Metal working fluid composition comprising modified maleated natural oils, salts and use thereof

Abstract

The present application provides a metal working fluid composition comprising: a reaction product comprising a maleated natural oil, comprising a natural oil with maleated functionality; and a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof. Also, the present application provides metal working fluid composition comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a base. Also, the present application provides a metal working fluid composition comprising a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base.

Description

METAL WORKING FLUID COMPOSITION COMPRISING MODIFIED MALEATED NATURAL OILS, SALTS AND USE THEREOFFIELD OF THE INVENTION

[0001] The present application provides a metal working fluid composition comprising a reaction product of a maleated natural oil; a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties; a base and combinations thereof.BACKGROUND OF THE INVENTION

[0002] Modified natural oils can be incorporated into a wide variety of compositions. Such compositions include, but are not limited to, personal care (e.g., hair care, sun care, skin care, oral care), adhesives, coatings, paints, electronics, household, industrial and institutional (HI&I) compositions, inks, membranes, metal working fluids, oilfield chemicals, plastics and plasticizers, textiles, industrial products, biocides, pharmaceuticals / nutritionals, and agrochemical compositions.

[0003] Natural oils are useful for synthesizing renewable compounds such as polymers, plastics, and plasticizers, which compounds are useful in a variety of agricultural compositions. A difficulty with utilizing natural oils is that they are blends of triglycerides containing varying degrees of unsaturated groups, which unsaturated groups are relatively unreactive. To make these natural oils reactive, these unsaturated groups are generally chemically modified to make them reactive. For example, these unsaturated groups can be reacted to provide epoxide functional groups or succinic anhydride functional groups. Despite these chemical modifications, 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] Metalworking fluids (MWFs) play an essential role in the machining and metalworking industry. The primary function of these fluids is to reduce friction and wear, cool and lubricate the cutting tool, and remove chips and other debris from the cutting zone. For many years, the most common fluids used for these purposes were mineral oil-based fluids, but in recent years, there hasbeen a growing interest in the use of vegetable oils as an alternative. Vegetable oils are an attractive option for several reasons.

[0005] 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.

[0006] 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.

[0007] 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.

[0008] A discussion of generalized reaction between maleic anhydride and unsaturated vegetable oils is provided in the Elandbook of Maleic Anhydride Based Materials: Syntheses, Properties and Applications by Osama. M. Musa in chapter 3 page 166, published in Springer International Publishing Switzerland 2016.

[0009] US Patent 2754306A describes a reaction of soybean oil, maleic anhydride and iso-octyl alcohol to provide an improved plasticizer for nitrocellulose compositions.

[0010] PCT Publications WO2023043593, W02023081006, WO2023235637,WO2024197173, and WO2024197212 discloses modified naturals oils in various applications.

[0011] PCT Applications 2019113068A1 describe a technology related to metalworking fluids comprising maleated soybean oil derivatives.

[0012] 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.

[0013] 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 landanimal and further reacted with water, Group TA and TIA metals, ammonium hydroxide, various amines, alkanolamines, polyols, alkoxylated alkanolamines, poly (alkylene oxide)s, or polyamines or mixtures.

[0014] U.S. patent 9920276 B2 describes a reaction product of maleated soybean oil with the reaction product of a polyalkanoic or polyalkenoic acid as lubricants in metal processing including cutting, grinding or plastic working.

[0015] Vegetable-based lubricants are gaining attention as an ecofriendly alternative to petroleum-based lubricants due to their renewability, biodegradability, and lower toxicity. Many researchers are exploring the use of various vegetable oils as potential candidates for metalworking fluids. Overall, there is still much work to be done to fully realize the potential of vegetable oils as a sustainable and environmentally friendly alternative to petroleum-based lubricants in the application of metal working fluids.

[0016] The present invention is a metal working fluid composition comprising a reaction product of modified natural oils and their salts are effectively used for the protection of tools against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion, increased operational efficiency, longer tool life, chip removal from the processing zone, excellent cooling and lubrication properties, thermal stability, improved surface finish, enhanced fluid life, foam and soap reduction, lower energy consumption and lower total cost of operations.SUMMARY OF THE INVENTION

[0017] The present application provides a metal working fluid composition comprising: (A) a reaction product comprises a maleated natural oil, comprising a natural oil with maleated functionality; and a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moi eties, hydrophilic moi eties, and combinations thereof.

[0018] Another aspect of the present invention provides a metal working fluid composition comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a base.

[0019] Another aspect of the present invention provides a metal working fluid composition comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil withmaleated functionality; and (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base.

[0020] Another aspect of the present invention provides a metal working fluid composition comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) a base; wherein the maleated functionality has been partially reacted with the base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety.

[0021] Another aspect of the present invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% reaction product comprising a maleated natural oil, comprising a natural oil with maleated functionality; and a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof ; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0022] Another aspect of the present invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a base.; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0023] Another aspect of the present invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0024] Another aspect of the present invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% reaction product having a polymer of (a) amaleated natural oil, comprising a natural oil with maleated functionality; and (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0025] Another aspect of the present invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) a base; wherein the maleated functionality has been partially reacted with the base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety ; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0026] Another aspect of the present invention provides a metal working fluid composition used for protection of tool against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion, increased operational efficiency, longer tool life, chip removal from the processing zone, excellent cooling and lubrication properties, thermal stability, improved surface finish, enhanced fluid life, foam and soap reduction, lower energy consumption and lower total cost of operations.

[0027] One more aspect of the present invention is to provide a method for preparing metal working fluid composition, wherein the method comprises the following steps: (a) mixing a reaction product (A) maleated natural oil; a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties; a base and combinations thereof of the invention with water, amines and an emulsifier and the mixture was mixed under stirring thoroughly, obtaining the first mixed material (1); (b) then the obtained mixture (1) is mixed with coupling agent, lubrication additive, and bactericide to obtain second mixture (2); (c) adding base oil, and optionally adding any other additional metal working fluid additive to the second mixture (2) to obtain the third mixture of (3); and (d) adding a antifoaming agent to the third mixture (3) by stirring and mixing, to result the metal working fluid.

[0028] Another aspect of the present invention is to provide method for preparing metal working fluid composition wherein the step (a) the stirring of the stirring speed is preferably 400 to 800rpm or until a vortex appears, step (a) the stirring time is preferably 10 to 20 min; step (a), the stirring temperature is 25-40 degrees centigrade, preferably, step (2) the stirring of the stirring speed is preferably 400 to 800rpm, or until a vortex appears;, the stirring time in the step (b) is 10 - 20 min; step (b), the stirring temperature is 25-40 degrees centigrade, step (c) the stirring of the stirring speed 400 to 800rpm, or until a vortex appears;, the stirring time in the step (c) 10 to 20min, step (c), the stirring temperature is 25-40 degrees centigrade.BRIEF DESCRIPTION OF THE FIGURES

[0029] Further embodiments of the present application can be understood with the appended figures.

[0030] Figure 1 represents the naphthenic oil control, Form#l shows corrosion at 5 wt%. Reduced corrosion in Form#2, Form#3,and Form#8 are clearly visible in the samples.

[0031] Figure 2 represents the control, Form#l shows the highest torque and the worst lubricity. Form#7 shows a far lower torque value indicating heightened lubricity.

[0032] Figure 3 represents the naphthenic oil control, Form#9 shows corrosion at 3 wt%. Form#10, #13, and #17 all show matching corrosion, while others show decreased corrosion performance.

[0033] Figure 4 represents the naphthenic oil control, Form#8 shows the highest torque and the worst lubricity. All other modified oil samples show lower torque, indication better lubricity by 8- 12%.

[0034] Figure 5 represents the naphthenic oil control, Form#8 containing a minimal amount of emulsifier necessary to form a stable emulsion. All other modified oil samples show far lower emulsifier needed to create a stable emulsion. Form#21 requires no additional emulsifier to create a clear, transparent solution, exhibiting excellent performanceDETAILED DESCRIPTION OF THE INVENTION

[0035] The present application provides a metal working fluid composition comprising: (A) a reaction product comprises a maleated natural oil, comprising a natural oil with maleated functionality; and a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moi eties, hydrophilic moi eties, and combinations thereof.

[0036] Also, the present application provides metal working fluid composition comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a base.

[0037] Also, the present application provides a metal working fluid composition comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base.

[0038] Also, the present application provides a metal working fluid composition comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) a base; wherein the maleated functionality has been partially reacted with the base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety.

[0039] Natural oils are abundant, inexpensive, and are derived from sustainable sources. Natural oils are useful for synthesizing renewable compounds such as polymers, plastics, and plasticizers, which compounds are useful in a variety of compositions. A difficultly with utilizing natural oils is that they are blends of triglycerides containing varying degrees of unsaturated groups, which unsaturated groups are relatively unreactive. To make these natural oils reactive, these unsaturated groups are generally chemically modified to make them reactive. For example, these unsaturated groups can be reacted with maleates to provide epoxide functional groups and succinic anhydride functional groups. Despite these chemical modifications, the maleated natural oils can still exhibit limited properties such as insolubility or non-dispersibility in water and alcohols. Accordingly,there is a need for further modified maleated natural oils which do not exhibit the limited properties of maleated natural oils.

[0040] 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.

[0041] 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’.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] The term “reaction product” refers to a substance produced from a chemical reaction of one or more reactant substances.

[0051] 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.

[0052] 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 of maleic anhydride, the “maleated functionality” could also be considered a succinyl anhydride moiety attached to one or more fatty acid chain in the natural oil

[0053] As used herein, the term “moiety” or “moieties” refers to a part or a functional group(s) of a molecule.

[0054] 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.

[0055] 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.

[0056] The term “organic base”, as used herein, includes ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.

[0057] The term “inorganic base”, as used herein, includes oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.

[0058] The term “alkali metal base” includes oxides, hydroxides, carbonates, or bicarbonates of sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr).

[0059] 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).

[0060] 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).

[0061] The term “metal working fluid” refers to any fluid which is liquid, used in a metal working process for one or more functions, which can include cooling, lubrication, debris removal, reducing or inhibiting corrosion, reducing or inhibiting material build up on workpieces and / or metal working tools, etc. The metal working fluid may be aqueous, a liquid, a spray, a paste, a gel, an emulsion, or a mist.

[0062] The term “metal working fluid composition” here in used for protection of tool against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion, increased operational efficiency, longer tool life, chip removal from the processing zone, excellent cooling and lubrication properties, thermal stability, improved surface finish, enhanced fluid life, foam and soap reduction, lower energy consumption and lower total cost of operations.

[0063] The term “metal working process” refers to any mechanical process which uses a metal working tool. Such processes and application can include, metal forming, machining, grinding, milling, cutting, honing, stamping, drilling, boring, broaching, casting, forging, rolling, piercing, coining, drawing, press forming, deburring, grooving, tapping, chamfering, broaching, reaming, lapping, straightening, and turning operations in automatic and manual machines.

[0064] The term “metal working fluid additive(s)” includes additives selected from the group consisting of metal deactivators, lubricants, emulsifiers, coupling agent, anti-wear, corrosion inhibitors, antimicrobials, extreme pressure agents, antifriction agents, bactericides, antioxidants,pH regulators, antirust agents, polymeric substances, chelating agents, base oils, solvents, liquid carriers, solid carriers or fdlers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, anti-freezing agents, clarifiers, stabilizers and mixtures thereof.

[0065] 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, acetal izati on, 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 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.

[0066] As used herein, the term "hydrophilic" means that the compound has an affinity for water, whereas "hydrophobic" means not having an affinity for water.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] The term “alkyl” refers to a functionalized or unfunctionalized, monovalent, straightchain, 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 C 1-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.

[0071] The term “aryl” refers to a functionalized or unfunctionalized, monovalent, aromatic hydrocarbyl group optionally having one or more heteroatoms. The definition of aryl includes carbocyclic and heterocyclic aromatic groups. Non-limiting examples of aryl groups include phenyl, naphthyl, indenyl, indanyl, azulenyl, fluorenyl, anthracenyl, furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 2-pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl, 1,3,4-thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,3,5-trithianyl, indolizinyl, indolyl, isoindolyl, 3H-indolyl, indolinyl, benzo[b]furanyl, 2,3-dihydrobenzofuranyl, benzo[b]thiophenyl, IH-indazolyl, benzimidazolyl, benzthiazolyl, purinyl, 4H-quinolizinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 1,8-naphthridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxyazinyl, pyrazolo[l,5-c]triazinyl, and the like.

[0072] 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.

[0073] 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.

[0074] The term “alkylene” refers to a functionalized or unfunctionalized, divalent, straightchain, 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 nonlimiting embodiment, an alkylene is a C1-C20 group. Non-limiting examples of alkylene groups include:

[0075] 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.

