Slurry compositions comprising modified maleated natural oil containing a lactam moiety, salts, method of preparation, and applications thereof
The development of a slurry composition using maleated natural oils reacted with lactam moieties and dispersed particles addresses the insolubility and non-dispersibility issues of natural oils, improving their solubility and stability for various applications.
Patent Information
- Application Number
- PCT/US2024/046067
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-09-11
- Filing Date
- 2024-09-11
- Publication Date
- 2025-03-20
AI Technical Summary
Natural oils, including their maleated counterparts, exhibit limitations such as insolubility and non-dispersibility in water and alcohols, which complicates their formulation and application in various compositions.
A slurry composition comprising a reaction product of maleated natural oils and a lactam moiety with hydroxyl, thiol, or amine functional groups, along with a dispersed particle, is developed to enhance solubility and dispersibility.
The proposed slurry composition improves the solubilization capability and stability of maleated natural oils, reducing phase separation and enhancing their performance in diverse applications.
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Abstract
Description
SLURRY COMPOSITIONS COMPRISING MODIFIED MALEATED NATURAL OIL CONTAINING A LACTAM MOIETY, SALTS, METHOD OF PREPARATION, AND APPLICATIONS THEREOF FIELD OF THE INVENTION
[0001] The presently disclosed process(es), procedure(s), method(s), product(s), result(s), and / or concept(s) (collectively referred to hereinafter as the “present disclosure or invention”) relates to slurry compositions containing lactam based maleated natural-oil products, and the use of the slurry compositions in various applications. BACKGROUND OF THE INVENTION
[0002] Modified natural oils can be incorporated into a wide variety of compositions. Such compositions include, but are not limited to, personal care (e.g., hair care, sun care, skin care, oral care), adhesives, coatings, paints, electronics, household, industrial and institutional (HI&I) compositions, inks, membranes, metal working fluids, oilfield chemicals, plastics and plasticizers, textiles, industrial products, biocides, pharmaceuticals / nutritional, and agrochemical compositions.
[0003] Natural oils are useful for synthesizing renewable compounds such as polymers, plastics, and plasticizers, which compounds are useful in a variety of agricultural compositions. A difficulty with utilizing natural oils is that they are blends of triglycerides containing varying degrees of unsaturated groups, which unsaturated groups are relatively unreactive. To make these natural oils reactive, these unsaturated groups are generally chemically modified to make them reactive. For example, these unsaturated groups can be reacted to provide epoxide functional groups or succinic anhydride functional groups. Despite these chemical modifications, the maleated natural oils can still exhibit limited properties such as insolubility or non-dispersibility in water and alcohols. Accordingly, there is a need for further modified maleated natural oils which do not exhibit the limited properties of maleated natural oils.
[0004] Despite the renewability, biodegradability, sustainability, and beneficial functions provided by natural fatty acids, natural oils and their maleated counterparts, they exhibit properties that can limit their application. For example, maleated soybean oil is insoluble and non-dispersiblein water or alcohols. As a result, these oils may tend to exude or phase-separate from formulated compositions. This feature makes their formulation more difficult, often requiring additional ingredients to facilitate solutions, emulsions, or dispersions. Natural and maleated natural oils may not impart the desired property needed in end-uses, such as solubilization capability, glass transition, flexibility, shine, and / or plasticization. Consequently, the performance (including, but not limited to stability, resistance to phase separation, absorption, clean-up, solubility potential, staining potential, lubrication, film formation, uniformity of spreading, comedogenic tendency, ease of removal), may be less than desired. Finally, although such natural oils are an important renewable material, they are not always the formulator's first choice, and, in fact, often are not considered at all.
[0005] Modified natural oils are natural oils that have been chemically functionalized by the chemical addition of epoxide (oxirane) and succinic anhydride functional groups. Examples include epoxidized and maleated soybean oil and linseed oil, unsaturated natural oils lend themselves to this chemical functionalization.
[0006] Dispersing agents are commonly used to wet out the dry filler during mixing of slurry compositions, reduce the viscosity and make the formulation more workable. Numerous dispersing agents are available in the market. One such example are pigments which are traditionally milled and sold as powders or as dispersion in solvent.
[0007] US granted Patent No: 9809538B2 describes a modified natural compound synthesized from epoxidized natural fatty acid, maleated natural fatty acid, epoxidized natural oil, or maleated natural oil; and lactam compound with hydroxyl(s) to form e.g., adhesive or beverage composition.
[0008] PCT Pub. Nos: 2019113068A1 and 2005071050A1 describe a technology related to metalworking fluids comprising maleated soybean oil derivatives.
[0009] PCT Pub. No: 2021252426A1 assigned to Sun Chemical Corporation discloses a solid pigment dispersion comprising one or more pigments approved for cosmetic use and a combination of one or more oils and / or waxes that are plant-based wherein the dispersion is in the form of a dry powder.
[0010] US granted Patent No: 5733970A discloses an aqueous dispersed, epoxy crosslinked maleated oil (maleated glyceride oil) microgel polymers for protective coatings.
[0011] US granted patent No: 10836910B2, assigned to Sherwin Williams Co., discloses concentrate for use in the manufacture of fluid colorants or finished coating compositions, wherein at least 95 wt.% of the concentrate is a mixture of (i) solid pigment particles with (ii) a non- volatilizing, reactive liquid diluent having a viscosity less than 1,000 cps, and comprising at least 60 wt.% of one or more molecular species having at least three reactive unsaturated sites and having a molar equivalent weight per reactive unsaturated site that is less than 500 grams (g), wherein when the reactive liquid diluent does not by itself stably disperse the pigment particles then the concentrate also contains (iii) one or more pigment wetting or dispersing agents.
[0012] Chinese patent 105977022A discloses a nanoscale nickel metal electrode sizing for multi- layer ceramic capacitance, it is characterised in that be by quality with following raw material Percentage mix forms: nanoscale nickel powder 56%, polyvinyl alcohol 3%, butyl carbitol 21%, MgCO3Nano powder 20%.
[0013] Chinese patent 105321711B discloses an electrocondution slurry, which is characterized in that the electrocondution slurry is to contain conductive metal powder, ceramic powders, resin. The electrocondution slurry for multi-layered ceramic device of adhesive, dispersing agent and organic solvent.
[0014] Japanese patent JP6942317B2 discloses a method of manufacturing a slurry containing at least acetylene black and a dispersion medium, rheometer: MARSIII (manufactured by Thermo Fisher Scientific), Sensor: shear rate viscosity measured using is minimized value DC60 / 2 A method for producing a slurry containing at least acetylene black and a dispersion medium, which comprises performing a dispersion step until the value becomes 100 to 1000s -1.
[0015] There is a need in the art for a dispersion composition for use in ceramic slurries, personal care and coatings which are prepared from materials that are renewable, natural, and biodegradable, having different and controllable chemical, physical, and / or mechanical properties such that the limitations found in natural oils are minimized or eliminated.SUMMARY OF THE INVENTION
[0016] The primary aspect of the present application is to provide a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, and (ii) a dispersed particle.
[0017] Another aspect of the present application is to provide a slurry composition comprising: (i) a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality, and (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and the group; Q is selectedfrom the group consisting of functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms, and (ii) a dispersed particle.
[0018] One more aspect of the present application is to provide a slurry composition comprising: a reaction product of (A) a maleated soybean oil, and (B) 1-(2-hydroxyethyl)-2-pyrrolidone;wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2- hydroxyethyl)-2-pyrrolidone moieties.
[0019] Another aspect of the present application is to provide a slurry composition comprising: a reaction product of (A) a maleated soybean oil; and (B) 1-(2-aminoethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)- 2-pyrrolidone moieties.
[0020] Another aspect of the present application is to provide a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base, and (ii) a dispersed particle.
[0021] One more aspect of the present application is to provide a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base, and (ii) a dispersed particle.
[0022] Another aspect of the present application is to provide a slurry composition, wherein the dispersed particle is selected from the group consisting of alumina, alumina oxide hydroxide, SiO2, BaSO4, TiO2, SnO2, CeO2, ZrO2, BaTiO3, Y2O3, B2O3, carbon nanotube, ZnO, aluminum-doped lithium lanthanum zirconate (Al-doped LLZO), and combinations thereof.
[0023] One more aspect of the present application is to provide a slurry composition useful as a component in pharmaceutical compositions, skin care compositions, oral care compositions, hair care compositions, energy compositions, construction compositions, biocidal compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, homecare compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, metal working fluids, ceramic coating compositions, and disinfecting compositions.
[0024] Another aspect of the present application is to provide a ceramic coated separator for an energy storage device comprising: (i) a slurry composition, wherein the dispersed particle is a ceramic particle and wherein the slurry composition is a ceramic slurry composition and (ii) a separator, wherein the slurry composition is in contact with at least a portion of the separator.
[0025] Another aspect of the present application provides a battery comprising: at least one coated separator; at least one cathode; and at least one anode.
[0026] One more aspect of the present application provides a method of making a ceramic coated separator comprising: a) creating a ceramic slurry coating on a separator by coating the ceramic slurry composition on the separator by a method selected from the group consisting of doctor blading, bar coating, slot-die coating, dip coating, spin coating, direct gravure, reverse coating and combinations thereof; b) creating a ceramic coating on the separator by drying the ceramic slurry coating of step (a) on the separator by using an energy source selected from the group consisting of heat, ultraviolet (UV), light emitting diode (LED), electron beam (EB) and combinations thereof; and c) conditioning the ceramic coating of step (b) at a temperature. DETAILED DESCRIPTION OF THE INVENTION
[0027] What is herein described is a slurry composition comprising modified maleated natural oils and application of these slurry compositions in active pharmaceutical compositions, skin care compositions, oral care compositions, hair care compositions, energy compositions, construction compositions, biocidal compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, homecare compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, metal working fluids, ceramic coating composition, and disinfecting compositions.
[0028] Unless otherwise defined herein, technical terms used in connection with the disclosed and / or claimed inventive concept(s) shall have the meanings that are commonly understood by those of ordinary skill in the art. Further, unless otherwise required by context, singular terms shall include pluralities and plural terms shall include the singular.
[0029] The singular forms "a," "an," and "the" include plural forms unless the context clearly dictates otherwise specified or clearly implied to the contrary by the context in which the referenceis made. The term “comprising” and “comprises of” includes the more restrictive claims such as “consisting essentially of” and “consisting of”.
[0030] For purposes of the following detailed description, other than in any operating examples, or where otherwise indicated, numbers that express, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term "about". The numerical parameters set forth in the specification and attached claims are approximations that may vary depending upon the desired properties to be obtained in carrying out the invention.
[0031] All percentages, parts, proportions and ratios as used herein, are by weight of the total composition, unless otherwise specified. All such weights as they pertain to listed ingredients are based on the active level and, therefore do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified.
