Metal working fluid compositions comprising 3-amino-3-methyl-2-butanol and uses thereof

Abstract

The present technology is generally directed to metalworking fluid compositions comprising 3-amino-3-methyl-2-butanol. For example, 3-amino-3-methyl-2-butanol is included in a metalworking fluid having a pH of at least about 7, and lubrication, cleaning, and / or handling performance of the metalworking fluid may be enhanced by providing multi-metal corrosion inhibition, maintaining pH control, and / or stabilizing the metalworking fluid.

Description

Cross-reference to related applications

[0001] This application claims the benefit and priority of U.S. Provisional Application No. 63 / 540,850, filed on September 27, 2023, which is incorporated herein by reference in its entirety for any and all purposes. Technical Field

[0002] This technology generally relates to metalworking fluid compositions comprising 3-amino-3-methyl-2-butanol, which can be used in a variety of metalworking operations on various metals (e.g., cutting, grinding, drilling, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, and protection). For example, the inclusion of 3-amino-3-methyl-2-butanol in metalworking fluids with a pH of at least about 7 can enhance the lubrication, cleaning, and handling properties of metalworking fluids by providing multi-metal corrosion inhibition, maintaining pH control, and stabilizing the metalworking fluid. Background Technology

[0003] Many commonly used metalworking fluids are made from compositions using chemicals that are typically derived from non-renewable raw materials such as petroleum. For example, in addition to petroleum fractions in pure oils and semi-synthetic metalworking fluids, surfactants in metalworking fluids are also typically derived from petroleum resources, including neutralizers used to neutralize acid groups present in the composition.

[0004] The use of non-renewable petroleum-based feedstocks has led to an over-reliance on fossil fuels. This dependence on non-renewable petroleum-based feedstocks has resulted in environmental degradation, such as air pollution, water pollution, and global warming. Furthermore, these fossil fuels are often supplied by politically unstable regions of the world, frequently raising humanitarian concerns.

[0005] Therefore, as described above and explained in more detail below, there remains a need for compositions for commonly used metalworking fluids that are made from natural, renewable starting materials and can provide performance comparable to or better than existing products. Summary of the Invention

[0006] This disclosure relates to compositions of metalworking fluids for various metalworking operations (e.g., cutting, grinding, drilling, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, and protection) of various metals (e.g., aluminum, steel, and copper), wherein such compositions comprise 3-amino-3-methyl-2-butanol (also known as 3-amino-3-methylbut-2-ol; CAS No.: 13325-14-9). 3-amino-3-methyl-2-butanol offers several advantages, including its improved sustainability properties, which are reflected in its ability to be manufactured as a renewable bio-based compound (i.e., not dependent on non-renewable petroleum-based feedstocks), and its low toxicity (providing a safer alternative with reduced environmental and health impacts), while offering performance comparable to or better than petroleum-based alternatives and superior performance compared to existing renewable alternatives (e.g., NH3, NaOH). Therefore, the technology disclosed herein overcomes common adoption barriers associated with renewable chemicals, such as poor performance and high cost. Instead, the technology disclosed herein provides a high-performance, cost-effective solution with the potential to integrate bio-based carbon. Brief description of the attached diagram Figure 1 The working examples demonstrate cobalt leaching control using 3-amino-3-methyl-2-butanol (“AMB” of the present invention), 2-amino-2-methyl-1-propanol (“AMP”), monoisopropanolamine (“MIPA”), and monoethanolamine (“MEA”). Figure 1 This indicates that AMB provides significantly better cobalt leaching control compared to MIPA and MEA, and comparable cobalt leaching control compared to AMP.

[0008] Figure 2 This demonstrates staining control of a metalworking fluid comprising AMB, MIPA, and MEA, according to a working embodiment. Figure 2 As shown, AMB exhibits lower staining and less corrosion compared to AMP and MEA.

[0009] Figure 3 The results of iron corrosion in exemplary metalworking fluids containing AMB, AMP, or MEA, evaluated by modified IP287 CICT (cast iron chips test) at concentrations of 3.0-4.5%, according to working embodiments, are shown. AMB was found to provide performance comparable to or better than AMP.

[0010] Figure 4 Results evaluating the relationship between emulsifier percentage and surface tension in semi-synthetic drawing fluids, based on working examples, are presented. It was found that semi-synthetic drawing fluid compositions containing AMB require less emulsifier to achieve similar surface tension than those containing AMP. Detailed Implementation

[0011] The following terms will be used throughout this document as defined below.

[0012] As used herein and in the appended claims, in the context of describing elements (particularly in the context of the appended claims), singular articles such as “a,” “an,” “the,” and similar designations should be interpreted to cover both singular and plural forms, unless otherwise indicated herein or clearly contradicted by the context. Unless otherwise stated herein, the enumeration of ranges of values ​​herein is intended only as a shorthand method for individually referring to each individual value falling within that range, and each individual value is incorporated into this specification as if it were individually enumerated herein. All methods described herein may be performed in any suitable order, unless otherwise stated herein or clearly contradicted by the context. Unless otherwise stated, the use of any and all instances or exemplary language (e.g., “for example”) provided herein is intended only to better illustrate the embodiments and does not constitute a limitation on the scope of the claims. The language in the specification should not be construed as indicating that any unclaimed element is essential.

[0013] As used herein, “about” will be understood by those skilled in the art and will vary to some extent depending on the context in which it is used. Where there is a situation where even those skilled in the art are unclear about the usage of the term based on the context in which it is used, “about” will mean at most 10% of the specific term, for example, “about 10 wt%” should be understood to mean “9 wt% to 11 wt%”. It should be understood that when a term is preceded by “about”, the term should be interpreted as disclosing both “about” and the term itself without the “about” modifier; for example, “about 10 wt%” discloses both “9 wt% to 11 wt%” and “10 wt%”.

[0014] As used in this disclosure, the phrase “and / or” should be understood to mean any single member of the listed members, or any combination of two or more members, for example, “A, B and / or C” should mean “A or B or C; A and B; A and C; B and C; or a combination of A, B and C”.

[0015] The term "alkyl," whether used alone or as part of another group (e.g., in dialkylamino), refers to a group comprising straight-chain and branched aliphatic groups (i.e., saturated hydrocarbon chains) and, unless otherwise specified, having 1-10, 1-8, or 1-6 alkyl carbon atoms. Representative alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl. Unless otherwise specified, the alkyl group is optionally substituted with 1, 2, or 3, for example 1 or 2, or even only 1, substituent compatible with the compounds, monomers, and polymers described herein. In some embodiments, the alkyl group is unsubstituted.

[0016] The term "alkoxy" refers to a group in which oxygen is linked to a saturated straight-chain or branched alkyl group. Unless otherwise stated, an alkoxy group contains 1 to 6 carbon atoms (e.g., methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, or isohexyloxy), and in any embodiment contains 1 to 4 carbon atoms. In any embodiment, the alkoxy group includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, and tert-butoxy. In some embodiments, the alkoxy group is unsubstituted.

[0017] Groups having two or more connection points (i.e., divalent, trivalent, or polyvalent) in the compounds described herein are designated by using the suffix "-". For example, divalent alkyl is alkylene, divalent cycloalkyl is cycloene, and so on. Substituents having a single connection point with the compounds are not named using "-". Thus, for example, chloroethyl is not referred to herein as chloroethylene.

[0018] Generally, "substituted" refers to an alkyl group as defined above, wherein one or more bonds bonded to a hydrogen atom contained therein are replaced by bonds that are not hydrogen or carbon atoms. Substituents also include groups in which one or more bonds bonded to a carbon or hydrogen atom are replaced by one or more bonds (including double or triple bonds) bonded to a heteroatom. In some embodiments, the substituent is replaced by one, two, or three substituents. Examples of substituents include, but are not limited to, hydroxyl, amino, mercapto, nitro, halogen, ester, amide, carbonyl, or carboxylic acid. Unless otherwise stated, the aforementioned substituents themselves are not further substituted.

[0019] Unless otherwise stated, all molecular weight (i.e., molar mass) data, number-average molecular weight data Mn, or weight-average molecular weight data Mw mentioned in this specification are molar masses that can be determined by gel permeation chromatography (GPC).

[0020] As used herein, “substantially free” means that the specified component is present in a concentration of less than about 2 wt% based on the total weight of the composition. In some embodiments, the composition may contain less than about 1 wt%, less than about 0.5 wt%, or less than about 0.1 wt% of the specified component. In some embodiments, the composition may be free of detectable amounts of the component.