[0076] 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 includeether, 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.

[0077] 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, maleated flaxseed 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.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] Preferably, the silane is functionalized with an alcohol or an amine, and combinations thereof.

[0085] Preferably, the hydrophobic alcohol is selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-l -hexanol, 1 -octanol, 2-octanol, 2-butyl-l -octanol, 2-octyl-l -dodecyl alcohol, 1 -tetradecanol, 2-tetradecanol, 1- hexadecanol, 2-hexadecanol, behenyl alcohol, 3,7-dimethyl-l-octanol, 2-propyl-l -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, di ethylene 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-deoxy galactose, and mixtures thereof.

[0086] Preferably, the hydrophobic amine is selected from the group consisting of benzylamine, cyclohexyl amine, 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-l,3-propanediol, dimethylamine, and mixtures thereof.

[0087] 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.

[0088] Preferably, the hydrophobic silicon-based compound is selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl terminated poly dimethylsiloxane, poly(l,l-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated poly dimethyl siloxane, 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.

[0089] 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.

[0090] 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.

[0091] In one non-limiting embodiment, the amines selected from the group consisting of primary, secondary, and tertiary amines and combinations thereof.

[0092] 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.

[0093] 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.

[0094] In one non-limiting embodiment, the hydrocarbyl amine is a hydrophilic amine selected from the group consisting of 2-m ethylpentane- 1,5 -diamine, diethanolamine, serinol hydrochloride, 2-amino-2-ethyl-l, 3-propanediol, dimethylamine, and mixtures thereof.

[0095] 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.

[0096] 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.

[0097] In one non-limiting embodiment, the silicon-based compound is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional compound.

[0098] 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 -dimethyl silazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethyl siloxane, 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.aminopropylmethyl siloxane n-ethylaminoisobutyl terminated polydimethylsiloxane dimethylsiloxane (amino siloxane) (amino siloxane)poly ( 1 , 1 -dimethyl silazane) tel omer aminopropyl terminated polydimethylsiloxane (amino siloxane)Monoaminopropylterminated (tetramethylpiperidinyloxy)propylmethylsiloxane]- poly dimethyl siloxane (amino siloxane) dimethylsiloxane copolymerPoly dimethylsiloxane carbinol (hydroxyl) terminated polydimethylsiloxanemonocarbinol terminated polydimethylsiloxane monocarbinol terminated functional polydimethylsiloxane[bis(hydroxyethyl)amine]terminated silanol terminated polydimethylsiloxane poly dimethyl siloxanesilanol terminated polydiphenylsiloxane dodecylmethylsiloxanehydroxypolyalkyleneoxypropyl methylsiloxane

[0099] 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.

[0100] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising: (A) a reaction product comprises a maleated natural oil, comprising a natural oil with maleated functionality; and a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof. A preferred metal working fluid composition comprises compounds selected from the group of structures represented by the structures set out below:wherein R is ethyl, butyl, hexyl, octyl, 2-ethylhex-l-yl, 2-butyloct-l-yl, 2-hexyldec-l-yl, 2- octyldodec-l-yl or mixtures thereof.

[0101] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% reaction product comprising a maleated natural oil, comprising a natural oil with maleated functionality; and a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moi eties, and combinations thereof; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0102] In certain of these embodiments, the suitable ranges of (A) (that is, the maleated natural oil) of the metal working fluid composition can include discrete subranges, such as nested subranges. Exemplary nested subranges include but are not limited to, from about 0.01% to about 20% of (A); from about 0.05 % to about 20 % of (A); from about 0.10% to about 20% of (A); from about 0.50% to about 20% of (A); from about 1.0% to about 20% of (A); from about 2.5% to about 20% of (A); from about 2.5% to about 20% of (A); from about 5.0% to about 20% of (A); fromabout 7.5% to about 20% of (A); from about 10% to about 20% of (A); from about 12.5% to about 20% of (A); from about 15% to about 20 of (A); from about 17.5% to about 20% of (A); from about 0.01% to about 17.5% of (A); from about 0.01% to about 15% of(A); from about 0.01% to about 12.5% of (A); from about 0.01% to about 10% of (A); from about 0.01% to about 7.5% of (A); from about 0.01% to about 5% of (A); from about 0.01% to about 2.5% of (A); from about 0.01% to about 2.0% of (A); from about 0.01% to about 1.0% of (A); from about 0.01% to about 0.05% of (A); and from about 0.01% to about 0.05% of (A).

[0103] In certain of these embodiments, the ranges of (A) of the metal working fluid composition, based on the total % of (A), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0104] In certain of these embodiments, the suitable ranges of (B) (that is, the one or more metal working fluid additive(s)) include discrete subranges, such as nested subranges. Exemplary nested subranges of (B) include but are not limited to, from about 0.1% to about 99.9% of (B); from about 0.5% to about 99.5% of (B); from about 1.0% to about 99.0% of (B); from about 1.5% to about 98.5 % of (B); from about 2.0% to about 98.0 % of (B); from about 2.5% to about 97.5% of (B); from about 3.0% to about 97.0% of (B); from about 5.0% to about 95.0% of (B); from about 7.5% to about 92.5% of (B); from about 10.0% to about 90.0% of (B); from about 12.5% to about 87.5% of (B); from about 15.0% to about 85.0% of (B); from about 17.5% to about 87.5% of (B); from about 20.0% to about 80.0% of (B); from about 22.5% to about 75.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 30.0% to about 70.0% of (B); from about 32.5% to about 67.5 % of (B); from about 35.0% to about 65.0% of (B); from about 37.5% to about.62.5% of (B); from about 40.0% to about.60.0% of (B); from about 42.5% to about 57.5% of (B); from about 45.0% to about 55.0% of (B) and from about 47.5% to about 52.5% of (B).

[0105] In certain of these embodiments, the ranges of (B) of the metal working fluid composition, based on the total % of (B), can include specific subranges, such as bifurcatedsubranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0106] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% a reaction product of maleated soybean oil; octyldodecyl alcohol, and glycerol; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s). A preferred metal working fluid composition comprises compounds selected from the group of structures represented by the structures set out below:

[0107] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a base.

[0108] In certain of these embodiments, the suitable ranges of (A) (that is, the maleated natural oil) of the metal working fluid composition can include discrete subranges, such as nested subranges. Exemplary nested subranges include but are not limited to, from about 0.01% to about 20% of (A); from about 0.05 % to about 20 % of (A); from about 0.10% to about 20% of (A); from about 0.50% to about 20% of (A); from about 1.0% to about 20% of (A); from about 2.5% to about 20% of (A); from about 2.5% to about 20% of (A); from about 5.0% to about 20% of (A); from about 7.5% to about 20% of (A); from about 10% to about 20% of (A); from about 12.5% to about 20% of (A); from about 15% to about 20 of (A); from about 17.5% to about 20% of (A); from about 0.01% to about 17.5% of (A); from about 0.01% to about 15% of(A); from about 0.01% to about 12.5% of (A); from about 0.01 % to about 10% of (A); from about 0.01% to about 7.5% of (A); from about 0.01% to about 5% of (A); from about 0.01% to about 2.5% of (A); from about 0.01% to about 2.0% of (A); from about 0.01% to about 1.0% of (A); from about 0.01% to about 0.05% of (A); and from about 0.01% to about 0.05% of (A).

[0109] In certain of these embodiments, the ranges of (A) of the metal working fluid composition, based on the total % of (A), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0110] In certain of these embodiments, the suitable ranges of (B) (that is, the one or more metal working fluid additive(s)) include discrete subranges, such as nested subranges. Exemplary nested subranges of (B) include but are not limited to, from about 0.1% to about 99.9% of (B); from about 0.5% to about 99.5% of (B); from about 1.0% to about 99.0% of (B); from about 1.5% to about 98.5 % of (B); from about 2.0% to about 98.0 % of (B); from about 2.5% to about 97.5% of (B); from about 3.0% to about 97.0% of (B); from about 5.0% to about 95.0% of (B); from about 7.5% to about 92.5% of (B); from about 10.0% to about 90.0% of (B); from about 12.5% to about 87.5% of (B); from about 15.0% to about 85.0% of (B); from about 17.5% to about 87.5% of (B); from about 20.0% to about 80.0% of (B); from about 22.5% to about 75.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 30.0% to about 70.0% of (B); from about 32.5% to about 67.5 % of (B); from about 35.0% to about 65.0% of (B); from about 37.5% to about.62.5% of (B); from about 40.0% to about.60.0% of (B); from about 42.5% to about 57.5% of (B); from about 45.0% to about 55.0% of (B) and from about 47.5% to about 52.5% of (B).

[0111] In certain of these embodiments, the ranges of (B) of the metal working fluid composition, based on the total % of (B), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0112] In one non-limiting embodiment of the present disclosure, the reaction product comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a base comprises one or more structures selected from the group consisting of the following structures:and combinations thereof.

[0113] In one non-limiting embodiment, the present invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a base.; and (B) from about 1 .0 % to about 99.99% one or more metal working fluid additive(s).

[0114] In certain of these embodiments, the suitable ranges of (A) (that is, the maleated natural oil and a base) of the metal working fluid composition can include discrete subranges, such as nested subranges. Exemplary nested subranges include but are not limited to, from about 0.01% to about 20% of (A); from about 0.05 % to about 20 % of (A); from about 0.10% to about 20% of (A); from about 0.50% to about 20% of (A); from about 1.0% to about 20% of (A); from about 2.5% to about 20% of (A); from about 2.5% to about 20% of (A); from about 5.0% to about 20% of (A); from about 7.5% to about 20% of (A); from about 10% to about 20% of (A); from about 12.5% to about 20% of (A); from about 15% to about 20 of (A); from about 17.5% to about 20% of (A); from about 0.01% to about 17.5% of (A); from about 0.01% to about 15% of(A); from about 0.01% to about 12.5% of (A); from about 0.01% to about 10% of (A); from about 0.01% to about 7.5% of (A); from about 0.01% to about 5% of (A); from about 0.01% to about 2.5% of (A); from about 0.01% to about 2.0% of (A); from about 0.01% to about 1.0% of (A); from about 0.01% to about 0.05% of (A); and from about 0.01% to about 0.05% of (A).

[0115] In certain of these embodiments, the ranges of (A) of the metal working fluid composition, based on the total % of (A), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art mightinclude such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0116] In certain of these embodiments, the suitable ranges of (B) (that is, the one or more metal working fluid additive(s)) include discrete subranges, such as nested subranges. Exemplary nested subranges of (B) include but are not limited to, from about 0.1% to about 99.9% of (B); from about 0.5% to about 99.5% of (B); from about 1.0% to about 99.0% of (B); from about 1.5% to about 98.5 % of (B); from about 2.0% to about 98.0 % of (B); from about 2.5% to about 97.5% of (B); from about 3.0% to about 97.0% of (B); from about 5.0% to about 95.0% of (B); from about 7.5% to about 92.5% of (B); from about 10.0% to about 90.0% of (B); from about 12.5% to about 87.5% of (B); from about 15.0% to about 85.0% of (B); from about 17.5% to about 87.5% of (B); from about 20.0% to about 80.0% of (B); from about 22.5% to about 75.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 30.0% to about 70.0% of (B); from about 32.5% to about 67.5 % of (B); from about 35.0% to about 65.0% of (B); from about 37.5% to about.62.5% of (B); from about 40.0% to about.60.0% of (B); from about 42.5% to about 57.5% of (B); from about 45.0% to about 55.0% of (B) and from about 47.5% to about 52.5% of (B).

[0117] In certain of these embodiments, the ranges of (B) of the metal working fluid composition, based on the total % of (B), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0118] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base; wherein the reaction product comprises the structure:wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ! Mg, i Ca, ! Co, ! Cu, i Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

[0119] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising (A) a reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base, wherein the reaction product comprises one or more structure selected from the group of the following structures:wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-l -hexyl, 2-butyl-l-octyl, 2-hexyl-l -decyl, 2-octyl- 1 -dodecyl, or mixtures thereof; and wherein R1, R2and R3are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

[0120] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising a reaction product is a polymer of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (C) a base, wherein the reaction product is a polymer represented by the structure:wherein n is greater than 1; wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties, with or without heteroatoms, containing from about 1 to about 36 carbon atoms; wherein R4is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, alkenylene, arylene and alkarylene moieties,with or without heteroatoms, containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, 14 Mg, 14 Ca, 14 Co, 14 Cu, 14 Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkyl ammonium .

