Metal working fluid composition comprising lactam based maleated natural oils and use thereof

Abstract

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 lactam moiety having at least one hydroxyl, thiol or amine functional group. One more aspect of the present invention provides a metal working fluid composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base. Also, the metal working fluid composition further comprises one or more metalworking fluid additive(s).

Description

Docket No.: 4195N-PCTMETAL WORKING FLUID COMPOSITION COMPRISING LACTAM BASED MALEATED NATURAL OILS AND USE THEREOFFIELD OF THE INVENTION

[0001] 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 lactam moiety having at least one hydroxyl, thiol or amine functional group. Also, the present invention provides a metal working fluid composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base.BACKGROUND OF THE INVENTION

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

[0003] Natural oils are important raw materials for synthesizing renewable compounds such as polymers, plastics, and plasticizers, which are useful in a variety of agricultural compositions. However, the difficulty with utilizing natural oils is their composition -they are blends of triglycerides containing varying degrees of unsaturated groups, which are relatively unreactive. To enhance their reactivity, 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 such 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.

[0004] Metalworking fluids (MWFs) play an essential role in the machining and metalworking industry. Their primary function 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, mineral oil-based fluidsDocket No.: 4195N-PCT weres used for these purposes, but in recent years, there has been a growing interest in the use of vegetable oils as an alternative. This shift is driven by several advantages offered by vegetable oils, making them an attractive and sustainable optionUS Patent 9809538B2 describes a modified natural compound synthesized from an epoxidized natural fatty acid, maleated natural fatty acid, epoxidized natural oil, or maleated natural oil and a lactam compound having at least one hydroxyl group, wherein the modified natural compound has utility in, e.g., adhesive or beverage compositions.

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

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

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

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

[0009] PCT Publications WO2023043593, W02023081006, WO2023235637,WO2024197173, and WO2024197212 discloses modified naturals oils in various applications.

[0010] PCT Applications 2019113068A1 describe a technology related to metalworking fluids comprising maleated soybean oil derivatives.

[0011] 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.Docket No.: 4195N-PCT

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

[0013] 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.

[0014] 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.

[0015] The present invention having metal working fluid composition comprising a reaction product of modified natural oils with lactam moieties 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.Docket No.: 4195N-PCTBRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figure 1. The naphthenic oil control, Form#l, shows corrosion at 3 wt%. Form#2, #3, and #4 contain a lactam modified oil, and show decreased corrosion efficacy.

[0017] Figure 2. The control, Form#l has the highest torque and the worst lubricity. Form#2, #3, and #4 contain a lactam modified oil, and have lower torque values, indicating heightened lubricity.

[0018] Figure 3. The control, Form#5, contains an emulsifier. Form#6, #7, and #8 contain a lactam modified oil, and show significantly reduced emulsifier needed to form a stable emulsion.Docket No.: 4195N-PCTSUMMARY OF THE INVENTION

[0019] One of the aspects of the present application is to provide 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 lactam moiety having at least one hydroxyl, thiol or amine functional group.

[0020] Another aspect of the present invention is to provide a metal working fluid composition of a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, further comprising one or more metalworking fluid additive(s) selected from the group consisting of: further comprising one or more metalworking fluid additive(s) selected from the group consisting of lubricity agent, auxiliary agent, pH-regulator, base oil, transport component, corrosion-inhibiting component, alkalinity agent, anti-foaming agent, biocide, fungicide, and optionally one or more additional additives.

[0021] One more aspect of the present invention provides a metal working fluid for application related to 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.

[0022] Another aspect of the present invention provides a metal working fluid composition, comprising: a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base.

[0023] One more aspect of the present invention provides a metal working fluid composition of a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base, further comprising one or more metalworking fluid additive(s) selected from the group consisting of: one or more polymeric lubricity agents; one or more auxiliary agents; pH- regulator; base oil; a transport component, optionally being water; optionally one or more of: a corrosion-inhibiting component, an alkalinity agent, an anti-foaming agent, a biocide, and / or a fungicide; and optionally one or more additive.Docket No.: 4195N-PCT

[0024] A metal working fluid composition comprising a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and, (D) optionally, a base.

[0025] One more aspect of the present invention is to provide a metal working fluid composition of a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and, (D) optionally, a base, further comprising one or more metalworking fluid additive(s) selected from the group consisting of: one or more polymeric lubricity agents; one or more auxiliary agents; pH-regulator; base oil; a transport component, optionally being water; optionally one or more of: a corrosioninhibiting component, an alkalinity agent, an anti-foaming agent, a biocide, and / or a fungicide; and optionally one or more additive.

[0026] 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 of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, and emulsifier are mixed under stirring, water, amines obtaining the first mixed material (1), (b) then the obtained mixture is mixed with coupling agent, lubrication additive, and bactericide to obtain second mixture (2), adding base oil, and any other additive to the second mixture to obtain the mixture of (3), adding a antifoaming agent under stirring and mixing, obtaining the metal working fluid.

[0027] Another aspect of the present invention is to provide method for preparing metal working fluid composition, wherein the step (1) the stirring speed is 400 to 800rpm or until a vortex appears, step (1) the stirring time is 10 to 20min; step (1), the stirring temperature is 25 to 40 degrees centigrade, , step (2) the stirring speed is preferably 400 to 800 rpm, or until a vortex appears;, the stirring time in the step (2) is 10 to 20 min; step (2), the stirring temperature is 25 to 40 degreesDocket No.: 4195N-PCT centigrade, step (3) the stirring of the stirring speed 400 to 800rpm, or until a vortex appears;, the stirring time in the step (3) 10 to 20 min;, step (3), the stirring temperature is 25 to 40 degrees centigrade.DETAILED DESCRIPTION OF THE INVENTION

[0028] One of the aspects of 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 lactam moiety having at least one hydroxyl, thiol or amine functional group.

[0029] 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.

[0030] 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.

[0031] 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’.

[0032] 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 inDocket No.: 4195N-PCT 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.

[0033] 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] The term “reaction product” refers to a substance produced from a chemical reaction of one or more reactant substances.Docket No.: 4195N-PCT

[0040] 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.

[0041] 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

[0042] As used herein, the term “moiety” or “moieties” refers to a part or a functional group(s) of a molecule.

[0043] 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.

[0044] The term “organic base”, as used herein, includes ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.Docket No.: 4195N-PCT

[0045] 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.

[0046] The term “alkali metal base” includes oxides, hydroxides, carbonates, or bicarbonates of sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr).

[0047] 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).

[0048] 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).

[0049] 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, a suspension or a mist.

[0050] 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.Docket No.: 4195N-PCT

[0051] 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.

[0052] 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 fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, anti-freezing agents, clarifiers, stabilizers and mixtures thereof.

[0053] The term “functionalized” with reference to any moiety refers to the presence of one or more functional groups in the moiety. Various functional groups may be introduced in a moiety by way of one or more functionalization reactions known to a person having ordinary skill in the art. Non-limiting examples of functionalization reactions include: alkylation, epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Canizzaro reaction, Mannich reaction, 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.

[0054] As used herein, the term "hydrophilic" means that the compound has an affinity for water, whereas "hydrophobic" means not having an affinity for water.

[0055] 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.

[0056] Likewise, hydrophobic moieties have less of an affinity for water than hydrophilic moieties, but the hydrophobic moieties may not necessarily be water-repellant. While hydrophilicDocket No.: 4195N-PCT moi eties have an affinity for water and other polar solvents, hydrophobic moieties tend to have an affinity for oils, fats, and other non-polar solvents.

[0057] 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.

[0058] The term “alkyl” refers to a functionalized or unfunctionalized, monovalent, straightchain, branched-chain, or cyclic Ci-Ceo hydrocarbyl group optionally having one or more heteroatoms. In one non-limiting embodiment, an alkyl is a C1-C45 hydrocarbyl group. In another non-limiting embodiment, an alkyl is a C1-C30 hydrocarbyl group. Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n- hexyl, n-heptyl, n-octyl, 2-ethylhexyl, tert-octyl, iso-norbornyl, n-dodecyl, tert-dodecyl, n- tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The definition of “alkyl” also includes groups obtained by combinations of straight-chain, branched-chain and / or cyclic structures.

[0059] 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.

[0060] 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.Docket No.: 4195N-PCT

[0061] 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.

[0062] 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:Docket No.: 4195N-PCT

[0063] 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.

