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WO2025080464A1 - Aqueous seed treatment compositions and coatings therefrom - Google Patents

Aqueous seed treatment compositions and coatings therefrom Download PDF

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Publication number
WO2025080464A1
WO2025080464A1 PCT/US2024/049398 US2024049398W WO2025080464A1 WO 2025080464 A1 WO2025080464 A1 WO 2025080464A1 US 2024049398 W US2024049398 W US 2024049398W WO 2025080464 A1 WO2025080464 A1 WO 2025080464A1
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WIPO (PCT)
Prior art keywords
seed
aqueous
polyester
treatment composition
seed treatment
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Pending
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PCT/US2024/049398
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French (fr)
Inventor
Xiangtao MENG
David L. Malotky
Yi Fan
Sia ZAMANI
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Dow Global Technologies LLC
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Dow Global Technologies LLC
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Publication of WO2025080464A1 publication Critical patent/WO2025080464A1/en
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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01CPLANTING; SOWING; FERTILISING
    • A01C1/00Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/06Coating or dressing seed
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10Macromolecular compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00Arthropodicides
    • A01P7/04Insecticides

Definitions

  • acrylic latex has dominated the seed coating composition market along with other chemistries such as polyolefin dispersion, polyurethane dispersion, cellulose, polyvinyl alcohol and polyvinyl acetates. But there are issues with such conventional FFAs.
  • the present disclosure provides for aqueous seed treatment compositions for forming coatings on agricultural seeds, which address the above identified shortcomings in the art.
  • the aqueous seed treatment composition for forming the coating on the agricultural seed includes a polyester aqueous dispersion formed with a mixture that includes a polyester, a dispersing agent and water; an agriculturally active compound; and water.
  • the aqueous seed treatment composition can further include other additives, such as one or more of a pigment, a dispersing agent for the active ingredient, a defoamer, rheology modifiers and cosolvents, as discussed herein,
  • the aqueous seed treatment composition for forming the coating on the agricultural seed of the present disclosure do not contain microplastics.
  • the aqueous seed treatment compositions of the present disclosure are microplastics-free seed coating compositions.
  • the aqueous seed treatment compositions of the present disclosure also form coatings that help to reduce dust and attrition all while improving the flowability of coated seeds.
  • the aqueous seed treatment composition for forming the coating on the agricultural seed includes: a) 0.5 to 40 weight percent (wt.%) of a polyester aqueous dispersion, where the wt.% of the polyester aqueous dispersion is based on the total weight of the aqueous seed treatment composition, and where the polyester aqueous dispersion formed with a mixture that includes 30 to 95 wt.% of a polyester and 5 to 70 wt.% of a dispersing agent, where the wt.% of the polyester and the dispersing agent are based on the total weight of the mixture; and water so that the polyester aqueous dispersion has 20 to 60 wt.% solids content based on the total weight of the polyester aqueous dispersion: b) 5 to 60 wt.% of an agriculturally active compound, where the wt.% of the agriculturally active compound is based on the total weight of the aqueous seed treatment composition: and c
  • the aqueous seed treatment composition can include a) 10 to 30 wt.% of the polyester aqueous dispersion; b) 20 to 40 wt.% of the agriculturally active compound; and c) water, where the amount of water brings the wt.% of the aqueous seed treatment composition to 100 wt.%.
  • the aqueous seed treatment composition can further include other additives, as discussed herein.
  • the polyester has a glass transition temperature (Tg) of - 60 to 20 °C measured according to ASTM E1356-08(2014).
  • the polyester can have a glass transition temperature (Tg) of - 60 to 0 °C measured according to ASTM £356-08(2014).
  • the polyester can be selected from the group consisting of polycaprolactone, poly(3-hydroxybutyrate-co-3-hydroxyhexanoate), poly(3- hydroxybutyrate-co-3-hydroxy valerate), poly(3-hydroxy valerate), poly(3-hydroxybutyrate), polyhydroxyalkanoate, polybutylene adipate terephthalate, polyethylene succinate), polypropylene succinate), poly(butylene succinate), poly(butylene succinate adipate), and combinations thereof.
  • the mixture of the polyester aqueous dispersion is in the form of particles having a volume mean diameter (Vmean) of from 20 nm to 2500 nm as measured according to Particle Size Testing provided in the Examples.
  • the particles can have a Vmean of from 100 nm to 2000 nm as measured according to Particle Size Testing provided in the Examples.
  • the mixture can also include 70 to 95 wt.% of the polyester; and 5 to 30 wt.% of the dispersing agent, based on the total solid content of the polyester dispersion.
  • the dispersing agent can be selected from the group consisting of polyvinyl alcohol, fatty alcohol ethoxylates, ethylene oxide/propylene oxide block copolymers, salts of fatty acids and combinations thereof.
  • the polyester and the dispersant of the polyester aqueous dispersion can have a wt.% ratio of 1 :2.3 to 19:1.
  • the agriculturally active compound can be selected from the group consisting of a fungicide, an insecticide, a pesticide, a nematicide, a growth regulator, a safener, a plant activator, biological microbial strains, and combinations thereof.
  • the aqueous seed treatment composition can further include any one of a surfactant, a defoamer, a dye and combination thereof.
  • the present disclosure also provides for an agricultural seed coated with the aqueous seed treatment composition as provided herein.
  • a coating on the agricultural seed is formed using the aqueous seed treatment composition as provided herein.
  • the agricultural seed can be selected from the group consisting of corn seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugar beet seed, rice, sunflower seed, lettuce seed, and spinach seed.
  • the present disclosure also provides for a method of forming the coating on the agricultural seed that includes providing the aqueous seed treatment composition as provided herein in a container; adding the agricultural seed to the container; coating the agricultural seed with the aqueous seed treatment composition; and drying the agricultural seed with the aqueous seed treatment composition to form the coating on the agricultural seed.
  • the method of the present disclosure also includes using a polyester polymer (that is originally present as particles in an aqueous dispersion)having a glass transition temperature (Tg) of -60 to 20 °C measured according to ASTM E1356-08(2014), as discussed herein, in an aqueous seed treatment composition for forming a coating on an agricultural seed.
  • the aqueous seed treatment composition is the aqueous seed treatment composition as provided herein.
  • FIG. 1 Coating weight loss percentage of different aqueous seed treatment compositions according to the present disclosure.
  • FIG. 2 Flowability of different coated seed according to the Flowability test of the Examples section.
  • the present disclosure provides for aqueous seed treatment compositions for forming coatings on agricultural seeds, which address the above identified shortcomings in the art.
  • the aqueous seed treatment (AST) composition for forming the coating on the agricultural seed includes a polyester aqueous dispersion formed with a mixture that includes a polyester, a dispersing agent and water; an agriculturally active compound; and water.
  • the AST compositions can further include other additives, as discussed herein.
  • the AST compositions and coatings of the present disclosure do not contain microplastics. In other words, the AST compositions of the present disclosure are “microplastics-free" seed coating compositions.
  • the AST compositions of the present disclosure also form coatings that help to reduce dust and attrition all while improving the flowability of coated seeds.
  • microplastics refers to particles containing solid polymer, to which additives or other substances may have been added, and where > 1% w/w of particles have (i) all dimensions 0.1 pm ⁇ x ⁇ 5 mm, or (ii), a length of 0.3 pm ⁇ x ⁇ 15 mm and length to diameter ratio of >3.
  • the microplastics restriction can be derogated as microplastics-free if the material is: natural, biodegradable, or water- soluble polymers, or non-polymeric material. (Reference: Draft amendment to the Annex XVII (draft restriction) by Commission, https://echa.europa.eu/hot-topics/microplastics).
  • the AST composition of the present disclosure are microplastics-free.
  • the water is present in an amount, as needed, to bring the wt.% of the AST composition to 100 wt.%.
  • Coatings formed with the AST composition of the present disclosure enhance the adhesion strength of a coating formed with the AST composition while reducing its expulsion rate.
  • the AST composition for forming the coating on the agricultural seed includes: a) 0.5 to 40 weight percent (wt.%) of the polyester aqueous dispersion, where the wt.% of the polyester aqueous dispersion is based on the total weight of the AST composition, and where the polyester aqueous dispersion is formed with a mixture that includes 30 to 95 wt.% of a polyester and 5 to 70 wt.% of a dispersing agent, where the wt.% of the polyester and the dispersing agent are based on the total weight of the mixture; and water that is added to the mixture so that the polyester aqueous dispersion has 20 to 60 wt.% solids content based on the total weight of the polyester aqueous dispersion: b) 5 to 60 wt.% of the agriculturally active compound, where the wt.% of the agriculturally active compound is based on the total weight of the AST composition: and c) water, where the amount
  • the polyester makes up 30 to 95 wt.% of the mixture, where the wt.% is based on the total weight of the mixture.
  • this provides the AST composition with a polyester content from the mixture of 0.03 to 23 wt.% based on the total weight of the AST composition.
  • the polyester makes up 70 to 95 wt.% of the mixture, where the wt.% is based on the total weight of the mixture.
  • this provides the AST composition with a polyester content from the mixture of 0.07 to 22 wt.% based on the total weight of the AST composition.
  • the polyester has a glass transition temperature (Tg) of - 60 to 20 °C measured according to ASTM E1356-08(2014).
  • the polyester can have a glass transition temperature (Tg) of - 60 to 0 °C measured according to ASTM £356-08(2014).
  • the polyester used in the AST composition can be obtained in accordance with conventional procedures well known to those of ordinary skill in the art by reacting, for example, a polybasic acid that contains at least two carboxyl groups per polybasic acid molecule (e.g. a dibasic polycarboxylic acid) with a polyhydric alcohol that contains at least two hydroxyl groups in the polyhydric alcohol (e.g., a dihydric alcohol) in presence of a conventional esterification catalyst at an elevated temperature with or without solvent present.
