Dispersant comprising modified maleated natural oil containing a lactam moiety, 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, comprising a natural oil with maleated functionality; and (B) at least one lactam having at least one hydroxyl functional group. Also, 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; (B) at least one lactam having at least one hydroxyl functional group; and (C) a base. Also, 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. The dispersant for carbon nanotubes or carbon nanotube compositions comprising reaction products of modified natural oil having lactam moieties are used in lithium-ion or sodium-ion batteries.

Description

DISPERSANT COMPRISING MODIFIED MALEATED NATURAL OIL CONTAINING A LACTAM MOIETY, SALTS FOR CARBON NANOTUBES AND CARBON NANOTUBE COMPOSITIONFIELD 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) at least one lactam having at least one hydroxyl functional group. Also, 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, and (C) a base. Also, 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base.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. Forexample, these unsaturated groups can be reacted to provide epoxide functional groups or succinic anhydride functional groups. Despite these chemical modifications, the maleated natural oils can still exhibit limited properties such as insolubility or non-dispersibility in water and alcohols. Accordingly, there is a need for further modified maleated natural oils which do not exhibit the limited properties of maleated natural oils.

[0004] 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 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 OsamaM. ¬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 Applications 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, although such natural oils are an importantrenewable 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 lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

[0022] 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) 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), which has the structure:

[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) 1-(2-aminoethyl)-2-pyrrolidone, which has the structure:

[0024] Another aspect of the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; and (B) 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), wherein the reactionproduct is a maleated soybean oil substituted with one, two or three 1 -(2-hydroxyethyl)-2- pyrrolidone (HEP) moieties, and the reaction product comprises one or more structure(s) selected from:

[0025] Another aspect of the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated soybean oil, comprising soybean oil with maleated functionality; and (B) a 1-(2-aminoethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)-2-pyrrolidone moieties, and the reaction product comprises one or more structure(s) selected from:wherein, R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms.

[0026] 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base.

[0027] 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base.

[0028] Another aspect of the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; (B) 1-(2-hydroxyethyl)-2-pyrrolidone and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium. Particularly, the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)-2-pyrrolidone moieties, and the reaction product comprises one or more structure(s) selected from:

[0029] Yet 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and, (D) optionally, a base.

[0030] Another aspect of the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) a base, wherein the reaction product comprises a compound having the structure:wherein R7is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium; and the reaction product comprising one or more structure(s) selected from:wherein R7is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl-1-dodecyl, or mixtures thereof; and wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

[0031] 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; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) a base, wherein the reaction product is a polymer comprising the structure:wherein n is greater than 1;wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium; and the reaction product is a polymer comprising one or more structure(s) selected from:wherein 1 < n < 30; wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R11is selected from the group consisting of -CH2CH2CH2-, and mixtures thereof.

[0032] Another aspect of the present 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; and (b) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (B) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0033] Another aspect of the present 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 lactam moiety having at least one hydroxyl, thiol or amine functional group; and (c) a base; (B) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0034] Another aspect of the present 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 lactam moiety having at least one hydroxyl, thiol or amine functional group; (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (d) optionally, a base; (B) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0035] Another aspect of the present 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; and (b) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (d) optionally, a base, wherein the reaction product is a polymer; (B) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0036] In another aspect of the invention, the present application provides a method of preparing a lithium-ion or sodium-ion battery composition comprising mixing: (A) a carbon nanotubecomposition comprising (i) 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 lactam moiety having at least one hydroxyl, thiol or amine functional group, (ii) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube, and (iii) a solvent; (B) an electrode active material; and (C) a binder.

[0037] In another aspect of the invention, the present application provides a method of preparing a lithium-ion or sodium-ion battery composition comprising mixing: (A) a carbon nanotube composition comprising (i) 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 lactam moiety having at least one hydroxyl, thiol or amine functional group; and (c) a base; (ii) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (iii); a solvent; (B) an electrode active material; and (C) a binder.

[0038] In another aspect of the invention, the present application provides a method of preparing a lithium-ion or sodium-ion battery composition comprising mixing: (A) a carbon nanotube composition comprising (i) 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 lactam moiety having at least one hydroxyl, thiol or amine functional group; (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (d) optionally, a base; (ii) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (iii); a solvent; (B) an electrode active material; and (C) a binder.

[0039] In another aspect of the invention, the present application provides a method of preparing a lithium-ion or sodium-ion battery composition comprising mixing: (A) a carbon nanotube composition comprising (i) 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 lactam moiety having at least one hydroxyl, thiol or amine functional group; (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (d) optionally, abase, wherein the reaction product is a polymer; (ii) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (iii) a solvent; (B) an electrode active material; and (C) a binder.

[0040] Another aspect of the invention provides a dispersant for a carbon nanotube, or a carbon nanotube composition used in lithium-ion or sodium-ion batteries. DETAILED DESCRIPTION OF THE INVENTION

[0041] 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 lactam having at least one hydroxyl, thiol or amine functional group. Also, 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, and (C) a base. Also, 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base.