[0121] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (C) a base, wherein the reaction product is a polymer comprising a structure selected from the following group of structures:wherein 1 < n < 30; wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-l -hexyl, 2-butyl-l -octyl, 2- hexyl-1 -decyl, 2-octyl-l -dodecyl, or mixtures thereof; wherein R1, R2and R3are each,independently, hydrogen, methyl, or an unsubstituted or substituted alkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R4is -CH2CH2CH2-,or a mixture thereof.

[0122] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0123] In certain of these embodiments, the suitable ranges of (A) (that is, the maleated natural oil and a functionalized or unfunctionalized moiety) of the metal working fluid composition can include discrete subranges, such as nested subranges. Exemplary nested subranges include but are not limited to, from about 0.01% to about 20% of (A); from about 0.05 % to about 20 % of (A); from about 0.10% to about 20% of (A); from about 0.50% to about 20% of (A); from about 1.0% to about 20% of (A); from about 2.5% to about 20% of (A); from about 2.5% to about 20% of (A); from about 5.0% to about 20% of (A); from about 7.5% to about 20% of (A); from about 10% to about 20% of (A); from about 12.5% to about 20% of (A); from about 15% to about 20 of (A); from about 17.5% to about 20% of (A); from about 0.01% to about 17.5% of (A); from about 0.01% to about 15% of(A); from about 0.01% to about 12.5% of (A); from about 0.01% to about 10% of (A); from about 0.01% to about 7.5% of (A); from about 0.01% to about 5% of (A); from about 0.01% to about 2.5% of (A); from about 0.01% to about 2.0% of (A); from about 0.01% to about 1 .0% of (A); from about 0.01% to about 0.05% of (A); and from about 0.01% to about 0.05% of (A).

[0124] In certain of these embodiments, the ranges of (A) of the metal working fluid composition, based on the total % of (A), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0125] In certain of these embodiments, the suitable ranges of (B) (that is, the one or more metal working fluid additive(s)) include discrete subranges, such as nested subranges. Exemplary nested subranges of (B) include but are not limited to, from about 0.1% to about 99.9% of (B); from about 0.5% to about 99.5% of (B); from about 1 .0% to about 99.0% of (B); from about 1.5% to about 98.5 % of (B); from about 2.0% to about 98.0 % of (B); from about 2.5% to about 97.5% of (B); from about 3.0% to about 97.0% of (B); from about 5.0% to about 95.0% of (B); from about 7.5% to about 92.5% of (B); from about 10.0% to about 90.0% of (B); from about 12.5% to about 87.5% of (B); from about 15.0% to about 85.0% of (B); from about 17.5% to about 87.5% of (B); from about 20.0% to about 80.0% of (B); from about 22.5% to about 75.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 30.0% to about 70.0% of (B); from about 32.5% to about 67.5 % of (B); from about 35.0% to about 65.0% of (B); from about 37.5% to about.62.5% of (B); from about 40.0% to about.60.0% of (B); from about 42.5% to about 57.5% of (B); from about 45.0% to about 55.0% of (B) and from about 47.5% to about 52.5% of (B).

[0126] In certain of these embodiments, the ranges of (B) of the metal working fluid composition, based on the total % of (B), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0127] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% reaction product having a polymer of (a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) afunctionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (c) a base; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0128] In certain of these embodiments, the suitable ranges of (A) (that is, the maleated natural oil and a functionalized or unfunctionalized moiety) of the metal working fluid composition can include discrete subranges, such as nested subranges. Exemplary nested subranges include but are not limited to, from about 0.01% to about 20% of (A); from about 0.05 % to about 20 % of (A); from about 0.10% to about 20% of (A); from about 0.50% to about 20% of (A); from about 1.0% to about 20% of (A); from about 2.5% to about 20% of (A); from about 2.5% to about 20% of (A); from about 5.0% to about 20% of (A); from about 7.5% to about 20% of (A); from about 10% to about 20% of (A); from about 12.5% to about 20% of (A); from about 15% to about 20 of (A); from about 17.5% to about 20% of (A); from about 0.01% to about 17.5% of (A); from about 0.01% to about 15% of(A); from about 0.01% to about 12.5% of (A); from about 0.01% to about 10% of (A); from about 0.01% to about 7.5% of (A); from about 0.01% to about 5% of (A); from about 0.01% to about 2.5% of (A); from about 0.01% to about 2.0% of (A); from about 0.01% to about 1.0% of (A); from about 0.01% to about 0.05% of (A); and from about 0.01% to about 0.05% of (A).

[0129] In certain of these embodiments, the ranges of (A) of the metal working fluid composition, based on the total % of (A), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0130] In certain of these embodiments, the suitable ranges of (B) (that is, the one or more metal working fluid additive(s)) include discrete subranges, such as nested subranges. Exemplary nested subranges of (B) include but are not limited to, from about 0.1% to about 99.9% of (B); from about 0.5% to about 99.5% of (B); from about 1.0% to about 99.0% of (B); from about 1.5% to about 98.5 % of (B); from about 2.0% to about 98.0 % of (B); from about 2.5% to about 97.5% of (B); from about 3.0% to about 97.0% of (B); from about 5.0% to about 95.0% of (B); fromabout 7.5% to about 92.5% of (B); from about 10.0% to about 90.0% of (B); from about 12.5% to about 87.5% of (B); from about 15.0% to about 85.0% of (B); from about 17.5% to about 87.5% of (B); from about 20.0% to about 80.0% of (B); from about 22.5% to about 75.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 30.0% to about 70.0% of (B); from about 32.5% to about 67.5 % of (B); from about 35.0% to about 65.0% of (B); from about 37.5% to about.62.5% of (B); from about 40.0% to about.60.0% of (B); from about 42.5% to about 57.5% of (B); from about 45.0% to about 55.0% of (B) and from about 47.5% to about 52.5% of (B).

[0131] In certain of these embodiments, the ranges of (B) of the metal working fluid composition, based on the total % of (B), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0132] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising a reaction product of (a) a maleated natural oil with maleated functionality; (b) a base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the reaction product comprises one or more structure selected from the following group of structures:combinations thereof, wherein R is ethyl, butyl, hexyl, octyl, 2-ethylhex-l-yl, 2-butyloct-l-yl, 2-hexyldec-l-yl, 2-octyldodec-l-yl or mixtures thereof.

[0133] In one non-limiting embodiment, the invention provides a metal working fluid composition comprising (A) from about 0.01% to about 20.0% reaction product of (a) a maleated natural oil, comprising a natural oil with maleated functionality; (b) a base; wherein the maleated functionality has been partially reacted with the base; and (c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0134] In certain of these embodiments, the suitable ranges of (A) (that is, the maleated natural oil and a base) of the metal working fluid composition can include discrete subranges, such as nested subranges. Exemplary nested subranges include but are not limited to, from about 0.01% to about 20% of (A); from about 0.05 % to about 20 % of (A); from about 0.10% to about 20% of(A); from about 0.50% to about 20% of (A); from about 1.0% to about 20% of (A); from about 2.5% to about 20% of (A); from about 2.5% to about 20% of (A); from about 5.0% to about 20% of (A); from about 7.5% to about 20% of (A); from about 10% to about 20% of (A); from about 12.5% to about 20% of (A); from about 15% to about 20 of (A); from about 17.5% to about 20% of (A); from about 0.01% to about 17.5% of (A); from about 0.01% to about 15% of(A); from about 0.01% to about 12.5% of (A); from about 0.01% to about 10% of (A); from about 0.01% to about 7.5% of (A); from about 0.01% to about 5% of (A); from about 0.01% to about 2.5% of (A); from about 0.01% to about 2.0% of (A); from about 0.01% to about 1.0% of (A); from about 0.01% to about 0.05% of (A); and from about 0.01% to about 0.05% of (A).

[0135] In certain of these embodiments, the ranges of (A) of the metal working fluid composition, based on the total % of (A), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0136] In certain of these embodiments, the suitable ranges of (B) (that is, the one or more metal working fluid additive(s)) include discrete subranges, such as nested subranges. Exemplary nested subranges of (B) include but are not limited to, from about 0.1% to about 99.9% of (B); from about 0.5% to about 99.5% of (B); from about 1 .0% to about 99.0% of (B); from about 1.5% to about 98.5 % of (B); from about 2.0% to about 98.0 % of (B); from about 2.5% to about 97.5% of (B); from about 3.0% to about 97.0% of (B); from about 5.0% to about 95.0% of (B); from about 7.5% to about 92.5% of (B); from about 10.0% to about 90.0% of (B); from about 12.5% to about 87.5% of (B); from about 15.0% to about 85.0% of (B); from about 17.5% to about 87.5% of (B); from about 20.0% to about 80.0% of (B); from about 22.5% to about 75.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 25.0% to about 75.0% of (B); from about 27.5% to about 72.5% of (B); from about 30.0% to about 70.0% of (B); from about 32.5% to about 67.5 % of (B); from about 35.0% to about 65.0% of (B); from about 37.5% to about.62.5% of (B); from about 40.0% to about.60.0% of (B); from about 42.5% to about 57.5% of (B); from about 45.0% to about 55.0% of (B) and from about 47.5% to about 52.5% of (B).

[0137] In certain of these embodiments, the ranges of (B) of the metal working fluid composition, based on the total % of (B), can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0138] In some embodiments of the present invention, the suitable range of the reaction product of metal working fluid 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.%; from about 5 wt.% to about 10 wt.%; from about 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.% based on the total weight of the metal working fluid composition.

[0139] In certain embodiments, the suitable ranges of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition can include discrete subranges, such as nested subranges. Exemplary nested subranges include but are not limited to, from about 0.01 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.05 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.10 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.50 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 1.0 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 2.5 wt % to about 20% of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 2.5 wt % to about 20% of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 5.0 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 7.5 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 10 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluidcomposition; from about 12.5 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 15 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 17.5 wt. % to about 20 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 17.5 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 15 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 12.5 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 10 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 7.5 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 5 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 2.5 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 2.0 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 1.0 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition; from about 0.01 wt. % to about 0.05 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition and from about 0.01 wt. % to about 0.05 wt. % of the reaction product of metal working fluid composition based on the total weight of the metal working fluid composition.

[0140] In certain embodiments, the ranges of the reaction product of a metal working fluid composition, based on the total weight of the composition, can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are meant to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0141] In another non-limiting embodiment of the present disclosure, the metal working fluid composition can further comprises at least metal working fluid additive(s) in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.99 wt.%, based on the total weight of the metal working fluid composition.

[0142] In certain embodiments, the suitable ranges of the least metal working fluid additive(s) can include discrete subranges, such as nested subranges. Exemplary nested subranges include but are not limited to, from about 0.1 wt. % to about 99.9 wt. % of the least metal working fluid additive(s); from about 0.5 wt. % to about 99.5 wt. % of the least metal working fluid additive(s); from about 1.0 wt. % to about 99.0 wt. % of the least metal working fluid additive(s); from about1.5 wt. % to about 98.5 wt. % of the least metal working fluid additive(s); from about 2.0 wt. % to about 98.0 wt. % of the least metal working fluid additive(s); from about 2.5 wt. % to about 97.5 wt. % of the least metal working fluid additive(s); from about 3.0 wt. % to about 97.0 wt. % of the least metal working fluid additive(s); from about 5.0 wt. % to about 95.0 wt. % of the least metal working fluid additive(s); from about 7.5 wt. % to about 92.5 wt. % of the least metal working fluid additive(s); from about 10.0 wt. % to about 90.0 wt. % of the least metal working fluid additive(s); from about 12.5 wt. % to about 87.5 wt. % of the least metal working fluid additive(s); from about 15.0 wt. % to about 85.0 wt. % of the least metal working fluid additive(s); from about17.5 wt. % to about 87.5 wt. % of the least metal working fluid additive(s); from about 20.0 wt. % to about 80.0 wt. % of the least metal working fluid additive(s); from about 22.5 wt. % to about75.5 wt. % of the least metal working fluid additive(s); from about 25.0 wt. % to about 75.0 wt. % of the least metal working fluid additive(s); from about 27.5 wt. % to about 72.5 wt. % of the least metal working fluid additive(s); from about 25.0 wt. % to about 75.0 wt. % of the least metal working fluid additive(s); from about 27.5 wt. % to about 72.5 wt. % of the least metal workingfluid additive(s); from about 30.0 wt. % to about 70.0 wt. % of the least metal working fluid additive(s); from about 32.5 wt. % to about 67.5 wt. % of the least metal working fluid additive(s); from about 35.0 wt. % to about 65.0 wt. % of the least metal working fluid additive(s); from about37.5 wt. % to about.62.5 wt. % of the least metal working fluid additive(s); from about 40.0 wt. % to about.60.0 wt. % of the least metal working fluid additive(s); from about 42.5 wt. % to about57.5 wt. % of the least metal working fluid additive(s); from about 45.0 wt. % to about 55.0 wt. % of the least metal working fluid additive(s); and from about 47.5 wt. % to about 52.5 wt. % of the least metal working fluid additive(s).