[0064] The term “heteroatom” refers to oxygen, nitrogen, sulfur, silicon, phosphorous, or halogen. The heteroatom(s) may be present as a part of one or more heteroatom-containing functional groups. Non-limiting examples of heteroatom-containing functional groups include ether, hydroxy, epoxy, carbonyl, carboxamide, carboxylic ester, carboxylic acid, imine, imide, amine, sulfonic, sulfonamide, phosphonic, and silane groups. The heteroatom(s) may also be present as a part of a ring such as in heteroaryl and heteroarylene groups.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] According to one non-limiting embodiment, hydrocarbyl alcohols are classified as primary, secondary and tertiary alcohols, based on the number of carbon atoms connected to theDocket No.: 4195N-PCT 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 is andthe general formula for tertiary alcohols iswherein R, R' and R'' stand for different alkyl, alkylene, aryl, aralkyl, and arylene, groups.

[0069] According to another non-limiting embodiment,, 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.

[0070] According to another non-limiting embodiment,, 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.

[0071] According to another non-limiting embodiment,, the silane is functionalized with an alcohol or an amine, and combinations thereof.

[0072] According to another non-limiting embodiment,, the hydrophobic alcohol is selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzylDocket No.: 4195N-PCT 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-m ethyl- 1 -pentanol, and mixtures thereof. Preferably, the hydrophilic alcohol is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, methoxypolyethylene glycol, and mixtures thereof. Preferably, the hydrophilic polyol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentylglycol, trimethylol propane, N-methyldiethanolamine, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, and mixtures thereof.

[0073] According to another non-limiting embodiment,, the hydrophobic amine is selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, and mixtures thereof. Preferably, the hydrophilic amine is selected from the group consisting of diethanolamine, serinol hydrochloride, 2-amino-2-ethyl-l,3-propanediol, dimethylamine, and mixtures thereof.

[0074] According to another non-limiting embodiment,, 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(hexam ethylene carbonate) and castor oil.

[0075] According to another non-limiting embodiment,, the hydrophobic silicon-based compound is 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, poly dimethyl 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.Docket No.: 4195N-PCTPreferably, the hydrophilic silane is selected from the group consisting of 3- aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

[0076] 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.

[0077] 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.

[0078] In one non-limiting embodiment, the amines selected from the group consisting of primary, secondary, and tertiary amines and combinations thereof.

[0079] 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 is andthe 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.Docket No.: 4195N-PCT

[0080] 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.

[0081] In one non-limiting embodiment, the hydrocarbyl amine is a hydrophilic amine selected from the group consisting of 2-methylpentane-l,5-diamine, diethanolamine, serinol hydrochloride, 2-amino-2-ethyl-l, 3 -propanediol, dimethylamine, and mixtures thereof.

[0082] 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.

[0083] 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.

[0084] In one non-limiting embodiment, the silicon-based compound is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional compound.

[0085] 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(l,l-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, poly dimethyl 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.Docket No.: 4195N-PCTaminopropylmethyl siloxane n-ethyl aminoisobutyl terminated polydimethylsiloxane dimethylsiloxane (amino siloxane) (amino siloxane)poly(l,l-dimethylsilazane) telomer aminopropyl terminated polydimethylsiloxane (aminoMonoaminopropylterminated (tetramethylpiperidinyloxy)propylmethylsiloxane]- polydimethylsiloxane (amino siloxane) dimethylsiloxane copolymerPoly dimethyl siloxane carbinol (hydroxyl) terminated polydimethylsiloxanemonocarbinol terminated polydimethylsiloxane monocarbinol terminated functional poly dimethylsiloxaneDocket No.: 4195N-PCT[bis(hydroxyethyl)amine]terminated silanol terminated polydimethylsiloxane polydimethylsiloxanesilanol terminated polydiphenylsiloxane dodecylmethylsiloxanehydroxypolyalkyleneoxypropyl methylsiloxane

[0086] In one non-limiting embodiment, the silicon-based compound is hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3- ami nopropyl si lanetriol and mixtures thereof.

[0087] In one non-limiting embodiment, the present invention relates to 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 lactam moiety having at least one hydroxyl, thiol or amine functional group.

[0088] In one non-limiting embodiment, 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,Docket No.: 4195N-PCT 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.

[0089] In another non-limiting embodiment, the maleated natural oil is a maleated soybean oil.

[0090] In another non-limiting embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4carbon atoms reside in the lactam ring between the O group and thegroup;

[0091] Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

[0092] In another non-limiting embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:Docket No.: 4195N-PCTand combinations thereof, wherein Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

[0093] In one more embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (-CH2-CH2-); and X is selected from OH, SH and NH2.

[0094] In another embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is l-(2-hydroxyethyl)-2-pyrrolidone (HEP), having the structure:Docket No.: 4195N-PCT

[0095] According to one more embodiment, the present invention relates to a reaction product of (A) a maleated soybean oil; and (B) l-(2-hydroxyethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three 1 -(2-hydroxy ethyl )-2- pyrrolidone moieties.

[0096] In another embodiment, one or more structure(s) of the reaction product is selected from:Docket No.: 4195N-PCT

[0097] In one embodiment, the lactam (B) having at least one hydroxyl, thiol or amine functional group is l-(2-aminoethyl)-2-pyrrolidone, having the structure:

[0098] According to one more embodiment, the present invention relates to a reaction product of (A) a maleated soybean oil; and (B) l-(2-aminoethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three l-(2-aminoethyl)-2- pyrrolidone moieties.

[0099] According to one more embodiment, the present invention relates to one or more structure(s) selected from:Docket No.: 4195N-PCTDocket No.: 4195N-PCTwherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms.

[0100] According to one more embodiment, the metal working fluid composition further comprises further comprising one or more metalworking fluid additive(s) selected from the group consisting of lubricity agent, auxiliary agent, pH-regulator, base oil, transport component, corrosion-inhibiting component, alkalinity agent, anti-foaming agent, biocide, fungicide, and optionally one or more additional additives.

[0101] In another embodiment, the lubricity agent is selected from the group consisting of: block copolymers; polyethylene glycol block copolymers; polypropylene glycol block copolymers; polyethylene glycol / polypropylene glycol block copolymer; block copolymers consisting of a central polyoxypropylene block with a polyoxyethylene chain at either end; block copolymers consisting of a central polyoxyethylene block with a polyoxypropylene chain at either end; tetrablock copolymers derived from the sequential addition of ethylene oxide and propylene oxide to ethylenediamine; ethylene oxide / propylene oxide copolymers having at least one terminal hydroxyl group; water-soluble lubricant base stocks of random copolymers of ethylene oxide and propylene oxide; a water-soluble polyoxyethylene or polyoxypropylene alcohol or a water-soluble carboxylic acid ester of such alcohol; alcohol-started base stocks of all polyoxypropylene groups with one terminal hydroxyl group; monobasic and dibasic acid esters; polyol esters; polyalkylene glycol esters; polyalkylene glycols grafted with organic acids; phosphate esters; polyisobutylenes;Docket No.: 4195N-PCT polyacrylonitriles; polyacrylamides; polyvinylpyrrolidones; polyvinyl alcohols and copolymers of acrylic acid or methacrylic acid; an acrylic ester; and combinations thereof.

[0102] In another embodiment, the auxiliary agent is selected from the group consisting of emulsifying agent, coupling agent, sterilizing agent and antifoaming agent and combinations thereof.

[0103] In one embodiment, the emulsifying agent is selected from a group consisting of an alcohol ether carboxylic acid, fatty alcohol polyoxyethylene polyoxypropylene ether, polyisobutene maleic anhydride and combinations thereof.

[0104] In one more embodiment, the sterilizing agent is selected from the group consisting of 2-butyl 1, 2-benzo isothiazo -3- ketone and 2-bromo-2 - nitro -1, 3 propane diol, and a combinations thereof.

[0105] In another embodiment, the antifoaming agent is dimethyl silicon oil.

[0106] In one embodiment, the coupling agent is tri ethylene nailer ether.

[0107] In one more embodiment, the pH regulator is selected from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, hydrochloric acid, sulfuric acid, nitric acid, carbon dioxide, ammonia, organic acids such as oxalic acid, alkali metal carbonates, alkali metal bicarbonates, and combinations thereof.