[0032] All publications, articles, papers, patents, patent publications, and other references cited herein are hereby incorporated herein in their entirety for all purposes to the extent consistent with the disclosure herein.
[0033] As used herein, the words “comprising” (and any form of comprising, such as “comprise” and “comprises”), “having” (and any form of having, such as “have” and “has”), “including” (and any form of including, such as “includes” and “include”) or “containing” (and any form of containing, such as “contains” and “contain”) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.
[0034] The term “each independently selected from the group consisting of” means when a group appears more than once in a structure, that group may be selected independently each time it appears.
[0035] The term “polymer” refers to a compound comprising repeating structural units (monomers) connected by covalent chemical bonds. Polymers may be further derivatized, crosslinked, grafted or end-capped. Non-limiting examples of polymers include copolymers, terpolymers, tetrapolymers, quaternary polymers, and homologues. The term “copolymer” refers to a polymer consisting essentially of two or more different types of monomers polymerized to obtain said copolymer.
[0036] The term “reaction product” refers to a substance produced from a chemical reaction of one or more reactant substances.
[0037] The term “alkyl” refers to a functionalized or unfunctionalized, monovalent, straight- chain, branched-chain, or cyclic C1-C60 hydrocarbyl group optionally having one or more heteroatoms. In one non-limiting embodiment, an alkyl is a C1-C45 hydrocarbyl group. In another non-limiting embodiment, an alkyl is a C1-C30hydrocarbyl group. Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n- hexyl, n-heptyl, n-octyl, 2-ethylhexyl, tert-octyl, iso-norbornyl, n-dodecyl, tert-dodecyl, n- tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The definition of “alkyl” also includes groups obtained by combinations of straight-chain, branched-chain and / or cyclic structures.
[0038] The term “aryl” refers to a functionalized or unfunctionalized, monovalent, aromatic hydrocarbyl group optionally having one or more heteroatoms. The definition of aryl includes carbocyclic and heterocyclic aromatic groups. Non-limiting examples of aryl groups include phenyl, naphthyl, indenyl, indanyl, azulenyl, fluorenyl, anthracenyl, furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 2-pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl, 1,3,4-thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,3,5-trithianyl, indolizinyl, indolyl, isoindolyl, 3H-indolyl, indolinyl, benzo[b]furanyl, 2,3-dihydrobenzofuranyl, benzo[b]thiophenyl, 1H-indazolyl, benzimidazolyl, benzthiazolyl, purinyl, 4H-quinolizinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 1,8-naphthridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxyazinyl, pyrazolo[1,5-c]triazinyl, and the like.
[0039] The term “aralkyl” refers to an alkyl group comprising one or more aryl substituent(s) wherein "aryl" and "alkyl" are as defined above. Non-limiting examples of aralkyl groups include benzyl, 2-phenyl-ethyl, 3-phenyl-propyl, 4-phenyl-butyl, 5-phenyl-pentyl, 4-phenylcyclohexyl, 4- benzylcyclohexyl, 4-phenylcyclohexylmethyl, 4-benzylcyclohexylmethyl, and the like.
[0040] The term “alkaryl” refers to an aryl group comprising one or more alkyl substituent(s), wherein “alkyl” and “aryl” are as defined above. Non-limiting examples of alkaryl groups include 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-nonylphenyl,dimethylphenyl, or trimethylphenyl, and the like, which may optionally be further substituted on one or more of the carbon atoms of the radical.
[0041] The term “alkylene” refers to a functionalized or unfunctionalized, divalent, straight- chain, branched-chain, or cyclic C1-C40 hydrocarbyl group optionally having one or more heteroatoms. In one non-limiting embodiment, an alkylene is a C1-C30 group. In another non- limiting embodiment, an alkylene is a C1-C20group. Non-limiting examples of alkylene groups include:
[0042] The term “arylene” refers to a functionalized or unfunctionalized, divalent, aromatic hydrocarbyl group optionally having one or more heteroatoms. The definition of arylene includes carbocyclic and heterocyclic groups. Non-limiting examples of arylene groups include phenylene, naphthylene, pyridinylene, and the like.
[0043] The term "branched and unbranched alkyl groups" refers to alkyl groups, which may be straight chained or branched. Branched groups include isopropyl, tert-butyl, and the like.
[0044] The term “dispersing agent” as used herein refers to a “substance added to a suspension to improve the separation of particles and to prevent settling or clumping.
[0045] The term “heteroatom” refers to oxygen, nitrogen, sulfur, silicon, phosphorous, or halogen. The heteroatom(s) may be present as a part of one or more heteroatom-containing functional groups. Non-limiting examples of heteroatom-containing functional groups include ether, hydroxy, epoxy, carbonyl, carboxamide, carboxylic ester, carboxylic acid, imine, imide, amine, sulfonic, sulfonamide, phosphonic, and silane groups. The heteroatom(s) may also be present as a part of a ring such as in heteroaryl and heteroarylene groups.
[0046] The term “maleated natural oil”, as used herein, refers to natural oil contains at least one or more maleated functionalities. Accordingly, the term "maleation" or "maleated" as used hereafter should be understood to mean "functionalization" insofar as the use of functionalizing reagents other than maleic anhydride are contemplated for use in the process of the invention.
[0047] The term “moiety” or “moieties” refer to a part or a functional group(s) of a molecule.
[0048] The term “natural oil” refers to compounds comprising triglycerides and may contain varying levels of fatty acids, monoglycerides, diglycerides and triglycerides refer to oil derived from plants or animal sources. Natural oils also include fatty acid glyceryl esters, which are synthesized by reacting glycerol with 1, 2, or 3 molar equivalents of a fatty acid or a mixture of fatty acids. These compounds can be mono, di or triglycerides of a single fatty acid or a mixture of fatty acids.
[0049] The term, “maleated functionality” refers to moieties formed by attaching maleic anhydride to unsaturated fatty acyl chains, found in natural oils, by ene reaction. “Maleated functionality” includes but is not limited to the cyclic anhydride form (I), the diacid form (II), the disodium dicarboxylate form (III), other dicarboxylate salt forms, and the half ester form (IV). Since the carbon-carbon double bond of maleic anhydride becomes a saturated carbon-carbon single bond during the ene reaction, the “maleated functionality” pictured in I, II, III and IV mightalso be called by one of ordinary skill in the art succinic anhydride, succinic acid, succinate salt or succinate half ester functionality.
[0050] The maleation reaction in natural oil can occur under heating in three different ways. The first one is known as “Ene” reaction (reaction between an allylic moiety and an enophile in a pericyclic reaction), obtaining a triglyceride structure with anhydride moieties (succinic anhydride). The second one is a radical addition, which consumes a double bond in the fatty acid, incorporating the succinic anhydride into the natural oil structure. The final reaction is also a radical addition that incorporates the maleic anhydride into the natural oil structure without consuming C=C bonds (fatty acid chain and maleic anhydride); this reaction occurs due to abstraction of hydrogen atoms from two alkenes groups.
[0051] As a non-limiting, illustrative example, the maleation reaction may be performed at elevated temperatures, such as a temperature between about 150 °C and about 300 °C, alternatively, between about 170 °C and about 230 °C, or alternatively, between about 200 °C and about 220 °C. The reaction time may be between about 0.5 hours and about 14 hours. In one embodiment, the reaction time is between about 1 hour and about 5 hours and, in another embodiment, between about 2 hours and about 6 hours and, in another embodiment, between about 6 hours and about 10 hours.
[0052] The term “base”, as used herein, refers to any substance which can alter the pH of a solution from a neutral pH of 7.0 to a basic pH (i.e., 7.1 to 14). Typically, a base is a substance of a large class of compounds with one or more of the following properties: bitter taste, slippery feeling in solution, ability to turn litmus blue and to cause other indicators to take on characteristic colors, ability to react with (neutralize) acids to form salts includes both organic base or an inorganic base and mixtures thereof.
[0053] The term “organic base”, as used herein, includes ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.
[0054] The term “inorganic base”, as used herein, includes oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.
[0055] The term “alkali metal base” includes oxides, hydroxides, carbonates, and bicarbonates of sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr).
[0056] The term “alkali-earth metal base” includes oxides, hydroxides, carbonates, or bicarbonates of beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra).
[0057] The term “transition metal base” includes oxides, hydroxides, carbonates, and bicarbonates of scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), cadmium (Cd), hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), mercury (Hg), rutherfordium (Rf), dubnium (Db), seaborgium (Sg), bohrium (Bh), hassium (Hs), meitnerium (Mt), darmstadtium (Ds) and roentgenium (Rg).
[0058] The term “battery” used herein include a single electrochemical cell, or unicell, and / or one or more electrochemical cells connected in series and / or in parallel as known by those of skill in the art. Furthermore, the term “battery” includes, but is not limited to, rechargeable batteries, secondary batteries, lithium-ion battery and / or electrochemical cells.
[0059] The term “lithium-ion battery” used herein, is used interchangeably with Li-ion battery, and lithium polymer battery.
[0060] The term “functionalized” with reference to any moiety refers to the presence of one or more functional groups in the moiety. Various functional groups may be introduced in a moietyby way of one or more functionalization reactions known to a person having ordinary skill in the art. Non-limiting examples of functionalization reactions include: alkylation, epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Canizzaro reaction, Mannich reaction, Clasien condensation, Suzuki coupling, and the like. In one non-limiting embodiment, the term “functionalized” with reference to any moiety refers to the presence of one more functional group selected from the group consisting of alkyl, alkenyl, hydroxyl, carboxyl, halogen, alkoxy, amino, imino, and combinations thereof, in the moiety.
[0061] As used herein, the term "hydrophilic" means that the compound has an affinity for water, whereas "hydrophobic" means not having an affinity for water.
[0062] The terms are relative terms, where a hydrophilic moiety it has a higher affinity for water than a hydrophobic moiety, but the hydrophilic moiety may or may not be completely water soluble.
[0063] Likewise, hydrophobic moieties have less affinity for water than hydrophilic moieties, but the hydrophobic moieties may not necessarily be water-repellant. While hydrophilic moieties have an affinity for water and other polar solvents, hydrophobic moieties tend to have an affinity for oils, fats, and other non-polar solvents.
[0064] The term “hydrocarbyl” includes straight-chain and branched-chain alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl groups, and combinations thereof with optional heteroatom(s). A hydrocarbyl group may be mono-, di- or polyvalent and have carbon chains contain at least 2 carbon atoms and preferably 2 to 100 carbon atoms.
[0065] One embodiment of the present invention relates to a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol, or amine functional group, and (ii) a dispersed particle.
[0066] Non-limiting examples of maleated natural oil used as reaction component (A) of the present invention include maleated avocado oils, maleated coconut oils, maleated corn oils,maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof.