[0143] In certain embodiments, the ranges of the least metal working fluid additive(s) can include specific subranges, such as bifurcated subranges. These bifurcated subranges exclude certain ranges from coverage. The prior art might include such ranges that the inventors were not previously aware of. In the nested discrete subranges described above, these bifurcated subranges are intended to exclude particular ranges, as one of ordinary skill in the art would understand from the Applicant’s disclosure.

[0144] In some embodiments of the present invention, the metallic materials from which the metal working apparatus and articles to be fabricated are made, include steel, cast iron, and ferrous alloys, as well as aluminum alloys and other non-ferrous alloys, including such components as titanium, magnesium, copper, tin, and brass.

[0145] In some embodiments of the present invention, suitable examples of metal deactivators include but not limited to imidazolines, pyrimidine derivatives, alkylthiadiazoles, mercaptobenzothiazoles, benzotriazoles, 1, 3, 4-thiadiazolepoly sulfide, l,3,4-thiadiazolyl-2,5- bisdialkyldithiocarbamates, 2-(alkyldithio)benzoimidazoles, P-(o- carboxybenzylthio)propionitrile, and tolytriazole and derivatives thereof.

[0146] In some embodiments of the present invention, suitable lubricants consist essentially of water, oleic Acid, a complex organic phosphate ester, an amine, a polyoxyalkylated animal or vegetable oil product, one or more polyol and / or polyalkylene glycol esters and a polyalkylene glycol polymer.

[0147] In another embodiment, the emulsifying and / or dispersing compound is selected from the group of non-ionic, anionic and zwitterionic surfactants consisting of alkyl alcohols, alkylphenols, alkanoic acids, fatty acids, fatty alcohol alkoxy late, ether, oleyl alcohol polyglycol ether, Sodium alkyl aryl sulfonate, carboxylates and / or other organic acid, block and random copolymers, alkyl polyglucosides anionic surfactants having at least one sulfate or sulfonate group, ether sulfates, ether phosphates, phosphate esters, monoglycerides, fatty amines sorbitan and its derivatives, and, succinic acid and its derivatives.

[0148] In another embodiment, the present application further comprises suitable coupling agent selected from the group consisting of propylene glycol, polyethylene glycol esters, glyceryl oleates, glyceryl monooleate, hydrophobic glycol ether, sorbitan oleates, fatty alkanol amides and combinations.

[0149] In another embodiment of the present application further comprises anti-wear additive can be selected from the group consisting of zinc dialkyl or diaryl dithiophosphates; triaryl phosphates; trialkyl phosphates; polymeric nitrogen / phosphorous compounds made, for example, by reacting a dialkoxy amine with a substituted organic phosphate; amine phosphates; triphenyl phosphorothi onate and dihydrocarbyl dithiophosphate metals salts.

[0150] In another embodiment of the present application, further comprises antimicrobial compound(s) possess anti-bacterial, antifungal, anti-algal or other antimicrobial activity includes but not limited to phenylphenol, morpholine, omadine, and pyrithione.

[0151] Suitable extreme pressure agents include but not limited to chlorinated paraffins, chlorinated waxes, chlorinated esters, chlorinated fatty acids; sulfurized fats; sulfurized olefins; polysulfides; sulfur-chlorinated compounds; sulfurized sulfonates; phosphate esters; phosphate fatty acids; phosphate amines, and combinations thereof.

[0152] In another embodiment, the present application, further comprises antifriction agent include but not limited to neopentyl glycol dioleate, trimethylolpropane trioleate, pentaerythritol tetraoleate, propylene glycol dioleate, ricinoleic acid condensate, and methyl ester of oils, and combinations thereof and polymeric substances include polyethylene glycols, acrylic acids, and polyvinylpyrolidones,

[0153] Suitable bactericides include but not limited to thiazoline, pyridine, morpholine, phenol, nitro- and IPBC-based preservatives.

[0154] In another embodiment, the present application, chelating agents includes ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTPA), nitrilotri acetic acid (NTA), iminodiacetic acid (IDA), iminotriacetic acid (ITA), ethylenediamine (En), N,N'-diethylenediamine (Den), diethylenetriamine (DTN), di ethylenetetramine (Trien), triaminotriethylene amine, propylenediamine, glycolic acid, hydroxybutyric acid, salicylic acid, benzoic acid, mixtures thereof.

[0155] In another embodiment, the present application, pH regulators include monoethanol amine, diethanol amine, triethanol amine, monoisopropanolamine, diisopropanol amine, triisopropanol amine, aminomethyl propanol, diglycol amine, diglycolamine 2-(2- aminoethoxy)ethanol (DGA), or a combination thereof.

[0156] In another embodiment, the present application, the base oil can be added to metal working fluid composition. Preferably the base oil is a base oil selected from naphthenic oils, paraffinic oils or ester oils, or combinations thereof.

[0157] The metal working fluid composition can also contain additional materials such as, solvents, liquid carriers, solid carriers or fillers, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, compatibilizers, anti-freezing agents, crystallization inhibitors, clarifiers, stabilizers, and mixtures as appropriate.

[0158] In another embodiment, the present invention provides a metal working fluid composition used for protection of tool against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion, increased operational efficiency, longer tool life, chip removal from the processing zone, excellent cooling and lubrication properties, thermal stability, improved surface finish, enhanced fluid life, foam and soap reduction, lower energy consumption and lower total cost of operations.

[0159] One more embodiment of the present invention is to provide a method for preparing metal working fluid composition, wherein the method comprises the following steps: (a) mixing a reaction product (A) maleated natural oil; a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moi eties, hydrophilic moi eties; a base and combinations thereof of the invention with water, amines and an emulsifier and the mixture was mixed under stirring thoroughly, obtaining the first mixed material (1); (b) then the obtained mixture (1) ismixed with coupling agent, lubrication additive, and bactericide to obtain second mixture (2); (c) adding base oil, and optionally adding any other additional metal working fluid additive to the second mixture (2) to obtain the third mixture of (3); and (d) adding a antifoaming agent to the third mixture (3) by stirring and mixing, to result the metal working fluid.

[0160] Another embodiment of the present invention is to provide method for preparing metal working fluid composition wherein the step (a) the stirring of the stirring speed is preferably 400 to 800rpm or until a vortex appears, step (a) the stirring time is preferably 10 to 20 min; step (a), the stirring temperature is 25-40 degrees centigrade, preferably, step (2) the stirring of the stirring speed is preferably 400 to 800rpm, or until a vortex appears;, the stirring time in the step (b) is 10 - 20 min; step (b), the stirring temperature is 25-40 degrees centigrade, step (c) the stirring of the stirring speed 400 to 800rpm, or until a vortex appears;, the stirring time in the step (c) 10 to 20min;, step (c), the stirring temperature is 25-40 degrees centigrade.

[0161] 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.

[0162] 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

[0163] Example A; Grafting of maleic anhydride onto natural oils.

[0164] Example Al: Grafting of maleic anhydride onto soybean oil.

[0165] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 600 g of soybean oil (SBO) and 204 g (3 mole equivalents based on SBO) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 6-8hours. Completion of the reaction was indicated by NMR, and LC indicated <0.5% of residual maleic anhydride.

[0166] Example A2; Grafting of maleic anhydride onto palm oil.

[0167] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of palm oil and 23 g (2 mole equivalents based on palm oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%.

[0168] Example A3: Grafting of maleic anhydride onto canola oil.

[0169] 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%.

[0170] Example A4: Grafting of maleic anhydride onto sunflower oil.

[0171] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of sunflower oil and 22.4 g (2 mole equivalents based on palm oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%.

[0172] Example A5: Grafting of maleic anhydride onto castor oil.

[0173] 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%.

[0174] Example A6; Grafting of maleic anhydride onto chickpea oil

[0175] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter and mechanical stirrer was charged with 100 g of chickpea oil and 38 g (3.4 mole equivalents relative to chickpea oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 10-14 hours. The amber, viscous product was characterized by NMR, and LC indicated <0.5% of residual maleic anhydride. Yield of maleated chickpea oil was >96%.

[0176] Example A7; Grafting of maleic anhydride onto clary sage oil

[0177] 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%.

[0178] Example B: Grafting of hydrophobic alcohol onto natural oils having grafted maleic anhydride.

[0179] Example Bl :

[0180] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example Al and 30.5 g (1 mole eq.) of 2-octyl-l -dodecanol were mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0181] Example B2:

[0182] In a 1 - Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A2 and 55.64 g (2 mole eq.) of 2-octyl-l -dodecanol were mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0183] Example B3:

[0184] In a 1 - Liter , 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A2 and 61.20 g (2.2 mole eq.) of 2-octyl-l -dodecanol were mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product which was characterized by NMR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0185] Example B4:

[0186] In a 1 - Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A3 and 25.44 g (1 mole eq.) of 2-octyl-l -dodecanol were mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0187] Example B5:

[0188] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A3 and 31.81 g (1.25 mole eq.) of 2-octyl-l -dodecanol were mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0189] Example B6:

[0190] In a 1 - Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A3 and 38. 17 g (1.5 mole eq.) of 2-octyl-l -dodecanol were mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0191] Example B7:

[0192] In a 1 - Liter , 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A 3 and 50.89 g (2 mole eq.) of 2-octyl-l -dodecanol were mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0193] Example B8:

[0194] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A3 and 63.61 g (2.5 mole eq.) of 2-octyl-l -dodecanol were mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0195] Example B9:

[0196] In a 1 - Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A4 and 35 g (1 mole eq.) of 2-octyl-l -dodecanol was mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0197] Example B10:

[0198] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A5 and 35 g (1 mole eq.) of 2-octyl-l -dodecanol was mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0199] Example Bl 1 :

[0200] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A6 and 35 g (1 mole eq.) of 2-octyl-l -dodecanol was mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0201] Example B12:

[0202] In a 1 - Liter , 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A7 and 35 g (1 mole eq.) of 2-octyl-l -dodecanol was mixed and heated to 90 °C and held for 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product, which was characterized by NMR, IR, GC (<5% residual 2-octyl-l -dodecanol) and LC (<1% residual maleic anhydride).

[0203] Example B13:

[0204] In a 1 -Liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A3 was heated to 85 °C with stirring, charged with 1.2 mole equivalent of 2-ethyl-l- hexanol, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0205] Example B 14:

[0206] In a 1 -Liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A3 was heated to 85 °C with stirring, charged with 2.0 mole equivalents of 2-ethyLl- hexanol, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0207] Example Bl 5:

[0208] In a 1 -Liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A3 was heated to 85 °C with stirring, charged with 1.2 mole equivalent of behenyl alcohol, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0209] Example B16:

[0210] In a 1 -Liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of amber color viscous product from maleation reaction Example A3 was heated to 85 °C with stirring, charged with 2.0 mole equivalents of behenyl alcohol, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0211] Example C: Grafting of hydrophilic polyol, hydrophilic alcohol or hydrophobic polyol onto natural oils having grafted maleic anhydride and grafted hydrophobic alcohol.

[0212] Example Cl :

[0213] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B6 and 5.7 g (1 mole eq.) of glycerin were mixed and heated to 90 °C and held for 4 to 6 hours. The one potreaction without catalyst and solvent yields >96% amber color viscous product which was characterized by NMR and LC (<0.05% residual maleic anhydride).

[0214] Example C2:

[0215] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B4 and 6.28 g (1 mole eq.) of glycerin were mixed and heated to 90 °C and held for 4 to 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product which was characterized by NMR and LC (<0.05% residual maleic anhydride).

[0216] Example C3 :

[0217] In a 1 - Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B4 and 9.42 g (1.5 mole eq.) of glycerin were mixed and heated to 90 °C and held for 4 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product which was characterized by NMR and LC (<0.05% residual maleic anhydride).

[0218] Example C4:

[0219] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B9 and 11 g (1 mole eq.) of glycerin was mixed and heated to 90 °C and held for 4 to 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product which was characterized by NMR and LC (<0.05% residual maleic anhydride).

[0220] Example C5:

[0221] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B10 and 11 g (1 mole eq.) of glycerin was mixed and heated to 90 °C and held for 4 to 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product which was characterized by NMR and LC (<0.05% residual maleic anhydride).

[0222] Example C6:

[0223] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B 11 and 11 g (1 mole eq.) of glycerin was mixed and heated to 90 °C and held for 4 to 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product which was characterized by NMR and LC (<0.05% residual maleic anhydride).