  • a polybasic acid that contains at least two carboxyl groups per polybasic acid molecule e.g. a dibasic polycarboxylic acid
  • a polyhydric alcohol that contains at least two hydroxyl groups in the polyhydric alcohol e.g., a dihydric alcohol
  • ElvanolTM 85-82 available from Kuraray Co., Ltd.
  • SelvolTM E310 available from Sekisui Specialty Chemicals America
  • SelvolTM 205 or 205U available from Sekisui Specialty Chemicals America.
  • Blends of different PVA grades can be used.
  • the fatty alcohol ethoxylate can have the general formula: R(OC2H4)nOH, where n is an integer in the range of 6 to 150 and R is a C8 to C18 alkyl (straight chain or branched).
  • R is a C8 to C18 alkyl (straight chain or branched).
  • the fatty alcohol ethoxylate has an n in the range of 20 to 60 and R is a C12 to C18 alkyl (straight chain or branched).
  • the alkyl chain can be from natural resources such as seed oil or from petroleum process.
  • the alkyl chain can be fully saturated or have one or multiple unsaturation.
  • the ethylene oxide/propylene oxide block copolymer can have a weight ratio of the ethylene oxide to the propylene oxide in the range of 1 :5 to _10:1 .
  • the ethylene oxide/propylene oxide block copolymer can have a weight average molecular weight in a range of 1000 to 40,000 g/mol.
  • the ethylene oxide/propylene oxide block copolymer can have a weight ratio of the ethylene oxide to the propylene oxide in the range of 2:1 to 5:1 and a weight average molecular weight in a range of 5000 to 20,000 g/mol.
  • the dispersing agent used in the polyester aqueous dispersion can also be from the group of water-soluble polymers including homopolymers or copolymers and their salts from the monomers of acrylic acid, methacrylic acid, maleic anhydride, styrene, benzyl acrylate, butyl acrylate, methyl methacrylate.
  • the acrylic polymers used can have a molecular weight in the range of 1000 to 200,000 g/mol and water solubility > 2g/L via procedure described in OECD Guideline 120 or 105.
  • the counter ion salts can be potassium, sodium, ammonium or organic amines. Examples of such polymers include DISPERBYK-190 from BYK, TEGO ® Dispers 752 from Evonik, TOMALTM 731 A from Dow Chemical Company.
  • the dispersing agent used in the polyester aqueous dispersion can also be from polysaccharides and their derivatives.
  • polysaccharide derivatives include cellulose ethers such as methylcellulose, ethylcelluose, hydroxyproyl methylcellulose; cellulose esters such as carboxymethyl cellulose.
  • the molecular weight of such polymers can be from 5000 to 1 ,000,000 g/mol.
  • the water solubility of such polymers should > 2g/L via procedure described in OECD Guideline 120 or 105.
  • polymers examples include TEXTURECELTM 1000 PA from Dupont, TEXTURECELTM 30 GA from Dupont, METHOCELTM cellulose ethers such as METHOCELTM 240 from Dupont, BenecelTM E10M from Ashland.
  • Examples of the dispersing agent include those selected from polyvinyl alcohols include commercially available products under the trade name POVALTM, such as POVALTM 6- 88, POVALTM 18-88, and MOWIOLTM, such as MOWIOLTM 4-88, among others.
  • Examples of ethylene oxide/propylene oxide block copolymers include those sold under the trade name PLURONIC®, such as PLURONIC® F-108 (Poloxamer 338), PLURONIC® F88 (Poloxamer 188), PLURONIC® F127 (Poloxamer 407).
  • Embodiments provide that the mixture, as provided herein, can be melt-kneaded in an extruder, e.g. via a continuous melt emulsification process, to form the aqueous polyester dispersion of the present disclosure.
  • the aqueous polyester emulsion is first diluted to contain about 10 to about 30% by weight water and then, subsequently, further diluted to comprise 40 to 80 % by weight of water before cooling below the melting temperature of the polyester to form the final aqueous polyester dispersion of the mixture.
  • the dispersing agent and water are preheated in a preheater.
  • the polyester e.g., in the form of pellets, powder, or flakes
  • the polyester can be fed from the feeder to an inlet of an extruder where they are melted.
  • a dispersing agent can be added to the polyester through and along with the polyester and in other embodiments, the dispersing agent can be provided separately to the extruder.
  • the melted polyester polymers can then be delivered from the mix and convey zone to an emulsification zone of the extruder where an initial amount of water and/or dispersing agent from the water and dispersing agent reservoirs can be added through one or more of an inlet.
  • the agriculturally active compound is selected from the group consisting of a fungicide, an insecticide, a pesticide, a nematicide, a growth regulator, a safener, a plant activator, biological microbial strains and combinations thereof.
  • the amount of the agriculturally active compound to be used in the AST composition can vary due to the strength of the active ingredient.
  • the amount of the agriculturally active compound used in the AST composition is from 5 to 60 wt.% based on the total weight of the AST composition.
  • the amount of the agriculturally active compound used in the AST composition is from 10 to 50 wt.% based on the total weight of the AST composition.
  • the amount of the agriculturally active compound in the AST composition can vary depending on the type of seed and the particular agriculturally active compound.
  • suitable fungicides include those selected from Captan (N- (trichloromethyl)thio-4-cyclohexane-1 ,2-dicarboximide); Thiram (tetramethylthioperoxydicarbonic diamide; Metalaxyl (methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate; Fludioxonil (4-(2,2-difluoro-1 ,3-benzodioxol-4-yl)-1 H-pyrrol-3-carbonitrile; and Oxadixyl (N-(2,6- dimethylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl) acetamide.
  • Captan N- (trichloromethyl)thio-4-cyclohexane-1 ,2-dicarbox
  • suitable insecticides include those selected from thiamethoxam, azoles such as, for example, triazoles, azines, pyrethroids, organophosphates, caramoyloximes, pyrroles, pyrazoles, pyridines, amidines, halogenated hydrocarbons, and carbamates and combinations and derivatives thereof.
  • Particularly suitable classes of insecticides include insect growth regulators, organophosphates, phenylpyrazoles and pyrethroids.
  • suitable growth regulator examples include those selected from Antiauxins, such as clofibric acid and 2,3,5-tri-iodobenzoic acid; Auxins, such as 4-CPA, 2,4-D, 2,4-DB, 2,4- DEP, Dichlorprop, fenoprop, IAA, IBA, Naphthaleneacetamide, a-naphthaleneacetic acid, 1 - naphthol, naphthoxyacetic acids, MCPA-thioethyl, potassium naphthenate, sodium naphthenate and 2,4,5-T; Cytokinins, such as 2iP, Benzyladenine, 6-benzylaminopurine, kinetin and zeatin; Defoliants, such as calcium cyanamide, dimethipin, endothal, ethephon, merphos, metoxuron, pentachlorophenol, thidiazuron and tributes; Ethylene inhibitors, such as avigly
  • Suitable safeners include those selected from benzoxazine, benzhydryl derivatives, N , N-diallyl dichloroacetamide, various dihaloacyl, oxazolidinyl and thiazolidinyl compounds, ethanone, naphthalic anhydride compounds, and oxime derivatives.
  • suitable plant activators include those selected from harpin, reynoutria sachalinensis, jasmonate, lipochitooligosaccharides, and isoflavones, among others.
  • the above compounds are listed as examples and are not intended to be an exhaustive list of compounds that can be used in the AST composition of the present disclosure.
  • the AST composition can further include any one of a surfactant, a rheology modifier, a cosolvent, a defoamer, dispersing agent for the active ingredient of the AST composition, a pigment or dye and combination thereof.
  • a surfactant for the active ingredient of the AST composition
  • a cosolvent for the active ingredient of the AST composition
  • a defoamer for the active ingredient of the AST composition
  • dispersing agent for the active ingredient of the AST composition a pigment or dye and combination thereof.
  • the AST composition can have a viscosity, measured as described in the Examples section herein, of less than 3000 centipoises (cP).
  • the AST composition can have a viscosity in the range of 20 to 3000 cP.
  • the AST composition can have a viscosity in the range of 20 to 2000 cP.
  • the AST composition can have a viscosity in the range of 500 to 2000 cP.
  • AST composition can initially be provided as a concentrate, where either (i) water or (ii) water and the agriculturally active compound are not present in the composition.
  • the present disclosure also provides a method of forming a coating on an agricultural seed using the AST composition of the present disclosure.
  • the method of forming the coating on the agricultural seed can include providing the AST composition of the present disclosure in a container, adding the agricultural seed to the container; coating the agricultural seed with the AST composition; and drying the agricultural seed with the AST composition to form the coating on the agricultural seed.
  • the agricultural seed is coated with the AST composition.
  • the resulting product is a coating on an agricultural seed formed using the AST composition of the present disclosure.
  • the agricultural seed can be any of those provided herein, e.g., selected from the group consisting of corn seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugar beet seed, rice, sunflower seed, lettuce seed, and spinach seed.
  • the present disclosure also provides for a method of using the AST composition having the polyester polymer with a glass transition temperature (Tg) of -60 to 20 °C measured according to ASTM £1356-08(2014), where the AST composition forms the coating on the agricultural seed as discussed herein.
  • the AST composition is the AST composition as provided herein.
  • Conventional means of coating may be used for forming the coating on the agricultural seed using the AST composition of the present disclosure.
  • Various coating machines such as drum coaters, Munson Machinery, pan coaters, rotary continuous coaters, and fluidized bed techniques are known and available to one skilled in the art for carrying out the coating process. Other methods, such as spouted beds may also be useful.
  • the agricultural seeds may be pre-sized prior to coating. After coating the agricultural seeds are dried and then optionally sized by transfer to a sizing machine. These machines are known in the art for example, a typical machine used when sizing seed corn in the industry.
  • Film-forming compositions for enveloping coated seeds are well known in the art, and a film overcoating can be optionally applied to the coated seeds of the present disclosure.
  • the film overcoat can protect the coating formed using the AST composition and optionally allows for easy identification of the treated seeds.
  • additives are dissolved or dispersed in a liquid adhesive, usually a polymer into or with which seeds are dipped or sprayed before drying.