[0021] 3-Amino-3-methyl-2-butanol ("AMB") composition In one aspect, the present technology provides compositions for metalworking fluids and metalworking applications, such as for metal removal, metal forming, metal cleaning and / or metal treatment, and for cutting, grinding, drilling, turning, milling, machining, drawing, stamping, forming, rolling, cleaning and / or protecting of metals and / or metal alloys, wherein the composition comprises about 30 wt% to about 99.99 wt% of 3-amino-3-methyl-2-butanol and about 0.01 wt% to about 70 wt% of water. In any embodiment, the amount of 3-amino-3-methyl-2-butanol contained in the composition may be about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, about 95 wt%, about 96 wt%, about 97 wt%, about 98 wt%, about 99 wt%, about 99.5 wt%, about 99.9 wt%, about 99.95 wt%, about 99.99 wt%, or include these values ​​and / or any range between any two of these values. For example, the composition may contain 85 wt% to 95 wt% of 3-amino-3-methyl-2-butanol. In any embodiment, the composition may contain at least about 90 wt% of 3-amino-3-methyl-2-butanol.

[0022] In any embodiment, the composition may contain 0.01 wt% to about 70 wt% water. Such compositions may be solutions at room temperature, such as homogeneous solutions. In any embodiment, the amount of water contained in the composition may be about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.5 wt%, about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, about 10 wt%, about 11 wt%, about 12 wt%, about 13 wt%, about 14 wt%, about 15 wt%, about 16 wt%, about 17 wt%, about 18 wt%, about 19 wt%, about 20 wt%, about 21 wt%, about 22 wt%, about 23 wt%, about 24 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%. wt%, or any range including these values ​​and / or any two of these values. Therefore, in any embodiment herein, the composition may contain 5 wt% to 15 wt% water or about 10 wt% water. The water may be deionized water, distilled water, or reverse osmosis (RO) water, or any combination thereof, including, for example, double-distilled water. In any embodiment herein, purity and water content may be adjusted according to desired physical properties and end-use application.

[0023] In any embodiment herein, water and / or amino alcohols other than 3-amino-3-methyl-2-butanol (“other amino alcohols”) may be included in a composition containing 3-amino-3-methyl-2-butanol, for example, to improve processing performance and / or enhance performance characteristics. For example, adding water to a composition containing 3-amino-3-methyl-2-butanol can increase the flash point, decrease the freezing point, and / or reduce the viscosity of the composition. Exemplary other amino alcohols that may be included in compositions in any embodiment herein include, but are not limited to, 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or any combination of two or more of these. The composition of any embodiment herein may comprise other amino alcohols (e.g., 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or any combination of two or more thereof), wherein the amount of the other amino alcohol is at least about 0.01 wt%, at least about 0.02 wt%, at least about 0.03 wt%, at least about 0.04 wt%, at least about 0.05 wt%, at least about 0.06 wt%, at least about 0.07 wt%, at least about 0.08 wt%, at least about 0.09 wt%, at least about 0.1 wt%, at least about 0.25 wt%, at least about 0.5 wt%, at least about 0.75 wt%, at least about 1 wt%, at least about 1.5 wt%, at least about 2 wt%, at least about 2.5 wt%, at least about 3 wt%. wt%, at least about 3.5 wt%, at least about 4 wt%, at least about 4.5 wt%, at least about 5 wt%, about 8 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, or including these values ​​and / or any range between any two of these values.The composition of any embodiment herein may comprise other amino alcohols (e.g., 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or any combination of two or more thereof), in amounts not exceeding about 0.01 wt%, not exceeding about 0.02 wt%, not exceeding about 0.03 wt%, not exceeding about 0.04 wt%, not exceeding about 0.05 wt%, not exceeding about 0.06 wt%, not exceeding about 0.07 wt%, not exceeding about 0.08 wt%, not exceeding about 0.09 wt%, not exceeding about 0.1 wt%, not exceeding about 0.25 wt%, not exceeding about 0.5 wt%, not exceeding about 0.75 wt%, not exceeding about 1 wt%, not exceeding about 1.5 wt%, not exceeding about 2 wt%, not more than about 2.5 wt%, not more than about 3 wt%, not more than about 3.5 wt%, not more than about 4 wt%, not more than about 4.5 wt%, not more than about 5 wt%, or including these values ​​and / or any range between any two of these values.

[0024] In any embodiment herein, the composition may contain less than about 2 wt% of a secondary amine (e.g., 3-(ethylamino)-3-methylbut-2-ol, 2-(butylamino)ethanol, diethanolamine, diisopropanolamine (also known as 1-(2-hydroxypropylamino)prop-2-ol), and / or dicyclohexylamine). Therefore, in any embodiment herein, the amount of secondary amine contained in the composition may be less than about 2 wt%, less than about 1.5 wt%, less than about 1 wt%, less than about 0.5 wt%, or include these values ​​and / or any range between any two of these values. For example, in any embodiment herein, the composition may contain less than about 0.5 wt% of a secondary amine.

[0025] In any embodiment herein, the composition may exhibit a bio-based content of 0% to 100% of 3-amino-3-methyl-2-butanol as determined by radiocarbon analysis according to ASTM D6866-24. For example, such a range of bio-based content of 3-amino-3-methyl-2-butanol in the compositions of the present technology may be provided by using pure petroleum-based 3-amino-3-methyl-2-butanol (i.e., having 0% bio-based content), using 3-amino-3-methyl-2-butanol partially derived from bio-based starting materials, using a combination of pure petroleum-based 3-amino-3-methyl-2-butanol and 3-amino-3-methyl-2-butanol partially or wholly derived from bio-based starting materials; or for 100% bio-based content of 3-amino-3-methyl-2-butanol, it may be provided by using 3-amino-3-methyl-2-butanol entirely derived from bio-based starting materials. Therefore, in any embodiment herein, the composition may exhibit a bio-based content of 3-amino-3-methyl-2-butanol (as determined using radiocarbon analysis according to ASTM D6866-24) of 0%, at least about 1%, at least about 5%, at least about 10%, at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, about 100%, or include these values ​​and / or any range between any two of these values. For example, the composition of any embodiment herein may exhibit a bio-based content of at least about 10% of 3-amino-3-methyl-2-butanol as determined using radiocarbon analysis according to ASTM D6866-24, or may exhibit a bio-based content of at least about 25% of 3-amino-3-methyl-2-butanol as determined using radiocarbon analysis according to ASTM D6866-24.

[0026] Metalworking fluid compositions comprising 3-amino-3-methyl-2-butanol In one aspect, this document provides metalworking fluids comprising 3-amino-3-methyl-2-butanol, water, and optionally a base oil. Metalworking fluids containing such compositions can be used for metal removal, metal forming, metal cleaning, and / or metal treatment (e.g., cutting, grinding, drilling, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, and protection, etc.). Metalworking fluids containing 3-amino-3-methyl-2-butanol can be used in all kinds of metalworking fluid processes, including but not limited to metal removal, cutting, grinding, drilling, metal forming, drawing, stamping, rolling, and forging. Metalworking processes generate heat and friction, and the metalworking fluid compositions of this document provide cooling by removing the heat generated during operation and lubrication between the tool and the metal workpiece (e.g., metal parts). The metalworking fluids of this invention can also remove debris without leaving residue and protect tools and parts being manufactured. 3-Amino-3-methyl-2-butanol can be used in each of four types of metalworking fluids: pure oil, soluble oil, semi-synthetic metalworking fluid, and synthetic metalworking fluid. In any embodiment, the metalworking fluid is provided in concentrated form and diluted with water before use. This technology includes metalworking fluid concentrates comprising base oils and / or synthetic polymers. Metalworking fluids may also contain emulsifiers, lubricants (boundary and extreme pressure lubricants), amines and / or one or more amino alcohols other than 3-amino-3-methyl-2-butanol, and performance additives (corrosion inhibitors, coupling agents, defoamers, and biocides), diluted metalworking fluids thereof, metalworking fluid concentrates pre-diluted with water, and pure metalworking fluids. Typically, 1 part by weight of metalworking fluid concentrate is diluted with about 4 to about 100 parts by weight of water (i.e., diluted to about 1% to about 20% by weight of its original concentration). In any embodiment, the dilution may be 10-50 parts by weight of water or even 15-30 parts by weight of water.

