Formulations comprising 3-amino-2-butanol and use thereof in electrical and electronic applications
3-amino-2-butanol formulations address the need for renewable materials in electronics by offering sustainable, low-toxicity solutions with superior performance in conductive films and lithium-ion batteries.
Patent Information
- Application Number
- PCT/US2025/020122
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-04-12
- Filing Date
- 2025-03-15
- Publication Date
- 2025-10-16
AI Technical Summary
Existing electrical and electronic products rely heavily on non-renewable petroleum-based materials, leading to environmental degradation, health risks, and performance issues, necessitating the development of renewable alternatives with comparable or superior performance.
Formulations comprising 3-amino-2-butanol, a biobased compound, are used in electrical and electronic applications, providing improved sustainability, reduced toxicity, and enhanced performance in conductive films, semiconductor materials, and lithium-ion batteries.
3-amino-2-butanol formulations offer high-performance, cost-effective solutions with reduced environmental impact, comparable to or exceeding petroleum-based alternatives, while incorporating bio-based carbon.
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Figure US2025020122_16102025_PF_FP_ABST
Abstract
Description
[0001] FORMULATIONS COMPRISING 3-AMINO-2-BUTANOL AND USE THEREOF IN ELECTRICAL AND ELECTRONIC APPLICATIONS
[0002] CROSS-REFERENCE TO RELATED APPLICATIONS
[0003] [1] This application claims the benefit of and priority to U.S. Provisional Appl. No. 63 / 633,640, filed April 12, 2024, which is incorporated herein by reference in its entirety for any and all purposes.
[0004] TECHNICAL FIELD
[0005] [2] The present technology relates generally to compositions (also referred to herein as “formulations”) useful in electrical and electronic applications, where such compositions include 3-amino-2-butanol.
[0006] BACKGROUND
[0007] [3] Many commonly used products including electrical and electronic chemicals, among others, are made of compositions using chemicals typically derived from non-renewable raw materials such as petroleum.
[0008] [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. Moreover, these fossil fuels are often supplied from politically unstable parts of the world, often raising humanitarian concerns.
[0009] [5] Thus, as explained above and in more details below, there remains a need for compositions for commonly used products such as those used in the manufacture of electronic materials, electrical devices, lithium-ion batteries, and semiconductor devices made with natural, renewable starting materials that offer equivalent or better performance to current products. SUMMARY
[0010] [6] The present disclosure is directed to compositions and formulations comprising 3- amino-2-butanol (“3-AB”, also known as 3-amino-butan-2-ol; CAS No.: 42551-55-3) for electronic materials and electrical devices. 3 -Amino-2 -butanol has several advantages, including its improved sustainability profile, demonstrated by its ability to be manufactured as a renewable, biobased compound (z.e., without relying on non-renewable petroleum -based raw materials) alongside its 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., NEb). Thus, the presently disclosed technology overcomes common adoption barriers associated with renewable electronic chemicals, such as poor performance and high cost, instead providing a high-performance, cost-effective solution with the potential for incorporating bio-based carbon.
[0011] BRIEF DESCRIPTION OF THE DRAWINGS
[0012] [7] FIG. 1 provides a graph of the results of dynamic contact angle measurements of TEOS wafers treated with different semiconductor cleaning solutions (2-amino-2-methyl-l- propanol (“AMP”); SC-1 (SC-1 is a mixture of ammonium hydroxide, hydrogen peroxide, and deionized water having a pH of 9.5; a standard cleaning solution in the semiconductor industry; or amino-2-butanol (“3-AB”, of the present technology). Cleaning solutions had a pH of 9.5. The results shown in FIG. 1 indicated that wafers cleaned with 3AB had a contact angle lower than that treated with AMP or SC-1.
[0013] [8] FIGS. 2A-2C provide particle removal efficiency (“PRE (%)”) of TEOS wafers treated with different semiconductor cleaning solutions using contact and non-contact cleaning conditions. FIG. 2A is a graph of contact cleaning with different semiconductor cleaning solutions (deionized water (“DI”), SC-1, triethanolamine (“TEA”),
[0014] Tri s(hydroxymethyl)aminom ethane (“TA”), 2-amino-2-methyl-l -propanol (“AMP”), or amino-2-butanol (“3-AB”, of the present technology). FIG. 2B is a graph of non-contact cleaning with different semiconductor cleaning solutions (3-amino-4-octanol (“Corrguard EXT”), 2-amino-2-methyl-l -propanol (“AMP”), or amino-2-butanol (“3-AB”, of the present technology). FIG. 2C is a graph of contact cleaning with different semiconductor cleaning solutions (3-amino-4-octanol (“Corrguard EXT”), 2-amino-2-methyl-l -propanol (“AMP”), or amino-2-butanol (“3-AB”, of the present technology). The results shown in FIGS. 2A-2C indicated that wafers cleaned with 3 AB demonstrated comparable or better cleaning than AMP based on percent particle removal efficiency (PRE).
[0015] [9] FIGS. 3 A-3B provide contact angle of aluminum surfaces treated with different semiconductor cleaning solutions at different concentrations. FIG. 3 A is a graph of initial contact angle of aluminum surfaces treated with different semiconductor cleaning solutions (2-amino-2-methyl-l -propanol (“AMP”) or amino-2 -butanol (“3-AB”, of the present technology). FIG. 3B is a graph of dynamic contact angle of aluminum surfaces treated with different semiconductor cleaning solutions (2-amino-2-m ethyl- 1 -propanol (“AMP”) or amino-2-butanol (“3-AB”, of the present technology). The results shown in FIGS. 3A-3B indicated that aluminum cleaned with 3AB demonstrated comparable or better cleaning than AMP based on initial and dynamic contact angle analysis.