  • a powder adhesive can be used.
  • the AST composition of the present disclosure can also include one or more of an anti-freeze agent, an anti-foam agent, a thickener and/or a pigment, where the pigment can be in the form of a pigment slurry.
  • the amount of any one of these additional components used may vary, but generally can be present in the AST composition in a range of 0.005 wt.% to 5 wt.%.
  • anti-freeze agents include, but are not limited to, propylene glycol, ethylene glycol.
  • anti-foam agents include, but are not limited to, DOW CORNINGTM AFE- 0020 Antifoam Emulsion.
  • thickeners include, but are not limited to, xanthan gum.
  • pigments include, but are not limited to, Pigment Permanent Red, Pigment Phthalocyanine Blue.
  • any agricultural seed can be coated with the AST composition to form a coating on the agricultural seed.
  • the agricultural seed can be selected from the group consisting of corn seed (sweet and field), sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugar beet seed, rice, sunflower seed, lettuce seed, and spinach seed.
  • suitable agricultural seeds include, but are not limited to, cereals, ornamentals, fruit seeds, cotton, alfalfa, sorghum, rapeseed, Brassica, tomato, bean, carrot, tobacco and flower seeds such as pansy, impatiens, petunia and geranium.
  • the most preferred agricultural seeds include corn and soybean.
  • Materials employed in the inventive examples (IE) and/or comparative examples (CE) include the following.
  • polyester aqueous dispersions 1 -4 and Comparative Examples of the Polymer dispersions 1 -3 have the polymer phase components and physical properties as shown in Tables 3, 4 and 5, and were prepared with the raw materials shown in Table 1 using the general procedure, process, and conditions described herein.
  • the thermoplastic polyester resin and dispersant listed for each example in Tables 3, 4 and 5 were fed into a 25 mm diameter twin screw extruder using a controlled rate feeder at the given ratios listed in Tables 3 and 4 at a total feed rate of 75.6 g/min.
  • a backpressure regulator was used to adjust the pressure inside the extruder barrel to a pressure adapted to reduce steam formation (generally the pressure was from 2 MPa to 4 Mpa).
  • Each polyester dispersion exited from the extruder and was filtered first through a 200 micrometer (pm) filter.
  • the resultant filtered polyester dispersion had a solids content measured in weight percent (wt %); and the solids particles of the polyester dispersion has a volume mean particle size measured in microns.
  • the dust measurement process was as follows. Measure 650 g of Test Material, which was formed from approximately 13 grams of the coating corn seed of the IE or CE and 637 g of un-coated corn seeds. Screen the pre-existing fines in the Test Material using a mesh #12 (1 ,68mm) screen and Rotap sieve shaker for 1 minutes without tapping enabled. Separate the fines from the Test Material and record the mass of the Test Material after the first sieve: m ( . Load the resulting Test Material (coated corn seeds and un-coated corn seeds) into the milling jar of the ball mill. Place the loaded milling jar onto the roller of the ball mill. Run the ball mill at 65 rpm for 5 minutes. Unloaded the content of the milling jar on a #12 screen as provided above. Shake the screen for 1 minutes using Rotap shaker and record the mass retained, m f . The total dust attrition was calculated according to the Equation (1 ).
  • Flowability was measured using a 3D printing hopper having a valve positioned at its outlet in combination with a high-speed camera to record the discharge of coated seeds from the hopper.
  • the outlet of the hopper had a diameter of 4.2 cm, where the inner diameter of the vertical section of the hopper is 8.9 cm and heigh of the vertical part is 14.6 cm.
  • the angle of conical portions between the outlet and the vertical portions of the hopper were 14.47 degree.
  • the flowability tests were done at room temperature (22 °C). During the filling process, the valve of the hopper remained securely closed. All flowability experiments were conducted with batches containing 750 grams of material, encompassing both seeds and their respective coatings. Once the valve was secured in the closed position, the high-speed camera commences its recording process.
  • the valve is promptly opened, allowing seeds to flow freely until complete discharge is achieved.
  • the image recording process is temporarily paused.
  • the total discharged time required for the granules to completely exit the hopper was calculated with an accuracy of up to 0.001 seconds. Consequently, a determine of the average mass flow rate associated with each specific coating can be calculated with Equation (2).
  • Acrylic latex and polyvinyl alcohol have long been used as film forming agents in the seed coating industry to reduce dust generation and improve other properties such as flowability.
  • Acrylic latex has been seen as the workhorse due to its performance, processibility and low cost.
  • Acrylic latex falls into the microplastic definition and the use of it will likely be restriction in areas including but not limited to agricultural application (e.g., coatings for agricultural seeds).
  • Polyvinyl alcohol or PVOH may be deregulated from this restriction due to its water solubility.
  • the performance of PVOH as film forming agent is inadequate. Plus, the viscosity of PVOH goes up quickly when concentration passes over 10 wt.% in water at room temperature. Ideally for a good film forming agent, the viscosity should be below 3000 cP for good pumpability at a reasonable solid content (e.g., 30-60 wt.%).
  • the corn seeds coated with the seed coating compositions of the CEs seen in Table 5 initially showed good coverage, except for CE-PVOH1 and CE-PVOH2. This may have been partially due to the high viscosity profile of CE-PVOH1 and CE-PVOH2, which negatively impact the flow of the aqueous composition during the coating process.
  • All polyester aqueous dispersions both IE and CE provided coverage that was comparable to the blank sample (CE-Blank) and the sample using commercial acrylic latex as film former (CE-Acrylic1 ).
  • CE-Acrylic1 commercial acrylic latex as film former
  • the coating of CE-blank became thin and crumbled after attrition.
  • the addition of commercial acrylic latex CE-Acrlyic1 did not improve the attrition. Even worse failure was observed for CE- PVOH1 and CE-PVOH2, where corn seed skin was exposed in many seeds after attrition.
  • the coated seeds in inventive examples all showed great resistance to attrition, with only minimal loss of coating mainly at the crown area of the seed.
  • the coated surfaces of all inventive samples remain smooth and glossy, indicating minimal dust generation during attrition.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Dentistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Chemical & Material Sciences (AREA)
  • Insects & Arthropods (AREA)
  • Soil Sciences (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

Abstract

The present disclosure provides for agricultural seed coating compositions and coatings therefrom. The aqueous seed treatment composition for forming the coating on the agricultural seed includes a polyester aqueous dispersion formed with a mixture that includes a polyester, a dispersing agent and water; an agriculturally active compound; and water.

Description

AQUEOUS SEED TREATMENT COMPOSITIONS AND COATINGS THEREFROM Field of Disclosure
[001] The present disclosure relates generally to aqueous seed treatment compositions and coatings therefrom.
Background
[002] Agricultural seeds can be coated with seed coating compositions that include active ingredients such as pesticides, biologies, or nutrients along with other additives such as wetting agents, dispersants, and film forming agents. Film forming agent (FFA, a.k.a. binder, film former, filmer) in the coating compositions serves as a binder to “glue” all ingredients into a continuous film on the surface of the seed. Besides binding active ingredients, FFAs also provide important properties for the seed coating, such as dust control, wet and dry flowability and water resistance among others. Conventionally, acrylic latex has dominated the seed coating composition market along with other chemistries such as polyolefin dispersion, polyurethane dispersion, cellulose, polyvinyl alcohol and polyvinyl acetates. But there are issues with such conventional FFAs.
[003] Because of the unfolding microplastics restriction and increasing call for sustainable solutions in seed coating industry, conventional FFAs especially acrylic latex based FFA are under scrutiny. There is a strong call for microplastics-free FFA with performances comparable to or better than acrylic latex incumbents. To this end the top two performance indicators for any new seed coating composition include dust control and flowability of the coated seeds. Other challenges in developing suitable seed coating compositions include price and processibility. Achieving all three of these important aspects for any microplastics-free seed coating composition (performance, price and processability) is difficult. This shortcoming demonstrates the continued need in the art for such a microplastics-free seed coating composition that helps to, among other things, reduce dust and attrition and improve flowability of coated seed.
Summary
[004] The present disclosure provides for aqueous seed treatment compositions for forming coatings on agricultural seeds, which address the above identified shortcomings in the art. The aqueous seed treatment composition for forming the coating on the agricultural seed includes a polyester aqueous dispersion formed with a mixture that includes a polyester, a dispersing agent and water; an agriculturally active compound; and water. The aqueous seed treatment composition can further include other additives, such as one or more of a pigment, a dispersing agent for the active ingredient, a defoamer, rheology modifiers and cosolvents, as discussed herein, The aqueous seed treatment composition for forming the coating on the agricultural seed of the present disclosure do not contain microplastics. In other words, the aqueous seed treatment compositions of the present disclosure are microplastics-free seed coating compositions. The aqueous seed treatment compositions of the present disclosure also form coatings that help to reduce dust and attrition all while improving the flowability of coated seeds.
[005] For the present disclosure, the aqueous seed treatment composition for forming the coating on the agricultural seed includes: a) 0.5 to 40 weight percent (wt.%) of a polyester aqueous dispersion, where the wt.% of the polyester aqueous dispersion is based on the total weight of the aqueous seed treatment composition, and where the polyester aqueous dispersion formed with a mixture that includes 30 to 95 wt.% of a polyester and 5 to 70 wt.% of a dispersing agent, where the wt.% of the polyester and the dispersing agent are based on the total weight of the mixture; and water so that the polyester aqueous dispersion has 20 to 60 wt.% solids content based on the total weight of the polyester aqueous dispersion: b) 5 to 60 wt.% of an agriculturally active compound, where the wt.% of the agriculturally active compound is based on the total weight of the aqueous seed treatment composition: and c) water, where the amount of water brings the wt.% of the aqueous seed treatment composition to 100 wt.%. In an additional embodiment, the aqueous seed treatment composition can include a) 10 to 30 wt.% of the polyester aqueous dispersion; b) 20 to 40 wt.% of the agriculturally active compound; and c) water, where the amount of water brings the wt.% of the aqueous seed treatment composition to 100 wt.%. The aqueous seed treatment composition can further include other additives, as discussed herein.
