WO2025059059A1 - Compositions de suspension comprenant des sels d'huile naturelle modifiés, leurs procédés de préparation et leurs applications - Google Patents

Compositions de suspension comprenant des sels d'huile naturelle modifiés, leurs procédés de préparation et leurs applications Download PDF

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Publication number
WO2025059059A1
WO2025059059A1 PCT/US2024/046020 US2024046020W WO2025059059A1 WO 2025059059 A1 WO2025059059 A1 WO 2025059059A1 US 2024046020 W US2024046020 W US 2024046020W WO 2025059059 A1 WO2025059059 A1 WO 2025059059A1
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WIPO (PCT)
Prior art keywords
compositions
composition
agents
maleated
oils
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English (en)
Inventor
Osama M. Musa
Henry Keith Chenault
Mousumi Ghosh
Shufu Peng
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ISP Investments LLC
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ISP Investments LLC
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D191/00—Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/65—Additives macromolecular
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/66—Additives characterised by particle size
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J191/00—Adhesives based on oils, fats or waxes; Adhesives based on derivatives thereof

Definitions

  • 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”) relates generally to slurry compositions comprising modified natural oils including their salts, and a process(es) for preparation thereof.
  • the present disclosure further relates to various compositions derived from the present slurry composition.
  • Natural oils are abundant, inexpensive, and are derived from sustainable sources, and are one of the most promising raw materials for the synthesis of renewable compounds such as polymers, plastics, and plasticizers. These natural oils are inexpensive, highly abundant, come from reliable and sustainable sources, and have a high potential for modification. Natural oils are generally blends of different triglycerides, the esterification product of fatty acids and glycerol, and contain varying degrees of unsaturation (i.e., double bonds). Oils can be characterized by a hydroxyl value and fatty acid compositions. A difficulty with utilizing natural oils is that they are blends of triglycerides containing varying degrees of unsaturated double bonds which are relatively unreactive.
  • these unsaturated double bonds are generally chemically modified to make them reactive.
  • these unsaturated bonds can be reacted with maleates to provide natural oils chemically modified/functionalized with epoxide functional groups and succinic anhydride functional groups.
  • These chemical modifications further allow the addition of many hydroxyl containing species to be introduced into the natural oils.
  • the modified natural oils can be non-dispersible in water or alcohol.
  • oils can be incorporated into a wide variety of compositions and applications, for example personal care such as hair care, sun care, skin care, oral care; adhesives; coatings; paints; electronics; households; industrial and institutional (HI&I) compositions; inks; membranes; metal working fluids; oilfield chemicals; plastics and plasticizers; textiles; industrial products; biocides; nutraceuticals; and agrochemical compositions.
  • personal care such as hair care, sun care, skin care, oral care; adhesives; coatings; paints; electronics; households; industrial and institutional (HI&I) compositions; inks; membranes; metal working fluids; oilfield chemicals; plastics and plasticizers; textiles; industrial products; biocides; nutraceuticals; and agrochemical compositions.
  • US Patent 9809538B2 describes a modified natural compound synthesized from an epoxidized natural fatty acid, maleated natural fatty acid, epoxidized natural oil, or maleated natural oil and a lactam compound having at least one hydroxyl group, wherein the modified natural compound has utility in, e.g., adhesive or beverage compositions.
  • US Patent No. 2754306A describes a reaction of soybean oil, maleic anhydride and isooctyl alcohol to provide an improved plasticizer for nitrocellulose compositions.
  • PCT Publication No. 2019113068A1 describes a technology related to metalworking fluids comprising maleated soybean oil derivatives.
  • US Patent No.2754306A describes a reaction of soybean oil, maleic anhydride and isooctyl alcohol to provide an improved plasticizer for nitrocellulose compositions.
  • PCT Publication No. 2005071050A1 describes a succinated triglyceride oil derived from maleating triglyceride oil from a plant or land animal for use as an emulsifying agent for metalworking fluids.
  • US Patent Application Publication No. 20180070584A1 describes an adjuvant composition that includes a maleated natural oil derivative obtained from the reaction of a maleated natural oil and a derivative compound such as poly oxy alkylene glycol, mono-alkyl polyoxyalkylene glycol, polyetheramine, alkyleneamine, alkanolamine, thiol -terminated polyoxyalkylene glycol, ammonia, Group IA metal hydroxide, Group IIA metal hydroxide or mixture thereof.
  • US Patent No. 10889693 B2 teaches a composition including a modified oil alkyl ester and/or modified oil aryl ester having the transesterification reaction product of an oil (soybean oil) and a surfactant having hydroxy group.
  • US Patent No. 5733970 A teaches an aqueous dispersed, epoxy crosslinked maleated oil (maleated glyceride oil) microgel polymers for protective coatings.
