Dispersant comprising hydrophobic and hydrophilic modified maleated natural oil salts for carbon nanotubes and carbon nanotube composition

Abstract

The present invention provides a dispersant for a carbon nanotube or a carbon nanotube composition comprising a reaction product of (a) a maleated natural oil with maleated functionality; (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof and (c) a base. Also, the present invention provides a dispersant for a carbon nanotube or a carbon nanotube composition comprising a reaction product of (a) a maleated natural oil with maleated functionality; (b) a base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof. The dispersant for carbon nanotubes or carbon nanotube compositions comprising reaction products of this invention are used in lithium-ion or sodium ion batteries.

Description

DISPERSANT COMPRISING HYDROPHOBIC AND HYDROPHILIC MODIFIED MALEATED NATURAL OIL SALTS FOR CARBON NANOTUBES AND CARBON NANOTUBE COMPOSITION FIELD OF THE INVENTION

[0001] The present application provides a dispersant for a carbon nanotube or a carbon nanotube composition comprising a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) 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 (C) a base. Also, the present invention provides a dispersant for a carbon nanotube or a carbon nanotube composition comprising a reaction product of (a) a maleated natural oil with maleated functionality; (b) a base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof. 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 / nutritionals, 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, themaleated 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] 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.

[0005] A discussion of reaction scheme for the maleation reaction in the vegetable oil is provided in the article “Maleated soybean oil and its multifunctional properties,” by Gripp, Anna A., Steinberg, David C., published in Cosmetics Exhibition & Conference Conference Proceedings, Barcelona, Mar.22-24, 1994.

[0006] A discussion of reaction scheme for the maleation reaction in the vegetable oil is provided in the article “Microwave Assisted Syntheses of Vegetable Oil Based Monomer,” by Rafael T. Alarcon et al., published in Journal of Polymers and the Environment 28:1265–1278, 2020.

[0007] A discussion of generalized reaction between maleic anhydride and unsaturated vegetable oils is provided in the Handbook of Maleic Anhydride Based Materials: Syntheses, Properties and Applications by Osama M. Musa in chapter 3 page 166, published in Springer International Publishing Switzerland 2016.

[0008] US Patent 2754306A describes a reaction of soybean oil, maleic anhydride and iso-octyl alcohol to provide an improved plasticizer for nitrocellulose compositions.

[0009] PCT Application 2019113068A1 describe a technology related to metalworking fluids comprising maleated soybean oil derivatives.

[0010] A discussion of maleic anhydride polymerization and modified plant oils with polyols is provided in the article “Polymerization of Maleic Anhydride–Modified Plant Oils with Polyols,” by Tarik Eren, Selim H. Kusefoglu, Richard Wool published in Journal of Applied Polymer Science, Barcelona, Volume 90, Issue 1, Pages 197-202, 2003.

[0011] EP Patent 2754306A describes an adhesive containing a polycondensate and a dienophile modified fatty acid as a cross-linking agent.

[0012] PCT Application 2005071050A1 describes a metalworking fluid comprising oil in water emulsion from a reaction product of maleic anhydride and a triglyceride oil from a plant or land animal and further reacted with water, Group IA and IIA metals, ammonium hydroxide, various amines, alkanolamines, polyols, alkoxylated alkanolamines, poly (alkylene oxide)s, or polyamines or mixtures.

[0013] US Patent 5733970 A discloses an aqueous dispersed, epoxy crosslinked maleated oil (maleated glyceride oil) microgel polymers for protective coatings.

[0014] US patent 9065132 B1 discloses lithium-ion batteries using discrete carbon nanotubes, methods for production thereof and products obtained therefrom.

[0015] US 8540902 A1 discloses a carbon-nanotube based pastes and methods for making and using the same.

[0016] US 8269021 B2 discloses an aromatic imide-based dispersant for carbon nanotubes and carbon nanotube composition comprising the same.

[0017] US Patents 6280697, 6422450 and 6514395 discloses lithiated carbon nanotubes (CNT) for providing a high energy, non-metallic anode for lithium batteries.

[0018] 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-dispersible in 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, althoughsuch 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.

[0019] Carbon nanotubes (CNTs) have attracted attention as potential electrode materials due to their high length-to-diameter (LD) ratio and specific surface area (SSA) and their low-volume resistivity. When used to form electroconductive films, organic solar cells or electrode materials, CNTs need to be dispersed in matrices such as solutions or binders. Extensive attempts have been made to develop novel dispersants or methods for uniformly dispersing CNTs in solvents or binders.

[0020] The present invention comprises a new dispersant for carbon nanotubes, including multi- walled CNTs (MWCNTs), thin-walled (single walled + double walled) CNTs, few-walled CNTs (FWCNTs) and single-walled CNTs (SWCNTs), which are employed as conductive additives in lithium-ion or sodium-ion batteries. CNT suspension is a new, highly efficient conductive agent for Li-ion batteries, which can replace traditional conductive agents such as carbon black, acetylene black, carbon nanotubes, graphene nanotubes, graphene sheets, graphite and carbon fiber. It has excellent characteristics of a high LD ratio, considerable SSA value and low volume resistivity. It can be used in various specifications of electrode materials, such as cathodes: LFP, LMFP, LCO, LMN, NCM; and anodes: graphite, LTO and Si-based etc. SUMMARY OF THE INVENTION

[0021] The present application provides a dispersant for a carbon nanotube comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) 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 (c) a base.

[0022] Another aspect of the present invention provides an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a base; wherein the maleated functionality has been partially reacted with the base; and (C) a functionalized or unfunctionalized moiety selected from the group consisting ofhydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety.

[0023] Another aspect of the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) 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 (C) a base, wherein the reaction product comprises a compound of the following structure:wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl 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.

[0024] Another aspect of the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) 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 (C) a base, wherein the reaction product is a polymer comprising the following structure:wherein n is greater than 1; wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties, with or without heteroatoms, containing from about 1 to about 36 carbon atoms; wherein R4is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, alkenylene, arylene and alkarylene moieties, with or without heteroatoms, 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.

[0025] In another aspect of the invention, the present application provides a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) 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 (c) a base; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0026] In another aspect of the invention, the present application provides a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) a base; and (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; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0027] Another aspect of the invention provides a dispersant for a carbon nanotube or a carbon nanotube composition in the form of a suspension or slurry used as a conductive agent in the formulation of electrodes in lithium-ion or sodium-ion batteries. DETAILED DESCRIPTION OF THE INVENTION

[0028] The present application provides a dispersant for a carbon nanotube or carbon nanotube composition comprising a reaction product of: (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) 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 (c) a base.