[006] For the present disclosure, the polyester has a glass transition temperature (Tg) of - 60 to 20 °C measured according to ASTM E1356-08(2014). In an additional embodiment, the polyester can have a glass transition temperature (Tg) of - 60 to 0 °C measured according to ASTM £1356-08(2014). For the present disclosure, the polyester can be selected from the group consisting of polycaprolactone, poly(3-hydroxybutyrate-co-3-hydroxyhexanoate), poly(3- hydroxybutyrate-co-3-hydroxy valerate), poly(3-hydroxy valerate), poly(3-hydroxybutyrate), polyhydroxyalkanoate, polybutylene adipate terephthalate, polyethylene succinate), polypropylene succinate), poly(butylene succinate), poly(butylene succinate adipate), and combinations thereof.
[007] For the present disclosure, the mixture of the polyester aqueous dispersion is in the form of particles having a volume mean diameter (Vmean) of from 20 nm to 2500 nm as measured according to Particle Size Testing provided in the Examples. In an additional embodiment, the particles can have a Vmean of from 100 nm to 2000 nm as measured according to Particle Size Testing provided in the Examples. For the present disclosure, the mixture can also include 70 to 95 wt.% of the polyester; and 5 to 30 wt.% of the dispersing agent, based on the total solid content of the polyester dispersion.
[008] For the present disclosure, the dispersing agent can be selected from the group consisting of polyvinyl alcohol, fatty alcohol ethoxylates, ethylene oxide/propylene oxide block copolymers, salts of fatty acids and combinations thereof. For the present disclosure, the polyester and the dispersant of the polyester aqueous dispersion can have a wt.% ratio of 1 :2.3 to 19:1.
[009] For the present disclosure, the agriculturally active compound can be selected from the group consisting of a fungicide, an insecticide, a pesticide, a nematicide, a growth regulator, a safener, a plant activator, biological microbial strains, and combinations thereof. For the present disclosure, the aqueous seed treatment composition can further include any one of a surfactant, a defoamer, a dye and combination thereof.
[010] The present disclosure also provides for an agricultural seed coated with the aqueous seed treatment composition as provided herein. For the present disclosure, a coating on the agricultural seed is formed using the aqueous seed treatment composition as provided herein. For the present disclosure, the agricultural seed can be selected from the group consisting of corn seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugar beet seed, rice, sunflower seed, lettuce seed, and spinach seed.
[01 1] The present disclosure also provides for a method of forming the coating on the agricultural seed that includes providing the aqueous seed treatment composition as provided herein in a container; adding the agricultural seed to the container; coating the agricultural seed with the aqueous seed treatment composition; and drying the agricultural seed with the aqueous seed treatment composition to form the coating on the agricultural seed. As discussed herein, the method of the present disclosure also includes using a polyester polymer (that is originally present as particles in an aqueous dispersion)having a glass transition temperature (Tg) of -60 to 20 °C measured according to ASTM E1356-08(2014), as discussed herein, in an aqueous seed treatment composition for forming a coating on an agricultural seed. For the present disclosure, the aqueous seed treatment composition is the aqueous seed treatment composition as provided herein. Brief Description of the Drawings
[012] FIG. 1 Coating weight loss percentage of different aqueous seed treatment compositions according to the present disclosure.
[013] FIG. 2 Flowability of different coated seed according to the Flowability test of the Examples section.
Detailed Description
[014] The present disclosure provides for aqueous seed treatment compositions for forming coatings on agricultural seeds, which address the above identified shortcomings in the art. The aqueous seed treatment (AST) composition for forming the coating on the agricultural seed includes a polyester aqueous dispersion formed with a mixture that includes a polyester, a dispersing agent and water; an agriculturally active compound; and water. The AST compositions can further include other additives, as discussed herein. The AST compositions and coatings of the present disclosure do not contain microplastics. In other words, the AST compositions of the present disclosure are “microplastics-free" seed coating compositions. The AST compositions of the present disclosure also form coatings that help to reduce dust and attrition all while improving the flowability of coated seeds.
[015] As provided herein, microplastics refers to particles containing solid polymer, to which additives or other substances may have been added, and where > 1% w/w of particles have (i) all dimensions 0.1 pm < x < 5 mm, or (ii), a length of 0.3 pm < x < 15 mm and length to diameter ratio of >3. The microplastics restriction can be derogated as microplastics-free if the material is: natural, biodegradable, or water- soluble polymers, or non-polymeric material. (Reference: Draft amendment to the Annex XVII (draft restriction) by Commission, https://echa.europa.eu/hot-topics/microplastics). The AST composition of the present disclosure are microplastics-free.
[016] The present disclosure provides for an AST composition for forming a coating on an agricultural seed. The AST composition of the present disclosure is formed from a polyester aqueous dispersion, an agriculturally active compound and water. For the AST composition, the polyester aqueous dispersion is formed from a polyester, a dispersing agent, both as provided herein, and water so that the polyester aqueous dispersion has 20 to 60 wt.% solids content based on the total weight of the polyester aqueous dispersion. For the AST composition, the agriculturally active compound is present in an amount ranging from 5 to 60 wt.%, where the wt.% of the agriculturally active compound is based on the total weight of the AST composition. For the AST composition, the water is present in an amount, as needed, to bring the wt.% of the AST composition to 100 wt.%. Coatings formed with the AST composition of the present disclosure enhance the adhesion strength of a coating formed with the AST composition while reducing its expulsion rate.
[017] As used herein, the terms "coating on an agricultural seed" or “coatings formed with the AST composition” mean an agricultural seed that has been subjected to a procedure whereby the agricultural seed is treated with one or more adhering coating layers of the AST composition of the present disclosure. The method portion of this disclosure provides suitable techniques for forming one or more of the coating on the agricultural seed, as provided herein. [018] For the present disclosure, the AST composition for forming the coating on the agricultural seed includes: a) 0.5 to 40 weight percent (wt.%) of the polyester aqueous dispersion, where the wt.% of the polyester aqueous dispersion is based on the total weight of the AST composition, and where the polyester aqueous dispersion is formed with a mixture that includes 30 to 95 wt.% of a polyester and 5 to 70 wt.% of a dispersing agent, where the wt.% of the polyester and the dispersing agent are based on the total weight of the mixture; and water that is added to the mixture so that the polyester aqueous dispersion has 20 to 60 wt.% solids content based on the total weight of the polyester aqueous dispersion: b) 5 to 60 wt.% of the agriculturally active compound, where the wt.% of the agriculturally active compound is based on the total weight of the AST composition: and c) water, where the amount of water brings the wt.% of the AST composition, as necessary, to 100 wt.%. In an additional embodiment, the AST composition can include a) 10 to 30 wt.% of the polyester aqueous dispersion; b) 20 to 40 wt.% of the agriculturally active compound; and c) water, where the amount of water brings the wt.% of the AST composition, as needed, to 100 wt.%.
[019] For the present disclosure, the AST composition for forming the coating on the agricultural seed includes 0.5 to 40 wt.% of the polyester aqueous dispersion based on the total weight of the AST composition. As discussed herein, the polyester aqueous dispersion has 20 to 60 wt.% solids content based on the total weight of the polyester aqueous dispersion. Preferably, the polyester aqueous dispersion can have 25 to 40 wt.% solids content based on the total weight of the polyester aqueous dispersion. Of the solids content of the polyester aqueous dispersion e.g., 20 to 60 wt.% solids content), the polyester makes up 30 to 95 wt.% of the mixture, where the wt.% is based on the total weight of the mixture. For the present disclosure, this provides the AST composition with a polyester content from the mixture of 0.03 to 23 wt.% based on the total weight of the AST composition. In an additional embodiment, the polyester makes up 70 to 95 wt.% of the mixture, where the wt.% is based on the total weight of the mixture. For the additional embodiment, this provides the AST composition with a polyester content from the mixture of 0.07 to 22 wt.% based on the total weight of the AST composition. Preferably, the AST composition includes 1 to 10 wt.% of the polyester as a solid from the mixture based on the total weight of the AST composition. In another example, the AST composition includes 1 .5 to 5.5 wt.% of the polyester as a solid from the mixture based on the total weight of the AST composition.
[020] For the present disclosure, the polyester has a glass transition temperature (Tg) of - 60 to 20 °C measured according to ASTM E1356-08(2014). In an additional embodiment, the polyester can have a glass transition temperature (Tg) of - 60 to 0 °C measured according to ASTM £1356-08(2014). For the present disclosure, the polyester can be selected from the group consisting of polycaprolactone, poly(3-hydroxybutyrate-co-3-hydroxyhexanoate), poly(3- hydroxybutyrate-co-3-hydroxy valerate), poly(3-hydroxy valerate), poly(3-hydroxybutyrate), polyhydroxyalkanoate, polybutylene adipate terephthalate, polyethylene succinate), polypropylene succinate), poly(butylene succinate), poly(butylene succinate adipate), and combinations thereof.