  • US Application Publication No. 20130210630 Al teaches a self-emulsifying oil having a modified vegetable oil which is modified with a moiety more polar than the vegetable oil and the polar moiety is attached by a covalent bond to the vegetable oil and an active ingredient.
  • the present disclosure provides a slurry composition
  • a slurry composition comprising: (i) a reaction product of (a) a maleated natural oil comprising a natural oil with maleated functionality; and (b) a base; (ii) at least one dispersed particle; and (iii) at least one solvent.
  • the reaction product comprises a maleated functionality fully or partially reacted with the base.
  • the base is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.
  • 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 mixture thereof.
  • the maleated natural oil is a maleated soybean oil.
  • the reaction product comprises one or more structures selected from the group consisting of the following structures:
  • the dispersed particle is selected from the group consisting of alumina, alumina oxide hydroxide, SiCh, BaSCh, TiCh, SnC>2, CeCh, ZrCh, BaTiCh, Y2O3, B2O3, carbon nano tube, ZnO, Al -doped Lithium Lanthanum Zirconate Oxide (LLZO), and combinations thereof.
  • the dispersed particle is in powder form.
  • the dispersed particle has a particle size distribution (d50) in the range of from about 0.05 ⁇ m to about 50.0 ⁇ m.
  • the solvent is 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.
  • the slurry composition is selected from the group consisting of agriculture compositions, biocidal compositions, ceramic slurry compositions, cleaning compositions, coating compositions, personal care composition , construction compositions, disinfecting compositions, energy compositions, food compositions, homecare compositions, industrial and institutional compositions, laundry compositions, nutraceutical compositions, oral care compositions, preservative compositions, textile compositions, carbon nano-tube compositions, battery compositions, and ceramic coated separators for batteries.
  • the slurry composition is a personal care composition, a coating composition, a food composition, an agricultural composition, or a carbon nanotube composition.
  • Another aspect of the present disclosure provides an energy storage device comprising the ceramic coated separator according to the present disclosure, wherein the energy storage device is selected from the group consisting of fuel cells, electrochemical cells, batteries, and capacitors.
  • Still another aspect of the present disclosure provides a battery, comprising: (i) at least one ceramic coated separator according to the present disclosure; (ii) at least one cathode; and (iii) at least one anode.
  • Another aspect of the present disclosure provides a coating composition comprising the slurry of the present disclosure.
  • the slurry is present in the range of from about 0.1 wt.% to about 95.0 wt.% of the coating composition.
  • Still another aspect of the present disclosure provides a personal care composition comprising the slurry of the present disclosure. In one non-limiting embodiment of the present disclosure, the slurry is present in an amount of from about 0.1 wt.% to about 95.0 wt.% of the personal care composition.
  • Another aspect of the present disclosure provides an agriculture composition comprising the slurry of the present disclosure.
  • the slurry is present in an amount of from about 0.1 wt.% to about 95.0 wt.% of the agriculture composition.
  • Another aspect of the present disclosure provides a carbon nanotube composition comprising the slurry of the present disclosure.
  • the slurry is present in an amount of from about 0.1 wt.% to about 95.0 wt.% of the carbon nanotube composition.
  • inventive concept(s) Before explaining at least one embodiment of the inventive concept(s) in detail by way of exemplary drawings, experimentation, results, and laboratory procedures, it is to be understood that the inventive concept(s) is not limited in its application to the details of construction and the arrangement of the components set forth in the following description or illustrated in the drawings, experimentation and/or results.
  • inventive concept(s) is/are capable of other embodiments or of being practiced or carried out in various ways.
  • the language used herein is intended to be given the broadest possible scope and meaning; and the embodiments are meant to be exemplary - not exhaustive.
  • phraseology and terminology employed herein is for the purpose of description and should not be regarded as limiting.
  • compositions and/or methods disclosed and claimed herein can be made and executed without undue experimentation in light of the present disclosure. While the compositions and methods of this invention have been described in terms of preferred embodiments, it will be apparent to those of 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 the concept, spirit and scope of the invention. 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 inventive concept(s) as defined by the appended claims.
  • 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.
  • A, B, C, or combinations thereof refers to all permutations and combinations of the listed items preceding the term.
  • “A, B, C, or combinations thereof’ is intended to include at least one of: A, B, C, AB, AC, BC, or ABC, and if order is important in a particular context, also BA, CA, CB, CBA, BCA, ACB, BAC, or CAB.
  • expressly included are combinations that contain repeats of one or more item or term, such as BB, AAA, MB, BBC, AAABCCCC, CBBAAA, CABABB, and so forth.
  • the skilled artisan will understand that typically there is no limit on the number of items or terms in any combination, unless otherwise apparent from the context.