[0224] Example C7:

[0225] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B 12 and 11 g (1 mole eq.) of glycerin was mixed and heated to 90 °C and held for 4 to 6 hours. The one pot reaction without catalyst and solvent yields >96% amber color viscous product which was characterized by NMR and LC (<0.05% residual maleic anhydride).

[0226] Example C8:

[0227] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 152 g of amber color viscous product from Example B4 and 4.74 g (1 mole eq.) of ethanol were mixed and heated to 90 °C and held for 8 hours. The one pot reaction without catalyst and solvent yields >96% amber color product which was characterized by NMR and LC (<0.05% residual maleic anhydride).

[0228] Example C9:

[0229] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 152 g of amber color viscous product from Example B4 and 9.47 g (2 mole eq.) of ethanol were mixed and heated to 90 °C and held for 8 hours. The one pot reaction without catalyst and solvent yields >96% amber color product which was characterized by NMR and LC (<0.05% residual maleic anhydride).

[0230] Example CIO:

[0231] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B13 was heated to 85 °C with stirring, charged with 1 mole equivalent of castor oil, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0232] Example Cl 1 :

[0233] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B13 was heated to 85 °C with stirring, charged with 0.5 mole equivalent of glycerin and 0.5 mole equivalent of castor oil, all at once, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0234] Example C12:

[0235] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B14 was heated to 85 °C with stirring, charged with 1 mole equivalent of castor oil, and held at 85 °C for 6to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0236] Example C13:

[0237] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B14 was heated to 85 °C with stirring, charged with 0.5 mole equivalent of glycerin and 0.5 mole equivalent of castor oil, all at once, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0238] Example C14:

[0239] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B15 was heated to 85 °C with stirring, charged with 1 mole equivalent of castor oil, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0240] Example Cl 5:

[0241] In a 1 - Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example Bl 5 was heated to 85 °C with stirring, charged with 0.5 mole equivalent of glycerin and 0.5 mole equivalent of castor oil, all at once, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0242] Example Cl 6:

[0243] In a 1- Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B16 was heated to 85 °C with stirring, charged with 1 mole equivalent of castor oil, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0244] Example Cl 7:

[0245] In a 1 - Liter, 4-neck kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter, and a mechanical stirrer, 100 g of amber color viscous product from Example B16 was heated to 85 °C with stirring, charged with 0.5 mole equivalent of glycerin and 0.5 mole equivalent of castor oil, all at once, and held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. Yield of the liquid product was >98 %.

[0246] Example S: Salts of Maleated natural oils

[0247] Example SI; Sodium salt of maleated soybean oil from aqueous sodium hydroxideIn a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of product from maleation reaction A 1 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%.

[0248] Example S2; Sodium salt of maleated palm oil from aqueous sodium hydroxideIn a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction A2 was heated to 90 °C, and a mixture of 18.04 g (2 mole equivalents based on palm oil) of 50% aqueous sodium hydroxide and 45 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.

[0249] Example S3; Sodium salt of maleated canola oil from aqueous sodium hydroxide

[0250] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction A3 was heated to 90 °C, and a mixture of 18.25 g (2 mole equivalents based on canola oil) of 50% aqueous sodium hydroxide and 45 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.

[0251] Example S4 ; Sodium salt of maleated sunflower oil from aqueous sodium hydroxide

[0252] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction A4 was heated to 90 °C, and a mixture of 18.26 g (2 mole equivalents based on sunflower oil) of 50% aqueous sodium hydroxide and 45 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.

[0253] Example S5: Sodium salt of maleated castor oil from aqueous sodium hydroxide

[0254] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction A5 was heated to 90 °C, and a mixture of 17.15 g (2 mole equivalents based on castor oil) of 50% aqueous sodium hydroxide and 45 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.

[0255] Example S6 : Sodium salt of maleated soybean oil from sodium carbonate

[0256] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of product from maleation reaction Al 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%.

[0257] Example D : Sodium calcium salt of maleated natural oil

[0258] Example DI: Sodium calcium salt of maleated soybean oil from calcium carbonate and sodium carbonate (7:3 ratio)

[0259] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of product from maleation reaction Al was heated to 90 °C, and a mixture of 8.36 g (0.9 mole equivalents based on soybean oil) of sodium carbonate and 17.8 g (2.1 mole equivalents based on soybean oil) of calcium carbonate dissolved in 85 g of water was added over 3 hours, controlling the foam formation. The reaction was held at 90 °C for 3 hours. The product contained 60 weight % solids and was characterized by IR. Yield was >96%.

[0260] Example D2: Sodium calcium salt of maleated palm oil from calcium carbonate and sodium carbonate (7:3 ratio)

[0261] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 122 g of product from maleation reaction A2 was heated to 90 °C, and a mixture of 11.55 g (0.9 mole equivalents based on palm oil) of sodium carbonate and 24.6 g (2.1 mole equivalents based on palm oil) of calcium carbonate dissolved in 122 g of water was added over 3 hours, controlling the foam formation. The reaction was held at 90 °C for 3 hours. The product contained 60 weight % solids and was characterized by IR. Yield was >96%.

[0262] Example D3: Sodium calcium salt of maleated canola oil from calcium carbonate and sodium carbonate (7:3 ratio)

[0263] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 122 g of product from maleation reaction A3 was heated to 90 °C, and a mixture of 11.3 g (0.9 mole equivalents based on canola oil) of sodium carbonate and 24 g (2.1 mole equivalents based on canola oil) of calcium carbonate dissolved in 122 g of water was added over 3 hours, controlling the foam formation. The reaction was held at 90 °C for 3 hours. The product contained 60 weight % solids and was characterized by IR. Yield was >96%.

[0264] Example D4: Sodium calcium salt of maleated sunflower oil from calcium carbonate and sodium carbonate (7:3 ratio)In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 122 g of product from maleation reaction A4 was heated to 90 °C, and a mixture of 11.55 g (0.9 mole equivalents based on sunflower oil) of sodium carbonate and 24.6 g (2.1 mole equivalents based on sunflower oil) of calcium carbonate dissolved in 122 g of water was added over 3 hours, controlling the foam formation. The reaction was held at 90 °C for 3 hours. The product contained 60 weight % solids and was characterized by IR. Yield was >96%.

[0265] Example D5: Sodium calcium salt of maleated castor oil from calcium carbonate and sodium carbonate (7:3 ratio)In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 122 g of product from maleation reaction A5 was heated to 90 °C, and a mixture of 10.6 g (0.9 mole equivalents based on castor oil) of sodium carbonate and 22.5 g (2.1 moleequivalents based on castor oil of calcium carbonate dissolved in 122 g of water was added over 3 hours, controlling the foam formation. The reaction was held at 90 °C for 3 hours. The product contained 60 weight % solids and was characterized by IR. Yield was >96%.

[0266] Example El: Calcium salt of maleated soybean oil from calcium carbonateIn a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of product from maleation reaction Al was heated to 90 °C, and a solution of 25.5 g (3 mole equivalents based on soybean oil) of calcium carbonate in 85 g of water was added over 3 hours, controlling the foam formation. The reaction was held at 90 °C for 3 hours. The product contained 60 weight % solids and was characterized by IR. Yield was >96%.

[0267] Example Fl: Sodium salt of maleated soybean oil from aqueous sodium hydroxide

[0268] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of product from maleation reaction Al 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%.

[0269] Example Gl: Sodium salt of maleated soybean oil reacted with hydrophobic 2-octyl- 1 -dodecanol and hydrophilic glycerol

[0270] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of maleated soybean oil, produced as in Example Al, and 38.17 g (1.5 mole equivalents, relative to maleated soybean oil) of 2-octyl-l -dodecanol, and the mixture was heated at 90 °C for 6 hours. Glycerol (7.85 g, 1 mole equivalent, relative to maleated soybean oil) was added, and the mixture was heated at 90 °C for another 6 hours. The reaction mixture was cooled to 85 °C, and 5.1 (0.75 mole equivalent, relative to maleated soybean oil) of 50 wt% sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 3 hours.

[0271] Example G2: Sodium salt of maleated soybean oil reacted with hydrophilic glycerol

[0272] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 198 g of maleated soybean oil, produced as in Example Al, and 4.71 g (0.3 mole equivalent relative to maleated soybean oil) of glycerol were combined, heated to 40 °C and held at 40 °C for 2 hours. The amber liquid product was characterized by NMR and IR. Aqueous sodium hydroxide (50%, 13.64 g, 2.0 mole equivalents) was added over 30 minutes, and the mixture was held at 40 °C for 2 hours. Water was added to the viscous mixture to obtain 60% solids solution. The amber liquid product was characterized by NMR and IR. Yield was >98%.

[0273] Example G3: Sodium salt of maleated soybean oil reacted with hydrophobic castor oil

[0274] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 100 g of maleated soybean oil, produced as in Example Al, and 32.8 g (0.4 mole equivalent relative to maleated soybean oil) of castor oil were combined, heated to 80 °C and held at 80 °C for 2-6 hours. The amber, viscous, crosslinked product was characterized by NMR and IR, and GC indicated <5% of residual castor oil. Yield of maleated soybean oil reacted with castor oil was >96%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 100 g of the maleated soybean oil reacted with castor oil was 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 amber liquid product was characterized by NMR and IR. Yield of the sodium salt of maleated soybean oil reacted with castor oil was >98%.

[0275] Example G4: Sodium salt of maleated soybean oil reacted with lysine

[0276] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 150 g of maleated soybean oil, produced as in Example Al, and 5.73 g (0.5 mole equivalent relative to maleated soybean oil) of lysine were combined, heated to 100 °C and held at 100 °C for 8 hours. The amber, viscous, crosslinked product was characterized by NMR and IR. The mixture was cooled to 50 °C. Water and 30.3 g of 50% aqueous sodium hydroxide were added over 60 minutes to create a final solution that was 50 weight % solids, and the mixture was held at 50 °C for 4 hours. The amber liquid product was characterized by NMR and IR. Yield of sodium salt of maleated soybean oil reacted with lysine was >98%.

[0277] Example G5; Sodium salt of maleated soybean oil reacted with 1 equivalent of diethanolamine

[0278] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 150 g of maleated soybean oil, produced as in Example Al, and 150 g of water were heated to 90 °C for 2 h. The mixture was cooled 60 °C and 15.1 g (1 mole equivalent relative to maleated soybean oil) of diethanolamine diluted in 150 g of water was added over 30-45 minutes. The reaction mixture was held at 60 °C for 4-6 hours. The viscous, biphasic mixture was neutralized by adding 9.5 g (0.9 mole equivalent relative to maleated soybean oil) of 50 wt% aqueous sodium hydroxide over 15 minutes, and the mixture was held at 60 °C for 1-2 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.

[0279] Example G6: Sodium salt of maleated soybean oil reacted with 2 equivalents of diethanolamine

[0280] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 150 g of maleated soybean oil, produced as in Example Al, and 150 g of water were heated to 90 °C for 2 h. The mixture was cooled 60 °C and 30.2 g (2 mole equivalents relative to maleated soybean oil) of diethanolamine diluted in 150 g of water was added over 30-45 minutes. The reaction mixture was held at 60 °C for 4-6 hours. The viscous, biphasic mixture was neutralized by adding 9.5 g (0.9 mole equivalent relative to maleated soybean oil) of 50 wt% aqueous sodium hydroxide over 15 minutes, and the mixture was held at 60 °C for 1-2 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.