[0029] The present invention also provides dispersant for a carbon nanotube or a carbon nanotube composition comprising a reaction product of (a) a maleated natural oil with maleated functionality; (b) a base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof.

[0030] The dispersant for a carbon nanotube or a carbon nanotube composition of the present application in the form of suspension or slurry is used as a conductive agent in the formulation of electrodes in lithium-ion or sodium-ion batteries.

[0031] Natural oils are abundant, inexpensive, and are derived from sustainable sources. Natural oils are useful for synthesizing renewable compounds such as polymers, plastics, and plasticizers, which compounds are useful in a variety of compositions. A difficultly 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 with maleates to provide epoxide functional groups and 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.

[0032] 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.

[0033] 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 reference is made. The term “comprising” and “comprises of” includes the more restrictive claims such as “consisting essentially of” and “consisting of”.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] The term “reaction product” refers to a substance produced from a chemical reaction of one or more reactant substances.

[0042] 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.

[0043] The term “maleated natural oil”, as used herein, refers to natural oil containing at least one or more maleated functionality. 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.

[0044] As used herein, the term “moiety” or “moieties” refers to a part or a functional group(s) of a molecule.

[0045] 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.

[0046] 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.

[0047] The term “organic base”, as used herein, includes ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.

[0048] 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.

[0049] The term “alkali metal base” includes oxides, hydroxides, carbonates, or bicarbonates of sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr).

[0050] 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).

[0051] The term “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), hassium (Hs), meitnerium (Mt), darmstadtium (Ds) and roentgenium (Rg).

[0052] The term “dispersant” refers to an agent assisting dispersing and stabilising carbon nanotubes in a composite; a composite may be a suspension or paste or other mixture comprising nanotubes and one or more other materials; a suspension is also mixture comprising nanotubes and one or more other materials, typically a dispersant(s) and liquid vehicle(s).

[0053] The term “battery” used herein includes 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 and / or secondary batteries and / or electrochemical cells.

[0054] The “battery” used herein 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.

[0055] The term “lithium-ion battery” used herein, is used interchangeably with Li-ion battery, and lithium polymer battery.

[0056] The term "cathode active material" used herein, denotes the electrochemically active material in the cathode, e.g. the transition metal oxide intercalating / deintercalating the lithium- or sodium ions during charge / discharge of the battery. Depending on the state of the battery, i.e. charged or dis- charged, the cathode active material contains lithium or sodium ions.

[0057] The term "anode active material" used herein, denotes the electrochemically active material in the anode, e.g. carbon intercalating / deintercalating the lithium or sodium ions during charge / discharge of the battery.

[0058] The term “carbon nanotube” (CNT) used herein, means a hollow carbon structure having a diameter from about 4 nm to about 100 nm.

[0059] The “carbon nanotubes” (CNTs) used herein, can be any suitable type of carbon nanotube. For example, the carbon nanotubes can be single-wall carbon nanotubes, double-wall carbon nanotubes, few-wall carbon nanotubes, multi-wall carbon nanotubes, bundle-type carbonnanotubes, or a combination thereof. Carbon nanotubes having a high electrical conductivity may be particularly suitable.

[0060] The term “binder” used herein, can be used to form a bond between a current collector and a layer of the electrode. The binder can be polyvinyl alcohol, polyimide, ethylene-propylene- diene terpolymer, styrene-butadiene rubber, polyvinylidene difluoride (PVDF), polytetrafluoroethylene, tetrafluoroethylene-hexafluoropropylene copolymer, carboxymethyl cellulose (CMC), or a mixture thereof. The electrode may include 0.01% to 10% by weight of the binder.

[0061] The term “carbon nanotube slurry or paste” refers to an electro-conductive composite in which an electro-conductive filler is combined with carbon nanotubes.

[0062] 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 moiety by 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.

[0063] As used herein, the term "hydrophilic" means that the compound has an affinity for water, whereas "hydrophobic" means not having an affinity for water.

[0064] 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. Likewise, hydrophobic moieties have less of an 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.

[0065] The term “unreacted maleated functionality” refers to presence of an unreacted maleic anhydride compound or functionality in the reaction product of this invention, wherein, the maleated functionality are completely unreacted and intact.

[0066] 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.

[0067] 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-C30 hydrocarbyl 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.

[0068] 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.

[0069] 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 includebenzyl, 2-phenyl-ethyl, 3-phenyl-propyl, 4-phenyl-butyl, 5-phenyl-pentyl, 4-phenylcyclohexyl, 4- benzylcyclohexyl, 4-phenylcyclohexylmethyl, 4-benzylcyclohexylmethyl, and the like.

[0070] 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, and the like.

[0071] 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-C20 group. Non-limiting examples of alkylene groups include:

[0072] 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.

[0073] 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.

[0074] The structures set out below may refer to the first, second, or third structure, or combinations thereof. The succinic anhydride group may be present in the top, middle, or lower chain.

[0075] In one non-limiting embodiment, the hydrophobic moiety or the hydrophilic moiety is a hydrocarbyl alcohol, a hydrocarbyl amine, a silicon-based compound, or a combination thereof.

[0076] 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 may have a general formula. For example, the general formula for primary alcohols isthe general formula for secondary alcohols isand the general formula for tertiary alcohols iswherein R, R′ and R″ stand for different alkyl, alkylene, aryl, aralkyl, or arylene groups.

[0077] The present application provides a dispersant for a carbon nanotube composition comprising a reaction product of: (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) a functionalized or unfunctionalized moiety selected from the group consistingof hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base.

[0078] Preferably, the hydrophobic moiety is a moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 6 to about 36 carbon atoms and may contain heteroatoms; silicon-based compounds; and combinations thereof.

[0079] Preferably, the hydrophilic moiety is a moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain heteroatoms; unsubstituted or substituted polyols, wherein the unsubstituted or substituted polyols contain from about 2 to about 36 carbon atoms and may contain heteroatoms; silanes; and combinations thereof.