  • 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.
  • 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, tetra polymers, quaternary polymers, and homologues.
  • copolymer refers to a polymer consisting essentially of two or more different types of monomers polymerized to obtain said copolymer.
  • reaction product refers to a substance produced from a chemical reaction of one or more reactant substances.
  • 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.
  • maleated natural oil or “natural oil with maleated functionality”, can be used interchangeable without limiting the scope of the present disclosure, and refer to natural oil comprising at least one maleated functionality. Accordingly, the term “maleation” or “maleated” as used hereafter should be understood to mean “functionalization” in so far as the use of functionalizing reagents other than maleic anhydride are contemplated for use in the present disclosure.
  • molecularity refers to a part or a functional group(s) of a molecule.
  • 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).
  • maleated functionality pictured in I, II, 111 and IV might also be called by one of ordinary skill in the art succinic anhydride, succinic acid, succinate salt or succinate half ester functionality.
  • base 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 14.0).
  • 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.
  • organic base includes ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.
  • inorganic base 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.
  • alkali metal base includes oxides, hydroxides, carbonates, or bicarbonates of sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr).
  • alkali-earth metal base includes oxides, hydroxides, carbonates, or bicarbonates of beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra).
  • transition metal base includes oxides, hydroxides, carbonates, or 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), hass
  • dispersed particles refers to a substance added to the present slurry composition to improve the separation of particles and to prevent settling or clumping.
  • Suitable and non-limiting examples of such dispersed particles according to the present disclosure may include particles of alumina, alumina oxide hydroxide, SiO2, BaSO4 , TiO2, SnO2, CeO2, ZrO2, BaTi32, Y2O3, B2O3, carbon nanotube, ZnO, aluminum-doped lithium lanthanum zirconate (Al -doped LLZO), and combinations thereof.
  • battery includes a single electrochemical cell, or uni cell, and/or one or more electrochemical cells connected in series and/or in parallel as known by those of skill in the art. Further suitable and non-limiting examples of battery according to the present disclosure can include, but are not limited to, rechargeable batteries, secondary batteries, and/or electrochemical cells.
  • the battery according to the present disclosure may include a positive electrode (cathode) and a negative electrode (anode), wherein both electrodes include a carbon nanotube (CNT) material capable of absorbing and desorbing lithium in an electrochemical system, and wherein lithium metal powder is dispersed in the CNT of the anode or a cathode, a separator separating the cathode and the anode, and an electrolyte in communication with the cathode and the anode.
  • CNT carbon nanotube
  • carbon nanotube means a hollow carbon structure having a diameter from about 4 nm to about 100 nm.
  • the “carbon nanotubes” (CNTs) according to the present disclosure can be any suitable type of carbon nanotube. Suitable and nonlimiting examples of carbon nanotubes include, single-wall carbon nanotubes, double-wall carbon nanotubes, few-wall carbon nanotubes, multi-wall carbon nanotubes, bundle-type carbon nanotubes, or a combination thereof. Carbon nanotubes having a high electrical conductivity may be particularly suitable.
  • the present disclosure provides a slurry composition
  • a slurry composition comprising (i) a reaction product of (a) a maleated natural oil comprising a natural oil with maleated functionality and (b) a base; (ii) at least one dispersed particle; and (iii) at least one solvent.
  • the reaction product according to the present disclosure includes a natural oil with maleated functionality wherein the maleated functionality is either fully or partially reacted with the base.
  • the maleated natural oil or the natural oil with maleated functionality as used in the present slurry composition includes a natural oil comprising at least one maleated functionality.
  • suitable examples of such natural oils with maleated functionality can include, but are not limited to, 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.
  • the maleated natural oil is a maleated soybean oil.
  • the base can be selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.
  • the base can be inorganic base.
  • Suitable examples of inorganic base can include, but are not limited to, 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.
  • the alkali metals can be selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.
  • the alkaline earth metal can be selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.
  • the transition metal can be 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.
  • the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates, and bicarbonates of sodium, calcium, and combinations thereof.
  • the base suitable for the purpose of the present disclosure can be an organic base. Suitable examples of such organic base can include, but are not limited to, ammonia, primary amines, secondary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.
  • the reaction product comprises one or more structures selected from the group consisting of the following structures:
  • the maleated natural oil or natural oil with maleated functionality in the present slurry composition can be prepared by the maleation of natural oils.
  • one or more of an ⁇ , ⁇ -unsaturated carboxylic acid or anhydride thereof, for example, maleic anhydride reacts with unsaturated fatty acyl chains present in natural oils.
