Hydrophobically and hydrophilically modified maleated natural oils and compositions thereof

Abstract

The present invention provides a composition comprising the reaction product of (a) a maleated natural oil comprising a natural oil having a maleic acid functionality, and (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and a combination thereof, with the proviso that the hydrophilic moiety is not a glycerol moiety. In another aspect of the present invention, the present invention provides a composition comprising the reaction product of (a) a maleated natural oil comprising a natural oil having a maleic acid functionality, and (b) a functional or non-functional hydrophobic moiety, and (c) a glycerol moiety. In yet another aspect, the present application provides a composition comprising the reaction product of (a) a maleated natural oil comprising a natural oil having a maleic acid functionality, and (b) two functional or non-functional hydrophilic moieties. The composition may further comprise a functional system active ingredient. The modified maleated natural oil is useful in a wide variety of compositions and applications. In yet another aspect of the present invention, the present invention provides a compound represented by structure (I): [Formula 1] JPEG2024533620000064.jpg183130

Description

[Technical field]

[0001] The present application provides compositions comprising modified maleated natural oils. The modified maleated natural oils do not exhibit many of the limiting properties of maleated natural oils. The modified maleated natural oils are useful in a wide variety of compositions and applications. [Background technology]

[0002] Modified natural oils can be non-dispersible in water or alcohol.As a result, these 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, electronic, household, industrial and institutional (HI&I) compositions, inks, films, metalworking fluids, oilfield chemicals, plastics and plasticizers, textiles, industrial products, biocides, pharmaceutical / nutritional, and agrochemical compositions.

[0003] Natural oils, such as soybean oil and linseed oil, are among the most promising feedstocks for the synthesis of renewable compounds, including polymers, plastics, and plasticizers. These natural materials are inexpensive, highly abundant, derived from reliable and sustainable resources, and have high potential for improvement. Natural oils are generally mixtures of various triglycerides, which are esters of fatty acids with glycerol, and have various degrees of unsaturation (i.e., double bonds). The oils can be characterized by their hydroxyl value and fatty acid composition. Both natural fatty acids and natural oils require chemical modification to make them sufficiently reactive to allow structural changes and polymerization to occur, due to the relative inertness of the olefinic functional groups. The unsaturated double bonds in these compounds have been converted to epoxide and succinic anhydride functional groups, allowing the introduction of many hydroxyl-containing species into natural oils.

[0004] Maleated natural oils are natural oils that have been chemically functionalized by the chemical addition of epoxide (oxirane) and succinic anhydride functional groups. Examples include epoxidized and maleated soybean oil and linseed oil, and unsaturated natural oils lend themselves to these chemical functionalizations.

[0005] US Patent No. 9,809,538 B2 describes modified natural compounds synthesized from epoxidized natural fatty acids, maleated natural fatty acids, epoxidized natural oils, or maleated natural oils, with hydroxyl-containing lactam compounds to form, for example, adhesives or beverage compositions.

[0006] A discussion of the reaction scheme for the maleation reaction in vegetable oils is given in the paper "Maleated soybean oil and its multifunctional properties" by Gripp, Anna A. and Steinberg, David C., presented at the Cosmetics Exhibition & Conference Conference Proceedings, Barcelona, ​​March 22-24, 1994.

[0007] The reaction scheme for the maleation reaction in vegetable oils is discussed in the paper "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).

[0008] A discussion of the general reaction between maleic anhydride and unsaturated vegetable oils is given in the handbook of maleic anhydride based materials- syntheses, properties and applications by Osama M. Musa, Chapter 3, page 166, Springer International Publishing Switzerland 2016.

[0009] US Pat. No. 2,754,306 A describes the reaction of soybean oil, a maleic anhydride base, and isooctyl alcohol to provide an improved plasticizer for nitrocellulose compositions.

[0010] PCT Application Nos. 2019113068A1 and 2005071050A1 describe technology relating to metalworking fluids containing maleated soybean oil derivatives.

[0011] A discussion of maleic anhydride polymerization and modified vegetable oils with polyols is given in the article "Polymerization of Maleic Anhydride-Modified Plant Oils with Polyols" by Tarik Eren, Selim H. Kusefoglu and Richard Wool, published in the Journal of Applied Polymer Science (Barcelona, ​​Vol. 90, No. 1, pp. 197-202, 2003).

[0012] EP 2754306A describes an adhesive comprising a polycondensate and a dienophile-modified fatty acid as crosslinker.

[0013] US Application No. 20180070584A1 describes adjuvant compositions that include maleated natural oil derivatives in pesticide formulations and are applied to target substrates to kill, inhibit, or repel pests.

[0014] PCT Application No. 2005071050A1 describes metalworking fluids comprising oil-in-water emulsions derived from the reaction product of maleic anhydride and triglyceride oils from plants or terrestrial animals, further reacted with water, Group IA and IIA metals, ammonium hydroxide, various amines, alkanolamines, polyols, alkoxylated alkanolamines, polyalkylene oxides, or polyamines, or mixtures.

[0015] Despite the renewable, biodegradable, sustainable, and beneficial functions offered by natural fatty acids, natural oils, and their maleated counterparts, they exhibit properties that may limit their applications. For example, maleated soybean oil is not soluble or dispersible in water or alcohol. As a result, these oils tend to leach or phase separate from formulated compositions. This characteristic makes their formulation more difficult and often requires additional ingredients to facilitate solutions, emulsions, or dispersions. Natural oils and maleated natural oils may not provide the desired properties required for end use, such as solubilization ability, glass transition, flexibility, shine, and / or plasticization. As a result, performance (including but not limited to stability, resistance to phase separation, absorption, cleansing, solubility, dyeability, lubrication, film formation, uniformity of diffusion, comedogenic tendency, ease of removal) and aesthetic qualities (skin feel, greasiness, glossy appearance, etc.) may be less than desired. Finally, such natural oils, although important renewable materials, are not always the formulator's first choice, and in fact are often not even considered at all.

[0016] Mineral oils and vegetable oils are often used as ingredients in personal care compositions. Therefore, there is a need for renewable, natural, and biodegradable materials with various controllable chemical, physical, and / or mechanical properties that minimize or eliminate the limitations found in natural oils and maleated natural oils. Most personal care compositions contain two or more inactive ingredients to help deliver active ingredients and provide desired skin care properties. Some continue to have toxic products or other unwanted side effects in skin care. In addition, each time a new active ingredient is brought to the market, it requires the development of a unique composition to bring that active ingredient to the field. Therefore, there is a need to develop new functional maleated natural oils for use in personal care inactive ingredients that are non-toxic and originate from or are made from renewable resources. Summary of the Invention

[0017] The present invention provides a composition comprising: (a) a reaction product of a maleated natural oil, including a natural oil having a maleic acid functionality, and (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, with the proviso that the hydrophilic moiety is not a glycerol moiety.

[0018] In another aspect of the invention, the invention provides a composition comprising the reaction product of (a) a maleated natural oil, which comprises a natural oil having a maleic acid functionality; (b) a functional or non-functional hydrophobic moiety; and (c) a glycerol moiety.

[0019] In yet another aspect, the present application provides a composition comprising: (A) a reaction product of (a) a maleated natural oil, including a natural oil having maleic acid functionality, and (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof; and (B) (a) a functional system active ingredient.

[0020] In yet another aspect, the present application provides a method for producing a method for treating a cancer cell comprising: (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) two functional or non-functional hydrophilic moieties; The present invention provides a composition comprising the reaction product of:

[0021] In yet another aspect, the present application provides a method for producing a method for treating a cancer cell comprising: (A) (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) two functional or non-functional hydrophilic moieties; and the reaction product of (B) Sensory system active ingredients and A composition comprising:

[0022] In yet another aspect, the present invention provides a compound represented by the structure set forth below: [ka]

[0023] The modified maleated natural oils are useful in a wide variety of compositions and applications. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0024] The present application provides compositions comprising modified maleated natural oils that do not exhibit many of the limiting properties of maleated natural oils. The modified maleated natural oils are useful in a wide variety of compositions and applications.

