Metalworking fluid compositions including amino alcohols and uses thereof

Abstract

The present technology relates generally to metalworking fluid compositions including a compound of Formula (I) where R1, R2, R3, and R4 are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4 is not H; and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms. For example, including a compound of Formula I in a metalworking fluid having a pH of at least about 7 may enhance the metalworking fluid's lubricating, cleaning, and / or handling properties by providing multi-metal corrosion inhibition, maintaining pH control, and / or stabilizing the metalworking fluid. When including a biocide, it may act synergistically with the biocide to inhibit microbial growth and disrupt existing biofilms, resulting in extended metalworking fluid life, reduced equipment wear, consistent part quality, and lower environmental load from fluid disposal.

Description

[0001] Atty. Dkt. No.: 109691-0801

[0002] METALWORKING FLUID COMPOSITIONS INCLUDING AMINO ALCOHOLS AND USES THEREOF

[0003] CROSS-REFERENCE TO RELATED APPLICATIONS

[0004] [1] This application claims the benefit of and priority to U.S. Provisional Appl. No. 63 / 695,308, filed September 16, 2024, the entire contents of which are incorporated herein by reference for any and all purposes.

[0005] TECHNICAL FIELD

[0006] [2] The present technology relates generally to metalworking fluid compositions including particular amino alcohols, useful for various metalworking operations (e.g., cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, protecting, and the like) of various metals. For example, including such particular amino alcohols in a metalworking fluid having a pH of at least about 7 enhances the metalworking fluid’s lubricating, cleaning, and handling properties by providing multi -metal corrosion inhibition, maintaining pH control, and stabilizing the metalworking fluid. When including a biocide, it may act synergistically with the biocide to inhibit microbial growth and disrupt existing biofilms, resulting in extended metalworking fluid life, reduced equipment wear, consistent part quality, and lower environmental load from fluid disposal.

[0007] BACKGROUND

[0008] [3] Many commonly used metalworking fluids are made of compositions using chemicals typically derived from non-renewable raw materials such as petroleum. For example, in addition to the petroleum distillates that are in neat oils and semisynthetic metalworking fluids and surfactants in metalworking fluids are also typically derived from petroleum sources, including neutralizing agents meant to neutralize acid groups present in the composition.

[0009] [4] Using non-renewable, petroleum-based raw materials contributes to overreliance on fossil fuels. This reliance on non-renewable petroleum-based raw materials contributes to environmental degradation such as air pollution, water pollution, and global warming.

[0010] -1-

[0011] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0012] Moreover, these fossil fuels are often supplied from politically unstable parts of the world, often raising humanitarian concerns.

[0013] [5] Thus, as explained above and in more details below, there remains a need for compositions for commonly used metalworking fluids made with natural, renewable starting materials that offer equivalent or better performance to current products.

[0014] SUMMARY

[0015] [6] The present disclosure is directed to compositions for metalworking fluids for various metalworking operations (e.g., cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, protecting, and the like) of various metals, such as aluminum, steel, and copper, where such compositions include a compound of Formula I wherein R1, R2, R3, and R4are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4is not H; and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Compounds of Formula I have several advantages, including their improved sustainability profile, demonstrated by their ability to be manufactured as a renewable, biobased compound (z.e., without relying on non-renewable petroleum -based raw materials) alongside their low toxicity (providing a safer alternative with reduced environmental and health impacts) while concurrently providing comparable or superior performance as compared to petroleum based alternatives and superior performance as compared to current renewable alternatives (e.g., NH3, NaOH). Thus, the presently disclosed technology overcomes common adoption barriers associated with renewable chemicals, such as poor performance and high cost, instead providing a high-performance, cost-effective solution with the potential for incorporating bio-based carbon.

[0016] -2-

[0017] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0018] BRIEF DESCRIPTION OF THE DRAWINGS

[0019] [7] FIG. 1 demonstrates stain control of metalworking fluids including AMP, MIPA, DGA, MEA, or 3A2P per the working examples. As illustrated by FIG. 1, 3A2P showed lower staining and less corrosion than AMP, MIPA, DGA, and MEA.

[0020] [8] FIG. 2 shows the results of ferrous corrosion by illustrative metalworking fluid containing AMP, MIPA, DGA, MEA, or 3 A2P as assessed by modified IP 287, CICT (cast iron chip test) at concentrations from 1.0 - 2.5%, per the working examples. 3A2P was found to provide comparable or better performance than AMP, MIPA, DGA, and MEA.

[0021] [9] FIG. 3 is a graph of the results of microbial challenging testing illustrative metalworking fluid with benzisothiazolinone biocide and containing AMP, MIPA, DGA, MEA, or 3 A2P as assessed by modified ASTM E2275, per the working examples. 3 A2P was found to have a bioresistance comparable or better than AMP, MIPA, DGA, and MEA.

[0022]

[0010] FIG. 4 is a graph of the results of microbial challenging testing illustrative metalworking fluid with mixed biocides and containing MIPA, DGA, MEA, or 3 A2P as assessed by modified ASTM E2275, per the working examples. 3A2P was found to have a better bioresistance than MIPA, DGA, and MEA.

[0023]

[0011] FIGS. 5A-5F show the results of quantifying biofilm formation on 347 stainless steel coupons in metalworking fluids containing AMP, MIPA, DGA, or 3 A2P, per the working examples. FIGS. 5A-5C show bacterial quantification for a 30 minute residence time and FIGS. 5D-5F show bacterial quantification for 1.5 hours residence time in the continuous phase of biofilm growth in the reactor. FIGS. 5 A and 5B show bacterial quantification from the metalworking fluid following biofilm formation, FIGS. 5C and 5D show bacterial quantification from coupon biofilm eluate, and FIGS. 5D and 5E show total average bacterial quantification from both metalworking fluid and coupon eluate. 3 A2P was found to have comparable or better antimicrobial efficacy than AMP, MIPA, and DGA.

[0024] DETAILED DESCRIPTION

[0025]

[0012] The following terms are used throughout as defined below.

[0026] -3-

[0027] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0028]

[0013] As used herein and in the appended claims, singular articles such as “a” and “an” and “the” and similar referents in the context of describing the elements (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. Recitation of ranges of values herein are merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or exemplary language (e.g., “such as”) provided herein, is intended merely to better illuminate the embodiments and does not pose a limitation on the scope of the claims unless otherwise stated. No language in the specification should be construed as indicating any non-claimed element as essential.

[0029]

[0014] As used herein, “about” will be understood by persons of ordinary skill in the art and will vary to some extent depending upon the context in which it is used. If there are uses of the term which are not clear to persons of ordinary skill in the art, given the context in which it is used, “about” will mean up to plus or minus 10% of the particular term - for example, “about 10 wt.%” would be understood to mean “9 wt.% to 11 wt.%.” It is to be understood that when “about” precedes a term, the term is to be construed as disclosing “about” the term as well as the term without modification by “about” - for example, “about 10 wt.%” discloses “9 wt.% to 11 wt.%” as well as disclosing “10 wt.%.”

[0030]

[0015] The phrase “and / or” as used in the present disclosure will be understood to mean any one of the recited members individually or a combination of any two or more thereof - for example, “A, B, and / or C” would mean “A or B or C; A and B; A and C; B and C; or the combination of A, B, and C.”

[0031]

[0016] The term "alkyl" refers to a group, whether alone or as part of another group (e.g., in dialkylamino), encompasses straight and branched chain aliphatic groups (ie., saturated hydrocarbyl chains), and, unless otherwise indicated, has 1-10, alternatively 1-8, or alternatively 1-6 alkyl carbon atoms. Representative alkyl groups include, without limitation, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl.

[0032] -4-

[0033] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0034] Unless otherwise indicated, the alkyl group is optionally substituted with 1, 2, or 3, e.g., 1 or 2, or even just 1, substituent(s) that are compatible with the compounds, monomers, and polymers described herein. In some embodiments, the alkyl group is unsubstituted.

[0035]

[0017] The term "alkoxy" refers to a group in which an oxygen attached to a saturated straight or branched chain alkyl group. Unless otherwise indicated, the alkoxy group contains 1 to 6 carbon atoms (e.g., methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, neopentyloxy, iso-pentyloxy, n-hexyloxy or isohexyloxy), and in any embodiments, 1 to 4 carbon atoms. In any embodiments, the alkoxy groups include methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy and tert-butoxy. In some embodiments, the alkoxy group is unsubstituted.

[0036]

[0018] Groups described herein having two or more points of attachment (z.e., divalent, trivalent, or polyvalent) within the compound of the present technology are designated by use of the suffix, “ene.” For example, divalent alkyl groups are alkylene groups, divalent cycloalkyl groups are cycloalkylene groups, and so forth. Substituted groups having a single point of attachment to the compound of the present technology are not referred to using the “ene” designation. Thus, e.g., chloroethyl is not referred to herein as chloroethylene.

[0037]

[0019] In general, “substituted” refers to an alkyl group, as defined above in which one or more bonds to a hydrogen atom contained therein are replaced by a bond to non-hydrogen or non-carbon atoms. Substituted groups also include groups in which one or more bonds to a carbon(s) or hydrogen(s) atom are replaced by one or more bonds, including double or triple bonds, to a heteroatom. In some embodiments, a substituted group is substituted with 1, 2, or 3 substituents. Examples of substituent groups include, but are not limited to, hydroxyl, amino, thiol, nitro, halo, ester, amido, carbonyl, or carboxylic acid. Unless otherwise indicated, the foregoing substituent groups are not themselves further substituted.

[0038]

[0020] Those of skill in the art will appreciate that compounds of the present technology may exhibit the phenomena of tautomerism, conformational isomerism, geometric isomerism and / or stereoisomerism. As the formula drawings within the specification and claims can represent only one of the possible tautomeric, conformational isomeric, stereochemical or geometric isomeric forms, it should be understood that the present technology encompasses

[0039] -5-

[0040] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 any tautomeric, conformational isomeric, stereochemical and / or geometric isomeric forms of the compounds having one or more of the utilities described herein, as well as mixtures of these various different forms.

[0041]

[0021] “ Tautomers” refers to isomeric forms of a compound that are in equilibrium with each other. The presence and concentrations of the isomeric forms will depend on the environment the compound is found in and may be different depending upon, for example, whether the compound is a solid or is in an organic or aqueous solution. For example, in aqueous solution, quinazolinones may exhibit the following isomeric forms, which are referred to as tautomers of each other:

[0042] As another example, guanidines may exhibit the following isomeric forms in protic organic solution, also referred to as tautomers of each other:

[0043] Because of the limits of representing compounds by structural formulas, it is to be understood that all chemical formulas of the compounds described herein represent all tautomeric forms of compounds and are within the scope of the present technology.