[0108] In another embodiment, the base oil selected from the group consisting of water soluble polyalkylene glycols, methoxypolyethylene glycols, and combinations thereof.

[0109] In one embodiment, the transport component is water.

[0110] In one more embodiment, the corrosion-inhibiting is selected from the group consisting of: sulfonates, amines, fatty acids and their derivatives, phosphates, nitrites, nitrates, borates, oils and waxes, and combinations thereof.

[0111] In another embodiment, the alkalinity agent is selected from the group consisting of alkali metal hydroxides; alkanolamines - primary, secondary and tertiary; aminomethylpropanol (AMP-95); diglycolamine (DGA); monoethanolamine (MEA); monoisopropanolamine (MIPA); butylethanolamine (NBEA); dicylclohexylamine (DCHA); diethanolamine (DEA); butyldiethanolamine (NBDEA); triethanolamine (TEA); metal alkali hydroxides; potassiumDocket No.: 4195N-PCT hydroxide; sodium hydroxide, magnesium hydroxide, lithium hydroxide, metal carbonates and bicarbonates; sodium carbonate; sodium bicarbonate; potassium carbonate and potassium bicarbonate; and combinations thereof.

[0112] In one embodiment, the biocide and / or fungicide is selected from the group consisting of N,N'-methylenebismorpholine (MBM); 3,3 '-methylene bis [5-methyloxazolidine] (MBO); a,a',a"-trimethyl-l,3,5-triazine-l,3,5(2H,4H,6H)-triethanol (HPT); hexahydrotriazine (HHT); (ethylenedioxy)dimethanol (EDDM); benzisothiazolinone (BIT); methylisothiazolinone (MIT, MI); chloromethylisothiazolinone (CMIT, CMI, MCI); octylisothiazolinone (OIT, 01); dichlorooctylisothiazolinone (DCOIT, DCOI); butylbenzisothiazolinone (BBIT) , and combinations thereof

[0113] In one more embodiment, the additive is selected from the group consisting of lubricity enhancers, emulsifiers, coupling agent, anti-wear, solvents, liquid carriers, solid carriers, fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, clarifiers, stabilizers, UV stabilizers, and combinations thereof.

[0114] In another embodiment, the metal working is selected from the group consisting of 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.

[0115] In one embodiment, the 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.

[0116] According to one more embodiment the present invention relates to a metal working fluid composition, comprising: a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and (C) a base.Docket No.: 4195N-PCT

[0117] In another embodiment, the base (C) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

[0118] In one embodiment, 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.

[0119] In one more embodiment, 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.

[0120] In another embodiment, the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

[0121] In one embodiment, the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

[0122] In one more embodiment, 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.

[0123] In one more embodiment, the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.

[0124] According to one more embodiment the present invention relates to a reaction product of (A) a maleated soybean oil; (B) l-(2-hydroxyethyl)-2-pyrrolidone; and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium, wherein the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three 1 -(2-hydroxyethyl)-2- pyrrolidone moieties.

[0125] According to one more embodiment the present invention relates to a metal working fluid composition comprising, a compound of one or more structure(s) selected from:Docket No.: 4195N-PCTDocket No.: 4195N-PCT

[0126] According to one more embodiment the present invention relates to a metal working fluid composition comprising a reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and, (D) optionally, a base.

[0127] In another embodiment, the hydrophobic moiety (C) is a moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 6 to about 36 carbon atoms and may contain additional heteroatoms; unsubstituted and substituted polyols, with or without additional heteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.

[0128] In one embodiment, the hydrophilic moiety (C) is a moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain additional heteroatoms; unsubstituted and substituted polyols, wherein the unsubstituted and substituted polyols contain from about 2 to about 36 carbon atoms and may contain additional heteroatoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.

[0129] In one embodiment, the silane is functionalized with an alcohol, an amine, or combinations thereof.

[0130] In another embodiment, 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- 1 -octanol, 2 -hexyl- 1 -decanol, 2-octyl-l -dodecyl alcohol, 1 -tetradecanol, 2-tetradecanol, 1 -hexadecanol, 2-hexadecanol, 1 -octadecanol, 3,7- dimethyl-1 -octanol, 2-propyl-l -pentanol, 4-methyl-l -pentanol, behenyl alcohol, 1- naphthalenemethanol, benzyl alcohol and mixtures thereof.

[0131] In one embodiment, the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.Docket No.: 4195N-PCT

[0132] In one more embodiment, the hydrophilic moiety is that of a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, glycerol, hexylene glycol, sorbitol, neopentylglycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2- deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof.

[0133] In another embodiment, the hydrophobic moiety is that of an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, and mixtures thereof.

[0134] In one embodiment, the hydrophilic moiety is that of an amine selected from the group consisting of diethanolamine, serinol, 2-amino-2-ethyl- 1,3 -propanediol, dimethylamine, 2- methylbutylamine, 3 -amino- 1 -propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof.

[0135] In one more embodiment, 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 polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.

[0136] In another embodiment, the silane is a hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3 -aminopropyl silanetri ol, and mixtures thereof.

[0137] In one embodiment, the base (D) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.Docket No.: 4195N-PCT

[0138] In one more embodiment, 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.

[0139] In another embodiment, 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.

[0140] In one embodiment, the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

[0141] In one more embodiment, the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

[0142] In another embodiment, 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.

[0143] According to one more embodiment, the present invention relates to a reaction product of (A) a maleated soybean oil; (B) l-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base.

[0144] In another embodiment, the present application relates to a metal working fluid composition comprising a reaction product having the structure:Docket No.: 4195N-PCTwherein R7is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, 14 Mg, 14 Ca, 14 Co, 14 Cu, 14 Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

[0145] According to one more embodiment, the present invention relates to a metal working fluid composition comprising a reaction product having one or more structure(s) selected from:Docket No.: 4195N-PCT wherein R7is 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 R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

[0146] In another embodiment, the reaction product is a polymer having the structure:wherein n is greater than 1; wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, Vi Mg,Ca, Vi Co, !4 Cu, Vi Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

[0147] In one embodiment, the present invention relates to a metal working fluid composition comprising a reaction product having the polymer comprises one or more structure(s) selected from:Docket No.: 4195N-PCTwherein 1 < n < 30; wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms.

[0148] In one embodiment, R11is -CH2CH2CH2-,or a mixture thereof.

[0149] 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.

[0150] 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.Docket No.: 4195N-PCT

[0151] 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 fluid composition; 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. % ofDocket No.: 4195N-PCT 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.

[0152] 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.

[0153] 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 fromDocket No.: 4195N-PCT about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.%, based on the total weight of the metal working fluid composition.

[0154] 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 working fluid 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).Docket No.: 4195N-PCT

[0155] 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.

[0156] In one embodiment, the metal working fluid composition is selected from the group consisting of 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.

[0157] In one more embodiment, the 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.

[0158] One more aspect of the present invention provides a method for preparing metal working fluid composition, wherein the method comprises the following steps: (a) mixing a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, and emulsifier are mixed under stirring, water, amines obtaining the first mixed material (1 ), (b) then the obtained mixture is mixed with coupling agent, lubrication additive, and bactericide to obtain second mixture (2), adding base oil, and any other additive to the second mixture to obtain the mixture of (3), adding a antifoaming agent under stirring and mixing, obtaining the metal working fluid.

[0159] In one more embodiment, the step (1) the stirring of the stirring speed is preferably 400 to 800rpm or until a vortex appears, step (1) the stirring time is preferably 10 to 20min; step (1), the stirring temperature is 25-40 degrees centigrade, preferably, step (2) the stirring of the stirring speed is preferably 400 to 800 rpm, or until a vortex appears;, the stirring time in the step (2) is 10 - 20 min; step (2), the stirring temperature is 25-40 degrees centigrade, step (3) the stirring of theDocket No.: 4195N-PCT stirring speed 400 to 800rpm, or until a vortex appears;, the stirring time in the step (3) 10 to 20 min;, step (3), the stirring temperature is 25-40 degrees centigrade.

[0160] 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.

[0161] 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

[0162] 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 CaCCh hardwater. A filter paper lined petri dish is filled with iron chips, which were submerged in the different MWF (Metal Working Fluid) 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.

[0163] MWF concentrates were prepared with 5.0 wt% additive (Table 1) and analyzed for corrosion resistance. Figure 1 shows that corrosion resistance can be observed for the lactam ring containing MWF (Form#2-4), however it is not as good as the naphthenic oil control (Form#l). Form#4 has reduced corrosion up to a 4 wt% dilution vs Form#2-3 showing the best performance of the lactam ring containing additives.