[0281] Example G7: Sodium salt of maleated soybean oil reacted with hydrophobic 1 -hexanol and hydrophilic glycerol

[0282] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of maleated soybean oil, produced as in Example Al, and 26.8 g (1.5 mole equivalents relative to maleated soybean oil) of 1 -hexanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (16.1 g, 1.0 mole equivalent relative to maleated soybean oil) was added, and the mixture was held at 85 °C for an additional 6 hours. Aqueous sodium hydroxide (50 wt%, 10.5 g, 0.75 mole equivalent relative to maleated soybean oil) was added over30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0283] Example G8: Sodium salt of maleated soybean oil reacted with hydrophobic 2- ethylhexanol and hydrophilic glycerol

[0284] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 181 g of maleated soybean oil, produced as in Example Al, and 31.1 g (1.5 mole equivalents relative to maleated soybean oil) of 2-ethylhexanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (14.7 g, 1.0 mole equivalent relative to maleated soybean oil) was added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, 98.9 g of maleated soybean oil reacted with 2-ethylhexanol and glycerol was heated to 85 °C, 4.16 g (0.75 mole equivalent) of 50% aqueous sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0285] Example G9: Sodium salt of maleated soybean oil reacted with hydrophobic castor oil and 2-ethylhexanol

[0286] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of maleated soybean oil, produced as in Example Al, and 49.0 g (0.3 mole equivalent relative to maleated soybean oil) of castor oil were combined, heated to 85 °C and held at 85 °C for 6 hours. The amber, viscous product was characterized by NMR and IR, and GC indicated <5% of residual castor oil. 2-Ethylhexanol (34.4 g, 1.5 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, the maleated soybean oil reacted with castor oil and 2- ethylhexanol was heated to 85 °C, 10.6 g of 50% aqueous sodium hydroxide (0.75 mole equivalent) was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0287] Example G10: Sodium salt of maleated soybean oil reacted with hydrophobic 2- ethylhexanol and castor oil and hydrophilic glycerol

[0288] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 85 g of maleated soybean oil, produced as in Example Al, and 14.7 g (1.5 mole equivalents relative to maleated soybean oil) of 2-ethylhexanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (3.45g, 0.5 mole equivalent) and castor oil (92.7 g, 1.0 mole equivalent) were added, and the mixture was heated to 90 °C and held at 90 °C for 6 hours. The product was characterized by NMR and IR. Yield was >96%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, the maleated soybean oil reacted with 2-ethylhexanol, glycerol and castor oil was heated to 85 °C, 4.50 g (0.75 mole equivalent) of 50% aqueous sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR. and IR. Yield was >98 %.

[0289] Example Gil: Sodium salt of maleated soybean oil reacted with hydrophobic dodecanol and hydrophilic glycerol

[0290] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of maleated soybean oil, produced as in Example Al, and 48.9 g (1.5 mole equivalents relative to maleated soybean oil) of dodecanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (16.1 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. The product was characterized by NMR and IR. Yield was >96%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, the maleated soybean oil reacted with dodecanol and glycerol was heated to 85 °C, 10.50 g (0.75 mole equivalent) of 50% aqueous sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0291] Example G12: Sodium salt of maleated soybean oil reacted with hydrophobic 2-octyl- 1 -dodecanol and hydrophilic glycerol

[0292] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 260 g of maleated soybean oil, produced as in Example Al, and 97.7 g (1.5 mole equivalents relative to maleated soybean oil) of 2-octy 1-1 -dodecanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (20.1 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. The product was characterized by NMR andIR. Yield was >96%. In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter and mechanical stirrer, the maleated soybean oil reacted with 2-octyl-l -dodecanol and glycerol was heated to 85 °C, 13.1 g (0.75 mole equivalent) of 50% aqueous sodium hydroxide was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0293] Example G13: Sodium salt of maleated soybean oil reacted with hydrophobic eicosanol and hydrophilic glycerol

[0294] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of maleated soybean oil, produced as in Example Al, and 78.4 g (1.5 mole equivalents relative to maleated soybean oil) of eicosanol were combined, heated to 85 °C and held at 85 °C for 8 hours. Glycerol (10.5 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. Aqueous sodium hydroxide (50 wt%, 10.5 g, 0.75 mole equivalent relative to maleated soybean oil) was added over 30 minutes, and the mixture was held at 85 °C for 4 hours. The amber, liquid product was characterized by NMR and IR. Yield was >98 %.

[0295] Example Hl: Maleated soybean oil reacted with hydrophilic 1,3 -propanediol and hydrophobic 2-octyldodecanol

[0296] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 125 g of MSBO made according to Example Al and 3.36 g (0.4 mole equivalent relative to MSBO) of 1,3-propanediol were combined, heated to 85 °C and held at 85 °C for 2 hours. The amber, viscous, crosslinked product was characterized by NMR and IR. 2- Octyldodecanol (65.8 g, 2 mole equivalents) was added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous, crosslinked product was characterized by NMR and IR. Yield was >96%.

[0297] Example H2: Maleated soybean oil reacted with hydrophobic behenyl alcohol and hydrophilic 1,3-propanediol

[0298] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 150 g of MSBO made according to Example Al and 69.1 g (1.5 mole equivalents relative to MSBO) of behenyl alcohol were combined, heated to 85 °C and held at 85°C for 8 hours. 1,3-Propanediol (10.2 g, 1.0 mole equivalent) was added, and the mixture was heated to 100 °C and held at 100 °C for 6 hours. The product was characterized by NMR and IR. Yield was >96%.Examples for metal working fluid compositions

[0299] Corrosion: Iron chip corrosion testing was performed to address the corrosion resistance benefits of maleated oil. For the test, metal working fluid concentrates were diluted to 5, 4, and 3 wt% with 100 ppm CaCO3 hardwater. A filter paper lined petri dish is filled with iron chips, which were submerged in the different MWF dilution. After 2 hours, the petri dishes were decanted, and left exposed to air in a temperature and humidity-controlled room overnight. Iron chips were removed from the petri dishes and the filter paper was inspected for rust. Beneficial corrosion resistance was displayed by samples that had the least rust at the lowest MWF dilution weight percent.

[0300] MWF concentrates were prepared with 4.8 - 5.1 wt% additive and analyzed for corrosion resistance (Table 1 & 2). Figure 1 shows that improved corrosion resistance can be observed for the maleated oil with base (Example S- Form#2), Maleated oil with hydrophobic and hydrophilic groups (Example Cl-Form#3), and Form#8 vs a naphthenic oil control (Form#l). Figure 3 displays corrosion data for another synthetic MWF with various maleated oil derivatives. Form#10, 13, and 17 show matching corrosion performance to the control, Form#9, a naphthenic base oil.

[0301] Lubricity: Lubricity of the maelated oil additives was measured by Microtap torque. Microtap torque is performed by measuring the force required to tap a predrilled hole in a test alloy in the presence of a MWF. Microtap MWFs are typically prepared by diluting a MWF to 10 wt% in either deionized water or synthetic hardwater. The lower the force required to tap the hole, the better the lubricant.

[0302] MWF concentrates were prepared with 4.8-5.1 wt% additive and analyzed for lubricity on 1018 low carbon steel (Table 1 & 2). The control MWF contained naphthenic oil as the additive (Form#l), which had the highest torque and lowest lubricity. Improved lubricity can be observed for maleated oils modified with 2 equivalents of linear alkane (Form#7) and maleated oil modified with 2.0 equivalents of a heterocycle (Form#8) for Microtap torque due to the low torque values(Figure 2). Figure 4 displays various maleated oil derivates with torque values lower than the control napthenic base oil (Form#9). Each oil exhibits a -8-12% reduction in torque vs Form#9.

[0303] Emulsification: The emulsification behavior of the maleated oil derivatives were tested by finding the minimum amount of emulsifier required to create microemulsions, or clear solutions. To test, all ingredients were incorporated into the metalworking fluid except the emulsifier. Emulsifier was subsequently added dropwise until the solutions turned transparent.

[0304] MWF concentrates were prepared with 5 wt% additive (Table 3) and analyzed for emulsification behavior. Samples prepared with malaeted oils exhibited the need for far less emulsifier vs the control (Figure 5). The best performance was maleated oil with base, Form#21, which required no additional emulsifier to generate a clear, transparent solution.

[0305] EXAMPLE 1: Semi synthetic metal working fluid formulation working examples are listed below (Table 1). The maleated oil additives have a degree of substitution of 3, followed by a reaction of various equivalents of a hydrophobic of hydrophilic group.Table 1

[0306] EXAMPLE 2: Semi synthetic metal working fluid formulation working examples are listed below (Table 2). The maleated oil additives have a degree of substitution ranging from 1.1- 3, followed by a reaction of various equivalents of a hydrophobic, hydrophilic group, and / or base.Table 2

[0307] EXAMPLE 3: Semi synthetic metal working fluid formulation working examples are listed below (Table 3). The maleated oil additives have a degree of substitution ranging from 1.1- 3, followed by a reaction of various equivalents of a hydrophobic, hydrophilic group, and / or base.

[0308] Embodiment A. A metal working fluid composition comprising:

[0309] (A) a reaction product comprises a maleated natural oil, comprising a natural oil with maleated functionality; and a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof.

[0310] Embodiment B. The metal working fluid composition according to embodiment A, further comprising (B) one or more metalworking fluid additive(s).

[0311] Embodiment C. The metal working fluid composition according to embodiment A, 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.

[0312] Embodiment D. The metal working fluid composition according to embodiment C, wherein the maleated natural oil is a maleated soybean oil.

[0313] Embodiment E. The metal working fluid composition according to embodiment A, wherein the reaction product comprises a maleated functionality functionalized with a hydrophobic moiety, a maleated functionality functionalized with a hydrophilic moiety, an unreacted maleated functionality or combinations thereof.

[0314] Embodiment F. The metal working fluid composition according to embodiment A, wherein the hydrophobic moiety is a moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl amines, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; unsubstituted or substituted polyols, with or without additional heteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.

[0315] Embodiment G. The metal working fluid composition according to embodiment A, wherein the hydrophilic moiety is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols, with or without additional heteroatoms, containing from about one to about five carbon atoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl amines, with or without heteroatoms, containing from about one to about five carbon atoms; unsubstituted or substituted polyols, with or without additional heteroatoms, containing from about two to about 36 carbon atoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.

[0316] Embodiment H. The metal working fluid composition according to embodiment G, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.

[0317] Embodiment I. The metal working fluid composition according to embodiment F, wherein the hydrophobic moiety is an alcohol selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-l -hexanol, 1 -octanol, 2-octanol, 2 -butyl- 1 -octanol, 2-hexyl-l -decanol, 2-octyl-l -dodecyl alcohol, 1 -tetradecanol, 2- tetradecanol, 1 -hexadecanol, 2-hexadecanol, 1 -octadecanol, behenyl alcohol, 3,7-dimethyl-l- octanol, 2-propyl-l -pentanol, 4-methyl-l -pentanol, and mixtures thereof.

[0318] Embodiment J. The metal working fluid composition according to embodiment G, wherein the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.

[0319] Embodiment K. The metal working fluid composition according to embodiment F, wherein the hydrophilic moiety is that of a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentylglycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof.

[0320] Embodiment L. The metal working fluid composition according to embodiment F, wherein the hydrophobic moiety is that of an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine,oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, and mixtures thereof.

[0321] Embodiment M. The metal working fluid composition according to embodiment G, wherein the hydrophilic moiety is that of an amine selected from the group consisting of 2- methylpentane-l,5-diamine, diethanolamine, serinol, 2-amino-2-ethyl- 1,3 -propanediol, di methyl amine, 2-methylbutylamine, 3-amino-l -propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof.

[0322] Embodiment N. The metal working fluid composition according to embodiment F, wherein the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(l,l-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 polydiphenyl siloxane, dodecylmethylsiloxanehydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.

[0323] Embodiment O. The metal working fluid composition according to embodiment G, wherein the silane is a hydrophilic compound selected from the group consisting of 3- aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

[0324] Embodiment P. The metal working fluid composition according to embodiment A, wherein (A) is present in an amount of from about 0.01% to about 20.0%

[0325] Embodiment Q. The metal working fluid composition according to embodiment B, wherein (B) is present in an amount of from about 1.0% to about 99.99%

[0326] Embodiment R. The metal working fluid composition according to embodiment B, wherein the metal working fluid additive(s) are selected from the group consisting of metal deactivators, lubricants, emulsifiers, coupling agent, anti-wear, corrosion inhibitors,antimicrobials, extreme pressure agents, antifriction agents, bactericides, antioxidants, pH regulators, antirust agents, polymeric substances, chelating agents, base oils, solvents, liquid carriers, solid carriers or fdlers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, anti-freezing agents, clarifiers, stabilizers and mixtures thereof.

[0327] Embodiment S. The metal working fluid composition according to embodiment A, wherein the metal working includes metal forming, machining, grinding, milling, cutting, honing, stamping, drilling, boring, broaching, casting, forging, rolling, piercing, coining, drawing, press forming, deburring, grooving, tapping, chamfering, broaching, reaming, lapping, straightening, and turning operations in automatic and manual machines.

[0328] Embodiment T. The metal working fluid composition according to embodiment A, wherein metal working fluid composition is used for tool protection against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion, increased operational efficiency, longer tool life, chip removal from the processing zone, excellent cooling and lubrication properties, thermal stability, improved surface finish, enhanced fluid life, foam and soap reduction, lower energy consumption and lower total cost of operations.

[0329] Embodiment U. The metal working fluid composition according to embodiment A, wherein the metal working fluid composition is formulated as a liquid, a spray, a paste, a gel, an emulsion, or a mist.

[0330] Embodiment V. The metal working fluid composition according to embodiment 1, wherein the (A) is a reaction product of maleated soybean oil, octyldodecyl alcohol, and glycerol.