[0027] In any aspect and / or embodiment of this document, the metalworking fluid may also comprise an amino alcohol other than 3-amino-3-methyl-2-butanol (“other amino alcohols”), wherein exemplary other amino alcohols that may be included in the metalworking fluid composition of any embodiment of this document include, but are not limited to, 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or any combination of two or more of these. Compositions in any aspect of this document and / or embodiments may comprise other amino alcohols (e.g., 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or combinations of any two or more thereof) in amounts of at least about 0.01 wt%, at least about 0.02 wt%, at least about 0.03 wt%, at least about 0.04 wt%, at least about 0.05 wt%, at least about 0.06 wt%, at least about 0.07 wt%, at least about 0.08 wt%, at least about 0.09 wt%, at least about 0.1 wt%, at least about 0.25 wt%, at least about 0.5 wt%, at least about 0.75 wt%, at least about 1 wt%, at least about 1.5 wt%, at least about 2 wt%, at least about 2.5 wt%, at least about 3 wt% wt%, at least about 3.5 wt%, at least about 4 wt%, at least about 4.5 wt%, at least about 5 wt%, about 8 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, or including these values ​​and / or any range between any two of these values.Compositions in any aspect of this document and / or embodiments may comprise other amino alcohols (e.g., 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or combinations of any two or more thereof) in amounts not greater than about 0.01 wt%, not greater than about 0.02 wt%, not greater than about 0.03 wt%, not greater than about 0.04 wt%, not greater than about 0.05 wt%, not greater than about 0.06 wt%, not greater than about 0.07 wt%, not greater than about 0.08 wt%, not greater than about 0.09 wt%, not greater than about 0.1 wt%, not greater than about 0.25 wt%, not greater than about 0.5 wt%, not greater than about 0.75 wt%, not greater than about 1 wt%, and not greater than about 1.5 wt%. wt%, not greater than about 2 wt%, not greater than about 2.5 wt%, not greater than about 3 wt%, not greater than about 3.5 wt%, not greater than about 4 wt%, not greater than about 4.5 wt%, not greater than about 5 wt%, or including these values ​​and / or any range between any two of these values.

[0028] In any embodiment herein, the metalworking fluid may contain less than about 2 wt% of a secondary amine (e.g., 3-(ethylamino)-3-methylbut-2-ol, 2-(butylamino)ethanol, diethanolamine, diisopropanolamine (also known as 1-(2-hydroxypropylamino)prop-2-ol), and / or dicyclohexylamine). Therefore, in any embodiment herein, the amount of secondary amine contained in the composition may be less than about 2 wt%, less than about 1.5 wt%, less than about 1 wt%, less than about 0.5 wt%, or include these values ​​and / or any range between any two of these values. For example, in any embodiment herein, the composition may contain less than about 0.5 wt% of a secondary amine.

[0029] In any aspect and / or embodiment thereof, as previously described in this disclosure, the metalworking fluid may exhibit a bio-based content of 0% to 100% of 3-amino-3-methyl-2-butanol as determined by radiocarbon analysis according to ASTM D6866-24. Therefore, in any embodiment herein, the composition may exhibit a bio-based content of 3-amino-3-methyl-2-butanol (as determined using radiocarbon analysis according to ASTM D6866-24) of 0%, at least about 1%, at least about 5%, at least about 10%, at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, about 100%, or include these values ​​and / or any range between any two of these values. For example, the composition of any embodiment herein may exhibit a bio-based content of at least about 10% of 3-amino-3-methyl-2-butanol as determined using radiocarbon analysis according to ASTM D6866-24, or may exhibit a bio-based content of at least about 25% of 3-amino-3-methyl-2-butanol as determined using radiocarbon analysis according to ASTM D6866-24. Therefore, compositions of any aspect and / or embodiment herein may comprise renewable bio-based compounds (i.e., 3-amino-3-methyl-2-butanol) that exhibit low toxicity while providing comparable or superior performance compared to petroleum-based alternatives, and superior performance compared to existing renewable alternatives (e.g., NH3, NaOH).

[0030] In any aspect of this document and / or in any embodiment, the metalworking fluid has a pH of about 7 to about 12, for example, a pH of about 8 to about 10. Therefore, in any aspect of this document and / or in any embodiment, the metalworking fluid has a pH of about 7.0, about 7.5, about 8.0, about 8.5, about 9.0, about 9.5, about 10.0, about 10.5, about 11.0, about 11.5, about 12.0, or a range including these values ​​and / or any two of these values.

[0031] AMB in metalworking fluids The concentration of 3-amino-3-methyl-2-butanol in the metalworking fluid concentrate (i.e., before dilution) can be at least about 1 wt%. In some embodiments, the concentration of 3-amino-3-methyl-2-butanol is from about 1 wt% to about 20 wt%, for example, any value of about 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt%, 19 wt%, or 20 wt%, or a range between any two of the foregoing values ​​and including any two of the foregoing values. For example, in some embodiments, the concentration is from about 2 to about 12 wt%, or from about 3 to about 8 wt%. In the final diluted metalworking fluid, the use of pure 3-amino-3-methyl-2-butanol can be in the range of about 0.01 wt% or 0.02 wt% to about 2 wt%, for example 0.05 wt% to 1 wt%, or even about 0.1 wt% to about 0.5 wt%.

[0032] base oil Metalworking fluids (including concentrates) may contain base oils, which may be hydrocarbon oils or synthetic polymers or copolymers. Common examples of synthetic and non-synthetic base oils include, for example, mineral oils and synthetic polymers / copolymers. Specific examples of such oils include, but are not limited to, petroleum, deeply hydrotreated naphthenic and alkyl oils, synthetic hydrocarbons, polyalphaolefins, polyethylene glycol block copolymers, and vegetable oils. Typical amounts of oil in metalworking fluids range from about 0 wt% to about 90 wt%, for example, any value of about 0 wt%, 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, or 90 wt%, or between any two of the foregoing values ​​and including any two of the foregoing values. In some embodiments, the amount of soluble oil in the metalworking fluid is from about 30 wt% to about 90 wt%, including any value of about 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, or 90 wt%, or between any two of the aforementioned values ​​and including any two of the aforementioned values. In some embodiments, for example, the amount of deeply refined petroleum in the semi-synthetic metalworking fluid is from about 5 wt% to about 40 wt%, including any value of about 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, or 50 wt%, or between any two of the aforementioned values ​​and including any two of the aforementioned values. Synthetic metalworking fluids typically contain 0% base oil because lubrication is provided by synthetic lubricants (including synthetic polymers).

[0033] additive Various additives can be used in metalworking fluids to modify the properties of base oils, including emulsifiers, lubricants, carboxylates, corrosion inhibitors, metal passivators, coupling agents, defoamers, biocides, chelating agents, antifogging agents, dyes or colorants, or any combination of two or more of them.

[0034] emulsifier Metalworking fluids and concentrates (e.g., soluble oil metalworking fluids or semi-synthetic metalworking fluids) may contain emulsifiers to bridge the gap between oil and water. It is worth noting that some emulsifiers are also coupling agents; exemplary coupling agents are described later in this disclosure. Emulsifiers may be anionic, nonionic, or amphoteric in nature. Suitable emulsifiers include, but are not limited to: alkanolamides, alkylaryl sulfonates, alkylaryl sulfonic acids, amine oxides, amides and amine soaps, block copolymers, carboxylated alcohols, fatty acids, ethoxylated alcohols, ethoxylated alkylphenols, ethoxylated fatty amines, ethoxylated amides, ethoxylated fatty acids, ethoxylated fatty esters and oils (e.g., ethoxylated castor oil), ethoxylated phenols (e.g., nonylphenol ethoxylate), fatty amines and esters, glycerides, ethylene glycol esters, imidazolines and imidazoline derivatives, lignin and lignin derivatives, maleic anhydride or succinic anhydride, methyl esters, monoglycerides and their derivatives, naphthenic acids, olefin sulfonates, phosphate esters, polyalkylene glycols, etc. Polyethylene glycol, polyols, polymers (polysaccharides, acrylic acid, acrylamide), propoxylated and ethoxylated fatty acids, alcohols or alkylphenols, quaternary ammonium surfactants, sarcosine derivatives, soaps, sorbitol derivatives, sucrose and glucose esters and derivatives, sulfates and sulfonates of oils and fatty acids (e.g., sodium petroleum sulfonate), sulfates and sulfonates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, sulfates of fatty acid esters, sulfonates of dodecyl and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalenes, sulfonates of petroleum, sulfosuccinates, sulfosuccinates and derivatives, and tridecyl and dodecylbenzene sulfonic acids. Based on the total weight of the metalworking fluid, 25 wt% or less, for example, about 0.1 wt% to about 25 wt% of emulsifier can be used. Therefore, suitable amounts include any value of about 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 wt%, or between any two of the foregoing values ​​and a range including any two of the foregoing values. In any embodiment, the emulsifier may be present in an amount of about 0.1 wt% to about 20 wt% or about 1 wt% to about 15 wt%.

[0035] (Boundary and Extreme Pressure) Lubricants Two main types of lubrication in metalworking fluid processing are boundary lubrication and extreme pressure (EP) lubrication. Boundary lubrication involves separating moving surfaces by absorbing or adsorbing additives onto the surface to form a film of fluid lubricant, thereby reducing friction and heat. Boundary lubricants include greases, vegetable oils, esters, fatty acid esters, complex esters, polyol esters, fatty acids, tall oil fatty acids (TOFA), fatty acids and amino alkoxides (e.g., oleic acid AMB salt, other amino alkoxides), block polymers, and polyethylene glycols. EP lubricants are chemisorbed onto the surface to form a chemical layer that minimizes wear experienced when surfaces rub against each other. Extreme pressure lubricants include phosphate esters (e.g., zinc dialkyl dithiophosphate), chlorinated paraffins, chlorinated fatty acids, sulfurized greases, sulfurized fatty acids, sulfurized olefins, and peralkalized calcium sulfonate.