[0044]

[0022] Stereoisomers of compounds (also known as optical isomers) include all chiral, diastereomeric, and racemic forms of a structure, unless the specific stereochemistry is expressly indicated. Thus, compounds used in the present technology include enriched or resolved optical isomers at any or all asymmetric atoms as are apparent from the depictions. Both racemic and diastereomeric mixtures, as well as the individual optical isomers can be

[0045] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 isolated or synthesized so as to be substantially free of their enantiomeric or diastereomeric partners, and these stereoisomers are all within the scope of the present technology.

[0046]

[0023] The compounds of the present technology may exist as solvates, especially hydrates. Hydrates may form during manufacture of the compounds or compositions comprising the compounds, or hydrates may form over time due to the hygroscopic nature of the compounds. Compounds of the present technology may exist as organic solvates as well, including DMF, ether, and alcohol solvates, among others. The identification and preparation of any particular solvate is within the skill of the ordinary artisan of synthetic organic chemistry.

[0047]

[0024] Unless stated otherwise, all the molecular weight (z.e., molar mass) data, numberaverage molecular weight data Mn or weight-average molecular weight data Mw stated in the present description are molar masses, which can be determined by gel permeation chromatography (GPC).

[0048]

[0025] As used herein, “substantially free” refers to less than about 2 wt.% of the specified component based on the total weight of the composition. In some embodiments, the composition may include 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.

[0049] Amino Alcohol Compositions

[0050]

[0026] In an aspect, the present technology provides a composition for use in metalworking fluids and metalworking applications, such as for use in e.g., metal removal, metal forming, metal cleaning, and / or metal treating, and such as for use in e.g., cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, and / or protecting of a metal and / or metal alloy, where the composition includes about 30 wt.% to about 99.99 wt.% of a compound of Formula I

[0051] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 wherein

[0052] R1, R2, R3, and R4are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4is not H, and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms; about 0.01 wt.% to about 70 wt.% water; and optionally an amino alcohol other than the compound of Formula I (an “other amino alcohol”).

[0053]

[0027] In any embodiment herein, the composition may include the compound of Formula I in an amount of 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 any range including and / or in-between any two of these values. For example, the composition may include 85 wt.% to 95 wt.% of the compound of Formula I. In any embodiments, the compositions may include at least about 90 wt.% compound of Formula I.

[0054]

[0028] In any aspect and / or embodiment herein of the present technology, the compound of Formula I may be one or more of

[0055] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0056] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 optionally the composition may include the one or more of such compounds in a total amount of 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

[0057] 99.5 wt.%, about 99.9 wt.%, about 99.95 wt.%, about 99.99 wt.%, or any range including and / or in-between any two of these values. In any aspect or embodiment herein, it may be the compound of Formula I includes at least

[0058] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 may include no more than three of may include no more than two of may include only one of

[0059] -11-

[0060] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0061]

[0029] In any aspect and / or embodiment herein of the present technology, it may be the compound of Formula I is

[0062] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0063] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 herein, it may be the compound of Formula I is in any aspect or embodiment herein, it may be the compound of

[0064] Formula I is

[0065]

[0030] In any embodiments the compositions may include 0.01 wt.% to about 70 wt.% water.

[0066] Such compositions may be solutions at room temperature, e.g., a homogenous solution. In any embodiments, the compositions may include about 0.01 wt.%, about 0.05 wt.%, about

[0067] 0.1 wt.%, about 0.5 wt.%, about 1 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5

[0068] -14-

[0069] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 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.% water, 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.%, or any range including and / or in-between any two of these values. Thus, in any embodiment herein, the compositions may include 5 wt.% to 15 wt.% water or about 10 wt.% water. The water may be tap water, deionized water, distilled water, reverse osmosis (R.O.) water, or any combination thereof, including, e.g., double distilled water. In any embodiment herein, the purity and water content may be adjusted depending on the desired physical properties and end-use application.

[0070]

[0031] In any embodiment herein, water and / or an other amino alcohol may be included in the compositions including compounds of Formula I, e.g., to improve handling and / or modify performance characteristics. For example, addition of water to the compositions including compounds of Formula I may increase the flash point, reduce the freezing point, and / or reduce the viscosity of the composition. Exemplary other amino alcohols that may be included in compositions of any embodiment herein include, but are not limited to, 2- aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-methyl-l -propanol, 2-amino-

[0071] 1-butanol, 2-amino-2-ethyl-l,3-propanediol, 3-(ethylamino)pentan-2-ol, 3-amino-3-methyl-2- butanol, or a combination of any two or more thereof. The composition of any embodiment herein may include an other amino alcohol (e.g., 2-aminoethanol, triethanolamine, 1-amino-

[0072] 2-propanol, 2-amino-2-m ethyl- 1 -propanol, 2-amino-l -butanol, 2-amino-2-ethyl-l,3- propanediol, 3-(ethylamino)pentan-2-ol, 3-amino-3-methyl-2-butanol, or a combination of any two or more thereof) in amount 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.%, 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

[0073] -15-

[0074] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 wt.%, about 60 wt.%, or any range including and / or in-between any two of these values. The composition of any embodiment herein may include an other amino alcohol (e.g., 2- aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-methyl-l -propanol, 2-amino- 1-butanol, 2-amino-2-ethyl-l,3-propanediol, 3-(ethylamino)pentan-2-ol, 3-amino-3-methyl-2- butanol, or a combination of any two or more thereof) in amount of not more than about 0.01 wt.%, not more than about 0.02 wt.%, not more than about 0.03 wt.%, not more than about 0.04 wt.%, not more than about 0.05 wt.%, not more than about 0.06 wt.%, not more than about 0.07 wt.%, not more than about 0.08 wt.%, not more than about 0.09 wt.%, not more than about 0.1 wt.%, not more than about 0.25 wt.%, not more than about 0.5 wt.%, not more than about 0.75 wt.%, not more than about 1 wt.%, not more than about 1.5 wt.%, not more than 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 any range including and / or in-between any two of these values.

[0075]

[0032] In any embodiment herein, the composition may include less than about 2 wt.% secondary amine (e.g., 3-(ethylamino)pentan-2-ol, 2-(butylamino)ethanol, diethanolamine, diisopropanolamine (also referred to as l-(2-hydroxypropylamino)propan-2-ol), and / or dicycohexylamine). Thus, in any embodiment herein, the composition may include an amount of secondary amine that is less than about 2 wt.%, less than about 1.5 wt.%, less than about 1 wt.%, less than about 0.5 wt.% secondary amine, or any range including and / or inbetween any two of these values. For example, in any embodiment herein, the composition may include less than about 0.5 wt.% secondary amine.

[0076]

[0033] In any embodiment herein, the composition may exhibit a biobased content of a compound of Formula I as determined using radiocarbon analysis in accordance with ASTM D6866-24 of 0% to 100%. For example, such ranges of biobased content of the compound of Formula I in compositions of the present technology may be provided by using a purely petroleum-based compound of Formula I (z.e., with 0% biobased content), using a compound of Formula I produced in part with biobased starting materials, using combinations of a purely petroleum -based compound of Formula I and a compound of Formula I produced in part or in whole with biobased starting materials, or — for a biobased content of a compound of Formula I of 100% — using a compound of Formula I produced in whole with biobased

[0077] -16-

[0078] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 starting materials. Thus, in any embodiment herein, the composition may exhibit a biobased content of a compound of Formula I (as determined using radiocarbon analysis in accordance with 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 any range including and / or in-between any two of these values. For example, the composition of any embodiment herein may exhibit a biobased content of a compound of Formula I as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 10%, or may exhibit a biobased content of a compound of Formula I as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 25%. Accordingly, a composition of any aspect and / or embodiment herein may include a renewable, biobased compound (z.e., a compound of Formula I of any embodiment disclosed herein) that exhibits low toxicity while concurrently providing comparable or superior performance as compared to petroleum based alternatives and superior performance as compared to current renewable alternatives (e.g., NEb).

[0079]

[0034] Stereoisomeric mixtures of a compound of Formula I may be separated by methods known in the art, including chiral chromatography or diastereomeric salt recrystallization. Diastereomeric salt recrystallization involves neutralizing a chiral amino alcohol using an optically active acid. The resulting diastereomers are separated by crystallization and neutralized to recover the optically enriched amino alcohol. The crystallization process may be repeated to achieve optical purity of 99% or higher. Further, for example, diastereomeric amino alcohols may be separated by distillation or crystallization.

[0080] Metalworking Fluid Compositions Including A Compound of Formula

[0081]

[0035] In an aspect, provided herein are metalworking fluids that include a compound of Formula I

[0082] -17-

[0083] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 wherein

[0084] R1, R2, R3, and R4are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4is not H; and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms; water; and optionally a base oil.

[0085]

[0036] Metalworking fluids include such compositions useful in metal removal, metal forming, metal cleaning, and / or metal treating (e.g., cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, protecting, and the like). Metalworking fluids comprising a compound of Formula I may be used in all categories of metalworking fluid processes, including but not limited to metal removal, cutting, grinding, boring, metal forming, drawing, stamping, rolling, and forging. Metalworking processes generate heat and friction, and the metalworking fluid compositions herein provide cooling by removing heat generated during operation and lubrication between the tool and the metal workpiece (e.g., a metal part). The present metalworking fluids may also remove debris without leaving a residue, and protect the tool and part being manufactured. A compound of Formula I may be used in each of the four types of metalworking fluids: neat oils, soluble oils, semi-synthetic, and synthetic metalworking fluid. In any embodiments, metalworking fluids are provided in a concentrated form and are diluted with water prior to use. The present technology encompasses metalworking fluid concentrates including a base oil and / or synthetic polymer. Metalworking fluids may further include emulsifiers, lubricants (boundary and extreme pressure lubricants), amine and / or one more amino alcohols other than a compound of Formula I, and performance additives (corrosion inhibitors, couplers, defoamers, and biocides), diluted metalworking fluids thereof, metalworking fluid concentrates pre-diluted with water, as well as neat metalworking fluids. Typically, 1 part by weight of a metalworking fluid concentrate is diluted with between about 4 and about 100

[0086] -18-

[0087] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 parts of water (i.e., diluted to about 1 vol% to about 20 vol% of its original concentration). In any embodiments, the dilution may be 10 to 50 parts of water or even 15 to 30 parts of water.