[0042] The dispersant for a carbon nanotube or the carbon nanotube composition of the present application is used in the form of a suspension or slurry as a conductive agent in the formulation of electrodes in lithium-ion or sodium-ion batteries.

[0043] 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 anhydridefunctional 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.

[0044] 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.

[0045] 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”.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] The use of the term “at least one” will be understood to include one as well as any quantity more than one, including but not limited to, 1, 2, 3, 4, 5, 10, 15, 20, 30, 40, 50, 100, etc. The term “at least one” may extend up to 100 or 1000 or more depending on the term to which it is attached.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] The term “reaction product” refers to a substance produced from a chemical reaction of one or more reactant substances.

[0055] 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.

[0056] The term “maleated natural oil”, as used herein, refers to natural oil contains at least one or more maleated functionalities. Since the carbon-carbon double bond of maleic anhydride becomes saturated during its attachment to unsaturated fatty acid chains, whether the “maleation” reaction is by an “ene” reaction, a Diels-Alder reaction or a radical addition to the double bond ofmaleic anhydride, the “maleated functionality” could also be considered a succinyl anhydride moiety attached to one or more fatty acid chain in the natural oil

[0057] As used herein, the term “moiety” or “moieties” refers to a part or a functional group(s) of a molecule.

[0058] 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 might also be called by one of ordinary skill in the art succinic anhydride, succinic acid, succinate salt or succinate half ester functionality.

[0059] 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.

[0060] The term “organic base”, as used herein, includes ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.

[0061] 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 transitionmetals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.

[0062] The term “alkali metal base” includes oxides, hydroxides, carbonates, or bicarbonates of sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr).

[0063] 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).

[0064] 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).

[0065] The term “dispersant” refers to an agent assisting dispersing and stabilizing 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).

[0066] The term “battery” used herein include a single electrochemical cell, or unicell, and / or one or more electrochemical cells connected in series and / or in parallel as known by those of skill in the art. Furthermore, the term “battery” includes, but is not limited to, rechargeable batteries and / or secondary batteries and / or electrochemical cells.

[0067] 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.

[0068] The term “lithium-ion battery” used herein, is used interchangeably with Li-ion battery, and lithium polymer battery.

[0069] 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 ions 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 more or less lithium ions.

[0070] The term "anode active material" used herein, denotes the electrochemically active material in the anode, e.g. carbon intercalating / deintercalating the lithium ions or sodium ions during charge / discharge of the battery.

[0071] The term “carbon nanotube” (CNT) used herein, means a hollow carbon structure having a diameter from about 4 nm to about 100 nm.

[0072] 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 carbon nanotubes, or a combination thereof. Carbon nanotubes having a high electrical conductivity may be particularly suitable.

[0073] 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.

[0074] The term “carbon nanotube slurry or paste” refers to an electro-conductive composite in which an electro-conductive filler is combined with carbon nanotubes.

[0075] 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, Michaeladdition, aldol condensation, Canizzaro reaction, Mannich reaction, Claisen 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.

[0076] As used herein, the term "hydrophilic" means that the compound has an affinity for water, whereas "hydrophobic" means not having an affinity for water.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] The term “aryl” refers to a functionalized or unfunctionalized, monovalent, aromatic hydrocarbyl group optionally having one or more heteroatoms. The definition of aryl includescarbocyclic 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.

[0082] The term “aralkyl” refers to an alkyl group comprising one or more aryl substituent(s) wherein "aryl" and "alkyl" are as defined above. Non-limiting examples of aralkyl groups include benzyl, 2-phenyl-ethyl, 3-phenyl-propyl, 4-phenyl-butyl, 5-phenyl-pentyl, 4-phenylcyclohexyl, 4- benzylcyclohexyl, 4-phenylcyclohexylmethyl, 4-benzylcyclohexylmethyl, and the like.

[0083] 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.

[0084] 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:

[0085] 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, naphthalene, pyridinylene, and the like.

[0086] 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.

[0087] 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 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, maleatedflaxseed oils, maleated grapeseed oils, maleated palm 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.

[0088] 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.

[0089] As a non-limiting, illustrative example, the maleation reaction may be performed at elevated temperatures, such as a temperature between about 150 °C and about 300 °C, alternatively, between about 170 °C and about 230 °C, or alternatively, between about 200 °C and about 220 °C. The reaction time may be between about 0.5 hours and about 14 hours. In one embodiment, the reaction time is between about 1 hour and about 5 hours and, in another embodiment, between about 2 hours and about 6 hours and, in another embodiment, between about 6 hours and about 10 hours.

[0090] During maleation, the mole ratio of maleic anhydride to natural oil in some embodiments is equal to 1, in other embodiments from 1 to 2, in other embodiments from 1 to 2.8 and in still other embodiments from 1 to 3.2 moles of maleic anhydride for each mole of natural oil.

[0091] In one non-limiting embodiment, 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 lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

[0092] In one non-limiting embodiment, 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) 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), which has the structure:.