[0016]
[0010] FIGS. 4A-4B provide critical micelle concentration with different additives (2-amino- 2-methyl-l -propanol (“AMP”) or amino-2 -butanol (“3-AB”, of the present technology) and different concentrations, measured using light scattering intensity measured in kilocounts per second (“kcps”). FIG. 4A is a graph of critical micelle concentration for 3AB. FIG. 4B is a graph of critical micelle concentration for AMP. The results indicate 3AB provides similar critical micelle concentration as AMP.
[0017] DETAILED DESCRIPTION
[0018]
[0011] The following terms are used throughout as defined below.
[0019]
[0012] 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.
[0020]
[0013] 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% .”
[0021]
[0014] 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.”
[0022]
[0015] 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 ( / . e. , 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. 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.
[0023]
[0016] 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, iso- butoxy, sec-butoxy, tert-butoxy, n-pentoxy, neopentyloxy, iso-pentyloxy, n-hexyloxy or isohexyloxy), and in any embodiments, may have 1 to 4 carbon atoms. In any embodiments, the alkoxy groups may include methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy and tert-butoxy. In some embodiments, the alkoxy group is unsubstituted.
[0024]
[0017] 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.
[0025]
[0018] 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.
[0026]
[0019] 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).
[0027]
[0020] As used herein, “binder” refers to the film forming component of a coating. To form the films, the polymeric binder (z.e., polymer) may be coalesced. Coalescence refers to the process where first the solvent (e.g., water) evaporates causing the polymeric binders to be drawn together and then fused into irreversibly bound networked structures, so that the coating cannot redissolve in the original carrier solvent. Polymeric binder resin is also referred to as “binder” and “polymeric binder.”
[0021] As used herein, “water-reducible polymeric binder” (z.e., water-reducible binder) refers to a hydrophobic resin that has been modified to contain acidic groups such that the binder is soluble in water with at least partial neutralization. As used herein, “water- dispersible polymeric binder” (z.e., water-dispersible binder) refers to resins with acidic groups that could be dispersed in a continuous aqueous medium with at least partial neutralization.
[0028]
[0022] 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 free of detectable amounts of the component.
[0029] 3-Amino-2-butanol (“3-AB”) Compositions
[0030]
[0023] In an aspect, the present technology provides a composition for use in electrical and electronic applications, such as for use in conductive films (including for transparent conductors and sensors, semiconductor films for sensors, and photovoltaics), for use in lithium-ion batteries (LIBs), for use in battery manufacturing, and / or for use in semiconductor materials and devices (such as in the manufacture of semiconductor materials and devices as a cleaning formulation and / or in preparing semiconductor devices such as diodes, transistors, integrated circuits, photonic devices, memory devices, and / or sensors), where the composition includes about 30 wt% to about 99.99 wt% 3-amino-2-butanol, about 0.01 wt% to about 70 wt% water, and optionally not more than about 5 wt% of an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”). In any embodiments, the compositions may include 3-amino-2-butanol 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% 3-amino-2- butanol. In any embodiments, the compositions may include at least about 90 wt% 3-amino- 2-butanol.
[0024] In any embodiments the compositions may include 0.01 wt% to about 70 wt% water. 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 0.1 wt%, about 0.5 wt%, about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, about 10 wt%, about 11 wt%, about 12 wt%, about 13 wt%, about 14 wt%, about 15 wt%, about 16 wt%, about 17 wt%, about 18 wt%, about 19 wt%, about 20 wt%, about 21 wt%, about 22 wt%, about 23 wt%, about 24 wt%, about 25 wt% 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.
[0031]
[0025] In any embodiment herein, water and / or an other amino alcohol may be included in the compositions including 3 -amino-2 -butanol, e.g., to improve handling and / or modify performance characteristics. For example, addition of water to the compositions including 3- amino-2-butanol 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, 3-amino-3-methyl-2- butanol, 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)-3- methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof. The composition of any embodiment herein may include an other amino alcohol (e.g., 3- amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-
[0032] 2-methyl-l -propanol, 2-amino-l -butanol, 2-amino-2-ethyl-l,3-propanediol, 3-(ethylamino)-
[0033] 3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, 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 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., 3-amino-3-methyl-2-butanol, 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)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2- ol, 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.
[0034]
[0026] In any embodiment herein, the composition may include less than about 2 wt% secondary amine (e.g., 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-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.
[0035]
[0027] In any embodiment herein, the composition may exhibit a biobased content of the 3- amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866- 24 of 0% to 100%. For example, such ranges of biobased content of the 3-amino-2-butanol in compositions of the present technology may be provided by using purely petroleum-based 3 -amino-2 -butanol (z.e., with 0% biobased content), using 3 -amino-2 -butanol produced in part with biobased starting materials, using combinations of purely petroleum-based 3-amino- 2-butanol and 3 -amino-2 -butanol produced in part or in whole with biobased starting materials, or — for a biobased content of the 3-amino-2-butanol of 100% — using 3-amino-2- butanol produced in whole with biobased starting materials. Thus, in any embodiment herein, the composition may exhibit a biobased content of the 3-amino-2-butanol (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 the 3 -amino-2 -butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 10%, or may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 25%.
[0036] Compositions Including 3-Amino-2-butanol for Use in Conductive and Semiconductor Films
[0037]
[0028] In an aspect, the present technology provides compositions comprising 3-amino-2- butanol (also known as 3-amino-butan-2-ol; CAS No.: 42551-55-3) for use in electrical and electronic applications (e.g., conductive films including for transparent conductors and sensors, semiconductor films for sensors and photovoltaics). In particular, the present technology provides compositions useful in the manufacture of electrical and electronic devices such as batteries, integrated circuits, and photovoltaics, and provides compositions useful for the electronic materials that are important for their operation such as semiconductors. The composition may be a solution, dispersion, slurry, or paste, which may be cast, printed, sprayed, or otherwise deposited to form a conductive film, including those for a transparent conductor or sensor, or a semiconductor film, including for sensors and photovoltaics. For example, the compositions described herein may include a slurry of a conductive material and / or a semiconductor material and an additive (e.g., 3-amino-2- butanol).