[0025] Natural oils are derived from abundant, inexpensive, and sustainable resources. Natural oils are useful for synthesizing renewable compounds, such as polymers, plastics, and plasticizers, which are useful in a variety of compositions. The difficulty in utilizing natural oils is that they are mixtures of triglycerides containing groups of various degrees of unsaturation, which are relatively inert. To increase the reactivity of these natural oils, these unsaturated groups are generally chemically modified to increase their reactivity. For example, these unsaturated groups can react with maleic esters to provide epoxide and succinic anhydride functional groups. Despite these chemical modifications, maleated natural oils can still exhibit limited properties, such as insolubility or indispersibility in water and alcohol. Thus, there is a need for further modified maleated natural oils that do not exhibit the limited properties of maleated natural oils.

[0026] Unless otherwise defined herein, terms used in connection with the inventive concepts disclosed and / or claimed herein shall have the meanings commonly understood by those of ordinary skill in the art. Further, unless the context requires otherwise, singular terms shall include the plural and plural terms shall include the singular.

[0027] The singular forms "a," "an," and "the" include the plural unless the context clearly indicates otherwise or the contrary is clearly implied by the stated context. The terms "Comprising" and "Comprises of" include more restrictive claims such as "Consisting essentially of" and "Consisting of."

[0028] For purposes of the following detailed description, in any operating examples, or unless otherwise indicated, for example, numbers expressing quantities of ingredients used in the specification and claims are to be understood in all instances as being modified by the term "about." The numerical parameters set forth in the specification and appended claims are approximations that may vary depending upon the desired properties obtained in the practice of the present invention.

[0029] All percentages, parts, proportions, and ratios used herein are by weight of the total composition unless otherwise specified. All such weights relating 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.

[0030] All publications, articles, documents, patents, patent publications, and other references cited herein are hereby incorporated in their entirety for all purposes to the extent consistent with the disclosure of this specification.

[0031] Use of the term "at least one" is understood to include one, and any amount greater 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 to 100 or 1000 or more, depending on the term with which it is accompanied. Additionally, the amount of 100 / 1000 should not be considered limiting, as lower or higher limits may also yield satisfactory results.

[0032] 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.

[0033] As used herein, the words "comprising" (and any form including "comprise" and "comprises," etc.), "having" (and any form including "have" and "has," etc.), "including" (and any form including "includes" and "include," etc.), or "containing" (and any form including "contains" and "contain," etc.) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.

[0034] The term "independently selected from the group consisting of" means that when a group occurs more than once in a structure, each occurrence of the group may be independently selected.

[0035] The term "polymer" refers to a compound containing repeating structural units (monomers) linked by covalent chemical bonds. Polymers may be further derivatized, crosslinked, grafted, or endcapped. Non-limiting examples of polymers include copolymers, terpolymers, tetrapolymers, quaternary polymers, and homologs. The term "copolymer" refers essentially to a polymer consisting of two or more different types of monomers polymerized to obtain the copolymer.

[0036] The term "reaction product" refers to a substance produced from a chemical reaction of one or more reactants.

[0037] The term "natural oil" refers to compounds containing triglycerides and may contain varying levels of fatty acids, monoglycerides, diglycerides, and triglycerides, and refers to oils derived from vegetable or animal sources. Natural oils also include fatty acid glyceryl esters synthesized by reacting glycerol with 1, 2, or 3 molar equivalents of a fatty acid or mixture of fatty acids. These compounds can be mono-, di-, or triglycerides of a single fatty acid or mixture of fatty acids.

[0038] The term "maleated natural oil" as used herein refers to a natural oil having at least one or more maleated functionality. Thus, the terms "maleination" or "maleated" as used hereinafter should be understood to mean "functionalization" insofar as the use of functionalizing agents other than maleic anhydride is anticipated for use in the process of the present invention.

[0039] As used herein, the term "moiety" or "moieties" refers to a portion or functional group of a molecule.

[0040] The term "sensory system active ingredient" refers to any ingredient that provides pharmacological activity or other direct effect on the diagnosis, cure, mitigation, treatment, or prevention of disease, or affects the structure or any function of the human or animal body. The sensory system active ingredient may be present in a personal care product or a household care product. When the sensory system active ingredient is present in a personal care product that includes at least one active personal care ingredient, the personal care active ingredient may include, but is not limited to, analgesics, anesthetics, antibiotic preparations, antifungals, preservatives, antidandruff agents, antibacterial agents, vitamins, hormones, antidiarrheal drugs, corticosteroids, anti-inflammatory drugs, vasodilators, keratolytic agents, dry eye compositions, wound care agents, infection prevention agents, and solvents, diluents, adjuvants, and other ingredients such as water, mineral oil, preservatives, surfactants, propellants, fragrances, essential oils, and viscosity modifiers.

[0041] The term "functionalized" with respect to any moiety refers to the presence of one or more functional groups on that moiety. A variety of functional groups can be introduced to a moiety by one or more functionalization reactions known to those skilled in the art. Non-limiting examples of functionalization reactions include alkylation, epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Canizzaro reaction, Mannich reaction, Claisen condensation, Suzuki coupling, and the like. In one non-limiting embodiment, the term "functionalized" with respect to any moiety refers to the presence of one or more functional groups on that moiety selected from the group consisting of alkyl, alkenyl, hydroxyl, carboxyl, halogen, alkoxy, amino, imino, and combinations thereof.

[0042] As used herein, the term "hydrophilic" means that a compound has an affinity for water, while the term "hydrophobic" means that a compound does not have an affinity for water.

[0043] The terms are relative, and the hydrophilic portion may or may not be completely water soluble, even if it has a higher affinity for water than the hydrophobic portion. Similarly, the hydrophobic portion has a lower affinity for water than the hydrophilic portion, but the hydrophobic portion is not necessarily water repellent. While the hydrophilic portion has an affinity for water and other polar solvents, the hydrophobic portion tends to have an affinity for oils, fats, and other non-polar solvents.

[0044] The term "unreacted maleic functionality" refers to a composition comprising the reaction product of a maleated natural oil in which the maleic functionality component remains completely unreacted and unchanged in nature.

[0045] The term "hydrocarbyl" includes straight and branched chain alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl groups, and combinations thereof, along with optional heteroatoms. The hydrocarbyl groups can be monovalent, divalent, or polyvalent and have carbon chains containing at least two carbon atoms, preferably from 2 to 100 carbon atoms.

[0046] The term "alkyl" refers to a functional or non-functional, monovalent, straight-chain, branched-chain, or cyclic C-C alkyl group, optionally having one or more heteroatoms. 60 In one non-limiting embodiment, alkyl is a C-C 45 In another non-limiting embodiment, alkyl is a C-C 30 It is a 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, isonorbornyl, 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 resulting from a combination of linear, branched, and / or cyclic structures.

[0047] The term "aryl" refers to a functional or non-functional, monovalent, aromatic hydrocarbyl group, optionally having one or more heteroatoms. The definition of aryl includes carbocyclic and heterocyclic aromatic groups. Non-limiting examples of aryl groups include phenyl, naphthyl, indenyl, indanyl, azulenyl, fluorenyl, anthracenyl, furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 2-pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl, 1,3,4-thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,3,5-trithianyl, indolizinyl, isopropyl, phenyl ... 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.

[0048] The term "aralkyl" refers to an alkyl group containing one or more aryl substituents, where "aryl" and "alkyl" are 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.

