Sulfopolyesters useful as seed coating compositions and coated seeds prepared from the seed coating compositions thereof

Abstract

The present application discloses seed coating compositions comprising sulfopolyesters that are biodegradable. The compositions exhibits improved seed binder characteristics compared to the same compositions without the sulfopolyesters. Seeds coated with the compositions are also disclosed as well as methods of preparing the coated seeds.

Description

[0001] SULFOPOLYESTERS USEFUL AS SEED COATING COMPOSITIONS AND COATED SEEDS PREPARED FROM THE SEED COATING COMPOSITIONS THEREOF

[0002] BACKGROUND OF THE INVENTION

[0003] Seed coatings play a vital role in modern agriculture by enhancing crop health, reducing losses, and improving yields. These coatings typically include active ingredients for pest and disease control, such as insecticides and fungicides, along with nutrients, biostimulants, and microbial inoculants that enhance nitrogen uptake and improve seedling health.

[0004] The seed coatings applied to crop seeds use polymeric binders to ensure adhesion of the coatings, maintaining active ingredients around the seed during processing, handling, and in its surroundings in the soil after sowing. Seed binders minimize pesticide and pigment dust-off during processing, storage, and sowing, a concern the industry is addressing. Individual countries are now setting dust-off limits, such as 0.75 g of dust per 100,000 seeds for corn, based on the European Seed Treatment Assurance (ESTA) standards developed by Euroseeds.

[0005] Environmental concerns about microplastics, which are found globally and within living organisms, are driving policymakers to restrict their use. In 2023, the European Chemicals Agency (ECHA) introduced a regulation aimed at reducing the environmental impact of microplastics. The regulation focuses on restricting the use of intentionally added microplastics in various products, including cosmetics, detergents, fertilizers, plant protection products, and other applications where microplastics are commonly used. This includes banning microplastic-forming materials in seed coatings, necessitating the development of microplastic-free polymeric binders. These measures are part of the European Union's broader strategy to address plastic pollution.

[0006] The definition according to Commission Regulation (EU) 2023 / 2055 defines microplastics as particles of plastic smaller than 5 mm in any dimension that are solid and insoluble in water. Exemptions from the ECHA microplasticdefinition include biodegradable polymers which meet specific biodegradability standards, naturally occurring polymers, i.e. unmodified natural polymers, polymers that have a solubility in water greater than 2 g / L, and polymers that do not contain carbon atoms in their chemical structure. Traditional binders, such as but not limited to styrene / acrylic copolymers, vinyl acetate / ethylene-acrylic copolymers, and PVP / starch copolymers, are now under scrutiny.

[0007] Seed binders are either integrated into the seed treatment formulation or applied separately. The incorporation of binders is limited by the preference for concentrated formulations, which restricts space for other components, and by the impact on properties such as viscosity and phase separation. Effective sticking properties require a significant amount of binder, typically 1-10% of the seed treatment’s solids content for acrylate copolymers. Treated seeds must exhibit low dust-off, good flowability, and high germination rates. An effective binder could reduce the amount needed relative to the solids content, offering cost savings and better performance on challenging seed surfaces such as but not limited to corn. Additionally, such biodegradable binders would be biodegradable.

[0008] The present application discloses seed coating compositions, coated seeds, and methods comprising sulfopolyesters that are beneficial as binders in the area of seed coatings. Seed coatings made from the sulfopolyesters are biocompatible with microorganisms, demonstrate good flowability with low dusting, do not negatively impact germination, and are biodegradable.

[0009] SUMMARY OF THE INVENTION

[0010] The present application discloses a seed coating composition, comprising:

[0011] (1) a binder comprising a sulfopolyester; and

[0012] (2) water,

[0013] wherein the binder is present at from 0.5 to 20 weight percent (“wt%”), wherein the wt% of each component in the seed coating composition is based on the total weight of the seed coating composition.The present application also discloses a coated seed comprising:

[0014] (1) a seed; and

[0015] (2) at least one coating layer,

[0016] wherein the at least one coating layer comprises:

[0017] (i) a first coating layer comprising a binder comprising a sulfopolyester.

[0018] The application also discloses uses of the seed coating compositions and method of using preparing the coated seeds.

[0019] DETAILED DESCRIPTION OF THE INVENTION

[0020] Definitions

[0021] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. In case of conflict, the present document, including definitions, will control. Example methods and materials are described below, although methods and materials similar or equivalent to those described herein can be used in practice or testing of the present disclosure. The materials, methods, and examples disclosed herein are illustrative only and not intended to be limiting.

[0022] The terms “comprises,” “include(s),” “having,” “has,” “can,” “contains,” and variants thereof, as used herein, are intended to be open-ended transitional phrases, terms, or words that do not preclude the possibility of additional acts or structures. The singular forms “a,” “an” and “the” include plural references unless the context clearly dictates otherwise. The present disclosure also contemplates other embodiments “comprising,” “consisting of’ and “consisting essentially of,” the embodiments or elements presented herein, whether explicitly set forth or not

[0023] Definitions of specific functional groups and chemical terms are described in more detail below. For purposes of this disclosure, the chemical elements are identified in accordance with the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75thEd., inside cover, and specific functional groups are generally defined as described therein.For the recitation of numeric ranges herein, each intervening number there between with the same degree of precision is explicitly contemplated. For example, for the range of 6-9, the numbers 7 and 8 are contemplated in addition to 6 and 9, and for the range 6.0-7.0, the number 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, and 7.0 are explicitly contemplated.

[0024] The modifier “about" used in connection with a quantity is inclusive of the stated value and has the meaning dictated by the context (for example, it includes at least the degree of error associated with the measurement of the particular quantity). The modifier “about" should also be considered as disclosing the range defined by the absolute values of the two endpoints. For example, the expression “from about 2 to about 4" also discloses the range “from 2 to 4.” The term “about” may refer to plus or minus 10% of the indicated number. For example, “about 10%” may indicate a range of 9% to 11%, and “about 1 " may mean from 0.9-1.1. Other meanings of “about" may be apparent from the context, such as rounding off, so, for example “about 1” may also mean from 0.5 to 1.4.

[0025] “Binder” is a material or blend of materials applied to seeds to promote uniform deposition, cohesive attachment, and mechanical stabilization of active ingredients and additives. Binders should improve seed handling, protect functional additives, and maintain seed physiological quality. Common examples of seed binders include waxes, natural polymers, synthetic polymers as well as modified biopolymers.

[0026] “Growth regulator” means a substance that, in low concentration, stimulates or inhibits the growth of plants, but is neither a nutrient nor a biostimulant. Growth regulators can be used to increase branching, suppressing shoot growth, increasing return bloom, removing excess fruit, or altering fruit maturity. Numerous factors affect growth regulator performance including how well the chemical is absorbed by the plant, tree vigor and age, dose, timing, cultivar, and weather conditions before, during, and after application. Growth regulators can be grouped into five classes: compounds related to auxins, gibberellins and inhibitors of gibberellin biosynthesis,cytokinins, abscisic acid and compounds affecting the ethylene status. Products that block the biosynthesis of plant hormones are also available (Apogee, Retain).

[0027] “Biostimulants” means a plant conditioner or bioeffector that is either a substance, a microorganism, an amino acid, an oligosaccharide, a peptide, an hormone, mixtures of materials used to promote the growth of crop plants and include natural or artificial plant grow regulators and biofertilizers. They do not include pesticides or fertilizers. The concept has been developed on the basis of the idea that plants are not isolated entities but grow within a complex ecosystem involving interactions with multiple organisms and that the strengths of these associations can be modified to enhance plant growth.

[0028] “Dispersion” as used herein refers to a system in which distributed particles of one material are uniformly dispersed in a continuous phase of another material. It is contemplated that the distributed particles may be solid or liquid particles, which may be dispersed in a continuous liquid phase.

[0029] “Sprayability” or “sprayable” as the term is used herein refers to the ability of a liquid or gel to be driven or dispersed in air as, for example, particles, drops or droplets. The liquid or gel can be ejected, blown, or forced in or through the air in the form of droplets or an aerosol, optionally through a nozzle, typically under pressure.

[0030] “Pesticides” are substances or microorganisms, or a mixtures intended for destroying, repelling, or mitigating any unwanted pest(s), including particularly any organism that may have a negative impact on a crop. The term pesticide describes a broad category that includes acaricides (to eradicate ticks and mites), bactericides, fungicides, herbicides, insecticides, larvicides, miticides, molluscicides, nematicides, piscicides, rodenticides, and slimicides (anti-slime agents). The following paragraphs provide non-limiting, representative examples of various pesticides; additional examples, including biopesticide examples, will be recognized by those of ordinary skill in the art.COMPOSITIONS

[0031] The present application discloses a seed coating composition, comprising: (1 ) a binder comprising a sulfopolyester; and (2) water, wherein the binder is present at from 0.5 to 20 weight percent (“wt%”), wherein the wt% of each component in the seed coating composition is based on the total weight of the seed coating composition.

[0032] In one embodiment or in combination with any other embodiment disclosed herein, wherein the composition further comprises (3) a surfactant.

[0033] In one class of this embodiment or in combination with any other class of this embodiment, the surfactant is present at from 0.1 to 20wt%, or 0.1 to 15wt%, or 0.1 to 10wt%, or 0.1 to 5wt%, or 0.1 to 3wt%, or 0.1 to 1wt%, or 0.5 to 20wt%, or 0.5 to 15wt%, or 0.5 to 10wt%, or 0.5 to 5wt%, or 0.5 to 3wt%, or 0.5 to 1wt%, or 1 to 20wt%, or 1 to 15wt%, or 1 to 10wt%, or 1 to 5wt%, or 1 to 3wt%, or 3 to 20wt%, or 3 to 15wt%, or 3 to 10wt%, or 3 to 5wt%, 5 to 20wt%, or 5 to 15wt%, or 5 to 10wt%, or 10 to 20wt%, or 10 to 15wt%, 15 to 20wt%, based on the total weight of the seed coating composition.

[0034] In one class of this embodiment or in combination with any other class in this embodiment, the surfactant is a dispersant, a wetting agent, or a combination thereof. In a subclass of this class, the surfactant is a dispersant. In a subclass of this class, the surfactant is a wetting agent. In a subclass of this class, the surfactant is a combination of a dispersant and a wetting agent.

[0035] In one class of this embodiment or in combination with any other class in this embodiment, the binder comprises 20 to 100wt%, or 25 to 100wt%, or 30 to 100wt%, or 40 to 100wt%, or 50 to 100wt%, or 50 to 90wt%, or 50 to 80wt%, or 50 to 70wt%, or 50 to 60wt%, or 60 to 100wt%, 60 to 90wt%, or 60 to 80wt%, or 60 to 70wt%, or 70 to 100wt%, or 70 to 90wt%, or 70 to 80wt%, or 80 to 100wt%, or 80 to 90wt%, or 90 to 100wt%, or 100wt% of the sulfopolyester, based on the total weight of the binder.

[0036] In one embodiment or in combination with any other embodiment disclosed herein, the active ingredient is chosen from a microbial organism, a fungicide, an insecticide, a herbicide, a herbicide safener, a nematicide, anacaricide, a plant growth regulator, a biostimulant, a nutrient, an inoculant, a protein, a fertilizer, or a combination thereof.

[0037] In one class of this embodiment or in combination with any other class of this embodiment, the fungicide is a chemical or chemical class chosen from 1,2,4-thiadiazole, 2,6-dinitro-aniline, 4-quinolyl-acetate, carboxylic acid, enopyranuronic acid, phthalamic acid, acylalanine, allylamine, mandelic acid amides, cinnamic acid amides, aminocyanoacrylate, amino- pyrazolinone, anilinopyrimidine, anthraquinone, aryloxyquinoline, Bacillus sp. and the produced fungicide lipopeptides, benzene sulfonamide, benzylcarbamate, benzimidazole, benzisothiazole, benzophenone, benzoylpyridine, benzothiadiazole BTH, benzotriazine, butyrolactone, carbamate, carboxamide, cyanoacetamide-oxime, cyanoimidazole, cyano- methylene-thiazolidine, cyclopropane carboxamide, chloronitrile, triphenyltin compounds, dicarboximide, dihydro-dioxazine, dinitrophenyl crotonate, dithiocarbamates and relative, dithiolane, spirocetal-amine, ethyl phosphonate, ethylamino-thiazol-carboxamide, phenyl-acetamide, phenyl-benzamide, phenyl-oxo-ethyl thiophene amide, phenylpyrrole, phenylurea, phosphonate, phosphorothiolate, phthalimide, furan-carboxamide, guanidine, aromatic hydrocarbon, terpene hydrocarbons and terpene alcohols, hydroxy- (2-amino-) pyrimidine, hydroxy aniline, imidazole, imidazolinone, inorganic (copper), inorganic (sulfur), isobenzofuranone, isothiazolone, isoxazole, maleimide, methoxy-acetamide, a methoxy-acrylate, methoxy-carbamate, Reynoutria sp. extract, a morpholine, a N-phenyl carbamate, N-methoxy-(phenyl-ethyl)-pyrazol- carboxamide, pyrimidine peptidyl nucleoside, oxatin-carboxamide, oxazolidine-dione, oxazolidinone, oximine-acetamide, oximine-acetate, a piperazine, a piperidine, a piperidinyl-thiazole-isoxazoline, a pyrazole-4-carboxamide, pyrazole-5-carboxamide, pyridazinone, pyridine, pyridine- carboxamide, pyridinyl-ethyl benzamide, pyridinylmethyl-benzamide, pyrimidine, pyrimidinamine, pyrimidinone-hydrazone, pyrrolo-quinolinone, polypeptide (lectin), a polysaccharide, a propionamide, a quinazolinone, a quinoxaline, a sulfamoyltriazole, a sulfonamide, a tetrazoyloyloxime, a thiadiazol- carboxamide, thiazol-carboxamide, thiocarbamate, thiophanate, thiophenecarboxamide, toluamide, a triazine, a triazole, triazolintione, triazolobenzo- thiazole, triazole-pyrimidylamine, Trichoderma sp. and produced fungicidal metabolites, trifluoroethylcarbamate, valinamide carbamate, tebuconazole, difenoconazole, fludioxonil, metalaxyl, azoxystrobin, thiabendazole, benodanil, flutolanil, fluopyram, mepronil, isofetamid, fenfuram, oxycarboxin, thifluzamide, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, benzovindiflupyr, or combinations thereof.

[0038] In one class of this embodiment or in combination with any other class of this embodiment, the insecticide is a chemical or chemical class chosen from thiamethoxam, clothianidin, imidacloprid, fipronil, abamectin, chlorantraniliprole, cyantraniliprole, flubendiamide, a mitochondrial electron transport inhibitor (“METI”) acaricides, acequinocyl, an aliphatic halogenated insecticide, amitraz, nereistoxin analogues, a juvenile hormone analogue, an avermectin, a milbemycin insecticide, azadirachtin, Bacillus sp. and the insecticidal proteins that they produce, benzoylurea, benzoximate, bifenazate, a borate, borax, bromopropylate, buprofezin, butenolides, lime sulphur, a carbamate insecticide, a carboxanilide insecticide, a cyanide, a cyclodiene insecticide, cyromazine, clofentezine, diflovidazin, hexithiazoxy, chlorfenapyr, dinitrophenol, sulfluramid, chloropicrin, dichloro-diphenyl-trichloroethane, methoxychlor, a tetronic and tetramic acid derivative, a betaketonitrile derivative, an azomethine pyridine derivative, a diacylhydrazine, diafenthiuron, a diamide insecticide, dicofol, a spinosyne, ethoxazole, a phenylpyrazole insecticide, fenoxycarb, a rotenoid-type saponin flavone insecticide, flonicamide, fluacripyrim, a fluoride salt, a phosphide insecticide, a methyl isothiocyanate precursor, hydramethylnone, inorganic phosphine precursor, an organophosphate insecticide, a mesoionic insecticide, a neonicotinoid insecticide, nicotine, an organotin insecticide, an oxadiazine insecticide, GS-omega / kappa HXTX- Hvla peptide, a pyrazole insecticide, a pyrethroid insecticide, a pyrethrin insecticide, pyridalyl, pyriproxyfen, propargite,quinomethionate, rotenone, a semicarbazone, a fluoroaliphatic sulfonamide insecticide, sulfoxaflor, tetradifone, or combinations thereof.

[0039] In one class of this embodiment or in combination with any other class of this embodiment, the herbicide is a chemical or chemical class chosen from an acetamide, an arylaminopropionic acid, benzoic acid, chlorocarbonic acid, phenoxycarboxylic acid, phosphinic acid, quinolinecarboxylic acid, an amide, an aryloxyphenoxypropionates, an arylpicolinate, a benzamide, a benzofuran, a benzothiadiazinone, a bipyridylium, a carbamate, a cyclohexanedione, a chloroacetamides, a chloroacetamide, a chloroacetamide, a diphenyl ether, a dinitroaniline, a dinitrophenol, a phenylcarbamate, a phenylpyrazole, a phenylpyrazoline, a phenyl- pyridazine, a phosphoroamidate, a phosphorodithioate, a semicarbazone phthalamate, a glycine, a imidazolinone, a long chain fatty acid inhibitor, an isoxazole, a isoxazolidinone, a N-phenylphthalimide, a nitrile, an organoarsenical, an oxadiazole, an oxazolidinedinone, an oxiacetamide, a pyrazole, a pyrazolium, a pyridazinones, a pyridine, a pyridinecarboxamide, a pyrimidindione, a pyrimidinyl benzoate, a thiopyrimidinyl benzoates, a sulfonylaminocarbonyl-triazolinone, a sulfonylurea, a tetrazolinone, a thiadiazole, a thiocarbamate, a triazine, a triazinone, a triazole, a triazolinone, a triazolocarboxamide, a triazolopyrimidine, a tricetone, a uracil, a urea or combination thereof.

[0040] In one class of this embodiment or in combination with any other class of this embodiment, the herbicide safener is a chemical or chemical class chosen from an ammonium acetate, a benoxacor, a cloquintocet, a cloquintocet-acid, a cloquintocet-mexyl, a cyometrinil, a cyprosulfamide, a dichlormid, a dicyclonon, a dietholate, a disodium EDTA, an ethoxylated isodecyl alcohol, a fenchlorazole, a fenchlorazole-ethyl, afenclorim, aflurazole, a fluxofenim, a furilazole, a glycine, an isoxadifen, an isoxadifen-ethyl, a mefenpyr, a mefenpyr-diethyl, a mephenate, a naphthalic anhydride, an oxabetrinil, a piperonyl butoxide, a rapeseed oil, or combination thereof.

[0041] In one class of this embodiment or in combination with any other class of this embodiment, the nematicide is a chemical or chemical class chosen froma halogenated aliphatic, avermectin, a benzamides, a plant extract, a fluoroalkenyle (-thiother), a methyl isothiocyanate precursor, a benzofuranyl methylcarbamate, a organophosphate or combinations thereof.