[0088]

[0037] In any aspect and / or embodiment herein of the present technology, the compound of Formula I may be one or more of

[0089] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 composition may include the one or more of such compounds in a total amount of about 30 wt.%, about 35 wt.%, about 40 wt.%, about 45 wt.%, about 50 wt.%, about 55 wt.%, about 60

[0090] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 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

[0091] 99.5 wt.%, about 99.9 wt.%, about 99.95 wt.%, about 99.99 wt.%, or any range including and / or in-between any two of these values. In any aspect or embodiment herein, it may be the compound of Formula I includes at least In any aspect or embodiment herein, the compound of Formula I may include no more than three of may include no more than two of

[0092] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0093] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0094] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 nt herein, it may be the compound of Formula I is in any aspect or embodiment herein, it may be the compound of

[0095] Formula I is

[0096] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0097]

[0039] In any aspect and / or embodiment herein, the metalworking fluid may further include an amino alcohol other than a compound of Formula I (an “other amino alcohol”), where exemplary other amino alcohols that may be included in a metalworking fluid composition of any embodiment herein include, but are not limited to, 2-aminoethanol, triethanolamine, 1- amino-2-propanol, 2-amino-2-m ethyl- 1 -propanol, 2-amino-l -butanol, 2-amino-2-ethyl-l,3- propanediol, 3-(ethylamino)pentan-2-ol, 3-amino-3-methyl-2-butanol, or a combination of any two or more thereof. The composition of any aspect and / or embodiment herein may include an other amino alcohol (e.g., 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-methyl-l -propanol, 2-amino-l -butanol, 2-amino-2-ethyl-l,3-propanediol, 3- (ethylamino)pentan-2-ol, 3 -amino-3-methyl-2 -butanol, or a combination of any two or more thereof) in an amount 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.%, 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 any range including and / or in-between any two of these values. The composition of any aspect and / or embodiment herein may include an other amino alcohol (e.g., 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-methyl-l -propanol, 2-amino-l -butanol, 2-

[0098] -25-

[0099] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 amino-2-ethyl- 1,3 -propanediol, 3-(ethylamino)pentan-2-ol, 3-amino-3-methyl-2-butanol, or a combination of any two or more thereof) in an amount of not more than about 0.01 wt.%, not more than about 0.02 wt.%, not more than about 0.03 wt.%, not more than about 0.04 wt.%, not more than about 0.05 wt.%, not more than about 0.06 wt.%, not more than about 0.07 wt.%, not more than about 0.08 wt.%, not more than about 0.09 wt.%, not more than about 0.1 wt.%, not more than about 0.25 wt.%, not more than about 0.5 wt.%, not more than about 0.75 wt.%, not more than about 1 wt.%, not more than about 1.5 wt.%, not more than 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 any range including and / or in-between any two of these values.

[0100]

[0040] In any embodiment herein, the metalworking fluid may include less than about 2 wt.% secondary amine (e.g., 3-(ethylamino)pentan-2-ol, 2-(butylamino)ethanol, diethanolamine, diisopropanolamine (also referred to as l-(2-hydroxypropylamino)propan-2- ol), and / or dicycohexylamine). Thus, in any embodiment herein, the composition may include an amount of secondary amine that is less than about 2 wt.%, less than about 1.5 wt.%, less than about 1 wt.%, less than about 0.5 wt.% secondary amine, or any range including and / or in-between any two of these values. For example, in any embodiment herein, the composition may include less than about 0.5 wt.% secondary amine.

[0101]

[0041] In any aspect and / or embodiment herein, and as discussed previously in the present disclosure, the metalworking fluid may exhibit a biobased content of a compound of Formula I as determined using radiocarbon analysis in accordance with ASTM D6866-24 of 0% to 100% — thus, in any embodiment herein, the composition may exhibit a biobased content of a compound of Formula I (as determined using radiocarbon analysis in accordance with 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 any range including and / or in-between any two of these values. For example, the composition of any embodiment herein may exhibit a biobased content of a compound of Formula I as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 10%, or may

[0102] -26-

[0103] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 exhibit a biobased content of a compound of Formula I as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 25%. Accordingly, a composition of any aspect and / or embodiment herein may include a renewable, biobased compound (z.e., a compound of Formula I) that exhibits low toxicity while concurrently providing comparable or superior performance as compared to petroleum based alternatives and superior performance as compared to current renewable alternatives (e.g., NH3, NaOH).

[0104]

[0042] In any aspect and / or embodiment herein, the metalworking fluid have a pH between about 7 and about 12, such as a pH between about 8 and about 10. Thus, in any aspect and / or embodiment herein, the metalworking fluid have 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 any range including and / or in-between any two of these values.

[0105] AMB in Metalworkins Fluids

[0106]

[0043] The concentration of compound of Formula I in a metalworking fluid concentrate (z.e., prior to dilution) may be at least about 1% by weight. In some embodiments, the concentration of compound of Formula I is about 1 wt.% to about 20 wt.%, e.g., any of about 1, 2, 3, 4, 5, 6, 7, 8, 9 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 wt.%, or a range between and including any two of the foregoing values. For example, in some embodiments, the concentration is in the range of about 2 to about 12 wt.%, or about 3 to about 8 wt.%. In the final diluted metalworking fluid, the use range of neat compound of Formula I may be between about 0.01wt.% or 0.02 wt.% to about 2%, e.g., 0.05 wt.% to 1 wt.%, or even about 0.1 wt.% to about 0.5 wt.%.

[0107] Base oils

[0108]

[0044] Metalworking fluids, including concentrates, may contain a base oil, which may be a hydrocarbon oil or a synthetic polymer or copolymer. Examples of synthetic and nonsynthetic base oils commonly used include, for instance, mineral oils, synthetic polymers / copolymers. Specific examples of such oils include, without limitation, petroleum oil, severely hydrotreated naphthenic and paraffinic oils, synthetic hydrocarbons, polyalphaolefin, polyglycol block co-polymers, and vegetable oils. Typical amounts of oils in metalworking fluid range from about 0 wt.% to about 90 wt.%, for example, any of about

[0109] -27-

[0110] 4917-5677-7320.2 Atty. Dkt. No.: I0969I-080I

[0111] 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90 wt.% or a range between and including any two of the foregoing values. In some embodiments, the amount of soluble oil in the metalworking fluid ranges from about 30 wt.% to about 90 wt.%, including any of about 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90 wt.% or a range between and including any two of the foregoing values. In some embodiments the amount of, e.g., severely refined petroleum oils in semisynthetic metalworking fluid ranges from about 5 wt.% to about 40 wt.%, including any of about 5, 10, 15, 20, 25, 30, 35, 40, 45, or 50 wt.% or a range between and including any two of the foregoing values. Synthetic metalworking fluid typically have 0% base oil as lubricity is provided by synthetic lubricants, including synthetic polymers.

[0112] Additives

[0113]

[0045] A variety of additives may be employed in metalworking fluid to modify properties of the base oil, including emulsifying agents, lubricants, carboxylic acid salts, corrosion inhibitors, metal deactivators, coupling agents, defoamers, biocides, chelating agents, antimist agents, dyes or colorants, or combinations of any two or more thereof.

[0114] Emulsifying Agents

[0115]

[0046] Metalworking fluids and concentrates (e.g., soluble oil metalworking fluids or semisynthetic metalworking fluids) may contain emulsifying agents to bridge the gap between oil and water. Notably, some emulsifying agents are also coupling agents; exemplary coupling agents are described later in this disclosure. Emulsifiers may be anionic, non-ionic, or amphoteric in nature. Suitable emulsifiers include, but are not limited to, alkanolamides, alkylaryl sulfonates, alkylaryl sulfonic acids, amine oxides, amide 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., nonyl phenol ethoxylates), fatty amines and esters, glycerol esters, glycol esters, imidazolines and imidazoline derivatives, lignin and lignin derivatives, maleic or succinic anhydrides, methyl esters, monoglycerides and derivatives, naphthenic acids, olefin sulfonates, phosphate esters, polyalkylene glycols, polyethylene glycols, polyols, polymeric (polysaccharides, acrylic acid,

[0116] -28-

[0117] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 acrylamide), propoxylated & ethoxylated fatty acids, alcohols or alkyl phenols, quaternary surfactants, sarcosine derivatives, soaps, sorbitan derivatives, sucrose and glucose esters and derivatives, sulfates and sulfonates of oils and fatty acids (e.g., sodium petroleum sulfonates), sulfates and sulfonates ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, sulfates of fatty esters, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalene and alkyl naphthalene, sulfonates of petroleum, sulfosuccinamates, sulfosuccinates and derivatives, and tridecyl and dodecyl benzene sulfonic acids. The emulsifiers may be used at 25 wt.% or less based on the total weight of the metalworking fluid, e.g., about 0.1 wt.% to about 25 wt.%. Suitable amounts thus include any 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 a range between and including any two of the forgoing values. In any embodiments, the emulsifier may be present at about 0.1 wt.% to about 20 wt.%, or about 1 wt.% to about 15 wt.%.

[0118] Lubricants (Boundary and Extreme Pressure)

[0119]

[0047] The two main types of lubrication in metalworking fluid processes are boundary and extreme pressure (EP). Boundary lubrication involves separating the moving surfaces by the additive absorbing or adsorbing to the surface to form a film of fluid lubricant to reduce friction and heat. Boundary lubricants include fats, vegetable oils, esters, fatty esters, complex esters, polyol esters, fatty acids, tall oil fatty acids (TOFA), fatty acid and amino alcohol salts (e.g., oleic acid AMB salt, other amino alcohol salt) block polymers, and polyglycols. EP lubricants chemisorb to the surface to form a chemical layer that minimizes the wear experienced when surfaces rub together. Extreme pressure lubricants include phosphate esters (e.g., zinc dialkyl dithiophosphate), chlorinated paraffins, chlorinated fatty acids, sulfurized fats, sulfurized fatty acids, sulfurized olefins, and overbased calcium sulfonates.

[0120] Polymeric lubricant additives can provide both types of lubrication and may be used in synthetic and semi -synthetic metalworking fluids. These can be comprised of one or more of the following: 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

[0121] -29-

[0122] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 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 and an acrylic ester.