[021] The polyester used in the AST composition can have a weight average molecular weight of 1000 to 1 ,000,000 g/mol. Preferably, the polyester used in the AST composition can have a weight average molecular weight of 10,000 to 200,000 g/mol. More preferably, the polyester used in the AST composition can have a weight average molecular weight of 15,000 to 100,000 g/mol. Techniques for measuring the weight average molecular weight include, but are not limited to, static light scattering or gel permeation chromatography (GPC) using polystyrene standards, as are known in the art. A variety of polymerization techniques as are known in the art can be used to prepare the polyester of the present disclosure. Examples include those provided in U.S. Pat. Nos. 9,637,587 B2; 8,975,344 B2; 10,538,792 and 8,604,156 B2, among others. Generally, the polyester used in the AST composition can be obtained in accordance with conventional procedures well known to those of ordinary skill in the art by reacting, for example, a polybasic acid that contains at least two carboxyl groups per polybasic acid molecule (e.g. a dibasic polycarboxylic acid) with a polyhydric alcohol that contains at least two hydroxyl groups in the polyhydric alcohol (e.g., a dihydric alcohol) in presence of a conventional esterification catalyst at an elevated temperature with or without solvent present. Alternatively, alkyl esters of the polycarboxylic acids or anhydrides of polycarboxylic acids can be reacted in presence of a conventional esterification catalyst at an elevated temperature. Alternatively, a homopolymer or copolymer of hydroxcarboxy acid can be synthesized by ringopening polymerization with the presence of catalysts. One or more polymerizable double bonds may be included into the polyester by employing a polybasic acid that contains polymerizable double bonds and/or a polyhydric alcohol that contains polymerizable double bonds. Also alternatively, the polyester can be from metabolites of microorganisms through fermentation as provided in US 10,538,792 B2.
[022] For the present disclosure, the mixture of the polyester aqueous dispersion can include 5 to 70 wt.% of the dispersing agent, where the wt.% of the dispersing agent is based on the total weight of the mixture. Preferably, the mixture of the polyester aqueous dispersion includes 5 to 30 wt.% of the dispersing agent, where the wt.% of the dispersing agent is based on the total weight of the mixture. For the present disclosure, the mixture can preferably include 70 to 95 wt.% of the polyester; and 5 to 30 wt.% of the dispersing agent, where the wt.% values are based on the total weight of the mixture.
[023] For the present disclosure, the dispersing agent is selected from the group consisting of polyvinyl alcohol, fatty alcohol ethoxylates, ethylene oxide/propylene oxide block copolymers, salts of fatty acids and combinations thereof. For the present disclosure, the polyvinyl alcohol can have a degree of hydrolysis of 50 to 100%. Preferably, the polyvinyl alcohol can have a degree of hydrolysis of 80 to 95%. The polyvinyl alcohol used can have a viscosity (mPa*sec of a 4% aqueous solution at 20 °C) in the range of 3 to 95. Alternatively, the polyvinyl alcohol used can have a viscosity (mPa*sec of a 4% aqueous solution at 20°C) less than 30, or a viscosity less than 10. Examples of commercially available PVA include Poval™ 4-88 available from Kuraray Co., Ltd.; Poval™ 6-88, available from Kuraray Co., Ltd.; Poval™ 18-88, available from Kuraray Co., Ltd.; Poval™ 10-98, available from Kuraray Co., Ltd.;
Elvanol™ 85-82, available from Kuraray Co., Ltd.; Selvol™ E310, available from Sekisui Specialty Chemicals America, Selvol™ 205 or 205U, available from Sekisui Specialty Chemicals America. Blends of different PVA grades can be used.
[024] For the present disclosure, the fatty alcohol ethoxylate can have the general formula: R(OC2H4)nOH, where n is an integer in the range of 6 to 150 and R is a C8 to C18 alkyl (straight chain or branched). Preferably, the fatty alcohol ethoxylate has an n in the range of 20 to 60 and R is a C12 to C18 alkyl (straight chain or branched). The alkyl chain can be from natural resources such as seed oil or from petroleum process. The alkyl chain can be fully saturated or have one or multiple unsaturation.
[025] For the present disclosure, the ethylene oxide/propylene oxide block copolymer can have a weight ratio of the ethylene oxide to the propylene oxide in the range of 1 :5 to _10:1 . In addition, the ethylene oxide/propylene oxide block copolymer can have a weight average molecular weight in a range of 1000 to 40,000 g/mol. Preferably, the ethylene oxide/propylene oxide block copolymer can have a weight ratio of the ethylene oxide to the propylene oxide in the range of 2:1 to 5:1 and a weight average molecular weight in a range of 5000 to 20,000 g/mol.
[026] For the present disclosure, the dispersing agent used in the polyester aqueous dispersion can also be from the group of water-soluble polymers including homopolymers or copolymers and their salts from the monomers of acrylic acid, methacrylic acid, maleic anhydride, styrene, benzyl acrylate, butyl acrylate, methyl methacrylate. The acrylic polymers used can have a molecular weight in the range of 1000 to 200,000 g/mol and water solubility > 2g/L via procedure described in OECD Guideline 120 or 105. The counter ion salts can be potassium, sodium, ammonium or organic amines. Examples of such polymers include DISPERBYK-190 from BYK, TEGO ® Dispers 752 from Evonik, TOMAL™ 731 A from Dow Chemical Company.
[027] For the present disclosure, the dispersing agent used in the polyester aqueous dispersion can also be from polysaccharides and their derivatives. Examples of polysaccharide derivatives include cellulose ethers such as methylcellulose, ethylcelluose, hydroxyproyl methylcellulose; cellulose esters such as carboxymethyl cellulose. The molecular weight of such polymers can be from 5000 to 1 ,000,000 g/mol. The water solubility of such polymers should > 2g/L via procedure described in OECD Guideline 120 or 105. Examples of such polymers include TEXTURECEL™ 1000 PA from Dupont, TEXTURECEL™ 30 GA from Dupont, METHOCEL™ cellulose ethers such as METHOCEL™ 240 from Dupont, Benecel™ E10M from Ashland.
[028] For the present disclosure, the dispersing agent used in the polyester aqueous dispersion can also be lignin derivatives. The weight average molecular weight of the lignin derivatives can be from 2000 to 50,000 g/mol, and the viscosity measured under condition Brookfield RVF — 100 No. 2 spindle at 20 rpm, 30% solids, T = 25 °C, can be in the range of 2 to 3000 cP. Preferably, the viscosity can be less than 150 cP. Examples of lignin derivatives include lignin sulfonate and lignin sulfate such as Polyfon ® H, Reax 80D, Kraftsperse 1251 from Ingevity.
[029] Examples of the dispersing agent include those selected from polyvinyl alcohols include commercially available products under the trade name POVAL™, such as POVAL™ 6- 88, POVAL™ 18-88, and MOWIOL™, such as MOWIOL™ 4-88, among others. Examples of ethylene oxide/propylene oxide block copolymers include those sold under the trade name PLURONIC®, such as PLURONIC® F-108 (Poloxamer 338), PLURONIC® F88 (Poloxamer 188), PLURONIC® F127 (Poloxamer 407). Examples of fatty alcohol ethoxylates include Brij™ S100 (steareth 100), Brij™ S721 (steareth 21) and Brij™ 35 (laureth L23). Examples of salts of fatty acids include fatty acids such as oleic acid, stearic acid, or montanic acid neutralized by a base such as sodium hydroxide, potassium hydroxide, ammonia, or an organic amine such as dimethylethanolamine.
[030] For the present disclosure, the polyester and the dispersant of the polyester aqueous dispersion of the mixture used in the AST composition for forming the coating on the agricultural seed can have a wt.% ratio of 1 :2.3 to 19:1 (polyester : dispersant agent), where the 1 :2.3 represents the example where the polyester is present in an amount of 30 wt.% and the dispersing agent is present in an amount of 70 wt.%, and the 19:1 represents the example where the polyester is present in an amount of 95 wt.% and the dispersing agent is present in an amount of 5 wt.%, based on the total weight of the mixture.
[031] As noted herein, the polyester can be present as a polyester aqueous dispersion formed using a number of different techniques known in the art. The polyester aqueous dispersion includes a fluid medium, e.g., water. The polyester aqueous dispersion is formed with a mixture that includes 30 to 95 wt.% of the polyester and 5 to 70 wt.% of the dispersing agent, where the wt.% of the polyester and the dispersing agent are based on the total weight of the mixture; and includes water so that the polyester aqueous dispersion has 20 to 60 wt.% solids content based on the total weight of the polyester aqueous dispersion. Embodiments provide that the mixture, as provided herein, can be melt-kneaded in an extruder, e.g. via a continuous melt emulsification process, to form the aqueous polyester dispersion of the present disclosure. In a number of embodiments, during the melt emulsification process the aqueous polyester emulsion is first diluted to contain about 10 to about 30% by weight water and then, subsequently, further diluted to comprise 40 to 80 % by weight of water before cooling below the melting temperature of the polyester to form the final aqueous polyester dispersion of the mixture.
[032] Various melt-kneading processes known in the art may be used. In some embodiments, a kneader, a BANBURY® mixer, single-screw extruder, or a multi-screw extruder, e.g. a twin-screw extruder, may be utilized. A process for producing the polyester aqueous dispersions in accordance with the present disclosure is not particularly limited. For example, an extruder, in certain embodiments, for example, a twin-screw extruder, is coupled to a back pressure regulator, melt pump, or gear pump. Embodiments also provide a dispersing agent reservoir and a water reservoir, each of which includes a pump. In some embodiments, the dispersing agent and water are preheated in a preheater. For example, in a number of embodiments, the polyester, e.g., in the form of pellets, powder, or flakes, can be fed from the feeder to an inlet of an extruder where they are melted. In some embodiments, a dispersing agent can be added to the polyester through and along with the polyester and in other embodiments, the dispersing agent can be provided separately to the extruder. The melted polyester polymers can then be delivered from the mix and convey zone to an emulsification zone of the extruder where an initial amount of water and/or dispersing agent from the water and dispersing agent reservoirs can be added through one or more of an inlet. In some embodiments, the dispersing agent may be added additionally or exclusively to the water stream. In some embodiments, further dilution water may be added via water inlet from a water reservoir to a dilution and cooling zone of the extruder. The polyester aqueous dispersion can be diluted, if desired in the cooling zone. Further dilution may occur a number of times until the desired dilution level is achieved. In some embodiments, water is not added into the twin screw extruder but rather to a stream containing the melt product after the melt product has exited from the extruder. In this manner, steam pressure build-up in the extruder is eliminated and the polyester aqueous dispersion is formed in a secondary mixing device such as a rotor stator mixer.