[0067] According to one more embodiment of the present invention, the maleated natural oil is a maleated soybean oil.
[0068] According to another embodiment, the present invention relates to a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality, and (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and the group; Q is selectedfrom the group consisting of functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl andaralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms, and (ii) a dispersed particle.
[0069] According to one more embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q isselected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
[0070] According to another embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
[0071] According to one more embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein Q is selected from the group consisting of functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
[0072] According to one embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
[0073] According to another embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.
[0074] According to one more embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–).
[0075] According to another embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is1-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure: .
[0076] According to one more embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-aminoethyl)-2-pyrrolidone, having the structure:
[0077] According to another embodiment, the present invention discloses a slurry composition comprising: (i) a reaction product of: (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; and (B) 1-(2-hydroxyethyl)-2-pyrrolidone, and (ii) a dispersed particle, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2- hydroxyethyl)-2-pyrrolidone moieties.
[0078] According to another embodiment, the present invention provides a slurry composition comprising: (i) a reaction product of: (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; and (B) 1-(2-aminoethyl)-2-pyrrolidone, and (ii) a dispersed particle, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2- aminoethyl)-2-pyrrolidone moieties.
[0079] In one non-limiting embodiment, the present invention provides a slurry composition comprising (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) 1-(2-hydroxyethyl)-2-pyrrolidone; and (ii) a dispersed particle, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2- hydroxyethyl)-2-pyrrolidone (HEP) moieties comprising one or more structure(s) selected from:O
[0080] In one non-limiting embodiment, the present invention provides a slurry compositioncomprising: (i) a reaction product of: (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; and (B) 1-(2-aminoethyl)-2-pyrrolidone; and (ii) a dispersed particle, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2- aminoethyl)-2-pyrrolidone moieties comprising one or more structure(s) selected from:wherein, R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms.
[0081] In one non-limiting embodiment, the present invention provides a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base, and (ii) a dispersed particle.
[0082] In one non-limiting embodiment, the present invention provides a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q isselected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base; and (ii) a dispersed particle.
[0083] According to one more embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein Q is selected from the group consisting of functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
[0084] According to another embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.
[0085] In one non-limiting embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure:
[0086] In one non-limiting embodiment, the base (C) is selected from the group consisting of inorganic bases, organic bases, and combinations thereof.
[0087] In one non-limiting embodiment, the inorganic base is selected from the group consisting of oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.
[0088] In one non-limiting embodiment, the organic base is selected from the group consisting of ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.
[0089] In one non-limiting embodiment, the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.
[0090] In one non-limiting embodiment, the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.
[0091] In one non-limiting embodiment, the transition metal is selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper,zinc, yttrium zirconium, niobium, molybdenum, technetium, ruthenium, rhodium, palladium, silver, cadmium, hafnium, tantalum, tungsten, rhenium, osmium, iridium, platinum, gold, mercury, rutherfordium, dubnium, seaborgium, bohrium, hassium, meitnerium, darmstadtium, roentgenium, and mixtures thereof.
[0092] In one non-limiting embodiment, the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.
[0093] In one non-limiting embodiment, the present invention provides a slurry composition comprising (i) a reaction product of: (A) a maleated soybean oil; (B) 1-(2-hydroxyethyl)-2- pyrrolidone; and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium; and (ii) a dispersed particle, wherein the reaction product is a sodium salt of maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)-2-pyrrolidone moieties.
[0094] In one non-limiting embodiment, the present invention provides a slurry composition comprising (i) a reaction product of: (A) a maleated soybean oil; (B) 1-(2-hydroxyethyl)-2- pyrrolidone and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium; and (ii) a dispersed particle.
[0095] Particularly, the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)-2-pyrrolidone moieties, comprising one or more structure(s) selected from:
[0096] In another non-limiting embodiment, the present invention provides a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base, and (ii) a dispersed particle.
[0097] In one non-limiting embodiment, the present invention provides a slurry compositioncomprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, having the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and, (D) optionally, a base; and (ii) a dispersed particle.
[0098] According to one more embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein Q is selected from the group consisting of functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
[0099] According to another embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.
[0100] In one non-limiting embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure:
[0101] In one non-limiting embodiment, the functionalized or unfunctionalized moiety (C) is a hydrophobic moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, with or without additionalheteroatoms, containing from about 6 to about 36 carbon atoms; ; unsubstituted and substituted polyols, with or without additional heteroatoms, containing from about 37 to about 60 carbon atoms; silicon-based compounds, and combinations thereof.
[0102] In one non-limiting embodiment, the functionalized or unfunctionalized moiety (C) is a hydrophilic moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, with or without additional heteroatoms, containing from about 1 to about 5 carbon atoms; ; unsubstituted and substituted polyols, with or without additional heteroatoms, containing from about 2 to about 36 carbon atoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.
[0103] In one non-limiting embodiment, the silane is functionalized with an alcohol, an amine, or combinations thereof.
[0104] In one non-limiting embodiment, the hydrophobic moiety is that of an alcohol selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl-1-octanol, 2-hexyl-1-decanol, 2-octyl-1- dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1-hexadecanol, 2-hexadecanol, 1-octadecanol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4-methyl-1-pentanol, behenyl alcohol, 1- naphthalenemethanol, benzyl alcohol and mixtures thereof.
[0105] In one non-limiting embodiment, the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.
[0106] In one non-limit non-limiting embodiment, the hydrophilic moiety is that of a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, glycerol, hexylene glycol, sorbitol, neopentylglycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N- methylglucosamine, trimethylolpropane, trimethylolethane, and mixtures thereof.
[0107] In one non-limiting embodiment, the hydrophobic moiety is an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, and mixtures thereof.
[0108] In one non-limiting embodiment, the hydrophilic moiety is that of an amine selected from the group consisting of diethanolamine, serinol, 2-amino-2-ethyl-1,3-propanediol, dimethylamine, 2-methylbutylamine, 3-amino-1-propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof.
[0109] In one non-limiting embodiment, the hydrophobic moiety is that of a silicon-based compound selected from the group consisting of aminopropylmethylsiloxane–dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxane, monocarbinol terminated functional polydimethylsiloxane, [Bis(hydroxyethyl)amine] terminated polydimethylsiloxane, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.
[0110] In one non-limiting embodiment, the hydrophilic moiety is that of a silane selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.
[0111] In one non-limiting embodiment, the hydrophobic moiety is that of a hydrocarbyl alcohol that contains from about 6 to about 36 carbon atoms and that is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional.
[0112] Hydrocarbyl alcohols are classified as primary, secondary and tertiary alcohols, based on the number of carbon atoms connected to the carbon atom that bears the hydroxyl group. Each classification of alcohol has a general formula. For example, the general formula for primary alcohols isthe general formula for secondary alcohols is andthe general formula for tertiary alcohols iswherein R, R′ and R″ stand for different alkyl, alkylene, aryl, aralkyl, and arylene groups.
[0113] According to one embodiment of the present invention, (a) the hydrophobic moiety is a moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; ; unsubstituted and substituted polyols, with or without additional heteroatoms, containing from about 37 to about 60 carbon atoms; silicon-based compounds, and combinations thereof; and (b) the hydrophilic moiety is a moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, with or without additional heteroatoms, containing from about 1 to about 5 carbon atoms; ; unsubstituted and substituted polyols, with or without additional heteroatoms, containing from about 2 to about 36 carbon atoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.
[0114] According to one embodiment of the present invention, (i) the hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols is selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl- 1-octanol, 2-hexyl-1-decanol, 2-octyl-1-dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1- hexadecanol, 2-hexadecanol, 1-octadecanol, behenyl alcohol, 3,7-dimethyl-1-octanol, 2-propyl-1- pentanol, 4-methyl-1-pentanol, 1-naphthalenemethanol, benzyl alcohol, and mixtures thereof; (ii) the hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl amines is selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, and mixtures thereof; and (iii) the hydrophobic moiety selected from the group consisting of unsubstituted and substituted polyols is selected from the group consisting of 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, poly(tetramethylene ether) glycol, poly(tetramethylene carbonate) diol, poly(hexamethylene carbonate) diol and castor oil.
[0115] According to one of the embodiment of the present invention, (i) the hydrophilic moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof; (ii) the hydrophilic moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl amines is selected from the group consisting of diethanolamine, serinol, 2-amino-2-ethyl-1,3- propanediol, dimethylamine, 2-methylbutylamine, 3-aminopropanol, their hydrochloride salts, their ammonium salts, and mixtures thereof; (iii) the hydrophilic moiety selected from the group consisting of unsubstituted and substituted alcohols is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, glycerol, hexylene glycol, sorbitol, neopentylglycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, trimethylolpropane, trimethylolethane, and mixtures thereof; and (iv) the hydrophilic moiety selected from the group consisting of silanes is selected from the group consisting of 3-aminopropylsilanetriol, N-(2- aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.
[0116] Preferably, the silane is functionalized with an alcohol or an amine, and combinations thereof.
[0117] Preferably, the hydrophilic alcohol is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, methoxypolyethylene glycol, and mixtures thereof.
[0118] Hydrocarbyl amines are classified as primary, secondary, or tertiary, based on the number of carbon atoms attached to the amine nitrogen atom. Each class of amine may have a general formula. For example, the general formula for primary amine isandthe general formula for secondary amine isthe general formula for tertiary amine iswherein R1, R2and R3stand for the same or different alkyl, alkylene, aryl, aralkyl, or arylene groups.
[0119] In one non-limiting embodiment, the hydrophobic moiety is that of a hydrocarbyl amine that contains about 6 to about 36 carbon atoms and that is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional.
[0120] In one non-limiting embodiment, the silicon-based compound is a compound having the structurewherein R stands for different alkyl, alkylene, aryl, aralkyl, arylene, hetero groups functionalized with at least one or more alcohol, amine or a combination thereof and n has the value of 1 to 10.
[0121] In one non-limiting embodiment, the silicon-based compound is a siloxane, or a silane functionalized with an alcohol, an amine or a combination thereof.
[0122] In one non-limiting embodiment, the silicon-based compound is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional compound.
[0123] In one non-limiting embodiment, the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane–dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxane, monocarbinol terminated functional polydimethylsiloxane, [Bis(hydroxyethyl)amine] terminated polydimethylsiloxane, silanolterminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropyl methylsiloxane and mixtures thereof.monocarbinol terminated polydimethylsiloxane monocarbinol terminated functional polydimethylsiloxane
[0124] In one non-limiting embodiment, the silane is a hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol and mixtures thereof
[0125] In one non-limiting embodiment of the present invention, the base (D) is selected from the group consisting of inorganic bases, organic bases, and combinations thereof.