  • the maleation of natural oils 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 preparation of maleated natural oils is well known to persons skilled in the art. Accordingly, the maleated natural oils as used for the purpose of the present disclosure can be prepared by methods known in the related arts. In one non-limiting embodiment of the present disclosure, maleic anhydride and at least one natural oil can be reacted together at elevated temperatures.
  • the maleation can be carried out at a temperature varying in the range of from about 150 °C to about 300 °C. In another non-limiting embodiment of the present disclosure, the maleation can be carried out at a temperature of from about 170 °C to about 230 °C, or from about 200 °C to about 220 °C.
  • the maleation can be carried out for a time period varying from about 0.5 hours to about 14 hours.
  • the reaction time can vary from about 1 hour to about 5 hours, or from about 2 hours to about 6 hours, or from about 6 hours to 10 hours.
  • the mole ratio of maleic anhydride to natural oil can be equal to 1. In a still another non-limiting embodiment of the present disclosure, the mole ratio can vary from about 1 to about 2, or from about 1 to about 2.8, or from about 1 to about 3.2 moles of maleic anhydride for each mole of natural oil.
  • the maleated natural oil according to the present disclosure is reacted with a suitable base to form a reaction product.
  • the maleated natural oil and a suitable base are reacted together under pre-determined condition of temperature and for a pre-determined period of time to obtain the present reaction product.
  • the maleated natural oil is reacted with a suitable base at a temperature ranging from about 20 °C to about 120 °C.
  • the maleated natural oil is reacted with a suitable base at a temperature ranging from about 40 °C to about 100 °C.
  • the maleated natural oil is reacted with a suitable base at a temperature ranging from about 40 °C to about 49 °C, from about 50 °C to about 59 °C, from about 60 °C to about 69 °C, from about 70 °C to about 79 °C, from about 80 °C to about 89 °C, from about 90 °C to about 100 °C.
  • the maleated natural oil is reacted with a suitable base at a suitable temperature for a time ranging from about 30 minutes to about 6 hours.
  • the maleated natural oil is reacted with a suitable base for about 1 hour, for about 2 hours, for about 3 hours, for about 4 hours, for about 5 hours or for about 6 hours.
  • the slurry composition according to the present disclosure can further comprises at least one dispersed particle.
  • the dispersed particle is selected from the group consisting of alumina, alumina oxide hydroxide, SiO 2 , BaSO 4 , TiO 2 , SnO 2 , CeO 2 , ZrO 2 , BaTiO 3 , Y 2 O 3 , B 2 O 3 , carbon nano tube, ZnO, Al-doped Lithium Lanthanum Zirconate Oxide (LLZO), and combinations thereof.
  • the dispersed particles are in powder form.
  • the dispersed particles according to the present disclosure has a particle size distribution (d50) in the range of from about 0.05 ⁇ m to about 50.0 ⁇ m.
  • the particle size distribution can vary in the range of from about 0.05 ⁇ m to about 0.1 ⁇ m, or from about 0.11 ⁇ m to about 0.2 ⁇ m, or from about 0.21 ⁇ m to about 0.3 ⁇ m, or from about 0.31 ⁇ m to about 0.4 ⁇ m, or from about 0.41 ⁇ m to about 0.5 ⁇ m, or from about 0.5 ⁇ m to about 0.61, or from about 0.61 ⁇ m to about 0.7 ⁇ m, or from about 0.71 ⁇ m to about 0.8 ⁇ m, or from about 0.81 ⁇ m to about 9 ⁇ m, or from about 0.91 ⁇ m to about 1 ⁇ m, or from about 1.1 ⁇ m to about 5 ⁇ m, or from about 6 ⁇ m to about 10 ⁇ m, or from about 11 ⁇ m to about 15
  • the solvent in the slurry composition of the present disclosure can be 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.
  • the solvent can be 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, dimethyl acetaamide, N-methyl-2-pyrrolidone (NMP), N-ethyl pyrrolidone, dimethyl sulfoxide, gamma-butyrolactone, lactic acid methyl ester, lactic acid ethyl ester, P-me
  • the slurry composition according to the present disclosure further comprises at least one functional ingredient selected from the group consisting of 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 compositions, and disinfecting agents.
  • the slurry composition according to the present disclosure can be used in various applications.
  • the slurry composition can be selected from the group consisting of agricultural compositions, biocidal compositions, ceramic slurry compositions, cleaning compositions, coating compositions, personal care composition, construction compositions, disinfecting compositions, energy compositions, food compositions, homecare compositions, industrial and institutional compositions, laundry compositions, nutraceutical composition, oral care compositions, preservative compositions, textile compositions, carbon-nanotube compositions, battery compositions, and ceramic coated separators for batteries.
  • the slurry composition can be a personal care composition, a coating composition, a food composition, an agricultural composition, or a carbon nanotube composition
  • the slurry composition can be a personal care composition.