[0042] In one class of this embodiment or in combination with any other class of this embodiment, the nutrient is a macronutrient, a micronutrient, or a combination thereof.

[0043] In one subclass of this class, the macronutrient is chosen from N, P, K, S, Ca, Mg, or combinations thereof.

[0044] In one subclass of this class, the micronutrient can be selected from one or more of Fe, Zn, Mn, Cu, Ni, Cl, Mo, B, Si, Se, Al, Co, V, Na, or combinations thereof.

[0045] In one class of this embodiment or in combination with any other class of this embodiment, the microorganism is one or more bacteria, fungi, mites, nematodes, or combinations thereof.

[0046] In one subclass of this class, the microorganism is Acetobacter spp., Agrobacterium spp., Amblyseius spp., Ampelomyces spp., Aspergillus spp., Aureobasidium spp., Azospirillum spp., Azotobacter spp., Azozpirillum spp., Bacillus spp., Baculovirus spp., Beauveria spp., Bradyrhizobium spp., Candida spp., Cladosporium spp., Coniothyrium spp., Cotesia spp., Cryptolaemus spp., Deladenus spp., Ectomycorrhiza, Endomycorrhiza, Epichlö spp., Funnelifomis spp., Gliocladium spp., Glomus spp., Gluconacetobacter spp., Heterorhabditis spp., Isaria spp., Metarhizium spp., Myrothecium spp., Neoseiulus spp., Orius spp., Paecilomyces spp., Pasteuria spp., Penicillium spp., Phytoseiulus spp., Piriformospora spp., Pseudomonas spp., Pseudozyma spp., Purpureocillium spp., Rhizobium spp., Rhizoglomus spp., Serratia spp., Sinorhizobium spp., Stratiolaelaps spp., Streptomyces spp., Telenomus spp., Trichogramma spp., Trichoderma spp., or combinations thereof.

[0047] In one class of this embodiment or in combination with any other class of this embodiment, the plant growth regulator or biostimulant are chosen from chemicals or chemical classes chosen from a dioxocyclohexanecarboxylic acid, an indolalcanoic acid, an aliphatic alcohol, a quaternary ammonium, acarbimide, a carboxanilide, a cycloalkene, a cyclohexadione, a cytokinin, a dinitroaniline, an ethylene inhibitor, an ethylene precursor, gibberellin, a pyridazinadione, a sesquiterpenes, a triazole, a benzothiadiazol, nitric oxide, a nitric oxide precursor, methyl salicylate, methyl jasmonate, a protein, a polypeptide, a polyamine, an algae extract, a fulvic acid, a humic acid, a plant growth promoting rhizobacteria, or combinations thereof.

[0048] In one class of this embodiment or in combination with any other class of this embodiment, the composition further comprises a pigment, an antifreeze, a preservative, an antifoaming agent, a suspending agent, a polymer that is different than the binder, a plasticizer, a spreading agent, an emulsifier, a stabilizer, a rheology modifier, a mineral (e.g., a mineral clay), a filler, a disintegrating agent, or a combination thereof.

[0049] In one embodiment or in combination with any other embodiment, class or subclass, the sulfopolyester is a random polymer.

[0050] In one embodiment or in combination with any other embodiment, class, or subclass disclosed herein, the sulfopolyester comprises the reaction product of (a) an acid component, comprising: (i) a diacid or derivative that is chosen from a (C3-s)cycloalkyl dicarboxylic acid or derivative; a (Cs)aryl dicarboxylic acid or derivative; a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched; a (C2-3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched; or a combination thereof, (ii) a o o

[0051] o=s=o

[0052]

[0053] R1sulfonated dicarboxylic acid or ester of the formula I:1wherein: R is hydrogen or (Ci-4)alkyl; R1isξ-O(C1-4)alkyl orξ-O-M+

[0054]

[0055] O M; and M+is H+, Na+, K+, Li+, or+NH4, and (b) a diol component, comprising an unbranched or branched (C2-i2)alkyl diol, a (C3-8)cycloalkyl dimethanol, a (c3-8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci-4)alkyl groups; acompound of formula II: H-(OCH2CH2)n-OH II, wherein n is an integer from 2 to 500; or a combination thereof.

[0056] In one class of this embodiment or in combination with any other class or subclass, the sulfopolyester further comprises the reaction product of (a) an ultraviolet light absorbing component, comprising: (i) an ultraviolet light absorbing monocarboxylic acid or ester (“UVMA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVMA is a benzoic acid or ester, a cinnamic acid or ester, a 2-benzoylbenzoicacid or ester, a 3,3-diphenylacrylicacid or ester, or combination thereof, wherein each is unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl; (ii) an ultraviolet light absorbing dicarboxylic acid or derivative (“UVDA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVDA is a naphthalene dicarboxylic acid or derivative, a 1,1 ’-diphenyl dicarboxylic acid or derivative, a phthalic acid or derivative, a 5-amino-isophthalic acid or ester, a 5-(di(Ci-4)alkylamino)isophthalic acid or ester, a 4,4'-methylenebis(3-hydroxy-2-naphthoic acid) or ester, 2-benzylmalonic acid or ester, a 5,5'-methylenebis(2-aminobenzoic acid) or ester; or (iii) a combination thereof, (d) a water dispersing component, comprising a compound of formula III: H-(OCH2CH2)n-O(Ci-4)alkyl III, wherein n is an integer from 2 to 500.

[0057] In one subclass of this class, the compound of formula III is present at from 0.4 to 10 mole% or 0.4 to 8 mole%, or 0.4 to 6 mole%, or 0.4 to 4 mole%, or 0.4 to 2 mole%, or 0.4 to 1 mole%, or 1 to 12 mole%, or 1 to 10 mole%, or 1 to 8 mole%, or 1 to 6 mole%, or 1 to 4 mole%, or 1 to 4 mole%, or 1 to 2 mole%, or 2 to 12 mole%, or 2 to 10 mole%, or 2 to 8 mole%, or 2 to 6 mole%, or 2 to 4 mole%, or 4 to 12 mole%, or 4 to 10 mole%, or 4 to 8 mole%, or 4 to 6 mole%, or 6 to 12 mole%, or 6 to 10 mole%, or 6 to 8 mole%, or 8 to 12 mole%, or 8 to 10 mole%, or 10 to 12 mole%.In one subclass of this class or in combination with any other class or subclass, the compound of formula III is the compound of formula Illa: H-(OCH2CH2)n-OCH3, IIIa, wherein n is an integer from 2-500.

[0058] In one subclass of this class or in combination with any other class or subclass, the compound of formula III is the compound of formula IIIb:

[0059] H-(OCH2CH2)n-OCH2CH3,

[0060] IIIb

[0061] wherein n is an integer from 2-500.

[0062] In one embodiment, or in combination with any other embodiment, class or subclass, the sulfopolyester has a glass transition temperature (“Tg”) that is in the range of from -60 to 70°C, or from -60 to 50°C, or from -60 to 30°C, or from -60 to 10°C, or from -60 to 0°C, or from -60 to -10°C, or from -60 to -30°C, or from -60 to -50°C, or -40 to 70°C, or from -40 to 50°C, or from -40 to 30°C, or from -40 to 10°C, or from -40 to 0°C, or from -40 to -10°C, or from -40 to -30°C, or from -40 to -50°C, or -20 to 70°C, or from -20 to 50°C, or from -20 to 30°C, or from -20 to 10°C, or from -20 to 0°C, or from -20 to -10°C, or from -20 to -30°C, or 0 to 70°C, or from 0 to 50°C, or from 0 to 30°C, or from 0 to 10°C, or 10 to 70°C, or from 10 to 50°C, or from 10 to 30°C, or 20 to 70°C, or from 20 to 50°C, or from 20 to 30°C, or 40 to 70°C, or from 40 to 50°C, 60 to 70°C.

[0063] In one embodiment or in combination with any other embodiment, class or subclass, the sulfopolyester exhibits a melting point (“Tm”) that is in the range of from 45 to 80°C, or from 45 to 70°C, or from 45 to 60°C, or from 45 to 50°C, or from 50 to 80°C, or from 50 to 70°C, or from 50 to 60°C, or 60 to 80°C, or from 60 to 70°C.

[0064] In one embodiment or in combination with any other embodiment, class, or subclass, the sulfopolyester is dispersible in water at 70°C to form a dispersion having at least 5 wt% of the sulfopolyester based on the total weight of the dispersion, wherein the sulfopolyester has a glass transition temperature (“Tg”) that is in the range of from -60 to 70°C and a melting point (“Tm”) that is in the range of from 45 to 80°C.In one embodiment or in combination with any other embodiment, class or subclass, the sulfopolyester exhibits an inherent viscosity (“IhV”) is in the range of 0.05 to 0.35 dL / g, or in the range of 0.05 to 0.30 dL / g, or in the range of 0.05 to 0.25 dL / g, or in the range of 0.05 to 0.20 dL / g, or in the range of 0.05 to 0.15 dL / g, or in the range of 0.05 to 0.10 dL / g, or in the range of 0.1 to 0.35 dL / g, or in the range of 0.1 to 0.30 dL / g, or in the range of 0.1 to 0.25 dL / g, or in the range of 0.1 to 0.20 dL / g, or in the range of 0.1 to 0.15 dL / g, or in the range of 0.15 to 0.35 dL / g, or in the range of 0.15 to 0.30 dL / g, or in the range of 0.15 to 0.25 dL / g, or in the range of 0.15 to 0.20 dL / g, or in the range of 0.2 to 0.35 dL / g, or in the range of 0.2 to 0.30 dL / g, or in the range of 0.2 to 0.25 dL / g, or in the range of 0.25 to 0.35 dL / g, or in the range of 0.25 to 0.30 dL / g, or in the range of 0.3 to 0.35 dL / g as determined in a 60 / 40 parts by weight solution of phenol / tetrachlorethane at 25°C and at a concentration of about 0.5 g of sulfopolyester in 100 mL of the solution of phenol / tetrachloroethane. In one embodiment or in combination with any other embodiment, class, or subclass, the sulfopolyester further comprises a branching component, comprising: (i) a branching polycarboxylic acid. In one embodiment or in combination with any other embodiment, the sulfopolyester further comprises a branching component, comprising: (ii) a branching polyol. In one embodiment or in combination with any other embodiment, the sulfopolyester further comprises a branching component, comprising: (iii) a branching polyfunctional compound.

[0065] In one embodiment or in combination with any other embodiment, class, or subclass, the branching component is present at from 0.05 to 4 mole %, or from 0.05 to 3.5 mole%, or from 0.05 to 3.0 mole%, or from 0.05 to 2.5 mole%, or from 0.05 to 2.0 mole%, or from 0.05 to 1.5 mole%, or from 0.05 to 1.0 mole%, or from 0.05 to 0.5 mole%, or from 0.05 to 0.25 mole%, or from 0.05 to 0.1 mole%, or from 0.1 to 4 mole %, or from 0.1 to 3.5 mole%, or from 0.1 to 3.0 mole%, or from 0.1 to 2.5 mole%, or from 0.1 to 2.0 mole%, or from 0.1 to 1.5 mole%, or from 0.1 to 1.0 mole%, or from 0.1 to 0.5 mole%, or from 0.1 to 0.25 mole%, 0.3 to 4 mole %, or from 0.3 to 3.5 mole%, or from 0.3 to 3.0mole%, or from 0.3 to 2.5 mole%, or from 0.3 to 2.0 mole%, or from 0.3 to 1.5 mole%, or from 0.3 to 1.0 mole%, or from 0.3 to 0.5 mole%, 0.5 to 4 mole %, or from 0.5 to 3.5 mole%, or from 0.5 to 3.0 mole%, or from 0.5 to 2.5 mole%, or from 0.5 to 2.0 mole%, or from 0.5 to 1.5 mole%, or from 0.5 to 1.0 mole%, or from 1 to 4 mole %, or from 1 to 3.5 mole%, or from 1 to 3.0 mole%, or from 1 to 2.5 mole%, or from 1 to 2.0 mole%, or from 1 to 1.5 mole%, or 2 to 4 mole %, or from 2 to 3.5 mole%, or from 2 to 3.0 mole%, or from 2 to 2.5 mole%, or from 3 to 4 mole %, or from 3 to 3.5 mole%.

[0066] In one embodiment or in combination with any other embodiment, class, or subclass, the branching polyol is 1,1,1 -trimethylol propane, 1,1,1-trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, sorbitol, or combinations thereof; wherein the branching polycarboxylic acid is trimellitic anhydride, pyromellitic dianhydride, or combinations thereof; and wherein the branching polyfunctional compound is dimethylol propionic acid.

[0067] In one embodiment or in combination with any other embodiment, class, or subclass, the sulfonated dicarboxylic acid or ester is present from 2.5 to 20 mole%, or from 2.5 to 15 mole%, or from 2.5 to 10 mole%, or from 2.5 to 5 mole%, or from 5 to 20 mole%, or from 5 to 15 mole%, or from 5 to 10 mole%, or from 10 to 20 mole%, or from 10 to 15 mole%, or from 15 to 20 mole%.

[0068] In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is an unbranched or branched (C2-12)alkyl diol or a compound of formula II, wherein n is an integer from 2 to 500; or a combination thereof. In one embodiment or in combination with any other embodiment, the diol component is an unbranched or branched (C2-12)alkyl diol. In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is a (C3-8)cycloalkyl dimethanol. In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is a (c3-8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci-4)alkyl groups. In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is a compound of formula II: H-(OCH2CH2)n-OH II, wherein n is an integer from 2 to500. In one class of this embodiment, n is an integer from 2 to 400, or from 2 to 300, or from 2 to 200, or from 2 to 100, or from 2 to 75, or from 2 to 50, or from 2 to 25, or from 2 to 15, or from 15 to 400, or from 15 to 300, or from 15 to 200, or from 15 to 100, or from 15 to 75, or from 15 to 50, or from 15 to 25, from 25 to 400, or from 25 to 300, or from 25 to 200, or from 25 to 100, or from 25 to 75, or from 25 to 50, or from 50 to 400, or from 50 to 300, or from 50 to 200, or from 50 to 100, or 50 to 75, or 75 to 400, or 75 to 300, or 75 to 200, or 75 to 100, or from 100 to 400, or from 100 to 300, or from 100 to 200, or from 200 to 400, or from 200 to 300, or from 300 to 400. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a benzoic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a cinnamic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a 2-benzoylbenzoic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a 3,3-diphenylacrylic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alky I.

[0069] In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a naphthalene dicarboxylic acid or derivative,

[0070] In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 1, 1 ’-diphenyl dicarboxylic acid or derivative. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a phthalic acid or derivative. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 5-amino-isophthalic acid or ester. In one embodiment or in combination with any otherembodiment, class, or subclass, the UVDA is a 5-(di(Ci-4)alkylamino)isophthalic acid or ester. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 4,4'-methylenebis(3-hydroxy-2-naphthoic acid) or ester. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is 2-benzylmalonic acid or ester. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 5,5'-methylenebis(2-aminobenzoic acid) or ester.

[0071] In one embodiment or in combination with any other embodiment, class, or subclass, the water dispersing component comprises a compound of formula III: H-(OCH2CH2)n-O(Ci-4)alkyl (III), wherein n is an integer from 2 to 500, or from 2 to 400, or from 2 to 300, or from 2 to 200, or from 2 to 100, or from 2 to 75, or from 2 to 50, or from 2 to 25, or from 2 to 15, or from 15 to 400, or from 15 to 300, or from 15 to 200, or from 15 to 100, or from 15 to 75, or from 15 to 50, or from 15 to 25, from 25 to 400, or from 25 to 300, or from 25 to 200, or from 25 to 100, or from 25 to 75, or from 25 to 50, or from 50 to 400, or from 50 to 300, or from 50 to 200, or from 50 to 100, or 50 to 75, or 75 to 400, or 75 to 300, or 75 to 200, or 75 to 100, or from 100 to 400, or from 100 to 300, or from 100 to 200, or from 200 to 400, or from 200 to 300, or from 300 to 400.

[0072] In one class of this embodiment, the (Ci-4)alkyl moiety in the compound of formula III is a methyl, ethyl, propyl, isopropyl, n-butyl, or isobutyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a methyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a ethyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a propyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a n-butyl.

[0073] In one class of this embodiment or in combination with any other class of this embodiment, the sulfopolyester is biodegradable.

[0074] In one class of this embodiment or in combination with any other class of this embodiment, wherein sulfopolyester exhibits a biodegradability of from 10-100%, or from 10-90%, or from 10-80%, or from 10-70%, or from 10-60%,or from 10-50%, or from 10-40%, or from 20-100%, or from 20-90%, or from 20-80%, or from 20-70%, or from 20-60%, or from 20-50%, or from 20-40%, or from 30-100%, or from 30-90%, or from 30-80%, or from 30-70%, or from 30-60%, or from 30-50%, or from 40-100%, or from 40-90%, or from 40-80%, or from 40-70%, or from 40-60%, or from 40-50%, or from 50-100%, or from 50-90%, or from 50-80%, or from 50-70%, or from 50-60%, or from 60-100%, or from 60-90%, or from 60-80%, or from 60-70%, or from 70-100%, or from 70-90%, or from 70-80%, or from 80-100%, or from 80-90%, at 56 days according to the OECD 301 F test method.

[0075] In one class or in combination with any other class of this embodiment, wherein the sulfopolyester exhibits at least 10% biodegradability, or at least 15% biodegradability, or at least 20% biodegradability, or at least 30% biodegradability, or t least 40% biodegradability, at least 45% biodegradability, or at least 50% biodegradability, or at least 55% biodegradability, at least 60% biodegradability, or at least 65% biodegradability, or at least 70% biodegradability, or at least 75% biodegradability, or at least 80% biodegradability, or at least 85% biodegradability, at 56 days according to the OECD 301 F test method.

[0076] The present application also discloses a use of the seed coating composition of any one of the previously disclosed seed coating compositions disclosed herein to coat seeds.

[0077] Coated Seed

[0078] The present application discloses a coated seed comprising: (1) a seed; and (2) at least one coating layer, wherein the at least one coating layer comprises: (i) a first coating layer comprising a binder comprising a sulfopolyester.

[0079] In one embodiment or in combination with any other embodiment, the first coating layer is disposed on the surface of the seed.

[0080] In one embodiment or in combination with any other embodiment, the coated seed further comprises a second coating layer.In one class of this embodiment or in combination with any other class of this embodiment, the second coating layer is disposed on the surface of the seed, below the first layer, or above the first layer.

[0081] In one subclass of this class, the second coating layer is disposed on the surface of the seed. In one subclass of this class, the second coating layer is disposed below the first layer. In one subclass of this class, the second coating layer is disposed above the first layer.