[0036] Polymer lubricant additives can provide two types of lubrication and can be used in synthetic and semi-synthetic metalworking fluids. These can consist of one or more of the following: block copolymers consisting of a central polyoxypropylene block and a polyoxyethylene chain at either end; block copolymers consisting of a central polyoxyethylene block and a polyoxypropylene chain at either end; tetrablock copolymers obtained by 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 materials of random copolymers of ethylene oxide and propylene oxide; water-soluble carboxylic acid esters of water-soluble polyoxyethylene or polyoxypropylene alcohols or such alcohols; alcohol-based base materials starting with any polyoxypropylene group having one terminal hydroxyl group; monobasic and dibasic acid esters; polyol esters; polyalkylene glycol esters; polyalkylene glycols grafted with organic acids; phosphate esters; polyisobutylene; polyacrylonitrile; polyacrylamide; polyvinylpyrrolidone; polyvinyl alcohol; and copolymers of acrylic acid or methacrylic acid and acrylates.

[0037] The metalworking fluid according to the present invention may contain one or more boundary lubricants in an amount of 0 wt% to about 40 wt%, more preferably about 1 to 25%, and most preferably about 2 to 15%. Ideally, the metalworking fluid according to the present invention may contain one or more boundary lubricants in an amount of at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, or 14% of the total weight of the metalworking fluid, and at most about 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, or 40% of the total weight of the metalworking fluid. The metalworking fluid according to the present invention may contain one or more extreme pressure lubricants in an amount of 0 to about 40% of the total weight of the metalworking fluid, more preferably about 5% to about 25% or less, and most preferably about 1% to about 5%. Ideally, the metalworking fluid according to the invention may contain one or more extreme pressure lubricants in an amount of at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, or 10% of the total weight of the metalworking fluid, and at most about 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, or 40% of the total weight of the metalworking fluid.

[0038] Carboxylates of amino alcohols, amides and esters Partially neutralized carboxylates of 3-amino-3-methyl-2-butanol (and optionally one or more other amino alcohols) provide a lipophilic moiety to polymeric lubricants, enabling them to form networks and be designed for larger droplet sizes. The pH of partial neutralization depends on the basic reagent used. Many of these carboxylates also provide boundary lubrication themselves. Carboxylic acids can be straight-chain or branched, saturated or unsaturated, fatty or oily, animal or plant-based, cis or trans-configured, dicarboxylic acids, tricarboxylic acids, esterified, amine, amide, or ethoxylated. Examples of carboxylic acids that can be used include: caproic acid, tartaric acid, caprylic acid, geraniic acid, nonanoic acid, isononanoic acid, caproic acid, neodecanoic acid, lauric acid, stearic acid, octadecanoic acid, arachidic acid, palmitic acid, hexadecanoic acid, erucic acid, oleic acid, arachidonic acid, linoleic acid, linolenic acid, myristic acid, behenic acid, docosahexaenoic acid, alpha-linolenic acid, docosahexaenoic acid, ricinoleic acid, butyric acid, lard, tallow, butter, coconut oil, palm oil, cottonseed oil, wheat germ oil, soybean oil, olive oil, corn oil, sunflower oil, and rapeseed oil / low-erucic acid rapeseed oil.

[0039] In the metalworking fluid of this technology, the carboxylate of 3-amino-3-methyl-2-butanol (and optionally one or more other amino alcohols) may be present in an amount of about 1 wt% to about 20 wt%, including any value of about 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt%, 19 wt% or 20 wt%, or between any two of the foregoing values ​​and a range including any two of the foregoing values.

[0040] Performance Additives A variety of performance additives may be used in metal processing fluids and their concentrates, including but not limited to corrosion inhibitors, metal deactivators, cobalt leaching inhibitors, coupling agents, defoamers, biocides, chelating agents, antifogging agents, dyes or colorants, or any combination of two or more of them.

[0041] Corrosion inhibitors act as rust inhibitors and metal passivators by preventing oxygen and acids from entering the metal and corroding the surface. Examples of corrosion inhibitors include medium to high molecular weight sodium petroleum sulfonates, 1,2,4-thiadiazoles, alkanolamides, and amino alkoxides (3-amino-3-methyl-2-butanol salts, and optionally one or more other amino alkoxides) of various organic and inorganic acids (including TOFA, mixed dicarboxylic acids, nonanoic acid, neodecanoic acid, sebacic acid, oleic acid, boric acid, and many other acids known to those skilled in the art). Corrosion inhibitors may be present in the metalworking fluids of this art in amounts from about 0.05 wt% to about 10 wt%. Suitable amounts include any value of about 0.05 wt%, 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1 wt%, 1.5 wt%, 2 wt%, 2.5 wt%, 3 wt%, 3.5 wt%, 4 wt%, 4.5 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, or 10 wt%, or between any two of the foregoing values ​​and ranges including any two of the foregoing values. In any embodiment, the corrosion inhibitor may be present in amounts of about 0.1 wt% to about 2 wt% or even 1 wt%.

[0042] Metal passivators and cobalt leaching inhibitors may be included to control copper corrosion of electrical contacts in machinery and / or prevent corrosion of brass and bronze alloys. Cobalt leaching inhibitors protect the integrity of sintered carbide tools. "Carbide" tools include those made by pressing and sintering powdered metallic iron carbides together with a cobalt binder.

[0043] Coupling agents are commonly used to improve the stability of emulsions by being soluble in both oil and aqueous phases. These include glycols (e.g., propylene glycol and hexanediol), glycol ethers (e.g., propylene glycol n-butyl ether), higher alcohols (e.g., hexanol), fatty alcohols (e.g., tridecanoic acid), and fatty acids (octanoic acid, isononanoic acid, and neodecanoic acid). Coupling agents may be present in the metalworking fluids of this technology in amounts from about 0.05 wt% to about 10 wt%. Suitable amounts include any value of about 0.05 wt%, 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1 wt%, 1.5 wt%, 2 wt%, 2.5 wt%, 3 wt%, 3.5 wt%, 4 wt%, 4.5 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, or 10 wt%, or between any two of the foregoing values ​​and ranges including any two of the foregoing values. In any embodiment, the coupling agent may be present in an amount of about 0.1 wt% to about 2 wt% or even 1 wt%.

[0044] Defoamers affect surface tension. They are dispersed but not completely dissolved in metalworking fluid concentrates or compositions and reside on surfaces during use. Defoamers include silicones, reactive silicones, organically modified siloxanes, polyalkylene imides, and waxes. Exemplary defoamers include polyethyleneimine, alkyl polysiloxanes (e.g., dimethyl polysiloxane, diethyl polysiloxane, dipropyl polysiloxane, methylethyl polysiloxane, dioctyl polysiloxane, diethyl polysiloxane, methylpropyl polysiloxane, dibutyl polysiloxane, and bis(dodecyl) polysiloxane); organophosphorus compounds (e.g., tributyl phosphate, tributoxyethyl phosphate, or triphenyl phosphite or mixtures thereof); and copolymers of polyepoxides (ethylene oxide, propylene oxide, and butane oxide). Defoamers may be present in metalworking fluids at about 0.01 wt% to about 2 wt%. Therefore, suitable amounts include any value of about 0.01 wt%, 0.05 wt%, 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1 wt%, 1.25 wt%, 1.5 wt%, 1.75 wt%, or 2 wt%, or between any two of the aforementioned values ​​and ranges including any two of the aforementioned values.

[0045] Biocides are used for microbial control in metalworking fluids. They can be used in metalworking fluids. And it can be used in the metalworking fluid of this technology. Biocides for microbial control (e.g., bacteria and / or fungi) include, but are not limited to, triazine, isothiazolinone, dinitromorpholine, p-chloro-m-cresol, phenolic resins, bromonitroban, butyl carbamate, or combinations of any two or more of these. Exemplary active concentration ranges of biocides in metal processing fluids and concentrates vary depending on the biocide used, but can be readily determined by those skilled in the art. For example, in any embodiment of this technology containing a biocide, the concentration may be at least about 0.01 wt% and / or may not exceed about 5 wt%. Suitable concentrations include any value of about 0.01 wt%, 0.05 wt%, 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1 wt%, 1.5 wt%, 2 wt%, 2.5 wt%, 3 wt%, 3.5 wt%, 4 wt%, 4.5 wt%, or 5 wt%, or a range between any two of the foregoing values ​​and including any two of the foregoing values. In any embodiment, the biocide may be present in an amount of about 0.01 wt% to about 3 wt% or about 4 wt%.