[0123]

[0048] Metalworking fluids according to the present technology may include 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%. Desirably, metalworking fluids according to the present invention may include 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% based on the total weight of the metalworking fluid and up to 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% based on the total weight of the metalworking fluid. Metalworking fluids according to the present invention may include one or more extreme pressure lubricants in an amount of 0 to about 40% based on the total weight of the metalworking fluid, more preferably about 5 to about 25% or less, and most preferably about 1 to about 5%. Desirably, metalworking fluids according to the present invention may include one or more extreme pressure lubricants in an amount of at least 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10% based on the total weight of the metalworking fluid and up to 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% based on the total weight of the metalworking fluid.

[0124] Carboxylic Acid Salts with Amino Alcohols, Amides and Esters

[0125]

[0049] Partially neutralized carboxylic acids salts of a compound of Formula I (and, optionally in addition, or one or more other amino alcohols) provide a lipophilic moiety for the polymeric lubricity agents to network with and provide for the engineering of a larger droplet size. The pH of the partial neutralization is dependent upon the alkaline agent used.

[0126] -30-

[0127] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0128] Many of these carboxylic acid salts additionally provide their own boundary lubrication as well. The carboxylic acids can be linear or branched, saturated or unsaturated, fatty or oil, animal or vegetable, cis or trans configured, dicarboxylic, tricarboxylic, esterified, amines, amides, or ethoxylated. Examples of carboxylic acids that may be used include: caproic / hexanoic acid, enanthic / heptanoic acid, caprylic / octanoic acid, pelargonic / nonanoic acid, isononanoic acid, capri c / decanoic acid, neodecanoic acid, lauric / dodecanoic acid, stearic / octadecanoic acid, arachidic / eicosanoic acid, palmitic / hexadecanoic acid, erucic acid, oleic acid, arachidonic acid, linoleic acid, linolenic acid, myristic / tetradecanoic acid, behenic / docosanoic acid, alpha-linolenic acid, docosahexaenoic acid, ricinoleic acid, butyric acid, lard oil, tallow oil, butter, coconut oil, palm oil, cottonseed oil, wheat germ oil, soya oil, olive oil, corn oil, sunflower oil and rapeseed / canola oil.

[0129]

[0050] In metalworking fluids of the present technology, carboxylic acid salts of a compound of Formula I (and, optionally in addition, of one or more other amino alcohols) may be present in an amount from about 1 wt.% to about 20 wt.%, including any of about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 wt.% or a range between and including any two of the foregoing.

[0130] Performance Additives

[0131]

[0051] A variety of performance additives may be used in metalworking fluids and concentrates, including but not limited to corrosion inhibitors, metal deactivators, cobalt leaching inhibitors, coupling agents, defoamers, biocides, chelating agents, anti-mist agents, dyes or colorants, or combinations of any two or more thereof.

[0132]

[0052] Corrosion inhibitors act as rust inhibitors and metal passivators by preventing oxygen and acids from getting to the metal and corroding the surface. Examples of corrosion inhibitors include medium -high molecular weight sodium petroleum sulfonates, 1,2,4- thiadiazole, alkanolamides, and amino alcohol salts (salts of a compound of Formula I and, optionally in addition, one or more other amino alcohol salts) of various organic and inorganic acids including TOFA, mixed diacids, nonanoic, neodecanoic, sebacic, oleic, boric acids and many others known to those of skill in the art. Corrosion inhibitors may be present in metalworking fluids of the present technology in an amount ranging from about 0.05 wt.%

[0133] -31-

[0134] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 to about 10 wt.%. Suitable amounts include any of about 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 6, 7, 8, 9, or 10 wt.% or a range between and including any two of the foregoing values. In any embodiments the corrosion inhibitors may be present in an amount of about 0.1 wt.% to about 2 wt.% or even 1 wt.%.

[0135]

[0053] Metal deactivators and cobalt leaching inhibitors may be included to control copper corrosion of machinery’s electrical contacts and / or prevent corrosion of brass and bronze alloys. Cobalt leaching inhibitors protect the integrity of sintered carbide tooling. “Carbide” tooling includes tooling where powder metal iron carbide has been pressed and sintered together with a cobalt binder.

[0136]

[0054] Coupling agents are often used to improve the stability of the emulsion by being soluble in both the oil and water phase including glycols (e.g., propylene glycol and hexylene glycol) glycol ethers (e.g., propylene glycol n-butyl ether), higher alcohols (e.g., hexanol), fatty alcohol (e.g., tridecyl alcohols), and fatty acids (caprylic acid, isononanoic acid, and neodecanoic acid). . Coupling agents may be present in metalworking fluids of the present technology in an amount ranging from about 0.05 wt.% to about 10 wt.%. Suitable amounts include any of about 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 6, 7, 8, 9, or 10 wt.% or a range between and including any two of the foregoing values. In any embodiments the coupling agents are present in an amount of about 0.1 wt.% to about 2 wt.% or even 1 wt.%.

[0137]

[0055] Defoamers affect surface tension. They are dispersed and not fully soluble in the metalworking fluid concentrate or the metalworking fluid composition and lie on the surface in use. Defoamers include silicones, reacted silicones, organo modified siloxanes, polyalkylenimines, and waxes. Exemplary defoamers include polyethyleneimine, alkyl polysiloxane such as dimethyl polysiloxane, diethyl polysiloxane, dipropyl polysiloxane, methyl ethyl polysiloxane, dioctyl polysiloxane, diethyl polysiloxane, methyl propyl polysiloxane, dibutyl polysiloxane and didodecyl polysiloxane; organo-phosphorus compound such as n-tri-butyl phosphate, n-tributoxy ethyl phosphate or triphenylphosphite, or a mixture therefore; and copolymers of poly alkylene oxide (ethylene oxide, propylene oxide and butylene oxide). Defoamers may be present in metalworking fluids at about 0.01 wt.% to about 2 wt.%. Suitable amounts thus include any of about 0.01, 0.05, 0.1, 0.2, 0.3,

[0138] -32-

[0139] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0140] 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.25, 1.5, 1.75, or 2 wt.% or a range between and including any two of the foregoing values.

[0141]

[0056] Biocides are used for microbial control in metalworking fluids. Biocides that may be used in metalworking fluids — and may be used in a metalworking fluid of the present technology — for microbial control (e.g., bacteria and / or fungi) include but not limited to triazines, isothiazolones, dinitromorpholines, parachlorometacresol, phenolics, bromonitropropanes, butyl carbamates, or a combination of any two or more thereof. Exemplary active concentration ranges for the biocide in metalworking fluids and concentrates varies depending on the biocide being used, but can be readily determined by a person of ordinary skill in the art. By way of example, in any embodiment herein of the present technology including a biocide, the concentration may be at least about 0.01 wt.% and / or may be no more than about 5 wt.%. Suitable concentrations include any of about 0.01, 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, or 5 wt.% or a range between and including any two of the foregoing values. In any embodiments, the biocide may be present at about 0.01 wt.% to about 3 wt.% or about 4 wt.%.

[0142]

[0057] By way of example for specific biocides, l,3,5-tris(2-hydroxyethyl)-s-triazine is commonly used in the active range of 0.76 to 3% by weight, especially, 1.1 to 3%, iodopropynylbutylcarbamate is used in the range of 0.2 to 0.6%, e.g., 0.3 to 0.6%, 1,2- benzisothiazolinone is used in the range of 0.08 to 0.36%, e.g., 0.16 to 0.36%, 4,4- dimethyloxazolidine is used in the range of 0.78 to 3.1% e.g., at 1.2 to 3.1%, 7-ethyl bicycooxazolidine is used in the range 1 to 4%, especially 1.5 to 4%, a combination of 4-(2- nitrobutyl)-morpholine with 4,4'-(2-ethyl-2-nitrotrimethylene)dimorpholine is used in the range of 1 to 4%, e.g., at 1.5 to 3%, and a combination of 5-chloro-2-methyl-4-isothiazolin-3- one with 2-methyl-4-isothiazolin-3-one is used in the range of 0.01% to 0.08%, e.g., 0.05% to 0.08%.

[0143] Amines and Amino Alcohols Other than AMB

[0144]

[0058] Amines and amino alcohols are widely used to neutralize critical acid-functional ingredients (emulsifiers, lubricity additives corrosion inhibitors, etc.), and to develop and maintain alkaline pH >7 and to provide buffering capacity. This ensures the higher pH which

[0145] -33-

[0146] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 helps to increase bioresistance of metalworking fluid concentrates and dilutions, and to protect tools and parts from corrosion. Amino alcohol choice can significantly influence performance, including but not limited to providing pH stability, and forming amino alcohol salts improving emulsifier efficiency (anionic emulsifier salts), boundary and EP lubrication (acidic lubricant salts).

[0147]

[0059] Alkalinity, pH, and bacteria affect the corrosion characteristics of a lubricant, and therefore products are formulated to maintain these attributes accordingly. A drop in pH is a good indicator that bacteria is present and rust is likely going to occur. Corrosion control (e.g., diacid salts) of ferrous alloys, reducing corrosion and staining of aluminum alloys (e.g., acidic phosphate ester salts), improving tool life (low metal leaching, e.g., cobalt from carbide tools) and synergy with biocide providing fluid longevity (microbial resistance). Amino alcohols most often used are primary and tertiary. Ideally metalworking fluids should be secondary amine free (e.g., diethanolamine (DEA free).

[0148]

[0060] Thus, as disclosed previously herein, in any aspect and / or embodiment herein the metalworking fluid composition may further include an amino alcohol other than a compound of Formula I (an “other amino alcohol”), where exemplary other amino alcohols that may be included in a metalworking fluid composition of any embodiment herein include, but are not limited to, 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-m ethyl- 1- propanol, 2-amino-l -butanol, 2-amino-2-ethyl- 1,3 -propanediol, 3-(ethylamino)pentan-2-ol, 3-amino-3-methyl-2-butanol, or a combination of any two or more thereof. The composition of any aspect and / or embodiment herein may include an other amino alcohol e.g., 2- aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-methyl-l -propanol, 2-amino- 1-butanol, 2-amino-2-ethyl-l,3-propanediol, 3-(ethylamino)pentan-2-ol, 3-amino-3-methyl-2- butanol, or a combination of any two or more thereof) in an amount 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.%, 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

[0149] -34-

[0150] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 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 any range including and / or inbetween any two of these values. The composition of any aspect and / or embodiment herein may include an other amino alcohol (e.g., 2-aminoethanol, triethanolamine, l-amino-2- propanol, 2-amino-2-methyl-l -propanol, 2-amino-l -butanol, 2-amino-2-ethyl-l,3- propanediol, 3-(ethylamino)pentan-2-ol, 3-amino-3-methyl-2-butanol, or a combination of any two or more thereof) in an amount of not more than about 0.01 wt.%, not more than about 0.02 wt.%, not more than about 0.03 wt.%, not more than about 0.04 wt.%, not more than about 0.05 wt.%, not more than about 0.06 wt.%, not more than about 0.07 wt.%, not more than about 0.08 wt.%, not more than about 0.09 wt.%, not more than about 0.1 wt.%, not more than about 0.25 wt.%, not more than about 0.5 wt.%, not more than about 0.75 wt.%, not more than about 1 wt.%, not more than about 1.5 wt.%, not more than 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 any range including and / or in-between any two of these values.