[0082] In one embodiment or in combination with any other embodiment, the binder comprises 20 to 100wt%, or 25 to 100wt%, or 30 to 100wt%, or 40 to 100wt%, or 50 to 100wt%, or 50 to 90wt%, or 50 to 80wt%, or 50 to 70wt%, or 50 to 60wt%, or 60 to 100wt%, 60 to 90wt%, or 60 to 80wt%, or 60 to 70wt%, or 70 to 100wt%, or 70 to 90wt%, or 70 to 80wt%, or 80 to 100wt%, or 80 to 90wt%, or 90 to 100wt%, or 100wt% of the sulfopolyester, based on the total weight of the binder.

[0083] In one embodiment or in combination with any other embodiment, one or more of the at least one coating layer further com prises an active ingredient. In one class of this embodiment, the active ingredient is an agrochemical active ingredient.

[0084] In one class of this embodiment, the active ingredient is chosen from a microbial organism, a fungicide, an insecticide, a herbicide, a herbicide safener, a nematicide, an acaricide, a plant growth regulator, a biostimulant, nutrients, an inoculant, a protein, a fertilizer, ora combination thereof.

[0085] In one subclass of this class or in combination with any other subclass of this class, the fungicide is a chemical or chemical class chosen from 1,2,4-thiadiazole, 2,6-dinitro-aniline, 4-quinolyl-acetate, carboxylic acid, enopyranuronic acid, phthalamic acid, acylalanine, allylamine, mandelic acid amides, cinnamic acid amides, aminocyanoacrylate, amino- pyrazolinone, anilinopyrimidine, anthraquinone, aryloxyquinoline, Bacillus sp. and the produced fungicide lipopeptides, benzene sulfonamide, benzylcarbamate, benzimidazole, benzisothiazole, benzophenone, benzoylpyridine, benzothiadiazole BTH, benzotriazine, butyrolactone, carbamate, carboxamide,cyanoacetamide-oxime, cyanoimidazole, cyano- methylene-thiazolidine, cyclopropane carboxamide, chloronitrile, triphenyltin compounds, dicarboximide, dihydro-dioxazine, dinitrophenyl crotonate, dithiocarbamates and relative, dithiolane, spirocetal-amine, ethyl phosphonate, ethylamino-thiazol-carboxamide, phenyl-acetamide, phenyl-benzamide, phenyl-oxo-ethyl thiophene amide, phenylpyrrole, phenylurea, phosphonate, phosphorothiolate, phthalimide, furan-carboxamide, guanidine, aromatic hydrocarbon, terpene hydrocarbons and terpene alcohols, hydroxy- (2-amino-) pyrimidine, hydroxy aniline, imidazole, imidazolinone, inorganic (copper), inorganic (sulfur), isobenzofuranone, isothiazolone, isoxazole, maleimide, methoxy-acetamide, a methoxy-acrylate, methoxy-carbamate, Reynoutria sp. extract, a morpholine, a N-phenyl carbamate, N-methoxy-(phenyl-ethyl)-pyrazol- carboxamide, pyrimidine peptidyl nucleoside, oxatin-carboxamide, oxazolidine-dione, oxazolidinone, oximine-acetamide, oximine-acetate, a piperazine, a piperidine, a piperidinyl-thiazole-isoxazoline, a pyrazole-4-carboxamide, pyrazole-5-carboxamide, pyridazinone, pyridine, pyridine- carboxamide, pyridinyl-ethyl benzamide, pyridinylmethyl-benzamide, pyrimidine, pyrimidinamine, pyrimidinone-hydrazone, pyrrolo-quinolinone, polypeptide (lectin), a polysaccharide, a propionamide, a quinazolinone, a quinoxaline, a sulfamoyltriazole, a sulfonamide, a tetrazoyloyloxime, a thiadiazol- carboxamide, thiazol-carboxamide, thiocarbamate, thiophanate, thiophenecarboxamide, toluamide, a triazine, a triazole, triazolintione, triazolobenzo- thiazole, triazole-pyrimidylamine, Trichoderma sp. and produced fungicidal metabolites, trifluoroethylcarbamate, valinamide carbamate, tebuconazole, difenoconazole, fludioxonil, metalaxyl, azoxystrobin, thiabendazole, benodanil, flutolanil, fluopyram, mepronil, isofetamid, fenfuram, oxycarboxin, thifluzamide, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, benzovindiflupyr, or combinations thereof.

[0086] In one subclass of this class or in combination with any other subclass of this class, the insecticide is a chemical or chemical class chosen from thiamethoxam, clothianidin, imidacloprid, fipronil, abamectin,chlorantraniliprole, cyantraniliprole, flubendiamide, a mitochondrial electron transport inhibitor (“METI”) acaricides, acequinocyl, an aliphatic halogenated insecticide, amitraz, nereistoxin analogues, a juvenile hormone analogue, an avermectin, a milbemycin insecticide, azadirachtin, Bacillus sp. and the insecticidal proteins that they produce, benzoylurea, benzoximate, bifenazate, a borate, borax, bromopropylate, buprofezin, butenolides, lime sulphur, a carbamate insecticide, a carboxanilide insecticide, a cyanide, a cyclodiene insecticide, cyromazine, clofentezine, diflovidazin, hexithiazoxy, chlorfenapyr, dinitrophenol, sulfluramid, chloropicrin, DDT, methoxychlor, a tetronic and tetramic acid derivative, a betaketonitrile derivative, an azomethine pyridine derivative, a diacylhydrazine, diafenthiuron, a diamide insecticide, dicofol, a spinosyne, ethoxazole, a phenylpyrazole insecticide, fenoxycarb, a rotenoid-type saponin flavone insecticide, flonicamide, fluacripyrim, a fluoride salt, a phosphide insecticide, a methyl isothiocyanate precursor, hydramethylnone, inorganic phosphine precursor, an organophosphate insecticide, a mesoionic insecticide, a neonicotinoid insecticide, nicotine, an organotin insecticide, an oxadiazine insecticide, GS-omega / kappa HXTX- Hvla peptide, a pyrazole insecticide, a pyrethroid insecticide, a pyrethrin insecticide, pyridalyl, pyriproxyfen, propargite, quinomethionate, rotenone, a semicarbazone, a fluoroaliphatic sulfonamide insecticide, sulfoxaflor, tetradifone, or combinations thereof.

[0087] In one subclass of this class or in combination with any other subclass of this class, the herbicide is a chemical or chemical class chosen from an acetamide, an arylaminopropionic acid, benzoic acid, chlorocarbonic acid, phenoxycarboxylic acid, phosphinic acid, quinolinecarboxylic acid, an amide, an aryloxyphenoxypropionates, an arylpicolinate, a benzamide, a benzofuran, a benzothiadiazinone, a bipyridylium, a carbamate, a cyclohexanedione, a chloroacetamides, a chloroacetamide, a chloroacetamide, a diphenyl ether, a dinitroaniline, a dinitrophenol, a phenylcarbamate, a phenylpyrazole, a phenylpyrazoline, a phenyl- pyridazine, a phosphoroamidate, a phosphorodithioate, a semicarbazone phthalamate, a glycine, a imidazolinone,a long chain fatty acid inhibitor, an isoxazole, a isoxazolidinone, a N-phenylphthalimide, a nitrile, an organoarsenical, an oxadiazole, an oxazolidinedinone, an oxiacetamide, a pyrazole, a pyrazolium, a pyridazinones, a pyridine, a pyridinecarboxamide, a pyrimidindione, a pyrimidinyl benzoate, a thiopyrimidinyl benzoates, a sulfonylaminocarbonyl-triazolinone, a sulfonylurea, a tetrazolinone, a thiadiazole, a thiocarbamate, a triazine, a triazinone, a triazole, a triazolinone, a triazolocarboxamide, a triazolopyrimidine, a tricetone, a uracil, a urea or combination thereof.

[0088] In one subclass of this class or in combination with any other subclass of this class, the herbicide safener is a chemical or chemical class chosen from an ammonium acetate, a benoxacor, a cloquintocet, a cloquintocet-acid, a cloquintocet-mexyl, a cyometrinil, a cyprosulfamide, a dichlormid, a dicyclonon, a dietholate, a disodium EDTA, an ethoxylated isodecyl alcohol, a fenchlorazole, a fenchlorazole-ethyl, a fenclorim, a flurazole, a fluxofenim, a furilazole, a glycine, an isoxadifen, an isoxadifen-ethyl, a mefenpyr, a mefenpyr-diethyl, a mephenate, a naphthalic anhydride, an oxabetrinil, a piperonyl butoxide, a rapeseed oil, or combination thereof.

[0089] In one subclass of this class or in combination with any other subclass of this class, the nematicide is a chemical or chemical class chosen from a halogenated aliphatic, avermectin, a benzamides, a plant extract, a fluoroalkenyle (-thiother), a methyl isothiocyanate precursor, a benzofuranyl methylcarbamate, a organophosphate or combinations thereof.

[0090] In one subclass of this class or in combination with any other subclass of this class, the nutrient is a macronutrient, a micronutrient, or a combination thereof. In one sub-subclass of this subclass, the macronutrient is chosen from N, P, K, S, Ca, Mg, or combinations thereof. In one sub-subclass of this subclass, the micronutrient can be selected from one or more of Fe, Zn, Mn, Cu, Ni, Cl, Mo, B, Si, Se, Al, Co, V, Na, or combinations thereof.

[0091] In one subclass of this class or in combination with any other subclass of this class, the microorganism is one or more bacteria, fungi, mites, nematodes, or combinations thereof.In one subclass of this class or in combination with any other subclass of this class,, the microorganism is Acetobacter spp., Agrobacterium spp., Amblyseius spp., Ampelomyces spp., Aspergillus spp., Aureobasidium spp., Azospirillum spp., Azotobacter spp., Azozpirillum spp., Bacillus spp., Baculovirus spp., Beauveria spp., Bradyrhizobium spp., Candida spp., Cladosporium spp., Coniothyrium spp., Cotesia spp., Cryptolaemus spp., Deladenus spp., Ectomycorrhiza, Endomycorrhiza, Epichlö spp., Funnelifomis spp., Gliocladium spp., Glomus spp., Gluconacetobacter spp., Heterorhabditis spp., Isaria spp., Metarhizium spp., Myrothecium spp., Neoseiulus spp., Orius spp., Paecilomyces spp., Pasteuria spp., Penicillium spp., Phytoseiulus spp., Piriformospora spp., Pseudomonas spp., Pseudozyma spp., Purpureocillium spp., Rhizobium spp., Rhizoglomus spp., Serratia spp., Sinorhizobium spp., Stratiolaelaps spp., Streptomyces spp., Telenomus spp., Trichogramma spp., Trichoderma spp., or combinations thereof.

[0092] In one subclass of this class or in combination with any other subclass of this class, the plant growth regulator or biostimulant are chosen from a chemical or chemical class chosen from a dioxocyclohexanecarboxylic acid, an indolalcanoic acid, an aliphatic alcohol, a quaternary ammonium, a carbimide, a carboxanilide, a cycloalkene, a cyclohexadione, a cytokinin, a dinitroaniline, an ethylene inhibitor, an ethylene precursor, gibberellin, a pyridazinadione, a sesquiterpenes, a triazole, a benzothiadiazol, nitric oxide, a nitric oxide precursor, methyl salicylate, methyl jasmonate, a protein, a polypeptide, a polyamine, an algae extract, a fulvic acid, a humic acid, a plant growth promoting rhizobacteria, or combinations thereof.

[0093] In one embodiment or in combination with any other embodiment, one or more of the at least one coating layer further comprises a surfactant, a pigment, an antifreeze, a preservative, an antifoaming agent, a suspending agent, a polymer that is different than the binder, a plasticizer, a spreading agent, an emulsifier, a stabilizer, a rheology modifier, a mineral (e.g., a mineral clay), a filler, a disintegrating agent, ora combination thereof.In one embodiment or in combination with any other embodiment, the type of seed is chosen from a vegetable, a fruit, a grain, or a flower. Examples of grain seeds include cereal seeds, pseudograins seeds (e.g., quinoa and chia), pulse seeds, legume seeds, forage, pasture and bale seeds, turf and grass seeds, oil seeds, herbs, aromatic plants, spices and medicinal plant seeds, aquatic seeds, cover up and soil restructuration plant seeds, non-food or non-feed seeds (e.g., tobacco), and fiber crop seeds.

[0094] In one embodiment or in combination with any other embodiment, the sulfopolyester comprises the reaction product of: (a) an acid component, comprising: (i) a diacid or derivative that is chosen from a (C3-8)cycloalkyl dicarboxylic acid or derivative; a (C6)aryl dicarboxylic acid or derivative; a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched; a (C2-3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched; ora combination thereof, (ii) a sulfonated dicarboxylic o o

[0095] o=s=o

[0096]

[0097] R1

[0098] acid or ester of the formula I:1.wherein: R is hydrogen or (C1- 4)alkyl; R

[0099]

[0100] R1isξ-O(C1-4)alkyl orξ-O-M+; and M+is H+, Na+, K+, Li+, or+NH4, and (b) a diol component, comprising an unbranched or branched (C2-i2)alkyl diol, a (C3-8) cycloalky I dimethanol, a (c3-8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci-4)alkyl groups; a compound of formula II: H-(OCH2CH2)n-OH II, wherein n is an integer from 2 to 500; or a combination thereof.

[0101] In one class of this embodiment or in combination with any other class of this embodiment, the sulfopolyester further comprises the reaction product of: (a) an ultraviolet light absorbing component, comprising: (i) an ultraviolet light absorbing monocarboxylic acid oresterf'UVMA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm,wherein the UVMA is a benzoic acid or ester, a cinnamic acid or ester, a 2-benzoylbenzoicacid or ester, a 3,3-diphenylacrylicacid or ester, or combination thereof, wherein each is unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl; (ii) an ultraviolet light absorbing dicarboxylic acid or derivative (“LIVDA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the LIVDA is a naphthalene dicarboxylic acid or derivative, a 1,1 ’-diphenyl dicarboxylic acid or derivative, a phthalic acid or derivative, a 5-amino-isophthalic acid or ester, a 5-(di(Ci-4)alkylamino)isophthalic acid or ester, a 4,4'-methylenebis(3-hydroxy-2-naphthoic acid) or ester, 2-benzylmalonic acid or ester, a 5,5'-methylenebis(2-aminobenzoic acid) or ester; or (iii) a combination thereof, (d) a water dispersing component, comprising a compound of formula III: H-(OCH2CH2)n-O(Ci-4)alkyl, , wherein n is an integer from 2 to 500.

[0102] In one subclass of this class, the compound of formula III is present at from 0.4 to 10 mole% or 0.4 to 8 mole%, or 0.4 to 6 mole%, or 0.4 to 4 mole%, or 0.4 to 2 mole%, or 0.4 to 1 mole%, or 1 to 12 mole%, or 1 to 10 mole%, or 1 to 8 mole%, or 1 to 6 mole%, or 1 to 4 mole%, or 1 to 4 mole%, or 1 to 2 mole%, or 2 to 12 mole%, or 2 to 10 mole%, or 2 to 8 mole%, or 2 to 6 mole%, or 2 to 4 mole%, or 4 to 12 mole%, or 4 to 10 mole%, or 4 to 8 mole%, or 4 to 6 mole%, or 6 to 12 mole%, or 6 to 10 mole%, or 6 to 8 mole%, or 8 to 12 mole%, or 8 to 10 mole%, or 10 to 12 mole%.

[0103] In one subclass of this class, the compound of formula III is the compound of formula Illa: H-(OCH2CH2)n-OCH3, IIIa, wherein n is an integer from 2-500.

[0104] In one class of this embodiment, or in combination with any other embodiment, class, or subclass, the compound of formula III is the compound of formula IIIb:

[0105] H-(OCH2CH2)n-OCH2CH3,

[0106] IIIb

[0107] wherein n is an integer from 2-500.In one embodiment or in combination with any other embodiment, class, or subclass, the sulfopolyester further comprises a branching component, comprising: (i) a branching polycarboxylic acid. In one embodiment or in combination with any other embodiment, class, or subclass, the sulfopolyester further comprises a branching component, comprising: (ii) a branching polyol. In one embodiment or in combination with any other embodiment, class, or subclass, the sulfopolyester further comprises a branching component, comprising: (iii) a branching polyfunctional compound.

[0108] In one embodiment or in combination with any other embodiment, class, or subclass, the branching component is present at from 0.05 to 4 mole %, or from 0.05 to 3.5 mole%, or from 0.05 to 3.0 mole%, or from 0.05 to 2.5 mole%, or from 0.05 to 2.0 mole%, or from 0.05 to 1.5 mole%, or from 0.05 to 1.0 mole%, or from 0.05 to 0.5 mole%, or from 0.05 to 0.25 mole%, or from 0.05 to 0.1 mole%, or from 0.1 to 4 mole %, or from 0.1 to 3.5 mole%, or from 0.1 to 3.0 mole%, or from 0.1 to 2.5 mole%, or from 0.1 to 2.0 mole%, or from 0.1 to 1.5 mole%, or from 0.1 to 1.0 mole%, or from 0.1 to 0.5 mole%, or from 0.1 to 0.25 mole%, 0.3 to 4 mole %, or from 0.3 to 3.5 mole%, or from 0.3 to 3.0 mole%, or from 0.3 to 2.5 mole%, or from 0.3 to 2.0 mole%, or from 0.3 to 1.5 mole%, or from 0.3 to 1.0 mole%, or from 0.3 to 0.5 mole%, 0.5 to 4 mole %, or from 0.5 to 3.5 mole%, or from 0.5 to 3.0 mole%, or from 0.5 to 2.5 mole%, or from 0.5 to 2.0 mole%, or from 0.5 to 1.5 mole%, or from 0.5 to 1.0 mole%, or from 1 to 4 mole %, or from 1 to 3.5 mole%, or from 1 to 3.0 mole%, or from 1 to 2.5 mole%, or from 1 to 2.0 mole%, or from 1 to 1.5 mole%, or 2 to 4 mole %, or from 2 to 3.5 mole%, or from 2 to 3.0 mole%, or from 2 to 2.5 mole%, or from 3 to 4 mole %, or from 3 to 3.5 mole%.

[0109] In one embodiment or in combination with any other embodiment, class, or subclass, the branching polyol is 1,1,1 -trimethylol propane, 1,1,1-trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, sorbitol, or combinations thereof; wherein the branching polycarboxylic acid is trimellitic anhydride, pyromellitic dianhydride, or combinations thereof; and wherein the branching polyfunctional compound is dimethylol propionic acid.In one embodiment or in combination with any other embodiment, class, or subclass, the sulfonated dicarboxylic acid or ester is present from 2.5 to 20 mole%, or from 2.5 to 15 mole%, or from 2.5 to 10 mole%, or from 2.5 to 5 mole%, or from 5 to 20 mole%, or from 5 to 15 mole%, or from 5 to 10 mole%, or from 10 to 20 mole%, or from 10 to 15 mole%, or from 15 to 20 mole%.

