid; in a molar ratio of about [(35-40):(45-50):(15-20)]; and(2) a single polyurethane that is the reaction product of:(i) a 2,2-hydroxymethyl-substituted carboxylic acid of the structure:wherein R is methyl,(ii) polypropylene glycol having a Mw of about lOOOg / mol; and isosorbide; and(iii) IPDI.Polymer Component B: is a mixture of:(1) an acrylate copolymer comprising the reaction product of:(a) butyl acrylate;(b) methyl methacrylate; andPCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC(c) methacrylic acid; in a molar ratio of about [(35-40):(45-50):(15-20)]; and(2) a single polyurethane that is the reaction product of:(i) a 2,2-hydroxymethyl-substituted carboxylic acid of the structure:ClhOIII ■R— c— coonICHjOH wherein R is methyl,(ii) polypropylene glycol having a Mw of about lOOOg / mol; and propoxylated isosorbide; and(iii) IPDI.Polymer Component C: is a mixture of:(1) an acrylate copolymer comprising the reaction product of:(a) butyl acrylate;(b) methyl methacrylate; and(c) methacrylic acid; in a molar ratio of about [(35-40):(45-50):(15-20)]; and(2) a single polyurethane that is the reaction product of:(i) a 2,2-hydroxymethyl-substituted carboxylic acid of the structure:wherein R is methyl,(ii) polypropylene glycol having a Mw of about lOOOg / mol; and an aromatic polyester polyol formed from diethylene glycol and phthalic anhydride; and(iii) IPDI.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0138] Each of the Polymer Components A-C are then used to determine dust-off values wherein the amount of polyurethane and the amount of acrylate copolymer are varied as set forth below. These values are then compared to values generated using Polymer Component 1.

[0139] More specifically, the seeds are evaluated to determine dust-off using the modification of the aforementioned method, where dusting was performed during 5 min at rotation of speed of 40 rpm at airflow of 20 l / min. The results of a single measurement per treatment is reported below as Dust Rate (g or mg / 100,000 seeds depending on samples as specified below).PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC

[0140] The data set forth above demonstrates superior results because it shows that various polyurethanes described herein produce excellent results.

[0141] While at least one exemplary embodiment has been presented in the foregoing detailed description, it should be appreciated that a vast number of variations exist. It should also be appreciated that the exemplary embodiment or exemplary embodiments are only examples, and are not intended to limit the scope, applicability, or configuration in any way. Rather, the foregoing detailed description will provide those skilled in the art with a convenient road map for implementing an exemplary embodiment. It being understood that various changes may be made in the function and arrangement of elements described in an exemplary embodiment without departing from the scope as set forth in the appended claims.

Claims

PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PCCLAIMSWhat is claimed is:

1. An aqueous seed coating composition comprising: about 1 to about 80 weight percent of water based on a total weight of the coating composition; and about 1 to about 50 weight percent actives of a formulation based on a total weight of the coating composition, wherein said formulation comprises:A. a polymer component present in an amount of from about 0.5 to about 55 weight percent actives based on a total weight of said coating composition and comprising:(1) an acrylate copolymer present in an amount of from about 20 to about 40 weight percent based on a total weight of the polymer component and comprising the reaction product of(a) butyl acrylate;(b) methyl methacrylate; and(c) methacrylic acid; and(2) a single polyurethane present in an amount of from about 60 to about 80 weight percent based on a total weight of the polymer component and that is the reaction product of:(i) a 2,2-hydroxymethyl-substituted carboxylic acid of the structure:wherein R is a C1-C3 alkyl group,(ii) an active hydrogen containing component, other than the 2,2- hydroxymethyl-substituted carboxylic acid, comprising: a polyalkylene glycol, a polyalkoxylated bisphenol A, an isosorbide, a polyether polyol,PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC a polyester polyol, a poly ether amine; or combinations thereof; and(iii) a diisocyanate;B. a filler present in an amount of from about 0 to about 40 weight percent actives based on a total weight the coating composition;C. a wetting agent present in an amount of from about 0 to about 15 weight percent actives based on a total weight the coating composition;D. a dispersing agent present in an amount of from about 0.1 to about 5 weight percent actives based on a total weight the coating composition.