[0080] Preferably, the silane is functionalized with an alcohol, an amine, or combinations thereof. More preferably, the hydrophobic alcohol is selected from the group consisting of heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-octyl-1-dodecyl alcohol, 2-tertradecanol, 2-hexadecanol, 3,7-dimethyl-1-octanol, 2- propyl-1-pentanol, 4-methyl-1-pentanol, and mixtures thereof. More preferably, the hydrophilic alcohol is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, methoxypolyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentylglycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, L-Ribose, 2-deoxy-D-galactose, and mixtures thereof.

[0081] Preferably, the hydrophobic amine is selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, octadecylamine, undecyl amine, pentadecyl amine, 2-methyl butyl amine, dimethyl amine, and mixtures thereof. Preferably, the hydrophilic amine is selected from the group consisting of 2-methylpentane-1,5-diamine, diethanolamine, diisopropanolamine, serinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, N-methylglucosamine, galactosamine hydrochloride, glucosamine hydrochloride, mannosamine hydrochloride, and mixtures thereof.

[0082] Preferably, 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, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane- hydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof. Preferably, the silane is a hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2- aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

[0083] In one non-limiting embodiment, the hydrophobic moiety hydrocarbyl alcohol contains C2 to C36 carbon atoms and is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional.

[0084] In one non-limiting embodiment, the hydrocarbyl alcohol is selected from the group consisting of monohydric alcohols, dihydric alcohols, polyhydric alcohols and combinations thereof.

[0085] In one non-limiting embodiment, the amines selected from the group consisting of primary, secondary, and tertiary amines and combinations thereof, based on the number of carbon atoms or carbon groups connected to the nitrogen atom. Each classification 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, R2, R3stand for different alkyl, alkylene, aryl, aralkyl, or arylene, groups.

[0086] In one non-limiting embodiment, the hydrocarbyl amine is selected from the group consisting of primary amines, secondary amines and combinations thereof.

[0087] In one non-limiting embodiment, the hydrophobic moiety hydrocarbyl amine contains C2 to C36 carbon atoms and is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional.

[0088] In one non-limiting embodiment, the silicon-base compound is awherein R stands for different alkyl, alkylene, aryl, aralkyl, arylene, hetero groups functionalized with at least one or more alcohol, an amine or a combination thereof and n has the value of 1 to 10.

[0089] In one non-limiting embodiment, the silicon-base compound is a siloxane, or a silane functionalized with an alcohol, an amine or a combination thereof.

[0090] In one non-limiting embodiment, the silicon-based compound is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional compound.

[0091] In one non-limiting embodiment, the hydrocarbyl alcohol is selected from the group consisting of monohydric alcohols, dihydric alcohols, polyhydric alcohols and combinations thereof.

[0092] In one non-limiting embodiment, the hydrocarbyl alcohol is a hydrophobic alcohol selected from the group consisting of propanol, butanol, pentanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-octyl-1- dodecyl alcohol, 2-tertradecanol, 2-hexadecanol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4- methyl-1-pentanol and mixtures thereof.

[0093] In one non-limiting embodiment, the hydrocarbyl alcohol is a hydrophilic alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, methoxypolyethylene glycol, polypropylene glycol, hexylene glycol, glycerol, sorbitol, octanol, methyl ethyl pentanol, trimethyl pentanol, ethyl hexanol, methyl heptanol, nonanol, methyl octanol, ethyl heptanol, methyl ethyl hexanol, cyclohexanol, dimethyl heptanol, decanol, methyl nonanol, ethyl octanol, trimethyl heptanol, undecanol, methyl decanol, ethyl nonanol, dodecanol, tetradecanol, hexadecanol, octadecanol, benzyl alcohol, phenoxyethanol, neopentylglycol, trimethylol propane, methyldiethanol amine, erythritol, mannitol, xylitol, pentaerythritol, threitol, pentaerythritol, beta-cyclodextrin, L-Ribose, 2-deoxy-D-galactose and mixtures thereof.

[0094] In one non-limiting embodiment, the hydrocarbyl amine is hydrophobic amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexdecylamine, octadecylamine, undecylamine, pentadecylamine, diisopropylamine, and mixtures thereof.

[0095] In one non-limiting embodiment, the hydrocarbyl amine is hydrophilic amine is selected from the group consisting of 2-methylpentane-1,5-diamine, diethanolamine, serinol, 2-amino-2- ethyl-1,3-propanediol, dimethylamine, 2-methylbutylamine, 3-amino-1-propanol, and salts thereof.

[0096] 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, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropyl methylsiloxane and mixtures thereof.

[0097] In one non-limiting embodiment, the silicon-based compound is hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3- aminopropylsilanetriol and mixtures thereof.

[0098] Preferably, 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. More preferably, the maleated natural oil is a maleated soybean oil.

[0099] 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.

[0100] As a non-limiting, illustrative example, the maleation reaction may be performed at an elevated temperature, such as a temperature between about 150 °C and about 300 °C, alternately, between about 170 °C and about 230 °C, or, alternately, between about 200 °C and about 220 °C. The maleation reaction time may be between about 0.5 hour 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 6 hours and, in another embodiment, between about 6 hours and 10 hours.

[0101] Subsequently, the maleated natural oil can be reacted with a hydrophobic moiety or a hydrophilic moiety of a hydrocarbyl alcohol, a hydrocarbyl amine, or a silicon-based compound. This kind of reaction has been accomplished by heating at about 75 °C to about 100 °C for about 6 to about 10 hours.

[0102] In one non-limiting embodiment, the invention provides a carbon nanotube dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) 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 (c) a base.

[0103] In one non-limiting embodiment, the invention provides a dispersant for a carbon nanotube comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein themaleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base; wherein the reaction product comprises the structure:

[0104] wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl 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.

[0105] In one non-limiting embodiment, the invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) 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 (C) a base, wherein the reaction product comprises one or more structure selected from the group of the following structures:wherein R is 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 R1, R2and R3are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

[0106] In one non-limiting embodiment, the invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) 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 (C) a base, wherein the reaction product is a polymer represented by the structure:wherein n is greater than 1; wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties, with or without heteroatoms, containing from about 1 to about 36 carbon atoms; wherein R4is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, alkenylene, arylene and alkarylene moieties,with or without heteroatoms, 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.