[0049] The term "alkylene" refers to a functional or non-functional, divalent, straight-chain, branched-chain, or cyclic C-C alkyl group, optionally with one or more heteroatoms. 40 In one non-limiting embodiment, alkylene is a C-C 30In another non-limiting embodiment, alkylene is a group of C1-C 20 Non-limiting examples of alkylene groups include: [ka]

[0050] The term "arylene" refers to a functional or non-functional, divalent, aromatic hydrocarbyl group, optionally having one or more heteroatoms. The definition of arylene includes carbocyclic and heterocyclic groups. Non-limiting examples of arylene groups include phenylene, naphthylene, pyridinylene, and the like.

[0051] The term "heteroatom" refers to oxygen, nitrogen, sulfur, silicon, phosphorus, or halogen. Heteroatoms may be present as part of one or more heteroatom-containing functional groups. Non-limiting examples of heteroatom-containing functional groups include ether, hydroxy, epoxy, carbonyl, carboxamide, carboxylic acid ester, carboxylic acid, imine, imide, amine, sulfone, sulfonamide, phosphone, and silane groups. Heteroatoms may be present as part of rings in heteroaryl and heteroarylene groups.

[0052] The structures depicted below may refer to the first, second, or third structures, or combinations thereof. The succinic anhydride group may be present in the top, middle, or bottom chain. [ka]

[0053] In one non-limiting embodiment, the hydrophobic and hydrophilic moieties are hydrocarbyl alcohols, hydrocarbyl amines, silicon-based compounds, or combinations thereof.

[0054] Hydrocarbyl alcohols are classified as primary, secondary, and tertiary alcohols based on the number of carbon atoms connected to the carbon atom bearing the hydroxyl group. Each class of alcohol may have a general formula. For example, The general formula for a primary alcohol is: [ka] The general formula for a secondary alcohol is: [ka] The general formula for a tertiary alcohol is: [ka] where R, R', and R" represent hydrogen and various alkyl, alkylene, aryl, aralkyl, arylene, and heteroatom groups.

[0055] The present invention provides a composition comprising: (a) a reaction product of a maleated natural oil, including a natural oil having maleic acid functionality, and (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, with the proviso that the hydrophilic moiety is not a glycerol moiety. Preferably, the reaction product has unreacted maleic acid functionality or a maleic acid functionality functionalized with a hydrophobic moiety, a hydrophilic moiety, or combinations thereof.

[0056] Preferably, the hydrophobic moiety is a moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols, any of the above groups with or without heteroatoms, including from about 6 to about 36 carbon atoms, unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl amines, any of the above groups with or without heteroatoms, including from about 6 to about 36 carbon atoms, silicon-based compounds, and combinations thereof.

[0057] Preferably, the hydrophilic moiety is a moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols, any of the above groups having or without heteroatoms, from about 1 to about 5 carbon atoms, unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl amines, any of the above groups having or without heteroatoms, from about 1 to about 5 carbon atoms, unsubstituted or substituted polyols, any of the above groups having or without heteroatoms, from about 2 to 36 carbon atoms, silanes, and combinations thereof.

[0058] Preferably, the silane is functionalized with an alcohol or an amine, and combinations thereof. More preferably, the hydrophobic alcohol is selected from the group consisting of heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-octyl-1-dodecyl alcohol, 2-tertradecanol, 2-hexadecanol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4-methyl-1-pentanol, and mixtures thereof. More preferably, the hydrophilic alcohol is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, methoxypolyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, L-ribose, 2-deoxy-D-galactose, and mixtures thereof.

[0059] Preferably, the hydrophobic amine is selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, dimethylamine, and mixtures thereof. Preferably, the hydrophilic amine is selected from the group consisting of 2-methylpentane-1,5-diamine, diethanolamine, diisopropanolamine, serinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, N-methyl-D-glucosamine, D-galactosamine hydrochloride, D-glucosamine hydrochloride, D-mannosamine hydrochloride, and mixtures thereof.

[0060] Preferably, the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxane, monocarbinol terminated functional polydimethylsiloxane, [bis(hydroxyethyl)amine] terminated polydimethylsiloxane, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropylmethylsiloxane, and mixtures thereof. Preferably, the silane is a hydrophilic compound selected from the group consisting of 3-aminopropyl silanetriol, N-(2-aminoethyl)-3-aminopropyl silanetriol, and mixtures thereof.

[0061] Preferably, the maleated natural oil is selected from the group consisting of maleated avocado oil, maleated palm oil, maleated corn oil, maleated cottonseed oil, maleated jojoba oil, maleated linseed oil, maleated nut oil, maleated olive oil, maleated palm oil, maleated raisin oil, maleated rapeseed oil, maleated safflower oil, maleated sesame oil, maleated soybean oil, maleated pumpkin oil, maleated sunflower oil, maleated almond oil, maleated canola oil, maleated flaxseed oil, maleated grapeseed oil, maleated palm oil, maleated palm kernel oil, maleated peanut oil, maleated walnut oil, and mixtures thereof. More preferably, the maleated natural oil is maleated soybean oil.

[0062] Preferably, the composition is selected from the group consisting of skin care compositions, oral care compositions, hair care compositions, energy compositions, construction compositions, biocidal compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, cosmetic compositions, home care compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, and disinfecting compositions.

[0063] In another aspect, the present invention provides a composition comprising the reaction product of (a) a maleated natural oil, the natural oil having maleic acid functionality, (b) a functional or non-functional hydrophobic moiety, and (c) a glycerol moiety. Preferably, the reaction product has unreacted maleic acid functionality or maleic acid functionality functionalized with a hydrophobic moiety, a hydrophilic moiety, or a combination thereof.

[0064] Preferably, the hydrophobic moiety is a moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl and aryl alcohols, any of the above groups may or may not have heteroatoms, including from about 6 to about 36 carbon atoms, unsubstituted or substituted alkyl, cycloalkyl, alkenyl and aryl amines, any of the above groups may or may not have heteroatoms, including from about 6 to about 36 carbon atoms, silicon-based compounds, and combinations thereof. Preferably, the hydrophobic moiety is an alcohol selected from the group consisting of heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-octyl-1-dodecyl alcohol, 2-tertradecanol, 2-hexadecanol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4-methyl-1-pentanol, and mixtures thereof. Preferably, the hydrophobic moiety is an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, dimethylamine, and mixtures thereof.

[0065] Preferably, the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxane, monocarbinol terminated functional polydimethylsiloxane, [bis(hydroxyethyl)amine] terminated polydimethylsiloxane, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropylmethylsiloxane, and mixtures thereof.

[0066] Preferably, the maleated natural oil is selected from the group consisting of maleated avocado oil, maleated palm oil, maleated corn oil, maleated cottonseed oil, maleated jojoba oil, maleated linseed oil, maleated nut oil, maleated olive oil, maleated palm oil, maleated raisin oil, maleated rapeseed oil, maleated safflower oil, maleated sesame oil, maleated soybean oil, maleated pumpkin oil, maleated sunflower oil, maleated almond oil, maleated canola oil, maleated flaxseed oil, maleated grapeseed oil, maleated palm oil, maleated palm kernel oil, maleated peanut oil, maleated walnut oil, and mixtures thereof. More preferably, the maleated natural oil is maleated soybean oil.

[0067] Preferably, the composition is selected from the group consisting of skin care compositions, oral care compositions, hair care compositions, energy compositions, construction compositions, biocidal compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, cosmetic compositions, home care compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, and disinfecting compositions.

[0068] A suitable composition comprises a compound selected from the group of structures represented by the structures depicted below: [ka]

[0069] Suitable compounds may be selected from the group of structures represented by the structures depicted below: [ka] In yet another aspect, the present invention provides a composition comprising: (A) a reaction product of (a) a maleated natural oil, comprising a natural oil having a maleic acid functionality, and (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, with the proviso that the hydrophilic moiety is not a glycerol moiety; and (B) (a) a functional system active ingredient.