[0331] Embodiment W. The metal working fluid composition according to embodiment A, wherein the reaction product is selected from the group of structures represented by the structures set out below:wherein R is ethyl, butyl, hexyl, octyl, 2-ethylhex-l-yl, 2-butyloct-l-yl, 2-hexyldec-l-yl, 2- octyldodec-l-yl or mixtures thereof.

[0332] Embodiment X. A metalworking fluid composition comprising: (A) from about 0.01% to about 20.0% a reaction product of embodiment A; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0333] Embodiment Y. The metalworking fluid composition according to embodiment X, wherein the (A) is a reaction product of maleated soybean oil, octyldodecyl alcohol, and glycerol.

[0334] Embodiment Z. A metal working fluid composition comprising (A) a reaction product of(a) a maleated natural oil, comprising a natural oil with maleated functionality; and (b) a base.

[0335] Embodiment AA. The metal working fluid composition according to embodiment Z, wherein the reaction product comprises a maleated functionality fully or partially reacted with the base.

[0336] Embodiment AB. The metal working fluid composition according to embodiment Z, wherein the base is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

[0337] Embodiment AC. The metal working fluid composition according to embodiment AB, 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.

[0338] Embodiment AD. The metal working fluid composition according to embodiment AB, wherein the organic base is selected from the group consisting of ammonia, primary amines, secondary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.

[0339] Embodiment AE. The metal working fluid composition according to embodiment AC, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

[0340] Embodiment AF. The metal working fluid composition according to embodiment AC, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

[0341] Embodiment AG. The metal working fluid composition according to embodiment AC, 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.

[0342] Embodiment AH. The metal working fluid composition according to embodiment AC, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.

[0343] Embodiment Al. The metal working fluid composition according to embodiment Z, 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 oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixture thereof.

[0344] Embodiment AJ. The metal working fluid composition according to embodiment Z, wherein the maleated natural oil is a maleated soybean oil.

[0345] Embodiment AK. The metal working fluid composition according to embodiment Z, wherein the reaction product comprises one or more structure selected from the group of structures, comprising maleated functionality fully or partially reacted with the base, consisting of the following structures:, and combinations thereof.

[0346] Embodiment AL. The metal working fluid composition according to embodiment Z, further comprising (B) one or more metalworking fluid additive(s).

[0347] Embodiment AM. The metal working fluid composition according to embodiment AL, wherein the metal working fluid additive(s) are selected from the group consisting of metal deactivators, lubricants, emulsifiers, coupling agent, anti-wear, corrosion inhibitors, antimicrobials, extreme pressure agents, antifriction agents, bactericides, antioxidants, pH regulators, antirust agents, polymeric substances, chelating agents, base oils, solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, anti-freezing agents, clarifiers, stabilizers and mixtures thereof.

[0348] Embodiment AN. The metal working fluid composition according to embodiment Z, wherein the metal working includes metal forming, machining, grinding, milling, cutting, honing, stamping, drilling, boring, broaching, casting, forging, rolling, piercing, coining, drawing, press forming, deburring, grooving, tapping, chamfering, broaching, reaming, lapping, straightening, and turning operations in automatic and manual machines.

[0349] Embodiment AO. The metal working fluid composition according to embodiment Z, wherein metal working fluid composition is used for tool protection against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion, increased operational efficiency, longer tool life, chip removal from the processing zone, excellentcooling and lubrication properties, thermal stability, improved surface finish, enhanced fluid life, foam and soap reduction, lower energy consumption and lower total cost of operations.

[0350] Embodiment AP. The metal working fluid composition according to embodiment Z, wherein the metal working fluid composition is formulated as a liquid, a spray, a paste, a gel, an emulsion, or a mist.

[0351] Embodiment AQ. A metalworking fluid composition comprising:(A) from about 0.01% to about 20.0 % a reaction product of embodiment Z; and(B) from about 1.0 % to about 99.99 % one or more metal working fluid additive(s).

[0352] Embodiment AR. A metal working fluid composition comprising (A) a reaction product of:(a) a maleated natural oil, comprising a natural oil with maleated functionality; and(b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and(c) a base.

[0353] Embodiment AS. The metal working fluid composition according to embodiment AR, 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.

[0354] Embodiment AT. The metal working fluid composition according to embodiment AS, wherein the maleated natural oil is a maleated soybean oil.

[0355] Embodiment AU. The metal working fluid composition according to embodiment AR, wherein the reaction product comprises a maleated functionality functionalized with a hydrophobic moiety, a maleated functionality functionalized with a hydrophilic moiety, unreacted maleated functionality or combinations thereof.

[0356] Embodiment AV. The metal working fluid composition according to embodiment AR, wherein the hydrophobic moiety is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl amines, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; unsubstituted or substituted polyols, with or without additional heteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.

[0357] Embodiment AW. The metal working fluid composition according to embodiment AR, wherein the hydrophilic moiety is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols, with or without additional heteroatoms, containing from about one to about five carbon atoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl amines, with or without heteroatoms, containing from about one to about five carbon atoms; unsubstituted or substituted polyols, with or without additional heteroatoms, containing from about two to about 36 carbon atoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.

[0358] Embodiment AX. The metal working fluid composition according to embodiment AW, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.

[0359] Embodiment AY. The metal working fluid composition according to embodiment AV, 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-l -hexanol, 1-octanol, 2-octanol, 2-butyl-l -octanol, 2-hexyl-l -decanol, 2-octyl-l -dodecyl alcohol, 1- tetradecanol, 2-tetradecanol, 1 -hexadecanol, 2-hexadecanol, 1 -octadecanol, behenyl alcohol, 3,7- dimethyl- 1-octanol, 2-propyl-l -pentanol, 4-methyl-l -pentanol, and mixtures thereof.

[0360] Embodiment AZ. The metal working fluid composition according to embodiment AW, wherein the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.

[0361] Embodiment BA. The metal working fluid composition according to embodiment AW, wherein the hydrophilic moiety is that of a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentylglycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof.

[0362] Embodiment BB. The metal working fluid composition according to embodimentAV, wherein the hydrophobic moiety is that of an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, and mixtures thereof.

[0363] Embodiment BC. The metal working fluid composition according to embodimentAW, wherein the hydrophilic moiety is that of an amine selected from the group consisting of 2- methylpentane-l,5-diamine, diethanolamine, serinol, 2-amino-2-ethyl- 1,3 -propanediol, dimethylamine, 2-methylbutylamine, 3 -amino- 1 -propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof.

[0364] Embodiment BD. The metal working fluid composition according to embodiment AV, wherein the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(l,l-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 terminatedpolydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxanehydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.

[0365] Embodiment BE. The metal working fluid composition according to embodiment AW, wherein the silane is a hydrophilic compound selected from the group consisting of 3- aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

[0366] Embodiment BF. The metal working fluid composition according to embodiment AR, wherein the base is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

[0367] Embodiment BG. The metal working fluid composition according to embodiment BF, 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.

[0368] Embodiment BH. The metal working fluid composition according to embodiment BF 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.

[0369] Embodiment BI. The metal working fluid composition according to embodiment BG, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

[0370] Embodiment BJ. The metal working fluid composition according to embodiment BG, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

[0371] Embodiment BK. The metal working fluid composition according to embodiment BG, 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.

[0372] Embodiment BL. The metal working fluid composition according to embodiment BG, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.

[0373] Embodiment BM. The metal working fluid composition according to embodiment AR, wherein the reaction product comprises a compound of the following structure:wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, 1 / 2Mg, 1 / 2Ca, 1 / 2Co, 1 / 2Cu, 1 / 2Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

[0374] Embodiment BN. The metal working fluid composition according to embodiment AR, wherein the reaction product is a polymer comprising the following structure:wherein n is greater than 1; wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties, with or without heteroatoms, containing from about 1 to about 36 carbon atoms; wherein R4is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, alkenylene, arylene and alkarylene moieties, with or without heteroatoms, containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, 1 / 2Mg, 1 / 2Ca, 1 / 2Co, 1 / 2Cu, 1 / 2Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

[0375] Embodiment BO. The metal working fluid composition according to embodiment BM, wherein the reaction product comprises one or more structure selected from the group of the following structures:wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-l -hexyl, 2 -butyl- 1 -octyl, 2-hexyl-1 -decyl, 2-octyl- 1 -dodecyl, or mixtures thereof; and wherein R1, R2and R3are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or arylalkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

[0376] Embodiment BP. The metal working fluid composition according to embodiment BN, wherein the reaction product is a polymer comprising one or more of the following structures:wherein 1 < n < 30; wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-l -hexyl, 2-butyl-l -octyl, 2- hexyl-1 -decyl, 2-octyl-l -dodecyl, or mixtures thereof; wherein R1, R2and R3are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or arylalkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R4is -CH2CH2CH2-,or a mixture thereof.

[0377] Embodiment BQ. The metal working fluid composition according to embodiment BP, wherein the reaction product is a polymer having a weight-average molecular weight from about 3,000 Daltons to about 20,000 Daltons and a weight-average degree of polymerization, n. from about 3 to about 20.

[0378] Embodiment BR. The metal working fluid composition according to embodiment BP, wherein the reaction product is a polymer having a viscosity measured at 25 °C with a Brookfield viscometer ranging from about 100 to about 10,000 cps.

[0379] Embodiment BS. The metal working fluid composition according to embodiment AR, further comprising (B) one or more metalworking fluid additive(s).

[0380] Embodiment BT. The metal working fluid composition according to embodiment BS, wherein the metal working fluid additive(s) are selected from the group consisting of metal deactivators, lubricants, emulsifiers, coupling agent, anti-wear, corrosion inhibitors, antimicrobials, extreme pressure agents, antifriction agents, bactericides, antioxidants, pH regulators, antirust agents, polymeric substances, chelating agents, base oils, solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, anti-freezing agents, clarifiers, stabilizers and mixtures thereof.

[0381] Embodiment BU. The metal working fluid composition according to embodiment AR, wherein the metal working application includes metal forming, machining, grinding, milling,cutting, honing, stamping, drilling, boring, broaching, casting, forging, rolling, piercing, coining, drawing, press forming, deburring, grooving, tapping, chamfering, broaching, reaming, lapping, straightening, and turning operations in automatic and manual machines.

[0382] Embodiment B V. The metal working fluid composition according to embodiment AR, wherein metal working fluid composition is used for tool protection against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion, increased operational efficiency, longer tool life, chip removal from the processing zone, excellent cooling and lubrication properties, thermal stability, improved surface finish, enhanced fluid life, foam and soap reduction, lower energy consumption and lower total cost of operations.

[0383] Embodiment BW. The metal working fluid composition according to embodiment AR, wherein the metal working fluid composition is formulated as a liquid, a spray, a paste, a gel, an emulsion, or a mist.

[0384] Embodiment BX. A metalworking fluid composition comprising:(A) from about 0.01% to about 20.0% a reaction product of embodiment AV; and(B) from about 1.0 % to about 99.0% one or more metal working fluid additive(s).

[0385] Embodiment BY. A metal working fluid composition comprising (A) a reaction product of:(a) a maleated natural oil, comprising a natural oil with maleated functionality;(b) a base; wherein the maleated functionality has been partially reacted with the base; and(c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety.

[0386] Embodiment BZ. The metal working fluid composition according to embodiment BY, wherein the hydrophobic moiety is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, wherein the alcohols and amines contain from about 6 to about 36 carbon atoms and may contain additional heteroatoms; unsubstituted or substituted polyols, with or without additionalheteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.

[0387] Embodiment CA. The metal working fluid composition according to embodiment BY, wherein the hydrophilic moiety is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain additional heteroatoms; unsubstituted or substituted polyols, wherein the unsubstituted or substituted polyols contain from about 2 to about 36 carbon atoms and may contain additional heteroatoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.

[0388] Embodiment CB. The metal working fluid composition according to embodiment CA, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.

[0389] Embodiment CC. The metal working fluid composition according to embodiment BZ, 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-l -hexanol, 1 -octanol, 2-octanol, 2-butyl-l-octanol, 2-hexyl-l -decanol, 2-octyl-l -dodecyl alcohol, 1 -tetradecanol, 2- tetradecanol, 1 -hexadecanol, 2-hexadecanol, 1 -octadecanol, behenyl alcohol, 3,7-dimethyl-l- octanol, 2-propyl-l -pentanol, 4-methyl-l -pentanol, and mixtures thereof.

[0390] Embodiment CD. The metal working fluid composition according to embodiment CA, wherein the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.

[0391] Embodiment CE. The metal working fluid composition according to embodiment CA, wherein the hydrophilic moiety is that of a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentylglycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof.