[0110] In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is an unbranched or branched (C2-12)alkyl diol or a compound of formula II, wherein n is an integer from 2 to 500; or a combination thereof. In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is an unbranched or branched (C2-12)alkyl diol. In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is a (C3-8)cycloalkyl dimethanol. In one embodiment or in combination with any other embodiment, the diol component is a (c3-8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci-4)alkyl groups. In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is a compound of formula II: H-(OCH2CH2)n-OH , wherein n is an integer from 2 to 500. In one class of this embodiment, n is an integer from 2 to 400, or from 2 to 300, or from 2 to 200, or from 2 to 100, or from 2 to 75, or from 2 to 50, or from 2 to 25, or from 2 to 15, or from 15 to 400, or from 15 to 300, or from 15 to 200, or from 15 to 100, or from 15 to 75, or from 15 to 50, or from 15 to 25, from 25 to 400, or from 25 to 300, or from 25 to 200, or from 25 to 100, or from 25 to 75, or from 25 to 50, or from 50 to 400, or from 50 to 300, or from 50 to 200, or from 50 to 100, or 50 to 75, or 75 to 400, or 75 to 300, or 75 to 200, or 75 to 100, or from 100 to 400, or from 100 to 300, or from 100 to 200, or from 200 to 400, or from 200 to 300, or from 300 to 400. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a benzoic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (C1-4)alkyl. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a cinnamic acid or ester, unsubstituted or substitutedby 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a 2-benzoylbenzoic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a 3,3-diphenylacrylic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alky I.

[0111] In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a naphthalene dicarboxylic acid or derivative,

[0112] In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 1,1 ’-diphenyl dicarboxylic acid or derivative. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a phthalic acid or derivative. In one embodiment or in combination with any other embodiment, the UVDA is a 5-amino-isophthalic acid or ester. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 5-(di(Ci-4)alkylamino)isophthalic acid or ester. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 4,4'-methylenebis(3-hydroxy-2-naphthoic acid) or ester. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is 2-benzylmalonic acid or ester. In one embodiment or in combination with any other embodiment, the UVDA is a 5,5'-methylenebis(2-aminobenzoic acid) or ester.

[0113] In one embodiment or in combination with any other embodiment, class, or subclass, the water dispersing component comprises a compound of formula III: H-(OCH2CH2)n-O(Ci-4)alkyl (III), wherein n is an integer from 2 to 500, or from 2 to 400, or from 2 to 300, or from 2 to 200, or from 2 to 100, or from 2 to 75, or from 2 to 50, or from 2 to 25, or from 2 to 15, or from 15 to 400, or from 15 to 300, or from 15 to 200, or from 15 to 100, or from 15 to 75, or from 15 to 50, or from 15 to 25, from 25 to 400, or from 25 to 300, or from 25 to 200, orfrom 25 to 100, or from 25 to 75, or from 25 to 50, or from 50 to 400, or from 50 to 300, or from 50 to 200, or from 50 to 100, or 50 to 75, or 75 to 400, or 75 to 300, or 75 to 200, or 75 to 100, or from 100 to 400, or from 100 to 300, or from 100 to 200, or from 200 to 400, or from 200 to 300, or from 300 to 400.

[0114] In one class of this embodiment or in combination with any other embodiment, class, or subclass, the (Ci-4)alkyl moiety in the compound of formula III is a methyl, ethyl, propyl, isopropyl, n-butyl, or isobutyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a methyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a ethyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a propyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a n-butyl.

[0115] In one class of this embodiment or in combination with any other class, or subclass, the sulfopolyester is biodegradable.

[0116] In one class of this embodiment or in combination with any other class, or subclass, wherein sulfopolyester exhibits a biodegradability of from 10-100%, or from 10-90%, or from 10-80%, or from 10-70%, or from 10-60%, or from 10-50%, or from 10-40%, or from 20-100%, or from 20-90%, or from 20-80%, or from 20-70%, or from 20-60%, or from 20-50%, or from 20-40%, or from 30-100%, or from 30-90%, or from 30-80%, or from 30-70%, or from 30-60%, or from 30-50%, or from 40-100%, or from 40-90%, or from 40-80%, or from 40-70%, or from 40-60%, or from 40-50%, or from 50-100%, or from 50-90%, or from 50-80%, or from 50-70%, or from 50-60%, or from 60-100%, or from 60-90%, or from 60-80%, or from 60-70%, or from 70-100%, or from 70-90%, or from 70-80%, or from 80-100%, or from 80-90%, at 56 days according to the OECD 301 F test method.

[0117] In one class or or in combination with any other class of this embodiment, class, or subclass, wherein the sulfopolyester exhibits at least 10% biodegradability, or at least 15% biodegradability, or at least 20% biodegradability, or at least 30% biodegradability, or t least 40% biodegradability, at least 45% biodegradability, or at least 50% biodegradability,or at least 55% biodegradability, at least 60% biodegradability, or at least 65% biodegradability, or at least 70% biodegradability, or at least 75% biodegradability, or at least 80% biodegradability, or at least 85% biodegradability, at 56 days according to the OECD 301 F test method.

[0118] Method of Coating Seeds

[0119] The present application discloses a method of preparing a coated seed, comprising: (1) preparing a seed coating composition comprising a sulflopolyester and water; (2) applying the seed coating composition to seeds to prepare coated seeds.

[0120] In one embodiment or in combination with any other embodiment, the sulfopolyester is added as a homogeneous dispersion. In one class of this embodiment, the homogeneous dispersion comprises 5-40 wt% sulfopolyester in water, relative to the total weight of the homogeneous dispersion.

[0121] In one embodiment or in combination with any other embodiment, in the preparing step, the sulfopolyester is added to the seed coating composition as a solid or as an aqueous dispersion. In one class of this embodiment, the sulfopolyester is added to the seed coating composition as a solid. In one class of this embodiment, the sulfopolyester is added to the seed coating composition as an aqueous dispersion.

[0122] In one embodiment or in combination with any other embodiment, in the preparing step further comprises heating the seed coating composition to at least 50°C while stirring for a time sufficient to generate a substantially homogeneous composition.

[0123] In one embodiment or in combination with any other embodiment, in the preparing step, the seed coating composition further comprises an active ingredient. In one class of this embodiment or in combination with any other embodiment, the active ingredient is added before, during, or after the heating in the preparing step.In one embodiment or in combination with any other embodiment, the active ingredient is added before, during, or after the heating in the preparing step.

[0124] In one embodiment or in combination with any other embodiment, during the preparing step, the water is provided at a temperature higher than ambient temperature.

[0125] In one embodiment or in combination with any other embodiment, during the preparing step, wherein one or more of the at least one coating layer further comprises a surfactant, a pigment, an antifreeze, a preservative, an antifoaming agent, a suspending agent, a polymer that is different than the binder, a plasticizer, a spreading agent, an emulsifier, a stabilizer, a rheology modifier, a mineral (e.g., a mineral clay), a filler, a disintegrating agent, or a combination thereof.

[0126] In one embodiment or in combination with any other embodiment, the applying is conducted in a powder applicator, a rotary coater, or a drum coater.

[0127] In one embodiment or in combination with any other embodiment, the applying is performed by pelleting, extrusion coating, spray coating, spread coating, immersing, pouring, soaking, powder coating, drum coating, disc and pan coating, fluidized bed coating, rotary and seed cradle pelletizing and granulation, extrusion orspherization, ancillary conveyer methods, electrostatic coating, and deep coating.

[0128] In one embodiment or in combination with any other embodiment, the method further comprises (3) agitating the coated seeds, after the (2) applying step. The coated seeds can be agitated by any means known to one of skill in the art. The agitating step can be performed to ensure that the coated seeds are evenly coated.

[0129] Active Ingredients and Other Ingredients

[0130] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally further comprise a pigment, an antifreeze, a preservative, an antifoaming agent, asuspending agent, a polymer that is different than the binder, a plasticizer, a spreading agent, an emulsifier, a stabilizer, a rheology modifier, a mineral (e.g., a mineral clay), a filler, a disintegrating agent, or a combination thereof.

[0131] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may optionally include an active ingredient. In one embodiment or in combination with any other embodiment, class, or subclass, the active ingredient is chosen from a microbial organism, a fungicide, an insecticide, a herbicide, a herbicide safener, a nematicide, an acaricide, a plant growth regulator, a biostimulant, a nutrient, an inoculant, a protein, a fertilizer, or a combination thereof.

[0132] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more bactericides as an active ingredient, which are used to mitigate the effects of bacterial damage or predation on agriculture. Useful bactericides include copper hydroxide, copper octanoate, copper oxychloride sulfate, copper sulfate, copper sulfate pentahydrate, kasugamycin, sodium hypochlorite, streptomycin sulfate.

[0133] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more fungicide as an active ingredient, which are used to mitigate the effects of fungi damage or predation on agricultural production. Useful fungicides include 1,2,4-thiadiazole, 2,6-dinitro-aniline, 4-quinolyl-acetate, carboxylic acid, enopyranuronic acid, phthalamic acid, acylalanine, allylamine, mandelic acid amides, cinnamic acid amides, aminocyanoacrylate, amino- pyrazolinone, anilinopyrimidine, anthraquinone, aryloxyquinoline, Bacillus sp. and the produced fungicide lipopeptides, benzene sulfonamide, benzylcarbamate, benzimidazole, benzisothiazole, benzophenone, benzoylpyridine, benzothiadiazole BTH, benzotriazine, butyrolactone, carbamate, carboxamide, cyanoacetamide-oxime, cyanoimidazole, cyano- methylene-thiazolidine, cyclopropane carboxamide, chloronitrile, triphenyltin compounds, dicarboximide, dihydro-dioxazine, dinitrophenyl crotonate, dithiocarbamatesand relative, dithiolane, spirocetal-amine, ethyl phosphonate, ethylamino-thiazol-carboxamide, phenyl-acetamide, phenyl-benzamide, phenyl-oxo-ethyl thiophene amide, phenylpyrrole, phenylurea, phosphonate, phosphorothiolate, phthalimide, furan-carboxamide, guanidine, aromatic hydrocarbon, terpene hydrocarbons and terpene alcohols, hydroxy- (2-amino-) pyrimidine, hydroxy aniline, imidazole, imidazolinone, inorganic (copper), inorganic (sulfur), isobenzofuranone, isothiazolone, isoxazole, maleimide, methoxy-acetamide, a methoxy-acrylate, methoxy-carbamate, Reynoutria sp. extract, a morpholine, a N-phenyl carbamate, N-methoxy-(phenyl-ethyl)-pyrazol- carboxamide, pyrimidine peptidyl nucleoside, oxatin-carboxamide, oxazolidine-dione, oxazolidinone, oximine-acetamide, oximine-acetate, a piperazine, a piperidine, a piperidinyl-thiazole-isoxazoline, a pyrazole-4-carboxamide, pyrazole-5-carboxamide, pyridazinone, pyridine, pyridine- carboxamide, pyridinyl-ethyl benzamide, pyridinylmethyl-benzamide, pyrimidine, pyrimidinamine, pyrimidinone-hydrazone, pyrrolo-quinolinone, polypeptide (lectin), a polysaccharide, a propionamide, a quinazolinone, a quinoxaline, a sulfamoyltriazole, a sulfonamide, a tetrazoyloyloxime, a thiadiazol- carboxamide, thiazol-carboxamide, thiocarbamate, thiophanate, thiophenecarboxamide, toluamide, a triazine, a triazole, triazolintione, triazolobenzo- thiazole, triazole-pyrimidylamine, Trichoderma sp. and produced fungicidal metabolites, trifluoroethylcarbamate, valinamide carbamate, tebuconazole, difenoconazole, fludioxonil, metalaxyl, azoxystrobin, thiabendazole, benodanil, flutolanil, fluopyram, mepronil, isofetamid, fenfuram, oxycarboxin, thifluzamide, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, benzovindiflupyr, or combinations thereof.

[0134] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more herbicides as an active ingredient, which are used to mitigate the effects of unwanted vegetation on agricultural production. Useful herbicides include an acetamide, an arylaminopropionic acid, benzoic acid, chlorocarbonic acid, phenoxycarboxylic acid, phosphinic acid, quinolinecarboxylic acid, an amide,an aryloxyphenoxypropionates, an arylpicolinate, a benzamide, a benzofuran, a benzothiadiazinone, a bipyridylium, a carbamate, a cyclohexanedione, a chloroacetamides, a chloroacetamide, a chloroacetamide, a diphenyl ether, a dinitroaniline, a dinitrophenol, a phenylcarbamate, a phenylpyrazole, a phenylpyrazoline, a phenyl- pyridazine, a phosphoroamidate, a phosphorodithioate, a semicarbazone phthalamate, a glycine, a imidazolinone, a long chain fatty acid inhibitor, an isoxazole, a isoxazolidinone, a N-phenylphthalimide, a nitrile, an organoarsenical, an oxadiazole, an oxazolidinedinone, an oxiacetamide, a pyrazole, a pyrazolium, a pyridazinones, a pyridine, a pyridinecarboxamide, a pyrimidindione, a pyrimidinyl benzoate, a thiopyrimidinyl benzoates, a sulfonylaminocarbonyl-triazolinone, a sulfonylurea, a tetrazolinone, a thiadiazole, a thiocarbamate, a triazine, a triazinone, a triazole, a triazolinone, a triazolocarboxamide, a triazolopyrimidine, a tricetone, a uracil, a urea or combination thereof.

[0135] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more herbicide safeners as an active ingredient, which are used in conjunction with herbicides to protect desirable crops from the potential phytotoxic effects of the herbicides. Useful herbicide safeners include an ammonium acetate, a benoxacor, a cloquintocet, a cloquintocet-acid, a cloquintocet-mexyl, a cyometrinil, a cyprosulfamide, a dichlormid, a dicyclonon, a dietholate, a disodium EDTA, an ethoxylated isodecyl alcohol, a fenchlorazole, a fenchlorazole-ethyl, afenclorim, aflurazole, afluxofenim, afurilazole, a glycine, an isoxadifen, an isoxadifen-ethyl, a mefenpyr, a m efen pyr-di ethyl, a mephenate, a naphthalic anhydride, an oxabetrinil, a piperonyl butoxide, a rapeseed oil, or combination thereof.

[0136] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more insecticides as an active ingredient, which are used to mitigate the effects of insect damage or predation on agricultural production. Useful insecticides include abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,allethrin, alpha-cypermethrin, amitraz, azadirachtin, azamethiphos, azinphos-ethyl, azinphos-methyl, bendiocarb, benfuracarb, bensultap, beta-cyfluthrin, beta-cypermethrin, bifenthrin, bioallethrin, bioresmethrin, bistrifluron, borax, buprofezin, butoxycarboxim, cadusafos, carbaryl, carbofuran, chlorpropham, clothianidin, cyfluthrin, cyhalothrin, cyprmethrin, deltamethrin, diethofencarb, diflubenzuron, dinotefuran, emamectin, endosulfan, fenoxycarb, fenthion, fenvalerate, fipronil, halfenprox, heptachlor, hydramethylnon, imidacloprid, imiprothrin, isoprocarb, lambda cyhalothrin, methamidophos, methiocarb, methomyl, nitenpyram, omethoate, permethrin, pirimicarb, pirimiphos methyl, propoxur, tebufenozide, terpenes, thiamethoxam, thiodicarb, triflumoron, and xylylcarb.

[0137] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more miticides as an active ingredient, which are used to mitigate the effects of mite damage or predation on agricultural production. Useful miticides include antibiotic miticides, carbamate miticides, formamidine miticides, mite growth regulators, organochlorine, permethrin and organophosphate miticides.

[0138] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more microorganisms. Useful microorganisms include one or more bacteria, fungi, mites, nematodes, or combinations thereof. Specific microorganisms include one or more of the following:: the microorganism is Acetobacter spp., Agrobacterium spp., Amblyseius spp., Ampelomyces spp., Aspergillus spp., Aureobasidium spp., Azospirillum spp., Azotobacter spp., Azozpirillum spp., Bacillus spp., Baculovirus spp., Beauveria spp., Bradyrhizobium spp., Candida spp., Cladosporium spp., Coniothyrium spp., Cotesia spp., Cryptolaemus spp., Deladenus spp., Ectomycorrhiza, Endomycorrhiza, Epichlö spp., Funnelifomis spp., Gliocladium spp., Glomus spp., Gluconacetobacter spp., Heterorhabditis spp., Isaria spp., Metarhizium spp., Myrothecium spp., Neoseiulus spp., Orius spp., Paecilomyces spp., Pasteuria spp., Penlcllllum spp., Phytoseiulus spp., Piriformospora spp., Pseudomonas spp., Pseudozyma spp., Purpureocilliumspp., Rhizobium spp., Rhizoglomus spp., Serratia spp., Sinorhizobium spp., Stratiolaelaps spp., Streptomyces spp., Telenomus spp., Trichogramma spp., Trichoderma spp.,, or combinations thereof.

[0139] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more nematicide as an active ingredient, which are used to mitigate the effects of nematode damage or predation on agriculture. Usable nematicides include: a halogenated aliphatic, avermectin, a benzamides, a plant extract, a fluoroalkenyle (-thiother), a methyl isothiocyanate precursor, a benzofuranyl methylcarbamate, a organophosphate or combinations thereof.

[0140] Another category of active ingredient that is included in one embodiment or in combination with any of the mentioned embodiments of the provided agricultural formulations and compositions is fertilizers. Thus, any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more fertilizers as active ingredient(s). Fertilizers are natural or artificial substances that include one or more chemical elements that improve growth and productiveness of plants. Fertilizers enhance the natural fertility of a growth medium (such as soil) or replace the chemical elements taken from the growth medium by previous crops. Modern chemical fertilizers include one or more of the three elements that are most important (main macronutrients) in plant nutrition: nitrogen (N; particularly useful for leaf growth), phosphorus (P; particularly useful for development of roots, flowers, seeds, and fruit), and potassium (K; beneficial for strong stem growth, movement of water in plants, and promotion of flowering and fruiting). Of secondary importance are the elements sulfur (S), magnesium (Mg), and calcium (Ca) (referred to as secondary macronutrients). Optionally, fertilizers may include one or more micronutrients: copper (Cu), iron (Fe), manganese (Mn), molybdenum (Mo), zinc (Zn), boron (B). Of occasional significance are silicon (Si), cobalt (Co), and vanadium (V).