[0093] In one non-limiting embodiment, 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) 1-(2-aminoethyl)-2-pyrrolidone, which has the structure:

[0094] In one non-limiting embodiment, the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; and (B) 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), wherein the reaction product is a maleated soybean oil substituted with one, two or three l-(2- hydroxyethyl)-2-pyrrolidone (HEP) moieties, and the reaction product comprises one or more structure(s) selected from:

[0095] In one non-limiting embodiment, the present invention provides a dispersant for acarbon nanotube comprising a reaction product of (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; and (B) a 1-(2-aminoethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)-2- pyrrolidone moieties, and the reaction product comprises one or more structure(s) selected from:; wherein, R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms.

[0096] In one non-limiting embodiment, 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl,alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base.

[0097] In one non-limiting embodiment, the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; (B) 1-(2-hydroxyethyl)-2-pyrrolidone and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium. Particularly, the reaction product is a sodium salt of a maleated natural oil substituted with one, two or three 1-(2- hydroxyethyl)-2-pyrrolidone moieties comprising one or more structure(s) selected from: Na

[0098] In one non-limiting embodiment, 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; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and, (D) optionally, a base.

[0099] In one non-limiting embodiment of the aforementioned invention, the maleated natural oil (A) is a maleated soybean oil. In another non-limiting embodiment of the aforementioned invention, the lactam moiety having at least one hydroxyl, thiol or amine functional group (B) is that of 1-(2-hydroxyethyl)-2-pyrrolidone (HEP). In another non-limiting embodiment of the aforementioned invention, the base (D) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof. In another non-limiting embodiment of the aforementioned invention, the hydrophobic moiety and / or hydrophilic moiety is selected from those of a hydrocarbyl alcohol, a hydrocarbyl amine, a silicon-based compound, and combinations thereof.

[0100] 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, and arylene, groups.

[0101] 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.

[0102] Preferably, the hydrophilic moiety is a moiety selected from the group consisting of selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, 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.

[0103] Preferably, the silane is functionalized with an alcohol or an amine, and combinations thereof.

[0104] Preferably, the hydrophobic alcohol is selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl-1-octanol, 2-octyl-1-dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1- hexadecanol, 2-hexadecanol, behenyl alcohol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4- methyl-1-pentanol, and mixtures thereof. Preferably, the hydrophilic alcohol is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, methoxypolyethylene glycol, and mixtures thereof. Preferably, the hydrophilic polyol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentylglycol, trimethylol propane, N-methyldiethanolamine, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, and mixtures thereof.

[0105] Preferably, the hydrophobic amine is selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, 2- methylbutylamine, and mixtures thereof. Preferably, the hydrophilic amine is selected from the group consisting of diethanolamine, serinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, dimethylamine, and mixtures thereof.

[0106] Preferably, the hydrophobic polyol is selected from the group consisting of 1,6- hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, poly(tetramethylene ether) glycol, poly(tetramethylene carbonate), poly(hexamethylene carbonate) and castor oil.

[0107] Preferably, the hydrophobic silicon-based compound is 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 hydrophilic silane is selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3- aminopropylsilanetriol, and mixtures thereof.

[0108] In one non-limiting embodiment, the hydrophobic moiety is that of a hydrocarbyl alcohol that contains from about 6 to about 36 carbon atoms and that is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional.

[0109] In one non-limiting embodiment, the hydrophilic polyol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentylglycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose and mixtures thereof.

[0110] In one non-limiting embodiment, the amines selected from the group consisting of primary, secondary, and tertiary amines and combinations thereof.

[0111] Hydrocarbyl amines are classified as primary, secondary, or tertiary, based on the number of carbon atoms attached to the amine nitrogen atom. Each class of amine may have a general formula. For example, the general formula for primary amine isand the general formula for secondary amine isthe general formula for tertiary amine iswherein R1, R2and R3stand for the same or different alkyl, alkylene, aryl, aralkyl, or arylene groups.

[0112] In one non-limiting embodiment, the hydrophobic moiety is that of a hydrocarbyl amine that contains about 6 to about 36 carbon atoms and that is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional.

[0113] In one non-limiting embodiment, the hydrocarbyl amine is a hydrophilic amine selected from the group consisting of 2-methylpentane-1,5-diamine, diethanolamine, serinol hydrochloride, 2-amino-2-ethyl-1, 3-propanediol, dimethylamine, and mixtures thereof.

[0114] In one non-limiting embodiment, the silicon-based compound is a compound having the structurewherein R stands for different alkyl, alkylene, aryl, aralkyl, arylene, hetero groups functionalized with at least one or more alcohol, amine or a combination thereof and n has the value of 1 to 10.

[0115] In one non-limiting embodiment, the silicon-based compound is a siloxane, or a silane functionalized with an alcohol, an amine or a combination thereof.

[0116] In one non-limiting embodiment, the silicon-based compound is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional compound.

[0117] 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.

[0118] 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.

[0119] In one non-limiting embodiment, the present invention provides a dispersant for a carbon nanotube comprising the reaction component (D) base comprises inorganic bases, organic bases, or combinations thereof.