[0107] In one non-limiting embodiment, the invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) 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 (C) a base, wherein the reaction product is a polymer comprising a structure selected from the following group of structures:wherein 1 < n < 30; wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2- hexyl-1-decyl, 2-octyl-1-dodecyl, or mixtures thereof; wherein R1, R2and R3are each,independently, hydrogen, methyl, or an unsubstituted or substituted alkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R4is -CH2CH2CH2-,or a mixture thereof.

[0108] In one non-limiting embodiment, the invention provides a carbon nanotube dispersant comprising a reaction product of (a) a maleated natural oil with maleated functionality; (b) a base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof.

[0109] In one non-limiting embodiment, the invention provides a carbon nanotube dispersant comprising a reaction product of (a) a maleated natural oil with maleated functionality; (b) a base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations, wherein the reaction product comprises one or more structure selected from the following group of structures:, and combinations thereof, wherein R is ethyl, butyl, hexyl, octyl, 2-ethylhex-1-yl, 2-butyloct-1-yl, 2-hexyldec-1-yl, 2-octyldodec-1-yl or mixtures thereof.

[0110] In one non-limiting embodiment, the invention provides a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) 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 (c) a base; (B) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0111] In one non-limiting embodiment, the invention provides a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality hasbeen partially reacted with the functionalized or unfunctionalized moiety; and (c) a base; wherein the reaction product comprises the structure:wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl 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.; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0112] In one non-limiting embodiment, the invention provides a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) 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 (c) a base; wherein the reaction product comprises a structure selected from the group of:wherein n is greater than 1; wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties, with or without heteroatoms, containing from about 1 to about 36 carbon atoms; wherein R4is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, alkenylene, arylene and alkarylene moieties, with or without heteroatoms, 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. (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0113] In one non-limiting embodiment, the invention provides a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) 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 (c) a base; wherein the reaction product comprises one or more structure selected from the group of the following structures:Docket No.: 4195H-PCwherein R is 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 R1, R2and R3are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0114] In one non-limiting embodiment, the invention provides a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) 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 (c) a base; wherein the reaction product comprises a polymer having a structure selected from the group of:wherein 1 < n < 30; wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl-1-dodecyl, or mixtures thereof; wherein R1, R2and R3are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or arylalkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R4is -CH2CH2CH2-,or a mixture thereof; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0115] In one non-limiting embodiment, the invention provides a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil with maleated functionality; (b) a base; and (c) afunctionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent mixed with an electrode active material and a binder.

[0116] In one non-limiting embodiment, the invention provides a method of preparing a carbon nanotube dispersion in lithium or sodium-ion batteries comprising: (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) 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 (c) a base; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent mixed with an electrode active material and a binder.

[0117] In one non-limiting embodiment, the invention provides a method of preparing a carbon nanotube dispersion in lithium or sodium-ion batteries comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil with maleated functionality; (b) a base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent mixed with an electrode active material and a binder.

[0118] In one non-limiting embodiment, the invention provides a dispersant for a carbon nanotube or a carbon nanotube composition in the form of a suspension or slurry used as a conductive agent in the formulation of electrodes in lithium or sodium-ion batteries.

[0119] In some embodiments, the dispersant for a carbon nanotube or a carbon nanotube composition is a polymer having a weight-average molecular weight from about 3,000 Daltons to about 20,000 Daltons and a weight-average degree of polymerization, n, of about 3 to about 20.

[0120] In some embodiments, the dispersant for a carbon nanotube or a carbon nanotube composition is a polymer having a viscosity measured at 25oC with a Brookfield viscometer ranging from about 100 to about 10,000 cps.

[0121] In some embodiments of the present invention, the suitable range of the dispersant in a carbon nanotube composition can vary from about 0.01 wt.% to about 1.0 wt.%; from about 1wt.% to about 2.5 wt.%; from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.% based on the total weight of the carbon nanotube composition.

[0122] In some embodiments of the present invention, the suitable range of the carbon nanotube in the carbon nanotube composition can vary from about 0.01 wt.% to about 1.0 wt.%; from about 1 wt.% to about 2.5 wt.%; from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.% based on the total weight of the carbon nanotube composition.

[0123] In some embodiments of the present invention, the carbon nanotube composition comprises a solvent 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.

[0124] In some embodiments of the present invention, the carbon nanotube composition comprises a solvent 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.

[0125] In some embodiments of the present invention, a lithium or sodium-ion battery comprises a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) 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 (c) a base; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0126] In some embodiments of the present invention, a lithium or sodium-ion battery comprises a carbon nanotube composition comprising (A) from about 0.01 wt. % to about 10.0 wt. % of a dispersant comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) 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 (c) a base; (B) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0127] In some embodiments, the present invention discloses a method of casting the carbon nanotube composition onto an electrode material that uses a coating technique selected from the group consisting of spin coating, slot die coating, bar drawdown coating, extrusion coating, electrophoretic coating, inkjet printing and gravure coating.

[0128] In some embodiments, the present invention discloses a method of preparing a carbon nanotube dispersion in lithium or sodium-ion battery, wherein dispersion of the carbon nanotube in solvent is accomplished using an apparatus selected from the group consisting of an ultrasonicator, a homogenator, a spiral mixer, a planetary mixer, a disperser, a ball miller and a blending mixer.

[0129] The reactions and compositions according to the application may be analyzed by known techniques. Especially preferred are the techniques of13C 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.

[0130] 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

[0131] Example A: Grafting of maleic anhydride onto natural oils

[0132] Example A1: Grafting of maleic anhydride onto soybean oil

[0133] 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. 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.

[0134] Example A2: Grafting of maleic anhydride onto palm oil

[0135] 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%.

[0136] Example A3: Grafting of maleic anhydride onto canola oil

[0137] 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%.

[0138] Example A4: Grafting of maleic anhydride onto sunflower oil

[0139] 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%.

[0140] Example A5: Grafting of maleic anhydride onto castor oil

[0141] 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 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%.

[0142] Example A6: Grafting of maleic anhydride onto chickpea oil

[0143] 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%.

[0144] Example A7: Grafting of maleic anhydride onto clary sage oil

[0145] 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%.

[0146] Example B: Salts of Maleated natural oils

[0147] Example B1: Sodium salt of maleated soybean oil from aqueous sodium hydroxide In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of product from maleation reaction 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%.