  • suitable examples of such personal care compositions can include, but are not limited, cosmetic compositions, skin care compositions, sun care compositions, hair care compositions, nail care compositions, anti-perspirants, or deodorants, and cosmetic compositions.
  • the slurry composition can be a coating composition suitable for various applications.
  • suitable examples of such coating compositions can include, but are not limited to, architectural coatings, metal coatings, marine coatings, paints, decorative paints, interior paints, exterior paints, non-woven coatings, ceramic coatings, anti-corrosion coatings, flame retardant coatings, glass coatings, protective coatings, powder coatings, wood coatings, industrial coatings, anti-fouling coatings, thermal insulation coatings, water-based coatings, and solvent based coatings.
  • the slurry composition can be an agriculture composition.
  • the slurry composition can be used in ceramic coated separators for an energy storage device.
  • the slurry composition can be a carbon nanotube composition.
  • a ceramic coated separator for an energy storage device, comprising: (i) the slurry composition of the present disclosure, wherein the slurry composition is a ceramic slurry composition; and (ii) a separator, wherein the ceramic slurry composition provides a coating that is in contact with at least a portion of the separator.
  • the ceramic slurry composition is coated on at least one surface of the separator forming a coating thereon.
  • the ceramic slurry composition is coated on at least one surface of the separator, forming a coating thereon.
  • the separator is comprised of polyolefins.
  • the polyolefin can be selected from the group consisting of polyethylene, polypropylene, and combinations thereof.
  • the separator is a pretreated separator wherein the separator is pre-treated by at least one treatment selected from the group consisting of corona treatment, atmospheric plasma treatment, flame plasma treatment, chemical plasma treatment, ozone treatment, polyvinylidene fluoride (PVDF) treatment, and treatment with polydopamine.
  • at least one treatment selected from the group consisting of corona treatment, atmospheric plasma treatment, flame plasma treatment, chemical plasma treatment, ozone treatment, polyvinylidene fluoride (PVDF) treatment, and treatment with polydopamine.
  • the coating is uniformly distributed on the separator.
  • the coating has a mean thickness in a range of from about 0.5 ⁇ m to about 5.0 ⁇ m.
  • the coating has a mean thickness in a range of from about 0.5 ⁇ m to about 0.61, from about 0.61 ⁇ m to about 0.7 ⁇ m, from about 0.71 ⁇ m to about 0.8 ⁇ m, from about 0.81 ⁇ m to about 9.0 ⁇ m, from about 0.91 ⁇ m to about 1.0 ⁇ m, or from about 1.1 ⁇ m to about 5.0 pm.
  • Yet another aspect of the present disclosure provides an energy storage device comprising the ceramic coated separator of the present disclosure.
  • the energy storage device according to the present disclosure can be selected from the group consisting of fuel cells, electrochemical cells, batteries, and capacitors.
  • the energy storage device is selected from the group consisting of a fuel cell, electrochemical cell, battery, and a capacitor.
  • Another aspect of the present disclosure provides a battery comprising: (i) at least one ceramic coated separator of the present disclosure; (ii) at least one cathode; and (iii) at least one anode.
  • Still another aspect of the present disclosure provides a method of making a ceramic coated separator, comprising: a) coating the slurry composition of the present disclosure on at least a portion of a separator by a method selecting from the group of methods consisting of doctor blading, bar coating, slot-die coating, dip coating, spin coating, direct gravure, reverse coating, and combinations thereof; b) drying the slurry composition coated on the separator obtained from the method step (a) by using an energy source selected from the group consisting of heat, ultraviolet (UV), light emitting diode (LED), electronic beam (EEB), and combinations thereof; and; c) conditioning the dried coating of method step (b) at a pre-determined temperature.
  • a method selecting from the group of methods consisting of doctor blading, bar coating, slot-die coating, dip coating, spin coating, direct gravure, reverse coating, and combinations thereof b) drying the slurry composition coated on the separator obtained from the method step (a) by using an energy source selected from the group consisting of heat, ultraviolet
  • the method step of drying (b) 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.
  • the method step of drying can be carried out at a temperature in a range of from about 50 °C to about 80 °C for a time in the range of from about 1 minute to about 10 minutes.
  • the slurry layer on the separator is further conditioned at a temperature of up to 100 °C for up to 24 hours.
  • the conditioning can be carried out at a temperature in the range of from about 60 °C to about 80 °C for about 30 minutes.
  • the method step of drying the slurry layer on the separator comprises heating the separator coated with the present slurry composition at a temperature in the range of from about 20 °C to about 80 °C and for a time period in the range of from about 5 seconds to about 10 minutes.