[0126] In one non-limiting embodiment, the inorganic base is selected from the group consisting of oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.
[0127] In one non-limiting embodiment, the organic base is selected from the group consisting of ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.
[0128] In one non-limiting embodiment, the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.
[0129] In one non-limiting embodiment, the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.
[0130] In one non-limiting embodiment, the transition metal is selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, yttrium zirconium, niobium, molybdenum, technetium, ruthenium, rhodium, palladium, silver, cadmium, hafnium, tantalum, tungsten, rhenium, osmium, iridium, platinum, gold, mercury, rutherfordium, dubnium, seaborgium, bohrium, hassium, meitnerium, darmstadtium, roentgenium, and mixtures thereof.
[0131] In one non-limiting embodiment, the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.
[0132] In one non-limiting embodiment, the present invention provides a slurry composition comprising (i) a reaction product of: (A) a maleated soybean oil; (B) 1-(2-hydroxyethyl)-2- pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base; and (ii) a dispersed particle, wherein the reaction product has the structure:wherein R7is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.
[0133] In one non-limiting embodiment, the present invention provides a slurry composition comprising (i) a reaction product of: (A) a maleated soybean oil; (B) 1-(2-hydroxyethyl)-2- pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base, and (ii) a dispersed particle, wherein the reaction product comprises one or more structure(s) selected from:wherein R7is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl-1-dodecyl, or mixtures thereof; and wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.
[0134] In one non-limiting embodiment, the present invention provides a slurry composition comprising (i) a reaction product of (A) a maleated soybean oil; (B) 1-(2-hydroxyethyl)-2- pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base; and (ii) a dispersed particle, wherein the reaction product is a polymer having the structure:wherein n is greater than 1; wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.
[0135] In one non-limiting embodiment, the present invention provides a slurry composition comprising (i) a reaction product having a polymer of (A) a maleated soybean oil; (B) 1-(2- hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof,wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base; and (ii) a dispersed particle, wherein the reaction product is a polymer comprising one or more structure(s) selected from:wherein 1 < n < 30; wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and, more particularly, R11is -CH2CH2CH2-, or a mixture thereof.
[0136] In one non-limiting embodiment, the dispersed particle is in powder form.
[0137] According to one of the embodiments, the dispersed particle is a coated or uncoated particle selected from the group consisting of coated and uncoated particles of a metal, an organic compound, an inorganic compound, a carbon-based compound, a composite, and mixtures thereof.
[0138] According to one of the embodiments, the carbon-based compound is carbon nanotube selected from the group consisting of a single-wall carbon nanotube, a double-wall carbon nanotube, a triple-wall carbon nanotube, a quadruple-wall carbon nanotube, a few-walled carbon nanotube, a multi-walled carbon nanotube, a carbon nanohorn, a carbon nanofiber, fullerene, short nanotubes, carbon particle nanotubes, and combinations thereof.
[0139] In one more non-limiting embodiment, the dispersed particle is selected from the group consisting of alumina, alumina oxide hydroxide, SiO2, BaSO4, TiO2, SnO2, CeO2, ZrO2, BaTiO3, Y2O3, B2O3, carbon nanotube, ZnO, aluminum-doped lithium lanthanum zirconate (Al-doped LLZO), and combinations thereof.
[0140] In one more non-limiting embodiment, the inorganic compound is selected from the group consisting of iron oxide, iron titanate, ultramarine, mica, carbon black, clay, kaolin, talc and combinations thereof.
[0141] In one more non-limiting embodiment, the metal particle is selected from the group consisting of beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), cadmium (Cd), hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), mercury (Hg), rutherfordium (Rf), dubnium (Db), seaborgium (Sg), bohrium (Bh), hassium (Hs), meitnerium (Mt), darmstadtium (Ds), roentgenium (Rg), and combinations thereof.
[0142] In one more non-limiting embodiment, the organic compound is selected from the group consisting of polyamide resin powder (nylon powder), polyethylene powder, polymethyl methacrylate powder, polystyrene powder, styrene / acrylic acid copolymer resin powder, benzoguanamine resin powder, polyethylene tetrafluoride powder, polyvinylpyrrolidone (PVP), copolymers of vinylpyrrolidone, cellulose powder and combinations thereof.
[0143] In one more non-limiting embodiment, the coated particle is selected from the group consisting of titanium oxide-coated mica, titanium oxide-coated bismuth oxychloride, titanium oxide-coated talc, colored titanium oxide-coated mica, metal-coated carbon nanotubes, metal- coated carbon graphene, and combinations thereof.
[0144] In one more non-limiting embodiment, the composite particle is colloidal polystyrene−silica.
[0145] In another non-limiting embodiment, the dispersed particle has a particle size distribution such that the d50 is in a range of from about 0.05 µm to about 50 µm.
[0146] In another non-limiting embodiment, the d50 is in a range of from about 0.05 µm to about 0.1 µm, from about 0.11 µm to about 0.2 µm, from about 0.21 µm to about 0.3µm, from about 0.31 µm to about 0.4 µm, from about 0.41 µm to about 0.5 µm, from about 0.5 µm to about 0.61, from about 0.61 µm to about 0.7 µm, from about 0.71 µm to about 0.8 µm, from about 0.81 µm to about 9 µm, from about 0.91 µm to about 1µm, from about 1.1 µm to about 5 µm, from about 6 µm to about 10 µm, from about 11 µm to about 15 µm, from about 16 µm to about 20 µm, from about 21 µm to about 25 µm, from about 26 µm to about 30 µm, from about 31 µm to about 35 µm, from about 36 µm to about 40 µm, from about 41 µm to about 45 µm and from about 46 µm to about 50 µm.
[0147] In one more non-limiting embodiment, the slurry composition further comprises a solvent selected from the group consisting of at least one aqueous solvent; alcohols; phenols; acetates; ketones; ethylene glycols; propylene glycols; amides; pyrrolidones; hydroxyesters; sulfoxides; lactones; anilines; hydrocarbons; halogenated solvents; aromatic solvents; glycol esters, and combinations thereof.
[0148] In another non-limiting embodiment, the a solvent is selected from the group consisting of water, methanol, ethanol, isopropyl alcohol, propyl alcohol, butanol, terpineol, acetone, methyl ethyl ketone, ethyl isobutyl ketone, methyl isobutyl ketone, ethylene glycol, ethylene glycol methyl ether, ethylene glycol mono-n-propyl ether, propylene glycol, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol butyl ether, propylene glycol propyl ether, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone (NMP), N-ethylpyrrolidone, dimethylsulfoxide, gamma-butyrolactone, lactic acid methyl ester, lactic acid ethyl ester, β-methoxyisobutyric acid methyl ester, α-hydroxyisobutyric acid methyl ester, aniline, N- methylaniline, hexane, chloroform, toluene, propylene glycol monomethyl ether acetate (PGMEA) and combinations thereof.
[0149] In one non-limiting embodiment, the slurry composition further comprises at least one functional ingredient selected from the group consisting of pharmaceutical agents, skin care agents, oral care agents, hair care agents, energy agents, construction agents, biocidal agents, preservative agents, nutraceutical agents, food agents, agricultural agents, coating agents, cosmetic agents, homecare agents, industrial and institutional agents, textile agents, laundry agents, cleaning agents, inorganic particles of ceramic composition, and disinfecting agents.
[0150] In one non-limiting embodiment, the slurry composition of the present invention relates to skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, metal working fluids, battery compositions, and disinfection compositions.
[0151] Another aspect of the present disclosure provides an agricultural composition comprising the slurry composition of the present disclosure.
[0152] In one non-limiting embodiment of the present disclosure, the agricultural composition comprises the slurry in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; orfrom about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%, based on the total weight of the agriculture composition.
[0153] In another non-limiting embodiment of the present disclosure, the agricultural composition can further comprise one or more agriculturally active ingredient, and one or more additional ingredient. These ingredients in totality can be present in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or from about 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.%, based on the total weight of the agriculture composition.
[0154] In one non-limiting embodiment of the present disclosure, the one or more agriculturally active ingredient used in the agricultural composition of the present disclosure includes fertilizers or pesticides. Suitable and non-limiting examples of such fertilizers or pesticides can include, but are not limited to, rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti-parasites, antimicrobials, or combinations thereof.
[0155] In another non-limiting embodiment of the present disclosure, one or more additional ingredient used can include an adjuvant or an inert ingredient. Suitable examples of adjuvants used in the agricultural composition of the present disclosure can include, but are not limited to, acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, or combinations thereof. Similarly, suitable examples of inert ingredients used in theagricultural composition of the present disclosure can include, but are not limited to, solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, or combinations thereof.
[0156] In another non-limiting embodiment of the present disclosure, the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from the group consisting of ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, or an antimicrobial composition..
[0157] In another non-limiting embodiment of the present disclosure, the agricultural composition is in the form of an aqueous or a non-aqueous composition comprising a capsule suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
[0158] In another non-limiting embodiment of the present disclosure, the present application discloses an agricultural composition comprising the slurry composition of a slurry composition comprising:(i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol, or amine functional group, and (ii) a dispersed particle.
[0159] In another non-limiting embodiment of the present disclosure, the present application discloses an agricultural composition comprising a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) alactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base, and (ii) a dispersed particle.
[0160] In another non-limiting embodiment of the present disclosure, the present application discloses an agricultural composition comprising a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base; and ii) a dispersed particle.
[0161] In another non-limiting embodiment of the present disclosure, the present application discloses a seed coating composition comprising the slurry composition of a slurry composition comprising:(i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol, or amine functional group, and (ii) a dispersed particle.
[0162] In another non-limiting embodiment of the present disclosure, the present application discloses a seed coating composition comprising a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base, and (ii) a dispersed particle.
[0163] In another non-limiting embodiment of the present disclosure, the present application discloses a seed coating composition comprising a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base; and ii) a dispersed particle.
[0164] In one non-limiting embodiment, the present application relates to a ceramic coated separator for an energy storage device, comprising: (1) a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol, or amine functional group, and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, and (2) a separator, wherein the slurry composition is in contact with at least a portion of the separator.
[0165] In another non-limiting embodiment, the invention provides a ceramic coated separator for an energy storage device, comprising: (1) a slurry composition comprising: (i) a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality, and (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group and having the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q isselected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurrycomposition, and (2) a separator, wherein the slurry composition is in contact with at least a portion of the separator.
[0166] In another non-limiting embodiment, the invention provides a ceramic coated separator for an energy storage device, comprising: (1) a slurry composition comprising: (i) a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality, and (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group and having the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, and (iii) a solvent, and (2) a separator, wherein the slurry composition is in contact with at least a portion of the separator.