[0148] Example B2: Sodium salt of maleated palm oil from aqueous sodium hydroxide In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction A2 was heated to 90 ˚ C, and a mixture of 18.04 g (2 mole equivalents based on palm oil) of 50% aqueous sodium hydroxide and 45 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%.

[0149] Example B3: Sodium salt of maleated canola oil from aqueous sodium hydroxide

[0150] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction A3 was heated to 90 ˚C, and a mixture of 18.25 g (2 mole equivalents based on canola oil) of 50% aqueous sodium hydroxide and 45 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%.

[0151] Example B4 : Sodium salt of maleated sunflower oil from aqueous sodium hydroxide

[0152] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction A4 was heated to 90 ˚C, and a mixture of 18.26 g (2 mole equivalents based on sunflower oil) of 50% aqueous sodium hydroxide and 45 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%.

[0153] Example B5: Sodium salt of maleated castor oil from aqueous sodium hydroxide

[0154] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction A5 was heated to 90 ˚C, and a mixture of 17.15 g (2 mole equivalents based on castor oil) of 50% aqueous sodium hydroxide and 45 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%.

[0155] Example C1 : Sodium salt of maleated soybean oil from sodium carbonate

[0156] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of product from maleation reaction A1 was heated to 90 ˚C, and 27.86 g (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%.

[0157] Example D : Sodium calcium salt of maleated natural oil

[0158] Example D1: Sodium calcium salt of maleated soybean oil from calcium carbonate and sodium carbonate (7:3 ratio)

[0159] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of product from maleation reaction A1 was heated to 90 ˚C, and a mixture of 8.36 g (0.9 mole equivalents based on soybean oil) of sodium carbonate and 17.8 g (2.1 mole equivalents based on soybean oil) of calcium 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 60 weight % solids and was characterized by IR. Yield was >96%.

[0160] Example D2: Sodium calcium salt of maleated palm oil from calcium carbonate and sodium carbonate (7:3 ratio)

[0161] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 122 g of product from maleation reaction A2 was heated to 90 ˚C, and a mixture of 11.55 g (0.9 mole equivalents based on palm oil) of sodium carbonate and 24.6 g (2.1 mole equivalents based on palm oil) of calcium carbonate dissolved in 122 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 60 weight % solids and was characterized by IR. Yield was >96%.

[0162] Example D3: Sodium calcium salt of maleated canola oil from calcium carbonate and sodium carbonate (7:3 ratio)

[0163] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 122 g of product from maleation reaction A3 was heated to 90 ˚C, and a mixture of 11.3 g (0.9 mole equivalents based on canola oil) of sodium carbonate and 24 g (2.1 mole equivalents based on canola oil) of calcium carbonate dissolved in 122 g of water wasadded over 3 hours, controlling the foam formation. The reaction was held at 90 ˚C for 3 hours. The product contained 60 weight % solids and was characterized by IR. Yield was >96%.

[0164] Example D4: Sodium calcium salt of maleated sunflower oil from calcium carbonate and sodium carbonate (7:3 ratio) In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 122 g of product from maleation reaction A4 was heated to 90 ˚ C, and a mixture of 11.55 g (0.9 mole equivalents based on sunflower oil) of sodium carbonate and 24.6 g (2.1 mole equivalents based on sunflower oil) of calcium carbonate dissolved in 122 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 60 weight % solids and was characterized by IR. Yield was >96%.

[0165] Example D5: Sodium calcium salt of maleated castor oil from calcium carbonate and sodium carbonate (7:3 ratio) In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 122 g of product from maleation reaction A5 was heated to 90 ˚ C, and a mixture of 10.6 g (0.9 mole equivalents based on castor oil) of sodium carbonate and 22.5 g (2.1 mole equivalents based on castor oil) of calcium carbonate dissolved in 122 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 60 weight % solids and was characterized by IR. Yield was >96%.

[0166] Example E1: Calcium salt of maleated soybean oil from calcium carbonate In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of product from maleation reaction A1 was heated to 90 ˚C, and a solution of 25.5 g (3 mole equivalents based on soybean oil) of calcium carbonate 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 60 weight % solids and was characterized by IR. Yield was >96%.

[0167] Example F1: Sodium salt of maleated soybean oil from aqueous sodium hydroxide In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction 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 gof 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%.

[0168] Example G1: Sodium salt of maleated soybean oil reacted with hydrophobic 2-octyl- 1-dodecanol and hydrophilic glycerol

[0169] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of maleated soybean oil, produced as in Example A1, and 38.17 g (1.5 mole equivalents, relative to maleated soybean oil) of 2-octyl-1-dodecanol, and the mixture was heated at 90 °C for 6 hours. Glycerol (7.85 g, 1 mole equivalent, relative to maleated soybean oil) was added, and the mixture was heated at 90 °C for another 6 hours. The reaction mixture was cooled to 85 °C, and 5.1 g (0.75 mole equivalent, relative to maleated soybean oil) of 50 wt% sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 3 hours.

[0170] Example G2: Sodium salt of maleated soybean oil reacted with hydrophilic glycerol

[0171] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 198 g of maleated soybean oil, produced as in Example A1, and 4.71 g (0.3 mole equivalent relative to maleated soybean oil) of glycerol were combined, heated to 40 °C and held at 40 °C for 2 hours. The amber liquid product was characterized by NMR and IR. Aqueous sodium hydroxide (50%, 13.64 g, 2.0 mole equivalents) was added over 30 minutes, and the mixture was held at 40 °C for 2 hours. Water was added to the viscous mixture to obtain 60% solids solution. The amber liquid product was characterized by NMR and IR. Yield was >98%.

[0172] Example G3: Sodium salt of maleated soybean oil reacted with hydrophobic castor oil

[0173] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 100 g of maleated soybean oil, produced as in Example A1, and 32.8 g (0.4 mole equivalent relative to maleated soybean oil) of castor oil were combined, heated to 80 °C and held at 80 °C for 2-6 hours. The amber, viscous, crosslinked product was characterized by NMR and IR, and GC indicated <5% of residual castor oil. Yield of maleated soybean oil reacted with castor oil was >96%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 100 g of the maleated soybean oil reacted with castor oil was heatedto 85 °C. Water and 50% aqueous sodium hydroxide were added over 60 minutes to create a final solution that was 50 weight % solids, and the mixture was held at 85 °C for 4 hours. The amber liquid product was characterized by NMR and IR. Yield of the sodium salt of maleated soybean oil reacted with castor oil was >98%.