[0141] Nitrogen fertilizers may be obtained from synthetic ammonia (NH3); this chemical compound is used either as a gas or in a water solution, or it isconverted into salts such as ammonium sulfate, ammonium nitrate, and ammonium phosphate. Ammonium can also be made from waste streams, such as packinghouse wastes, treated garbage, sewage, and manure. Phosphorus fertilizers include calcium phosphate derived from phosphate rock or bones. The more soluble superphosphate and triple superphosphate preparations are obtained by the treatment of calcium phosphate with sulfuric and phosphoric acid, respectively. Potassium fertilizers, namely potassium chloride and potassium sulfate, are mined from potash deposits. Mixed fertilizers contain more than one of the three major nutrients — nitrogen, phosphorus, and potassium. Mixed fertilizers can be formulated in myriad ways, which are well known to those of ordinary skill in the art.

[0142] Particularly contemplated herein are fertilizer compositions and formulations intended to be applied as liquids. Examples of liquid fertilizers include one or more of aqueous solutions of ammonia, aqueous solutions of ammonium nitrate, or urea; these concentrated nitrogenous products may be diluted with water to form a concentrated liquid fertilizer (e.g., UAN). Advantages of liquid fertilizer are its more rapid effect and easier coverage. The addition of fertilizer to irrigation water is called “fertigation”. Foliar fertilizers are applied directly to leaves; foliar fertilization is usually used to apply water-soluble nitrogen fertilizers, for instance for high value crops such as fruits. Foliar fertilizers are also gaining popularity with home and hobby gardeners.

[0143] In representative examples, it is desirable to modify the growth rate or development of a desired plant, such as increasing stalk thickness or growth rate of fruits, vegetables through the application of a plant growth regulator. As such, any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more plant growth regulators as active ingredient(s). Compositions, seed coats, and methods can include one or more growth stimulants or plant growth regulators, such as cytokinins up to 4wt.%, gibberellins up to 4wt.%, auxins up to 4wt%, ethylene, abscisic acid up to 4wt.% or combinations thereof. These concentrations when diluted to produce concentrations in the range of 0.01-0.04wt% promote growth. When combined together at a ratio of 0.85:1.0 up to 1:1, plant growth stimulants have similar effects, but the growth stimulants can be used alone or in combination. If the concentrations of the plant growth stimulants are increased 10 to 100 times from what is listed, they can also act as herbicides.

[0144] In representative examples, it is desirable to modify the growth rate of many plants. As such, Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more plant growth regulators as active ingredient(s). Chemicals that are useful to this end include: compounds with quaternary ammonium, phosphonium or sulphonium moieties, flurprimidol, paclobutrazol, uniconazole ancymidol, acylcylcohexanediones (such as trinexapac-ethyl and prohexadione-Ca), daminozide, minoethoxyvinylglycine, brassinolide, forchlorfenuron, hymexazol, thiametoxam), and other plant regulators (such as benzofluor, buminafos, carvone, ciobutide, clofencet, cloxyfonac, cyanamide, cyclanilide, cycloheximide, cyprosulfamide, epocholeone, ethychlozate, fenridazon, heptopargil, holosulf, inabenfide, karetazan, lead arsenate, methasulfocarb, prohexadione, pydanon, sintofen, triapenthenol. Abscisic acid, ancymidol, butralin, carbaryl, chlorphonium, chlorpropham, dikegulac, flumetralin, fluoridamid, fosamine, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, piproctanyl, prohydrojasmon, propham, 2,3,5-tri-iodobenzoic acid), morphactins (chlorfluren, chlorflurenol, dichlorflurenol, flurenol), and aviglycine hydrochloride.

[0145] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more growth stimulator as active ingredient(s), including for instance: Aminooxyacetic acid, rhizobitoxine, and methoxyvinyl glycine, silver thiosulfate, and 2,5-norbornadiene. Brassinolide, forchlorfenuron, hymexazol, 2-amino-6-oxypurine derivatives, indolinone derivates, 3,4-disubstituted maleimide derivatives, and fused azepinone derivatives.Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more surfactants. One of ordinary skill will recognize that there are several agriculturally acceptable surfactants available, which may be useful in one embodiment or in combination with any of the mentioned embodiments of the current disclosure. Surfactants may include one or more of: a-(nonylphenyl)-oo-hydroxypoly(oxy-1,2-ethanediyl); polyethyleneglycol ether; mono(nonyl phenyl)ether; macrogol nonylphenyl ether; polyoxyethylene(n)-nonylphenyl ether; nonylphenyl polyethylene glycol ether; nonylphenoxypolyethoxyethanol; and poly(oxy-1,2 ethanediyl)-a-(nonphyenol)-)-hydroxy, N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyldimethyl-ammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinates, for example cocoacylaminopropyldimethyl-ammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines with in each case 8 to 18 C atoms in the alkyl or acyl group, and cocoacylaminoethyl hydroxyethylcarboxymethyl glycinate, N-alkylglycines, N-alky Ipropionic acids, N-alkylaminobutyric acids, N-alkylimino dipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylamino propionic acids and alkylaminoacetic acids with in each case approximately 8 to 18 C atoms in the alkyl group. Exemplary ampholytic surfactants include N-cocoalkyl amino propionate, coco acyl aminoethyl amino propionate, and C-C-acylsarcosine.

[0146] Non-ionic surfactants include alkoxylates, such as alkoxylated alcohols, alkoxylated fatty acids, for instance ethoxylates and their derivatives including ethoxylated C8 to C24 saturated and unsaturated, linear and branched fatty acids or fatty alcohols, alkoxylated block copolymers, alkoxylated arylalkylphenols, especially ethoxylates and their derivates including alkylphenolethoxylates, alkoxylated amines, alkoxylated oils, fatty esters, especially polyethyleneglycol mono- and diesters of C8 to C24 saturated and unsaturated, linear and branched fatty acids, sorbitan derivatives including esters and ethoxylates, alkylpolyglucosides, and the like.Ionic surfactants include alkylarylsulfonates, alkylarylsulfonic acids, carboxylated alcohol ethoxylates and alkylphenol ethoxylates, carboxylic acids / fatty acids, diphenylsulfonate derivatives, olefin sulfonates, phosphate esters, phosphorous organic derivatives, quaternary surfactants, sulfates and sulfonates of oils and fatty acids, sulfates and sulfonates of ethoxylated alkylphenols, sulfates of exthoxylated alcohols, sulfates of fatty acids, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalene and alkylnaphthalene, sulfonates of petroleum, sulfosuccinamates, alkanolamides, alkoxylated amines, N-acylsarocinates and the like.

[0147] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more antifreeze agents. One of ordinary skill will recognize that there are several agriculturally acceptable antifreeze agents available, which may be useful in one embodiment or in combination with any of the mentioned embodiments of the current disclosure. Antifreeze agents may include: glycols ( / .e. propylene glycol), sorbitol, urea, glycerin, and solvents.

[0148] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more anti-foaming agents. Anti-foamers are useful in order to prevent or reduce foam that can arise during formulation or upon dilution. One of ordinary skill will recognize that there are several agriculturally acceptable anti-foamer agents available, which may be useful in one embodiment or in combination with any of the mentioned embodiments of the current disclosure. Anti-foamer agents may include: 20 polyethylene glycol 8000, polymethylsiloxane, simethicone octanol, and silicone oils and emulsions.

[0149] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more stabilizers (stabilizing agents). One of ordinary skill will recognize that there are several agriculturally acceptable stabilizers available, which may be useful in one embodiment or in combination with any of the mentioned embodiments of the current disclosure. Stabilizers include: xanthan gum, agar,alginic acid, alginate, calcium lactobionate, carrageenan, gellan gum, guar gum, diisopropanolamine, hydroxyethylidene diphosphonic acid, and silver nitrate.

[0150] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more preservatives. One of ordinary skill will recognize that there are several agriculturally acceptable preservatives available, which may be useful in one embodiment or in combination with any of the mentioned embodiments of the current disclosure. Preservatives may include weak acid preservatives such as sorbic acid, lactic acid, benzoic acid, propionic acid, citric acid, acetic acid, or an alkali metal or alkali earth metal salt thereof; inorganic acids such as hydrochloric acid; imidazoles such as imazalil. More generally, a “preservative component” if included in the composition is any molecule that can be used to increase the field or shelf life of the formulation, or a plant or plant part coated with the formulation, including for example fruits, flowers, and vegetables. Exemplary ingredients that can be used as preservative components include parabens including methyl parabens and propyl parabens, sodium benzoate (and other benzoate salts), vanillin, sodium sorbate (and other salts of sorbic acid), vitamin E, tocopherols, a-tocopherol, vitamin E acetate, ethanol, butanol, ethylenediaminetetraacetic acid (EDTA) and all its salts, silicates such as calcium silicate, aluminum magnesium silicate, aluminum calcium silicate, magnesium silicate, aluminum sodium silicate, aluminum potassium silicate, aluminum sodium potassium silicate, other water soluble silicates, and combinations of two or more thereof.

[0151] The preservative component can be included in the formulation at any concentration that is sufficient to increase shelf life. Generally, shelf life refers to the amount of time that a particular formulation, or plant or plant part, can be maintained in saleable condition. Similarly, the field life refers to the amount of time that a plant, or plant part can be maintained in a field and still allow for the plant part to be harvested in saleable condition.One of ordinary skill in the art will be able to determine the appropriate concentration of preservative component(s), for instance desired by producing test formulations having varying amounts of preservative components, optionally applying them to the plant or plant part, and measuring the self-life or field life of the formulation, or of the plant or plant part. Exemplary concentrations of preservative components in the compositions include from 0.001wt% to 10.5wt%, from 0.01wt% to 10wt%, from 0.02wt% to 9wt%, from 0.05wt% to 8wt%, from 0.07wt% to 7wt%, from 0.10wt% to 6wt%, and from 0.15wt% to 5wt%. The preservative component if included in the composition may in addition increase the shelf-life of the formulation during storage, shipping, exhibiting for sale and handling that may happen prior to use of the product by the end user for the uses outlined herein for the compositions detailed in the current document.

[0152] Any of the seed coating compositions, coated seeds, and method comprising sulfopolyesters described herein may also optionally include one or more compounds that influence or regulate pH, for instance, buffers, acidifiers, basifiers, and so forth. One of ordinary skill will recognize that there are several agriculturally acceptable pH regulating compounds available, which may be useful in one embodiment or in combination with any of the mentioned embodiments of the current disclosure. Examples of pH regulators include: ethanolamine, phosphoric acid, triethanolamine, acetic acid, diethylamine, monoethylamine, and monoisopropylamine

[0153] In one embodiment or in combination with any other embodiment, class, or subclass, the active ingredient is an agrochemical active ingredient.

[0154] Sulfopolyesters

[0155] The sulfopolyester described herein is a water-dispersible sulfopolyester. The water-dispersible sulfopolyester can be any sulfopolyester including at least one sulfomonomer residue. In one embodiment or in combination with any of the mentioned embodiments, the sulfomonomer residue comprises a salt of a sulfoisophthalate moiety derived, for example, from sodiosulfoisophthalic acid (5-SSIPA) or esters thereof. Thesulfoisophthalate moiety can also be derived from other metallic sulfoisophthalic acids and esters thereof. For example, the associated metal M is a mono-valent metal, such as Na+, Li+, or K+.

[0156] o O ’

[0157]

[0158] SO3⊖M

[0159] Salt of a sulfoisophthalate moiety

[0160] Moreover, the salt of the sulfoisophthalate moiety can also be derived from non-metallic sulfoisophthalic acids and esters thereof. As an example, the metal sulfonate group can be replaced by an ammonium sulfonate group, such as a tertiary or quaternary ammonium cation, for example ammonium, hydrazonium, N-methyl pyridinium, methylammonium, butylammonium, diethylammonium, triethylammonium, tetraethylammonium, and benzyltrimethylammonium.

[0161] In addition to the sulfoisophthalate moiety, the sulfopolyester can include the residues of one or more of a glycol monomer, a dicarboxylic acid monomer, and / or a diamine monomer. Examples of sulfopolyester includes sulfopolyester, sulfopolyamide, or sulfopolyesteramide.

[0162] In one embodiment or in combination with any of the mentioned embodiments, the sulfopolyester can be a linear polymer having an average molecular weight (MW) of at least 2 kDa. In one embodiment or in combination with any of the mentioned embodiments, the sulfopolyester has an average MW of 2-20 kDa, 4-18 kDa, 5-15 kDa, 5-12 kDa, or 7-10 kDa. Additionally, the sulfopolyester can have a Tgof at least 30°C. Furthermore, the sulfopolyester can have a Tgin the range of from 30°C to 120°C, 35°C to 100°C, 40°C to 90°C, 45°C to 80°C, and 50°C to 70°C.

[0163] The water-dispersible sulfopolyester used in accordance with the present disclosure is prepared from monomer residues comprising dicarboxylic acid monomer residues, sulfomonomer residues, and diol monomer residues. The sulfomonomer may be a dicarboxylic acid, a diol, or hydroxycarboxylic acid.Thus, the term “monomer residue”, as used herein, means a residue of a dicarboxylic acid, a diol, or a hydroxycarboxylic acid. A “repeating unit” or “repeat unit”, as used herein, means an organic structure having 2 monomer residues bonded through a carbonyloxy group. The sulfopolyesters for use with the present disclosure contain substantially equal molar proportions of acid residues (100mole%) and diol residues (100mole%) which react in substantially equal proportions such that the total moles of repeating units are equal to 100mole%.

[0164] The sulfopolyesters are high molecular weight amorphous polyesters commonly dispersed directly in water without the need to incorporate organic co-solvents, surfactants, or amines. Sulfopolyesters differ chiefly by their chemical makeup (i.e. they are composed of 5-sodiosulfoisophthalic acid (5-SSIPA) and various combinations of other materials, for example: terephthalic acid (TPA), isophthalic acid (IPA), 1,4-cyclohexane dicarboxylic acid (1,4-CHDA), ethylene glycol (EG), diethylene glycol (DEG), triethylene glycol (TEG), 1,4-cyclohexanedimethanol (CHDM) and / or neopentyl glycol (NPG). The MW of the sulfopolyester described herein is 2 kDa to 15 kDa. The temperature where a glassy polymer becomes rubbery on heating, and vice versa upon cooling, is known as the ‘glass transition temperature (Tg). Hence, the various sulfopolyester polymers have different average Tgvalues. Sulfopolyesters are solid to semi-solid polymers and require warm to hot water with sufficient mixing time to prepare concentrated dispersions.

[0165] In general, sulfopolyester dispersions, and particularly aqueous dispersions of sulfopolyesters, will have a pH that is neutral to mildly acidic, for instance in the range of 5-7.5. Specific example sulfopolyester s will have a pH of between 5.5 and 7, or between 5.8 and 6.8, or between 6.0 and 6.6, or between 5.8 and 6.5.

[0166] The mole percentages provided in the present disclosure may be based on the total moles of acid residues, the total moles of diol residues, or the total moles of repeating units. For example, a sulfopolyester containing 30mole% of a sulfomonomer, which may be a dicarboxylic acid, a diol, or hydroxycarboxylicacid, based on the total repeating units, means that the sulfopolyester contains 30mole% sulfomonomer out of a total of 100mole% repeating units. Thus, there are 30 moles of sulfomonomer residues among every 100 moles of repeating units. Similarly, a sulfopolyester containing 30mole% of a dicarboxylic acid sulfomonomer including a sulfoisophthalic moiety, based on the total acid residues, means the sulfopolyester contains 30mole% sulfomonomer out of a total of 100mole% acid residues. Thus, in this latter case, there are 30 moles of sulfomonomer residues among every 100 moles of acid residues.

[0167] The sulfopolyesters described herein have an inherent viscosity, abbreviated hereinafter as “Ih. V.”, of at least 0.1 dL / g, for instance at least 0.2, at least 0.3 dL / g, or at least 0.4 dL / g, and at most 0.5 dL / g, measured in a 60 / 40 parts by weight solution of phenol / tetrachloroethane solvent at 25°C and at a concentration of 0.5 g of sulfopolyester in 100ml of solvent. The term “polyester”, as used herein, encompasses both “homopolyesters” and “copolyesters” and means a synthetic polymer prepared by the polycondensation of difunctional carboxylic acids with difunctional hydroxyl compound. As used herein, the term “sulfopolyester” means any polyester comprising a sulfomonomer including a sulfoisophthalic moiety. Typically, the difunctional carboxylic acid is a dicarboxylic acid and the difunctional hydroxyl compound is a dihydric alcohol such as, for example glycols and diols. Alternatively, sulfopolyester contains hydroxy acid monomers, for example, p-hydroxybenzoic acid, and the difunctional hydroxyl compound may be an aromatic nucleus bearing 2 hydroxy substituents such as, for example, hydroquinone. The term “residue”, as used herein, means any organic structure incorporated into the polymer through a polycondensation reaction involving the corresponding monomer. Thus, the dicarboxylic acid residue may be derived from a dicarboxylic acid monomer or its associated acid halides, esters, salts, anhydrides, or mixtures thereof. As used herein, therefore, the term dicarboxylic acid is intended to include dicarboxylic acids and any derivative of a dicarboxylic acid, including its associated acid halides, esters, half-esters, salts, half-salts, anhydrides, mixed anhydrides, or mixtures thereof, useful in apolycondensation process with a diol to make a high molecular weight polyester.

[0168] The sulfopolyester of the present disclosure includes one or more dicarboxylic acid residues. Depending on the type and concentration of the sulfomonomer, the dicarboxylic acid residue may comprise from 60 to 100mole% of the acid residues. Other examples of concentration ranges of dicarboxylic acid residues are from 60mole% to 95mole%, and 70mole% to 95mole%. Examples of dicarboxylic acids that may be used include aliphatic dicarboxylic acids, alicyclic dicarboxylic acids, aromatic dicarboxylic acids, or mixtures of two or more of these acids. Thus, suitable dicarboxylic acids include succinic; glutaric; adipic; azelaic; sebacic; fumaric; maleic; itaconic; 1,3-cyclohexanedicarboxylic; 1,4 cyclohexanedicarboxylic; diglycolic; 2,5-norbornanedicarboxylic; phthalic; terephthalic; 1,4-naphthalenedicarboxylic; 2,6-naphthalenedicarboxylic; diphenic; 4,4'-oxydibenzoic; 4,4'-sulfonyidibenzoic; and isophthalic. Example dicarboxylic acid residues are isophthalic, terephthalic, and 1,4-cyclohexanedicarboxylic acids, or if diesters are used, dimethyl terephthalate, dimethyl isophthalate, and dimethyl-1,4-cyclohexane-dicarboxylate with the residues of isophthalic and terephthalic acid being exemplary. The dicarboxylic acid methyl ester is a specific example embodiment; it is also acceptable to include higher order alkyl esters, such as ethyl, propyl, isopropyl, butyl, and so forth. In addition, aromatic esters, particularly phenyl, also may be employed.