[0151]

[0061] The examples herein are provided to illustrate advantages of the present technology and to further assist a person of ordinary skill in the art with preparing or using the compositions of the present technology. The examples herein are also presented in order to more fully illustrate the present technology. The examples should in no way be construed as limiting the scope of the present technology, as defined by the appended claims. The examples can include or incorporate any of the variations, aspects or aspects of the present technology described above. The variations, aspects or aspects described above may also further each include or incorporate the variations of any or all other variations, aspects or aspects of the present technology.

[0152] EXAMPLES

[0153]

[0062] The ILTPAC names and abbreviations of the compounds tested herein are provided below.

[0154] -35-

[0155] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0156] Example 1. Synthesis of 3-Aminopentan-2-ol (“3A2P”)

[0157]

[0063] 1 -Nitropropane (534.54 g, 6.0 mol) and acetaldehyde (264.3 g, 6.0 mol) were added to triethylamine (12.14 g, 0.12 mol) in methanol (90 g) while maintaining the temperature below 50 °C. The mixture was stirred at ambient temperature overnight. A portion of the reaction mixture was then fed into a stainless steel reactor containing Raney Nickel (10 wt.%) and methanol with 650 psi hydrogen at 50-80 °C. Upon complete reaction, the mixture was separated from the catalyst and distilled at ambient pressure. The fraction containing the desired product was collected at 168-170 °C and recovered as a colorless liquid. The isolated yield was 80% and the purity was 95% according to GC-FID analysis (capillary column: 30 m fused silica, (5%-phenyl)-methylpolysiloxane bonded-phase column with a 0.25 mm inner diameter and 1.0 pm film thickness; carrier gas flow rate: 1 mL / min helium; gas

[0158] -36-

[0159] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 chromatograph: Agilent model 7890, Series II). The symanti diastereomeric ratio was 67:33.

[0160] In the synthesis, renewable biobased 1 -nitropropane and / or bio-acetaldehyde may be utilized.

[0161] Example 2. Synthesis of 2-Amino-2-methylpentan-3-ol

[0162]

[0064] 2-amino-2-methylpentan-3-ol was prepared from 2-nitropropane and propionaldehyde according to as similar protocol as described in Example 1, except using 2-nitropropane instead of 1 -nitropropane and using propionaldehyde instead of acetaldehyde. The pure product fraction (99% purity by GC-FID) had a boiling point of 171 °C at atmospheric pressure.JH NMR (D2O) confirmed successful synthesis of 2-amino-2-methylpentan-3-ol. In the synthesis, renewable biobased 2-nitropropane and / or bio-propionaldehyde may be utilized.

[0163] Example 3. Exemplary Synthesis of Renewable Biobased 2-Nitropropane

[0164]

[0065] Titanium silicalite- 1 (5.0 g, TS-1, ACS Material), bio-based acetone (29 g, 0.5 mol, MilliporeSigma), and 10% aqueous ammonia (170.3 g, 1.0 mol) were charged into a 3-neck flask equipped with a condenser. The mixture was heated to 60 to 65 °C and then 35% aqueous hydrogen peroxide (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 addition of hydrogen peroxide, the mixture was kept at 65 °C for 2-4 hours until all intermediate oxime reacted according to GC. The reaction mixture was cooled to room temperature (24 ± 2 °C) and filtered. 2-Nitropropane was separated from the aqueous layer using a separatory funnel and then dried using anhydrous sodium sulfate. The isolated yield of 2-nitropropane was 75% with purity of 97%.

[0165] -37-

[0166] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0167] Example 4. Exemplary Semi-Synthetic Metalworking Fluid Compositions with Single Biocide Benzisothiazolinone

[0168]

[0066] Semi-synthetic metal working fluids containing benzisothiazolinone biocide and having the compositions shown in Table 1 below were prepared using about 0.9 M of neutralizer (AMP, MIPA, DGA, MEA, or 3A2P) to have a target pH of about 9.5 when diluted to a 5% use solution. Compositions A, B, C, and D are comparative compositions, whereas Composition E contains 3 A2P in accordance with the present technology. Each composition was prepared according to the following protocol:

[0169] 1. Add 1-7 (water, diacid, and one of AMP, MIPA, DGA, MEA, or 3A2P) at room temperature (24 ± 2 °C) and mix until dissolved (clear) 5-10 minutes.

[0170] 2. In a separate container heat 8 (naphthenic oil) and 9 (sodium sulfonate) up to 100 °C for 5-10 minutes to disperse sodium sulfonate into naphthenic oil. Allow to cool or ice bath to room temperature (24 ± 2 °C). Then add 10-13 to 8 and 9 (oil phase) at room temperature. Mix for 5-10 minutes until homogeneous.

[0171] 3. Add oil phase (8-13) to water phase (1-7) at room temperature (24 ± 2 °C). Mix for 5-10 minutes until homogeneous.

[0172] 4. While mixing add 14 drop-wise at room temperature (24 ± 2 °C). Mix for 30 minutes - 1 hour until a stable emulsion is formed.

[0173] 5. Wait 24 hours to pH at 5% dilution in distilled water.

[0174] -38-

[0175] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0176] Table 1. Exemplary Semi -Synthetic Metalworking Fluid Compositions A-E with

[0177] Benzisothiazolinone

[0178] -39-

[0179] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0180] Example 5. Exemplary Semi-Synthetic Metalworking Fluid Compositions with Mixed Biocides Benzisothiazolinone and Ortho-phenylphenol

[0181]

[0067] Semi -synthetic metal working fluids containing the biocides benzisothiazolinone and ortho-phenylphenol, and having the compositions shown in Table 2 below were prepared to have a target pH of about 9.5 when diluted to a 5% (by weight) use solution. Compositions F, G, and H are comparative compositions, whereas Composition I contains 3 A2P in accordance with the present technology. Each composition was prepared according to the following protocol:

[0182] 6. Add 1-7 (water, diacid, and one of AMP, MIPA, DGA, MEA, or 3A2P) at room temperature (24 ± 2 °C) and mix until dissolved (clear) 5-10 minutes.

[0183] 7. In a separate container heat 8 (naphthenic oil) and 9 (PIBSA) up to 100 °C for 5-10 minutes to disperse sodium sulfonate into naphthenic oil. Allow to cool or ice bath to room temperature (24 ± 2 °C). Then add 10-14 to 8 and 9 (oil phase) at room temperature. Mix for 5-10 minutes until homogeneous.

[0184] 8. Add oil phase (8-14) to water phase (1-7) at room temperature (24 ± 2 °C). Mix for 5-10 minutes until homogeneous.

[0185] 9. While mixing add 15 drop-wise at room temperature (24 ± 2 °C). Mix for 30 minutes to 1 hour until a stable emulsion is formed.

[0186] 10. Wait 24 hours to pH at 5% dilution in distilled water.

[0187] Table 2. Semi -Synthetic Metalworking Fluid Compositions F-I with Mixed Biocides Benzisothiazolinone and Ortho-phenylphenol

[0188] -40-

[0189] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0190] Example 6. Performance Testing of Metalworking Fluid with 3-Aminopentan-2-ol

[0191]

[0068] The aluminum-staining abilities of metalworking fluid Compositions A, B, C, D, and E of Example 4 were determined using the following procedure:

[0192] 1. Prepare 5% metalworking fluid dilutions of each fluid in 200 ppm hardness water.*

[0193] 2. Submerge freshly abraded (dry sanded) aluminum coupons in 35 mL of diluted metalworking fluid.

[0194] 3. Seal in a jar with a Teflon seal and age for 24 hours at 40 °C in oven.

[0195] -41-

[0196] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0197] 4. Rinse coupon in DI water and visually evaluate staining.

[0198] * 200 ppm hardness water is prepared by (a) adding 0.222 g CaSO4«2(H2O) and 0.085 g MgSCh in a 1 liter volumetric flask; (b) filling flask with DI water to line;

[0199] (c) mixing for 24 hours.

[0200]

[0069] Results of the aluminum staining control tests with Compositions A, B, C, D, and E are shown in FIG. 1. 3A2P showed lower staining and less corrosion than AMP, MIPA, DGA, and ME A on Aluminum 356, 2024, 6061, and 7075.

[0201]

[0070] Corrosion was tested with Compositions A, B, C, D, and E using the Cast Iron Chip Test, IP287 standard, modified as follows:

[0202] 1. Sieve the iron chips on the approximately 18-mesh screen to rej ect the fines.

[0203] 2. Use tap water ranging in hardness from 100 to 350 ppm.

[0204] 3. Prepare dilutions by weight percent to 1.0%, 1.5%, 2.0%, and 2.5% dilution levels.

[0205] 4. Place filter paper in petri dish lid and trace 3.5 cm square with a pencil using former.

[0206] 5. Weigh 2 g of IP287 iron chips into 3.5 cm square on filter paper in petri dish using former.

[0207] 6. Cover iron chips with 2 mL diluted fluid; ensure all chips are thoroughly wetted.

[0208] 7. Use petri dish bottom as a lid and cover. Allow chips with fluid to sit for approximately 2 hours; may use humidity chamber set at 25 °C and 65% relative humidity (RH).

[0209] 8. After approximately 2 hours remove filter paper from petri dish and rinse with water, allowing the chips to be removed.

[0210] 9. Place rinsed filter paper back into petri dish lid and allow to dry uncovered; dispose of used supplies; results can be seen immediately.

[0211] 10. Visual determination of corrosion.

[0212]

[0071] Results for corrosion of iron by AMP, MIPA, DGA, MEA, and 3A2P (Compositions A, B, C, D, and E of Example 4) are shown in FIG. 2. 3A2P showed comparable or better performance than AMP, MIPA, DGA, and MEA.