[0046] For specific biocides, for example, 1,3,5-tris(2-hydroxyethyl)-triazine is typically used at an effective concentration of 0.76 to 3%, particularly 1.1 to 3% by weight; iodopropynyl butylcarbamate is used at a concentration of 0.2 to 0.6%, for example 0.3 to 0.6%; 1,2-benzisothiazolinone is used at a concentration of 0.08 to 0.36%, for example 0.16 to 0.36%; and 4,4-dimethyloxazolidine is used at a concentration of 0.78 to 3.1%, for example 1.2%. It is used in the range of up to 3.1%; 7-ethylbicyclooxazolidine is used in the range of 1 to 4%, especially 1.5 to 4%; the combination of 4-(2-nitrobutyl)morpholine and 4,4'-(2-ethyl-2-nitrotrimethylene)dimorpholine is used in the range of 1 to 4%, for example 1.5 to 3%; and the combination of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one is used in the range of 0.01% to 0.08%, for example 0.05% to 0.08%.

[0047] Amines and amino alcohols other than AMB Amines and amino alcohols are widely used to neutralize critical acidic functional components (emulsifiers, lubricant additives, corrosion inhibitors, etc.) and to develop and maintain alkaline pH > 7 and provide buffering capacity. This ensures a higher pH, which helps improve the biocompatibility of metalworking fluid concentrates and diluents and protects tools and parts from corrosion. The choice of amino alcohol can significantly affect performance, including but not limited to providing pH stability and forming amino alkoxides (anionic emulsifier salts) that improve emulsifier efficiency, boundary and EP lubrication (acidic lubricant salts).

[0048] Alkalinity, pH, and bacteria affect the corrosive properties of lubricants, so products are formulated to maintain these properties accordingly. A decrease in pH is a good indicator of bacterial presence and potential rusting. Corrosion control of ferrous alloys (e.g., dibasates), reduction of corrosion and staining of aluminum alloys (e.g., acid phosphates), improved tool life (low metal leaching, e.g., cobalt from carbide tools), and synergistic effects with biocides to provide fluid life (microbial resistance) are all important considerations. The most commonly used amino alcohols are primary and tertiary amines. Ideally, metalworking fluids should be free of secondary amines (e.g., free of diethanolamine (DEA)).

[0049] Therefore, as previously described herein, in any aspect and / or embodiment thereof, the metalworking fluid composition may also comprise an amino alcohol other than 3-amino-3-methyl-2-butanol (“other amino alcohols”), wherein exemplary other amino alcohols that may be included in the metalworking fluid composition of any embodiment herein include, but are not limited to, 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or any combination of two or more thereof. Compositions in any aspect of this document and / or embodiments may comprise other amino alcohols (e.g., 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or combinations of any two or more thereof), in amounts of at least about 0.01 wt%, at least about 0.02 wt%, at least about 0.03 wt%, at least about 0.04 wt%, at least about 0.05 wt%, at least about 0.06 wt%, at least about 0.07 wt%, at least about 0.08 wt%, at least about 0.09 wt%, at least about 0.1 wt%, at least about 0.25 wt%, at least about 0.5 wt%, at least about 0.75 wt%, at least about 1 wt%, at least about 1.5 wt%, at least about 2 wt%, at least about 2.5 wt%. wt%, at least about 3 wt%, at least about 3.5 wt%, at least about 4 wt%, at least about 4.5 wt%, at least about 5 wt%, about 8 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, or including these values ​​and / or any range between any two of these values.Compositions in any aspect of this document and / or embodiments may comprise other amino alcohols (e.g., 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or any combination of two or more thereof), in amounts not exceeding about 0.01 wt%, not exceeding about 0.02 wt%, not exceeding about 0.03 wt%, not exceeding about 0.04 wt%, not exceeding about 0.05 wt%, not exceeding about 0.06 wt%, not exceeding about 0.07 wt%, not exceeding about 0.08 wt%, not exceeding about 0.09 wt%, not exceeding about 0.1 wt%, not exceeding about 0.25 wt%, not exceeding about 0.5 wt%, not exceeding about 0.75 wt%, not exceeding about 1 wt%, and not exceeding about 1.5 wt%. wt%, not greater than about 2 wt%, not greater than about 2.5 wt%, not greater than about 3 wt%, not greater than about 3.5 wt%, not greater than about 4 wt%, not greater than about 4.5 wt%, not greater than about 5 wt%, or including and / or any range between any two of these values.

[0050] Examples provided herein are intended to illustrate the advantages of the present technology and further assist those skilled in the art in preparing or using compositions of the present technology. Examples are also provided herein to illustrate the present technology more fully. These examples should not in any way be construed as limiting the scope of the present technology, which is defined by the appended claims. Examples may include or combine any variations, layers, or aspects of the present technology described above. These variations, layers, or aspects may also each further include or combine any or all of the other variations, layers, or aspects of the present technology.

[0051] Example General information The IUPAC names and abbreviations of the compounds tested in this paper are provided below. Example 1. Synthesis of renewable bio-based 3-amino-3-methyl-2-butanol Synthesis of renewable 2-nitropropane (2NP). Titanium silicate zeolite-1 (5.0 g, TS-1, ACS material), bio-based acetone (29 g, 0.5 mol, Millipore Sigma), and 10% ammonia (170.3 g, 1.0 mol) were placed in a three-necked flask equipped with a condenser. The mixture was heated to 60–65 °C, and then 35% aqueous hydrogen peroxide solution (145.7 g, 1.5 mol) was added dropwise over a 2-hour period while maintaining the internal temperature of the reaction mixture below 70 °C. After the addition of hydrogen peroxide, the mixture was maintained at 65 °C for 2–4 hours until all intermediate oximes had reacted according to GC. The reaction mixture was cooled to room temperature and filtered. 2NP was separated from the aqueous layer using a separatory funnel and then dried over anhydrous sodium sulfate. The separation yield of 2NP was 75%, with a purity of 97%.

[0052] The synthesis of renewable 3-nitro-3-methyl-2-butanol (NMB) and renewable 3-amino-3-methyl-2-butanol (AMB) become. 2-Nitropropane (1 mol, 97%, from a previous step) and bioacetaldehyde (1 mol, 99%, Millipore Sigma) were added to triethylamine (0.02 mol, Millipore Sigma) in methanol, while maintaining the temperature below 50°C. The mixture was stirred overnight at ambient temperature. GC-FID analysis showed a conversion of 91% from 2NP to NMB. The reaction mixture was then fed into a stainless steel reactor containing Raney nickel (10 wt%) and methanol at 50–80°C with 650 psi hydrogen. After the reaction was complete, the mixture was separated from the catalyst and distilled at ambient pressure. The fraction containing the desired product was collected at 158–162°C and recovered as a colorless liquid. According to GC-FID analysis (capillary column: 30 m fused silica, (5% phenyl)-methylpolysiloxane bonded phase column with 0.25 mm inner diameter and 1.0 μm film thickness; carrier gas flow rate: 1 mL / min helium; gas chromatograph: Agilent model 7890, series II), the separation yield was 70% and the purity was 96%.

[0053] Example 2. Purification and dilution of 3-amino-3-methyl-2-butanol A portion of the product from Example 1 was crystallized from diethyl ether to provide a purity of 99.6%. A dilution was prepared by mixing AMB with deionized water at 40°C. The resulting solution was cooled until the sample solidified. Table 1 below shows the melting point data for AMB samples at different purity levels and dilutions. Sample 1 is the distilled product from Example 1. Sample 2 is Sample 1 with water. Sample 3 is the crystalline form of the product from Example 1. Sample 4 is Sample 3 with water. Higher levels of impurities and water provide lower melting points.

[0054] Table 1. Properties of 3-amino-3-methyl-2-butanol with different purities and water contents The isolated product can be diluted with water to 90% activity to improve stability.

[0055] Example 3. Comparison of cobalt leaching tests of AMB with AMP, MIPA, and MEA The effectiveness of AMB in minimizing and / or reducing cobalt leaching from cobalt-containing metalworking tools (e.g., those containing cobalt-bonded tungsten carbide particles) compared to AMP, monoisopropanolamine (“MIPA”), and monoethanolamine (“MEA”) was evaluated by a cobalt leaching test. Specifically, a 1% aqueous solution of AMB, AMP, MIPA, or MEA and 1500 ppm of fine cobalt powder were added to each test sample. The pH of each sample was adjusted to approximately 9.5 using acetic acid. The samples were then stirred for 24 hours, filtered, and analyzed using inductively coupled plasma (ICP) emission spectrometry to measure the amount of leached cobalt (in ppm), the results of which are provided in Table 2 below and in… Figure 1 The diagram shows that AMB provided significantly better cobalt leaching control compared to MIPA and MEA, and comparable cobalt leaching control compared to AMP.

[0056] Table 2. Results of cobalt leaching test Example 4. Exemplary low-oil semi-synthetic metalworking fluid composition containing phosphate ester / salt. A low-oil semi-synthetic metalworking fluid containing phosphate esters / salts and having the composition shown in Table 3 below was prepared, exhibiting a target pH of 9.5 when diluted to a 5% working solution. Compositions Q and R are comparative compositions, while composition S contains AMB according to the present technology. Each composition was prepared according to the following scheme.