[0038]
[0029] The additive may provide one or more advantages to the composition: the additive may reduce slurry viscosity so that a predetermined weight percentage of solid materials may be added to the slurry without compromising slurry casting, providing an electrical or electronic device with a predetermined conductivity; the additive may decrease the freezing point of the composition to improve handling, reduce impurities, and / or modify performance characteristics.
[0039]
[0030] The composition may include a slurry of conductive carbon. In any embodiments, the conductive carbon may include carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, carbon nanotubes (e.g., single walled carbon nanotubes, multi -walled carbon nanotubes, or a combination thereof), graphene, or a combination of any two or more thereof. For example, the composition may include carbon nanotubes (e.g., single walled carbon nanotubes, multi-walled carbon nanotubes, or a combination thereof) and an additive in a solvent (e.g., N-methyl-2-pyrrolidone (NMP) and / or water) wherein the additive comprises 3-amino-2-butanol. Some non-limiting examples of suitable solvents include certain ketones, amides, nitriles, and sulfoxides such as methyl isobutyl ketone, ethyl propyl ketone, acetophenone, dimethylformamide, N-methyl-2-pyrrolidone (NMP), acetonitrile, water (e.g., deionized water), certain glycol ethers, and dimethyl sulfoxide.
[0040]
[0031] The composition may include a slurry of a semiconductor material. In any embodiments, exemplary semiconductor materials may include silicon, silicon carbide, germanium, gallium arsenide, aluminum gallium arsenide, indium phosphide, aluminum gallium indium phosphide, indium gallium arsenide, indium arsenide antimonide phosphide, boron nitride, boron phosphide, boron arsenide, aluminum nitride, cadmium telluride, or combinations of any two or more thereof.
[0041]
[0032] In any aspect and / or embodiment herein, the composition may further include an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”), where exemplary other amino alcohols that may be included in a compositions any embodiment herein include, but are not limited to, 3-amino-3-methyl-2-butanol, 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)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, 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., 3 -amino-3-methyl-2 -butanol, 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)-3-methylbutan-2-ol, 3- (ethylamino)-butan-2-ol, 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 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., 3-amino-3-methyl-2-butanol, 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)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2- ol, 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.
[0042]
[0033] In any aspect and / or embodiment herein, the composition may exhibit a biobased content of the 3-amino-2-butanol 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 the 3-amino-2-butanol (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 the 3-amino-2- butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 10%, or may exhibit a biobased content of the 3 -amino-2 -butanol 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., 3 -amino-2 -butanol) 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).
[0043]
[0034] Conductive film compositions of the present technology may include a solvent and the additive in a weight ratio of 300: 1 to about 1 :300, e.g., about 300: 1, about 150: 1, about 75: 1, about 37: l, about 18: 1, about 9:1, about 4: 1, about 3: l, about 2: l, about 1 : 1, about 1 :2, about 1 :3, about 1 :4, about 1 :9, about 1 : 18, about 1 :37, about 1 :75, about 1 : 150, about 1 :300, or any range including and / or in-between any two of these values.
[0044]
[0035] Conductive film compositions of the present technology may include a wide range of amounts of the additive described herein (z.e., 3-amino-2-butanol). For example, the compositions may include about 0.005 wt% to about 10 wt% of 3 -amino-2 -butanol based on the total weight of the composition, e.g., about 0.01 wt% to about 10 wt%, about 0.05 wt% to about 8 wt%, about 0.05 wt% to about 5 wt%, about 0.05 wt% to about 3 wt%, about 0.05 wt% to about 2 wt%, about 0.05 wt% to about 1 wt%, about 0.1 wt% to about 20 wt%, about 0.1 wt% to about 5 wt%, about 0.1 wt% to about 1 wt%, about 0.5 wt% to about 10 wt%, or any value or subrange therebetween. In some embodiments, the compositions may include about 0.005 wt%, about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.15 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.75 wt%, about 1 wt%, about 1.5 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, or about 10 wt% of the additive, or any range including and / or inbetween any two of these values. In some embodiments, the compositions may include from about 0.1 wt% to about 1 wt% of the additive based on the total weight of the composition.
[0045]
[0036] Conductive film compositions of the present technology include a solvent. The solvent may include water, N-methyl-2-pyrrolidone, methyl isobutyl ketone, ethyl propyl ketone, acetophenone, dimethylformamide, N-methyl-2-pyrrolidone (NMP), acetonitrile, dimethyl sulfoxide, or a combination of any two or more thereof. The solvent may be used when preparing and / or applying the slurry composition. In some embodiments, the compositions may include at least about 1 wt% solvent, at least about 2 wt% solvent, at least about 5 wt% solvent, at least about 10 wt% solvent, at least about 15 wt% solvent, at least about 20 wt% solvent, at least about 25 wt% solvent, at least about 30 wt% solvent, at least about 35 wt% solvent, at least about 40 wt% solvent, at least about 45 wt% solvent, at least about 50 wt% solvent, at least about 55 wt% solvent, at least about 60 wt% solvent, at least about 70 wt%, at least about 80 wt%, at least about 90 wt%, or any range including and / or inbetween any two of these values. In some embodiments, the compositions may include about 1 wt% to about 99 wt% solvent, about 20 wt% to about 99 wt%, about 35 wt% to about 97 wt%, about 45 wt% to about 95 wt%, about 50 wt% to about 95 wt%, about 80 wt% to about 98 wt%, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include about 85 wt% to about 98 wt% solvent.