[0167] In another non-limiting embodiment, the invention provides a ceramic coated separator for an energy storage device, comprising: (1) a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base, and(ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, and (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0168] In another non-limiting embodiment, the invention provides a ceramic coated separator for an energy storage device, comprising: (1) a slurry composition comprising: (i) a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group and having the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q isselected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base, and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, and (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0169] In another non-limiting embodiment, the invention provides a ceramic coated separator for an energy storage device, comprising: (1) a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) alactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base, and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, and (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0170] In another non-limiting embodiment, the invention provides a ceramic coated separator for an energy storage device, comprising: (1) a slurry composition comprising: (i) a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality, and (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group and having the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms; and, R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalizedmoiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base, and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, and (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0171] In another non-limiting embodiment, the invention provides a ceramic coated separator for an energy storage device, comprising: (1) a slurry composition comprising: (i) a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality, and (B) a lactam moiety having at least one hydroxyl functional group, wherein the lactam having at least one hydroxyl functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and the group; Q isselected from the group consisting of functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R is selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base, and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, and (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0172] In another non-limiting embodiment, the ceramic slurry composition is coated on at least one surface of the separator forming a coating thereon.
[0173] In another non-limiting embodiment, the separator comprises a polyolefin.
[0174] In another non-limiting embodiment, the polyolefin is selected from the group consisting of polyethylene, polypropylene, and combinations thereof.
[0175] In another non-limiting embodiment, the ceramic coated separator has undergone at least one treatment selected from the group consisting of: corona treatment, atmospheric plasma treatment, flame plasma treatment, chemical plasma treatment, ozone treatment, polyvinylidene difluoride (PVDF) treatment, and treatment with polydopamine.
[0176] In one more non-limiting embodiment, the coating is uniformly distributed on the separator.
[0177] In one more non-limiting embodiment, the coating has a mean thickness in a range of from about 0.5 μm to about 5 μm.
[0178] In another non-limiting embodiment, the coating has a mean thickness in a range of from about 0.5 µm to about 0.6 µm, from about 0.61 µm to about 0.7 µm, from about 0.71 µm to about 0.8 µm, from about 0.81 µm to about 0.9 µm, from about 0.91 µm to about 1 µm, or from about 1.1 µm to about 5 µm.
[0179] In one more non-limiting embodiment, the energy storage device is selected from the group consisting of a fuel cell, an electrochemical cell, a battery, and a capacitor.
[0180] In one more non-limiting embodiment, the invention relates to a battery comprising a ceramic coated separator, wherein the ceramic coated separator comprises: (1) a slurry composition comprising (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol, or amine functional group; and (ii) a dispersed particle, and (2) a separator, wherein the slurry composition is in contact with at least a portion of the separator.
[0181] In one more non-limiting embodiment, the invention relates to a battery comprising a ceramic coated separator, wherein the ceramic coated separator comprises: (1) a slurrycomposition comprising (i) a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality, and (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group and having the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selectedfrom functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (ii) a dispersed particle, and (2) a separator, wherein the slurry composition is in contact with at least a portion of the separator.
[0182] In another non-limiting embodiment, the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety.
[0183] In another non-limiting embodiment, the present application relates to a ceramic coated separator for a battery, comprising (1) a slurry composition comprising, (i) a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality, and (B) at least one lactam having at least one hydroxyl functional group, wherein the lactam having at least one hydroxyl functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from the group consisting of functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R is selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein the alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms; (ii) a dispersed particle; and (iii) a solvent, and (2) a separator, wherein the slurry composition is in contact with at least a portion of the separator.
[0184] In another non-limiting embodiment, the present application relates to a battery comprising a ceramic coated separator, wherein the ceramic coated separator comprises (1) a slurry composition comprising (i) a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality, and (B) a lactam having at least one hydroxyl functional group, wherein the lactam having at least one hydroxyl functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from the group consisting of functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may ormay not contain oxygen atom(s); and R is selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein the alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms; (ii) a dispersed particle; and (iii) a solvent, and (2) a separator, wherein the slurry composition is in contact with at least a portion of the separator.
[0185] In one more non-limiting embodiment, the invention relates to a battery, comprising the ceramic coated separator.
[0186] In one more non-limiting embodiment, the invention relates to a battery, comprising: at least one ceramic coated separator, at least one cathode, and at least one anode.
[0187] In one more non-limiting embodiment, the invention relates to a battery, comprising the ceramic coated separator for an energy storage device, comprising: (1) a ceramic slurry composition, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition; and (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0188] In one more non-limiting embodiment, the invention relates to a battery, comprising at least one ceramic coated separator comprising: (1) a slurry composition comprising (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group,, and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0189] In one more non-limiting embodiment, the invention relates to a battery, comprising at least one ceramic coated separator comprising: (1) a ceramic slurry composition comprising (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality;(B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator, at least one cathode, and at least one anode.
[0190] In one more non-limiting embodiment, the invention relates to a battery, comprising at least one ceramic coated separator comprising: (1) a ceramic slurry composition comprising (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality;(B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base, and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0191] In one more non-limiting embodiment, the invention relates to a battery, comprising at least one ceramic coated separator, comprising: (1) a ceramic slurry composition comprising (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality;(B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base, and (ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0192] In one more non-limiting embodiment, the invention relates to a battery, comprising at least one ceramic coated separator comprising: (1) a slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base, and ii) a dispersed particle, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition, and (2) a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
[0193] In one more non-limiting embodiment, the invention relates to a method of making a ceramic coated separator, comprising: a) coating the ceramic slurry composition on the separator by a method selecting from the group consisting of doctor blading, bar coating, slot-die coating, dip coating, spin coating, direct gravure, reverse coating and combinations thereof, b) drying the ceramic slurry composition coated on the separator by using an energy source selected from thegroup consisting of heat, ultraviolet (UV), light emitting diode (LED), electron beam (EB) and combinations thereof; and c) conditioning the coating at a temperature.
[0194] In one more non-limiting embodiment, the step of drying the ceramic slurry composition layer on the separator comprises heating the coated separator at a temperature in a range of from about 20 °C to about 80 °C for a time in a range of from about 5 seconds to about 10 minutes.
[0195] In one more non-limiting embodiment, the temperature in a range of from about 21 °C to about 30 °C, from about 31 °C to about 40 °C, from about 41 °C to about 50 °C, from about 51 °C to about 60 °C, from about 61 °C to about 70 °C, from about 71 °C to about 80 °C.
[0196] In one more non-limiting embodiment, the step of drying the ceramic slurry composition layer on the separator comprises heating the coated separator at a temperature in a range of from about 50 °C to about 80 °C for a time in a range of from about 1 minute to about 10 minutes.
[0197] In one more non-limiting embodiment, the ceramic slurry composition layer on the separator is further conditioned at a temperature of up to 100 °C for up to 24 hours.
[0198] In one more non-limiting embodiment, the ceramic slurry composition layer on the separator is further conditioned at a temperature in a range of from about 60 °C to about 80 °C for about 30 minutes.
[0199] Further, certain aspects of the present application are illustrated in detail by way of the following examples. The examples are given herein for illustration of the application and are not intended to be limiting thereof. EXAMPLES
[0200] Example A1: Grafting of maleic anhydride onto soybean oil
[0201] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 600 g of soybean oil and 204 g (3 mole equivalents based on soybean oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 6-8hours. Completion of the reaction was indicated by NMR, and LC indicated <0.5% of residual maleic anhydride.
[0202] Example A2: Grafting of maleic anhydride onto palm oil
[0203] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of palm oil and 23 g (2 mole equivalents based on palm oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ˚C and then held at 210 ˚C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%.
[0204] Example A3: Grafting of maleic anhydride onto canola oil
[0205] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of canola oil and 22.2 g (2 mole equivalents based on canola oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ˚C and then held at 210 ˚C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%.
[0206] Example A4: Grafting of maleic anhydride onto sunflower oil
[0207] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of sunflower oil and 22.4 g (2 mole equivalents based on sunflower oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ˚C and then held at 210 ˚C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%.
[0208] Example A5: Grafting of maleic anhydride onto castor oil
[0209] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of castor oil and 21 g (2 mole equivalents based on castor oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for15 minutes, heated slowly from room temperature to 210 ˚ C and then held at 210 ˚ C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%.
[0210] Example A6: Grafting of maleic anhydride onto chickpea oil
[0211] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter and mechanical stirrer was charged with 100 g of chickpea oil and 38 g (3.4 mole equivalents relative to chickpea oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 10-14 hours. The amber, viscous product was characterized by NMR, and LC indicated <0.5% of residual maleic anhydride. Yield of maleated chickpea oil was >96%.
[0212] Example A7: Grafting of maleic anhydride onto clary sage oil
[0213] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter and mechanical stirrer was charged with 100 g of clary sage oil and 51.5 g (3 mole equivalents relative to clary sage oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 8 hours. The amber, viscous product was characterized by NMR, and LC indicated <0.5% of residual maleic anhydride. Yield of maleated clary sage oil was >96%.
[0214] Example B1: Sodium salt of maleated soybean oil from aqueous sodium hydroxide
[0215] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of maleated soybean oil (MSBO) from Example A1 was heated to 90 °C, and a mixture of 20.20 g (3 mole equivalents based on soybean oil) of 50% aqueous sodium hydroxide and 70 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.
[0216] Example B2: Sodium salt of maleated soybean oil (MSBO) from sodium carbonate
[0217] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 was heated to 90 °C, and 27.86g (3 mole equivalents based on soybean oil) of sodium carbonate dissolved in 85 g of water was added over 3 hours, controlling the foam formation. The reaction was held at 90 °C for 3 hours. The product contained 56 weight % solids and was characterized by IR. Yield was >96%.
[0218] Example B3: Sodium salt of MSBO from aqueous sodium hydroxide
[0219] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of MSBO from Example A1 was heated to 90 °C, and a mixture of 9.04 g (2 mole equivalents based on soybean oil) of 50% aqueous sodium hydroxide and 80 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.
[0220] Example C1: Grafting of 1-(2-hydroxyethyl)-2-pyrrolidone (HEP) onto maleated soybean oil (MSBO)
[0221] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 and either 0.5, 1, 1.5, 2, 2.5 or 3 mole equivalents, relative to MSBO, of 1-(2-hydroxyethyl)-2-pyrrolidone (HEP) were combined, heated to 120 °C and held at 120 °C for 6 hours. The amber, viscous product was characterized by NMR and IR, and GC indicated <5% of residual HEP. Yield was >96%.
[0222] Example C2: Grafting of 1-(2-aminoethyl)-2-pyrrolidone onto maleated soybean oil (MSBO)
[0223] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 and 10.0 g (1 mole equivalent, relative to MSBO) of 1-(2-aminoethyl)-2-pyrrolidone are combined, heated to 80 °C and held at 80 °C for 6 hours.