[0120] In one non-limiting embodiment, the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality hasbeen partially reacted with the functionalized or unfunctionalized moiety; and (D) a base, wherein the reaction product comprises a compound having the structure:wherein R7is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

[0121] In one non-limiting embodiment, the present invention provides a dispersant for a carbon nanotube comprising a reaction product of (A) a maleated soybean oil, comprising a soybean oil with maleated functionality; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) a base, wherein the reaction product comprising one or more structure(s) selected from:wherein R7is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl-1-dodecyl, or mixtures thereof; and wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

[0122] In one non-limiting embodiment, 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; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) a base, wherein the reaction product is a polymer comprising the structure:wherein n is greater than 1; wherein R11isone or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

[0123] In one non-limiting embodiment, 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; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) a base, wherein the reaction product is a polymer comprising one or more structure(s) selected from:wherein 1 < n < 30; wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atomsand, optionally, containing heteroatoms; and wherein R11is selected from the group consisting of -CH2CH2CH2-,and mixtures thereof.

[0124] In one non-limiting embodiment, the present 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; and (b) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (B) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0125] In one non-limiting embodiment, the present 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 lactam moiety having at least one hydroxyl, thiol or amine functional group; and (c) a base; (B) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0126] In one non-limiting embodiment, the present 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 lactam moiety having at least one hydroxyl, thiol or amine functional group; (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (d) optionally, a base; (B) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0127] In one non-limiting embodiment, the present 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; and (b) a lactam moiety having at least one hydroxyl, thiol or amine functionalgroup; (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (d) optionally, a base, wherein the reaction product is a polymer; (B) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (C) a solvent.

[0128] In one non-limiting embodiment, the present application provides a method of preparing a lithium-ion or sodium-ion battery composition comprising mixing: (A) a carbon nanotube composition comprising (i) 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 lactam moiety having at least one hydroxyl, thiol or amine functional group; (ii) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube, and (iii) a solvent; (B) an electrode active material; and (C) and a binder.

[0129] In one non-limiting embodiment, the present application provides a method of preparing a lithium-ion or sodium-ion battery composition comprising mixing: (A) a carbon nanotube composition comprising (i) 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; a lactam moiety having at least one hydroxyl, thiol or amine functional group; (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (d) optionally, a base; (ii) from about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (iii) a solvent; (B) an electrode active material; and (C) a binder.

[0130] In one non-limiting embodiment, the present application provides a method of preparing a lithium-ion or sodium-ion battery composition comprising mixing: (A) a carbon nanotube composition comprising (i) 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; a lactam moiety having at least one hydroxyl, thiol or amine functional group 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; and (d) optionally, abase, wherein the reaction product is a polymer; (ii) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (iii) a solvent; (B) an electrode active material; and (C) a binder.

[0131] 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.

[0132] 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.

[0133] In some embodiments, the dispersant for a carbon nanotube or a carbon nanotube composition is a polymer having a viscosity measured at 25 ºC with a Brookfield viscometer ranging from about 100 to about 10,000 cps.

[0134] 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 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.

[0135] 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.

[0136] 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; ethylene glycols; propylene glycols; amides; pyrrolidones; hydroxyesters; sulfoxides; lactones; anilines; hydrocarbons; halogenated solvents; aromatic solvents; glycol esters and combinations thereof.

[0137] 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.

[0138] In some embodiments, the present invention discloses a lithium or sodium-ion battery comprising an anode in electrical communication with a cathode, wherein the anode or cathode comprises a carbon nanotube composition in the form of a suspension or slurry used as a conductive agent in the formulation of the electrode.

[0139] 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.

[0140] 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

[0141] Example A1: Grafting of maleic anhydride onto soybean oil

[0142] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 600 g of soybean oil and 204 g (3 mole equivalents based on soybean oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 6-8 hours. Completion of the reaction was indicated by NMR, and LC indicated <0.5% of residual maleic anhydride.

[0143] Example A2: Grafting of maleic anhydride onto palm oil

[0144] 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 15minutes, 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%.

[0145] Example A3: Grafting of maleic anhydride onto canola oil

[0146] 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%.

[0147] Example A4: Grafting of maleic anhydride onto sunflower oil

[0148] 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%.

[0149] Example A5: Grafting of maleic anhydride onto castor oil

[0150] 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%.

[0151] Example A6: Grafting of maleic anhydride onto chickpea oil

[0152] 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 °Cfor 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%.

[0153] Example A7: Grafting of maleic anhydride onto clary sage oil

[0154] 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%.

[0155] Example B1: Sodium salt of maleated soybean oil from aqueous sodium hydroxide

[0156] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of maleated soybean oil (MSBO) from Example A1 was heated to 90 °C, and a mixture of 20.20 g (3 mole equivalents based on soybean oil) of 50% aqueous sodium hydroxide and 70 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.

[0157] Example B2: Sodium salt of maleated soybean oil (MSBO) from sodium carbonate

[0158] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 was heated to 90 °C, and 27.86 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%.