[0213] -42-

[0214] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0215] Example 7. Microbial Challenge Testing of Metalworking Fluid with 3-Aminopentan-2- ol

[0216]

[0072] The relative bioresistance of 3-aminopentan-2-ol in resisting against microbial proliferation was assessed. Metalworking fluids with benzisothiazolinone biocide (Compositions A, B, C, D, and E of Example 4) were used to assess 3-aminopentan-2-ol in comparison to AMP, MIPA, DGA, and MEA. Metalworking fluids with mixed biocides including benzisothiazolinone and ortho-phenylphenol (Compositions F, G, H, I) were used to assess 3-aminopentan-2-ol in comparison to MIPA, DGA, and MEA. The relative bioresistance was determined by challenging metalworking fluids with a biological inoculum and a fungal inoculum using modified ASTM E2275 protocol.

[0217]

[0073] Standard acclimated bacterial inoculum was prepared from a concentrate for each use using aseptic technique. In brief, standard acclimated bacterial inoculum was prepared by diluting 100 pL of bacterial inoculum concentrate into 250 mL of sterile tryptic soy broth (TSB) in a flask. The flask was held on a shaker at 175 rpm at room temperature (24 ± 2 °C) for about 24 hours until the solution was turbid, indicating the standard acclimated bacterial inoculum was ready for use.

[0218]

[0074] Standard fungal inoculum was prepared from a concentrate for each use using aseptic technique. In brief, standard fungal inoculum was prepared by diluting 250 pL of fungal inoculum concentrate in 250 mL of sterile deionized water. Diluted fungal inoculum was immediately ready for use or was stored on a shaker at 175 rpm at room temperature (24 ± 2 °C) until inoculation of microbial challenge samples.

[0219]

[0075] Microbial challenge testing was used to test bacterial and fungal concentrations in metalworking fluids, and to do so with microbial controls. The procedure for microbial challenge testing was as follows:

[0220] 1. Dilute metalworking fluid with tap water to 5% concentration. Mix using an orbital shaker at 175 rpm at room temperature (24 ± 2 °C) for 24 hours.

[0221] 2. After shaking for 24 hours, check and record pH, add 5 grams cast iron chips to each flask (+ / - 0.1 g), and return the flask to the orbital shaker and continue shaking at 175 rpm,

[0222] -43-

[0223] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0224] 3. After shaking for 5-7 days, streak, with lOpL inoculating loop, metalworking fluid sample from flask to tryptic soy agar (TSA) and sabouraud dextrose agar (SDA) plate. Read TSA plate after incubating at 37 °C for 48-72 hours. Read SDA plate after incubating at 29 °C for 4-7 days. After incubation, record TSA and SDA plate readings. Note: This streak (also known as the ‘clean streak’) is done to confirm there are no biological organisms or contaminants present in the fluid before inoculating with bacteria and fungi. Check pH and record as the week 1 pH reading. Inoculate diluted metalworking fluid samples with 1% bacterial culture and 1% fungal culture. Streak bacterial culture to TSA plate and fungal culture to SDA plate to confirm the cultures used to inoculate are healthy. “Healthy” inoculum is defined by the growth of Bacterial inoculum >106- seen as confluent growth on TSA plate, and Fungal inoculum >105- seen as too many to count on SDA plate. Read TSA plate (after 48- 72 hours) and SDA plate (after 4-7 days) and record as week 0 reading. Return samples to the orbital shaker at 175 rpm.

[0225] 4. One week after inoculation (and every week following, for up to 30 weeks), streak diluted metalworking fluid sample on TSA and SDA plates (then later read plates after appropriate incubation and record). Record pH of sample. Re-inoculate with 1% bacterial culture and 1% fungal culture. Return to orbital shaker at 175 rpm.

[0226] 5. Repeat step 4 each week until the diluted metalworking fluid sample has failed (bacteria CFUs > 40 and / or fungal CFUs > 10) or until the test reaches 30 weeks

[0227] 6. Add the following two microbial controls to every study. 0% Control is a standard inhouse metalworking fluid sample with no biocide added. This sample is intended to fail quickly and acts as a negative control. 1% Control is a standard in-house metalworking fluid sample made with 1% biocide added. This sample is intended to fail at a set point of time which is dictated on the biocide used. This sample should be identical in formulation to the 0% Control but has biocide added but no other differences.

[0228]

[0076] Results for microbial challenge testing of metalworking fluids with benzisothiazolinone biocide, Compositions A, B, C, D, and E of Example 4 with AMP, MIPA, DGA, MEA, and 3-aminopentan-2-ol, respectively, are shown in Table 3 and FIG. 3, where “TNTC” indicates too numerous to count, “Bacf ’ indicates bacterial measurements,

[0229] -44-

[0230] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 and “Fung” indicates fungal measurements. Results indicated 3-aminopentan-2-ol had comparable or greater bioresistance than AMP and MIPA, and greater bioresistance than DGA and MEA.

[0231] Table 3. Microbial Challenge Testing Metalworking Fluids with Benzisothiazolinone

[0232] Biocide (Compositions A, B, C, D, and E corresponding with AMP, MIPA, DGA, MEA, and 3-aminopentan-2-ol, respectively)

[0233] * TNTC = Too Numerous To Count

[0234]

[0077] Results for microbial challenge testing of metalworking fluids with mixed biocides including benzisothiazolinone and ortho-phenylphenol Compositions F, G, H, I of Example 5 with MIPA, DGA, MEA, and 3-aminopentan-2-ol, respectively, are shown in Table 4 and FIG. 4. Results indicated 3-aminopentan-2-ol had greater bioresistance than MIPA, DGA, and MEA.

[0235] Table 4. Microbial Challenge Testing Metalworking Fluids with Mixed Biocide (Compositions F, G, H, and I corresponding with MIPA, DGA, MEA, and 3 -aminopentan-2 - ol, respectively)

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[0237] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0238] Example 8. Evaluation of the Synergistic Effect of 3-Aminopentan-2-ol on the Mitigation of Existing Biofilm

[0239]

[0078] The resistance to further biofilm formation and antimicrobial efficacy of metalworking fluid Compositions A, B, C, and E of Example 4, with AMP, MIPA, DGA, and 3 A2P, respectively, were determined using a two-part procedure.

[0240]

[0079] Procedure part one included preparation of mixed-species biofilms using a CDC biofilm reactor with 347 stainless steel coupons according to modified U.S. Environmental Protection Agency SOP No. MB-19-05. The biofilm was grown under controlled batch and continuous-flow conditions for subsequent testing or analysis using the following procedure:

[0241] 1. After sterilization of the CDC biofilm reactor with stainless steel coupons secured therein, operate the reactor under batch phase conditions. Aseptically add 400 mL of 1 g / L TSB into the reactor. Inoculate the reactor with the in-house mixed culture (e.g., add 1 mL of inoculum (30 g / L in TSB incubated at 36 ± 2 °C overnight until dense culture achieved)). After 30 minutes place reactor on magnetic stir plate and set to 120 rpm. Operate the system under batch conditions (no flow) for 24 ± 2 hours at room temperature (24 ± 2 °C).

[0242] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0243] 2. Operate the reactor under continuous phase conditions. Prepare 20 L of 0.75 g / L TSB in a sterile carboy. Aseptically connect the reactor to the sterile medium reservoir using sterile tubing and clamps. Connect effluent spout tubing to a sterile waste carboy. Start the peristaltic pump and adjust flow rate to achieve a 30 ± 2 minute or 1.5 hour ± 2 minute residence time (based on reactor operating volume) setting 14 on current model. Operate the reactor in continuous phase mode for 24 + 2 hours at room temperature with stirring at 120 rpm.

[0244] 3. Turn off pump and stir plate, and aseptically remove coupons from the reactor and process coupons within 30 minutes of removal from downstream testing or storage.

[0245]

[0080] Procedure part two was used to quantify viable bacteria recovered from biofilm- grown coupons from part one and from the surrounding metalworking fluid following exposure, using vortex / sonication elution and enumeration on 3M Petrifilm according to the following procedure:

[0246] 1. Expose coupons to respective metalworking fluid. Immerse biofilm coupons in 10 mL of the test metalworking fluid from part one of the procedure for 30 minutes at room temperature without agitation.

[0247] 2. Transfer the coupon to 20 mL sterile phosphate-buffered saline PBS with Tween 80 at 0.1% (v / v) (PBS + T).

[0248] 3. Process residual metalworking fluid (liquid phase enumeration). Vortex the metalworking fluid briefly to homogenize. Prepare 10-fold serial dilutions of the metalworking fluid to 10'7using sterile PBS+T. Plate appropriate dilutions (10‘4to 1 O'7) onto 3M Petrifilm, and incubate for 24 hours.

[0249] 4. Process coupon biofilm. Vortex the PBS+T with the coupon for 30 seconds four times with 30 seconds of sonication between each vortex to release bacteria from the coupon. Serial dilute eluate (coupon-associated bacteria) with 10-fold serial dilutions through 10'7using sterile PBS+T. Plate samples onto 3M Petrifilm Aerobic Count (AC) plates, and incubate for 24 hours.

[0250] 5. Enumerate colonies using a 3M Petrifilm plate reader.

[0251]

[0081] Results for quantification of bacterial growth in the metalworking fluid and coupon eluate following biofilm growth in the reactor are shown in FIGS. 5A-5F. FIGS. 5A-5C

[0252] -47-

[0253] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 show bacterial quantification for a 30 minute residence time and FIGS. 5D-5F show bacterial quantification for 1.5 hours residence time in the continuous phase of biofilm growth in the reactor. FIGS. 5 A and 5B show bacterial quantification from the metalworking fluid following biofilm formation, FIGS. 5C and 5D show bacterial quantification from coupon biofilm eluate, and FIGS. 5D and 5E show total average bacterial quantification from both metalworking fluid and coupon eluate. Results indicated improved resistance to further biofilm formation and antimicrobial efficacy for 3A2P following 1.5 hour residence time as compared to AMP, MIPA, and DGA.

[0254] EQUIVALENTS

[0255]

[0082] While certain embodiments have been illustrated and described, a person with ordinary skill in the art, after reading the foregoing specification, can effect changes, substitutions of equivalents and other types of alterations to the compositions of the present technology as set forth herein. Each aspect and embodiment described above can also have included or incorporated therewith such variations or aspects as disclosed regarding any or all of the other aspects and embodiments.