[0046]
[0037] The conductive film compositions of the present technology include a conductive material. The conductive material may be any of those known in the art. The conductive material may be a conductive carbon. In any embodiments, the conductive carbon may include carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, carbon nanotubes (e.g., single walled carbon nanotubes, multi -walled carbon nanotubes, or a combination thereof), graphene, or a combination of any two or more thereof. Typically, the present conductive film formulations include from about 0.1 wt% cathode active material to about 90 wt% cathode active material, e.g., any of about 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 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. For example, the composition may include the conductive material in an amount of about 0.2 wt.% to about 20 wt%, about 0.2 wt.% to about 10 wt%, or about 1 wt% to about 5 wt%.
[0047]
[0038] The conductive material composition of the present technology may include a component acting as a dispersant. Suitable dispersants may include polymeric dispersants such as polyvinylpyrrolidone (PVP), polyacrylic acids, polyacrylates, polyacrylamides, polyphosphoric acid esters, polyphosphoric acid salts, and the like. Suitable amounts include any of about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 1.5, 2, 3, 4, 5, 6, 7, 8, 9, 10 wt% or a range between and including any two of the foregoing values. In any embodiments the amount of dispersant may range from about 0.1 wt% to about 10 wt%, or from about 0.1 wt% to about 5 wt%, or even about 0.1 wt% to about 3 wt%.
[0048]
[0039] The conductive compositions of the present technology may further include a polymeric binder. Suitable polymeric binders include polyvinylidene fluoride, styrenebutadiene copolymer, carboxymethyl cellulose, polyacrylate latex or a mixture of any two or more thereof. In any embodiments, it may be the polymeric binder is polyvinylidene fluoride and the solvent is NMP.
[0049] Compositions Including 3-Amino-2-butanol for Use in Batteries
[0050]
[0040] In another aspect, the present technology provides compositions including 3-amino-2- butanol for use in lithium-ion batteries (LIBs) and / or battery manufacturing. In particular, the present technology provides compositions useful in the manufacture of lithium-ion batteries. The composition may be a solution, dispersion, slurry, or paste, which may be cast, printed, sprayed, or otherwise deposited to form a lithium-ion battery component (e.g., a cathode, anode, or separator). For example, the compositions described herein may include a polymer and an additive (e.g., 3 -amino-2 -butanol) in solution intended for use in preparing polymer separators for lithium-ion batteries. For example, the compositions described herein may include a slurry of an electrode active material and an additive (e.g., 3 -amino-2 -butanol) intended for use in preparing electrodes for lithium-ion batteries.
[0051]
[0041] In some embodiments, the additive may reduce slurry viscosity so that a predetermined weight percentage of solid materials may be added to the slurry without compromising slurry casting, providing an electrode with a predetermined conductivity and energy storage capacity. In some embodiments, the additive may decrease the freezing point of the composition to improve handling, reduce impurities, and / or modify performance characteristics. As discussed previously, in any aspect and / or embodiment herein, the composition may exhibit a biobased content of the 3 -amino-2 -butanol 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 the 3-amino-2- butanol (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.
[0052]
[0042] Compositions of the present technology may include a wide range of amounts of the additive described herein (z.e., 3 -amino-2 -butanol). For example, the compositions may include about 0.005 wt% to about 10 wt% of 3-amino-2-butanol based on the total weight of the composition, e.g., about 0.01 wt% to about 10 wt%, about 0.05 wt% to about 8 wt%, about 0.05 wt% to about 5 wt%, about 0.05 wt% to about 3 wt%, about 0.05 wt% to about 2 wt%, about 0.5 wt% to about 10 wt%, or any value or subrange therebetween. In some embodiments, the compositions may include about 0.005 wt%, about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.15 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.75 wt%, about 1 wt%, about 1.5 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, or about 10 wt% of the additive, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include from about 0.2 wt% to about 2 wt% of the additive based on the total weight of the composition.
[0053]
[0043] Compositions of the present technology may include a solvent. The solvent may be any suitable polar solvent known in the art, e.g., water, methyl isobutyl ketone, ethyl propyl ketone, acetophenone, dimethylformamide, N-methyl-2-pyrrolidone (NMP), acetonitrile, dimethyl sulfoxide, or a combination of any two or more thereof. The N-methyl-2- pyrrolidone may be used as a solvent when preparing and / or applying the slurry composition. In some embodiments, the compositions may include at least about 1 wt% solvent, at least about 2 wt% solvent, at least about 5 wt% solvent, at least about 10 wt% solvent, at least about 15 wt% solvent, at least about 20 wt% N-methyl-2-pyrrolidone, at least about 25 wt% N-methyl-2-pyrrolidone, at least about 30 wt% N-methyl-2-pyrrolidone, at least about 35 wt% N-methyl-2-pyrrolidone, at least about 40 wt% N-methyl-2-pyrrolidone, at least about 45 wt% N-methyl-2-pyrrolidone, at least about 50 wt% N-methyl-2-pyrrolidone, at least about 55 wt% N-methyl-2-pyrrolidone, at least about 60 wt% N-methyl-2-pyrrolidone, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include about 1 wt% to about 99 wt% N-methyl-2-pyrrolidone, about 20 wt% to about 99 wt% N-methyl-2-pyrrolidone, about 35 wt% to about 97 wt%, about 45 wt% to about 95 wt%, about 50 wt% to about 95 wt%, about 80 wt% to about 98 wt%, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include about 20 wt% to about 80 wt% N-methyl-2-pyrrolidone.