[0169] The sulfopolyester includes 4 to 40mole%, based on the total repeating units, of residues of at least one sulfomonomer having two functional groups and one or more sulfonate groups attached to an aromatic or cycloaliphatic ring wherein the functional groups are hydroxyl, carboxyl, ora combination thereof. Additional examples of concentration ranges for the sulfomonomer residues are 4 to 35mole%, 8 to 30mole%, and 8 to 25mole%, based on the total repeating units. The sulfomonomer may be a dicarboxylic acid or ester thereof containing a sulfonate group, a diol containing a sulfonate group, or a hydroxy acid containing a sulfonate group. The term “sulfonate” refers to the anion of asulfonic acid having the structure “-SO3 ‘ and the term “sulfonate salt” is the salt of a sulfonic acid having the structure “-SO3M” wherein M is the cation of the sulfonate salt. The cation of the sulfonate salt may be a metal ion such as Li+, Na+, K+, and the like. Alternatively, the cation of the sulfonate salt may be non-metallic such as a nitrogenous base as described, for example, in U. S. Patent No. 4,304,901. Nitrogen-based cations are derived from nitrogen-containing bases, which may be aliphatic, cycloaliphatic, or aromatic compounds. Examples of such nitrogen containing bases include ammonia, dimethylethanolamine, diethanolamine, triethanolamine, pyridine, morpholine, and piperidine. Because monomers containing the nitrogen-based sulfonate salts typically are not thermally stable at conditions required to make the polymers in the melt, the method of this disclosure for preparing sulfopolyesters containing nitrogen-based sulfonate salt groups is to disperse, dissipate, or dissolve the polymer containing the required amount of sulfonate group in the form of its alkali metal salt in water and then exchange the alkali metal cation fora nitrogen-based cation.

[0170] When a monovalent alkali metal ion is used as the cation of the sulfonate salt, the resulting sulfopolyester is completely dispersible in water with the rate of dispersion dependent on the content of sulfomonomer in the polymer, temperature of the water, surface area / thickness of the sulfopolyester, and so forth. When a divalent metal ion is used, the resulting sulfopolyesters are not readily dispersed by cold water but are more easily dispersed by hot water. Utilization of more than one counterion within a single polymer composition is possible and may offer a means to tailor or fine-tune the water-responsivity of the resulting article of manufacture. Examples of sulfomonomer residues include monomer residues where the sulfonate salt group is attached to an aromatic or alicyclic ring of an aromatic dicarboxylic acid or residues thereof, such as, for example, the rings of benzene; naphthalene; diphenyl; oxydiphenyl; sulfonyldiphenyl; and methylenediphenyl or cycloaliphatic rings, such as, for example, cyclohexyl; cyclopentyl; cyclobutyl; cycloheptyl; and cyclooctyl. Other examples of sulfomonomer residues which may be used in the presentdisclosure are the metal sulfonate salt of sulfophthalic acid, sulfoterephthalic acid, sulfoisophthalic acid, or combinations thereof. Other examples of sulfomonomers which may be used are 5-sodiosulfoisophthalicacid and esters thereof. If the sulfomonomer residue is from 5-sodiosulfoisophthalic acid, typical sulfomonomer concentration ranges are 4 to 35mole%, 8 to 30mole%, and about 8 to 25mole%, based on the total moles of acid residues.

[0171] The sulfomonomers used in the preparation of the sulfopolyesters are known compounds and may be prepared using methods well known in the art. For example, sulfomonomers in which the sulfonate group is attached to an aromatic ring may be prepared by sulfonating the aromatic compound with oleum to obtain the corresponding sulfonic acid and followed by reaction with a metal oxide or base, for example, sodium acetate, to prepare the sulfonate salt. Procedures for preparation of various sulfomonomers are described, for example, in U. S. Patents No. 3,779,993; 3,018,272; and 3,528,947.

[0172] It is also possible to prepare the polyester using, for example, a sodium sulfonate salt, and ion-exchange methods to replace the sodium with a different ion, such as zinc, when the polymer is in the dispersed form. This type of ion exchange procedure is generally superior to preparing the polymer with divalent salts insofar as the sodium salts are usually more soluble in the polymer reactant melt-phase.

[0173] The sulfopolyester includes one or more diol residues which may include aliphatic, alicyclic, and / or aralkyl glycols. Examples include ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycols, and polyalkylene glycols. Other suitable glycols include cycloaliphatic glycols having 6 to 20 carbon atoms and aliphatic glycols having 3 to 20 carbon atoms. Specific examples of such glycols are ethylene glycol, propylene glycol, 1,3-propanediol, 2,4-dimethyl-2-ethylhexane-1,3-diol, 2, 2-dimethyl-1,3-propanediol, 2-ethyl-2-butyl-1,3-propanediol, 2-ethyl-2-isobutyl-1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, diethanol, 2,2,4-trimethyl-1,6-hexanedio-1 thiodiethanol, 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, 2,2,4,4-tetra-methyl-1,3-cyclobutanediol, and p-xylylenediol. The sulfopolyester can also comprise a mixture of glycols.

[0174] Diols also includes polyfunctional alcohols (polyols). Examples of polyols include neopentyl glycol; butylene glycol; 1,4-butanediol, hexylene glycol; 1,6-hexanediol; the polyglycols such as diethylene glycol or triethylene glycol and the like; the triols such as glycerine, trimetylol ethane, trimethylol propane and the like; and other higher functional alcohols such as pentaerythritol, sorbitol, mannitol, and the like.

[0175] The diol residues may include from 25mole% to 100mole%, based on the total diol residues, residues of a poly(ethylene glycol) having a structure H-(OCH2-CH2)n-OH

[0176] wherein n is an integer in the range of 2 to 500. Non-limiting examples of lower molecular weight polyethylene glycols, e.g., wherein n is from 2 to 6, are diethylene glycol, triethylene glycol, and tetraethylene glycol. Of these lower molecular weight glycols, diethylene, and triethylene glycol are exemplars. Higher molecular weight polyethylene glycols (abbreviated herein as “PEG”), wherein n is from 7 to 500, include the commercially available products known under the designation CARBOWAX®, a product of Dow Chemical Company (formerly Union Carbide). Typically, PEGs are used in combination with other diols such as, for example, diethylene glycol or ethylene glycol. Based on the values of n, which range from greater than 6 to 500, the molecular weight may range from greater than 300 to 22,000 g / mol. The molecular weight and the mole% are inversely proportional to each other; specifically, as the molecular weight is increased, the mole% will be decreased in order to achieve a designated degree of hydrophilicity. For example, it is illustrative of this concept to consider that a PEG having a molecular weight of 1000 may constitute up to 10mole% of the total diol, while a PEG having a molecular weight of 10,000 would typically be incorporated at a level of less than 1 mole% of the total diol.

[0177] Certain dimer, trimer, and tetramer diols may be formed in situ due to side reactions that may be controlled by varying the process conditions. For example, varying amounts of diethylene, triethylene, and tetraethylene glycolsmay be formed from ethylene glycol from an acid-catalyzed dehydration reaction which occurs readily when the polycondensation reaction is carried out under acidic conditions. The presence of buffer solutions, well-known to those skilled in the art, may be added to the reaction mixture to retard these side reactions. Additional compositional latitude is possible, however, if the buffer is omitted and the dimerization, trimerization, and tetramerization reactions are allowed to proceed.

[0178] The sulfopolyester of the present disclosure may include from 0 to 25mole%, based on the total repeating units, of residues of a branching monomer having 3 or more functional groups wherein the functional groups are hydroxyl, carboxyl, or a combination thereof. Non-limiting examples of branching monomers are 1,1,1 -trimethylol propane, 1,1,1 -trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, sorbitol, trimellitic anhydride, pyromellitic dianhydride, dimethylol propionic acid, or combinations thereof. Further examples of branching monomer concentration ranges are from 0 to 20mole% and from 0 to 10mole%. The presence of a branching monomer may result in a number of possible benefits to the sulfopolyester of the present disclosure such as the ability to tailor rheological, solubility, and tensile properties. For example, at a constant molecular weight, a branched sulfopolyester, compared to a linear analog, will also have a greater concentration of end groups that may facilitate post-polymerization crosslinking reactions. At high concentrations of branching agent, however, the sulfopolyester may be prone to gelation.

[0179] In one embodiment or in combination with any of the mentioned embodiments, the sulfopolyesters described herein comprise the following structural formula (Formula A):

[0180] HO-G-A-G-A i -G-A-G-A-G-A i -G-OH

[0181] SO3Na SO3Na

[0182] Formula A

[0183] wherein A is a dicarboxylic acid repeat unit and G is a glycol repeat unit. Examples of dicarboxylic acid repeat units A include but are not limited toterephthalic acid, isophthalic acid and / or 1,4-cyclohexane dicarboxylic acid (1,4-CHDA). Examples of glycol repeat units G include but are not limited to ethylene glycol (EG), Diethylene glycol (DEG), triethylene glycol (TEG), neopentyl glycol (NPG), and / or 1,4-cyclohexane dimethanol (CHDM). The following are illustrative monomer residues:

[0184]

[0185] OH Ethylene Glycol Diethylene Glycol Triethylene Glycol

[0186] o

[0187]

[0188] 1,4-Cyclohexane Dimethanol Neopentyl Glycol O Terephthalic Acid

[0189]

[0190] n 1,4-Cyclohexane

[0191] Isophthalic Acid O Dicarboxylic Acid

[0192] As an example, the sulfopolyester can include the following structural formula:

[0193]

[0194] In one embodiment or in combination with any of the mentioned embodiments he sulfopolyesters useful in the present disclosure have a glass transition temperature, abbreviated herein as “Tg”, of at least 25°C as measured on the dry polymer using standard techniques, such as differential scanning calorimetry (“DSC”), well known to persons skilled in the art. The Tgmeasurements of the sulfopolyesters of the present disclosure are conducted using a “dry polymer”, that is, a polymer sample in which adventitious or absorbed water is driven off by heating to polymer to a temperature of 200°C and allowing the sample to return to room temperature. Typically, the sulfopolyester is dried in the DSC apparatus by conducting a first thermal scan in which the sample is heated to a temperature above the water vaporizationtemperature, holding the sample at that temperature until the vaporization of the water absorbed in the polymer is complete (as indicated by a large, broad endotherm), cooling the sample to room temperature, and then conducting a second thermal scan to obtain the Tgmeasurement. Further examples of glass transition temperatures exhibited by the sulfopolyester are at least 30°C, at least 35°C, at least 40°C, at least 50°C, at least 60°C, at least 65°C, at least 80°C, and at least 90°C, and in addition or in the alternative, up to 100°C, or up to 110°C or up to 120°C. Although other Tg’s are possible, typical glass transition temperatures of the dry sulfopolyesters of the present disclosure are 30°C, 48°C, 55°C, 65°C, 70°C, 75°C, 85°C, and 90°C.

[0195] In one embodiment or in combination with any of the mentioned embodiments, the sulfopolyester comprises:

[0196] (i) residues of one or more dicarboxylic acids;

[0197] (ii) 2 to 20mole%, based on the total moles of diacid or diol residues, of residues of at least one sulfomonomer having two functional groups and one or more sulfonate groups attached to an aromatic or cycloaliphatic ring wherein the functional groups are hydroxyl, carboxyl, ora combination thereof;

[0198] (iii) one or more diol residues wherein at least 25mole%, based on the total diol residues, is a polyethylene glycol) having a structure H-(OCH2-CH2)n-OH

[0199] wherein n is an integer in the range of 2 to 500; and

[0200] (iv) 0 to 25mole%, based on the total repeating units, of residues of a branching monomer having three or more functional groups wherein the functional groups are hydroxyl, carboxyl, ora combination thereof.

[0201] In one embodiment or in combination with any of the mentioned embodiments, the sulfopolyester has a Tgof at least 25°C and comprises:

[0202] (i) residues of one or more dicarboxylic acids;

[0203] (ii) 4 to 40mole%, based on the total repeating units, of residues of at least one sulfomonomer having two functional groups and one or more metal sulfonate groups attached to an aromatic or cycloaliphatic ring wherein the functional groups are hydroxyl, carboxyl, ora combination thereof;(iii) one or more diol residues wherein at least 20mole%, based on the total diol residues, is a polyethylene glycol) having a structure H-(OCH2-CH2)n-OH

[0204] wherein n is an integer in the range of 2 to 500;

[0205] (iv) 0 to 25mole%, based on the total repeating units, of residues of a branching monomer having three or more functional groups wherein the functional groups are hydroxyl, carboxyl, ora combination thereof.

[0206] In one embodiment or in combination with any other embodiment, the sulfopolyester comprises the reaction product of: (a) an acid component, comprising: (i) a diacid or derivative that is chosen from a (C3-8)cycloalkyl dicarboxylic acid or derivative; a (C6)aryl dicarboxylic acid or derivative; a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched; a (C2-3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched; ora combination thereof, (ii) a sulfonated dicarboxylic o o

[0207] o=s=o

[0208]

[0209] R1

[0210] acid or ester of the formula I:1.wherein: R is hydrogen or (Ci- 4)alkyl; R

[0211]

[0212] R1isξ-O(C1-4)alkyl orξ-O-M+; and M+is H+, Na+, K+, Li+, or+NH4, and (b) a diol component, comprising an unbranched or branched (C2-i2)alkyl diol, a (C3-8) cycloalky I dimethanol, a (c3-8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci-4)alkyl groups; a compound of formula II: H-(OCH2CH2)n-OH , wherein n is an integer from 2 to 500; or a combination thereof.

[0213] In one class of this embodiment or in combination with any other class of this embodiment, the sulfopolyester further comprises the reaction product of: (a) an ultraviolet light absorbing component, comprising: (i) an ultraviolet light absorbing monocarboxylic acid oresterf'UVMA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm,wherein the UVMA is a benzoic acid or ester, a cinnamic acid or ester, a 2-benzoylbenzoicacid or ester, a 3,3-diphenylacrylicacid or ester, or combination thereof, wherein each is unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl; (ii) an ultraviolet light absorbing dicarboxylic acid or derivative (“LIVDA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the LIVDA is a naphthalene dicarboxylic acid or derivative, a 1,1 ’-diphenyl dicarboxylic acid or derivative, a phthalic acid or derivative, a 5-amino-isophthalic acid or ester, a 5-(di(Ci-4)alkylamino)isophthalic acid or ester, a 4,4'-methylenebis(3-hydroxy-2-naphthoic acid) or ester, 2-benzylmalonic acid or ester, a 5,5'-methylenebis(2-aminobenzoic acid) or ester; or (iii) a combination thereof, (d) a water dispersing component, comprising a compound of formula III: H-(OCH2CH2)n-O(Ci-4)alkyl, , wherein n is an integer from 2 to 500.

[0214] In one subclass of this class, the compound of formula III is present at from 0.4 to 10 mole% or 0.4 to 8 mole%, or 0.4 to 6 mole%, or 0.4 to 4 mole%, or 0.4 to 2 mole%, or 0.4 to 1 mole%, or 1 to 12 mole%, or 1 to 10 mole%, or 1 to 8 mole%, or 1 to 6 mole%, or 1 to 4 mole%, or 1 to 4 mole%, or 1 to 2 mole%, or 2 to 12 mole%, or 2 to 10 mole%, or 2 to 8 mole%, or 2 to 6 mole%, or 2 to 4 mole%, or 4 to 12 mole%, or 4 to 10 mole%, or 4 to 8 mole%, or 4 to 6 mole%, or 6 to 12 mole%, or 6 to 10 mole%, or 6 to 8 mole%, or 8 to 12 mole%, or 8 to 10 mole%, or 10 to 12 mole%.

[0215] In one subclass of this class, the compound of formula III is the compound of formula Illa: H-(OCH2CH2)n-OCH3, IIIa, wherein n is an integer from 2-500.

[0216] In one class of this embodiment, or in combination with any other embodiment, class, or subclass, the compound of formula III is the compound of formula IIIb:

[0217] H-(OCH2CH2)n-OCH2CH3,

[0218] IIIb

[0219] wherein n is an integer from 2-500.In one embodiment or in combination with any other embodiment, class, or subclass, the sulfopolyester further comprises a branching component, comprising: (i) a branching polycarboxylic acid. In one embodiment or in combination with any other embodiment, class, or subclass, the sulfopolyester further comprises a branching component, comprising: (ii) a branching polyol. In one embodiment or in combination with any other embodiment, class, or subclass, the sulfopolyester further comprises a branching component, comprising: (iii) a branching polyfunctional compound.

[0220] In one embodiment or in combination with any other embodiment, class, or subclass, the branching component is present at from 0.05 to 4 mole %, or from 0.05 to 3.5 mole%, or from 0.05 to 3.0 mole%, or from 0.05 to 2.5 mole%, or from 0.05 to 2.0 mole%, or from 0.05 to 1.5 mole%, or from 0.05 to 1.0 mole%, or from 0.05 to 0.5 mole%, or from 0.05 to 0.25 mole%, or from 0.05 to 0.1 mole%, or from 0.1 to 4 mole %, or from 0.1 to 3.5 mole%, or from 0.1 to 3.0 mole%, or from 0.1 to 2.5 mole%, or from 0.1 to 2.0 mole%, or from 0.1 to 1.5 mole%, or from 0.1 to 1.0 mole%, or from 0.1 to 0.5 mole%, or from 0.1 to 0.25 mole%, 0.3 to 4 mole %, or from 0.3 to 3.5 mole%, or from 0.3 to 3.0 mole%, or from 0.3 to 2.5 mole%, or from 0.3 to 2.0 mole%, or from 0.3 to 1.5 mole%, or from 0.3 to 1.0 mole%, or from 0.3 to 0.5 mole%, 0.5 to 4 mole %, or from 0.5 to 3.5 mole%, or from 0.5 to 3.0 mole%, or from 0.5 to 2.5 mole%, or from 0.5 to 2.0 mole%, or from 0.5 to 1.5 mole%, or from 0.5 to 1.0 mole%, or from 1 to 4 mole %, or from 1 to 3.5 mole%, or from 1 to 3.0 mole%, or from 1 to 2.5 mole%, or from 1 to 2.0 mole%, or from 1 to 1.5 mole%, or 2 to 4 mole %, or from 2 to 3.5 mole%, or from 2 to 3.0 mole%, or from 2 to 2.5 mole%, or from 3 to 4 mole %, or from 3 to 3.5 mole%.