[0256]

[0083] The present technology is also not to be limited in terms of the particular aspects described herein, which are intended as single illustrations of individual aspects of the present technology. Many modifications and variations of this present technology can be made without departing from its spirit and scope, as will be apparent to those skilled in the art. Functionally equivalent methods within the scope of the present technology, in addition to those enumerated herein, will be apparent to those skilled in the art from the foregoing descriptions. Such modifications and variations are intended to fall within the scope of the appended claims. It is to be understood that this present technology is not limited to particular methods, reagents, compounds, or compositions, which can, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only, and is not intended to be limiting. Thus, it is intended that the specification be considered as exemplary only with the breadth, scope and spirit of the present technology indicated only by the appended claims, definitions therein and any equivalents thereof.

[0257] -48-

[0258] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0259]

[0084] The embodiments, illustratively described herein may suitably be practiced in the absence of any element or elements, limitation or limitations, not specifically disclosed herein. Thus, for example, the terms “comprising,” “including,” “containing,” etc. shall be read expansively and without limitation. Additionally, the terms and expressions employed herein have been used as terms of description and not of limitation, and there is no intention in the use of such terms and expressions of excluding any equivalents of the features shown and described or portions thereof, but it is recognized that various modifications are possible within the scope of the claimed technology. Additionally, the phrase “consisting essentially of’ will be understood to include those elements specifically recited and those additional elements that do not materially affect the basic and novel characteristics of the claimed technology. The phrase “consisting of’ excludes any element not specified.

[0260]

[0085] In addition, where features or aspects of the disclosure are described in terms of Markush groups, those skilled in the art will recognize that the disclosure is also thereby described in terms of any individual member or subgroup of members of the Markush group. Each of the narrower species and subgeneric groupings falling within the generic disclosure also form part of the technology. This includes the generic description of the technology with a proviso or negative limitation removing any subject matter from the genus, regardless of whether or not the excised material is specifically recited herein.

[0261]

[0086] As will be understood by one skilled in the art, for any and all purposes, particularly in terms of providing a written description, all ranges disclosed herein also encompass any and all possible subranges and combinations of subranges thereof. Any listed range can be easily recognized as sufficiently describing and enabling the same range being broken down into at least equal halves, thirds, quarters, fifths, tenths, etc. As a non-limiting example, each range discussed herein can be readily broken down into a lower third, middle third and upper third, etc. As will also be understood by one skilled in the art all language such as “up to,” “at least,” “greater than,” “less than,” and the like, include the number recited and refer to ranges which can be subsequently broken down into subranges as discussed above. Finally, as will be understood by one skilled in the art, a range includes each individual member.

[0262]

[0087] All publications, patent applications, issued patents, and other documents (for examplejournals, articles and / or textbooks) referred to in this specification are herein

[0263] -49-

[0264] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 incorporated by reference as if each individual publication, patent application, issued patent, or other document was specifically and individually indicated to be incorporated by reference in its entirety. Definitions that are contained in text incorporated by reference are excluded to the extent that they contradict definitions in this disclosure.

[0265]

[0088] The present technology may include, but is not limited to, the features and combinations of features recited in the following lettered paragraphs, it being understood that the following paragraphs should not be interpreted as limiting the scope of the claims as appended hereto or mandating that all such features must necessarily be included in such claims:

[0266] A. A metalworking fluid comprising a compound of Formula I about 0.1 wt.% or greater water; and optionally a base oil, wherein

[0267] R1, R2, R3, and R4are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4is not H; and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms.

[0268] B. The metalworking fluid of Paragraph A, wherein the metalworking fluid comprises about

[0269] 0.01 wt.% to about 20 wt.% compound of Formula I, optionally wherein the metalworking fluid comprises about 10 wt.% to about 50 wt.% base oil.

[0270] C. The metalworking fluid of Paragraph A or Paragraph B, wherein the metalworking fluid comprises about 0.01 wt.% to about 10 wt.% compound of Formula I.

[0271] D. The metalworking fluid of any one of Paragraphs A-C, wherein the metalworking fluid is a soluble oil, a semi-synthetic, or a synthetic.

[0272] -50-

[0273] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0274] E. The metalworking fluid of any one of Paragraphs A-D, wherein the base oil comprises a petroleum oil, a hydrotreated naphthenic oil, a hydrotreated paraffinic oils, a synthetic hydrocarbon, a polyalphaolefin, a polyglycol block co-polymer, a vegetable oil, a hydrotreated vegetable oil, a complex ester, a polyol ester, a re-refined base oil, or a combination of any two or more thereof.

[0275] F. The metalworking fluid of any one of Paragraphs A-E, wherein the metalworking fluid further comprises an emulsifier, a corrosion inhibitor, a biocide, a neutralizing agent, or a combination of any two or more thereof.

[0276] G. The metalworking fluid of Paragraph F, wherein the metalworking fluid comprises a nonionic emulsifier.

[0277] H. The metalworking fluid of Paragraph G, wherein the nonionic emulsifier comprises an ethoxylated alcohol, an alkanolamide, an ester, or a combination of any two or more thereof.

[0278] I. The metalworking fluid of any one of Paragraphs F-H, wherein the metalworking fluid comprises an anionic emulsifier.

[0279] J. The metalworking fluid of Paragraph I, wherein the anionic emulsifier comprises a sodium sulfonate, fatty acid salt, a succinic acid salt, a succinic anhydride salt, a polymeric emulsifier, or a combination of any two or more thereof.

[0280] K. The metalworking fluid of Paragraph J, wherein the polymeric emulsifier comprises a polyethylene glycol.

[0281] L. The metalworking fluid of any one of Paragraphs F-K, wherein the metalworking fluid comprises the corrosion inhibitor, the corrosion inhibitor comprising one or more of a phosphate ester, a sodium sulfonate, a thiadiazole, an alkanolamide, an amino alcohol other than the compound of Formula I (an “other amino alcohol”), a salt of a compound of Formula I, an other amino alcohol salt, a tall oil fatty acid (TOFA), a diacid, or a combination of any two or more thereof.

[0282] -51-

[0283] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0284] M. The metalworking fluid of any one of Paragraphs F-L, wherein the metalworking fluid comprises the biocide, the biocide comprising a mixture of biocidal compounds, said mixture exhibiting an antibacterial and an antifungal effect and / or said mixture exhibiting a resistance to further biofilm formation including inhibition of further growth.

[0285] N. The metalworking fluid of any one of Paragraphs A-M, wherein the metalworking fluid is a concentrate to be diluted to about 1 vol% to about 20 vol% of its original concentration with water.

[0286] O. The metalworking fluid of any one of Paragraphs A-N, further comprising one or more additives selected from the group consisting of colorants; viscosity-altering agents; lubricants, buffers, anti-oxidants, coupling agents, defoamers, anti-misting agents, or a combination of any two or more thereof.

[0287] P. The metalworking fluid of any one of Paragraphs A-O, further comprising a neutralizing agent.

[0288] Q. The metalworking fluid of Paragraph P, wherein the neutralizing agent comprises one or more of a metal hydroxide, an alkyl amine, or an other amino alcohol.

[0289] R. The metalworking fluid of Paragraph P or Paragraph Q, wherein the neutralizing agent comprises one or more of monoisopropanolamine (MIPA), diglycolamine (DGA), MEA (monoethanolamine), TEA (triethanolamine), 2-amino-2-methyl-l -propanol (AMP), 2-amino-l -butanol (2AB), 2-amino-2-ethyl- 1,3 -propanediol (AEPD), methyldiethanolamine (MDEA), tri s(hydroxymethyl)aminom ethane (TRIS), dicyclohexylamine (DCHA), 3-amino-4-octanol (3A4O), or a combination of any two or more thereof.

[0290] S. The metalworking fluid of any one of Paragraphs L-R, wherein the other amino alcohol comprises one or more of 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2- amino-2-methyl-l -propanol, 2-amino-l -butanol, 2-amino-2-ethyl- 1,3 -propanediol, 3- (ethylamino)pentan-2-ol, or a combination of any two or more thereof.

[0291] -52-

[0292] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0293] T. The metalworking fluid of any one of Paragraphs L-S, wherein the metalworking fluid comprises at least about 0.01 wt.% of the other amino alcohol.

[0294] U. The metalworking fluid of any one of Paragraphs A-T, wherein the metalworking fluid comprises less than 2 wt.% secondary amine.

[0295] V. The metalworking fluid of any one of Paragraphs A-U, wherein the compound of

[0296] Formula I has a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.

[0297] W. The metalworking fluid of any one of Paragraphs A-V, wherein the metalworking fluid has a pH between about 7 and about 12, optionally wherein the metalworking fluid has a pH between about 8 and about 10.

[0298] X. The metalworking fluid of any one of Paragraphs A-W, wherein the metalworking fluid inhibits staining of nonferrous metal workpiece which the fluid contacts during metalworking operation.

[0299] Y. The metalworking fluid of any one of Paragraphs A-X, wherein the metalworking fluid inhibits cobalt leaching of cobalt containing metal workpiece and / or carbide toll which the fluid contacts during metalworking operation.

[0300] Z. The metalworking fluid of any one of Paragraphs A-Y, wherein the metalworking fluid inhibits cools and / or lubricates during metalworking operations.

[0301] AA. The metalworking fluid of any one of Paragraphs A-Z, wherein the compound of

[0302] Formula I is 3-aminopentan-2-ol.

[0303] AB. A method comprising adding to a composition an effective amount of a compound of

[0304] Formula I

[0305] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 to raise the pH of the composition, stabilize the composition, and / or at least partially neutralize an acidic compound in the composition, the composition comprising an aqueous dispersion comprising a base oil and / or an emulsifier; and wherein

[0306] R1, R2, R3, and R4are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4is not H; and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms.

[0307] AC. A composition for use in metalworking fluids and metalworking applications, the composition comprising about 30 wt.% to about 99.99 wt.% compound of Formula I wherein

[0308] R1, R2, R3, and R4are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4is not H; and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms; and about 0.01 wt.% to about 70 wt.% water.

[0309] AD. The composition for use of Paragraph AC, wherein the composition further comprises an amino alcohol other than the compound of Formula I (an “other amino alcohol”).

[0310] AE. The composition for use of Paragraph AC or Paragraph AD, wherein the composition is for use in metal removal, metal forming, metal cleaning, and / or metal treating, optionally wherein the composition is for use in cutting, grinding, boring, turning,

[0311] -54-

[0312] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801 milling, machining, drawing, stamping, forming, rolling, cleaning, and / or protecting (i) one or more metals, and / or (ii) one or more metal alloys.