[0054] LIB Cathode Formulations
[0055]
[0044] The LIB cathode formulations of the present technology include a cathode active material. The cathode active material may be any of those known in the art. In any embodiments, the cathode active material may include lithium nickel manganese cobalt oxides (NMC, LiNixMnyCozCh), lithium iron phosphate (LFP, LiFePCh), lithium cobalt oxide (LCO, LiCoCh), lithium manganese oxide (LMO, LiM Ch), lithium nickel cobalt aluminum oxide (NCA, LiNiCoAlCh), lithium titanate (LTO, Li2TiO3), lithium manganese iron phosphate (LMFP, LiMnxFe(i-X)PO4) or a mixture thereof. Typically, the present LIB cathode formulations include from about 5 wt% cathode active material to about 99 wt% cathode active material, e.g., any of about 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or 99 wt%, or a range between and including any two of the foregoing values. For example, the composition may include the cathode active material in an amount of about 95 wt% to about 99 wt% or about 96 wt% to about 99 wt%.
[0056]
[0045] In any embodiments of the present technology, the LIB cathode formulations may include from about 20 wt% to about 70 wt% LFP. For example, the LFP may be present at any of about 20, 25, 30, 30, 40, 45, 50, 55, 60, 65, or 70 wt% or a range between and including any two of the foregoing values. For example, the LIB cathode formulation may include about 20 wt% to about 70 wt% LFP. In any embodiments, the cathode formulations may include from about 40 wt% to about 80 wt% NCA. For example, the NCA may be present at any of about 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, or 80 wt% NCA or a range between and including any two of the foregoing values. For example, the NCA cathode formulation may include about 50 wt% or about 55 wt% to about 70 wt% NCA. In any embodiments, the cathode formulations may include about 30 wt% to about 80 wt% LMFP. For example, the LMFP may be present at any of about 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, or 80 wt% LMFP or a range between and including any two of the foregoing values. For example, the LMFP cathode formulation may include about 60 wt% to about 70 wt% or about 50 wt% LMFP.
[0057]
[0046] The LIB cathode formulation of the present technology may include a solvent (that acts as a dispersant). The solvent may include water and / or any suitable polar organic solvent known in the art, e.g., those with a dielectric constant of at least 15, e.g., 15, 20, 25, 30, 35, 40, 45 or more or a range between and including any two of the foregoing values. Some nonlimiting examples of suitable solvents include certain ketones, amides, nitriles, and sulfoxides such as methyl isobutyl ketone, ethyl propyl ketone, acetophenone, dimethylformamide, N- methyl-2-pyrrolidone (NMP), acetonitrile, and / or dimethyl sulfoxide. In any embodiments, the solvent may be NMP. LIB cathode formulations of the present technology may include about 0.1 wt% to about 99 wt% solvent. Thus, suitable amounts include any of about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 50, 60, 70, 80, ;90, 95, 96, 97, 98, or 99 wt% or a range between and including any two of the foregoing values. In any embodiment, the amount of solvent may range from about 10 wt% to about 99 wt%, or from about 20 wt% to about 95 wt%, or even about 30 wt% to about 90 wt%.
[0058]
[0047] The LIB cathode formulation of the present technology may include a component acting as a dispersant. Suitable dispersants may include polymeric dispersants such as polyvinylpyrrolidone (PVP), polyacrylic acids, polyacrylates, polyacrylamides, polyphosphoric acid esters, polyphosphoric acid salts, and the like. Suitable amounts include any of about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 1.5, 2, 3, 4, 5, 6, 7, 8, 9, 10 wt% or a range between and including any two of the foregoing values. In any embodiments the amount of dispersant may range from about 0.1 wt% to about 10 wt%, or from about 0.1 wt% to about 5 wt%, or even about 0.1 wt% to about 3 wt%.
[0059]
[0048] The LIB cathode formulations of the present technology may further include a polymeric binder. Suitable polymeric binders include polyvinylidene fluoride, styrenebutadiene copolymer, carboxymethyl cellulose, polyacrylate latex or a mixture of any two or more thereof. In any embodiments, it may be the polymeric binder is polyvinylidene fluoride and the solvent is NMP.
[0060]
[0049] The LIB cathode formulation of the present technology in any embodiments may further include a conductive agent. By “conductive agent” is meant any chemical or substance that increases the electrical conductivity of an electrode, including the cathode of a LIB. In any embodiments, the conductivity agent may include carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, carbon nanotubes (e.g., single walled carbon nanotubes, multi-walled carbon nanotubes, or a combination thereof), graphene, or a combination of any two or more thereof.
[0061]
[0050] As discussed previously, in any embodiment herein of the LIB cathode formulation of the present technology, the LIB cathode formulation may exhibit a biobased content of the 3- amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866- 24 of 0% to 100% — thus, in any embodiment herein, the LIB cathode formulation may exhibit a biobased content of the 3 -amino-2 -butanol (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.
[0062] LIB Anode Formulations
[0063]
[0051] The LIB anode formulations of the present technology include an anode active material. The anode active material may be any of those known in the art. In any embodiments, the anode active material may be selected from the group consisting of lithium, graphite, silicon, or a mixture or composite, thereof. Typically, the present LIB anode formulations include from about 5 wt% anode active material to about 99 wt% anode active material, e.g., any of about 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or 99 wt%, or a range between and including any two of the foregoing values. For example, the composition may include the anode active material in an amount of about 95 wt% to about 99 wt% or about 96 wt% to about 99 wt%.
[0064]
[0052] The LIB anode formulation of the present technology may include a solvent (that acts as a dispersant). The solvent may be water and / or any suitable polar organic solvent known in the art, e.g., those with a dielectric constant of at least 15, e.g., 15, 20, 25, 30, 35, 40, 45 or more or a range between and including any two of the foregoing values. Some non-limiting examples of suitable solvents include certain ketones, amides, nitriles, and sulfoxides such as methyl isobutyl ketone, ethyl propyl ketone, acetophenone, dimethylformamide, N-methyl-2- pyrrolidone (NMP), acetonitrile, and dimethyl sulfoxide. In any embodiments, the solvent may be NMP. LIB anode formulations of the present technology may include about 0.1 wt% to about 99 wt% solvent. Thus, suitable amounts include any of about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 50, 60, 70, 80, ;90, 95, 96, 97, 98, or 99 wt% or a range between and including any two of the foregoing values. In any embodiments, the amount of solvent may range from about 10 wt% to about 99 wt%, or from about 20 wt% to about 95 wt%, or even about 30 wt% to about 90 wt%.