[0224] Example D1: Sodium salt of maleated soybean oil (MSBO) reacted with HEP
[0225] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of the product from Example C1 was heated to 85 °C. Water and 50% aqueous sodium hydroxide were added over 60 minutes to create a final solution that was 50weight % solids, and the mixture was held at 85 °C for 4 hours. The amount of sodium hydroxide added was sufficient to convert each carboxylic acid group generated by hydrolysis of anhydride or reaction of anhydride with HEP into the corresponding sodium carboxylate salt. The amber liquid product was characterized by NMR and IR. Yield of MSBO-HEP adduct sodium salt was >98%.
[0226] Example D2: Lithium salt of maleated soybean oil (MSBO) reacted with HEP
[0227] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 152.1 g of MSBO made according to Example A1 and 41.8g (2.5 mole equivalents relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The amber, viscous product was cooled to 80 °C, and 9.31 g (3 mole equivalents relative to MSBO) of lithium hydroxide dissolved in 204 g of water was added over 1 hour to create a final solution that was 50 weight % solids. The mixture was heated to 85 °C and held at 85 °C for 2 hours. The amber product was characterized by NMR and IR. Yield was >96%.
[0228] Example D3: Sodium salt of maleated soybean oil (MSBO) reacted with 1-(2- aminoethyl)-2-pyrrolidone
[0229] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of the product from Example C2 is heated to 85 °C. Water and 50% aqueous sodium hydroxide are added over 60 minutes to create a final solution that is 50 weight % solids, and the mixture is held at 85 °C for 4 hours. The amount of sodium hydroxide added is sufficient to convert each carboxylic acid group generated by hydrolysis of anhydride or reaction of anhydride with 1-(2-aminoethyl)-2-pyrrolidone into the corresponding sodium carboxylate salt.
[0230] Example E1: Maleated soybean oil (MSBO) reacted with HEP and 2-octyl-1- dodecanol and crosslinked with glycerol
[0231] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 211 g of MSBO made according to Example A1 and 9.69 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was adjusted to 85 °C, and 72.8 g (1.3 mole equivalents) of 2-octyl-1-dodecanol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (17.3 g, 1.0 mole equivalent) wasadded, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.
[0232] Example E2: Maleated soybean oil (MSBO) reacted with HEP and 2-ethyl-1- hexanol and crosslinked with glycerol
[0233] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of MSBO made according to Example A1 and 9.10 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 29.8 g (1.3 mole equivalents) of 2-ethyl-1-hexanol was added, and the mixture was held at 85 °C for 6 hours. The mixture was heated to 90 °C, 16.2 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.
[0234] Example E3: Maleated soybean oil (MSBO) reacted with HEP and benzyl alcohol and crosslinked with glycerol
[0235] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 167 g of MSBO made according to Example A1 and 11.0 g (0.6 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, 20.0 g (1.3 mole equivalents) of benzyl alcohol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (13.1 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.
[0236] Example E4: Maleated soybean oil (MSBO) reacted with HEP and 1- naphthalenemethanol and crosslinked with glycerol
[0237] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 167 g of MSBO made according to Example A1 and 11.0 g (0.6 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 29.2 g (1.3 mole equivalents) of 1-naphthalenemethanol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (13.1 g, 1.0 mole equivalent) wasadded, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.
[0238] Example E5: Maleated soybean oil (MSBO) reacted with HEP and lauryl alcohol and crosslinked with glycerol
[0239] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 161 g of MSBO made according to Example A1 and 7.34 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 34.4 g (1.3 mole equivalents) of lauryl alcohol was added, and the mixture was held at 85 °C for 6 hours. The mixture was heated to 90 °C, 13.1 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.
[0240] Example E6: Maleated soybean oil (MSBO) reacted with HEP and behenyl alcohol and crosslinked with glycerol
[0241] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 151 g of MSBO made according to Example A1 and 6.87 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 59.4 g (1.3 mole equivalents) of behenyl alcohol was added, and the mixture was held at 85 °C for 6 hours. The mixture was heated to 90 °C, 12.24 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.
[0242] Example E7: Maleated soybean oil (MSBO) reacted with 1-(2-aminoethyl)-2- pyrrolidone and 2-octyl-1-dodecanol and crosslinked with glycerol
[0243] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 211 g of MSBO made according to Example 1 and 9.69 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was adjusted to 85 °C, and 72.8 g (1.3 mole equivalents) of 2-octyl-1-dodecanol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (17.3 g, 1.0 mole equivalent) wasadded, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.
[0244] Example F1: Seed coating using reaction product of Example D1 and polyvinyl alcohol
[0245] A seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 4 parts polyvinyl alcohol, 1 part of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse.
[0246] Example F2: Seed coating using reaction product of Example D1 and PEG 400
[0247] A seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 3 parts PEG 400, 2 parts of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse.
[0248] Example F3: Seed coating using reaction product of Example D1 and styrene acrylic copolymer
[0249] A seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 2.5 parts styrene acrylic copolymer, 2.5 parts of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse.
[0250] Example F4: Seed coating using reaction product of Example D1 and vinyl pyrrolidone / vinyl acetate copolymer
[0251] A seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 3 parts vinylpyrrolidone / vinyl acetate copolymer, 2 parts of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse.
[0252] Example G: Ceramic Slurry Preparation and Separator Characterization
[0253] Ashland Soteras™ CCS-V and deionized water are mixed for several minutes at 900 rpm. Ceramic particles are added, and the slurry is mixed at 1500 rpm for 1 hour. A 10 wt% aqueous solution of Soteras™ CCS-B is added by dropper, and the slurry is mixed for 5 minutes. A 10 wt% aqueous solution of the dispersant of Example D1 is added to the slurry by dropper, and the slurry is mixed a further 30 minutes. Ambergum™ 1221 (Ashland, Inc.) is used as a comparative dispersant. The final concentration of the combination of Soteras™ CCS-V and Soteras™ CCS-B (ratioed according to product instructions) in the slurry is about 1.6 to about 1.7 weight %. The final concentration of the ceramic particles is about 33 weight %. The final concentration of the dispersant (Example D1 or Ambergum™ 1221) is varied between 0.00 weight % and 0.20 weight %. In particular, ceramic slurries are tested wherein the dispersant is present at 0.12 weight % and 0.16 weight %.
[0254] The viscosity of the ceramic slurry is measured using a Brookfield viscometer, LV type, at 25 °C. The viscosity of the slurry is reduced by adding the dispersant.
[0255] Using a drawdown bar, the slurry is spread on a sheet of polyolefin separator film to form an even, uniform coating of ceramic layer. The coated film is cured in an oven at 60 °C for 1 minute. The cured film is removed from the oven and cooled to room temperature.
[0256] Gurley porosity (air permeability) of the coated polyolefin films (and of uncoated, pristine polyolefin film, as a reference) is measured using a Gurley densometer from TMI Machine, Inc. (New Castle, DE). The Gurley number expresses the time required for 100 mL of air to pass through a specific area of separator. The time differences between the coated films (usually longer) and the blank, uncoated polyolefin film is determined. Gurley increment results are presented as percentages. An ideal Gurley increment measurement is no change (0%) compared to the Gurley porosity measurement of a blank polyolefin substrate.
[0257] To determine the thermal shrinkage of the ceramic coated separator films, pre-cut squares of the separator films are heated in an air-convention oven at 150 °C for 1 hour. After 1 hour, the separator squares are examined and measured for thermal shrinkage. For shrinkage, the lower the number, the better the results.
[0258] While the compositions and methods of the disclosed and / or claimed inventive concept(s) have been described in terms of particular aspects, it will be apparent to those of ordinary skill in the art that variations may be applied to the compositions and / or methods and in the steps or in the sequence of steps of the method described herein without departing from theconcept, spirit and scope of the disclosed and / or claimed inventive concept(s). All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the disclosed and / or claimed inventive concept(s).
Claims
We claim:
1. A slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol, or amine functional group, and (ii) a dispersed particle.
2. The slurry composition according to claim 1, wherein the maleated natural oil is selected from the group consisting of maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof.
3. The slurry composition according to claim 1, wherein the maleated natural oil is a maleated soybean oil.
4. The slurry composition according to claim 1, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure: wherein:Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thgroup and thegroup;Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
5. The slurry composition according to claim 4, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); and each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
6. The slurry composition according to claim 5, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.
7. The slurry composition according to claim 6, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure:
8. The slurry composition according to claim 1 comprising a reaction product of (A) a maleated soybean oil, and (B) 1-(2-hydroxyethyl)-2-pyrrolidone; wherein reaction product is a maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)-2-pyrrolidone moieties.
9. The slurry composition according to claim 8, comprising one or more structure(s) selected from:
10. The slurry composition according to claim 6, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-aminoethyl)-2-pyrrolidone, having the structure:
11. The slurry composition according to claim 1 comprising a reaction product of (A) a maleated soybean oil; and (B) 1-(2-aminoethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)-2-pyrrolidone moieties.
12. The slurry composition according to claim 11, comprising one or more structure(s) selected from:wherein, R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms.
13. The slurry composition according to claim 1, wherein the dispersed particle is in powder form.
14. The slurry composition according to claim 1, wherein the dispersed particle has a particle size distribution, d50, in a range of from about 0.05 µm to about 50 µm.
15. The slurry composition according to claim 1, wherein the dispersed particle is selected from the group consisting of alumina, alumina oxide hydroxide, SiO2, BaSO4, TiO2, SnO2, CeO2, ZrO2, BaTiO3, Y2O3, B2O3, carbon nanotube, ZnO, aluminum-doped lithium lanthanum zirconate (Al-doped LLZO), and combinations thereof.
16. The slurry composition according to claim 1, wherein the slurry composition further comprises a solvent selected from the group consisting of at least one aqueous solvent; alcohols; phenols; acetates; ketones; ethylene glycols; propylene glycols; amides; pyrrolidones; hydroxyesters; sulfoxides; lactones; anilines; hydrocarbons; halogenated solvents; aromatic solvents; glycol esters; and combinations thereof.
17. The slurry composition according to claim 16, wherein the solvent is selected from the group consisting of water, methanol, ethanol, isopropyl alcohol, propyl alcohol, butanol, terpineol, acetone, methyl ethyl ketone, ethyl isobutyl ketone, methyl isobutyl ketone, ethylene glycol, ethylene glycol methyl ether, ethylene glycol mono-n-propyl ether, propylene glycol,propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol butyl ether, propylene glycol propyl ether, dimethylformamide, dimethylacetoamide, N-methyl-2-pyrrolidone (NMP), N-ethylpyrrolidone, dimethylsulfoxide, gamma-butyrolactone, lactic acid methyl ester, lactic acid ethyl ester, β-methoxyisobutyric acid methyl ester, α-hydroxyisobutyric acid methyl ester, aniline, N-methylaniline, hexane, chloroform, toluene, propylene glycol monomethyl ether acetate (PGMEA), methyl acetoacetate and combinations thereof.