[0070] The preferences recited for the invention described above for "a composition comprising the reaction product of (a) a maleated natural oil, including a natural oil having a maleic acid functionality, and (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, with the proviso that the hydrophilic moiety is not a glycerol moiety" also apply to this aspect of the invention.

[0071] The composition may be selected from the group consisting of skin care compositions, oral care compositions, hair care compositions, energy compositions, construction compositions, biocidal compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, cosmetic compositions, home care compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, and disinfecting compositions.

[0072] In yet another aspect, the present invention provides a composition comprising: (A) a reaction product of (a) a maleated natural oil, which comprises a natural oil having maleic acid functionality; (b) a functional or non-functional hydrophobic moiety; and (c) a glycerol moiety; and (B) a functional system active ingredient.

[0073] The preferences recited for the present invention described above for "(A) a composition comprising (a) a reaction product of a maleated natural oil comprising a natural oil having maleic acid functionality, (b) a functional or non-functional hydrophobic moiety, (c) a glycerol moiety, and (B) a functional system active ingredient" also apply to this aspect of the invention.

[0074] The composition may be selected from the group consisting of skin care compositions, oral care compositions, hair care compositions, energy compositions, construction compositions, biocidal compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, cosmetic compositions, home care compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, and disinfecting compositions.

[0075] A suitable composition comprises a compound selected from the group of structures represented by the structures depicted below: [ka]

[0076] In yet another aspect, the present invention provides a personal care composition comprising: (A) a reaction product of (a) a maleated natural oil, comprising a natural oil having a maleic acid functionality, and (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, with the proviso that the hydrophilic moiety is not a glycerol moiety; and (B) (a) a personal care sensory system active ingredient.

[0077] The preferences recited for the invention described above for "a composition comprising the reaction product of (a) a maleated natural oil, including a natural oil having a maleic acid functionality, and (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, with the proviso that the hydrophilic moiety is not a glycerol moiety" also apply to this aspect of the invention.

[0078] The composition may be present in an amount of about 0.01% to about 10% of (A) and about 90% to about 99.99% of (B).

[0079] The personal care sensory system actives may be selected from the group consisting of color agents, hair care agents, skin care agents, and sun care agents.

[0080] In yet another aspect, the present invention provides a personal care composition comprising: (A) a reaction product of (a) a maleated natural oil, including a natural oil having a maleic acid functionality; (b) a functional or non-functional hydrophobic moiety; and (c) a glycerol moiety; and (B) a personal care functional system active ingredient.

[0081] The preferences recited for the present invention described above for "(A) a composition comprising (a) a reaction product of a maleated natural oil comprising a natural oil having maleic acid functionality, (b) a functional or non-functional hydrophobic moiety, (c) a glycerol moiety, and (B) a functional system active ingredient" also apply to this aspect of the invention.

[0082] The composition may be present in an amount of about 0.01% to about 10% of (A) and about 90% to about 99.99% of (B).

[0083] The personal care sensory system actives may be selected from the group consisting of color agents, hair care agents, skin care agents, and sun care agents.

[0084] The personal care composition may be a formulation selected from the group consisting of a spray, a lotion, a mousse, a fluid, a serum, a solution, a suspension, a perm, an emulsion, a gel, a mist, a vesicle, a dispersion, a paste, a cream, a solid stick, a shampoo, a balm, a wipe, a milk, a foam, a jelly, and a liquid.

[0085] In yet another aspect, the present invention provides a skin care composition comprising: (A) a reaction product of (a) a maleated natural oil, including a natural oil having a maleic acid functionality, and (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, with the proviso that the hydrophilic moiety is not a glycerol moiety; and (B) (a) a skin care functional system active ingredient.

[0086] The preferences recited for the present invention described above for "(A) a composition comprising (a) a reaction product of a maleated natural oil comprising a natural oil having maleic acid functionality, (b) a functional or non-functional hydrophobic moiety, (c) a glycerol moiety, and (B) a functional system active ingredient" also apply to this aspect of the invention.

[0087] The composition may be present in an amount of about 0.01% to about 10% of (A) and about 90% to about 99.99% of (B).

[0088] The skin care sensory system actives may be selected from the group consisting of color agents, hair care agents, skin care agents, and sun care agents.

[0089] In yet another aspect, the present invention provides a skin care composition comprising: (A) a reaction product of (a) a maleated natural oil, comprising a natural oil having a maleic acid functionality; (b) a functional or non-functional hydrophobic moiety; and (c) a glycerol moiety; and (B) a skin care functional system active ingredient.

[0090] The preferences recited for the present invention described above for "(A) a composition comprising (a) a reaction product of a maleated natural oil comprising a natural oil having maleic acid functionality, (b) a functional or non-functional hydrophobic moiety, (c) a glycerol moiety, and (B) a functional system active ingredient" also apply to this aspect of the invention.

[0091] The composition may be present in an amount of about 0.01% to about 10% of (A) and about 90% to about 99.99% of (B).

[0092] Preferably, the skin care sensory system active is selected from the group consisting of color agents, hair care agents, skin care agents, and sun care agents.

[0093] Preferably, the skin care sensory system active is a formulation selected from the group consisting of a spray, a lotion, a mousse, a fluid, a serum, a solution, a suspension, a perm, an emulsion, a gel, a mist, a vesicle, a dispersion, a paste, a cream, a solid stick, a shampoo, a balm, a wipe, a milk, a foam, a jelly, and a liquid.

[0094] In yet another aspect, the present application provides a method for producing a method for treating a cancer cell comprising: (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) two functional or non-functional hydrophilic moieties; The present invention provides a composition comprising the reaction product of:

[0095] In yet another aspect, the present application provides a method for producing a method for treating a cancer cell comprising: (A) (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) two functional or non-functional hydrophilic moieties; and the reaction product of (B) Sensory system active ingredients and A composition comprising:

[0096] In one non-limiting embodiment, the hydrocarbyl alcohol of the hydrophobic portion contains 2 to 36 carbon atoms and is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional, or polyfunctional.

[0097] In one non-limiting embodiment, the hydrocarbyl alcohol is selected from the group consisting of monohydric alcohols, dihydric alcohols, polyhydric alcohols, and combinations thereof.

[0098] In one non-limiting embodiment, the hydrocarbyl amine is selected from the group consisting of primary amines, secondary amines, and combinations thereof.

[0099] Hydrocarbyl amines are classified into primary, secondary, and tertiary alcohols based on the number of carbon atoms connected to the carbon atom bearing the hydroxyl group. Each class of alcohol may have a general formula. For example, The general formula for a primary amine is: [ka] The general formula for a secondary amine is: [ka] Here, R and R' represent hydrogen and various alkyl, alkylene, aryl, aralkyl, arylene, and heteroatom groups.

[0100] In one non-limiting embodiment, the hydrocarbyl amine of the hydrophobic portion contains 2 to 36 carbon atoms and is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional, or polyfunctional.

[0101] In one non-limiting embodiment, the silicon-based compound is: [ka] where R represents various alkyl, alkylene, aryl, aralkyl, arylene, hetero groups functionalized with at least one or more alcohols, amines, or combinations thereof, and n has a value from 1 to 10.

[0102] 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.

[0103] In one non-limiting embodiment, the silicon-based compound is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional, or polyfunctional compound.

[0104] In one non-limiting embodiment, the hydrocarbyl alcohol is selected from the group consisting of monohydric alcohols, dihydric alcohols, polyhydric alcohols, and combinations thereof.

[0105] In one non-limiting embodiment, the hydrocarbyl alcohol is a hydrophobic alcohol selected from the group consisting of propanol, butanol, pentanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-octyl-1-dodecyl alcohol, 2-tertradecanol, 2-hexadecanol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4-methyl-1-pentanol, and mixtures thereof.