[0174] Example G4: Sodium salt of maleated soybean oil reacted with lysine

[0175] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 150 g of maleated soybean oil, produced as in Example A1, and 5.73 g (0.5 mole equivalent relative to maleated soybean oil) of lysine were combined, heated to 100 °C and held at 100 °C for 8 hours. The amber, viscous, crosslinked product was characterized by NMR and IR. The mixture was cooled to 50 °C. Water and 30.3 g of 50% aqueous sodium hydroxide were added over 60 minutes to create a final solution that was 50 weight % solids, and the mixture was held at 50 °C for 4 hours. The amber liquid product was characterized by NMR and IR. Yield of sodium salt of maleated soybean oil reacted with lysine was >98%.

[0176] Example G5: Sodium salt of maleated soybean oil reacted with 1 equivalent of diethanolamine

[0177] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 150 g of maleated soybean oil, produced as in Example A1, and 150 g of water were heated to 90 °C for 2 h. The mixture was cooled 60 °C and 15.1 g (1 mole equivalent relative to maleated soybean oil) of diethanolamine diluted in 150 g of water was added over 30-45 minutes. The reaction mixture was held at 60 °C for 4-6 hours. The viscous, biphasic mixture was neutralized by adding 9.5 g (0.9 mole equivalent relative to maleated soybean oil) of 50 wt% aqueous sodium hydroxide over 15 minutes, and the mixture was held at 60 °C for 1-2 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.

[0178] Example G6: Sodium salt of maleated soybean oil reacted with 2 equivalents of diethanolamine

[0179] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 150 g of maleated soybean oil, produced as in Example A1, and 150 g of water were heated to 90 ˚ C for 2 h. The mixture was cooled 60 °C and 30.2 g (2 mole equivalents relative to maleated soybean oil) of diethanolamine diluted in 150 g of water was added over 30-45minutes. The reaction mixture was held at 60 °C for 4-6 hours. The viscous, biphasic mixture was neutralized by adding 9.5 g (0.9 mole equivalent relative to maleated soybean oil) of 50 wt% aqueous sodium hydroxide over 15 minutes, and the mixture was held at 60 °C for 1-2 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.

[0180] Example G7: Sodium salt of maleated soybean oil reacted with hydrophobic 1-hexanol and hydrophilic glycerol

[0181] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of maleated soybean oil, produced as in Example A1, and 26.8 g (1.5 mole equivalents relative to maleated soybean oil) of 1-hexanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (16.1 g, 1.0 mole equivalent relative to maleated soybean oil) was added, and the mixture was held at 85 °C for an additional 6 hours. Aqueous sodium hydroxide (50 wt%, 10.5 g, 0.75 mole equivalent relative to maleated soybean oil) was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0182] Example G8: Sodium salt of maleated soybean oil reacted with hydrophobic 2- ethylhexanol and hydrophilic glycerol

[0183] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 181 g of maleated soybean oil, produced as in Example A1, and 31.1 g (1.5 mole equivalents relative to maleated soybean oil) of 2-ethylhexanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (14.7 g, 1.0 mole equivalent relative to maleated soybean oil) 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%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 98.9 g of maleated soybean oil reacted with 2-ethylhexanol and glycerol was heated to 85 °C, 4.16 g (0.75 mole equivalent) of 50% aqueous sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0184] Example G9: Sodium salt of maleated soybean oil reacted with hydrophobic castor oil and 2-ethylhexanol

[0185] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of maleated soybean oil, produced as in Example A1, and 49.0 g (0.3 mole equivalent relative to maleated soybean oil) of castor oil were combined, heated to 85 °C and held at 85 °C for 6 hours. The amber, viscous product was characterized by NMR and IR, and GC indicated <5% of residual castor oil.2-Ethylhexanol (34.4 g, 1.5 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. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, the maleated soybean oil reacted with castor oil and 2- ethylhexanol was heated to 85 °C, 10.6 g of 50% aqueous sodium hydroxide (0.75 mole equivalent) was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0186] Example G10: Sodium salt of maleated soybean oil reacted with hydrophobic 2- ethylhexanol and castor oil and hydrophilic glycerol

[0187] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 85 g of maleated soybean oil, produced as in Example A1, and 14.7 g (1.5 mole equivalents relative to maleated soybean oil) of 2-ethylhexanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (3.45g, 0.5 mole equivalent) and castor oil (92.7 g, 1.0 mole equivalent) were added, and the mixture was heated to 90 °C and held at 90 °C for 6 hours. The product was characterized by NMR and IR. Yield was >96%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, the maleated soybean oil reacted with 2-ethylhexanol, glycerol and castor oil was heated to 85 °C, 4.50 g (0.75 mole equivalent) of 50% aqueous sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0188] Example G11: Sodium salt of maleated soybean oil reacted with hydrophobic dodecanol and hydrophilic glycerol

[0189] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of maleated soybean oil, produced as in Example A1, and 48.9 g (1.5 mole equivalents relative to maleated soybean oil) of dodecanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (16.1 g, 1.0 mole equivalent) was added, and the mixturewas held at 85 °C for an additional 6 hours. The product was characterized by NMR and IR. Yield was >96%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, the maleated soybean oil reacted with dodecanol and glycerol was heated to 85 °C, 10.50 g (0.75 mole equivalent) of 50% aqueous sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0190] Example G12: Sodium salt of maleated soybean oil reacted with hydrophobic 2-octyl- 1-dodecanol and hydrophilic glycerol

[0191] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 260 g of maleated soybean oil, produced as in Example A1, and 97.7 g (1.5 mole equivalents relative to maleated soybean oil) of 2-octyl-1-dodecanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (20.1 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. The product was characterized by NMR and IR. Yield was >96%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, the maleated soybean oil reacted with 2-octyl-1-dodecanol and glycerol was heated to 85 °C, 13.1 g (0.75 mole equivalent) of 50% aqueous sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0192] Example G13: Sodium salt of maleated soybean oil reacted with hydrophobic eicosanol and hydrophilic glycerol

[0193] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of maleated soybean oil, produced as in Example A1, and 78.4 g (1.5 mole equivalents relative to maleated soybean oil) of eicosanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (10.5 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. Aqueous sodium hydroxide (50 wt%, 10.5 g, 0.75 mole equivalent relative to maleated soybean oil) was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0194] Example H1: Maleated soybean oil reacted with hydrophilic 1,3-propanediol and hydrophobic 2-octyldodecanol

[0195] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 125 g of MSBO made according to Example A1 and 3.36 g (0.4 mole equivalent relative to MSBO) of 1,3-propanediol were combined, heated to 85 °C and held at 85 °C for 2 hours. The amber, viscous, crosslinked product was characterized by NMR and IR. 2- Octyldodecanol (65.8 g, 2 mole equivalents) was added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous, crosslinked product was characterized by NMR and IR. Yield was >96%.