  • the temperature can vary in the range of from about 21 °C to about 30 °C, or from about 31 °C to about 40 °C, or from about 41 °C to about 50 °C, or from about 51 °C to about 60 °C, or from about 61 °C to about 70 °C, or from about 71 °C to about 80 °C.
  • Still another aspect of the present disclosure provides a coating composition comprising the slurry composition of the present disclosure.
  • the slurry composition can be present in an amount of 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.
  • the coating composition can further comprises at least one additive 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
  • Suitable examples of additives used in the present coating composition can include, but are not limited to, film forming polymers, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, plasticizers, or combinations thereof.
  • the coating composition of the present disclosure can be an aqueous or a nonaqueous composition used for various coating purpose including, but not limiting to, lacquer coating, primer coating, inkjet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non-metallic coatings.
  • the coating composition is coated on a substrate selected from the group consisting of porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, fabrics, ceramics, yarns, and woven, knitted, natural, synthetic or regenerated substrates.
  • a substrate selected from the group consisting of porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, fabrics, ceramics, yarns, and woven, knitted, natural, synthetic or regenerated substrates.
  • the personal care composition can comprises the slurry composition 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.
  • the personal care composition can further comprises at least one personal care functional active ingredient 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 wwt.%; or from about 50 w
  • Suitable examples of such personal care functional active ingredient can include, but are not limited, color agents, hair care agents, skin care agents, and sun care agents, or combinations of two or more thereof.
  • the personal care functional active ingredient used in the personal care composition of the present disclosure can include, but are not limited to, fragrances, preservatives, solvents, propellants, exfoliants, surfactants, skin cell renewal agents, anti-acne medications, antiperspirant compounds, sunscreens, decomposition products of oils or fats, water- insoluble ingredients, oxidizing agents, conditioning agents, humectants, pH adjusting buffers, waxes, mineral oils, emulsifiers, fatty substances, gelling agents, thickeners, moisturizers, emollients, hydrophilic or lipophilic active agent, antioxidants, sequestering agents, acidifying or basifying agents, fillers, dyestuffs, plant extracts, proteins, peptides, neutralizing agents, solvents, anti-dandr
  • the personal care compositions can include, but are not limited to, cosmetic compositions, skin care compositions, sun care compositions, hair care compositions, nail care compositions, anti-perspirants, or deodorants, and cosmetic compositions. Further suitable and non-limiting examples of such composition can include, but are not limited to
  • body wash compositions skin lotion compositions, sunscreen compositions, anti-wrinkle compositions, moisturizer compositions, facial cleaning compositions, lipstick compositions, lipgloss compositions, mascara compositions, foundation compositions, anti-perspirant compositions, shaving compositions, hair conditioner compositions, anti-perspirant compositions, deodorant compositions, hair rinse compositions, hair shampoo compositions, hair styling compositions, make-up remover compositions, or oral care compositions.
  • the personal care composition is an aqueous or non-aqueous formulation in the form of a spray, lotion, mousse, fluid, serum, solution, suspension, perm, emulsion, gel, mist, vesicles, dispersion, paste, cream, solid stick, shampoo, balm, wipe, milk, foam, jelly, or liquid.
  • Another aspect of the present disclosure provides an agricultural composition comprising the slurry composition 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
  • 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.
  • the one or more agriculturally active ingredient used in the agricultural composition of the present disclosure includes fertilizers or pesticides.
  • 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, antiprotozoal s, anti-parasites, antimicrobials, or combinations thereof.
  • one or more additional ingredient used can include an adjuvant or an inert ingredient.
  • 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.
  • suitable examples of inert ingredients used in the agricultural 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.
  • 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.
  • ovicide rodenticide
  • insecticide miticide
  • algicide algicide
  • molluscicide acaricide
  • avicide fungicide and herbicide compositions
  • a germicide composition an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antipro
  • the agricultural composition is in the form of an aqueous or a non-aqueous composition
  • 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.
  • the present disclosure provides a carbon nanotube composition comprising the slurry composition of the present disclosure.
  • the carbon nanotube composition according to the present disclosure further comprises (i) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (ii) at least one solvent.
  • the carbon nanotube can be selected from the group consisting of single wall nanotubes, double-wall carbon nanotubes, triplewall carbon nanotubes, quadruple-wall carbon nanotubes, few-wall carbon nanotubes, multiwalled carbon nanotubes, carbon nanohoms, carbon nanofibers, short nanotubes, carbon particle nanotubes, and combinations thereof.
  • the solvent present in the carbon nanotube composition can be selected from the group consisting of at least one aqueous solvent; alcohols; ketones; ethyleneglycols; propyleneglycols; amides; pyrrolidones; hydroxyesters; sulfoxides; lactones; anilines; hydrocarbons; halogenated solvents; aromatic solvents; glycol esters; and combinations thereof.