[0106] In one non-limiting embodiment, the hydrocarbyl alcohol is methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, methoxypolyethylene glycol, polypropylene glycol, hexylene glycol, glycerol, sorbitol, octanol, methylethylpentanol, trimethylpentanol, ethylhexanol, methylheptanol, nonanol, methyloctanol, ethylheptanol, methylethylhexanol, cyclohexanol, diethylhexanol, ... The hydrophilic alcohol is selected from the group consisting of methylheptanol, decanol, methylnonanol, ethyloctanol, trimethylheptanol, undecanol, methyldecanol, ethylnonanol, dodecanol, tetradecanol, hexadecanol, octadecanol, benzyl alcohol, phenoxyethanol, neopentyl glycol, trimethylolpropane, methyldiethanolamine, erythritol, mannitol, xylitol, pentaerythritol, threitol, pentaerythritol, beta-cyclodextrin, L-ribose, 2-deoxy-D-galactose, and mixtures thereof.

[0107] In one non-limiting embodiment, the hydrocarbyl amine is a hydrophobic amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, dimethylamine, and mixtures thereof.

[0108] In one non-limiting embodiment, the hydrocarbyl amine is a hydrophilic amine selected from the group consisting of 2-methylpentane-1,5-diamine, diethanolamine, diisopropanolamine, serinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, N-methyl-D-glucosamine, D-galactosamine hydrochloride, D-glucosamine hydrochloride, D-mannosamine hydrochloride, and mixtures thereof.

[0109] 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-hydroxypolyalkyleneoxypropylmethylsiloxane, and mixtures thereof. [ka] [ka]

[0110] In one non-limiting embodiment, the silicon-based compound is a hydrophilic compound selected from the group consisting of 3-aminopropyl silanetriol, N-(2-aminoethyl)-3-aminopropyl silanetriol, and mixtures thereof. [ka]

[0111] In one non-limiting embodiment, the maleated natural oil is selected from the group consisting of maleated avocado oil, maleated palm oil, maleated corn oil, maleated cottonseed oil, maleated jojoba oil, maleated linseed oil, maleated nut oil, maleated olive oil, maleated palm oil, maleated raisin oil, maleated rapeseed oil, maleated safflower oil, maleated sesame oil, maleated soybean oil, maleated pumpkin oil, maleated sunflower oil, maleated almond oil, maleated canola oil, maleated flaxseed oil, maleated grapeseed oil, maleated palm oil, maleated palm kernel oil, maleated peanut oil, and the maleated walnut oil.

[0112] The reactions of the present application may be readily synthesized by procedures known to those skilled in the art, including, but not limited to, free radical solution polymerization, dispersion polymerization, emulsion polymerization, ionic chain polymerization, living polymerization, bulk polymerization, suspension polymerization, or precipitation polymerization. In particular, the polymerization is carried out by any of the methods disclosed and disclosed in "Principles of Polymerization" (4th Edition, 2004, Wiley by George Odian), which is incorporated herein by reference in its entirety, and "Decomposition Rate of Organic Free Radical Polymerization" by KW Dryson (Section 2 of the Polymer Handbook, Vol. 1, 4th Edition, Wiley-Interscience, 1999), which is incorporated herein by reference in its entirety.

[0113] Maleination reactions in natural oils can occur under heating in three different ways. The first is known as the "ene" reaction (reaction between allylic hydrogen and enophyl - pericyclic reaction), which gives a triglyceride structure with an anhydride moiety (succinic anhydride). The second is a radical addition consuming the double bond of the fatty acid, incorporating succinic anhydride into the natural oil structure. The last reaction is also a radical addition, but it incorporates maleic anhydride into the natural oil structure without consuming the C=C bond (fatty acid chain and maleic anhydride). This reaction occurs by deprotonation of the hydrogen between the two alkene groups. The maleated natural oils can then react with hydrophobic and hydrophilic moieties of hydrocarbyl alcohols, hydrocarbyl amines, silicon-based compounds forming a network structure (see examples). This type of reaction was applied to reactions occurring by heating at 210 °C for 6-10 hours.

[0114] Thus, the reactions in the above non-limiting examples may be carried out at elevated temperatures, such as, for illustration purposes only, temperatures of about 150° C. to about 300° C., alternatively about 170° C. to about 230° C., or alternatively about 200° C. to about 220° C. The reaction time may be about 0.5 hours to about 10 hours. In one embodiment, the reaction time is about 1 hour to about 5 hours, and in another embodiment, about 2 hours to 4 hours. In another embodiment, the reaction time is about 6 hours to 10 hours.

[0115] During maleation, the molar ratio of natural oil to maleic anhydride in some embodiments is equal to 1, in other embodiments is between 1 and 2, in other embodiments is between 1 and 2.8, and in still other embodiments is between 1 and 3.2 moles of maleic anhydride per mole of natural oil.

[0116] The molar ratio of reaction of the maleated natural oil with the hydrophobic moiety, the hydrophilic moiety, or a combination mixture thereof is equal to 1:1 to form a reaction product having at least one unreacted maleic acid functional group.

[0117] In one non-limiting embodiment, the composition is a skin care composition, an oral care composition, a hair care composition, an energy composition, a construction composition, a biocidal composition, a preservative composition, a nutraceutical composition, a food composition, an agricultural composition, a coating composition, a cosmetic composition, a home care composition, an industrial and institutional composition, a textile composition, a laundry composition, a cleaning composition, or a disinfecting composition.

[0118] According to another embodiment of the present application, it is expected to employ at least one sensory system active ingredient selected from the group consisting of skin care ingredients, hair care ingredients, oral care ingredients, home care ingredients, energy based ingredients, construction based ingredients, biocide based ingredients, preservative based ingredients, nutraceutical based ingredients, food based ingredients, agricultural based ingredients, coating based ingredients, cosmetic based ingredients, industrial and institutional based ingredients, textile based ingredients, laundry based ingredients, cleaning based ingredients, or disinfecting based ingredients.

[0119] In accordance with another embodiment of the present application, it is anticipated that at least one personal care ingredient, including a color cosmetic ingredient, a hair care ingredient, a skin care ingredient, or a sun care ingredient, will be employed.

[0120] According to another embodiment of the present application, it is expected to employ at least one personal care ingredient selected from the group consisting of water insoluble ingredients, oxidizing agents, conditioning agents, humectants, pH adjusting buffers, waxes, mineral oils, emulsifiers, fatty substances, gelling agents, thickening agents, emollients, hydrophilic or lipophilic active agents, antioxidants, sequestering agents, preservatives, acidifying or basifying agents, fragrances, excipients, dyes, botanical extracts, moisturizing creams, proteins, peptides, neutralizing agents, solvents, anti-dandruff ingredients, reducing agents, and combinations thereof.

[0121] In some embodiments, suitable ranges of the reaction product of maleated natural oil and one or more functional or non-functional moieties selected from hydrophobic moieties, hydrophilic moieties, or combinations can vary from about 0.01 wt. % to about 0.1 wt. %, from about 0.1 wt. % to about 1 wt. %, or from about 1 wt. % to about 5 wt. %, or from about 5 wt. % to about 10 wt. %, based on the total weight of the aqueous personal care composition.

[0122] In some embodiments, a suitable range of the sensory system actives of the present application is from about 0.1% to about 1% by weight, or from about 1% to about 2.5% by weight, or from about 2.5% to about 5% by weight, or from about 5% to about 10% by weight, or from 10% to about 15% by weight, or from about 15% to about 20% by weight, or from about 20% to about 25% by weight, or from about 25% to about 30% by weight, or from about 30% to about 35% by weight, based on the total weight of the oral care antimicrobial agent. It may vary by 5% by weight, or from about 35% to about 40% by weight, or from about 40% to about 45% by weight, or from about 45% to about 50% by weight, or from about 50% to about 55% by weight, or from about 55% to about 60% by weight, or from about 60% to about 65% by weight, or from about 65% to about 70% by weight, or from about 70% to about 75% by weight, or from about 75% to about 80% by weight, or from about 80% to about 85% by weight, or from about 85% to about 90% by weight.