[0221] In one embodiment or in combination with any other embodiment, class, or subclass, the branching polyol is 1,1,1 -trimethylol propane, 1,1,1-trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, sorbitol, or combinations thereof; wherein the branching polycarboxylic acid is trimellitic anhydride, pyromellitic dianhydride, or combinations thereof; and wherein the branching polyfunctional compound is dimethylol propionic acid.In one embodiment or in combination with any other embodiment, class, or subclass, the sulfonated dicarboxylic acid or ester is present from 2.5 to 20 mole%, or from 2.5 to 15 mole%, or from 2.5 to 10 mole%, or from 2.5 to 5 mole%, or from 5 to 20 mole%, or from 5 to 15 mole%, or from 5 to 10 mole%, or from 10 to 20 mole%, or from 10 to 15 mole%, or from 15 to 20 mole%.

[0222] In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is an unbranched or branched (C2-12)alkyl diol or a compound of formula II, wherein n is an integer from 2 to 500; or a combination thereof. In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is an unbranched or branched (C2-12)alkyl diol. In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is a (C3-8)cycloalkyl dimethanol. In one embodiment or in combination with any other embodiment, the diol component is a (c3-8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci-4)alkyl groups. In one embodiment or in combination with any other embodiment, class, or subclass, the diol component is a compound of formula II: H-(OCH2CH2)n-OH , wherein n is an integer from 2 to 500. In one class of this embodiment, n is an integer from 2 to 400, or from 2 to 300, or from 2 to 200, or from 2 to 100, or from 2 to 75, or from 2 to 50, or from 2 to 25, or from 2 to 15, or from 15 to 400, or from 15 to 300, or from 15 to 200, or from 15 to 100, or from 15 to 75, or from 15 to 50, or from 15 to 25, from 25 to 400, or from 25 to 300, or from 25 to 200, or from 25 to 100, or from 25 to 75, or from 25 to 50, or from 50 to 400, or from 50 to 300, or from 50 to 200, or from 50 to 100, or 50 to 75, or 75 to 400, or 75 to 300, or 75 to 200, or 75 to 100, or from 100 to 400, or from 100 to 300, or from 100 to 200, or from 200 to 400, or from 200 to 300, or from 300 to 400. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a benzoic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (C1-4)alkyl. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a cinnamic acid or ester, unsubstituted or substitutedby 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a 2-benzoylbenzoic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl. In one embodiment or in combination with any other embodiment, class, or subclass, the UVMA is a 3,3-diphenylacrylic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alky I.

[0223] In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a naphthalene dicarboxylic acid or derivative,

[0224] In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 1,1 ’-diphenyl dicarboxylic acid or derivative. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a phthalic acid or derivative. In one embodiment or in combination with any other embodiment, the UVDA is a 5-amino-isophthalic acid or ester. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 5-(di(Ci-4)alkylamino)isophthalic acid or ester. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is a 4,4'-methylenebis(3-hydroxy-2-naphthoic acid) or ester. In one embodiment or in combination with any other embodiment, class, or subclass, the UVDA is 2-benzylmalonic acid or ester. In one embodiment or in combination with any other embodiment, the UVDA is a 5,5'-methylenebis(2-aminobenzoic acid) or ester.

[0225] In one embodiment or in combination with any other embodiment, class, or subclass, the water dispersing component comprises a compound of formula III: H-(OCH2CH2)n-O(Ci-4)alkyl (III), wherein n is an integer from 2 to 500, or from 2 to 400, or from 2 to 300, or from 2 to 200, or from 2 to 100, or from 2 to 75, or from 2 to 50, or from 2 to 25, or from 2 to 15, or from 15 to 400, or from 15 to 300, or from 15 to 200, or from 15 to 100, or from 15 to 75, or from 15 to 50, or from 15 to 25, from 25 to 400, or from 25 to 300, or from 25 to 200, orfrom 25 to 100, or from 25 to 75, or from 25 to 50, or from 50 to 400, or from 50 to 300, or from 50 to 200, or from 50 to 100, or 50 to 75, or 75 to 400, or 75 to 300, or 75 to 200, or 75 to 100, or from 100 to 400, or from 100 to 300, or from 100 to 200, or from 200 to 400, or from 200 to 300, or from 300 to 400.

[0226] In one class of this embodiment or in combination with any other embodiment, class, or subclass, the (Ci-4)alkyl moiety in the compound of formula III is a methyl, ethyl, propyl, isopropyl, n-butyl, or isobutyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a methyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a ethyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a propyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a n-butyl.

[0227] In one class of this embodiment or in combination with any other class, or subclass, the sulfopolyester is biodegradable.

[0228] In one class of this embodiment or in combination with any other class, or subclass, wherein sulfopolyester exhibits a biodegradability of from 10-100%, or from 10-90%, or from 10-80%, or from 10-70%, or from 10-60%, or from 10-50%, or from 10-40%, or from 20-100%, or from 20-90%, or from 20-80%, or from 20-70%, or from 20-60%, or from 20-50%, or from 20-40%, or from 30-100%, or from 30-90%, or from 30-80%, or from 30-70%, or from 30-60%, or from 30-50%, or from 40-100%, or from 40-90%, or from 40-80%, or from 40-70%, or from 40-60%, or from 40-50%, or from 50-100%, or from 50-90%, or from 50-80%, or from 50-70%, or from 50-60%, or from 60-100%, or from 60-90%, or from 60-80%, or from 60-70%, or from 70-100%, or from 70-90%, or from 70-80%, or from 80-100%, or from 80-90%, at 56 days according to the OECD 301 F test method.

[0229] In one class or or in combination with any other class of this embodiment, class, or subclass, wherein the sulfopolyester exhibits at least 10% biodegradability, or at least 15% biodegradability, or at least 20% biodegradability, or at least 30% biodegradability, or t least 40% biodegradability, at least 45% biodegradability, or at least 50% biodegradability,or at least 55% biodegradability, at least 60% biodegradability, or at least 65% biodegradability, or at least 70% biodegradability, or at least 75% biodegradability, or at least 80% biodegradability, or at least 85% biodegradability, at 56 days according to the OECD 301 F test method.

[0230] The foregoing description of the exemplary embodiments of the present invention has been provided for the purposes of illustration and description. It is not intended to be exhaustive or to limit the invention to the precise forms disclosed. Obviously, many modifications and variations will be apparent to practitioners skilled in the art. The embodiments were chosen and described in order to best explain the principles of the invention and its practical applications, thereby enabling others skilled in the art to understand the invention for various embodiments and with the various modifications as are suited to the particular use contemplated. It is intended that the scope of the invention be defined by the following claims and their equivalents.

[0231] EXPERIMENTAL SECTION

[0232] Abbreviations

[0233] AQ-48 is 30 wt% Eastman AQTM48 aqueous dispersion (Eastman AQ™ 48 is available from Eastman Chemical Company); Eastek 1000 is 30wt% Eastman Eastek™ 1000 polymer aqueous dispersion (Eastman Eastek™ 1000 is available from Eastman Chemical Company); AQ-16 is Example 16 of PCT Appln. PCT / US2024 / 053368; SACP is 44wt% Atlox™ SemSera (styrene / acrylic copolymer) aqueous dispersion (Altox™ Semsara is available from Croda); BWE is 30wt% NutureYield® S 2010 aqueous dispersion (NutureYield® S 2010 is available from Michelman); VA-EAA is 50wt% Pericoat VA 100 (vinyl acetate / ethylene-acrylic copolymer) aqueous dispersion (Pericoat VA 100 is available from Textilchemie); PVPS is 26wt% Adsee ST4 (polyvinylpyrrolidone / starch copolymer) aqueous dispersion (Adsee NT4 is available from Nouryon); N / T is no treatment; PDSE is polydimethylsiloxaneemulsion; POEA is polyoxyethylene C9-C11 alcohol; Preserv is preservative(s); ProG is propylene glycol; Glyc is glycerol;

[0234] General Procedure for the Preparation of AQ-48 and AQ-16

[0235] A stock dispersion of the polymer in water was prepared by suspending pellets of the polymer in water. The resulting suspension was heated with stirring to 80°C and held at 80°C for 30 min then cooled to room temperature to provide a stock dispersion, which was used without further purification. The appropriate amounts of solids were adjusted to provide the stock dispersions at the desired weight percentage. AQ-48 and AQ-16 are prepared as 30wt% aqueous dispersions.

[0236] Concentrate For Seed Coating

[0237] Concentrates for coating seeds were prepared as shown in Table 1, incorporating various active ingredients (e.g., azoxystrobin, difenoconazole), various binders, and other formulation ingredients. The formulations were prepared using a standard procedure.

[0238] A pre-mill base was prepared by mixing 255.1 g of active ingredient, 30.0 g of pigment, 25.0 g of dispersant agent, 5.0 g of wetting agent, 1.82 g of antifoam, 22.73 g of antifreeze in 227.25 g of water using an IKA ministar 40 control overhead stirrer. The pre-mill base was transferred and milled in a bead mill (EMI Mills, Laboratory Mini Mill M250) at 3000 rpm with full recirculation. The particle size distribution was determined at time intervals, and the milling process ran until the particle size distribution reduced to D50 < 5 μm and D90 < 10 μm. After this step, the milled material was collected, and its density was determined and used to determine the required amounts of all products needed to finalize the formulation. Next, the suspending agent, preservative, the remainder antifreeze, polymeric binder, and remainder water up to 100% were added and stirred for 10 min until homogeneous, forming the flowable concentrate formulation for seed treatment.Table 1. Composition of seed coating formulations. Each formulation was diluted with water (q.s. 100wt%).

[0239] Surfactant Ex Binder Antifreeze Preserv Antifoam Suspending Active Pigment # (wt%) Dispersant Wetting (wt%) (wt%) (wt%) Agent (wt%)

[0240] (wt%) Agent (wt%) Sodium

[0241]

[0242] Difenoconazole Red Lignosulfonate pi Proxel™ Xanthan gum 1 (25) gment - (0.84) / Acrylic POEA (0.3) ProG (6) GXL (0.25) PDSE (0.3) (0.17) / Attapulgite

[0243] (10) copolymer clay (1.33)

[0244] solution (1.05)

[0245] Sodium

[0246] Red Lignosulfonate Xanthan gum

[0247] 2 Difenoconazole pigment AQ-48 (0.84) / Acrylic POEA (0.3) ProG (6) Proxel™

[0248] (25)

[0249] (10) (3.8) copolymer GXL (0.25) PDSE (0.3) (0.17) / Attapulgite

[0250] clay (1.33)

[0251] solution (1.05)

[0252] Sodium

[0253] 3 Difenoconazole Red AQ-48 Lignosulfonate Proxel™ Xanthan gum

[0254] pigment (084) / Acrylic POEA (03) ProG (6) PDSE (03) (0 17) / Attapulgite

[0255] (25) (7.5) copo GXL (0.25)

[0256] (10) lymer clay (1.33)

[0257] solution (1.05)

[0258] Sodium

[0259] Difenoconazole Red AQ-48 Lignosulfonate Proxel™ Xanthan gum

[0260] pigment (0.84) / Acrylic POEA (0.3) ProG (6) PDSE (0.3) (0.17) / Attapulgite 4 (25)

[0261] (10) (11 3) copolymer GXL (0.25) clay (1.33)

[0262] solution (1.05)

[0263] Sodium

[0264] Difenoconazole Red AQ-48 Lignosulfonate Proxel™ Xanthan gum

[0265] 5 (25) pigment (0.84) / Acrylic POEA (0.3) ProG (6)

[0266] (10) (15) copolymer GXL (0.25) PDSE (0.3) (0.17) / Attapulgite

[0267] clay (1.33)

[0268] solution (1.05)

[0269] Sodium

[0270] Red Lignosulfonate Xanthan gum Difenoconazole pigment AQ-48 (0.87) / Acrylic - ProG (6.32) Proxel™ PDSE

[0271] 6 (2592) (0.15) / Attapulgite

[0272] (9.07) (6.8) copolymer GXL (0.23) (0.18) clay (1.39)

[0273] solution (1.1)

[0274] Red Sodium Xanthan gum Difenoconazole SACP Proxel™ PDSE pigment Lignosulfonate ProG (6.32) (0.15) / Attapulgite 7 (2592) GXL (0.23) (0.18) (6.8) (907) (087) / Acrylic clay (1 39)

[0275]

[0276] Ex A Binder Surfactant Antifreeze Preserv Antifoam Suspending # ctive Pigment (wt%) Dispersant Wetting

[0277] (wt%) Agent (wt%) (wt%) (wt%) (wt%) Agent (wt%)

[0278] copolymer

[0279] solution (1.1)

[0280] Sodium Difenoconazole Red Lignosulfonate Xanthan gum pigment BWE (0.87) / Acrylic - ProG (6.32) Proxel™ PDSE (0.15) / Attapulgite 8 (25.92) (68) GXL (023) (018) (9.07) copolymer clay (1.39) sol

[0281]

[0282] ution (1.1) Azoxystrobin Red Tristyrylphenol

[0283] pig AQ-48 Proxel™ment phosphate, POEA (05) Glyc (45) PDSE (02) Xanthan gum (05) 9 (25.5) (1.5) GXL (0.1) amine salt (2.5) (3)

[0284] Red Tri styrylphenol Azoxystrobin AQ-48 Proxel™ pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 10 (25.5) GXL (0.1) (3) amine salt (2.5) (3)

[0285] Red Tristyrylphenol Azoxystrobin AQ-48 Proxel™ pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 11 (25.5) GXL (0.1) (5) amine salt (2.5) (3)

[0286] Red Tri styrylphenol

[0287] Azoxystrobin AQ-48 Proxel™ pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 12 (25.5) GXL (0.1) (7.5) amine salt (2.5) (3)

[0288] Red Tri styrylphenol Azoxystrobin AQ-48 Proxel™

[0289] pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 13 (25.5) GXL (0.1) (10) amine salt (2.5) (3)

[0290] Red Tristyrylphenol Azoxystrobin Proxel™ VA- pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 14 (25.5) EAA (3) GXL (0.1) amine salt (2.5) (3)

[0291] Red Tri styrylphenol

[0292] Azoxystrobin PVPS Proxel™ pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 15 (25.5) (5.7) GXL (0.1) amine salt (2.5) (3)

[0293] Red Tristyrylphenol Azoxystrobin SACP Proxel™ pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 16 (25.5) GXL (0.1) (3.4) amine salt (2.5) (3)

[0294] Red Tri styrylphenol Azoxystrobin AQ-16 Proxel™ Pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 17 (25.5) GXL (0.1) (1-5) amine salt (2.5) (3)

[0295] Red Tri styrylphenol

[0296] Azoxystrobin AQ-16 Proxel™ Pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 18 (25.5) GXL (0.1) (5) amine salt (2.5) _ (3) _

[0297]

[0298] Surfactant

[0299] Ex Active Pigment Binder Antifreeze Preserv Antifoam Suspending

[0300] # (wt%) Dispersant Wetting (wt%) (wt%) (wt%) Agent (wt%)

[0301] (wt%) Agent (wt%)

[0302] Azoxystrobin Red AQ-16 Tristyrylphenol Proxel™ Pigment phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 19 (25.5) (15) GXL (0.1)

[0303] (3 amine salt (2.5)) Red Tri styrylphenol Azoxystrobin Proxel™ Pigment - phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 20 (255) GXL (01) amine salt (2.5) (3)

[0304]

[0305] Red Eastek Tristyrylphenol Azoxystrobin Proxel™

[0306] Pigment 1000 phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 21 (25.5) GXL (0.1) (1 5) amine salt (25) (3)

[0307] Red Eastek Tri styrylphenol Azoxystrobin Proxel™ Pigment 1000 phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 22 (25.5) GXL (0.1) amine salt (2.5) (3) (3)

[0308] Red Eastek Tristyrylphenol Azoxystrobin Proxel™

[0309] Pigment 1000 phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 23 (25.5) GXL (0.1) amine salt (2.5) (3) (5)

[0310] Red Eastek Tristyrylphenol Azoxystrobin Proxel™ Pigment 1000 phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 24 (25.5) GXL (0.1) amine salt (2.5) (7.5) (3)

[0311] Red Eastek Tri styrylphenol Azoxystrobin Proxel™ Pigment 1000 phosphate, POEA (0.5) Glyc (4.5) PDSE (0.2) Xanthan gum (0.5) 25 (255) GXL (01)

[0312] amine salt (2.5) _ (3) _

[0313]

[0314] (10)Treatment of Corn Seeds with Ex 1-5

[0315] The flowable concentrates were diluted to 50% with water and applied at a rate of 2.0 mL slurry per 100 g of corn seeds using spinning disk equipment. Post-application, the treated seeds were immediately tested for fresh flowability, allowed to dry for 24 hours, tested for dry flowability, and subsequently stored in sealed plastic containers.

[0316] Flowability was assessed using a lab-scale seed flowability tester (FlowTek seed flow meter), which measures the weight of seeds that flow through a funnel per second. Dust-off measurements were performed using a Heubach device, adhering to the standard Euroseeds reference method settings, an industrial standard method for dust-off assessment (30 rpm, 10 min, 20 L / min).

[0317] Table 2. Performance results of corn seeds treated with Ex 1-5.

[0318] Dust-off

[0319] Flowability in

[0320] Ex# (g / 100 kg

[0321] seed drill (s)

[0322] seed)

[0323] N / T NA 43

[0324] 1 5.8 52

[0325] 2 2.4 50

[0326] 3 1.8 50

[0327] 4 1.6 49

[0328]

[0329] 5 1.5 49

[0330] Performance Results of Corn Seeds treated with Ex 6-8

[0331] Flowable concentrate for seed treatment formulations were prepared as detailed in Table 3, incorporating difenoconazole as the active model ingredient and a red pigment. These formulations, each containing different seed binder types, were prepared using a standard procedure familiar to an experienced operator.

[0332] The seed treatment formulations (5.65 g of formulation per kg of seed) were applied to corn seeds via spinning disk equipment. Post-application, the treated seeds were dried for 24 hours and subsequently stored in sealed plastic containers.Flowability testing was conducted using a custom-made seed drill, designed by a seed drill manufacturer to simulate a tractor-driven drill operating at a forward speed of 0.3 km / h and a seed application rate of 210 kg / ha. This test measured the rate at which a known weight of seed passed through the drill.

[0333] Dust-off measurements were performed using a Heubach device, adhering to the standard ESTA settings, an industrial standard method for dust-off assessment (30 rpm, 10 min, 20 L / min).

[0334] Germination tests were carried out in triplicate, with 30 seeds placed on moisturized paper sheets, rolled, and stored in plastic bags in the dark at 20°C. The germination stages were evaluated after 5 and 7 days, categorized as follows: Stage 1 - No germination; Stage 2-3 - Root and sprout visible; Stage 4-5 - Multiple roots and large sprout visible.

[0335] Table 3.