[0159] Example B3: Sodium salt of MSBO from aqueous sodium hydroxide

[0160] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of MSBO from Example A1 was heated to 90 °C, and a mixture of 9.04 g (2 mole equivalents based on soybean oil) of 50% aqueous sodium hydroxide and 80 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.

[0161] Example C1: Grafting of 1-(2-hydroxyethyl)-2-pyrrolidone (HEP) onto maleated soybean oil (MSBO)

[0162] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 and either 0.5, 1, 1.5, 2, 2.5 or 3 mole equivalents, relative to MSBO, of 1-(2-hydroxyethyl)-2-pyrrolidone (HEP) were combined, heated to 120 °C and held at 120 °C for 6 hours. The amber, viscous product was characterized by NMR and IR, and GC indicated <5% of residual HEP. Yield was >96%.

[0163] Example C2: Grafting of 1-(2-aminoethyl)-2-pyrrolidone onto maleated soybean oil (MSBO)

[0164] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 and 10.0 g (1 mole equivalent, relative to MSBO) of 1-(2-aminoethyl)-2-pyrrolidone are combined, heated to 80 °C and held at 80 °C for 6 hours.

[0165] Example D1: Sodium salt of maleated soybean oil (MSBO) reacted with HEP

[0166] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of the product from Example C1 was heated to 85 °C. Water and 50% aqueous sodium hydroxide were added over 60 minutes to create a final solution that was 50 weight % solids, and the mixture was held at 85 °C for 4 hours. The amount of sodium hydroxide added was sufficient to convert each carboxylic acid group generated by hydrolysis of anhydride or reaction of anhydride with HEP into the corresponding sodium carboxylate salt. The amber liquid product was characterized by NMR and IR. Yield of MSBO-HEP adduct sodium salt was >98%.

[0167] Example D2: Lithium salt of maleated soybean oil (MSBO) reacted with HEP

[0168] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 152.1 g of MSBO made according to Example A1 and 41.8g (2.5 mole equivalents relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The amber, viscous product was cooled to 80 °C, and 9.31 g (3 mole equivalents relative to MSBO) of lithium hydroxide dissolved in 204 g of water was added over 1 hour to create a final solution that was 50 weight % solids. The mixture was heated to 85 °C and held at 85 °C for 2 hours. The amber product was characterized by NMR and IR. Yield was >96%.

[0169] Example D3: Sodium salt of maleated soybean oil (MSBO) reacted with 1-(2- aminoethyl)-2-pyrrolidone

[0170] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of the product from Example C2 is heated to 85 °C. Water and 50% aqueous sodium hydroxide are added over 60 minutes to create a final solution that is 50 weight % solids, and the mixture is held at 85 °C for 4 hours. The amount of sodium hydroxide added is sufficient to convert each carboxylic acid group generated by hydrolysis of anhydride or reaction of anhydride with 1-(2-aminoethyl)-2-pyrrolidone into the corresponding sodium carboxylate salt.

[0171] Example E1: Maleated soybean oil (MSBO) reacted with HEP and 2-octyl-1- dodecanol and crosslinked with glycerol

[0172] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 211 g of MSBO made according to Example A1 and 9.69 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was adjusted to 85 °C, and 72.8 g (1.3 mole equivalents) of 2-octyl-1-dodecanol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (17.3 g, 1.0 mole equivalent) 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%.

[0173] Example E2: Maleated soybean oil (MSBO) reacted with HEP and 2-ethyl-1- hexanol and crosslinked with glycerol

[0174] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of MSBO made according to Example A1 and 9.10 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 29.8 g (1.3 mole equivalents) of 2-ethyl-1-hexanol was added, and the mixture was held at 85 °C for 6 hours. The mixture was heated to 90 °C, 16.2 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.

[0175] Example E3: Maleated soybean oil (MSBO) reacted with HEP and benzyl alcohol and crosslinked with glycerol

[0176] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 167 g of MSBO made according to Example A1 and 11.0 g (0.6 mole equivalentrelative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, 20.0 g (1.3 mole equivalents) of benzyl alcohol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (13.1 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.

[0177] Example E4: Maleated soybean oil (MSBO) reacted with HEP and 1- naphthalenemethanol and crosslinked with glycerol

[0178] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 167 g of MSBO made according to Example A1 and 11.0 g (0.6 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 29.2 g (1.3 mole equivalents) of 1-naphthalenemethanol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (13.1 g, 1.0 mole equivalent) 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%.

[0179] Example E5: Maleated soybean oil (MSBO) reacted with HEP and lauryl alcohol and crosslinked with glycerol

[0180] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 161 g of MSBO made according to Example A1 and 7.34 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 34.4 g (1.3 mole equivalents) of lauryl alcohol was added, and the mixture was held at 85 °C for 6 hours. The mixture was heated to 90 °C, 13.1 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.