[0392] Embodiment CF. The metal working fluid composition according to embodiment BZ, wherein the hydrophobic moiety is that of an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, and mixtures thereof.

[0393] Embodiment CG. The metal working fluid composition according to embodiment C A, wherein the hydrophilic moiety is that of an amine selected from the group consisting of 2- methylpentane-l,5-diamine, diethanolamine, serinol, 2-amino-2-ethyl- 1,3 -propanediol, dimethylamine, 2-methylbutylamine, 3 -amino- 1 -propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof.

[0394] Embodiment CH. The metal working fluid composition according to embodiment BZ, wherein the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(l,l-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 poly dimethyl siloxane, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxanehydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.

[0395] Embodiment CI. The metal working fluid composition according to embodiment CA, wherein the silane is a hydrophilic compound selected from the group consisting of 3- aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

[0396] Embodiment CJ. The metal working fluid composition according to embodiment BY, wherein the base is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

[0397] Embodiment CK. The metal working fluid composition according to embodiment CJ, wherein the inorganic base is selected from the group consisting of oxides of alkali metals andalkaline 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.

[0398] Embodiment CL. The metal working fluid composition according to embodiment CJ, 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.

[0399] Embodiment CM. The metal working fluid composition according to embodiment CK, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

[0400] Embodiment CN. The metal working fluid composition according to embodiment CK, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

[0401] Embodiment CO. The metal working fluid composition according to embodiment CK, 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.

[0402] Embodiment CP. The metal working fluid composition according to embodiment CK, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.

[0403] Embodiment CQ. The metal working fluid composition according to embodiment BY, 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.

[0404] Embodiment CR. The metal working fluid composition according to embodiment CQ, wherein the maleated natural oil is a maleated soybean oil.

[0405] Embodiment CS. The metal working fluid composition according to embodiment BY, wherein the reaction product comprises one or more structure selected from the following group of structures:combinations thereof, wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-l -hexyl, 2-buty-l-loctyl, 2- hexyl- 1 -decyl, 2-octyl-l -dodecyl or mixtures thereof.

[0406] Embodiment CT. The metal working fluid composition according to embodiment BY, further comprising (B) one or more metalworking fluid additive(s).

[0407] Embodiment CU. The metal working fluid composition according to embodiment CT, wherein the metal working fluid additive(s) are selected from the group consisting of metal deactivators, lubricants, emulsifiers, coupling agent, anti-wear, corrosion inhibitors, antimicrobials, extreme pressure agents, antifriction agents, bactericides, antioxidants, pH regulators, antirust agents, polymeric substances, chelating agents, base oils, solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, anti-freezing agents, clarifiers, stabilizers and mixtures thereof.

[0408] Embodiment CV. The metal working fluid composition according to embodiment BY, wherein the metal working includes metal forming, machining, grinding, milling, cutting, honing, stamping, drilling, boring, broaching, casting, forging, rolling, piercing, coining, drawing, press forming, deburring, grooving, tapping, chamfering, broaching, reaming, lapping, straightening, and turning operations in automatic and manual machines.

[0409] Embodiment CW. The metal working fluid composition according to embodiment BY, wherein metal working fluid composition is used for tool protection against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion, increased operational efficiency, longer tool life, chip removal from the processing zone, excellentcooling and lubrication properties, thermal stability, improved surface finish, enhanced fluid life, foam and soap reduction, lower energy consumption and lower total cost of operations.

[0410] Embodiment CX. The metal working fluid composition according to embodiment BY, wherein the metal working fluid composition is formulated as a liquid, a spray, a paste, a gel, an emulsion, or a mist.

[0411] Embodiment CY. A metalworking fluid composition comprising: (A) from about 0.01% to about 20.0% a reaction product of Embodiment BY; and (B) from about 1.0 % to about 99.99% one or more metal working fluid additive(s).

[0412] While the compositions and methods of the disclosed and / or claimed inventive concept(s) have been described in terms of particular aspects, it will be apparent to those of ordinary skill in the art that variations may be applied to the compositions and / or methods and in the steps or in the sequence of steps of the method described herein without departing from the concept, spirit and scope of the disclosed and / or claimed inventive concept(s). All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the disclosed and / or claimed inventive concept(s).

Claims

We claim:

1. A metal working fluid composition comprising: a reaction product comprising: a maleated natural oil, comprising a natural oil with maleated functionality; and a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof.

2. A metal working fluid composition comprising a reaction product of(a) a maleated natural oil, comprising a natural oil with maleated functionality; and(b) a base.

3. A metal working fluid composition, preferably according to claim 1 or 2, comprising a reaction product of:(a) a maleated natural oil, comprising a natural oil with maleated functionality;(b) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and(c) a base.

4. A metal working fluid composition, preferably according to claim 1 or 2, comprising a reaction product of:(a) a maleated natural oil, comprising a natural oil with maleated functionality;(b) a base; and(c) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety.

5. The metal working fluid composition according to any of claims 2 to 4, wherein the reaction product comprises a maleated functionality fully or partially reacted with the base.

6. The metal working fluid composition according to any of the preceding claims, further comprising one or more metalworking fluid additive(s).

7. The metal working fluid composition according to any of the preceding claims, wherein the maleated natural oil is selected from the group consisting of maleated avocado oils, maleated castor 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; preferably- maleated soybean oil(s), maleated palm oil(s), maleated canola oil(s), maleated sunflower oil(s), maleated castor oil(s), maleated chickpea oil(s) and maleated clary sage oil(s); more preferably- maleated soybean oil(s).

8. The metal working fluid composition according to any of the preceding claims, wherein the reaction product comprises a maleated functionality functionalized with a hydrophobic moiety, a maleated functionality functionalized with a hydrophilic moiety, an unreacted maleated functionality, or combinations thereof, wherein the hydrophobic moiety is preferably a moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl amines, with or without additional heteroatoms, containing from about 6 to about 36 carbon atoms; unsubstituted or substituted polyols, with or without additional heteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof; and / orwherein the hydrophilic moiety is preferably a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl alcohols, with or without additional heteroatoms, containing from about one to about five carbon atoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl amines, with or without heteroatoms, containing from about one to about five carbon atoms; unsubstituted or substituted polyols, with or without additional heteroatoms, containing from about two to about 36 carbon atoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; unfunctionalized or functionalized silanes with an alcohol, an amine, or combinations thereof; and combinations thereof.

9. The metal working fluid composition according to any of the preceding claims, wherein the hydrophobic moiety is:(i) an alcohol, preferably selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-l -hexanol, 1 -octanol, 2-octanol, 2-butyl- 1-octanol, 2-hexyl-l -decanol, 2-octyl-l -dodecyl alcohol, 1 -tetradecanol, 2-tetradecanol, 1- hexadecanol, 2-hexadecanol, 1 -octadecanol, behenyl alcohol, 3,7-dimethyl-l-octanol, 2-propyl-l- pentanol, 4-methyl-l -pentanol, and mixtures thereof; and / or(ii) an amine, preferably selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecyl amine, undecylamine, pentadecylamine, and mixtures thereof; and / or(iii) a silicon-based compound, preferably selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(l,l-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 terminatedpolydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxanehydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.

10. The metal working fluid composition according to any of the preceding claims, wherein the hydrophilic moiety is selected from one of the following:(i) a polyol, preferably selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentylglycol, eythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof; and / or(ii) an alcohol, preferably selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof; and / or(iii) an amine, preferably selected from the group consisting of 2-methylpentane-l,5- diamine, diethanolamine, serinol, 2-amino-2-ethyl-l,3-propanediol, dimethylamine, 2- methylbutylamine, 3-amino-l -propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof; and / or(iv) a silane preferably selected from the group consisting of 3-aminopropylsilanetriol, N- (2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

11. A metalworking fluid composition comprising:(A) from about 0.01%wt to about 20.0 wt % of a reaction product of any of the preceding claims, based on the total weight of the metalworking fluid composition; and(B) from about 1.0 wt % to about 99.99 wt % one or more metal working fluid additive(s), based on the total weight of the metalworking fluid composition, preferably-wherein the metal working fluid additive(s) are selected from the group consisting of metal deactivators, lubricants, emulsifiers, coupling agent, anti-wear, corrosion inhibitors,antimicrobials, extreme pressure agents, antifriction agents, bactericides, antioxidants, pH regulators, antirust agents, polymeric substances, chelating agents, base oils, solvents, liquid carriers, solid carriers or fdlers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, anti-freezing agents, clarifiers, stabilizers, and mixtures thereof; and / or wherein the metal working includes metal forming, machining, grinding, milling, cutting, honing, stamping, drilling, boring, broaching, casting, forging, rolling, piercing, coining, drawing, press forming, deburring, grooving, tapping, chamfering, broaching, reaming, lapping, straightening, and turning operations in automatic and manual machines; and / or wherein metal working fluid composition is used for tool protection against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion, increased operational efficiency, longer tool life, chip removal from the processing zone, excellent cooling and lubrication properties, thermal stability, improved surface finish, enhanced fluid life, foam and soap reduction, lower energy consumption and lower total cost of operations; and / or wherein the metal working fluid composition is formulated as a liquid, a spray, a paste, a gel, an emulsion, or a mist.

12. The metal working fluid composition according to claim 1, wherein the reaction product is a reaction product of maleated soybean oil, octyldodecyl alcohol, and glycerol.

13. The metal working fluid composition according to claim 1, wherein the reaction product is selected from the group of structures represented by the structures set out below:wherein R is ethyl, butyl, hexyl, octyl, 2-ethylhex-l-yl, 2-butyloct-l-yl, 2-hexyldec-l-yl, 2- octyldodec-l-yl or mixtures thereof.

14. The metal working fluid composition according to any of the preceding claims, wherein the base is selected from the group consisting of(i) inorganic bases, preferably selected from 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;(ii) organic bases, preferably selected from ammonia, primary amines, secondary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof; and(iii) mixtures of (i) and (ii) thereof.

15. The metal working fluid composition according to any of the preceding claims, wherein the metal is selected from the group consisting of:(i) alkali metal, preferably selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof;(ii) alkaline earth metal, preferably selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof; and / or(iii) transition metal, preferably 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.

16. The metal working fluid composition according to any of claim 2 to 4, wherein the reaction product comprises one or more structures selected from the group of structures comprising maleated functionality fully or partially reacted with the base, consisting of the following structures:, and combinations thereof.

17. The metal working fluid composition according to claim 2, wherein the reaction product comprises:(i) a compound of the following structure:wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, 1 / 2Mg, 1 / 2Ca, 1 / 2Co, 1 / 2Cu, 1 / 2Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium;(ii) a polymer comprising the following structure:wherein n is greater than 1;wherein R is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl and alkaryl moieties, with or without heteroatoms, containing from about 1 to about 36 carbon atoms; wherein R4is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, alkenylene, arylene and alkarylene moieties, with or without heteroatoms, containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, 1 / 2Mg, 1 / 2Ca, 1 / 2Co, 1 / 2Cu, 1 / 2Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium, and tetraalkylammonium; or(iii) one or more structures selected from the group of the following structures:wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-1 -hexyl, 2-butyl-1 -octyl, 2-hexyl-1 -decyl, 2-octyl-1 -dodecyl, or mixtures thereof; and wherein R1, R2and R3are each, independently,hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or arylalkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

18. The metal working fluid composition according to claim 2, wherein the reaction product is a polymer comprising one or more of the following structures:wherein 1 < n < 30; wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-1 -hexyl, 2-butyl-1-octyl, 2-hexyl-l-decyl, 2-octyl-l -dodecyl, or mixtures thereof; wherein R1, R2and R3are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or arylalkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R4is -CH2CH2CH2-,or a mixture thereof.

19. The metal working fluid composition according to claim 18, wherein the reaction product is a polymer having: a weight-average molecular weight from about 3,000 Daltons to about 20,000 Daltons, preferably determined by light scattering and / or Gel Permeation Chromatography (GPC); and / or a weight-average degree of polymerization, n, from about 3 to about 20; and / or a viscosity measured at 25 °C with a Brookfield viscometer ranging from about 100 cps to about 10,000 cps.

20. The metal working fluid composition according to claim 4, wherein the reaction product comprises one or more structure selected from the following group of structures:combinations thereof, wherein R is ethyl, butyl, hexyl, octyl, 2-ethyl-l -hexyl, 2-buty-l-loctyl, 2- hexyl- 1 -decyl, 2-octyl-l -dodecyl or mixtures thereof.

21. The composition according to any of the preceding claims for use as- a metal working fluid; and / or- a metalworking fluid composition.

22. The composition for use according to claim 21, which is a liquid, a spray, a paste, a gel, an emulsion, or a mist.

Images