[033] For the present disclosure, the polyester in the mixture of the polyester aqueous dispersion is in the form of particles (e.g., particles of polyester polymer) having a volume mean diameter (Vmean) of from 20 nm to 2500 nm as measured according to Particle Size Testing provided in the Examples. In an additional embodiment, the particles of the polyester can have a Vmean of from 100 nm to 2000 nm as measured according to Particle Size Testing provided in the Examples. In an additional embodiment, the particles can have a Vmean of from 100 nm to 500 nm as measured according to Particle Size Testing provided in the Examples.
[034] For the present disclosure, the agriculturally active compound is selected from the group consisting of a fungicide, an insecticide, a pesticide, a nematicide, a growth regulator, a safener, a plant activator, biological microbial strains and combinations thereof. The amount of the agriculturally active compound to be used in the AST composition can vary due to the strength of the active ingredient. For the present embodiments, the amount of the agriculturally active compound used in the AST composition is from 5 to 60 wt.% based on the total weight of the AST composition. Preferably, the amount of the agriculturally active compound used in the AST composition is from 10 to 50 wt.% based on the total weight of the AST composition. The amount of the agriculturally active compound in the AST composition can vary depending on the type of seed and the particular agriculturally active compound. [035] Examples of suitable fungicides include those selected from Captan (N- (trichloromethyl)thio-4-cyclohexane-1 ,2-dicarboximide); Thiram (tetramethylthioperoxydicarbonic diamide; Metalaxyl (methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate; Fludioxonil (4-(2,2-difluoro-1 ,3-benzodioxol-4-yl)-1 H-pyrrol-3-carbonitrile; and Oxadixyl (N-(2,6- dimethylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl) acetamide. One skilled in the art will be aware of other beneficial fungicides suitable for combating harmful pathogens which are not only a problem for a particular locale where the coated seed is to be grown but also suitable for the protection of seeds in storage before planting.
[036] Examples of suitable insecticides include those selected from thiamethoxam, azoles such as, for example, triazoles, azines, pyrethroids, organophosphates, caramoyloximes, pyrroles, pyrazoles, pyridines, amidines, halogenated hydrocarbons, and carbamates and combinations and derivatives thereof. Particularly suitable classes of insecticides include insect growth regulators, organophosphates, phenylpyrazoles and pyrethroids. Additional insecticides include those known as terbufos, chlorpyrifos, fipronil, chlorethoxyfos, tefluthrin, fiproles, phenoxycarb, diofenolan, pymetrozine, carbofuran, tebupirimfos, and imidacloprid, including imidacloprid analogs, such as (substituted or unsubstituted) nitro-, oxo-, or cyano-substituted- guanidines, enamines, iminomorpholines, piperazines, iminopiperazines, oxapiperazines, oxadiazines, oxapyridines, diazocyclohexanes, diazolidines, and morpholines.
[037] Examples of suitable nematicides include those selected from abamectin (commercially available from Syngenta as Avicta™), thiodicarb (commercially available from Bayer as Aeris™). Examples of suitable biological microbial strains include those selected from Bacillus amyloliquefaciens, Bacillus thuringiensis, Bacillus subtilis, Pseudomonas fluorescens, Metarhizium Anisopliae, Trichoderma harzianum, Trichoderma virens, Trichoderma asperellum, Beauveria bassiana, Azospirillum brasilense, Gluconacetobacter diazotrophicus, Methylobacterium symbioticum, Brandyrhizobium japonicum.
[038] Examples of suitable growth regulator include those selected from Antiauxins, such as clofibric acid and 2,3,5-tri-iodobenzoic acid; Auxins, such as 4-CPA, 2,4-D, 2,4-DB, 2,4- DEP, Dichlorprop, fenoprop, IAA, IBA, Naphthaleneacetamide, a-naphthaleneacetic acid, 1 - naphthol, naphthoxyacetic acids, MCPA-thioethyl, potassium naphthenate, sodium naphthenate and 2,4,5-T; Cytokinins, such as 2iP, Benzyladenine, 6-benzylaminopurine, kinetin and zeatin; Defoliants, such as calcium cyanamide, dimethipin, endothal, ethephon, merphos, metoxuron, pentachlorophenol, thidiazuron and tributes; Ethylene inhibitors, such as aviglycine, 1- methylcyclopropene; Growth inhibitors, such as abscisic acid, ancymidol, butralin, carbaryl, chlorphonium, chlorpropham, dikegulac, flumetralin, fluoridamid, fosamine, gibberellic acid, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, piproctanyl, prohydrojasmon, propham, 2,3,5-tri-iodobenzoic acid, morphactins [chlorfluren, chlorflurenol, dichlorflurenol, flurenol], tebuconazole, metconazole; Growth retardants, such as chlormequat, daminozide, flurprimidol, mefluidide, paclobutrazol, tetcyclacis and uniconazole; Growth stimulators, such as brassinolide, forchlorfenuron, hymexazol and thiametoxam; Unclassified plant regulators, such as azoxystrobin, benzofluor, buminafos, carvone, ciobutide, clofencet, cloxyfonac, cyanamide, cyclanilide, cycloheximide, cyprosulfamide, epocholeone, ethychlozate, fenridazon, heptopargil, holosulf, inabenfide, karetazan, lead arsenate, methasulfocarb, prohexadione, pydanon, sintofen, sulfometuron, triapenthenol and trinexapac; Plant activators, such as acibenzolar, acibenzolar-S-methyl and probenazole; Salicylates, such as salicylic acid and sodium salicylate; Jasmonates such as jasmonic acid, methyl jasmonate and cis-jasmone. [039] Examples of suitable safeners include those selected from benzoxazine, benzhydryl derivatives, N , N-diallyl dichloroacetamide, various dihaloacyl, oxazolidinyl and thiazolidinyl compounds, ethanone, naphthalic anhydride compounds, and oxime derivatives. [040] Examples of suitable plant activators include those selected from harpin, reynoutria sachalinensis, jasmonate, lipochitooligosaccharides, and isoflavones, among others. [041] The above compounds are listed as examples and are not intended to be an exhaustive list of compounds that can be used in the AST composition of the present disclosure. For the present disclosure, the AST composition can further include any one of a surfactant, a rheology modifier, a cosolvent, a defoamer, dispersing agent for the active ingredient of the AST composition, a pigment or dye and combination thereof. Examples of such additives are known in the art, where examples can be found in US 2018/0303023 A1 and WO 2021/144430A1 , among other places.
[042] The AST composition includes water, where the amount of water can bring the wt.% of the AST composition to 100 wt.%. As noted herein, the polyester aqueous dispersion of the present disclosure can be supplied in the form of a waterborne dispersion, i.e., the polyester aqueous dispersion include water, thereby providing at least a portion of the water for the AST composition.
[043] For the present disclosure, the AST composition can have a viscosity, measured as described in the Examples section herein, of less than 3000 centipoises (cP). For example, the AST composition can have a viscosity in the range of 20 to 3000 cP. Preferably, the AST composition can have a viscosity in the range of 20 to 2000 cP. More preferably, the AST composition can have a viscosity in the range of 500 to 2000 cP. [044] It is possible that AST composition can initially be provided as a concentrate, where either (i) water or (ii) water and the agriculturally active compound are not present in the composition. In the case of (i), water can be subsequently added to the concentrate to provide the AST composition of the present disclosure. In the case of (ii), both water and the agriculturally active compound as desired can be subsequently added to the concentrate to provide the AST composition of the present disclosure.
[045] The polyester dispersion as film forming agent can be incorporated into the AST composition at the beginning or added separately into the AST composition before the seed treatment process.
[046] The present disclosure also provides for an agricultural seed coated with the AST composition as provided herein. For the present disclosure, a coating on the agricultural seed is formed using the AST composition as provided herein.
[047] The present disclosure also provides for a method of forming the coating on the agricultural seed that includes providing the AST composition as provided herein in a container; adding the agricultural seed to the container; coating the agricultural seed with the AST composition; and drying the agricultural seed with the AST composition to form the coating on the agricultural seed. As discussed herein, the method of the present disclosure also includes using a polyester polymer having a glass transition temperature (Tg) of -60 to 20 °C measured according to ASTM E1356-08(2014), as discussed herein, in an AST composition for forming a coating on an agricultural seed. For the present disclosure, the AST composition is the AST composition as provided herein.
[048] The present disclosure also provides a method of forming a coating on an agricultural seed using the AST composition of the present disclosure. For example, the method of forming the coating on the agricultural seed can include providing the AST composition of the present disclosure in a container, adding the agricultural seed to the container; coating the agricultural seed with the AST composition; and drying the agricultural seed with the AST composition to form the coating on the agricultural seed. During the method, the agricultural seed is coated with the AST composition. Upon drying, the resulting product is a coating on an agricultural seed formed using the AST composition of the present disclosure. The agricultural seed can be any of those provided herein, e.g., selected from the group consisting of corn seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugar beet seed, rice, sunflower seed, lettuce seed, and spinach seed. The present disclosure also provides for a method of using the AST composition having the polyester polymer with a glass transition temperature (Tg) of -60 to 20 °C measured according to ASTM £1356-08(2014), where the AST composition forms the coating on the agricultural seed as discussed herein. For the present disclosure, the AST composition is the AST composition as provided herein.
[049] Conventional means of coating may be used for forming the coating on the agricultural seed using the AST composition of the present disclosure. Various coating machines such as drum coaters, Munson Machinery, pan coaters, rotary continuous coaters, and fluidized bed techniques are known and available to one skilled in the art for carrying out the coating process. Other methods, such as spouted beds may also be useful. The agricultural seeds may be pre-sized prior to coating. After coating the agricultural seeds are dried and then optionally sized by transfer to a sizing machine. These machines are known in the art for example, a typical machine used when sizing seed corn in the industry.