[0057] 1. Add 1-5 (water, dicarboxylic acid, and one of AMP, MEA, or AMB) at room temperature and mix until dissolved (clear), 5-10 minutes.

[0058] 2. In a separate container, heat 6 (naphthenic oil) and 7 (sodium sulfonate) to 100°C for 5-10 minutes to disperse the sodium sulfonate in the naphthenic oil. Cool or place in an ice bath to room temperature. Then add 8-12 to 6 and 7 (oil phase) at room temperature. Mix for 5-10 minutes until homogeneous.

[0059] 3. Add the oil phase (6-12) to the aqueous phase (1-5) at room temperature. Mix for 5-10 minutes until homogeneous.

[0060] 4. While mixing, add 13 and 14 dropwise at room temperature. Mix for 30 minutes to 1 hour, until a stable emulsion is formed.

[0061] 5. Wait 24 hours for the pH to reach the level found in distilled water diluted at 5%.

[0062] Table 3. QS of Low-Oil Semi-Synthetic Metalworking Fluid Compositions Containing Phosphate Esters / Salts Example 5. Exemplary low-oil semi-synthetic metalworking fluid composition without phosphate esters / salts A low-oil semi-synthetic metalworking fluid composition having the components shown in Table 4 (all components are in wt%) was prepared according to a similar scheme provided in Example 4, but phosphate esters / salts were omitted. Compositions T, U, and V are comparative compositions, while composition W contains AMB according to the present technology.

[0063] Table 4. Low-oil semi-synthetic metalworking fluid compositions (T, V, W, phosphate ester / salt-free) Example 6. Performance testing of metalworking fluids containing 3-amino-3-methyl-2-butanol The aluminum staining ability of the metalworking fluid compositions Q, R, and S in Example 4 was determined using the following procedure: 1. Prepare a 5% metalworking fluid dilution of each fluid in water with a hardness of 200 ppm. 2. Immerse the freshly ground (dry-grinded) aluminum sample in 35 mL of diluted metalworking fluid.

[0064] 3. Seal in a wide-mouth bottle with a Teflon seal and age in an oven at 40°C for 24 hours.

[0065] 4. Rinse the sample in DI water and evaluate the staining visually.

[0066] *200 ppm hardness water is prepared by: (a) adding 0.222 g CaSO4●2(H2O) and 0.085 g MgSO4 to a 1-liter volumetric flask; (b) filling the flask to the mark with DI water; (c) mixing for 24 hours.

[0067] The results of the aluminum staining control test using compositions Q, R, and S are shown in Figure 2In the medium, AMB exhibited less staining and less corrosion on aluminum 2024, 6061, and 7075 than AMP and MEA.

[0068] Corrosion was tested using the following modified cast iron chips test according to the IP287 standard with compositions Q, R, and S: 1. Sieve the iron filings through an approximately 18-mesh sieve to remove fine particles.

[0069] 2. Use tap water with a hardness of 100-350 ppm.

[0070] 3. Prepare diluents up to 5% by weight.

[0071] 4. Place the filter paper in the petri dish lid and use a pencil to draw a 3.5cm square mark using a stencil.

[0072] 5. Weigh 2g of IP287 iron filings and place them in a 3.5 cm square on the filter paper in the petri dish using the model.

[0073] 6. Cover the iron filings with 2 mL of diluent; ensure all fragments are thoroughly wetted.

[0074] 7. Cover with the bottom of the petri dish as a lid. Let the iron filings and fluid stand for about 2 hours; a humidity chamber set at 25°C and 65% relative humidity (RH) can be used.

[0075] 8. After about 2 hours, remove the filter paper from the petri dish and rinse it with water to remove any debris.

[0076] 9. Place the rinsed filter paper back into the petri dish lid and let it air dry; dispose of used consumables; results can be seen immediately.

[0077] 10. Visually assess corrosion.

[0078] The corrosion results of AMP, MEA, and AMB (combinations Q, R, and S) on iron are shown in... Figure 3 In the middle, AMB demonstrated performance comparable to or better than AMP.

[0079] Example 7. High-oil semi-synthetic metalworking fluid composition A high-oil semi-synthetic metalworking fluid with the composition shown in Table 5 was prepared according to a similar scheme provided in Example 5, but with a higher amount of base oil. Compositions X, Y, and Z are comparative compositions, while composition AA contains 3-amino-3-methyl-2-butanol (“AMB”) according to the present technology.

[0080] Table 5. High-oil semi-synthetic metalworking fluid composition X-AA Note: 3A4O = 3-amino-4-octanol; AEPD = 2-amino-2-ethyl-1,3-propanediol Example 8. Exemplary and comparative surface tension of metalworking fluids A semi-synthetic drawing fluid composition was prepared. Specifically, mineral oil and benzotriazole were combined in the amounts shown in Table 6 below, and then heated to approximately 40°C to approximately 50°C while continuously stirring with a magnetic stir bar for approximately 30 minutes. Sodium petroleum sulfonate (see Table 6) was then added to the mixture under continuous stirring, and the mixture was maintained at approximately 40°C to approximately 50°C for approximately 10 to 15 minutes. The following substances were then added in the amounts shown in Table 6: (i) AMP or AMB, (ii) 3A4O, (iii) Triethanolamine (“TEA”), methyldiethanolamine (“MDEA”), AEPD or tris(hydroxymethyl)aminomethane (“TRIS”), and (iv) tert-decanoic acid (versatic acid), Simultaneously, the mixture is continuously stirred at approximately 40°C to approximately 50°C. The resulting stirred mixture is then cooled to approximately 23°C. C, then add trimethylolpropane trioleate (“TMPTO”) and stir for about 10 minutes. Then add the remaining components shown in Table 6 in sequence, with an interval of about 5 minutes between each addition and stirring continuously. The last two components added are benzisothiazolinone (“BIT”), followed by Foam Ban HP 750.

[0081] Then, each formulation was diluted to 5% with 200 ppm hardness water (according to NF-T 60-188). That is, for 1 part of the formulation, add 19 parts of water with a hardness of 200 ppm. This provides the final compositions for testing. The surface tension of each final composition was then measured using a Krüss K20. The results are provided in Table 7, showing the relationship between the percentage of emulsifier (before dilution) and surface tension for each drawing fluid. Figure 4 In the study, it was found that semi-synthetic drawing fluid compositions containing AMB required less emulsifier to achieve similar surface tension than those containing AMP.

[0082] Table 6. Fiber-drawing fluid compositions containing AMB and AMP (before dilution) Table 7. Results of the drawing fluid Example 9. Effectiveness of buffering against acidification of metal processing fluids caused by dissolved CO2. The effectiveness of 3-amino-3-methyl-2-butanol in buffering acidification caused by dissolved CO2 was evaluated compared with AMP, MIPA, and MEA. In this experiment, an apparatus was constructed comprising a 1-liter flask vented to atmosphere, into which a pH probe and a gas line were inserted. The gas line was supplied with pressurized CO2, was adjustable, and equipped with a flow meter and diffuser. A 1-liter aqueous solution of 0.1 M amine (3-amino-3-methyl-2-butanol (“AMB”), AMP, MIPA, or MEA) was prepared by gentle stirring while being pumped at 30 cm⁻¹. 3 CO2 was bubbled into the solution at a rate of 1000 cm³ / min. pH was recorded every 10 seconds for 100 minutes. The results of these experiments are summarized in Table 8 below. The results showed that, compared to each of AMP, MIPA, or MEA, AMB was significantly more effective at bubbling CO2 at a volume of 2700 cm³ / min. 3 At that time, it can provide significantly better acidification buffering capacity.

[0083] Table 8. Buffering Results Equivalent implementation method While certain embodiments have been described and illustrated, modifications, equivalent substitutions, and other types of alterations can be made to the compositions of the present technology as described herein by those skilled in the art upon reading the foregoing specification. Each aspect and embodiment described above may also include or combine variations or aspects of these other aspects and embodiments disclosed therein.

[0084] This technology is not limited to the specific aspects described herein, which are intended as separate illustrations of individual aspects of this technology. Many modifications and variations can be made to this technology without departing from the spirit and scope of the invention, as will be apparent to those skilled in the art. Based on the foregoing description, functionally equivalent methods within the scope of this technology, in addition to those listed herein, will be apparent to those skilled in the art. Such modifications and variations are intended to fall within the scope of the appended claims. It should be understood that this technology is not limited to specific methods, reagents, compounds, or compositions, although they can vary. It should also be understood that the terminology used herein is for descriptive purposes only and is not intended to be limiting. Therefore, this specification should be considered exemplary only, and the breadth, scope, and spirit of this technology are indicated solely by the appended claims, the definitions therein, and any equivalents thereof.