18. The slurry composition according to claim 1, wherein the composition further comprises at least one functional ingredient selected from the group consisting of pharmaceutical agents, skin care agents, oral care agents, hair care agents, energy agents, construction agents, biocidal agents, preservative agents, nutraceutical agents, food agents, agricultural agents, coating agents, cosmetic agents, homecare agents, industrial and institutional agents, textile agents, laundry agents, cleaning agents, inorganic particles of ceramic composition, and disinfecting agents.
19. The slurry composition according to claim 1, wherein the composition is selected from the group consisting of skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, metal working fluids, battery compositions, and disinfection compositions.
20. An agricultural composition comprising the slurry composition of claim 1.
21. The agricultural composition according to claim 20, wherein the slurry composition is present in the range of from about 0.1 wt.% to about 95.0 wt.% of the agriculture composition.
22. The agricultural composition according to claim 20, wherein the agricultural composition further comprises from about 0.01 wt.% to about 99.9 wt.% of one or more agriculturally active ingredient and one or more additional ingredient.
23. The agricultural composition according to claim 22, wherein the agriculturally active ingredient is a fertilizer or a pesticide selected from the group consisting of rodenticides,miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti- parasites, and antimicrobials.
24. The agricultural composition according to claim 22, wherein the additional ingredient is an adjuvant or an inert ingredient.
25. The agricultural composition according to claim 24, wherein the adjuvant is selected from the group consisting of acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, and mixtures thereof.
26. The agricultural composition according to claim 24, wherein the inert ingredient is selected from the group consisting of solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, and mixtures thereof.
27. The agricultural composition according to claim 20, wherein the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from the group consisting of ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, or an antimicrobial composition.
28. The agricultural composition according to claim 20, wherein the agricultural composition is in the form of an aqueous or a non-aqueous composition comprising a capsule suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueousemulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
29. A ceramic coated separator for an energy storage device, comprising: - the slurry composition of claim 1, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition; and - a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
30. The ceramic coated separator according to claim 29, wherein the ceramic particle is selected from the group consisting of alumina, alumina oxide hydroxide, SiO2, BaSO4, TiO2, SnO2, CeO2, ZrO2, BaTiO3, Y2O3, B2O3, ZnO, aluminum-doped lithium lanthanum zirconate (Al- doped LLZO), and combinations thereof.
31. The ceramic coated separator according to claim 29, wherein the ceramic slurry composition is coated on at least one surface of the separator forming a coating thereon.
32. The ceramic coated separator according to claim 29, wherein the separator comprises a polyolefin.
33. The ceramic coated separator according to claim 32, wherein the polyolefin is selected from the group consisting of polyethylene, polypropylene, and combinations thereof.
34. The ceramic coated separator according to claim 29, wherein the separator has undergone at least one treatment selected from the group consisting of: corona treatment, atmospheric plasma treatment, flame plasma treatment, chemical plasma treatment, ozone treatment, polyvinylidene difluoride (PVDF) treatment, and treatment with polydopamine.
35. The ceramic coated separator according to claim 31, wherein the coating is uniformly distributed on the surface of the separator.
36. The ceramic coated separator according to claim 31, wherein the coating has a mean thickness in a range of from about 1 to about 5μm.
37. An energy storage device, comprising the ceramic coated separator of claim 29, wherein the energy storage device is selected from the group consisting of a fuel cell, an electrochemical cell, a battery, and a capacitor.
38. A battery, comprising the ceramic coated separator according to claim 29.
39. A battery, comprising: - at least one ceramic coated separator of claim 29, - at least one cathode, and - at least one anode.
40. A method of making a ceramic coated separator, comprising: a) creating a ceramic slurry coating on a separator by coating the ceramic slurry composition of claim 29 on the separator by a method selected from the group consisting of doctor blading, bar coating, slot-die coating, dip coating, spin coating, direct gravure, reverse coating and combinations thereof; b) creating a ceramic coating on the separator by drying the ceramic slurry coating of step (a) on the separator by using an energy source selected from the group consisting of heat, ultraviolet (UV), light emitting diode (LED), electron beam (EB) and combinations thereof; and c) conditioning the ceramic coating of step (b) at a temperature.
41. The method of making a ceramic coated separator according to claim 40, wherein the step of (b) drying the ceramic slurry coating on the separator comprises heating the coated separator at a temperature in a range of from about 20 °C to about 80 °C for a time in a range of from about 5 seconds to about 10 minutes.
42. The method of making a ceramic coated separator according to claim 40, wherein the step of (b) drying the ceramic slurry coating on the separator comprises heating the coated separator at a temperature in a range of from about 50 °C to about 80 °C for a time in a range of from about 1 minute to about 10 minutes.
43. The method of making a ceramic coated separator according to claim 40, wherein the step of (c) conditioning the ceramic coating on the separator is conducted at a temperature of up to 100 °C for up to 24 hours.
44. The method of making a ceramic coated separator according to claim 40, wherein the step of (c) conditioning the ceramic coating on the separator is conducted at a temperature in a range of from about 60 °C to about 80 °C for about 30 minutes.
45. A slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base, and (ii) a dispersed particle.
46. The slurry composition according to claim 45, wherein the maleated natural oil is selected from the group consisting of maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof.
47. The slurry composition according to claim 45, where in the maleated natural oil is a maleated soybean oil.
48. The slurry composition according to claim 36, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup;Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
49. The slurry composition according to claim 48, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andX is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
50. The slurry composition according to claim 49, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.
51. The slurry composition according to claim 50, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure:
52. The slurry composition according to claim 45, wherein the base (C) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.
53. The slurry composition according to claim 52, wherein the inorganic base is selected from the group consisting of oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.
54. The slurry composition according to claim 52, wherein the organic base is selected from the group consisting of ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.
55. The slurry composition according to claim 53, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.
56. The slurry composition according to claim 53, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.
57. The slurry composition according to claim 53, wherein the transition metal is selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, yttrium zirconium, niobium, molybdenum, technetium, ruthenium, rhodium, palladium, silver, cadmium, hafnium, tantalum, tungsten, rhenium, osmium, iridium, platinum, gold, mercury, rutherfordium, dubnium, seaborgium, bohrium, hassium, meitnerium, darmstadtium, roentgenium, and mixtures thereof.
58. The slurry composition according to claim 52, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.
59. The slurry composition according to claim 45, wherein the slurry composition comprising a reaction product of (A) a maleated soybean oil; (B) 1-(2-hydroxyethyl)-2- pyrrolidone; and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium, wherein the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)-2-pyrrolidone moieties.
60. The slurry composition according to claim 59, comprising one or more structure(s) selected from:61 The slurry composition according to claim 45, wherein the composition further comprises at least one functional ingredient selected from the group consisting of pharmaceutical agents, skin care agents, oral care agents, hair care agents, energy agents, construction agents, biocidal agents, preservative agents, nutraceutical agents, food agents, agricultural agents, coating agents, cosmetic agents, homecare agents, industrial and institutional agents, textile agents, laundry agents, cleaning agents, inorganic particles of ceramic composition, and disinfecting agents.
62. The slurry composition according to claim 45, wherein the composition is selected from the group consisting of skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, metal working fluids, battery compositions, and disinfection compositions.
63. An agricultural composition comprising the slurry composition of claim 45.
64. The agricultural composition according to claim 63, wherein the slurry composition is present in the range of from about 0.1 wt.% to about 95.0 wt.% of the agriculture composition.
65. The agricultural composition according to claim 63, wherein the agricultural composition further comprises from about 0.01 wt.% to about 99.9 wt.% of one or more agriculturally active ingredient and one or more additional ingredient.
66. The agricultural composition according to claim 65, wherein the agriculturally active ingredient is a fertilizer or a pesticide selected from the group consisting of rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti- parasites, and antimicrobials.
67. The agricultural composition according to claim 65, wherein the additional ingredient is an adjuvant or an inert ingredient.
68. The agricultural composition according to claim 67, wherein the adjuvant is selected from the group consisting of acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, and mixtures thereof.
69. The agricultural composition according to claim 67, wherein the inert ingredient is selected from the group consisting of solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, and mixtures thereof.
70. The agricultural composition according to claim 63, wherein the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from the group consisting of ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, or an antimicrobial composition.
71. The agricultural composition according to claim 63, wherein the agricultural composition is in the form of an aqueous or a non-aqueous composition comprising a capsule suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
72. A ceramic coated separator for an energy storage device, comprising: - the slurry composition of claim 45, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition; and - a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
73. The ceramic coated separator according to claim 72, wherein the ceramic particle is selected from the group consisting of alumina, alumina oxide hydroxide, SiO2, BaSO4, TiO2, SnO2, CeO2, ZrO2, BaTiO3, Y2O3, B2O3, ZnO, aluminum-doped lithium lanthanum zirconate (Al- doped LLZO), and combinations thereof.
74. The ceramic coated separator according to claim 72, wherein the ceramic slurry composition is coated on at least one surface of the separator forming a coating thereon.
75. The ceramic coated separator according to claim 72, wherein the separator comprises a polyolefin.
76. The ceramic coated separator according to claim 75, wherein the polyolefin is selected from the group consisting of polyethylene, polypropylene, and combinations thereof.
77. The ceramic coated separator according to claim 74, wherein the separator has undergone at least one treatment selected from the group consisting of: corona treatment, atmospheric plasma treatment, flame plasma treatment, chemical plasma treatment, ozone treatment, polyvinylidene difluoride (PVDF) treatment, and treatment with polydopamine.
78. The ceramic coated separator according to claim 74, wherein the coating is uniformly distributed on the surface of the separator.
79. The ceramic coated separator according to claim 74, wherein the coating has a mean thickness in a range of from about 1 to about 5μm.
80. An energy storage device, comprising the ceramic coated separator of claim 72, wherein the energy storage device is selected from the group consisting of a fuel cell, an electrochemical cell, a battery, and a capacitor.
81. A battery, comprising the ceramic coated separator according to claim 72.
82. A battery, comprising: - at least one ceramic coated separator of claim 72, - at least one cathode, and - at least one anode.
83. A method of making a ceramic coated separator, comprising: a) creating a ceramic slurry coating on a separator by coating the ceramic slurry composition of claim 72 on the separator by a method selected from the group consisting of doctor blading, bar coating, slot-die coating, dip coating, spin coating, direct gravure, reverse coating and combinations thereof; b) creating a ceramic coating on the separator by drying the ceramic slurry coating of step (a) on the separator by using an energy source selected from the group consisting of heat, ultraviolet (UV), light emitting diode (LED), electron beam (EB) and combinations thereof; and c) conditioning the ceramic coating of step (b) at a temperature.