[0181] Example E6: Maleated soybean oil (MSBO) reacted with HEP and behenyl alcohol and crosslinked with glycerol

[0182] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 151 g of MSBO made according to Example A1 and 6.87 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. Themixture was cooled to 85 °C, and 59.4 g (1.3 mole equivalents) of behenyl alcohol was added, and the mixture was held at 85 °C for 6 hours. The mixture was heated to 90 °C, 12.24 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.

[0183] Example E7: Maleated soybean oil (MSBO) reacted with 1-(2-aminoethyl)-2- pyrrolidone and 2-octyl-1-dodecanol and crosslinked with glycerol

[0184] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 211 g of MSBO made according to Example A1 and 9.69 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was adjusted to 85 °C, and 72.8 g (1.3 mole equivalents) of 2-octyl-1-dodecanol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (17.3 g, 1.0 mole equivalent) 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%.

[0185] Example 1: Preparation of solvent-based CNT dispersions

[0186] 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 mixer 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.

[0187] Example 2: Analysis of solvent-based CNT dispersions

[0188] Solvent-based CNT dispersions, prepared according to Example 1 using different proportions of the dispersant of Example C1 and ethyl cellulose (Aqualon™ EC-N4, Ashland), were analyzed for particle size distribution and resistivity. As can be seen from the results in Table 1, the dispersant of Example C1 improves the particle size distribution and resistivity of the CNT dispersion, relative to ethyl cellulose.Table 1. Properties of CNT dispersions using the dispersant of Example C1

[0189] Example 3: Preparation of water-based CNT dispersions

[0190] Dispersant (0.25 g) was fully dissolved in 49.5 g of distilled water at a temperature of 5-35 ℃ and an overhead mixer speed of 200-1000 rpm for about 1-8 hours, until no particle was observable by the eye. Carbon nanotubes (JiangSu Cnano, 0.25 g) were added to the aqueous mixture, and the mixture in a closed container was shaken by hand for 30 seconds and placed the container in a sonicating bath for 15 minutes. The container was transferred to an ultrasonic mixer, utilizing a cool water bath, and sonicated for about 2-4 hours. The container was removed from the ultrasonic mixer and cooled.

[0191] Example 4: Analysis of water-based CNT dispersions

[0192] Water-based CNT dispersions, prepared according to Example 3 using different proportions of the dispersant of Example B1 and carboxymethyl cellulose CMC (Ambergum™ 1221, Ashland), were analyzed for particle size distribution and resistivity. As can be seen from the results in Table 2, the dispersant of Example B1 improves the particle size distribution and resistivity of the CNT dispersion, relative to carboxymethyl cellulose. Table 2. Properties of CNT dispersions using the dispersant of Example D1

[0193] While the compositions and methods of the disclosed and / or claimed inventive concept(s) have been described in terms of particular aspects, it will be apparent to those of ordinary skill in the art that variations may be applied to the compositions and / or methods and in the steps or in the sequence of steps of the method described herein without departing from theconcept, spirit and scope of the disclosed and / or claimed inventive concept(s). All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the disclosed and / or claimed inventive concept(s).

Claims

We claim:

1. A 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 lactam moiety having at least one hydroxyl, thiol or amine functional group.

2. The dispersant for a carbon nanotube 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 for a carbon nanotube according to claim 1, wherein the maleated natural oil is a maleated soybean oil.

4. The dispersant for a carbon nanotube according to claim 1, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup;Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

5. The dispersant for a carbon nanotube according to claim 4, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:,and combinations thereof, wherein Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkylgroups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

6. The dispersant for a carbon nanotube according to claim 5, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.

7. The dispersant for a carbon nanotube according to claim 6, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure:

8. The dispersant for a carbon nanotube according to claim 1 comprising a reaction product of (A) a maleated soybean oil; and (B) 1-(2-hydroxyethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)- 2-pyrrolidone moieties.

9. The dispersant for a carbon nanotube according to claim 8, comprising one or more structure(s) selected from:

10. The dispersant for a carbon nanotube according to claim 6, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-aminoethyl)-2-pyrrolidone, having the structure:

11. The dispersant for a carbon nanotube according to claim 1 comprising a reaction product of (A) a maleated soybean oil; and (B) 1-(2-aminoethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)-2- pyrrolidone moieties.

12. The dispersant for a carbon nanotube according to claim 11, comprising one or more structure(s) selected from:wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms.

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

14. The carbon nanotube composition according to claim 13, wherein the carbon nanotube is mixed at a weight ratio of 1:0.001 to 1:10 with the dispersant.

15. The carbon nanotube composition according to claim 13, 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 multi-walled carbon nanotube, a carbon nanohorn, a carbon nanofiber, short nanotubes, carbon particles nanotubes, and combinations thereof.

16. The carbon nanotube composition according to claim 13, wherein the solvent is selected from the group consisting of at least one aqueous solvent; alcohols; ketones; ethylene glycols; propylene glycols; amides; pyrrolidones; hydroxyesters; sulfoxides; lactones; anilines; hydrocarbons; halogenated solvents; aromatic solvents; glycol esters and combinations thereof.