[0123] In some embodiments, a suitable range of the personal care ingredient of the present application is from about 0.1% to about 1% by weight, or from about 1% to about 2.5% by weight, or from about 2.5% to about 5% by weight, or from about 5% to about 10% by weight, or from 10% to about 15% by weight, or from about 15% to about 20% by weight, or from about 20% to about 25% by weight, or from about 25% to about 30% by weight, or from about 30% to about 35% by weight, based on the total weight of the oral care antimicrobial composition. It may vary by 5% by weight, or from about 35% to about 40% by weight, or from about 40% to about 45% by weight, or from about 45% to about 50% by weight, or from about 50% to about 55% by weight, or from about 55% to about 60% by weight, or from about 60% to about 65% by weight, or from about 65% to about 70% by weight, or from about 70% to about 75% by weight, or from about 75% to about 80% by weight, or from about 80% to about 85% by weight, or from about 85% to about 90% by weight.

[0124] In some embodiments, a suitable range of the skin care ingredient of the present application is from about 0.1% to about 1% by weight, or from about 1% to about 2.5% by weight, or from about 2.5% to about 5% by weight, or from about 5% to about 10% by weight, or from 10% to about 15% by weight, or from about 15% to about 20% by weight, or from about 20% to about 25% by weight, or from about 25% to about 30% by weight, or from about 30% to about 35% by weight, based on the total weight of the oral care antimicrobial composition. %, or from about 35% to about 40% by weight, or from about 40% to about 45% by weight, or from about 45% to about 50% by weight, or from about 50% to about 55% by weight, or from about 55% to about 60% by weight, or from about 60% to about 65% by weight, or from about 65% to about 70% by weight, or from about 70% to about 75% by weight, or from about 75% to about 80% by weight, or from about 80% to about 85% by weight, or from about 85% to about 90% by weight.

[0125] According to another embodiment of the present application, the aqueous personal care composition of the present application is formulated into a spray, lotion, mousse, fluid, serum, solution, perm, emulsion, gel, vesicle, dispersion, paste, cream, solid stick, shampoo, balm, wipe, milk, foam, jelly, and / or liquid.

[0126] The reactions and compositions of the present application may be analyzed by known techniques, particularly suitable for interpreting identity, residual monomer concentration, molecular weight, and molecular weight distribution are 13C nuclear magnetic resonance (NMR), gas chromatography (GC), infrared (IR), liquid chromatography (LC), and gel permeation chromatography (GPC) techniques.

[0127] Further, certain aspects of the present application are described in detail by the following examples, which are provided herein to illustrate, but not to limit, the present application. EXAMPLES

[0128] Example A: Grafting of maleic anhydride onto natural oils Example A1: Grafting of 1 mole of maleic anhydride onto soybean oil A 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 600 g yellow soybean oil and 67 g (1 molar equivalent based on SBO) maleic anhydride. The mixture was sparged with nitrogen only at RT for 15 min. The mixture was slowly heated from room temperature to 210 °C and held isothermally at 210 °C for approximately 6-8 h. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product characterized by NMR and LC with <1% residual maleic anhydride. [ka]

[0129] Example A2: Grafting of 2 moles of maleic anhydride onto soybean oil A 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 600 g yellow soybean oil and 137.7 g (2 molar equivalents based on SBO) maleic anhydride. The mixture was sparged with nitrogen only at RT for 15 min. The mixture was slowly heated from room temperature to 210 °C and held isothermally at 210 °C for approximately 6-8 h. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product characterized by NMR and LC with <1% residual maleic anhydride. [ka]

[0130] Example A3: Grafting of 3 moles of maleic anhydride onto soybean oil A 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 600 g yellow soybean oil and 204 g (3 molar equivalents based on SBO) maleic anhydride. The mixture was sparged with nitrogen only at RT for 15 min. The mixture was slowly heated from room temperature to 210 °C and held isothermally at 210 °C for approximately 6-8 h. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product characterized by NMR and LC with <1% residual maleic anhydride. [ka]

[0131] Example A4: Grafting of maleic anhydride onto palm oil A 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparging adapter, and mechanical stirrer was charged with 100 g palm oil and 23 g (2 molar equivalents based on palm oil) maleic anhydride. The mixture was sparged with nitrogen only at RT for 15 min. The mixture was slowly heated from room temperature to 210 °C and held isothermally at 210 °C for approximately 8-10 h. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product characterized by NMR and LC with <1% residual maleic anhydride.

[0132] Example A5: Grafting of maleic anhydride onto canola oil A 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparging adapter, and mechanical stirrer was charged with 100 g canola oil and 22.2 g (2 molar equivalents based on canola oil) maleic anhydride. The mixture was sparged with nitrogen only at RT for 15 min. The mixture was slowly heated from room temperature to 210 °C and held isothermally at 210 °C for approximately 8-10 h. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product characterized by NMR and LC with <1% residual maleic anhydride.

[0133] Example A6: Grafting of maleic anhydride onto sunflower oil A 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparging adapter, and mechanical stirrer was charged with 100 g sunflower oil and 22.4 g (2 molar equivalents based on sunflower oil) maleic anhydride. The mixture was sparged with nitrogen only at RT for 15 min. The mixture was slowly heated from room temperature to 210 °C and held isothermally at 210 °C for approximately 8-10 h. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product characterized by NMR and LC with <1% residual maleic anhydride.

[0134] Example A7: Grafting of maleic anhydride onto castor oil A 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g yellow castor oil and 21 g (2 molar equivalents based on castor oil) maleic anhydride. The mixture was sparged with nitrogen only at RT for 15 min. The mixture was slowly heated from room temperature to 210 °C and held isothermally at 210 °C for approximately 8-10 h. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product characterized by NMR and LC with <1% residual maleic anhydride.

[0135] Example B: Grafting of hydrophobic alcohol (octyldodecanol) onto maleic anhydride on natural oil Example B1: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A1 and 30.5 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride. [ka]

[0136] Example B2: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A2 and 55.64 g (2 molar equivalents) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0137] Example B3: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A2 and 61.20 g (2.2 molar equivalents) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product characterized by NMR, GC with <5% residual octyldodecanol, and LC with <1% residual maleic anhydride.

[0138] Example B4: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A3 and 25.44 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0139] Example B5: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A3 and 31.81 g (1.25 molar equivalents) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0140] Example B6: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A3 and 38.17 g (1.5 molar equivalents) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0141] Example B7: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A3 and 50.89 g (2 molar equivalents) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0142] Example B8: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A3 and 63.61 g (2.5 molar equivalents) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0143] Example B9: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A4 and 35 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0144] Example B10: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A5 and 35 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0145] Example B11: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A6 and 35 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0146] Example B12: In a 1 liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction Example A7 and 35 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed, heated to 90° C., and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded a >96% amber viscous product that was characterized by NMR, IR, GC for <5% residual octyldodecanol, and LC for <1% residual maleic anhydride.

[0147] Example C: Grafting of hydrophobic and hydrophilic moieties (glycerin) onto hydrophobic maleic anhydride on natural oil with octyldodecanol Example C1: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from reaction B6 and 5.7 g (1 molar equivalent) of glycerin were mixed, heated to 90°C, and held for 4-6 hours. The catalyst- and solvent-free one-pot reaction yielded >96% amber viscous product characterized by NMR and LC with <0.05% residual maleic anhydride. [ka]

[0148] Example C2: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from reaction B4 and 6.28 g (1 molar equivalent) of glycerin were mixed, heated to 90°C, and held for 4-6 hours. The catalyst- and solvent-free one-pot reaction yielded >96% amber viscous product characterized by NMR and LC with <0.05% residual maleic anhydride.