  • the solvent can be 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, 0-
  • the reactions and compositions according to the disclosure may be analyzed by known techniques. Especially preferred are the techniques of 13 C nuclear magnetic resonance (NMR) spectroscopy, gas chromatography (GC), infrared (IR) spectroscopy, liquid chromatography (LC) and gel permeation chromatography (GPC) in order to determine identity, residual monomer concentrations, molecular weight, and molecular weight distribution.
  • NMR nuclear magnetic resonance
  • GC gas chromatography
  • IR infrared
  • LC liquid chromatography
  • GPC gel permeation chromatography
  • 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 (SBO) and 204 g (3 mole equivalents based on SBO) of maleic anhydride.
  • SBO soybean oil
  • 204 g 3 mole equivalents based on SBO
  • 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 6-8 hours. Completion of the reaction was indicated by NMR, and LC indicated ⁇ 0.5% of residual maleic anhydride.
  • Example A3 Grafting of Maleic Anhydride onto Canola Oil
  • 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 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%.
  • a l -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 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%.
  • Example Bl Sodium Salt of Maleated Soybean Oil from Aqueous Sodium Hydroxide
  • Example B2 Sodium Salt of Maleated Palm Oil from Aqueous Sodium Hydroxide
  • Example B4 Sodium Salt of Maleated Sunflower Oil from Aqueous Sodium Hydroxide
  • Example Cl Sodium Salt of Maleated Soybean Oil from Sodium Carbonate
  • Example D2 Sodium Calcium Salt of Maleated Palm Oil from Calcium Carbonate and Sodium Carbonate (7:3 ratio)
  • Example D3 Sodium Calcium Salt of Maleated Canola Oil from Calcium Carbonate and Sodium Carbonate (7:3 ratio)
  • Example D4 _Sodium Calcium Salt of Maleated Sunflower Oil from Calcium Carbonate and Sodium Carbonate (7:3 ratio)
  • Example D5 Sodium Calcium Salt of Maleated Castor Oil from Calcium Carbonate and Sodium Carbonate (7:3 ratio)
  • Example El Calcium Salt of Maleated Soybean Oil from Calcium Carbonate
  • Example Fl Sodium Salt of Maleated Soybean Oil from Aqueous Sodium Hydroxide
  • Example F2 Sodium and Diethanolamine Salt of Maleated Soybean Oil
  • Example G Toothpaste Compositions having a Slurry of Silica and Titanium Dioxide
  • Toothpaste compositions were made, using methods and equipment commonly used by those skilled in the art. Tables 1 and 2 detail the compositions made, including a list of ingredients used and their weight proportions.
  • a tooth gel phase (comprising the toothpaste rheology modifier gums in the toothpaste liquid phase) was prepared first. Following this, the remaining ingredients were mixed under a vacuum of at least 28 inches Hg in a double planetary mixer. Toothpaste compositions comprising the sodium salt of maleated soybean oil of Example Bl or GantrezTM S-97 p(MVE/MA) copolymer was made by dissolving these ingredients into the gel phase before processing under vacuum in the double planetary mixer.
  • the essential oils/flavor mixture used in this example consisted of 8.34 wt.% 4-isopropyl m-cresol (IPMP), 25.00 wt.% eugenol, 25.00 wt.% eucalyptol, and 41.66 wt.% peppermint oil.
  • HAP hydroxyapatite
  • Sintered, calcium deficient, hydroxyapatite (HAP) discs were coated with a mucin protein pellicle layer by treating the discs overnight at 37 °C in a 1% mucin/electrolyte solution (“artificial saliva”) before treatment.
  • Toothpaste supernatant solutions were prepared by making a 1 : 1 slurry of toothpaste compositions of example G in de-ionized water and centrifuging at 4,500 x g for 45 minutes. The supernatant layer was poured off the top of the centrifuge tube and used as is.
  • [00135] Water-based Carbon Nanotube dispersions of this example was made using different weight proportions of sodium salt of maleated soybean oil of example Bl and carboxymethyl cellulose CMC (AmbergumTM 1221, Ashland) as dispersant.
  • dispersant of example Bl (0.25 g) was fully dissolved in 49.5 g of distilled water at a temperature of 5-35 °C and an overhead mixer speed of 200-1000 rpm for about 1-8 hours, until no particle was observable by the eye.
  • Carbon nanotubes (JiangSu Cnano, 0.25 g) were added to the aqueous mixture, and the mixture in a closed container was shaken by hand for 30 seconds and placed the container in a sonicating bath for 15 minutes. The container was transferred to an ultrasonic mixer, utilizing a cool water bath, and sonicated for about 2-4 hours. The container was removed from the ultrasonic mixer and cooled.