[0196] Example H2: Maleated soybean oil reacted with hydrophobic behenyl alcohol and hydrophilic 1,3-propanediol

[0197] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 150 g of MSBO made according to Example A1 and 69.1 g (1.5 mole equivalents relative to MSBO) of behenyl alcohol were combined, heated to 85 °C and held at 85 °C for 8 hours. 1,3-Propanediol (10.2 g, 1.0 mole equivalent) was added, and the mixture was heated to 100 °C and held at 100 °C for 6 hours. The product was characterized by NMR and IR. Yield was >96%.

[0198] Example 1: Preparation of Solvent-based CNT Dispersions

[0199] Dispersant (0.3 g) was fully dissolved in 30 g of N-methyl-2-pyrrolidone (NMP, Micropure™ EG from Ashland) solvent at a temperature of 5-35 ℃ and a mixeer speed of 200- 1000 rpm for about 1-8 hours, until no particle was observable by the eye. Carbon nanotubes (JiangSu Cnano, 0.3 g) were added to the NMP mixture, and the mixture in a closed container was shaken by hand for 10 seconds and then pre-mixed with a Vortexer twice for 30 seconds or with a Thinky mixer for 5 minutes at 2000 rpm. The container was then sonicated for 15 minutes and then subjected to ultrasonic mixing, cycling on for 5 seconds and then off for 10 seconds, for 5 minutes. The container was removed from the ultrasonic mixer and cooled.

[0200] Example 2: Analysis of Solvent-based CNT Dispersions

[0201] Solvent-based CNT dispersions, prepared according to Example 1 using different proportions of the dispersant of Example G1 and ethylcellulose (Aqualon™ EC-N4, Ashland), were analyzed for particle size distribution and resistivity. As can be seen from the results in Table1, the dispersant of Example G1 improves the particle size distribution and resistivity of the CNT dispersion, relative to ethylcellulose. Table 1. Properties of CNT Dispersions Using the Dispersant of Example G1

[0202] Solvent-based CNT dispersions, prepared according to Example 1 using different proportions of the dispersant of Example G1 and polyvinylpyrrolidone (PVP) (PVP K-30, Ashland), were analyzed for particle size distribution and resistivity. As observed from the results in Table 2, the dispersant of Example G1 improves the particle size distribution and similar resistivity of the CNT dispersion, relative to PVP. Table 2. Properties of CNT Dispersions Using the Dispersant of Example G1

[0203] 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 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).

Claims

We claim:

1. A dispersant for a carbon nanotube comprising a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) 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 (C) a base.

2. The dispersant 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 dispersant according to claim 2, wherein the maleated natural oil is a maleated soybean oil.

4. The dispersant according to claim 1, wherein the reaction product comprises a maleated functionality functionalized with a hydrophobic moiety, a maleated functionality functionalized with a hydrophilic moiety, unreacted maleated functionality or combinations thereof.

5. The dispersant according to claim 1, wherein the hydrophobic moiety is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl amines, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; unsubstituted or substituted polyols, with or without additionalheteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.

6. The dispersant according to claim 1, wherein the hydrophilic moiety is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols, with or without additional heteroatoms, containing from about one to about five carbon atoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl amines, with or without heteroatoms, containing from about one to about five carbon atoms; unsubstituted or substituted polyols, with or without additional heteroatoms, containing from about two to about 36 carbon atoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.

7. The dispersant according to claim 6, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.

8. The dispersant according to claim 5, wherein 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, behenyl alcohol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4- methyl-1-pentanol, and mixtures thereof.

9. The dispersant according to claim 6, wherein the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.

10. The dispersant according to claim 6, 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, hexylene glycol, sorbitol, neopentylglycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof.

11. The dispersant according to claim 5, 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.

12. The dispersant according to claim 6, wherein the hydrophilic moiety is that of an amine selected from the group consisting of 2-methylpentane-1,5-diamine, 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.

13. The dispersant according to claim 5, wherein 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, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.

14. The dispersant according to claim 6, wherein the silane is a hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3- aminopropylsilanetriol, and mixtures thereof.

15. The dispersant according to claim 1, wherein the base is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

16. The dispersant according to claim 15, 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.

17. The dispersant according to claim 15, 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.

18. The dispersant according to claim 16, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

19. The dispersant according to claim 16, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

20. The dispersant according to claim 16, 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.

21. The dispersant according to claim 16, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.

22. The dispersant according to claim 1, wherein the reaction product comprises a compound of the following structure:wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl 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.

23. The dispersant according to claim 1, wherein the reaction product is a polymer comprising the following structure:wherein n is greater than 1; wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties, with or without heteroatoms, containing from about 1 to about 36 carbon atoms; wherein R4is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, alkenylene, arylene and alkarylene moieties, with or without heteroatoms, 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.

24. The dispersant according to claim 22, wherein the reaction product comprises one or more structure selected from the group of the following structures:wherein R is 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 R1, R2and R3are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or arylalkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

25. The dispersant according to claim 23, wherein the reaction product is a polymer comprising one or more of the following structures:Docket No.: 4195H-PCTwherein 1 < n < 30; wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl-1-dodecyl, or mixtures thereof; wherein R1, R2and R3are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or arylalkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R4is -CH2CH2CH2-, or a mixture thereof.

26. The dispersant according to claim 23, wherein the reaction product is a polymer having a weight-average molecular weight from about 3,000 Daltons to about 20,000 Daltons and a weight-average degree of polymerization, n, of about 3 to about 20.

27. The dispersant according to claim 23, wherein the reaction product is a polymer having a viscosity measured at 25oC with a Brookfield viscometer ranging from about 100 to about 10,000 cps.

28. A carbon nanotube composition comprising (a) about 0.01 wt. % to about 10.0 wt. % of the dispersant of claim 1; (b) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (c) a solvent.