[0164] Lubricity: Lubricity of the maelated oil additives was measured by Mircotap torque. Microtap torque is performed by measuring the force required to tap a predrilled hole in a test alloy in the presence of 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.Docket No.: 4195N-PCT

[0165] MWF concentrates were prepared with 5.0 wt% additive (Table 1) and analyzed for lubricity on 1018 low carbon steel. 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 the lactam ring modified maleated oils (Form#2-4) for Microtap torque due to the lower torque values (Figure 1). The control, Form#l has the highest torque and the worst lubricity. Form#3 has a far lower torque value indicating the highest lubricity. Further Figure 2 indicates the control, Form#l has the highest torque and the worst lubricity. Form#2-4 have far lower torque values indicating heightened lubricity.

[0166] Emulsification: The emulsification behavior of the lactam ring containing oils 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.

[0167] MWF concentrates were prepared with 5 wt% additive (Table 2) and analyzed for emulsification behavior. Samples prepared with lactam ring containing oils exhibited the need for less emulsifier vs the control (Figure 3). The best performance was Form#3, which only required 18.7% of the emulsifier needed vs the napthenic base oil control, Form#l.

[0168] Semi synthetic metal working fluid formulation working examples are listed in Table 1 and Table 2 below. The maleated oil additives has a maleation degree of substitution of 3, followed by a reaction of 1.0, 2.0, or 2.8 equivalents of a lactam ring group.

[0169] Table 1: Semi synthetic metal working fluid formulationDocket No.: 4195N-PCT

[0170] Table 2: Semi synthetic metal working fluid formulation for emulsification testing.

[0171] Embodiment A: 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 lactam moiety having at least one hydroxyl, thiol or amine functional group.

[0172] Embodiment B: The metal working fluid of 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,Docket No.: 4195N-PCT 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.

[0173] Embodiment C: The metal working fluid composition of embodiment A, wherein the maleated natural oil is a maleated soybean oil.

[0174] Embodiment D: The metal working fluid composition of embodiment A, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein:Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2II .CH to 4 carbon atoms reside in the lactam ring between theugroup and thez' group;Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s);X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andR is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.Docket No.: 4195N-PCT

[0175] Embodiment E: The metal working fluid composition of embodimentD, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, whereinQ is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andX is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

[0176] Embodiment F: The metal working fluid composition of embodiment E, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein,Q is a linear alkylene chain having at least two carbon atoms (-CH2-CH2-); andDocket No.: 4195N-PCTX is selected from OH, SH and NH2.

[0177] Embodiment G: The metal working fluid composition of embodiment F, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is 1 -(2 -hydroxy ethyl )-2- pyrrolidone (HEP) having a structure:

[0178] Embodiment H: The metal working fluid composition of embodiment A, comprising a reaction product of (A) a maleated soybean oil; and (B) l-(2-hydroxyethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three l-(2- hydroxyethyl)-2-pyrrolidone moieties.

[0179] Embodiment I: The metal working fluid composition of embodiment H, comprising one or more structure(s) selected from:Docket No.: 4195N-PCT

[0180] Embodiment J: The metal working fluid composition of embodiment F, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is l-(2-aminoethyl)-2- pyrrolidone, having the structure:

[0181] Embodiment K: The metal working fluid composition of embodiment A, comprising a reaction product of (A) a maleated soybean oil; and (B) l-(2-aminoethyl)-2-pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three l-(2-aminoethyl)- 2-pyrrolidone moieties.

[0182] Embodiment L: The metal working fluid composition of embodiment K, comprising one or more structure(s) selected from:Docket No.: 4195N-PCTDocket No.: 4195N-PCTwherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms.

[0183] Embodiment M: The metal working fluid composition of embodiment A, further comprising one or more metalworking fluid additive(s) selected from the group consisting of lubricity agent, auxiliary agent, pH-regulator, base oil, transport component, corrosion-inhibiting component, alkalinity agent, biocide / fungicide, and optionally one or more additional additives.

[0184] Embodiment N: The metal working fluid composition of embodiment M, wherein the lubricity agent is selected from the group consisting of: block copolymers; polyethylene glycol block copolymers; polypropylene glycol block copolymers; polyethylene glycol / polypropylene glycol block copolymer; block copolymers consisting of a central polyoxypropylene block with a polyoxyethylene chain at either end; block copolymers consisting of a central polyoxyethylene block with a polyoxypropylene chain at either end; tetrablock copolymers derived from the sequential addition of ethylene oxide and propylene oxide to ethylenediamine; ethylene oxide / propylene oxide copolymers having at least one terminal hydroxyl group; water-soluble lubricant base stocks of random copolymers of ethylene oxide and propylene oxide; a water-soluble polyoxyethylene or polyoxypropylene alcohol or a water-soluble carboxylic acid ester of such alcohol; alcohol-started base stocks of all polyoxypropylene groups with one terminal hydroxyl group; monobasic and dibasic acid esters; polyol esters; polyalkylene glycol esters; polyalkylene glycols grafted with organic acids; phosphate esters; polyisobutylenes; polyacrylonitriles;Docket No.: 4195N-PCT polyacrylamides; polyvinylpyrrolidones; polyvinyl alcohols and copolymers of acrylic acid or methacrylic acid; an acrylic ester; and combinations thereof.

[0185] Embodiment O: The metal working fluid composition of embodiment M, wherein the auxiliary agent is selected from the group consisting of emulsifying agent, coupling agent, sterilizing agent and anti-foaming agent and combinations thereof.

[0186] Embodiment P: The metal working fluid composition of embodiment O, wherein the emulsifying agent is selected from a group consisting of an alcohol ether carboxylic acid, fatty alcohol polyoxyethylene polyoxypropylene ether, polyisobutene maleic anhydride and combinations thereof.

[0187] Embodiment Q: The metal working fluid composition of embodiment O, wherein the sterilizing agent is selected from the group consisting of 2-butyl 1, 2-benzo isothiazo -3- ketone and 2-bromo-2 - nitro -1, 3 propane diol, and a combinations thereof.

[0188] Embodiment R: The metal working fluid composition of embodiment O, wherein the anti-foaming agent is a dimethyl silicon oil.

[0189] Embodiment S: The metal working fluid composition of embodiment O, wherein the coupling agent is tri ethylene glycol ether.

[0190] Embodiment T: The metal working fluid composition of embodiment O, the pH regulator is selected from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, hydrochloric acid, sulfuric acid, nitric acid, carbon dioxide, ammonia, organic acids such as oxalic acid, alkali metal carbonates, alkali metal bicarbonates, and combinations thereof.

[0191] Embodiment U: The metal working fluid composition of embodiment M, the base oil is selected from the group consisting of water soluble poly alkylene glycols, methoxypolyethylene glycols, and combinations thereof.

[0192] Embodiment V: The metal working fluid composition of embodiment M, wherein the transport component is water.

[0193] Embodiment W: The metal working fluid composition of embodiment M, wherein the corrosion-inhibiting agent is selected from the group consisting of: sulfonates, amines, fatty acids and their derivatives, phosphates, nitrites, nitrates, borates, oils and waxes, and combinations thereof.Docket No.: 4195N-PCT

[0194] Embodiment X: The metal working fluid composition of embodiment M, wherein the alkalinity agent is selected from the group consisting of alkali metal hydroxides; alkanolamines - primary, secondary and tertiary; aminomethylpropanol (AMP -95); diglycolamine (DGA); monoethanolamine (MEA); monoisopropanolamine (MIPA); butyl ethanol amine (NBEA); dicylclohexylamine (DCHA); diethanolamine (DEA); butyldiethanolamine (NBDEA); triethanolamine (TEA); metal alkali hydroxides; potassium hydroxide; sodium hydroxide, magnesium hydroxide, lithium hydroxide, metal carbonates and bicarbonates; sodium carbonate; sodium bicarbonate; potassium carbonate and potassium bicarbonate; and combinations thereof.