[0085] The embodiments exemplarily described herein may be suitably implemented without the presence of any one or more elements or limitations not specifically disclosed herein. Therefore, terms such as “comprising,” “including,” and “containing” should be interpreted broadly and without limitation. Furthermore, the terms and expressions used herein have been used as descriptive rather than restrictive terms, and their use is not intended to exclude any equivalents of the features shown and described or portions thereof, but it should be recognized that various modifications may be made within the scope of the claimed technology. Moreover, the phrase “consistently composed of” should be understood to include those specifically listed elements as well as additional elements that do not materially affect the essential and novel features of the claimed technology. The phrase “consisting of” excludes any unspecified elements.

[0086] Furthermore, when features or aspects of this disclosure are described in accordance with the Markush Group, those skilled in the art will recognize that this disclosure is also described in accordance with any individual member or subgroup of the Markush Group. Each of the narrower classes and subgroups falling within the general disclosure also constitutes part of this technology. This includes a general description of technologies with accompanying conditions or negative limitations from that class, regardless of whether the removed content is specifically stated herein.

[0087] As those skilled in the art will understand, for any and all purposes, especially for the purpose of providing a written description, all scopes disclosed herein also encompass any and all possible subscopes and combinations thereof. Any listed scope can be simply considered sufficiently descriptive and such that the same scope can be decomposed into at least two, three, four, five, ten, etc., equal parts. As a non-limiting example, each scope discussed herein can be readily decomposed into a lower third, a middle third, and an upper third, etc. As those skilled in the art will also understand, all language such as “up to,” “at least,” “greater than,” “less than,” etc., includes the listed numbers and refers to a scope that can subsequently be decomposed into subscopes as described above. Finally, as those skilled in the art will understand, a scope includes each individual member.

[0088] All publications, patent applications, granted patents, and other documents (e.g., journals, articles, and / or textbooks) mentioned in this specification are incorporated herein by reference as if each individual publication, patent application, granted patent, or other document were specifically and individually identified as being incorporated herein by reference in its entirety. Definitions contained in the text incorporated by reference are excluded where they contradict the definitions in this disclosure.

[0089] This technology may include, but is not limited to, the features and combinations thereof described in the paragraphs numbered below. It should be understood that the following paragraphs should not be construed as limiting the scope of the appended claims, or requiring that all such features be included in these claims: A. A metalworking fluid comprising 3-Amino-3-methyl-2-butanol; Approximately 0.1 wt% or more of water; and Optional base oil.

[0090] B. The metalworking fluid according to paragraph A, wherein the metalworking fluid comprises about 0.01 wt% to about 20 wt% of 3-amino-3-methyl-2-butanol, and optionally wherein the metalworking fluid comprises about 10 wt% to about 50 wt% of base oil.

[0091] C. The metalworking fluid according to paragraph A or B, wherein the metalworking fluid comprises about 0.01 wt% to about 10 wt% of 3-amino-3-methyl-2-butanol.

[0092] D. The metalworking fluid according to any one of paragraphs A and C, wherein the metalworking fluid is a soluble oil, semi-synthetic, or synthetic.

[0093] E. The metalworking fluid according to any one of paragraphs A and D, wherein the base oil comprises petroleum oil, hydrotreated naphthenic oil, hydrotreated alkane oil, synthetic hydrocarbon, polyalphaolefin, polyethylene glycol block copolymer, vegetable oil, hydrotreated vegetable oil, complex ester, polyol ester, refining base oil, or any combination of two or more thereof.

[0094] F. The metalworking fluid according to any one of paragraphs A, E, and E, wherein the metalworking fluid further comprises an emulsifier, a corrosion inhibitor, a biocide, a neutralizer, or a combination of any two or more thereof.

[0095] G. The metalworking fluid as described in paragraph F, wherein the metalworking fluid contains a nonionic emulsifier.

[0096] H. The metalworking fluid according to paragraph G, wherein the nonionic emulsifier comprises ethoxylated alcohols, alkanolamides, esters, or any combination of two or more thereof.

[0097] I. The metalworking fluid according to any one of paragraphs FH, wherein the metalworking fluid comprises an anionic emulsifier.

[0098] J. The metalworking fluid according to paragraph I, wherein the anionic emulsifier comprises sodium sulfonate, fatty acid salt, succinate, succinic anhydride, polymer emulsifier, or any combination of two or more thereof.

[0099] K. The metalworking fluid according to paragraph J, wherein the polymer emulsifier comprises polyethylene glycol.

[0100] L. A metalworking fluid according to any one of paragraphs FK, wherein the metalworking fluid comprises a corrosion inhibitor, the corrosion inhibitor comprising one or more of the following: phosphate esters, sodium sulfonate, thiadiazole, alkanolamide, amino alcohols other than 3-amino-3-methyl-2-butanol (“other amino alcohols”), 3-amino-3-methyl-2-butanol salts, other amino alcohol salts, tall oil fatty acids (TOFA), diacids, or any combination of two or more of these.

[0101] M. A metalworking fluid according to any one of paragraphs FL, wherein the metalworking fluid contains a biocide, the biocide comprising a mixture of biocide compounds exhibiting antibacterial and antifungal effects.

[0102] N. The metalworking fluid according to any one of paragraphs AM, wherein the metalworking fluid is a concentrate to be diluted with water to about 1% to about 20% of its original concentration.

[0103] O. The metalworking fluid according to any one of paragraphs AN further comprises one or more additives selected from: colorants; viscosity modifiers; lubricants, buffers, antioxidants, coupling agents, defoamers, antifogging agents, or any combination of two or more of these.

[0104] P. The metalworking fluid according to any one of paragraphs AO further comprises a neutralizing agent.

[0105] Q. The metalworking fluid according to paragraph P, wherein the neutralizing agent comprises one or more of a metal hydroxide, an alkylamine, or another amino alcohol.

[0106] R. The metalworking fluid according to paragraph P or Q, wherein the neutralizing agent comprises one or more of the following: monoisopropanolamine (MIPA), diethylene glycolamine (DGA), MEA (monoethanolamine), TEA (triethanolamine), 2-amino-2-methyl-1-propanol (AMP), 2-amino-1-butanol (2AB), 2-amino-2-ethyl-1,3-propanediol (AEPD), methyldiethanolamine (MDEA), tris(hydroxymethyl)aminomethane (TRIS), dicyclohexylamine (DCHA), 3-amino-4-octanol (3A4O), or any combination of two or more of them.

[0107] S. The metalworking fluid according to any one of paragraphs LR, wherein the other amino alcohol comprises one or more of the following: 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or any combination of two or more thereof.

[0108] T. A metalworking fluid according to any one of paragraphs LS, wherein the metalworking fluid comprises at least about 0.01 wt% of the other amino alcohols.

[0109] U. A metalworking fluid according to any one of paragraphs AT, wherein the metalworking fluid contains less than 2 wt% of a secondary amine.

[0110] V. The metalworking fluid according to any one of paragraphs AU, wherein the 3-amino-3-methyl-2-butanol has a bio-based content of at least about 10% as determined by radiocarbon analysis according to ASTM D6866-24.

[0111] W. The metalworking fluid according to any one of paragraphs AV, wherein the pH of the metalworking fluid is from about 7 to about 12, optionally wherein the pH of the metalworking fluid is from about 8 to about 10.

[0112] X. A metalworking fluid according to any one of paragraphs AW, wherein the metalworking fluid inhibits staining of non-ferrous metal workpieces in contact with the fluid during metalworking operations.

[0113] Y. A metalworking fluid according to any one of paragraphs AX, wherein the metalworking fluid inhibits cobalt leaching from cobalt-containing metal workpieces and / or carbide tools that come into contact with the fluid during metalworking operations.

[0114] Z. The metalworking fluid according to any one of paragraphs AY, wherein the metalworking fluid inhibits cooling and / or lubrication during metalworking operations.

[0115] AA. A method comprising adding an effective amount of 3-amino-3-methyl-2-butanol to a composition thereby increasing the pH of the composition, stabilizing the composition, and / or at least partially neutralizing acidic compounds in the composition, the composition comprising an aqueous dispersion containing a base oil and / or an emulsifier.

[0116] AB. A composition for use as a metalworking fluid and in metalworking applications, said composition comprising 3-Amino-3-methyl-2-butanol, about 30 wt% to about 99.99 wt%; and Water, approximately 0.01 wt% to approximately 70 wt%.

[0117] AC. Compositions for use according to paragraphs AB, wherein the composition further comprises an amino alcohol other than 3-amino-3-methyl-2-butanol (“other amino alcohols”).

[0118] AD. A composition for use according to paragraphs AB or AC, wherein the composition is used for metal removal, metal forming, metal cleaning and / or metal treatment, and optionally wherein the composition is used for cutting, grinding, drilling, turning, milling, machining, drawing, stamping, forming, rolling, cleaning and / or protecting (i) one or more metals, and / or (ii) one or more metal alloys.

[0119] AE. A composition for use according to paragraphs AC or AD, wherein the composition comprises about 0.01 wt% to about 60 wt% of the other amino alcohols.