[0149] Example C3: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from reaction B4 and 9.42 g (1.5 molar equivalents) of glycerin were mixed, heated to 90° C., and held for 4 hours. The catalyst- and solvent-free one-pot reaction yielded >96% amber viscous product characterized by NMR and LC with <0.05% residual maleic anhydride.

[0150] Example C4: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from reaction B9 and 11 g (1 molar equivalent) of glycerin were mixed, heated to 90°C, and held for 4-6 hours. The catalyst- and solvent-free one-pot reaction yielded >96% amber viscous product characterized by NMR and LC with <0.05% residual maleic anhydride.

[0151] Example C5: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from reaction B10 and 11 g (1 molar equivalent) of glycerin were mixed, heated to 90°C, and held for 4-6 hours. The catalyst- and solvent-free one-pot reaction yielded >96% amber viscous product characterized by NMR and LC with <0.05% residual maleic anhydride.

[0152] Example C6: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from reaction B11 and 11 g (1 molar equivalent) of glycerin were mixed, heated to 90°C, and held for 4-6 hours. The catalyst- and solvent-free one-pot reaction yielded >96% amber viscous product characterized by NMR and LC with <0.05% residual maleic anhydride.

[0153] Example C7: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from reaction B12 and 11 g (1 molar equivalent) of glycerin were mixed, heated to 90°C, and held for 4-6 hours. The catalyst- and solvent-free one-pot reaction yielded >96% amber viscous product characterized by NMR and LC with <0.05% residual maleic anhydride.

[0154] Example C8: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 152 g of the amber viscous product from reaction B4 and 4.74 g (1 molar equivalent) of ethanol were mixed, heated to 90° C., and held for 8 hours. The catalyst- and solvent-free one-pot reaction afforded >96% amber product characterized by NMR and LC with <0.05% residual maleic anhydride. [ka]

[0155] Example C9: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 152 g of the amber viscous product from reaction B4 and 9.47 g (2 molar equivalents) of ethanol were mixed, heated to 90° C., and held for 8 hours. The catalyst- and solvent-free one-pot reaction afforded >96% amber product characterized by NMR and LC with <0.05% residual maleic anhydride.

[0156] Example D: Grafting of hydrophilic alcohols (beta cyclodextrin, glycerin) onto maleic anhydride on natural oils Example D1: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 68.43 g of the amber viscous product from reaction B6 and 23.73 g (0.50 molar equivalents) of beta cyclodextrin were mixed and heated to 90° C. and held for 6 hours. The catalyst- and solvent-free one-pot reaction yielded >96% yellow product characterized by IR and LC with <0.05% residual maleic anhydride. [ka]

[0157] Example D2: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 68.43 g of the amber viscous product from reaction B6 was mixed with 23.73 g (0.50 molar equivalents) of beta cyclodextrin and 3.85 g (1 molar equivalent) of glycerin, heated to 90° C., and held for 4 hours. The catalyst- and solvent-free one-pot reaction yielded >96% yellow product characterized by IR and LC with <0.05% residual maleic anhydride. [ka]

[0158] Example D3: In a 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 68.43 g of the amber viscous product from reaction B6, 23.73 g (0.50 molar equivalents) of beta cyclodextrin, and 1.93 g (0.50 molar equivalents) of glycerin were mixed, heated to 90° C., and held for 4 hours. The one-pot reaction without catalyst or solvent gave a >96% yellow product, characterized by IR and LC with <0.05% residual maleic anhydride. The one-pot reaction without catalyst or solvent gave a >96% yellow product, characterized by IR and LC with <0.05% residual maleic anhydride.

[0159] Example E: Maleation reaction with water Example E1: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 100 g of the amber viscous product from maleation reaction A3 and 6.10 g (3 molar equivalents) of water were mixed, heated to 90° C., and held for 20 h. The catalyst- and solvent-free one-pot reaction yielded >90% yellow product characterized by NMR, IR, and LC with <0.05% residual maleic acid. [ka]

[0160] Example F: Grafting of hydrophilic glycerin onto maleic anhydride on soybean oil Example F1 In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 176 g of the amber viscous product from maleation reaction A3 and 6.87 g (0.5 molar equivalents) of glycerin were mixed, heated to 90° C., and held for 2 hours. The catalyst- and solvent-free one-pot reaction yielded >96% yellow product characterized by IR and LC with <0.05% residual maleic anhydride. [ka]

[0161] Example F2: In a 1 L 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer, 176 g of the amber viscous product from maleation reaction A3 and 13.74 g (1 molar equivalent) of glycerin were mixed, heated to 90° C., and held for 4 hours. The catalyst- and solvent-free one-pot reaction yielded >96% yellow product characterized by IR and LC with <0.05% residual maleic anhydride.

[0162] Nonionic Sunscreen Emulsion Procedure In Phase A, water and glycol were added to a glass beaker. Sprinkle in carbomer and mix until all is incorporated and smooth. Phase B ingredients were weighed out and heated to a temperature of 75-80°C and slowly added to Phase A while continuing to homogenize. The homogenized mixture was cooled to 60-65°C. Phase C ingredients were weighed out and slowly added to the homogenized mixture of Phase A and Phase B while continuing to homogenize. pH was adjusted as needed. A sweep mix was performed until the reactor was cooled.

[0163] Water-in-silicon mineral (zinc and titanium) emulsion procedure Phase A ingredients were pre-weighed, ingredients were mixed, heated to 40-45°C, homogenized until uniform, and then cooled to 30-35°C. In a separate beaker, Phase C was added, heated to 65°C, and mixing continued until clear. Phase C was cooled to 35-40°C. Phase B was milled and added to Phase C while mixing at medium to high speed. Phase A was slowly added to the mixture of Phases B and C and mixing continued at medium to high speed for approximately 10 minutes. Cooled to room temperature.

[0164] W / Si Mineral (Zinc) Emulsion Procedure In Phase A, Dimethicone 1 and Dimethicone 2 were added to the main beaker and mixing at high speed with a high lift mixing blade was started. Cetyl PEG / PPG-10 / 1 Dimethicone was added and mixing at high speed was continued followed by Polyglyceryl-4 Isostearate, Cetyl PEG / PPG-10 / 1 Dimethicone, and Hexyl Laurate, and mixing was continued. Next, Caprylic / Capric Triglyceride, Stearalkonium Hectorite, and Propylene Carbonate were added. In a separate beaker, Phase B ingredients were combined and mixed. Once the Phase B mixture was uniform, it was added to Phase A and mixing was continued. In a separate beaker, Phase C ingredients were added. Water was added and mixing was continued followed by Hydroxyethylcellulose and heating to 80-85°C, once dispersed, Glycerin and Butylene Glycol were added, mixing was continued and heating to 85°C until Hydroxyethylcellulose was solubilized, followed by Phenoxyethanol and Salt. Ensure all salts are dissolved and begin slow cooling to room temperature. Once all ingredients of Phase C are uniform, spread the mix over Phase A and slowly pour Phase C into Phase A. Continue mixing until uniform. Add zinc oxide to main batch and continue prop mixing for 5 minutes until batch is homogenous. Switch on homogenizer and continue homogenizing for 10 minutes.

[0165] Anionic Emulsion Procedure In Phase A, water, glycerin, glyceryl acrylate / acrylic acid copolymer and PVM / MA copolymer were added to a glass beaker and heated to 75-80°C. Sprinkle in the acrylic acid / VP crosspolymer and mix until all is incorporated and smooth. Phase B ingredients were weighed out, heated to a temperature of 75-80°C, slowly added to Phase A and continued homogenization. The homogenized mixture was cooled to 60-65°C. Phase C ingredients were weighed out and slowly added to the homogenized mixture of Phase A and Phase B and continued homogenization. pH was adjusted as needed. A sweep mix was performed until the reactor was cooled.

[0166] Hydrosheer® Spray Instructions Phase A ingredients were mixed in a container until completely dissolved. In a separate container, Phase B ingredients were mixed and heated at low temperature until the crystals were dissolved. Phase B was added to Phase A and mixing was continued until homogeneous.