[0195] Embodiment Y: The metal working fluid composition of embodiment M, wherein the biocide / fungicide is selected from the group consisting of N,N'-methylenebismorpholine (MBM); 3,3 '-methylene bis [5-methyloxazolidine] (MBO); a,a',a"-trimethyl-l,3,5-triazine- l,3,5(2H,4H,6H)-triethanol (HPT); hexahydrotriazine (HHT); (ethylenedioxy)dimethanol (EDDM); benzisothiazolinone (BIT); methylisothiazolinone (MIT, MI); chloromethylisothiazolinone (CMIT, CMI, MCI); octylisothiazolinone (OIT, 01); dichlorooctylisothiazolinone (DCOIT, DCOI); and butylbenzisothiazolinone (BBIT) , and combinations thereof.

[0196] Embodiment / : The metal working fluid composition of embodiment M, wherein the additives are selected from the group consisting of lubricity enhancers, emulsifiers, coupling agent, anti-wear, solvents, liquid carriers, solid carriers, fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, clarifiers, stabilizers, and combinations thereof.

[0197] Embodiment AA: The metal working fluid composition of embodiment A, wherein the metal working fluid is selected from the group consisting of 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.

[0198] Embodiment AB : The metal working fluid composition of embodiment A, wherein the metal working fluid composition is used for tool protection against solid-to-solid friction, protection against environmental factors, contaminants, harsh temperatures, and corrosion,Docket No.: 4195N-PCT 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.

[0199] Embodiment AC: A metal working fluid composition, comprising: a reaction product of(A) a maleated natural oil, comprising a natural oil with maleated functionality;(B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and(C) a base.

[0200] Embodiment AD: The metal working fluid composition of embodiment AC, 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.

[0201] Embodiment AE: The metal working fluid composition of embodiment AC, wherein the maleated natural oil is a maleated soybean oil.

[0202] Embodiment AF: The metal working fluid composition of embodiment AC, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein:Docket No.: 4195N-PCTY is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2" .CH to 4 carbon atoms reside in the lactam ring between theugroup and thezgroup;Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s);X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andR is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

[0203] Embodiment AG: The metal working fluid composition of embodiment AF, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, whereinQ is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andDocket No.: 4195N-PCTX is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

[0204] Embodiment AH: metal working fluid composition of embodiment AG, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein,Q is a linear alkylene chain having at least two carbon atoms (-CH2-CH2-); andX is selected from OH, SH and NH2.

[0205] Embodiment Al: The metal working fluid composition of embodiment AH, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is l-(2-hydroxyethyl)- 2-pyrrolidone (HEP), having the structure:

[0206] Embodiment AJ: The metal working fluid composition of embodiment AC, wherein the base (C) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

[0207] Embodiment AK: The metal working fluid composition of embodiment AJ, 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 transitionDocket No.: 4195N-PCT metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.

[0208] Embodiment AL: The metal working fluid composition of embodiment AJ, 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.

[0209] Embodiment AM: The metal working fluid composition of embodiment AK, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

[0210] Embodiment AN: The metal working fluid composition of embodiment AK, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

[0211] Embodiment AO: The metal working fluid composition of embodiment AK, 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.

[0212] Embodiment AP: The metal working fluid composition of embodiment AJ, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.

[0213] Embodiment AQ: The metal working fluid composition of embodiment AC, where in the composition is a reaction product of (A) a maleated soybean oil; (B) 1 -(2 -hydroxy ethyl)-2- pyrrolidone; and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium, wherein the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three l-(2-hydroxyethyl)-2-pyrrolidone moi eties.

[0214] Embodiment AR: The metal working fluid composition of embodiment AQ, comprising a reaction product having one or more structure(s) selected from:Docket No.: 4195N-PCTDocket No.: 4195N-PCT

[0215] Embodiment AS: The metal working fluid composition of embodiment AC, further comprising one or more metalworking fluid additive(s) selected from the group consisting of: further comprising one or more metalworking fluid additive(s) selected from the group consisting of lubricity agent, auxiliary agent, pH-regulator, base oil, transport component, corrosioninhibiting component, alkalinity agent, anti-foaming agent, biocide / fungicide, and optionally one or more additional additives.

[0216] Embodiment AT: The metal working fluid composition of embodiment AS, wherein the lubricity agent is selected from the group consisting of: block copolymers; polyethylene glycol block copolymers; polypropylene glycol block copolymers; polyethylene glycol / polypropylene glycol block copolymer; block copolymers consisting of a central polyoxypropylene block with a polyoxyethylene chain at either end; block copolymers consisting of a central polyoxyethylene block with a polyoxypropylene chain at either end; tetrablock copolymers derived from the sequential addition of ethylene oxide and propylene oxide to ethylenediamine; ethylene oxide / propylene oxide copolymers having at least one terminal hydroxyl group; water-soluble lubricant base stocks of random copolymers of ethylene oxide and propylene oxide; a water-soluble polyoxyethylene or polyoxypropylene alcohol or a water-soluble carboxylic acid ester of such alcohol; alcohol-started base stocks of all polyoxypropylene groups with one terminal hydroxyl group; monobasic and dibasic acid esters; polyol esters; polyalkylene glycol esters; polyalkylene glycols grafted with organic acids; phosphate esters; polyisobutylenes; polyacrylonitriles; polyacrylamides; polyvinylpyrrolidones; polyvinyl alcohols and copolymers of acrylic acid or methacrylic acid; an acrylic ester; and combinations thereof.

[0217] Embodiment AU: The metal working fluid composition of embodiment AS, wherein the auxiliary agent is selected from the group consisting of emulsifying agent, coupling agent, sterilizing agent and combinations thereof.

[0218] Embodiment AV: The metal working fluid composition of embodiment AU, wherein the emulsifying agent is selected from a group consisting of an alcohol ether carboxylic acid, fatty alcohol polyoxyethylene polyoxypropylene ether, polyisobutene maleic anhydride and combinations thereof.Docket No.: 4195N-PCT

[0219] Embodiment AW: The metal working fluid composition of embodiment AU, wherein the sterilizing agent is selected from the group consisting of 2-butyl 1, 2-benzo isothiazo -3- ketone and 2-bromo-2 - nitro -1, 3 propane diol, and a combinations thereof.

[0220] Embodiment AX: The metal working fluid composition of embodiment AS, wherein the antifoaming agent is dimethyl silicon oil.

[0221] Embodiment AY: The metal working fluid composition of embodiment AU, wherein the coupling agent is triethylene nailer ether.

[0222] Embodiment AZ: The metal working fluid composition of embodiment AC, wherein the pH regulator is selected from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, hydrochloric acid, sulfuric acid, nitric acid, carbon dioxide, ammonia, organic acids such as oxalic acid, alkali metal carbonates, alkali metal bicarbonates, and combinations thereof.

[0223] Embodiment BA: The metal working fluid composition of embodiment AC, wherein the base oil selected from the group consisting of water soluble polyalkylene glycols, methoxypolyethylene glycols, and combinations thereof.

[0224] Embodiment BB: The metal working fluid composition of embodiment AC, wherein the transport component is water.

[0225] Embodiment BC: The metal working fluid composition of embodiment AC, wherein the corrosion-inhibiting is selected from the group consisting of: sulfonates, amines, fatty acids and their derivatives, phosphates, nitrites, nitrates, borates, oils and waxes, and combinations thereof.

[0226] Embodiment BD: The metal working fluid composition of embodiment AC, wherein the alkalinity agent is selected from the group consisting of alkali metal hydroxides; alkanolamines - primary, secondary and tertiary; aminomethylpropanol (AMP-95); diglycolamine (DGA); monoethanolamine (MEA); monoisopropanolamine (MIPA); butylethanolamine (NBEA); dicylclohexylamine (DCHA); diethanolamine (DEA); butyldiethanolamine (NBDEA); triethanolamine (TEA); metal alkali hydroxides; potassium hydroxide; sodium hydroxide, magnesium hydroxide, lithium hydroxide, metal carbonates and bicarbonates; sodium carbonate; sodium bicarbonate; potassium carbonate and potassium bicarbonate; and combinations thereof.Docket No.: 4195N-PCT

[0227] Embodiment BE: The metal working fluid composition of embodiment AC, wherein the biocide / fungicide is selected from the group consisting of N,N'-methylenebismorpholine (MBM); 3,3 '-methylene bis [5-methyloxazolidine] (MBO); a,a',a''-trimethyl-l,3,5-triazine- l,3,5(2H,4H,6H)-triethanol (HPT); hexahydrotriazine (HHT); (ethylenedioxy)dimethanol (EDDM); benzisothiazolinone (BIT); methylisothiazolinone (MIT, MI); chloromethylisothiazolinone (CMIT, CMI, MCI); octylisothiazolinone (OIT, 01); dichlorooctylisothiazolinone (DCOIT, DCOI); and butylbenzisothiazolinone (BBIT) , and combinations thereof.