[050] Film-forming compositions for enveloping coated seeds are well known in the art, and a film overcoating can be optionally applied to the coated seeds of the present disclosure. The film overcoat can protect the coating formed using the AST composition and optionally allows for easy identification of the treated seeds. In general, additives are dissolved or dispersed in a liquid adhesive, usually a polymer into or with which seeds are dipped or sprayed before drying. Alternatively, a powder adhesive can be used. Various materials are suitable for overcoating including but not limited to, methyl cellulose, hydroxypropyl methylcellulose, dextrin, gums, waxes, vegetable or paraffin oils; water soluble or water disperse polysaccharides and their derivatives such as alginates, starch, and cellulose; and synthetic polymers such as polyethylene oxide, polyvinyl alcohol and polyvinylpyrrolidone and their copolymers and related polymers and mixtures of these.
[051] Further materials may be added to the overcoat including optionally plasticizers, colorants, brighteners and surface-active agents such as, dispersants, emulsifiers and flow agents including for example, calcium stearate, talc and vermiculite. Fluidized bed and drum film coating techniques described above can be employed for film coating.
[052] The AST composition of the present disclosure can further include a filler. The filler can help to increase the loading rate and adjust the release of the agriculturally active compound from the coating formed with the AST composition. The amount of filler used may vary, but generally the filler can be present in the AST composition in a range of 0.005 wt.% to 5 wt.%. Examples of such fillers include, but are not limited to, absorbent or inert fillers such as wood flours, clays, activated carbon, sugars, diatomaceous earth, cereal flours, fine-grain inorganic solids, calcium carbonate and the like. Clays and inorganic solids can include calcium bentonite, kaolin, China clay, talc, perlite, mica, vermiculite, silicas, quartz powder, montmorillonite and mixtures thereof. Sugars may include dextrin and maltodextrin. Cereal flours may include wheat flour, oat flour and barley flour. One skilled in the art will appreciate that this is a non-exhaustive list of materials and that other recognized filler materials may be used depending on the agricultural seed to be coated and the agriculturally active compound used in the AST composition.
[053] The AST composition of the present disclosure can also include one or more of an anti-freeze agent, an anti-foam agent, a thickener and/or a pigment, where the pigment can be in the form of a pigment slurry. The amount of any one of these additional components used may vary, but generally can be present in the AST composition in a range of 0.005 wt.% to 5 wt.%. Examples of anti-freeze agents include, but are not limited to, propylene glycol, ethylene glycol. Examples of anti-foam agents include, but are not limited to, DOW CORNING™ AFE- 0020 Antifoam Emulsion. Examples of thickeners include, but are not limited to, xanthan gum. Examples of pigments include, but are not limited to, Pigment Permanent Red, Pigment Phthalocyanine Blue.
[054] Virtually any agricultural seed can be coated with the AST composition to form a coating on the agricultural seed. For the present disclosure, the agricultural seed can be selected from the group consisting of corn seed (sweet and field), sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugar beet seed, rice, sunflower seed, lettuce seed, and spinach seed. Other suitable agricultural seeds include, but are not limited to, cereals, ornamentals, fruit seeds, cotton, alfalfa, sorghum, rapeseed, Brassica, tomato, bean, carrot, tobacco and flower seeds such as pansy, impatiens, petunia and geranium. The most preferred agricultural seeds include corn and soybean.
[055] Some embodiments of the disclosure will now be described in detail in the following Examples.
Examples
[056] In the Examples, various terms and designations for materials were used including, for example, the following:
Materials employed in the inventive examples (IE) and/or comparative examples (CE) include the following.
Table 1 : Materials and Ingredients
Figure imgf000016_0001
Figure imgf000017_0001
Table 2: Comparative Examples Set 1 : Conventional Film Forming Agents
Figure imgf000017_0002
Table 3: Comparative Examples Set 2: Polymer Dispersions
Figure imgf000018_0001
Table 4: Inventive Examples Set 1 : Polyester aqueous dispersions of Disclosure
Figure imgf000018_0002
Experimental Procedures
Polyester Aqueous Dispersion preparation
Inventive Examples of the polyester aqueous dispersions 1 -4 and Comparative Examples of the Polymer dispersions 1 -3 have the polymer phase components and physical properties as shown in Tables 3, 4 and 5, and were prepared with the raw materials shown in Table 1 using the general procedure, process, and conditions described herein. The thermoplastic polyester resin and dispersant listed for each example in Tables 3, 4 and 5 were fed into a 25 mm diameter twin screw extruder using a controlled rate feeder at the given ratios listed in Tables 3 and 4 at a total feed rate of 75.6 g/min. The polyester base resin and dispersant were forwarded through the extruder and melted to form a liquid melt material where the melt zone temperature in the extruder is set to be 15 °C greater than the melting temperature of the highest melting point component, which is the PVA dispersant when present. An initial amount of water was then added into the extruder at a rate roughly equal to the feed rate of the dispersant material. In a later section of the extruder additional dilution water was then added at a rate to give the composition percentage solids as indicated in Table 5. The extruder speed used was 600 rpm. At the extruder outlet, a backpressure regulator was used to adjust the pressure inside the extruder barrel to a pressure adapted to reduce steam formation (generally the pressure was from 2 MPa to 4 Mpa). Each polyester dispersion exited from the extruder and was filtered first through a 200 micrometer (pm) filter. The resultant filtered polyester dispersion had a solids content measured in weight percent (wt %); and the solids particles of the polyester dispersion has a volume mean particle size measured in microns. The solids content of the polyester dispersion was measured using an infrared solids analyzer, the viscosity of the polyester dispersion was measured using an RV viscometer at 50 rpm using the appropriate spindle for the given viscosity (RV3), and the particle size of the solids particles of the polyester dispersion was measured using a COULTER™ LS-230 particle size analyzer (Beckman Coulter Corporation, Fullerton, CA). The solids content, viscosity, and the average particle size (PS) of the solids particles of the polyester dispersion are indicated in Table 5.
Table 5 - Polyester Aqueous Dispersions (IE) and Polymer Dispersions (CE)
Figure imgf000019_0001
Seed coating sample preparation:
The seed coating compositions seen in Table 6 were based on a commercial Imidacloprid flowable concentrate (Commercial FS, Gaucho® 600, 600 g imidacloprid per liter; Bayer Crop Science AG, Mohnheim, Germany). The seed coating composition of Table 6 was diluted to 80 wt.% by deionized (DI) water (CE-blank), or mixed with a binder plus the DI water, as provided in Table 6, for the Ces and les. The dosage of the binder was 5 wt.% of the total composition. All components were mixed sufficiently and stored at room temperature (22 °C) for at least 24 hours before being applied to the seeds.
Table 6 - Seed Coating Compositions
Figure imgf000019_0002
Figure imgf000020_0001
*AII binder dosages used above are in dry solid wt,%
Seed coating procedure:
A KMC 16-inch Coating Pan (Coating Pan) was used to coat the corn seeds of the present IE and CE. The coater rotation speed was set at 65 rotations per minute (rpm). All the coatings were performed at room temperature (22 °C). The detailed steps of the process are as follows. Corn seeds were measured into a single batch (either 1000 gram (g) or 1300 g). The Coating Compositions for each IE or CE were prepared as described herein after which they were measured to be about 2 % of the mass of the uncoated seeds (either 20 g or 26 g). The coating composition was then drawn into a 50 mL syringe for use in the coating process. Initially the uncoated seeds were loaded into the Coating Pan while off and not turning. The Coating Pan rotational speed was then set at 65 rpm. The Coating Composition for the respective IE or CE was then slowly added to the rotating corn seeds. Once the Coating Composition was added, the corn seeds were allowed to rotate for 5 minutes until there was a uniform layer of Coating Composition on all the seeds. After the coating was completed, the coated corn seeds were placed into a storage jar and allowed to rest at room temperature (22 °C) for 2 days to let the coating dry completely. The weight gain of the seeds after coating was 1 .4 to 2.1 wt.% of the dry seed weight, with minimal loss of coating material to the wall of the Coating Pan.
Characterization
Dust Attrition
The dust attrition measurements were carried out using a ball mill. The details of the material, container, and conditions for use with the ball mill are presented in Table 7 below.
Table 7: Conditions for Dust Measurement Experiments using Ball Mill
Figure imgf000021_0001
The dust measurement process was as follows. Measure 650 g of Test Material, which was formed from approximately 13 grams of the coating corn seed of the IE or CE and 637 g of un-coated corn seeds. Screen the pre-existing fines in the Test Material using a mesh #12 (1 ,68mm) screen and Rotap sieve shaker for 1 minutes without tapping enabled. Separate the fines from the Test Material and record the mass of the Test Material after the first sieve: m(. Load the resulting Test Material (coated corn seeds and un-coated corn seeds) into the milling jar of the ball mill. Place the loaded milling jar onto the roller of the ball mill. Run the ball mill at 65 rpm for 5 minutes. Unloaded the content of the milling jar on a #12 screen as provided above. Shake the screen for 1 minutes using Rotap shaker and record the mass retained, mf. The total dust attrition was calculated according to the Equation (1 ).
%total dust = - - J— Equation (1 ) rrif
Flowability
Flowability was measured using a 3D printing hopper having a valve positioned at its outlet in combination with a high-speed camera to record the discharge of coated seeds from the hopper. The outlet of the hopper had a diameter of 4.2 cm, where the inner diameter of the vertical section of the hopper is 8.9 cm and heigh of the vertical part is 14.6 cm. The angle of conical portions between the outlet and the vertical portions of the hopper were 14.47 degree. The flowability tests were done at room temperature (22 °C). During the filling process, the valve of the hopper remained securely closed. All flowability experiments were conducted with batches containing 750 grams of material, encompassing both seeds and their respective coatings. Once the valve was secured in the closed position, the high-speed camera commences its recording process. Simultaneously, the valve is promptly opened, allowing seeds to flow freely until complete discharge is achieved. Following the conclusion of the discharge, the image recording process is temporarily paused. The total discharged time required for the granules to completely exit the hopper was calculated with an accuracy of up to 0.001 seconds. Consequently, a determine of the average mass flow rate associated with each specific coating can be calculated with Equation (2).