[0065]
[0053] The LIB anode formulation of the present technology may include a component acting as a dispersant. Suitable dispersants may include polymeric dispersants such as polyvinylpyrrolidone (PVP), polyacrylic acids, polyacrylates, polyacrylamides, polyphosphoric acid esters, polyphosphoric acid salts, and the like. Suitable amounts include any of about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 1.5, 2, 3, 4, 5, 6, 7, 8, 9, 10 wt% or a range between and including any two of the foregoing values. In any embodiments the amount of dispersant may range from about 0.1 wt% to about 10 wt%, or from about 0.1 wt% to about 5 wt%, or even about 0.1 wt% to about 3 wt%.
[0066]
[0054] The LIB anode formulations of the present technology may further include a polymeric binder. Suitable polymeric binders include polyvinylidene fluoride, styrene- butadiene copolymer (SBR), carboxymethyl cellulose (CMC), polyacrylate latex or a mixture of any two or more thereof. For example, the polymeric binder may be CMC or SBR and the solvent may be water.
[0067]
[0055] The LIB anode formulation of the present technology in any embodiments may further include a conductive agent. By “conductive agent” is meant any chemical or substance that increases the electrical conductivity of an electrode, including the anode of a LIB. In any embodiments, the conductivity agent may be selected from the group consisting of carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, carbon nanotubes, graphene, or a combination of any two or more thereof.
[0068]
[0056] As discussed previously, in any embodiment herein of the LIB anode formulation of the present technology, the LIB anode formulation may exhibit a biobased content of the 3- amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866- 24 of 0% to 100% — thus, in any embodiment herein, the LIB anode formulation may exhibit a biobased content of the 3-amino-2-butanol (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.
[0069] Lithium-Ion Battery (LIB) Separator Formulations
[0070]
[0057] The LIB separator formulations of the present technology may include a polymer that may be used to form a LIB separator. The separator polymer may be any of those known in the art. In any embodiments, the separator polymer may be selected from the group consisting of polyethylene, polypropylene, poly(vinylidene fluoride), polyamide, polyethylene oxide, or any combination or copolymer of any two or more thereof. Typically, the present LIB separator formulations include from about 5 wt% separator polymer to about 90 wt% separator polymer, e.g., any of about 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. For example, the composition may include the separator polymer in an amount of about 5 wt.% to about 50 wt% or about 50 wt% to about 20 wt%.
[0071]
[0058] The LIB separator formulations of the present technology may include a solvent (that acts as a dispersant). The solvent may include any suitable polar organic solvent known in the art, e.g., those with a dielectric constant of at least 15, e.g., 15, 20, 25, 30, 35, 40, 45 or more or a range between and including any two of the foregoing values. Some non-limiting examples of suitable solvents include certain ketones, amides, nitriles, and sulfoxides such as methyl isobutyl ketone, ethyl propyl ketone, acetophenone, dimethylformamide, N-methyl-2- pyrrolidone (NMP), acetonitrile, and / or dimethyl sulfoxide. In any embodiments, the solvent may be NMP. LIB separator formulations of the present technology may include about 0.1 wt% to about 99 wt% solvent. Thus, suitable amounts include any of about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 50, 60, 70, 80, ;90, 95, 96, 97, 98, or 99 wt% or a range between and including any two of the foregoing values. In any embodiment, the amount of solvent may range from about 10 wt% to about 99 wt%, or from about 20 wt% to about 99 wt%.
[0072]
[0059] The LIB formulations of the present technology may include a solvent, 3-amino-2- butanol mixed into the solvent, and particles of a ceramic material dispersed in the mixture. These formulations may be used to coat a LIB separator with a ceramic coating, to improve safety of the separator. Non-limiting examples of the ceramic may include aluminum oxide hydroxide (e.g., boehmite having the formula y-AlO(OH)), a-A12O3 and SiCh.
[0073]
[0060] The LIB separator formulations of the present technology may include a component acting as a dispersant. Suitable dispersants may include polymeric dispersants such as polyvinylpyrrolidone (PVP), polyacrylic acids, polyacrylates, polyacrylamides, polyphosphoric acid esters, polyphosphoric acid salts, and the like. Suitable amounts include any of about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 1.5, 2, 3, 4, 5, 6, 7, 8, 9, 10 wt% or a range between and including any two of the foregoing values. In any embodiment, the amount of dispersant may range from about 0.1 wt% to about 10 wt%, or from about 0.1 wt% to about 5 wt%, or even about 0.1 wt% to about 3 wt%.
[0061] As discussed previously, in any embodiment herein of the LIB separator formulation of the present technology, the LIB separator formulation may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of 0% to 100% — thus, in any embodiment herein, the LIB separator formulation may exhibit a biobased content of the 3-amino-2-butanol (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.