[0228] Embodiment BF: The metal working fluid composition of embodiment AC, wherein the additive is selected from the group consisting of lubricity enhancers, emulsifiers, coupling agent, anti-wear, solvents, liquid carriers, solid carriers, fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, clarifiers, stabilizers, UV stabilizers, and combinations thereof.

[0229] Embodiment BG: The metal working fluid composition of embodiment AS, wherein the metal working fluid composition is selected from the group consisting of 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.

[0230] Embodiment BH: The metal working fluid composition of embodiment BG, wherein the 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.

[0231] Embodiment BI: A metal working fluid composition comprising a reaction product of:(A) a maleated natural oil, comprising a natural oil with maleated functionality;(B) a lactam moiety having at least one hydroxyl, thiol or amine functional group;Docket No.: 4195N-PCT(C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and,(D) optionally, a base.

[0232] Embodiment BJ: The metal working fluid composition of embodiment BI, wherein the maleated natural oil (A) 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.

[0233] Embodiment BK: The metal working fluid composition of embodiment BI, wherein the maleated natural oil is a maleated soybean oil.

[0234] Embodiment BL: The metal working fluid composition of embodiment Bl, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:wherein:Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2to 4 carbon atoms reside in the lactam ring between the Augroup and thezzCH xgroup;Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s);Docket No.: 4195N-PCTX is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms; and,R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

[0235] Embodiment BM: The metal working fluid composition of embodiment BL, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, whereinQ is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andX is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.Docket No.: 4195N-PCT

[0236] Embodiment BN: The metal working fluid composition of embodiment BM, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein,Q is a linear alkylene chain having at least two carbon atoms (-CH2-CH2-); andX is selected from OH, SHand NH2.

[0237] Embodiment BO: The metal working fluid composition of embodiment BN, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is l-(2-hydroxyethyl)- 2-pyrrolidone (HEP), having the structure:

[0238] Embodiment BP: The metal working fluid composition of embodiment BI, wherein the hydrophobic moiety (C) is a moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 6 to about 36 carbon atoms and may contain additional heteroatoms; unsubstituted and substituted polyols, with or without additional heteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.

[0239] Embodiment BQ: The metal working fluid composition of embodiment BI, wherein the hydrophilic moiety (C) is a moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain additional heteroatoms; unsubstituted and substituted polyols, wherein the unsubstituted and substituted polyols containDocket No.: 4195N-PCT 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.

[0240] Embodiment BR: The metal working fluid composition of embodiment BQ, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.

[0241] Embodiment BS: The metal working fluid composition of embodiment BP, 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- 1 -octanol, 2 -hexyl- 1 -decanol, 2-octyl-l -dodecyl alcohol, 1 -tetradecanol, 2- tetradecanol, 1 -hexadecanol, 2-hexadecanol, 1 -octadecanol, 3,7-dimethyl-l-octanol, 2-propyl-l- pentanol, 4-methyl-l -pentanol, behenyl alcohol, 1 -naphthalenemethanol, benzyl alcohol and mixtures thereof.

[0242] Embodiment BT : The metal working fluid composition of embodiment BQ, wherein the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.

[0243] Embodiment BU: The metal working fluid composition of embodiment BQ, wherein the hydrophilic moiety is that of a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, glycerol, hexylene glycol, sorbitol, neopentylglycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof.

[0244] Embodiment BV: The metal working fluid composition of embodiment BP, wherein the hydrophobic moiety is that of an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, 2- methylbutylamine, and mixtures thereof.

[0245] Embodiment BW: The metal working fluid composition of embodiment BQ, wherein the hydrophilic moiety is that of an amine selected from the group consisting of diethanolamine,Docket No.: 4195N-PCT serinol, 2-amino-2-ethyl-l,3-propanediol, dimethylamine, 2-methylbutylamine, 3-amino-l - propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof.

[0246] Embodiment BX: The metal working fluid composition of embodiment BP, wherein the silicon based compound is a hydrophobic compound 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 polydimethyl siloxane, monocarbinol terminated functional polydimethylsiloxane, [Bis(hydroxyethyl)amine] terminated poly dimethyl siloxane, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxanehydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.

[0247] Embodiment BY : The metal working fluid composition of embodiment BQ, wherein the silane is a hydrophilic compound selected from the group consisting of 3- aminopropyl silanetri ol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

[0248] Embodiment BZ: The metal working fluid composition of embodiment BQ, wherein the base (D) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.

[0249] Embodiment CA: The metal working fluid composition of embodiment BZ, 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.

[0250] Embodiment CB: The metal working fluid composition of embodiment BZ, 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.Docket No.: 4195N-PCT

[0251] Embodiment CC: The metal working fluid composition of embodiment CA, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.

[0252] Embodiment CD: The metal working fluid composition of embodiment CA, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.

[0253] Embodiment CE: The metal working fluid composition of embodiment CA, 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.

[0254] Embodiment CF : The metal working fluid composition of embodiment BI, wherein the a reaction product of (A) a maleated soybean oil; (B) l-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base.

[0255] Embodiment CG: The metal working fluid composition of embodiment CF, wherein the reaction product has the structure:Docket No.: 4195N-PCT wherein R7is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moi eties 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, Vi Mg, Vi Ca, % Co, ’ / ? Cu, Vi Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.Embodiment CH: The metal working fluid composition of embodiment CG, comprising a reaction product having one or more structure(s) selected from:wherein R7is ethyl, butyl, hexyl, octyl, 2 -ethyl- 1 -hexyl, 2 -butyl- 1 -octyl, 2-hexyl-l -decyl, 2-octyl-l -dodecyl, or mixtures thereof; and wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.

[0256] Embodiment CI: The metal working fluid composition of embodiment BI, wherein the reaction product is a polymer having the structure:Docket No.: 4195N-PCTwherein n is greater than 1; wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, Vi Mg, Vi Ca, % Co, ’ / ? Cu, Vi Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.

[0257] Embodiment CJ: The metal working fluid composition of embodiment CI, wherein the polymer comprises one or more structure(s) selected from:Docket No.: 4195N-PCTwherein 1 < n < 30; wherein R8, R9and R10are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R11is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted and substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms.

[0258] Embodiment CK: The metal working fluid composition of embodiment CJ, wherein R11is -CH2CH2CH2-,or a mixture thereof.

[0259] Embodiment CL: The metal working fluid composition of embodiment BI, further comprising one or more metalworking fluid additive(s) selected from the group consisting of: further comprising one or more metalworking fluid additive(s) selected from the group consisting of lubricity agent, auxiliary agent, pH-regulator, base oil, transport component, corrosioninhibiting component, alkalinity agent, anti-foaming agent, biocide / fungicide, and optionally one or more additional additives.

[0260] Embodiment CM: The metal working fluid composition of embodiment CL, wherein the polymeric lubricity agent is selected from the group consisting of: block copolymers;Docket No.: 4195N-PCT polyethylene glycol block copolymers; polypropylene glycol block copolymers; polyethylene glycol / polypropylene glycol block copolymer; block copolymers consisting of a central polyoxypropylene block with a polyoxyethylene chain at either end; block copolymers consisting of a central polyoxyethylene block with a polyoxypropylene chain at either end; tetrablock copolymers derived from the sequential addition of ethylene oxide and propylene oxide to ethylenediamine; ethylene oxide / propylene oxide copolymers having at least one terminal hydroxyl group; water-soluble lubricant base stocks of random copolymers of ethylene oxide and propylene oxide; a water-soluble polyoxyethylene or polyoxypropylene alcohol or a water-soluble carboxylic acid ester of such alcohol; alcohol -started base stocks of all polyoxypropylene groups with one terminal hydroxyl group; monobasic and dibasic acid esters; polyol esters; polyalkylene glycol esters; polyalkylene glycols grafted with organic acids; phosphate esters; polyisobutylenes; polyacrylonitriles; polyacrylamides; polyvinylpyrrolidones; polyvinyl alcohols and copolymers of acrylic acid or methacrylic acid; an acrylic ester; and combinations thereof.