2. The coating composition of claim 1 wherein the polyurethane is neutralized with a base chosen from sodium hydroxide, potassium hydroxide, 2-amino-2-methyl-l -propanol, hydroxyaminobutane, histidine, tris(hydroxymethyl)-aminomethane, triisopropanolamine, stearamine, triethanolamine, triethylamine, and combinations thereof.

3. The coating composition of claim 1 wherein the polyurethane is not neutralized.

4. The coating composition of any preceding claim wherein the 2,2-hydroxymethyl- substituted carboxylic acid is 2,2-di-(hydroxymethyl)propionic acid.

5. The coating composition of any preceding claim wherein the poly alkylene glycol is utilized and is polypropylene glycol.

6. The coating composition of claim 5 wherein the polypropylene glycol has a weight average molecular weight of from about 900 to about 1100 g / mol.

7. The coating composition of any preceding claim wherein the polyalkoxylated bisphenol A is utilized and comprises about 4 moles of propylene oxide and about 2 moles of ethylene oxide.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC8. The coating composition of any preceding claim wherein the isosorbide is utilized and has the structure:alkoxylated derivative thereof.

9. The coating composition of any preceding claim wherein the polyether polyol is utilized and is the reaction product of diethylene glycol and phthalic anhydride.

10. The coating composition of any preceding claim wherein the polyether amine is utilized and has the formula H2N-(CHCH3CH2O)i9(CH2CH2O)3-CH3.

11. The coating composition of any preceding claim wherein the (iii) diisocyanate is chosen from methylene-di-p-phenyl diisocyanate, methylene-bis-(4-cyclohexylisocyanate), isophorone diisocyanate, toluene diisocyanate, and combinations thereof.

12. The coating composition of any preceding claim wherein the polyurethane has a weight average molecular weight of from about 25 to about 50 KDa.

13. The coating composition of any preceding claim wherein the acrylate copolymer has a weight average molecular weight of from about 70 to about 100 KDa and is the reaction product of:(a) about 30 to 50 weight percent actives of the butyl acrylate based on a total weight of the reaction product;(b) about 30 to about 50 weight percent actives of the methyl methacrylate based on a total weight of the reaction product; and(c) about 5 to about 25 weight percent actives of the methacrylic acid based on a total weight of the reaction product.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC14. The coating composition of any preceding claim further comprising an active ingredient chosen from pesticides, nematicides, fungicides, inoculants, biostimulants, fertilizers, micronutrients, and combinations thereof, optionally chosen from imidacloprid, tebuconazole, and combinations thereof.

15. An aqueous seed coating composition comprising: about 1 to about 80 weight percent of water based on a total weight of the coating composition; and about 1 to about 50 weight percent actives of a formulation based on a total weight of the coating composition, wherein said formulation comprises:A. a polymer component present in an amount of from about 0.5 to about 55 weight percent actives based on a total weight of said coating composition and comprising:(1) an acrylate copolymer present in about 30 weight percent based on a total weight of the polymer component and comprising the reaction product of:(a) butyl acrylate;(b) methyl methacrylate; and(c) methacrylic acid; in a molar ratio of about [(35-40):(45-50):(15-20)]; and(2) a single polyurethane present in about 70 weight percent based on a total weight of the polymer component and that is the reaction product of:(i) a 2,2-hydroxymethyl-substituted carboxylic acid of the structure:wherein R is methyl,(ii) polypropylene glycol having a Mw of about lOOOg / mol; bisphenol A alkoxylated with 1 mole of ethylene oxide and2 moles of propylene oxide on each flank;H2N-(CHCH3CH2O) i9(CH2CH2O)3-CH3; and(iii) IPDI.PCT PATENT APPLICATIONAttorney Docket No.: 364.1538PC16. The coating composition of claim 15 further comprising an active ingredient chosen from pesticides, nematicides, fungicides, inoculants, biostimulants, fertilizers, micronutrients, and combinations thereof.

17. The coating composition of claim 16 wherein the active ingredient is chosen from imidacloprid, tebuconazole, and combinations thereof.

18. A system for coating seeds, said system comprising a seed; and the coating composition of any preceding claim.

19. A coated seed comprising: a seed; and a protective layer disposed about a least a portion of the seed and comprising the formulation of the coating composition of any preceding claim.

20. A method of coating seeds, said method comprising the steps of: providing a seed; and coating at least a portion of the seed with a protective layer comprising the formulation of the coating composition of any preceding claim.

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