[0074] Compositions Including 3-Amino-2-butanol for Use in Semiconductor Devices
[0075]
[0062] In another aspect, the present technology provides compositions including 3-amino-2- butanol for use in semiconductor materials and devices. In particular, the present technology provides compositions useful in the manufacture of semiconductor materials and devices as a cleaning formulation. The composition may be a solution, dispersion, slurry, or paste. For example, the compositions described herein may include a solvent and an additive (e.g., 3- amino-2-butanol) intended for use in preparing semiconductor devices (e.g., diodes, transistors, integrated circuits, photonic devices, memory devices, or sensors). The composition may be applied to the surface of a semiconductor material to increase hydrophilicity of the surface (e.g., by reducing contaminants). The composition may be applied to the surface of a semiconductor device in the process of manufacturing to remove particles and ensure the cleanliness of the surface of the semiconductor before further processing. For example, the cleaning formulation may be applied to a semiconductor substrate before and / or after chemical mechanical planarization to increase smoothness and reduce contaminants on the surface. As another example, the cleaning formulation may be applied to a silicon dioxide wafer to remove particles formed before and / or during cleaning and obtain precise planarization and a smooth, defect-free or substantially defect-free surface. As another example, the cleaning formulation may be applied to an aluminum metal surface to reduce contaminants on the surface. As another example, the cleaning formulation may be used as a chemical etchant for thin film transistor (TFT) panels where the 3-amino-2-butanol -containing etchant will have comparable or better performance than those formulated without 3-amino-2-butanol. As another example, cleaning and stripping solutions for printed circuit boards (PCBs) may be formulated to include 3 -amino-2 -butanol.
[0076]
[0063] Compositions of the present technology may include a wide range of amounts of the additive described herein (z.e., 3 -amino-2 -butanol). For example, the compositions may include about 0.001 wt% to about 40 wt% of 3-amino-2-butanol based on the total weight of the composition, e.g., about 0.001 wt% to about 2 wt%, about 0.01 wt% to about 1 wt%, about 0.03 wt% to about 0.5 wt%, about 0.05 wt% to about 0.3 wt%, about 0.01 wt% to about 10 wt%, about 0.05 wt% to about 8 wt%, about 0.05 wt% to about 5 wt%, about 0.05 wt% to about 3 wt%, about 0.05 wt% to about 2 wt%, about 0.5 wt% to about 10 wt%, or any value or subrange therebetween. In some embodiments, the compositions may include about 0.001 wt%, about 0.005 wt%, about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.15 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.75 wt%, about 1 wt%, about 1.5 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, about 10 wt%, about 20 wt%, about 30 wt%, about 40 wt% of the additive, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include from about 0.05 wt% to about 0.3 wt% of the additive based on the total weight of the composition.
[0077]
[0064] The semiconductor cleaning formulations of the present technology may include a solvent. The solvent may be water or any suitable polar organic solvent known in the art, e.g., those with a dielectric constant of at least 15, e.g., 15, 20, 25, 30, 35, 40, 45 or more or a range between and including any two of the foregoing values. Some non-limiting examples of suitable solvents include certain ketones, amides, nitriles, and sulfoxides such as methyl isobutyl ketone, ethyl propyl ketone, acetophenone, dimethylformamide, N-methyl-2- pyrrolidone (NMP), acetonitrile, water (e.g., deionized water), certain glycol ethers, and / or dimethyl sulfoxide. In any embodiments, the solvent may be water, NMP, or a combination thereof. The semiconductor cleaning formulation may include at least about 20 wt% solvent, at least about 25 wt% solvent, at least about 30 wt% solvent, at least about 35 wt% solvent, at least about 40 wt% solvent, at least about 45 wt% solvent, at least about 50 wt% solvent, at least about 55 wt% solvent, at least about 60 wt% solvent, at least about 70 wt%, at least about 80 wt%, at least about 90 wt%, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include about 10 wt% to about 99 wt%, about 20 wt% to about 99 wt% solvent, about 35 wt% to about 97 wt%, about 45 wt% to about 95 wt%, about 50 wt% to about 95 wt%, about 50 wt% to about 90 wt%, about 80 wt% to about 98 wt%, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include about 85 wt% to about 98 wt% solvent.
[0078]
[0065] As an example, semiconductor cleaning formulations may include about 0.001 wt% to about 40 wt% of 3-amino-2-butanol and about 10 wt% to about 99 wt% glycol ether. The glycol ether may be any glycol ether having a viscosity suitable for use in semiconductor cleaning formulations. For example, the glycol ether may be butyldiglycol, 2-(2- ethoxyethoxy)ethanol (also referred to as carbitol), or a combination thereof. In some embodiments, the semiconductor cleaning formulation may include about 2 wt% to about 40 wt% of N-methyl pyrrolidone. In some embodiments, the semiconductor cleaning formulation may include about 2 wt% to about 60 wt% water.
[0079]
[0066] The semiconductor cleaning compositions may include one or more additional cleaning agents. Suitable cleaning agents may include etching agents, agents that remove organic residues, and agents that remove particulate contaminants. Such agents include oxidizing agents (e.g., hydrogen peroxide or a peroxy acid), oxalic acid, benzotriazole, quaternary ammonium salts e.g., tetramethylammonium hydroxide), gallic acid, dodecylbenzene sulfonic acid, and / or hydroxylamine.
[0080]
[0067] The semiconductor cleaning compositions may include about 0.005 wt% to about 40 wt% of the additional agent based on the total weight of the composition, e.g., about 0.01 wt% to about 40 wt%, about 2 wt% to about 40 wt%, about 5 wt% to about 40 wt%, about 10 wt% to about 40 wt%, about 20 wt% to about 40 wt%, about 30 wt% to about 40 wt%, about 0.05 wt% to about 8 wt%, about 0.05 wt% to about 5 wt%, about 0.05 wt% to about 3 wt%, about 0.05 wt% to about 2 wt%, about 0.01 wt% to about 1 wt%, about 0.5 wt% to about 10 wt%, or any value or subrange therebetween. In some embodiments, the compositions may include about 0.005 wt%, about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.15 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.75 wt%, about 1 wt%, about 1.5 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, or about 40 wt% of the additional agent, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include from about 2 wt% to about 40 wt%, about 0.05 wt% to about 2 wt%, about 0.2 wt% to about 2 wt%, or about 0.01 wt% to about 1 wt% of the additional agent based on the total weight of the composition.