[0336] Germination Day 5 Germination Day 7 Dust-off Flowability (No. of seeds) (No. of seeds) Ex

[0337] (mg / 100 in seed drill

[0338] #

[0339] g seed) (s) Stag Stag Stag Stag Stag Stag

[0340] e e e e e 1 e 1

[0341] 2-3 4-5 2-3 4-5 N / T n / a 42 6 43 41 6 12 72 6 1 49 4 44 42 4 5 81 7 1.9 50 4 50 36 2 7 81

[0342]

[0343] 8 3.8 49 7 53 30 5 7 78

[0344] Performance Results of Corn Seeds Treated with Ex 9-25.

[0345] The seed coating formulations were diluted to 50% with water and applied at a rate of 2.0 mL slurry per 100 g of corn seeds using spinning disk equipment. Post-application, the treated seeds were either immediately tested for fresh flowability or dried for 24 hours and subsequently stored in sealed plastic containers.

[0346] Flowability was assessed using a lab-scale seed flowability tester (FlowTek), which measures the weight of seeds that flow through a funnel persecond. Dust-off measurements were performed using a Heubach device, adhering to the standard ESTA settings, an industrial standard method for dust-off assessment (30 rpm, 10 min, 20 L / min).

[0347] Table 4.

[0348] Flowability Flowability Dust-off

[0349] Ex# (Initially) (24h dried) g / 100k

[0350] (s) (s) kernels

[0351] 9 284 389 0.32

[0352] 10 276 376 0.43

[0353] 11 274 372 0.28

[0354] 12 276 390 0.25

[0355] 13 282 396 0.28

[0356] 14 283 331 0.24

[0357] 15 280 348 0.44

[0358] 16 284 360 0.34

[0359] 17 277 364 0.29

[0360] 18 280 357 0.25

[0361] 19 253 342 0.09

[0362] 20 285 346 0.49

[0363] 21 282 358 0.53

[0364] 22 274 363 0.37

[0365] 23 272 370 0.22

[0366] 24 281 387 0.25

[0367]

[0368] 25 272 392 0.14

[0369] Biocompatibility of the sulfopolyester with living microorganisms.

[0370] Varying concentrations (20wt%, 15wt%, 10wt%, 7.5wt%, 5wt%, 2wt%, 1wt%, and 0.5wt%) of a sulfopolyester compound (Eastman™ AQ-48 as a 20wt% aqueous dispersion) were incorporated into Mueller Hinton (MH) agar. A serial dilution of the sulfopolyester was prepared in an appropriate nutrient medium and subsequently dispensed into Petri dishes, which were allowed to solidify. Specific microorganisms were inoculated onto the prepared agar plates following a standardized procedure known to those skilled in the art. Control groups included negative controls (MH agar devoid of sulfopolyester) and positive controls (MH agar inoculated with microorganisms) to ensure the validity of comparative results.In one embodiment, Bacillus subtilis was inoculated onto the prepared plates; in another embodiment, Bradyrhizobium japonicum was utilized; and in yet another embodiment, Trichoderma harzianum was employed. The reduction in colony-forming units (cfu) was quantified by measuring optical density at 595 nm to determine the Minimum Inhibitory Concentration (MIC) value.

[0371] This assay evaluates the ability of microorganisms to proliferate in a nutrient-rich medium maintained at optimal growth temperatures when combined with a specified concentration of sulfopolyester, thereby assessing their biocompatibility. The effect of the sulfopolyester on the microbial growth phase was determined through endpoint measurements of cfu growth on the agar plates. Reference protocols, including those described by Cardoso-Gustavson et al. (2020), were employed to define the experimental procedures. The biocompatibility of chemical substances with bacteria and fungi is typically assessed by monitoring microbial growth kinetics in a culture medium containing various concentrations of the test substance. The substance must be thoroughly homogenized with the culture medium prior to microbial inoculation.

[0372] Literature, such as Basamma et al. (2020), describes biocompatibility primarily through two parameters: Maximum Tolerance Concentration (MTC) and Minimum Inhibitory Concentration (MIC). MTC is characterized by less than a 50% reduction in cfu relative to the control, whereas MIC is characterized by more than a 90% reduction in cfu relative to the control.

[0373] In all conducted tests, the MIC and MTC values for the three microorganisms against the sulfopolyester were surprisingly significantly higher than the typical concentration of this material in a seed coating formulation, thereby indicating biocompatibility with but not limited the tested organisms.Table 5. Antibacterial activity of Eastman™ AQ-48.

[0374] Microorganism MIC MBC

[0375] Bacillus subtilis >2% >2%

[0376] Bradyrhizobium

[0377] 2% 2%

[0378] japonicum

[0379] Trichoderma

[0380] >2% >2%

[0381]

[0382] harzianum

[0383] Biocompatibility of sulfopolyester with Various Bacteria

[0384] Shelf-life testing, also referred to as challenge testing, was conducted to demonstrate the viability of microorganisms over an extended period when combined with the sulfopolyester. This assay provides an indication of the survival rate of microorganisms within the sulfopolyester formulation during prolonged storage. A substantial number of viable microorganisms after the specified period suggests that the formulation can be stored for an extended duration before application in the field.

[0385] The procedure involved preparing a dilution of the sulfopolyester in a saline solution, followed by inoculating each tube with an equivalent quantity of the microorganism according to a standardized procedure known to those skilled in the art. The survival rate of the microorganisms was monitored over a predetermined period and compared to a positive control, defined as a saline solution inoculated with the microorganism but without sulfopolyester. The tests in saline solution provide a reliable indication of the survival of the microorganism in contact with the sulfopolyester, thus assessing its biocompatibility with the tested microorganism, similar to the concept described by Purwanto et al. 2017.

[0386] In one embodiment, Bacillus subtilis as inoculated onto the prepared plates; in another embodiment, Bradyrhizobium japonicum was utilized; and in yet another embodiment, Trichoderma harzianum was employed. The concentration in colony-forming units (log cfu / mL) was quantified overtime.

[0387] The data results for Bacillus subtilis and Bradyrhizobium japonicum indicate that the sulfopolyester with 4% active polymer content after one yearsurprisingly exhibited a drop of log 0.57 cfu / mL, which is not significantly different from the positive control. The sulfopolyester is thus not responsible for the drop of approximately log 0.5 cfu / mL, as this minor decrease is observed in both the positive control and the highest sulfopolyester concentration tube. A similar conclusion can be made for Trichoderma harzianum, where the sulfopolyester is not responsible for the decrease in viability.

[0388] It can be concluded that a combination of the sulfopolyester with, but not limited to, the tested organisms will surprisingly remain viable for at least one year on the shelf, and that any potential decrease in the quantity of microorganisms is not attributable to the sulfopolyester.

[0389] Table 6. Biocompatibility of the sulfopolyester (wt% solid content) with Bacillus subtilis over time (in days).

[0390] Concentration in colony-forming units (log cfu / mL) Sample 0 2 6 8 13 21 27 64 92 116 179 270 300 362 Neg.

[0391] control 0.0 0.0 00 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Posit.

[0392] Control 8.1 6.2 63 6.4 6.6 6.7 6.6 6.4 6.6 6.4 6.6 6.6 6.5 6.5 4.0wt% 8.0 5.8 5.9 5.7 5.8 6.0 5.9 6.0 6.0 6.2 5.9 6.0 6.0 6.1 3.0wt% 7.9 5.9 5.8 5.8 5.7 5.9 5.8 6.1 6.1 6.2 5.9 6.0 6.1 6.2 2.0wt% 7.9 5.9 5.9 5.8 5.8 6.0 5.7 5.9 6.1 6.2 6.0 6.1 6.2 6.2 1.5wt% 7.9 5.7 5.9 5.9 5.9 6.1 5.9 6.1 6.1 5.9 6.0 6.2 6.1 6.1 1.0wt% 8.0 5.8 5.8 5.8 5.9 6.1 6.0 6.1 6.1 6.0 6.0 6.1 6.0 6.1 0.4wt% 7.9 5.8 5.8 6.0 5.9 5.9 5.9 6.1 6.2 6.1 6.1 6.1 6.2 6.0 0.2% 8.0 6.0 6.1 6.0 5.9 6.0 6.1 6.0 6.3 6.2 6.3 6.3 6.2 6.1

[0393]

[0394] 0.1% 8.1 5.8 6.2 6.0 6.0 6.3 6.1 6.2 6.3 6.3 6.2 6.2 6.3 6.3Table 7. Biocompatibility of the sulfopolyester (wt% solid content) with Trichoderma harzianum over time (in days).

[0395] Concentration in colony-forming units (log cfu / mL) Sample

[0396] 0 2 6 21 28 62 89 120 199 269 299 365 Neg.

[0397] control 0 0 0 0 0 0 0 0 0 0 0 0 Posit.

[0398] Control 6.2 5.9 6.1 6.0 5.8 6.21 6.1 6 5.6 5.2 5.6 5.8 4.0wt% 6.2 6.1 6.0 6.2 6.0 5.9 6.0 6.1 5.7 5.3 5.6 5.8 3.0wt% 6.2 6.2 6.3 6.2 6.2 6.0 6.1 6.2 5.6 5.4 5.7 5.6 2.0wt% 6.1 6.1 6.1 6.2 6.0 6.0 6.1 6.0 5.6 5.3 5.5 5.6 1.5wt% 6.2 6.1 6.1 6.3 6.1 6.2 6.1 5.8 5.4 5.3 5.6 5.7 1.0wt% 6.3 6.0 6.3 6.2 6.1 6.1 6.2 5.8 5.4 5.3 5.5 5.5 0.4wt% 6.3 5.9 6.2 6.4 6.1 6.1 6.2 5.9 5.7 5.2 5.4 5.4 0.2wt% 6.2 6.1 6.2 6.3 6.2 5.9 6.1 6.1 5.4 5.3 5.2 5.3 0.1wt% 6.2 6.1 6.0 6.2 6.07 5.7 5.9 6.1 5.6 5.2 5.4 5.5

[0399]

[0400] Table 8. Biocompatibility of the sulfopolyester (wt% solid content) with Bradyrhizobium japonica over time (in days).

[0401] Concentration in colony-forming units (log cfu / mL) Sample

[0402] 0 1 8 15 22 29 62 92 120 183 251 304 359 Neg. 0 0 0 0 0 0 0 0 0 0 0 0 0 control

[0403] Posit.

[0404] control 8.4 8.6 8.9 8.7 8.4 8.4 8.4 8.5 8.0 7.8 8.0 8.0 7.9 4.0wt% 8.4 8.3 8.3 8.2 8.0 8.2 8.1 8.3 7.8 7.5 7.6 8.0 7.8 3.0wt% 8.4 8.3 8.3 8.2 8.0 8.0 8.1 8.2 7.6 7.3 7.5 7.8 7.7 2.0wt% 8.4 8.5 8.3 8.3 8.0 8.0 8.0 8.0 7.9 7.4 7.8 7.8 7.7 1.5wt% 8.5 8.4 8.3 8.4 7.9 8.1 8.0 8.0 7.7 7.4 7.2 7.4 7.6 1.0wt% 8.4 8.4 8.2 8.2 7.9 8.1 8.0 8.1 7.7 7.4 7.6 7.8 7.5

[0405] 1

[0406] 0.4wt% 8.5 8.3 8.2 8.2 8.1 8.0 8.0 8.1 7.8 7.5 7.6 7.6 7.6 0.2wt% 8.3 8.4 8.2 8.4 8.2 8.1 8.1 8.2 8.0 7.6 8.0 7.9 7.9

[0407]

[0408] 0.1wt% 8.3 8.4 8.3 8.2 8.1 8.1 8.1 8.2 7.7 7.6 7.8 7.8 7.6

Claims

CLAIMSWhat is claimed is:

1. A seed coating composition, comprising:(1) a binder comprising a sulfopolyester; and(2) water,wherein the binder is present at from 0.5 to 20 weight percent (“wt%”),wherein the wt% of each component in the seed coating composition is based on the total weight of the seed coating composition.

2. The composition of claim 1, further comprising (3) a surfactant, wherein the surfactant is present at from 0.1 to 20 wt%.

3. The composition of any one of claims 1-2, wherein the binder comprises 20 to 100wt%, or 50 to 100 wt% of the sulfopolyester, based on the total weight of the binder.

4. The composition of any one of claims 1-3, further comprising an active ingredient.

5. A coated seed comprising:(1) a seed; and(2) at least one coating layer,wherein the at least one coating layer comprises:(i) a first coating layer comprising a binder comprising a sulfopolyester.

6. The coated seed of claim 5, wherein the first coating layer is disposed on the surface of the seed.

7. The coated seed of any one of claims 5-6, wherein the at least one coating layer further comprises a second coating layer.

8. The coated seed of claim 7, wherein the second coating layer is disposed on the surface of the seed, below the first layer, or above the first layer.

9. The coated seed of any one of claims 5-8, wherein the one or more of the at least one coating layer further comprises an active ingredient 10. The coated seed of any one of claims 5-9, wherein the type of seed is chosen from a vegetable, a fruit, a grain, or a flower.

11. Use of the seed coating composition of any one of claims 1 -4 to coat seeds.

12. A method of preparing a coated seed, comprising:(1) preparing a seed coating composition comprising a sulfopolyester and water;(2) applying the seed coating composition to seeds to prepare coated seeds.

13. The method of claim 12, wherein during preparing step, the seed coating composition is prepared by combining the sulfopolyester with water, wherein the sulfopolyester is provided as a homogeneous aqueous dispersion or a as a solid.

14. The method of claim 13, wherein the homogeneous aqueous dispersion comprises 5-40 wt% sulfopolyester in water, relative to the total weight of the homogeneous aqueous dispersion.

15. The method of any one of claims 12-14, wherein the preparing step further comprises heating the seed coating composition to at least 50°C while stirring for a time sufficient to generate a substantially homogeneous composition.

16. The method of any one of claims 12-15, wherein the seed coating composition further comprises an active ingredient.

17. The method of claim 16, wherein the active ingredient is added before, during, or after the heating in the preparing step.

18. The method of any one of claims 12-17, wherein during the preparing step, the water is provided at a temperature higher than ambient temperature.

19. The method of any one of claims 12-18, wherein the applying is conducted in a powder applicator, a rotary coater, or a drum coater.

20. The method of any one of claims 12-19, wherein the applying is performed by pelleting, extrusion coating, spray coating, spread coating, immersing, pouring, soaking, powder coating, drum coating, disc and pan coating, fluidized bed coating, rotary and seed cradle pelletizing and granulation, extrusion or spherization, ancillary conveyer methods, electrostatic coating, and deep coating.

21. The method of any one of claims 12-20, further comprising (3) agitating the coated seeds, after the (2) applying step.

22. The composition, use, coated seed, or method of any one of claims 1-21, wherein the sulfopolyester comprises the reaction product of (a) an acid component, comprising:(i) a diacid or derivative that is chosen from a (C3-8)cycloalkyl dicarboxylic acid or derivative; a (Cs)aryl dicarboxylic acid or derivative; a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched; a (C2-3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched; or a combination thereof,(ii) a sulfonated dicarboxylic acid or ester of the formula I:o oo=s=oR1iwherein:R is hydrogen or (Ci-4)alkyl;R1 is bO(C1.4)alkylorO M.anc|M+is H+, Na+, K+, Li+, or+NH4, and(b) a diol component, comprising an unbranched or branched (C2-12)alkyl diol, a (C3-8)cycloalkyl dimethanol, a (c3-8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci-4)alkyl groups; a compound offormula II: H-(OCH2CH2)n-OH II, wherein n is an integer from 2 to 500; or a combination thereof.

23. The composition, use, coated seed, or method of any one of claims 1-22, wherein the sulfopolyester further comprises the reaction product of (a) an ultraviolet light absorbing component, comprising:(i) an ultraviolet light absorbing monocarboxylic acid or ester (“LIVMA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm,wherein the LIVMA is a benzoic acid or ester, a cinnamic acid or ester, a 2-benzoylbenzoic acid or ester, a 3,3-diphenylacrylic acid or ester, or combination thereof,wherein each is unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci- 4)alkoxy, cyano, or (Ci-4)alkyl;(ii) an ultraviolet light absorbing dicarboxylic acid or derivative (“UVDA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm,wherein the UVDA is a naphthalene dicarboxylic acid or derivative, a 1, T-diphenyl dicarboxylic acid or derivative, a phthalic acid or derivative, a 5-amino-isophthalic acid or ester, a 5-(di(Ci- 4)alkylamino)isophthalic acid or ester, a 4,4'-methylenebis(3- hydroxy-2-naphthoic acid) or ester, 2-benzylmalonic acid or ester, a 5,5'-methylenebis(2-aminobenzoic acid) or ester; or (iii) a combination thereof,(b) a water dispersing component, comprising a compound of formula III:H-(OCH2CH2)n-O(Ci-4)alkyl,IIIwherein n is an integer from 2 to 500.

24. The composition, use, coated seed, or method of any one of claims 1-23, wherein sulfopolyester is dispersible in water at 70°C to form adispersion having at least 5 wt% of the sulfopolyester based on the total weight of the dispersion,wherein the sulfopolyester has a glass transition temperature (“Tg”) that is in the range of from -60 to 70°C and a melting point (“Tm”) that is in the range of from 45 to 80°C or 35 to 75°C.

25. The composition, use, coated seed, or method of any one of claims 1-24, wherein sulfopolyester exhibits a biodegradability of from 10-100%, or from 10-90%, or from 10-80%, or from 10-70%, or from 10-60%, or from 10-50%, or from 10-40%, or from 20-100%, or from 20-90%, or from 20-80%, or from 20-70%, or from 20-60%, or from 20-50%, or from 20-40%, or from 30-100%, or from 30-90%, or from 30-80%, or from 30-70%, or from 30-60%, or from 30-50%, or from 40-100%, or from 40-90%, or from 40-80%, or from 40-70%, or from 40-60%, or from 40-50%, or from 50-100%, or from 50-90%, or from 50-80%, or from 50-70%, or from 50-60%, or from 60-100%, or from 60-90%, or from 60-80%, or from 60-70%, or from 70-100%, or from 70-90%, or from 70-80%, or from 80-100%, or from 80-90%, at 56 days according to the OECD 301 F test method.

26. The composition, use, coated seed, or method of any one of claims 1-25, wherein the active ingredient is chosen from a microbial organism, a fungicide, an insecticide, a herbicide, a herbicide safener, a nematicide, an acaricide, a plant growth regulator, a biostimulant, a nutrient, an inoculant, a protein, an amino acid, an oligosaccharide, a peptide, an hormone, a fertilizer, or a combination thereof.

27. The composition, use, coated seed, or method of any one of claims 1-26, wherein the seed coating composition or the at least one coating layer further comprises a pigment, an antifreeze, a preservative, an antifoaming agent, a suspending agent, a polymer that is different than the binder, a plasticizer, a spreading agent, an emulsifier, a stabilizer, a rheology modifier, a mineral, a filler, a disintegrating agent, ora combination thereof.

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