  • Example II Water-based CNT dispersions, prepared according to Example I, using different proportions of the dispersant of Example Bl and carboxymethyl cellulose CMC (AmbergumTM 1221, Ashland), were analyzed for particle size distribution and resistivity. As can be seen from the results in Table 5, the dispersant of Example Bl improves the particle size distribution and resistivity of the CNT dispersion, relative to carboxymethyl cellulose (CMC).
  • CMC carboxymethyl cellulose
  • Example K Coatings Comprising a Slurry of Titanium dioxide, Calcium carbonate, Talc, and Clay
  • Paints comprising the sodium salt of maleated soybean oil (Example B 1) or Indofd 731 as dispersant were made, using methods and equipment commonly used by those skilled in the art. Table 6 details the compositions made. Table 7 reports performance data.
  • Example L Ceramic Slurry Preparation and Separator Characterization
  • Ashland SoterasTM CCS-A and deionized water were mixed for several minutes at 900 rpm. Ceramic particles were added, and the slurry was mixed at 1500 rpm for 1 hour. A 10 wt% aqueous solution of SoterasTM CCS-B was added by dropper, and the slurry was mixed for 5 minutes. A 10 wt% aqueous solution of dispersant of Example F2 was added to the slurry by dropper, and the slurry was mixed a further 30 minutes. AmbergumTM 1221 (Ashland, Inc., Wilmington, DE) was used as a comparative dispersant.
  • the slurry viscosity was measured by Brookfield viscometer, LV type, at 25 °C. The viscosity of the slurry was reduced by adding the dispersant.
  • the slurry was spread on a sheet of polyolefin separator film to form an even, uniform coating of ceramic layer.
  • the coated film was cured in an oven at 60 °C for 1 minute. The cured film was removed from the oven and cooled to room temperature.
  • Gurley equipment was used to determine the air permeability of coated polyolefin films and the pristine, uncoated film.
  • Gurley number expresses the time required for 100 mb of air to pass through a specific area of separator. The time differences between the coated films (usually longer) and a blank, uncoated polyolefin film were determined.
  • Gurley porosity measurements of the ceramic coated separators were measured using a Gurley densometer from TMI Machine, Inc. (New Castle, DE). Gurley increment results are presented as a percentage, an ideal Gurley increment measurement is no change (0%) compared to Gurley porosity measurement of a blank polyolefin substrate.
  • Ceramic-coated separators were heated at 150 °C for 1 hour in an air-convention oven. After 1 hour, the separator squares were examined and measured for thermal shrinkage. For shrinkage, the lower the number, the better the results.
  • Boehmite APYRAL® AOH 60 (Nabaltec AG, Germany):
  • 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 the concept, 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).

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Abstract

L'invention concerne une composition de suspension comprenant (i) un produit de réaction de (a) une huile naturelle maléatée ; et (b) une base ; (ii) au moins une particule dispersée ; et (iii) au moins un solvant. L'invention concerne également un séparateur revêtu de céramique ; un dispositif de stockage d'énergie comprenant le présent séparateur revêtu de céramique, tel que des piles à combustible, des cellules électrochimiques, des batteries et des condensateurs ; des compositions de revêtement ; une composition de soins personnels ; et des compositions agricoles comprenant la composition de suspension de la présente invention.
PCT/US2024/046020 2023-09-11 2024-09-10 Compositions de suspension comprenant des sels d'huile naturelle modifiés, leurs procédés de préparation et leurs applications Pending WO2025059059A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090065736A1 (en) * 2007-07-03 2009-03-12 Georgia-Pacific Chemicals Llc Chemical modification of maleated fatty acids
US20130289284A1 (en) * 2010-07-26 2013-10-31 Osama M. Musa Renewable modified natural compounds
WO2014145972A2 (fr) * 2013-03-15 2014-09-18 Ethox Chemicals, Llc Dispersants à base biologique
US20180070584A1 (en) * 2015-03-25 2018-03-15 Huntsman Petrochemical Llc Maleated Natural Oil Derivatives as Agrochemical Inert Ingredients

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090065736A1 (en) * 2007-07-03 2009-03-12 Georgia-Pacific Chemicals Llc Chemical modification of maleated fatty acids
US20130289284A1 (en) * 2010-07-26 2013-10-31 Osama M. Musa Renewable modified natural compounds
WO2014145972A2 (fr) * 2013-03-15 2014-09-18 Ethox Chemicals, Llc Dispersants à base biologique
US20180070584A1 (en) * 2015-03-25 2018-03-15 Huntsman Petrochemical Llc Maleated Natural Oil Derivatives as Agrochemical Inert Ingredients

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