[0261] Embodiment CN: The metal working fluid composition of embodiment CL, wherein the auxiliary agent is selected from the group consisting of emulsifying agent, coupling agent, sterilizing agent and combinations thereof.

[0262] Embodiment CO: The metal working fluid composition of embodiment CN, wherein the emulsifying agent is selected from a group consisting of an alcohol ether carboxylic acid, fatty alcohol polyoxyethylene polyoxypropylene ether, polyisobutene maleic anhydride and combinations thereof.

[0263] Embodiment CP: The metal working fluid composition of embodiment CN, wherein the sterilizing agent is selected from the group consisting of 2-butyl 1, 2-benzo isothiazo -3- ketone and 2-bromo-2 - nitro -1, 3 propane diol, and a combinations thereof.

[0264] Embodiment CQ: The metal working fluid composition of embodiment CL, wherein the antifoaming agent is dimethyl silicon oil.

[0265] Embodiment CR: The metal working fluid composition of embodiment CN, wherein the coupling agent is tri ethylene nailer ether.

[0266] Embodiment CS: The metal working fluid composition of embodiment CL, wherein the pH regulator is selected from the group consisting of sodium hydroxide, potassium hydroxide,Docket No.: 4195N-PCT lithium hydroxide, hydrochloric acid, sulfuric acid, nitric acid, carbon dioxide, ammonia, organic acids such as oxalic acid, alkali metal carbonates, alkali metal bicarbonates, and combinations thereof.

[0267] Embodiment CT: The metal working fluid composition of embodiment CL, wherein the base oil selected from the group consisting of water soluble polyalkylene glycols, methoxypolyethylene glycols, and combinations thereof.

[0268] Embodiment CU: The metal working fluid composition of embodiment CL, wherein the transport component is water.

[0269] Embodiment CV: The metal working fluid composition of embodiment CL, wherein the corrosion-inhibiting is selected from the group consisting of: sulfonates, amines, fatty acids and their derivatives, phosphates, nitrites, nitrates, borates, oils and waxes, and combinations thereof.

[0270] Embodiment CW: The metal working fluid composition of embodiment CL, wherein the alkalinity agent is selected from the group consisting of alkali metal hydroxides; alkanolamines - primary, secondary and tertiary; aminomethylpropanol (AMP-95); diglycolamine (DGA); monoethanolamine (MEA); monoisopropanolamine (MIPA); butylethanolamine (NBEA); dicylclohexylamine (DCHA); diethanolamine (DEA); butyldiethanolamine (NBDEA); triethanolamine (TEA); metal alkali hydroxides; potassium hydroxide; sodium hydroxide, magnesium hydroxide, lithium hydroxide, metal carbonates and bicarbonates; sodium carbonate; sodium bicarbonate; potassium carbonate and potassium bicarbonate; and combinations thereof.

[0271] Embodiment CX: The metal working fluid composition of embodiment CL, wherein the biocide / fungicide is selected from the group consisting of N,N'-methylenebismorpholine (MBM); 3,3 '-methylene bis [5-methyloxazolidine] (MBO); a,a',a"-trimethyl-l,3,5-triazine- l,3,5(2H,4H,6H)-triethanol (HPT); hexahydrotriazine (HHT); (ethylenedioxy)dimethanol (EDDM); benzisothiazolinone (BIT); methylisothiazolinone (MIT, MI); chloromethylisothiazolinone (CMIT, CMI, MCI); octylisothiazolinone (OIT, OI); dichlorooctylisothiazolinone (DCOIT, DCOI); and butylbenzisothiazolinone (BBIT) , and combinations thereof.Docket No.: 4195N-PCT

[0272] Embodiment CY: The metal working fluid composition of embodiment CL, wherein the additive is selected from the group consisting of lubricity enhancers, emulsifiers, coupling agent, anti-wear, solvents, liquid carriers, solid carriers, fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, clarifiers, stabilizers, UV stabilizers, and combinations thereof.

[0273] Embodiment CZ: The metal working fluid composition of embodiment CL, wherein the metal working fluid composition is selected from the group consisting of 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.

[0274] Embodiment DA: The metal working fluid composition of embodiment CZ, wherein the 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.

[0275] Embodiment DB: A method for preparing metal working fluid composition, wherein the method comprises the following steps: (1) mixing the reaction product of embodiment 90, water, amine and emulsifier are mixed under stirring, obtaining the first mixed material, (2) the first mixture and the water obtained in the step (1), adding a coupling agent, lubricant, and bactericide in stirring and mixing to obtain the mixed material, (3) the second mixture is added with base oil and one or more additive, and adding a antifoaming agent to the mixture obtained in the step (3) under stirring and mixing, obtaining the metal working fluid.

[0276] Embodiment DC: The method for preparing metal working fluid composition of embodiment DB, wherein the step (1) the stirring of the stirring speed is preferably 400 to 800rpm or until a vortex appears, step (1) the stirring time is preferably 10 to 20min; step (1), 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 (2) is 10 - 20min;Docket No.: 4195N-PCT step (2), the stirring temperature is 25-40 degrees centigrade, step (3) the stirring of the stirring speed 400 to 800rpm, or until a vortex appears;, the stirring time in the step (3) 10 to 20min;, step (3), the stirring temperature is 25-40 degrees centigrade.

[0277] The above description fully discloses the invention including preferred embodiments thereof. Modifications and improvements of the embodiments specifically disclosed herein are within the scope of the following claims. Without further elaboration it is believed that one skilled in the art can, given the preceding description, utilize the present invention to its fullest extent. The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows.

Claims

Docket No.: 4195N-PCTWe claim:A metal working fluid composition, comprising a reaction product of:(A) a maleated natural oil, comprising a natural oil with maleated functionality; and(B) one or more moieties selected from the group consisting of a lactam moiety having at least one hydroxyl, a thiol, and an amine functional group.

2. A metal working fluid composition, preferably according to claim 1, comprising a reaction product of:(A) a maleated natural oil, comprising a natural oil with maleated functionality;(B) a lactam moiety having at least one hydroxyl, thiol, or amine functional group; and(C) a base.

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

4. 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 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,Docket No.: 4195N-PCT 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).

5. The metal working fluid composition according to any of the preceding claims, wherein the lactam (B) having at least one hydroxyl, a thiol, or an amine functional group has the structure:wherein:Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2ii CH to 4 carbon atoms reside in the lactam ring between the O group and the / xgroup;Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s);X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups,Docket No.: 4195N-PCT wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andR is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

6. The metal working fluid composition according to any of the preceding claims, wherein the lactam (B) having at least one hydroxyl, a thiol, or an amine functional group has the structure:wherein:Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2" .CH to 4 carbon atoms reside in the lactam ring between theugroup and the7 xgroup;Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s);X is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andR is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl, and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl, and aralkyl groups may or may not contain heteroatoms.Docket No.: 4195N-PCT7. The metal working fluid composition according to any of the preceding claims, wherein the lactam (B) having at least one hydroxyl, a thiol, or an amine functional group is selected from the group consisting of:and combinations thereof, whereinQ is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); each R2, R3, R4, R5, and R6is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; andX is selected from OH, SH and NHR1, wherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.

8. The metal working fluid composition according to any of the preceding claims, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:and combinations thereof, wherein,Docket No.: 4195N-PCTQ is a linear alkylene chain having at least two carbon atoms (-CH2-CH2-); andX is selected from OH, SH and NH2.

9. The metal working fluid composition according to any of the preceding claims, wherein the lactam (B) having at least one hydroxyl, a thiol, or an amine functional group is:-hydroxyethyl)-2-pyrrolidone (HEP); or-aminoethyl)-2-pyrrolidone) .

10. 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 any 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, and(ii) organic bases, preferably selected from any of ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof, and combinations thereof.

11. The metal working fluid composition according to any of the preceding claims, comprising:Docket No.: 4195N-PCT(i) a reaction product of (A) a maleated soybean oil; and (B) 1 -(2-hydroxyethyl)-2- pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three l-(2-hydroxyethyl)-2-pyrrolidone moieties;(ii) a reaction product of (A) a maleated soybean oil; and (B) l-(2-aminoethyl)-2- pyrrolidone, wherein the reaction product is a maleated soybean oil substituted with one, two or three l-(2-aminoethyl)-2-pyrrolidone moieties;(iii) a reaction product of (A) a maleated soybean oil; (B) l-(2-hydroxyethyl)-2- pyrrolidone; and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium, wherein the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three l-(2-hydroxyethyl)-2-pyrrolidone moieties; or(iii) a reaction product of (A) a maleated soybean oil; (B) 1 -(2-hydroxy ethyl )-2- pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base.