17. The carbon nanotube composition according to claim 13, wherein the solvent is selected from the group consisting of water, methanol, ethanol, isopropyl alcohol, propyl alcohol, butanol, terpineol, acetone, methyl ethyl ketone, ethyl isobutyl ketone, methyl isobutyl ketone, ethylene glycol, ethylene glycol methyl ether, ethylene glycol mono-n-propyl ether, propylene glycol, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol butyl ether, propylene glycol propyl ether, dimethylformamide, 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.

18. A lithium-ion or sodium-ion battery comprising the carbon nanotube composition of claim 13.

19. A lithium-ion or sodium-ion battery composition comprising the carbon nanotube composition of claim 13.

20. A method of preparing the lithium-ion or sodium-ion battery composition of claim 19 comprising mixing (a) the carbon nanotube composition of claim 13; (b) an electrode active material, and (c) a binder.

21. A method of preparing the carbon nanotube composition of claim 13, wherein dispersion of the carbon nanotube in the solvent is accomplished using an apparatus selected fromthe group consisting of an ultrasonicator, a homogenator, a spiral mixer, a planetary mixer, a disperser, a ball miller and a blending mixer.

22. 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 lactam moiety having at least one hydroxyl, thiol or amine functional group; and(C) a base.

23. The dispersant for a carbon nanotube according to claim 22, 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.

24. The dispersant for a carbon nanotube according to claim 22, wherein the maleated natural oil is a maleated soybean oil.

25. The dispersant for a carbon nanotube according to claim 22, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein:Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

26. The dispersant for a carbon nanotube according to claim 25, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andX is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

27. The dispersant for a carbon nanotube according to claim 26, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.

28. The dispersant for a carbon nanotube according to claim 27, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure:

29. The dispersant for a carbon nanotube according to claim 22, wherein the base (C) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

30. The dispersant for a carbon nanotube according to claim 29, 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.

31. The dispersant for a carbon nanotube according to claim 29, 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.

32. The dispersant for a carbon nanotube according to claim 30, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

33. The dispersant for a carbon nanotube according to claim 30, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

34. The dispersant for a carbon nanotube according to claim 30, 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.

35. The dispersant for a carbon nanotube according to claim 29, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.

36. The dispersant for a carbon nanotube according to claim 22 comprising a reaction product of (A) a maleated soybean oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium, wherein the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three 1-(2- hydroxyethyl)-2-pyrrolidone moieties.

37. The dispersant for a carbon nanotube according to claim 36, comprising one or more structure(s) selected from:

38. A carbon nanotube composition comprising(a) about 0.01 wt. % to about 10.0 wt. % of the dispersant according to claim 22; (b) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (c) a solvent.

39. The carbon nanotube composition according to claim 38, wherein the carbon nanotube is mixed at a weight ratio of 1:0.001 to 1:10 with the dispersant.

40. The carbon nanotube composition according to claim 38, 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 multi-walled carbon nanotube, a carbon nanohorn, a carbon nanofiber, short nanotubes, carbon particles nanotubes, and combinations thereof.

41. The carbon nanotube composition according to claim 38, wherein the solvent is selected from the group consisting of at least one aqueous solvent; alcohols; ketones; ethylene glycols; propylene glycols; amides; pyrrolidones; hydroxyesters; sulfoxides; lactones; anilines; hydrocarbons; halogenated solvents; aromatic solvents; glycol esters and combinations thereof.

42. The carbon nanotube composition according to claim 38, wherein the solvent is selected from the group consisting of water, methanol, ethanol, isopropyl alcohol, propyl alcohol, butanol, terpineol, acetone, methyl ethyl ketone, ethyl isobutyl ketone, methyl isobutyl ketone, ethylene glycol, ethylene glycol methyl ether, ethylene glycol mono-n-propyl ether, propylene glycol, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol butyl ether, propylene glycol propyl ether, dimethylformamide, 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.

43. A lithium-ion or sodium-ion battery comprising the carbon nanotube composition of claim 38.

44. A lithium-ion or sodium-ion battery composition comprising the carbon nanotube composition of claim 38.

45. A method of preparing the lithium-ion or sodium-ion battery composition of claim 44 comprising mixing (a) the carbon nanotube composition of claim 38, (b) an electrode active material, and (c) a binder.

46. 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 lactam moiety having at least one hydroxyl, thiol or amine functional group;(C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and,(D) optionally, a base.

47. The dispersant for a carbon nanotube according to claim 46, wherein the maleated natural oil (A) is selected from the group consisting of maleated avocado oils, maleated coconut oils, maleated com 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.

48. The dispersant for a carbon nanotube according to claim 46, wherein the maleated natural oil is a maleated soybean oil.

49. The dispersant for a carbon nanotube according to claim 46, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between thegroup and thegroup; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms; and, R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

50. The dispersant for a carbon nanotube according to claim 49, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of: ,and combinations thereof, whereinQ is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

51. The dispersant for a carbon nanotube according to claim 50, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.

52. The dispersant for a carbon nanotube according to claim 51, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure:

53. The dispersant for a carbon nanotube according to claim 46, wherein the hydrophobic moiety (C) is a moiety selected from those of the group consisting of unsubstituted and 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 additional heteroatoms; unsubstituted and substituted polyols, with or without additional heteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.