84. The method of making a ceramic coated separator according to claim 83, wherein the step of (b) drying the ceramic slurry coating on the separator comprises heating the coated separator at a temperature in a range of from about 20 °C to about 80 °C for a time in a range of from about 5 seconds to about 10 minutes.
85. The method of making a ceramic coated separator according to claim 83, wherein the step of (b) drying the ceramic slurry coating on the separator comprises heating the coated separator at a temperature in a range of from about 50 °C to about 80 °C for a time in a range of from about 1 minute to about 10 minutes.
86. The method of making a ceramic coated separator according to claim 83, wherein the step of (c) conditioning the ceramic coating on the separator is conducted at a temperature of up to 100 °C for up to 24 hours.
87. The method of making a ceramic coated separator according to claim 83, wherein the step of (c) conditioning the ceramic coating on the separator is conducted at a temperature in a range of from about 60 °C to about 80 °C for about 30 minutes.
88. A slurry composition comprising: (i) a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base; and ii) a dispersed particle.
89. The slurry composition according to claim 88, wherein the maleated natural oil is selected from the group consisting of maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof.
90. The slurry composition according to claim 88, wherein the maleated natural oil is a maleated soybean oil.
91. The slurry composition according to claim 88, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure: wherein:Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
92. The slurry composition according to claim 91, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and,X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
93. The slurry composition according to claim 92, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.
94. The slurry composition according to claim 93, wherein the lactam (B) having at least one hydroxyl, thiol or amine is 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure:
95. The slurry composition according to claim88, wherein the hydrophobic moiety (C) is a moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; unsubstituted and substituted polyols, with or without additional heteroatoms, containing from about 37 to about 60 carbon atoms; silicon-based compounds, and combinations thereof.
96. The slurry composition according to claim88, wherein the hydrophilic moiety (C) is a moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, with or without additional heteroatoms,containing from about 1 to about 5 carbon atoms; unsubstituted and substituted polyols, with or without additional heteroatoms, containing from about 2 to about 36 carbon atoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.
97. The slurry composition according to claim 96, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.
98. The slurry composition according to claim 95, wherein the hydrophobic moiety is that of (i) an alcohol selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl-1- octanol, 2-hexyl-1-decanol, 2-octyl-1-dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1- hexadecanol, 2-hexadecanol, 1-octadecanol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4- methyl-1-pentanol, behenyl alcohol, 1-naphthalenemethanol, benzyl alcohol and mixtures thereof.
99. The slurry composition according to claim 95, wherein the hydrophobic moiety is that of a polyol selected from the group consisting of 1,6-hexanediol, 1,7-heptanediol, 1,8- octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, poly(tetramethylene ether) glycol, poly(tetramethylene carbonate) diol, poly(hexamethylene carbonate) diol, castor oil and mixtures thereof.
100. The slurry composition according to claim 96, wherein the hydrophilic moiety is an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.
101. The slurry composition according to claim 96, wherein the hydrophilic moiety is that of a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, glycerol, hexylene glycol, sorbitol, neopentylglycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, trimethylolpropane, trimethylolethane, and mixtures thereof.
102. The slurry composition according to claim 95, wherein the hydrophobic moiety is that of an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine,methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, and mixtures thereof.
103. The slurry composition according to claim 95, wherein the hydrophilic moiety is that of an amine selected from the group consisting of diethanolamine, serinol, 2-amino-2-ethyl- 1,3-propanediol, dimethylamine, 2-methylbutylamine, 3-amino-1-propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof.
104. The slurry composition according to claim 95, wherein the hydrophobic moiety is silicon-based compound selected from the group consisting of aminopropylmethylsiloxane– dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1- dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]- dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxane, monocarbinol terminated functional polydimethylsiloxane, [Bis(hydroxyethyl)amine] terminated polydimethylsiloxane, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.
105. The slurry composition according to claim 96, wherein the hydrophilic compound is silane compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2- aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.
106. The slurry composition according to claim 88, wherein the base (D) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.
107. The slurry composition according to claim 106, wherein the inorganic base is selected from the group consisting of oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.
108. The slurry composition according to claim 106, wherein the organic base is selected from the group consisting of ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.
109. The slurry composition according to claim 107, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.
110. The slurry composition according to claim 107, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.
111. The slurry composition according to claim 107, wherein the transition metal is selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, yttrium zirconium, niobium, molybdenum, technetium, ruthenium, rhodium, palladium, silver, cadmium, hafnium, tantalum, tungsten, rhenium, osmium, iridium, platinum, gold, mercury, rutherfordium, dubnium, seaborgium, bohrium, hassium, meitnerium, darmstadtium, roentgenium, and mixtures thereof.
112. The slurry composition according to claim 106, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.
113. The slurry composition according to claim 88, wherein the slurry composition comprises a reaction product of (A) a maleated soybean oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base.
114. The slurry composition according to claim 113, wherein the reaction product has the structure:wherein R7is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.
115. The slurry composition according to claim 114, wherein the reaction product comprises one or more structure(s) selected from:wherein R7is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl-1-dodecyl, or mixtures thereof; and wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.
116. The slurry composition according to claim 113, wherein the reaction product is a polymer having the structure:wherein n is greater than 1; wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.
117. The reaction product according to claim 116, wherein the polymer comprises one or more structure(s) selected from:; wherein 1 < n < 30; wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms.
118. The reaction product according to claim 117, wherein R11is -CH2CH2CH2-,or a mixture thereof.
119. The slurry composition according to claim 88, wherein the composition further comprises at least one functional ingredient selected from the group consisting of pharmaceutical agents, skin care agents, oral care agents, hair care agents, energy agents, construction agents,biocidal agents, preservative agents, nutraceutical agents, food agents, agricultural agents, coating agents, cosmetic agents, homecare agents, industrial and institutional agents, textile agents, laundry agents, cleaning agents, inorganic particles of ceramic composition, and disinfecting agents.
120. The slurry composition according to claim 88, wherein the composition is selected from the group consisting of skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, metal working fluids, battery compositions, and disinfection compositions.
121. An agricultural composition comprising the slurry composition of claim 88.
122. The agricultural composition according to claim 121, wherein the slurry composition is present in the range of from about 0.1 wt.% to about 95.0 wt.% of the agriculture composition.
123. The agricultural composition according to claim 121, wherein the agricultural composition further comprises from about 0.01 wt.% to about 99.9 wt.% of one or more agriculturally active ingredient and one or more additional ingredient.
124. The agricultural composition according to claim 123, wherein the agriculturally active ingredient is a fertilizer or a pesticide selected from the group consisting of rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti- parasites, and antimicrobials.
125. The agricultural composition according to claim 123, wherein the additional ingredient is an adjuvant or an inert ingredient.
126. The agricultural composition according to claim 125, wherein the adjuvant is selected from the group consisting of acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oilconcentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, and mixtures thereof.
127. The agricultural composition according to claim 125, wherein the inert ingredient is selected from the group consisting of solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, and mixtures thereof.
128. The agricultural composition according to claim 121, wherein the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from the group consisting of ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, or an antimicrobial composition.
129. The agricultural composition according to claim 121, wherein the agricultural composition is in the form of an aqueous or a non-aqueous composition comprising a capsule suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
130. A ceramic coated separator for an energy storage device, comprising: - the slurry composition of claim 88, wherein the dispersed particle is a ceramic particle, and wherein the slurry composition is a ceramic slurry composition; and- a separator, wherein the ceramic slurry composition is in contact with at least a portion of the separator.
131. The ceramic coated separator according to claim 130, wherein the ceramic particle is selected from the group consisting of alumina, alumina oxide hydroxide, SiO2, BaSO4, TiO2, SnO2, CeO2, ZrO2, BaTiO3, Y2O3, B2O3, ZnO, aluminum-doped lithium lanthanum zirconate (Al- doped LLZO), and combinations thereof.
132. The ceramic coated separator according to claim 130, wherein the ceramic slurry composition is coated on at least one surface of the separator forming a coating thereon.
133. The ceramic coated separator according to claim 130, wherein the separator comprises a polyolefin separator.
134. The ceramic coated separator according to claim 133, wherein the polyolefin is selected from the group consisting of polyethylene, polypropylene, and combinations thereof.
135. The ceramic coated separator according to claim 130, wherein the separator has undergone at least one treatment selected from the group consisting of: corona treatment, atmospheric plasma treatment, flame plasma treatment, chemical plasma treatment, ozone treatment, polyvinylidene difluoride (PVDF) treatment, and treatment with polydopamine.
136. The ceramic coated separator according to claim 132, wherein the coating is uniformly distributed on the surface of the separator.
137. The ceramic coated separator according to claim 132, wherein the coating has a mean thickness in a range of from about 1 to about 5μm.
138. An energy storage device, comprising the ceramic coated separator of claim 130, wherein the energy storage device is selected from the group consisting of a fuel cell, an electrochemical cell, a battery, and a capacitor.
139. A battery, comprising the ceramic coated separator according to claim 130.
140. A battery, comprising: - at least one ceramic coated separator of claim 130, - at least one cathode, and- at least one anode.
141. A method of making a ceramic coated separator, comprising: a) creating a ceramic slurry coating on a separator by coating the ceramic slurry composition of claim 130 on the separator by a method selected from the group consisting of doctor blading, bar coating, slot-die coating, dip coating, spin coating, direct gravure, reverse coating and combinations thereof; b) creating a ceramic coating on the separator by drying the ceramic slurry coating of step (a) on the separator by using an energy source selected from the group consisting of heat, ultraviolet (UV), light emitting diode (LED), electron beam (EB) and combinations thereof; and c) conditioning the ceramic coating of step (b) at a temperature.
142. The method of making a ceramic coated separator according to claim 141, wherein the step of (b) drying the ceramic slurry coating on the separator comprises heating the coated separator at a temperature in a range of from about 20 °C to about 80 °C for a time in a range of from about 5 seconds to about 10 minutes.
143. The method of making a ceramic coated separator according to claim 141, wherein the step of (b) drying the ceramic slurry coating on the separator comprises heating the coated separator at a temperature in a range of from about 50 °C to about 80 °C for a time in a range of from about 1 minute to about 10 minutes.
144. The method of making a ceramic coated separator according to claim 141, wherein the step of (c) conditioning the ceramic coating on the separator is conducted at a temperature of up to 100 °C for up to 24 hours.
145. The method of making a ceramic coated separator according to claim 141, wherein the step of (c) conditioning the ceramic coating on the separator is conducted at a temperature in a range of from about 60 °C to about 80 °C for about 30 minutes.
Citation Information
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Renewable modified natural compounds
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