12. The metal working fluid composition according to any of the preceding claims, wherein the hydrophobic moiety is a moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 6 to about 36 carbon atoms and may contain additional heteroatoms; unsubstituted and substituted polyols, with or without additional heteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.

13. The metal working fluid composition according any of the preceding claims, wherein the hydrophilic moiety is a moiety selected from those of the group consisting of unsubstituted and substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain additional heteroatoms; unsubstituted and substituted polyols, wherein the unsubstituted and substituted polyols contain from about 2 to about 36 carbon atoms and may contain additional heteroatoms;Docket No.: 4195N-PCT poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.

14. The metal working fluid composition according to claim 13, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.

15. The metal working fluid composition according to claim 12, wherein the hydrophobic moiety is that of:(i) 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, 3,7-dimethyl-l-octanol, 2-propyl-l -pentanol, 4- m ethyl- 1 -pentanol, behenyl alcohol, 1 -naphthalenemethanol, benzyl alcohol and mixtures thereof; and / or (ii) an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, 2- methylbutylamine, and mixtures thereof; and / or combinations thereof16. The metal working fluid composition according to claim 13, wherein the hydrophilic moiety is that of:(i) a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, glycerol, hexylene glycol, sorbitol, neopentylglycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N-methylglucosamine, and mixtures thereof; (ii) an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol; (iii) an amine selected from the group consisting of diethanolamine, serinol, 2-amino-2-ethyl-l,3-propanediol, dimethylamine, 2-methylbutylamine, 3 -amino- 1 -propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof; and / or (iv) a silane selected from the group consisting of 3- aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof; and combinations thereof.Docket No.: 4195N-PCT17. The metal working fluid composition according to any of the preceding claims, comprising one or more structure(s) selected from:Docket No.: 4195N-PCT18. The metal working fluid composition according to claim 2, comprising one or more structure(s) selected from:Docket No.: 4195N-PCTwherein R1is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups may or may not contain heteroatoms.Docket No.: 4195N-PCT19. The metal working fluid composition according to claim 3, comprising a reaction product having one or more structure(s) selected from:Docket No.: 4195N-PCT20. The metal working fluid composition according to any of the preceding claims, further comprising one or more metalworking fluid additive(s), preferably selected from the group consisting of(i) lubricity agent, preferably selected from any of block copolymers; polyethylene glycol block copolymers; polypropylene glycol block copolymers; polyethylene glycol / polypropylene glycol block copolymer; block copolymers consisting of a central polyoxypropylene block with a polyoxyethylene chain at either end; block copolymers consisting of a central polyoxyethylene block with a polyoxypropylene chain at either end; tetrablock copolymers derived from the sequential addition of ethylene oxide and propylene oxide to ethylenediamine; ethylene oxide / propylene oxide copolymers having at least one terminal hydroxyl group; water-soluble lubricant base stocks of random copolymers of ethylene oxide and propylene oxide; a water-soluble polyoxyethylene or polyoxypropylene alcohol or a water-soluble carboxylic acid ester of such alcohol; alcohol-started base stocks of all polyoxypropylene groups with one terminal hydroxyl group; monobasic and dibasic acid esters; polyol esters; polyalkylene glycol esters; polyalkylene glycols grafted with organic acids; phosphate esters; polyisobutylenes; polyacrylonitriles; polyacrylamides; polyvinylpyrrolidones; polyvinyl alcohols and copolymers of acrylic acid or methacrylic acid; an acrylic ester; and combinations thereof,(ii) auxiliary agent, preferably selected from any of (a) emulsifying agent: of an alcohol ether carboxylic acid, fatty alcohol polyoxyethylene polyoxypropylene ether, polyisobutene maleic anhydride and combinations thereof; (b) coupling agent: triethylene nailer ether; (c) sterilizing agent: 2-butyl 1, 2-benzo isothiazo -3- ketone and 2-bromo-2 - nitro -1, 3 propane diol and combinations thereof; and combinations thereof,Docket No.: 4195N-PCT(iii) pH-regulator, preferably selected from any of sodium hydroxide, potassium hydroxide, lithium hydroxide, hydrochloric acid, sulfuric acid, nitric acid, carbon dioxide, ammonia, organic acids such as oxalic acid, alkali metal carbonates, alkali metal bicarbonates, and combinations thereof,(iv) base oil, preferably selected from any of water soluble polyalkylene glycols, methoxypolyethylene glycols, and combinations thereof,(v) transport component, preferably water,(vi) corrosion-inhibiting component, preferably selected from any of sulfonates, amines, fatty acids and their derivatives, phosphates, nitrites, nitrates, borates, oils and waxes, and combinations thereof,(vii) alkalinity agent, preferably selected from any of alkali metal hydroxides; alkanolamines - primary, secondary and tertiary; aminomethylpropanol (AMP-95); diglycolamine (DGA); monoethanolamine (MEA); monoisopropanolamine (MIPA); butylethanolamine (NBEA); dicylclohexylamine (DCHA); diethanolamine (DEA); butyldiethanolamine (NBDEA); triethanolamine (TEA); metal alkali hydroxides; potassium hydroxide; sodium hydroxide, magnesium hydroxide, lithium hydroxide, metal carbonates and bicarbonates; sodium carbonate; sodium bicarbonate; potassium carbonate and potassium bicarbonate; and combinations thereof,(viii) anti-foaming agent, preferably dimethyl silicon oil,(ix) biocide / fungicide, preferably selected from any of N,N'-methylenebismorpholine (MBM); 3,3 '-methylene bis [5-methyloxazolidine] (MBO); a,a',a"-trimethyl-l,3,5-triazine- l,3,5(2H,4H,6H)-triethanol (HPT); hexahydrotriazine (HHT); (ethylenedioxy)dimethanol (EDDM); benzisothiazolinone (BIT); methylisothiazolinone (MIT, MI); chloromethylisothiazolinone (CMIT, CMI, MCI); octylisothiazolinone (OIT, 01); dichlorooctylisothiazolinone (DCOIT, DCOI); and butylbenzisothiazolinone (BBIT) , and combinations thereof, and(x) optionally one or more additional additives.

21. The metal working fluid composition according to any of the preceding , wherein the metal working fluid is selected from the group consisting of metal forming, machining, grinding, milling, cutting, honing, stamping, drilling, boring, broaching, casting, forging, rolling,Docket No.: 4195N-PCT piercing, coining, drawing, press forming, deburring, grooving, tapping, chamfering, broaching, reaming, lapping, straightening, and turning operations in automatic and manual machines.

22. The metal working fluid composition according to any of the preceding claim, wherein the metal working fluid composition is used for one or more of 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.

23. A method for preparing a metal working fluid composition, wherein the method comprises the following steps:(1) mixing the reaction product of any of claims 1 to 3, water, amine and emulsifier under stirring, thereby obtaining a first mixed material,(2) adding a coupling agent, lubricant, and bactericide to the first mixed material obtained in step (1) under stirring and mixing to obtain a second mixed material,(3) the second mixture is added with base oil and optionally one or more additives according to claim 20, and adding an antifoaming agent to the mixture obtained in the step (2) under stirring and mixing, thereby obtaining the metal working fluid.

24. The method for preparing the metal working fluid composition according to claim 23, wherein-in step (1) the stirring speed is 400 to 800rpm or until a vortex appears; in step (1) the stirring time is 10 to 20min; step (1), the stirring temperature is 25 to 40 degrees centigrade, and / or-in step (2) the stirring speed is 400 to 800rpm, or until a vortex appears; the stirring time in the step (2) is 10 to 20min; and / or in step (2), the stirring temperature is 25 to 40 degrees centigrade; and / or in step (3) the stirring speed is 400 to 800rpm, or until a vortex appears; the stirring time in the step (3) is 10 to 20min; and / or in step (3), the stirring temperature is 25to 40 degrees centigrade.

25. The composition according to any of the preceding claims for use asDocket No.: 4195N-PCT- a metal working fluid; and / or- a metal working fluid composition. wherein the composition is a liquid, a spray, a paste, a gel, an emulsion, a suspension or a mist.

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