54. The dispersant for a carbon nanotube according to claim 46, wherein the hydrophilic moiety (C) is a moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain additional heteroatoms; unsubstituted and substituted polyols, wherein the unsubstituted and 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.

55. The dispersant for a carbon nanotube according to claim 54, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.

56. The dispersant for a carbon nanotube according to claim 53, 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, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4- methyl-1-pentanol, behenyl alcohol, 1-naphthalenemethanol, benzyl alcohol and mixtures thereof.

57. The dispersant for a carbon nanotube according to claim 54, wherein the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.

58. The dispersant for a carbon nanotube according to claim 54, wherein the hydrophilic moiety is that of a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, glycerol, hexylene glycol, sorbitol, neopentylglycol, erythritol, mannitol,xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof.

59. The dispersant for a carbon nanotube according to claim 53, 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, 2- methylbutylamine, and mixtures thereof.

60. The dispersant for a carbon nanotube according to claim 54, wherein the hydrophilic moiety is that of an amine selected from the group consisting of diethanolamine, serinol, 2-amino-2-ethyl-1,3-propanediol, dimethylamine, 2-methylbutylamine, 3-amino-1- propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof.

61. The dispersant for a carbon nanotube according to claim 53, 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.

62. The dispersant for a carbon nanotube comprising a reaction product according to claim 54, wherein the silane is a hydrophilic compound selected from the group consisting of 3- aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

63. The dispersant for a carbon nanotube comprising a reaction product according to claim 46, wherein the base (D) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

64. The dispersant for a carbon nanotube according to claim 63, 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.

65. The dispersant for a carbon nanotube according to claim 63, 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.

66. The dispersant for a carbon nanotube according to claim 64, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

67. The dispersant for a carbon nanotube according to claim 64, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

68. The dispersant for a carbon nanotube according to claim 64, 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.

69. The dispersant for a carbon nanotube comprising a reaction product according to claim 46 that is a reaction product of (A) a maleated soybean oil; (B) 1-(2-hydroxyethyl)-2- pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base.

70. The dispersant for a carbon nanotube comprising a reaction product according to claim 69, wherein the reaction product has the structure:wherein R7is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

71. The dispersant for a carbon nanotube according to claim 70, comprising one or more structure(s) selected from: ,wherein R7is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl-1-dodecyl, or mixtures thereof; and wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

72. The dispersant for a carbon nanotube comprising a reaction product according to claim 46, wherein the reaction product is a polymer having the structure:wherein n is greater than 1; wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

73. The dispersant for a carbon nanotube according to claim 72, wherein the polymer comprises one or more structure(s) selected from:wherein 1 < n < 30; wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms.

74. The dispersant for a carbon nanotube according to claim 73, wherein R11is -CH2CH2CH2-,or a mixture thereof.

75. A carbon nanotube composition comprising (a) about 0.01 wt. % to about 10.0 wt. % of dispersant according to claim 46; (b) about 0.01 wt. % to about 10.0 wt.% of carbon nanotube; and (c) a solvent.

76. The carbon nanotube composition according to claim 75, wherein the carbon nanotube is mixed at a weight ratio of 1:0.001 to 1:10 with the dispersant.

77. The carbon nanotube composition according to claim 75, 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 multi-walled carbon nanotube, a carbon nanohorn, a carbon nanofiber, short nanotubes, carbon particles nanotubes, and combinations thereof.

78. The carbon nanotube composition according to claim 75, wherein the solvent is selected from the group consisting of at least one aqueous solvent; alcohols; ketones; ethylene glycols; propylene glycols; amides; pyrrolidones; hydroxyesters; sulfoxides; lactones; anilines; hydrocarbons; halogenated solvents; aromatic solvents; glycol esters and combinations thereof.

79. The carbon nanotube composition according to claim 75, wherein the solvent is selected from the group consisting of water, methanol, ethanol, isopropyl alcohol, propyl alcohol, butanol, terpineol, acetone, methyl ethyl ketone, ethyl isobutyl ketone, methyl isobutyl ketone, ethylene glycol, ethylene glycol methyl ether, ethylene glycol mono-n-propyl ether, propylene glycol, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol butyl ether, propylene glycol propyl ether, dimethylformamide, 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.

80. A lithium-ion or sodium-ion battery comprising the carbon nanotube composition of claim 75.

81. A lithium-ion or sodium-ion battery composition comprising the carbon nanotube composition of claim 75.

82. A method of preparing a carbon nanotube dispersion for use in a lithium-ion or sodium-ion battery composition of claim 81 comprising mixing (a) the carbon nanotube composition of claim 75, (b) an electrode active material, and (c) a binder.

83. A method of preparing the carbon nanotube composition of claim 75, wherein dispersion of the carbon nanotube in the 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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