[0120] AF. A composition for use according to any one of paragraphs AC-AE, comprising not more than 1 wt% of the other amino alcohols.

[0121] AG. A composition for use according to any one of paragraphs AB-AF, comprising about 70 wt% to about 95 wt% of 3-amino-3-methyl-2-butanol and about 5 wt% to about 30 wt% of water.

[0122] AH. A composition for use according to any one of paragraphs AC-AG, comprising about 90 wt% of 3-amino-3-methyl-2-butanol, about 10 wt% of water and less than 1 wt% of the other amino alcohols.

[0123] AI. A composition for use according to any one of paragraphs AB-AH, wherein the composition comprises less than 2 wt% of a secondary amine.

[0124] AJ. A composition for use according to any one of paragraphs AC-AI, wherein the composition further comprises not more than 5 wt% of the other amino alcohols.

[0125] AK. A composition for use according to any one of paragraphs AC-AJ, wherein the other amino alcohol is 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or any combination of two or more thereof.

[0126] AL. A composition for use according to any one of paragraphs AC-AK, wherein the composition comprises at least about 0.01 wt% of the other amino alcohol.

[0127] AM. A composition for use according to any one of paragraphs AC-AL, wherein, in addition to 3-amino-3-methyl-2-butanol, the composition further comprises 3-(ethylamino)-3-methylbut-2-ol.

[0128] AN. A composition for use according to any one of paragraphs AB-AM, wherein the composition exhibits a bio-based content of at least about 10% as determined by radiocarbon analysis according to ASTM D6866-24.

[0129] Other embodiments are set forth in the appended claims, and these claims are given the full scope of the equivalents.

Claims

1. A metalworking fluid, comprising 3-Amino-3-methyl-2-butanol; and Approximately 0.1 wt% or more of water.

2. The metalworking fluid according to claim 1, wherein the metalworking fluid further comprises a base oil.

3. The metalworking fluid of claim 2, wherein the metalworking fluid comprises about 10 wt% to about 50 wt% of base oil.

4. The metalworking fluid of claim 1, wherein the metalworking fluid comprises about 0.01 wt% to about 20 wt% of 3-amino-3-methyl-2-butanol.

5. The metalworking fluid of claim 1, wherein the metalworking fluid comprises about 0.01 wt% to about 10 wt% of 3-amino-3-methyl-2-butanol.

6. The metalworking fluid of claim 1, wherein the metalworking fluid is a soluble oil, semi-synthetic, or synthetic.

7. The metalworking fluid according to claim 1, wherein the base oil comprises petroleum oil, hydrotreated naphthenic oil, hydrotreated alkane oil, synthetic hydrocarbon, polyalphaolefin, polyethylene glycol block copolymer, vegetable oil, hydrotreated vegetable oil, complex ester, polyol ester, refining base oil, or any combination of two or more thereof.

8. The metalworking fluid of claim 1, wherein the metalworking fluid further comprises an emulsifier, a corrosion inhibitor, a biocide, a neutralizer, or a combination of any two or more thereof.

9. The metalworking fluid of claim 8, wherein the metalworking fluid comprises a nonionic emulsifier.

10. The metalworking fluid of claim 9, wherein the nonionic emulsifier comprises ethoxylated alcohols, alkanolamides, esters, or any combination of two or more thereof.

11. The metalworking fluid of claim 8, wherein the metalworking fluid comprises an anionic emulsifier.

12. The metalworking fluid of claim 11, wherein the anionic emulsifier comprises sodium sulfonate, fatty acid salt, succinate, succinic anhydride, polymer emulsifier, or any combination of two or more thereof.

13. The metalworking fluid of claim 12, wherein the polymer emulsifier comprises polyethylene glycol.

14. The metalworking fluid of claim 8, wherein the metalworking fluid comprises a corrosion inhibitor, the corrosion inhibitor comprising one or more of the following: phosphate esters, sodium sulfonate, thiadiazole, alkanolamide, amino alcohols other than 3-amino-3-methyl-2-butanol ("other amino alcohols"), 3-amino-3-methyl-2-butanol salts, other amino alcohol salts, tall oil fatty acids (TOFA), diacids, or any combination of two or more thereof.

15. The metalworking fluid of claim 8, wherein the metalworking fluid comprises a biocide, the biocide comprising a mixture of biocide compounds exhibiting antibacterial and antifungal effects.

16. The metalworking fluid of claim 1, wherein the metalworking fluid is a concentrate to be diluted with water to about 1% to about 20% of its original concentration.

17. The metalworking fluid according to claim 1 further comprises one or more additives, said additives being selected from: colorants; viscosity modifiers; lubricants, buffers, antioxidants, coupling agents, defoamers, antifogging agents, or any combination of two or more of these.

18. The metalworking fluid according to claim 1, further comprising a neutralizing agent.

19. The metalworking fluid of claim 18, wherein the neutralizing agent comprises one or more of a metal hydroxide, an alkylamine, or another amino alcohol.

20. The metalworking fluid of claim 18, wherein the neutralizing agent comprises one or more of the following: monoisopropanolamine (MIPA), diethylene glycolamine (DGA), MEA (monoethanolamine), TEA (triethanolamine), 2-amino-2-methyl-1-propanol (AMP), 2-amino-1-butanol (2AB), 2-amino-2-ethyl-1,3-propanediol (AEPD), methyldiethanolamine (MDEA), tris(hydroxymethyl)aminomethane (TRIS), dicyclohexylamine (DCHA), 3-amino-4-octanol (3A4O), or a combination of any two or more thereof.

21. The metalworking fluid of claim 14, wherein the other amino alcohol comprises one or more of the following: 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or any combination of two or more thereof.

22. The metalworking fluid of claim 14, wherein the metalworking fluid comprises at least about 0.01 wt% of the other amino alcohol.

23. The metalworking fluid of claim 1, wherein the metalworking fluid comprises less than 2 wt% of a secondary amine.

24. The metalworking fluid of claim 1, wherein the 3-amino-3-methyl-2-butanol has a bio-based content of at least about 10% as determined by radiocarbon analysis according to ASTM D6866-24.

25. The metalworking fluid of claim 1, wherein the metalworking fluid has a pH of about 7 to about 12.

26. The metalworking fluid of claim 1, wherein the metalworking fluid suppresses staining of non-ferrous metal workpieces in contact with the fluid during metalworking operations.

27. The metalworking fluid of claim 1, wherein the metalworking fluid inhibits cobalt leaching from cobalt-containing metal workpieces and / or carbide tools that come into contact with the fluid during metalworking operations.

28. The metalworking fluid of claim 1, wherein the metalworking fluid inhibits cooling and / or lubrication during metalworking operations.

29. A method comprising adding an effective amount of 3-amino-3-methyl-2-butanol to a composition to increase the pH of the composition, stabilize the composition, and / or at least partially neutralize acidic compounds in the composition, the composition comprising an aqueous dispersion containing a base oil and / or an emulsifier.

30. A composition for use as a metalworking fluid and in metalworking applications, said composition comprising... 3-Amino-3-methyl-2-butanol, about 30 wt% to about 99.99 wt%; and Water, approximately 0.01 wt% to approximately 70 wt%.

31. The composition for the use of claim 30, wherein the composition is used for cutting, grinding, drilling, turning, milling, machining, drawing, stamping, forming, rolling, cleaning and / or protecting metals and / or metal alloys.

32. The composition for use according to claim 30, wherein the composition further comprises an amino alcohol other than 3-amino-3-methyl-2-butanol ("other amino alcohols").

33. The composition for use according to claim 32, wherein the composition comprises about 0.01 wt% to about 60 wt% of the other amino alcohol.

34. The composition for use according to claim 32, comprising not more than 1 wt% of the other amino alcohol.

35. The composition for use according to claim 30, comprising about 70 wt% to about 95 wt% of 3-amino-3-methyl-2-butanol and about 5 wt% to about 30 wt% of water.

36. The composition for use according to claim 30, comprising about 90 wt% of 3-amino-3-methyl-2-butanol, about 10 wt% of water and less than 1 wt% of the other amino alcohols.

37. The composition for use according to claim 30, wherein the composition comprises less than 2 wt% of a secondary amine.

38. The composition for use according to claim 32, wherein the composition further comprises not more than 5 wt% of the other amino alcohol.

39. The composition for use according to claim 32, wherein the other amino alcohol is 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbut-2-ol, or a combination of any two or more thereof.

40. The composition for use according to claim 39, wherein the composition comprises at least about 0.01 wt% of the other amino alcohol.

41. The composition for use according to claim 39, wherein, in addition to 3-amino-3-methyl-2-butanol, the composition further comprises 3-(ethylamino)-3-methylbut-2-ol.

42. The composition for use according to claim 30, wherein the composition exhibits a bio-based content of at least about 10% as determined by radiocarbon analysis according to ASTM D6866-24.

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