29. The carbon nanotube composition according to claim 28, wherein the carbon nanotube is mixed at a weight ratio of 1:0.001 to 1:10 with the dispersant.

30. The carbon nanotube composition according to claim 28, wherein the carbon nanotube is selected from a 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-wall carbon nanotube, a multi-walled carbon nanotube, a carbon nanohorn, a carbon nanofiber, short nanotubes, carbon particles nanotubes, and combinations thereof.

31. The carbon nanotube composition according to claim 28, wherein the solvent is 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.

32. The carbon nanotube composition according to claim 28, wherein the solvent is selected from the group consisting of water, methanol, ethanol, isopropyl alcohol, propyl alcohol, butanol, terpineol, acetone, methylethyl ketone, ethyl isobutyl ketone, methylisobutyl ketone, ethyleneglycol, ethyleneglycol methylether, ethyleneglycol mono-n-propylether, propyleneglycol, propyleneglycol methylether, propyleneglycol ethylether, propyleneglycol butylether, propyleneglycol propylether, 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 methylester, aniline, N-methylaniline, hexane, chloroform, toluene, propylene glycol monomethyl ether acetate (PGMEA) and combinations thereof.

33. A method of casting the carbon nanotube composition of claim 28 onto an electrode material that uses a coating technique selected from the group consisting of spin coating, slot die coating, bar drawdown coating, extrusion coating, electrophoretic coating, inkjet printing and gravure coating.

34. A lithium-ion or sodium-ion battery comprising the carbon nanotube composition of claim 28.

35. A lithium-ion or sodium-ion battery composition comprising the carbon nanotube composition of claim 28.

36. A method of preparing a carbon nanotube dispersion for use in a lithium-ion or sodium-ion battery composition comprising mixing (a) the carbon nanotube composition of claim 28, (b) an electrode active material, and (c) a binder.

37. The method of preparing a carbon nanotube dispersion according to claim 36, wherein dispersion of the carbon nanotube in solvent is accomplished using an apparatus selected from the group consisting of an ultrasonicator, a homogenator, a spiral mixer, a planetary mixer, a disperser, a ball miller and a blending mixer.

38. A dispersant for a carbon nanotube comprising a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a base; wherein the maleated functionality has been partially reacted with the base; and (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.

39. The dispersant according to claim 38, wherein the hydrophobic moiety is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, wherein the alcohols and amines containfrom about 6 to about 36 carbon atoms and may contain additional heteroatoms; unsubstituted or substituted polyols, with or without additional heteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.

40. The dispersant according to claim 38, wherein the hydrophilic moiety is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain additional heteroatoms; unsubstituted or substituted polyols, wherein the unsubstituted or substituted polyols contain from about 2 to about 36 carbon atoms and may contain additional heteroatoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.

41. The dispersant according to claim 40, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.

42. The dispersant according to claim 39, wherein 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, behenyl alcohol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4- methyl-1-pentanol, and mixtures thereof.

43. The dispersant according to claim 40, wherein the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.

44. The dispersant according to claim 40, 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, hexylene glycol, sorbitol, neopentylglycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof.

45. The dispersant according to claim 39, 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.

46. The dispersant according to claim 40, wherein the hydrophilic moiety is that of an amine selected from the group consisting of 2-methylpentane-1,5-diamine, 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.

47. The dispersant according to claim 39, wherein 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, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.

48. The dispersant according to claim 40, wherein the silane is a hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3- aminopropylsilanetriol, and mixtures thereof.

49. The dispersant according to claim 38, wherein the base is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

50. The dispersant according to claim 49, 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.

51. The dispersant according to claim 49, 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.

52. The dispersant according to claim 50, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

53. The dispersant according to claim 50, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

54. The dispersant according to claim 50, 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.

55. The dispersant according to claim 50, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.

56. The dispersant according to claim 38, 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.

57. The dispersant according to claim 38, wherein the maleated natural oil is a maleated soybean oil.

58. The dispersant for a carbon nanotube according to claim 38, wherein the reaction product comprises one or more structure selected from the following group of structures:, and combinations thereof, wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-buty-1-loctyl, 2- hexyl-1-decyl, 2-octyl-1-dodecyl or mixtures thereof.

59. A carbon nanotube composition comprising (a) about 0.01 wt. % to about 10.0 wt. % of the dispersant of claim 38; (b) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and(c) a solvent.

60. The carbon nanotube composition according to claim 59, wherein the carbon nanotube is mixed at a weight ratio of 1:0.001 to 1:10 with the dispersant.

61. The carbon nanotube composition according to claim 59, wherein the carbon nanotube is selected from a 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-wall carbon nanotube, a multi-walled carbon nanotube, a carbon nanohorn, a carbon nanofiber, short nanotubes, carbon particles nanotubes, and combinations thereof.

62. The carbon nanotube composition according to claim 59, wherein the solvent is 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.

63. The carbon nanotube composition according to claim 59, wherein the solvent is selected from the group consisting of water, methanol, ethanol, isopropyl alcohol, propyl alcohol, butanol, terpineol, acetone, methylethyl ketone, ethyl isobutyl ketone, methylisobutyl ketone, ethyleneglycol, ethyleneglycol methylether, ethyleneglycol mono-n-propylether, propyleneglycol, propyleneglycol methylether, propyleneglycol ethylether, propyleneglycol butylether, propyleneglycol propylether, 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.

64. A method of casting the carbon nanotube composition of claim 59 onto an electrode material that uses a coating technique selected from the group consisting of spin coating, slot die coating, bar drawdown coating, extrusion coating, electrophoretic coating, inkjet printing and gravure coating.

65. A lithium-ion or sodium-ion battery comprising the carbon nanotube composition of claim 59.

66. A lithium-ion or sodium-ion battery composition comprising the carbon nanotube composition of claim 59.

67. A method of preparing a carbon nanotube dispersion for use in a lithium-ion or sodium-ion battery composition comprising mixing (a) the carbon nanotube composition of claim 59, (b) an electrode active material, and (c) a binder.

68. The method of preparing a carbon nanotube dispersion according to claim 67, wherein dispersion of the carbon nanotube in solvent is accomplished using an apparatus selected from the group consisting of an ultrasonicator, a homogenator, a spiral mixer, a planetary mixer, a disperser, a ball miller and a blending mixer.

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