[0167] Lipstick Formulation Procedure Phase A ingredients were pre-weighed, ingredients were mixed, heated to 90-95°C, and homogenized until everything was clear. Phase B was milled, then added to Phase A, continued mixing, and a glass slide was used to ensure everything was in. Phase C ingredients were added and mixing continued for 5 minutes until clear. Phase D ingredients were added and mixing continued for 15 minutes until clear. Two glass slides were used to ensure pigment dispersion. SB-700 was added and mixed well. Poured into molds at 80°C and refrigerated for 10 minutes.

[0168] Example G: Formulation with B1 Example G1: [Table 1]

[0169] Example G2: [Table 2]

[0170] Example G3: [Table 3-1] [Table 3-2]

[0171] Example G4: [Table 4]

[0172] Example G5: [Table 5]

[0173] Example G6 [Table 6-1] [Table 6-2]

[0174] Example H: Formulation with C1 Example H1: [Table 7]

[0175] Example H2: [Table 8]

[0176] Example H3: [Table 9-1] [Table 9-2]

[0177] Example H4: [Table 10-1] [Table 10-2]

[0178] Example H5: [Table 11]

[0179] Example H6: [Table 12-1] [Table 12-2]

[0180] Example I: Formulation with C4 Example I1: [Table 13]

[0181] Example I2 : [Table 14]

[0182] Example I3: [Table 15-1] [Table 15-2]

[0183] Example I4: [Table 16-1] [Table 16-2]

[0184] Example I5: [Table 17]

[0185] Example I6: [Table 18-1] [Table 18-2]

[0186] Example J: Formulations with D1 or D2 Example J1: [Table 19]

[0187] Example J2: [Table 20]

[0188] Example J3: [Table 21]

[0189] Example J4: [Table 22-1] [Table 22-2]

[0190] Example J5: [Table 23]

[0191] Example J6: [Table 24]

[0192] While the compositions and methods of the disclosed and / or claimed inventive concepts have been described in terms of specific embodiments, it will be apparent to one of ordinary skill in the art that changes may be made to the compositions and / or methods in any step or sequence of steps of the methods described herein without departing from the concept, spirit and scope of the disclosed and / or claimed inventive concepts. All 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 concepts.

Claims

1. (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof; wherein the hydrophilic moiety is not a glycerol moiety; the reaction product has unreacted maleic acid functionality or has maleic acid functionality functionalized with a hydrophobic moiety, a hydrophilic moiety, or a combination thereof; A composition selected from the group consisting of skin care compositions, oral care compositions, hair care compositions, energy compositions, construction compositions, biocidal compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, cosmetic compositions, home care compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, and disinfecting compositions.

2. the hydrophobic moiety is a moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohol, any of the foregoing groups with or without heteroatoms, including from about 6 to about 36 carbon atoms, unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl amine, any of the foregoing groups with or without heteroatoms, including from about 6 to about 36 carbon atoms, silicon-based compounds, and combinations thereof; the hydrophobic alcohol is selected from the group consisting of heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-octyl-1-dodecyl alcohol, 2-tetradecanol, 2-hexadecanol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4-methyl-1-pentanol, and mixtures thereof; or the hydrophobic amine is selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, dimethylamine, and mixtures thereof; or 2. The composition of claim 1, 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-hydroxypolyalkyleneoxypropylmethylsiloxane, and mixtures thereof.

3. the hydrophilic moiety is a moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols, any of which may or may not have heteroatoms and have from about 1 to about 5 carbon atoms, unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl amines, any of which may or may not have heteroatoms and have from about 1 to about 5 carbon atoms, unsubstituted or substituted polyols, any of which may or may not have heteroatoms and have from about 2 to about 36 carbon atoms, silanes, and combinations thereof; the silane is functionalized with an alcohol or an amine, and combinations thereof; or the hydrophilic alcohol is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, methoxypolyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, L-ribose, 2-deoxy-D-galactose, and mixtures thereof; or, the hydrophilic amine is selected from the group consisting of 2-methylpentane-1,5-diamine, diethanolamine, diisopropanolamine, serinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, N-methyl-D-glucosamine, D-galactosamine hydrochloride, D-glucosamine hydrochloride, D-mannosamine hydrochloride, and mixtures thereof; or, 2. The composition of claim 1, wherein the silane is a hydrophilic compound selected from the group consisting of 3-aminopropyl silanetriol, N-(2-aminoethyl)-3-aminopropyl silanetriol, and mixtures thereof.

4. 2. The composition of claim 1, wherein the maleated natural oil is selected from the group consisting of maleated avocado oil, maleated palm oil, maleated corn oil, maleated cottonseed oil, maleated jojoba oil, maleated linseed oil, maleated nut oil, maleated olive oil, maleated palm oil, maleated raisin oil, maleated rapeseed oil, maleated safflower oil, maleated sesame oil, maleated soybean oil, maleated pumpkin oil, maleated sunflower oil, maleated almond oil, maleated canola oil, maleated flaxseed oil, maleated grapeseed oil, maleated palm oil, maleated palm kernel oil, maleated peanut oil, maleated walnut oil, and mixtures thereof, or is maleated soybean oil.

5. (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) a functional or non-functional hydrophobic moiety according to claim 2; and (c) a glycerol moiety; 1. A composition comprising the reaction product of the reaction product has unreacted maleic acid functional groups; The composition, wherein the compound is selected from the group of structures represented by the structures set forth below. 【Chemical 1】

6. A compound selected from the group of structures represented by the structures depicted below: 【Chemistry 2】

7. A composition comprising a compound selected from the group of structures represented by the structures depicted below: 【Chemistry 3】

8. (A) (a) a maleated natural oil comprising the natural oil having maleic acid functional groups according to claim 1; (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, according to claim 2 or 3; (provided that the hydrophilic moiety is not a glycerol moiety), (B) (a) a sensory system active ingredient; A composition comprising:

9. (A) (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) a functional or non-functional hydrophobic moiety according to claim 2; and (c) a glycerol moiety; and the reaction product of (B) a sensory system active ingredient; A composition comprising: the reaction product has unreacted maleic acid functional groups; The composition, wherein the compound is selected from the group of structures represented by the structures set forth below. 【Chemistry 4】

10. (A) (a) a maleated natural oil comprising the natural oil having maleic acid functional groups according to claim 1; (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, according to claim 2 or 3; (provided that the hydrophilic moiety is not a glycerol moiety), (B)(a) a personal care sensory system active ingredient; 1. A personal care composition comprising:

11. (A) (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) a functional or non-functional hydrophobic moiety according to claim 2; and (c) a glycerol moiety; and the reaction product of (B) personal care sensory system active ingredients; 1. A personal care composition comprising:

12. (A) (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) a functional or non-functional moiety selected from the group consisting of a hydrophobic moiety, a hydrophilic moiety, and combinations thereof, according to claim 2 or 3; (provided that the hydrophilic moiety is not a glycerol moiety), (B)(a) skin care sensory system active ingredients; 1. A skin care composition comprising: The reaction product has unreacted maleic acid functional groups.

13. (A) (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) a functional or non-functional hydrophobic moiety according to claim 2; and (c) a glycerol moiety; and the reaction product of (B) skin care sensory system active ingredients; 1. A skin care composition comprising:

14. (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) two functional or non-functional hydrophilic moieties according to claim 3; 1. A composition comprising the reaction product of The reaction product has unreacted maleic acid functional groups.

15. (A) (a) a maleated natural oil comprising a natural oil having maleic acid functional groups; (b) two functional or non-functional hydrophilic moieties; and the reaction product of (B) a sensory system active ingredient; A composition comprising: The composition, wherein the sensory system active is a personal care sensory system active or a skin care sensory system active.

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