[0313] AF. The composition for use of Paragraph AD or Paragraph AE, the composition comprising about 0.01 wt.% to about 60 wt.% of the other amino alcohol.

[0314] AG. The composition for use of any one of Paragraphs AD-AF, comprising not more than 1 wt.% of the other amino alcohol.

[0315] AH. The composition for use of any one of Paragraphs AC-AG, comprising about 70 wt.% to about 95 wt.% compound of Formula I and about 5 wt.% to about 30 wt.% water.

[0316] Al. The composition for use of any one of Paragraphs AD-AH, comprising about 90 wt.% compound of Formula I, about 10 wt.% water, and less than 1 wt.% of the other amino alcohol.

[0317] AJ. The composition for use of any one of Paragraphs AC- Al, wherein the composition comprises less than 2 wt.% secondary amine.

[0318] AK. The composition for use of any one of Paragraphs AD-AJ, wherein the composition further comprises not more than 5 wt.% of the other amino alcohol.

[0319] AL. The composition for use of any one of Paragraphs AD-AK, wherein the other amino alcohol is 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-methyl- 1-propanol, 2-amino-l -butanol, 2-amino-2-ethyl-l,3-propanediol, 3- (ethylamino)pentan-2-ol, or a combination of any two or more thereof.

[0320] AM. The composition for use of any one of Paragraphs AD-AL, wherein the composition comprises at least about 0.01 wt.% of the other amino alcohol.

[0321] AN. The composition for use of any one of Paragraphs AD-AM, wherein the composition comprises 3-(ethylamino)pentan-2-ol in addition to the compound of Formula I.

[0322] AO. The composition for use of any one of Paragraphs AC-AN, wherein the composition exhibits a biobased content of the compound of Formula I of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.

[0323] -55-

[0324] 4917-5677-7320.2 Atty. Dkt. No.: 109691-0801

[0325] AP. The composition for use of any one of Paragraphs AC-AN, wherein the compound of Formula I is 3-aminopentan-2-ol, and the composition exhibits a biobased content of 3-aminopentan-2-ol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.

[0326]

[0089] Other embodiments are set forth in the following claims, along with the full scope of equivalents to which such claims are entitled.

[0327] 4917-5677-7320.2

Claims

1. Atty. Dkt. No.: 109691-0801WHAT IS CLAIMED IS:

1. A metalworking fluid comprising a compound of Formula IwhereinR1, R2, R3, and R4are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4is not H; and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms; and about 0.1 wt.% or greater water.

2. The metalworking fluid of Claim 1, wherein the compound of Formula I is 3- aminopentan-2-ol .

3. The metalworking fluid of Claim 1, wherein the metalworking fluid further comprises a base oil.

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

5. The metalworking fluid of Claim 1, wherein the metalworking fluid comprises about 0.01 wt.% to about 20 wt.% compound of Formula I.

6. The metalworking fluid of Claim 1, wherein the metalworking fluid comprises about 0.01 wt.% to about 10 wt.% compound of Formula I.

7. The metalworking fluid of Claim 1, wherein the metalworking fluid is a soluble oil, a semi-synthetic, or a synthetic.-57-4917-5677-7320.2Atty. Dkt. No.: 109691-08018. The metalworking fluid of Claim 1, wherein the base oil comprises a petroleum oil, a hydrotreated naphthenic oil, a hydrotreated paraffinic oils, a synthetic hydrocarbon, a polyalphaolefin, a polyglycol block co-polymer, a vegetable oil, a hydrotreated vegetable oil, a complex ester, a polyol ester, a re-refined base oil, or a combination of any two or more thereof.

9. The metalworking fluid of Claim 1, wherein the metalworking fluid further comprises an emulsifier, a corrosion inhibitor, a biocide, a neutralizing agent, or a combination of any two or more thereof.

10. The metalworking fluid of Claim 9, wherein the metalworking fluid comprises a nonionic emulsifier.

11. The metalworking fluid of Claim 10, wherein the nonionic emulsifier comprises an ethoxylated alcohol, an alkanolamide, an ester, or a combination of any two or more thereof.

12. The metalworking fluid of any Claim 9, wherein the metalworking fluid comprises an anionic emulsifier.

13. The metalworking fluid of Claim 12, wherein the anionic emulsifier comprises a sodium sulfonate, fatty acid salt, a succinic acid salt, a succinic anhydride salt, a polymeric emulsifier, or a combination of any two or more thereof.

14. The metalworking fluid of Claim 13, wherein the polymeric emulsifier comprises a polyethylene glycol.

15. The metalworking fluid of Claim 9, wherein the metalworking fluid comprises the corrosion inhibitor, the corrosion inhibitor comprising one or more of a phosphate ester, a sodium sulfonate, a thiadiazole, an alkanolamide, an amino alcohol other than a compound of Formula I (an “other amino alcohol”), a salt of a compound of Formula I, an other amino alcohol salt, a tall oil fatty acid (TOFA), a diacid, or a combination of any two or more thereof.-58-4917-5677-7320.2Atty. Dkt. No.: 109691-080116. The metalworking fluid of Claim 9, wherein the metalworking fluid comprises the biocide, the biocide comprising a mixture of biocidal compounds, said mixture exhibiting an antibacterial and an antifungal effect.

17. The metalworking fluid of Claim 9, wherein the metalworking fluid comprises the biocide, the biocide comprising a mixture of biocidal compounds, said mixture exhibiting a resistance to further biofilm formation including inhibition of further growth.

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

19. The metalworking fluid of Claim 1, further comprising one or more additives selected from the group consisting of colorants; viscosity-altering agents; lubricants, buffers, anti-oxidants, coupling agents, defoamers, anti-misting agents, or a combination of any two or more thereof.

20. The metalworking fluid of Claim 1, further comprising a neutralizing agent.

21. The metalworking fluid of Claim 20, wherein the neutralizing agent comprises one or more of a metal hydroxide, an alkyl amine, or an other amino alcohol.

22. The metalworking fluid of Claim 20, wherein the neutralizing agent comprises one or more of monoisopropanolamine (MIPA), diglycolamine (DGA), MEA (monoethanolamine), TEA (triethanolamine), 2-amino-2-m ethyl- 1 -propanol (AMP), 2-amino-l -butanol (2AB), 2-amino-2-ethyl- 1,3 -propanediol (AEPD), methyldiethanolamine (MDEA), tri s(hydroxymethyl)aminom ethane (TRIS), dicyclohexylamine (DCHA), 3-amino-4-octanol (3A4O), or a combination of any two or more thereof.

23. The metalworking fluid of Claim 15, wherein the other amino alcohol comprises one or more of 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-methyl-l- propanol, 2-amino-l -butanol, 2-amino-2-ethyl- 1,3 -propanediol, 3- (ethylamino)pentan-2-ol, or a combination of any two or more thereof.-59-4917-5677-7320.2Atty. Dkt. No.: 109691-080124. The metalworking fluid of Claim 15, wherein the metalworking fluid comprises at least about 0.01 wt.% of the other amino alcohol.

25. The metalworking fluid of Claim 1, wherein the metalworking fluid comprises less than2 wt.% secondary amine.

26. The metalworking fluid of Claim 1, wherein the compound of Formula I has a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.

27. The metalworking fluid of Claim 1, wherein the metalworking fluid has a pH between about 7 and about 12.

28. The metalworking fluid of Claim 1, wherein the metalworking fluid inhibits staining of nonferrous metal workpiece which the fluid contacts during metalworking operation.

29. The metalworking fluid of Claim 1, wherein the metalworking fluid inhibits cobalt leaching of cobalt containing metal workpiece and / or carbide toll which the fluid contacts during metalworking operation.

30. The metalworking fluid of Claim 1, wherein the metalworking fluid inhibits cools and / or lubricates during metalworking operations.

31. A method comprising adding to a composition an effective amount of a compound ofFormula Ito raise the pH of the composition, stabilize the composition, and / or at least partially neutralize an acidic compound in the composition, the composition comprising an aqueous dispersion comprising a base oil and / or an emulsifier; and wherein-60-4917-5677-7320.2Atty. Dkt. No.: 109691-0801R1, R2, R3, and R4are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4is not H; and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms.

32. A composition for use in metalworking fluids and metalworking applications, the composition comprising about 30 wt.% to about 99.99 wt.% compound of Formula IwhereinR1, R2, R3, and R4are each independently H or Ci-Ce unsubstituted alkyl; provided at least one of R1, R2, R3, and R4is not H; and provided that the compound has 4, 5, 6, 7, 8, 9, or 10 carbon atoms; and about 0.01 wt.% to about 70 wt.% water.

33. The composition for use of Claim 32, wherein the composition is for use in cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, and / or protecting a metal and / or a metal alloy.

34. The composition for use of Claim 32, wherein the composition further comprises an amino alcohol other than the compound of Formula I (an “other amino alcohol”).

35. The composition for use of Claim 34, the composition comprising about 0.01 wt.% to about 60 wt.% of the other amino alcohol.

36. The composition for use of Claim 34, comprising not more than 1 wt.% of the other amino alcohol.-61-4917-5677-7320.2Atty. Dkt. No.: 109691-080137. The composition for use of Claim 32, comprising about 70 wt.% to about 95 wt.% compound of Formula I and about 5 wt.% to about 30 wt.% water.

38. The composition for use of Claim 32, comprising about 90 wt.% compound of Formula I, about 10 wt.% water, and less than 1 wt.% of the other amino alcohol.

39. The composition for use of Claim 32, wherein the composition comprises less than 2 wt.% secondary amine.

40. The composition for use of Claim 34, wherein the composition further comprises not more than 5 wt.% of the other amino alcohol.

41. The composition for use of Claim 34, wherein the other amino alcohol is 2- aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-methyl-l -propanol, 2- amino-1 -butanol, 2-amino-2-ethyl-l,3-propanediol, 3-(ethylamino)pentan-2-ol, or a combination of any two or more thereof.

42. The composition for use of Claim 41 wherein the composition comprises at least about0.01 wt.% of the other amino alcohol.

43. The composition for use of Claim 41, wherein the composition comprises 3-(ethylamino)pentan-2-ol in addition to the compound of Formula I.

44. The composition for use of Claim 32, wherein the composition exhibits a biobased content of the compound of Formula I of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.

45. The composition for use of Claim 32, wherein the compound of Formula I is 3- aminopentan-2-ol, and the composition exhibits a biobased content of 3-aminopentan- 2-ol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.4917-5677-7320.2

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