Mass flow rate = ™ Equation (2)
Where m is the total mass of the seeds and t is the time used from beginning to conclusion of the discharge.
Tested Property Results
As discussed in the detailed description, acrylic latex and polyvinyl alcohol have long been used as film forming agents in the seed coating industry to reduce dust generation and improve other properties such as flowability. Acrylic latex has been seen as the workhorse due to its performance, processibility and low cost. However, under the unfolding microplastic restrictions, acrylic latex falls into the microplastic definition and the use of it will likely be restriction in areas including but not limited to agricultural application (e.g., coatings for agricultural seeds). Polyvinyl alcohol or PVOH, however, may be deregulated from this restriction due to its water solubility. Yet, the performance of PVOH as film forming agent is inadequate. Plus, the viscosity of PVOH goes up quickly when concentration passes over 10 wt.% in water at room temperature. Ideally for a good film forming agent, the viscosity should be below 3000 cP for good pumpability at a reasonable solid content (e.g., 30-60 wt.%).
With respect to the present examples, the corn seeds coated with the seed coating compositions of the CEs seen in Table 5 initially showed good coverage, except for CE-PVOH1 and CE-PVOH2. This may have been partially due to the high viscosity profile of CE-PVOH1 and CE-PVOH2, which negatively impact the flow of the aqueous composition during the coating process. All polyester aqueous dispersions (both IE and CE) provided coverage that was comparable to the blank sample (CE-Blank) and the sample using commercial acrylic latex as film former (CE-Acrylic1 ). For the dust attrition test described herein the appearance of the coated corn seeds after the test were visually rated and compared (Table 8 and Table 9). Without any film forming agent, the coating of CE-blank became thin and crumbled after attrition. The addition of commercial acrylic latex CE-Acrlyic1 did not improve the attrition. Even worse failure was observed for CE- PVOH1 and CE-PVOH2, where corn seed skin was exposed in many seeds after attrition. Surprisingly, the coated seeds in inventive examples all showed great resistance to attrition, with only minimal loss of coating mainly at the crown area of the seed. Moreover, rather than crumbled surface like the blank, the coated surfaces of all inventive samples remain smooth and glossy, indicating minimal dust generation during attrition.
Table 8. Appearance rating after attrition.
Figure imgf000023_0001
Table 9. Rating criterion for appearance after attrition.
Figure imgf000023_0002
The results of the dust measurement process are seen in FIG. 1 . For quantitative comparation, dust was separated from the seeds by sieving, as described herein, and weight loss and weight loss percentage of the coating were recorded (Figure 8). Surprisingly, neither the acrylic latex nor the PVOH provided protection to the coated seed in terms of attrition and dust control. The weight loss by percentage of CE-acrylic1 and CE-PVOH1 and PVOH2 are even higher than CE-Blank.
For the inventive examples, IE-PD1 to IE-PD4, which are polycaprolactone dispersions, the coating loss after attrition was 0.6 to 3 times lower comparing to CE-Blank. FIG. 2 shows the flowability of treated seeds containing different film forming agents. Without wishing to be bound by theory, it is believed that the polyester particles may act as a lubricative cushion on the surface of the seed and/or in the coating matrix to minimize external and internal friction, and thus reduce the attrition and dust generation. In addition, it is believed that the polyester particles may fill “gaps” between the otherwise loosely connected pesticide particles and bind them into a more integrated film. As a result, the inventive sample showed significantly better flow than both blank and acrylic latex containing coating.
The type of polyester and the polyester particle size in the dispersion are of interest. It is believed that the low Tg polyester (softer particles) can better dissipate the impacts and friction as the coated seeds contact each other. In contrast, dispersions with too high particle size may not be as effective due to lower number of total particles present in the coating. Low Tg (- 60 °C) polycaprolactone was chosen and all inventive examples have volume-mean particle sizes in the range of 200 to 1000 nm. To further verify this hypothesis, a PBS dispersion (CE-PD1 , Vmean of 2450 nm) was prepared and tested against two other dispersions using PLA as the polyester (CE-PD2 and CE-PD3). Although PBS is a relatively soft polyester, the dispersion did not improve the attrition significantly, which may be attributed to the larger particle size. On the other hand, both CE-PD2 and CE-PD3 contributed to negative attrition resistance compared with CE-Blank, which may be due to the polymer’s higher glass transition temperature (Tg of 60 °C).
The results show that the polyester aqueous dispersion of the present disclosure with proper glass transition temperature and particle size range can serve as an excellent additive to seed coating compositions to reduce dust and attrition.
Particle Size Testing
Particle size was measured by laser diffraction using a COULTER™ LS-230 or LS-320 particle size analyzer (Beckman Coulter Corporation, Fullerton, CA) with the particle (sample) refractive index set to 1 .5 and is reported as the volume mean diameter (Vmean) of the polyester particles.
Glass Transition Temperature
Glass transition temperature was measured according to ASTM E1356-08(2014). Viscosity
Viscosity was measured using a Brookfield DVII+ instrument with RV3 spindle.
Measurements were taken at room temperature (22 °C). The spindle is submerged in the dispersion to the level line on the spindle at an appropriate rpm to obtain a stable viscosity reading for 15 seconds.

Claims

What is Claimed is:
1 . An aqueous seed treatment composition for forming a coating on an agricultural seed, comprising: a) 0.5 to 40 weight percent (wt.%) of a polyester aqueous dispersion, wherein the wt.% of the polyester aqueous dispersion is based on the total weight of the aqueous seed treatment composition, and wherein the polyester aqueous dispersion formed with: a mixture comprising:
30 to 95 wt.% of a polyester; and
5 to 70 wt.% of a dispersing agent, where the wt.% of the polyester and the dispersing agent are based on the total weight of the mixture; and water so that the polyester aqueous dispersion has 20 to 60 wt.% solids content based on the total weight of the polyester aqueous dispersion; and b) 5 to 60 wt.% of an agriculturally active compound, wherein the wt.% of the agriculturally active compound is based on the total weight of the aqueous seed treatment composition; and c) water, where the amount of water brings the wt.% of the aqueous seed treatment composition to 100 wt.%.
2. The aqueous seed treatment composition of claim 1 , wherein the polyester has a glass transition temperature (Tg) of - 60 to 20 °C measured according to ASTM £1356-08(2014).
3. The aqueous seed treatment composition of claim 2, wherein the polyester has a glass transition temperature (Tg) of - 60 to 0 °C measured according to ASTM £1356-08(2014).
4. The aqueous seed treatment composition of any one of claims 1 -3, wherein the mixture is in the form of particles having a volume mean diameter of from 20 nm to 2500 nm as measured according to Particle Size Testing provided in the Examples.
5. The aqueous seed treatment composition of claim 4, wherein the particles have a volume mean diameter of from 100 nm to 2000 nm as measured according to Particle Size Testing provided in the Examples.
6. The aqueous seed treatment composition of any one of claims 1 -5, wherein the polyester is selected from the group consisting of polycaprolactone, poly(3-hydroxybutyrate-co- 3-hydroxyhexanoate), poly(3-hydroxybutyrate-co-3-hydroxy valerate), poly(3-hydroxy valerate), poly(3-hydroxybutyrate), polyhydroxyalkanoate, polybutylene adipate terephthalate, polyethylene succinate), polypropylene succinate), poly(butylene succinate), poly(butylene succinate adipate), and combinations thereof.
7. The aqueous seed treatment composition of any one of claims 1 -6, wherein the dispersing agent is selected from the group consisting of polyvinyl alcohol, fatty alcohol ethoxylates, ethylene oxide/propylene oxide block copolymers, salts of fatty acids, polyacrylate copolymers, polysaccharide derivatives, lignin derivatives and combinations thereof.
8. The aqueous seed treatment composition of any one of claims 1 -7, wherein the polyester and the dispersant of the polyester aqueous dispersion have a wt.% ratio of 1 :2.3 to 19:1.
9. The aqueous seed treatment composition of any one of claims 1 -8, wherein the mixture includes:
70 to 95 wt.% of the polyester; and
5 to 30 wt.% of the dispersing agent.
10. The aqueous seed treatment composition of any one of claims 1 -9, wherein the aqueous seed treatment composition includes: a) 10 to 30 wt.% of the polyester aqueous dispersion; and b) 20 to 40 wt.% of the agriculturally active compound; and c) water, where the amount of water brings the wt.% of the aqueous seed treatment composition to 100 wt.%.
11 . The aqueous seed treatment composition of any one of claims 1 -10, wherein the agriculturally active compound is selected from the group consisting of a fungicide, an insecticide, a pesticide, a nematicide, a growth regulator, a safener, a plant activator, biological microbial strains, and combinations thereof.
12. The aqueous seed treatment composition of any one of claims 1 -1 1 , wherein the aqueous seed treatment composition further includes any one of a surfactant, a defoamer, a dye and combination thereof.
13. An agricultural seed coated with the aqueous seed treatment composition of any one of claims 1 -12.
14. A coating on an agricultural seed formed using the aqueous seed treatment composition of any one of claims 1-12.
15. The coating of claim 14, wherein the agricultural seed is selected from the group consisting of corn seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugar beet seed, rice, sunflower seed, lettuce seed, and spinach seed.
16. A method of forming a coating on an agricultural seed, comprising: providing the aqueous seed treatment composition of any one of claims 1 -12 in a container; adding the agricultural seed to the container; coating the agricultural seed with the aqueous seed treatment composition; and drying the agricultural seed with the aqueous seed treatment composition to form the coating on the agricultural seed.
17. A method of using a polyester polymer having a glass transition temperature (Tg) of -60 to 20 °C measured according to ASTM E 1356-08(2014) in an aqueous seed treatment composition for forming a coating on an agricultural seed.
18. The method of claim 18, wherein the aqueous seed treatment composition is the aqueous seed treatment composition of any one of claims 1 through 12.
PCT/US2024/049398 2023-10-11 2024-10-01 Aqueous seed treatment compositions and coatings therefrom Pending WO2025080464A1 (en)

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