[0081]
[0068] The semiconductor cleaning compositions may include about 2 wt% to about 40 wt% of oxalic acid. The semiconductor cleaning compositions may include about 0.01 wt% to about 1 wt% benzotri azole. The semiconductor cleaning compositions may include about 0.01 wt% to about 1 wt% gallic acid. The semiconductor cleaning compositions may include about 0.05 wt% to about 2 wt% dodecylbenzene sulfonic acid.
[0082]
[0069] The semiconductor cleaning composition may have a pH of about 2 to about 11, e.g., about 3 to about 10, about 4 to about 10, about 2 to about 6, about 3 to about 5, about 8 to about 11, about 9 to about 10, or any value or subrange therebetween. In some embodiments, the compositions may include have a pH of about 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, or any range including and / or in-between any two of these values. In some embodiments, the compositions may have a pH of about 4.5 or about 9.5.
[0083]
[0070] As discussed previously, in any embodiment herein of the semiconductor cleaning composition of the present technology, the semiconductor cleaning composition may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of 0% to 100% — thus, in any embodiment herein, the semiconductor cleaning composition may exhibit a biobased content of the 3-amino-2- butanol (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. Methods of Manufacturing Compositions
[0084] Conductive Film and Battery Compositions
[0085]
[0071] The conductive film and battery compositions described herein may be manufactured by conventional film formation or battery manufacturing techniques, respectively, which are well known to those skilled in the art. Typically, the compositions are manufactured by a three-step process. First, a solid component phase may be prepared by mixing the solid powder components (e.g., electroactive materials and / or conductive materials). This part of the process is designed to dis-agglomerate solid powders to form a uniformly dispersed state. In the second step of the manufacturing process, a solution of liquid components may be prepared by mixing any liquid components, if present, in the solvent. In the third step of the manufacturing process, the mixed powder may be dispersed in the solution and additional components (e.g., binders and dispersants) may be dissolved in the solution.
[0086]
[0072] The additive (e.g., 3 -amino-2 -butanol) may be added to the composition at one or more of three different places in the manufacturing process: to the solid powder dispersion (grinding), to the binder dispersion, and / or in a final addition to the composition.
[0087] Semiconductor Cleanins Compositions
[0088]
[0073] The semiconductor cleaning compositions described herein may be manufactured by conventional solution preparation techniques, which are well known to those skilled in the art. Typically, the compositions are manufactured by a two-step process. First, the additive and additional cleaning agents may be dissolved or dispersed in a solvent. In the second step, the pH of the solution may be adjusted to a predetermined value by adjusting the concentration of the additive and additional cleaning agents in solution.
[0089]
[0074] Unless otherwise indicated, numeric ranges, for instance as in "from 2 to 10," are inclusive of the numbers defining the range (e.g., 2 and 10).
[0090]
[0075] Unless otherwise indicated, ratios, percentages, parts, and the like are by weight.
[0091]
[0076] 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 or aspects of the present technology.
[0092] EXAMPLES
[0093] General Information
[0094]
[0077] The IUPAC names and abbreviations of the compounds tested herein are provided below.
[0095] Example 1. Synthesis of 3-Amino-2-Butanol
[0096] Synthesis of 3-amino-2-butanol (3-AB),
[0078] Nitroethane (1 mol, 97%,) and bio-acetaldehyde (1 mol, 99%, MilliporeSigma) were added to triethylamine (0.02 mol, MilliporeSigma) in methanol while maintaining the temperature below 50 °C. The mixture was stirred at 50 °C for 2 h, then stirred at ambient temperature overnight. GC-FID analysis indicated 95% conversion of NE to 3-NB.
[0097]
[0079] The reaction mixture was then fed into a stainless-steel reactor containing Raney Nickel (10 wt%) and methanol with 650 psi hydrogen at 45-65 °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 159 °C and recovered as a colorless liquid. The isolated yield was 70 % and the purity was 99 % 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 chromatograph: Agilent model 7890, Series II).
[0098] Example 2. 3AB-Containing Cleaning Solutions for Cleaning Printed Circuit Boards
[0099]
[0080] Cleaning solution for printed circuit boards (PCBs) may be formulated as shown in Table 1. TEOS wafers were treated with the cleaning solutions, where the additive was 3 AB, AMP, or SC-1 (SC-1 is a mixture of ammonium hydroxide, hydrogen peroxide, and deionized water having a pH of 9.5; a standard cleaning solution in the semiconductor industry). Each of the cleaning solutions was adjusted to have a pH of 9.5.
[0100] Table 1. Cleaning Formulations
[0101]
[0081] The results are summarized in FIG. 1. FIG. 1 provides a graph of the results of dynamic contact angle measurements of silicon wafers treated with different semiconductor cleaning solutions (2-amino-2-methyl-l -propanol (“AMP”); SC-1 (SC-1 is a mixture of ammonium hydroxide, hydrogen peroxide, and deionized water having a pH of 9.5; a standard cleaning solution in the semiconductor industry; or amino-2-butanol (“3-AB”, of the present technology). Cleaning solutions had a pH of 9.5. The results shown in FIG. 1 indicated that wafers cleaned with 3AB had a contact angle lower than that treated with AMP or SC-1.
[0102] Example 3. Post-Chemical Mechanical Planarization (CMP) Cleaning Formulation Including 3AB
[0103]
[0082] Post-CMP cleaning formulations were prepared with the components shown in Table 2. The formulations had a pH of about 9.5.
[0104] Table 2. Post-CMP Cleaning Formulations
[0105]
[0083] To prepare samples, 1x1” TEOS silicon wafers were submerged in a 1.0 wt% CeCh nanoparticle dispersion at pH 5.6 three times. This was followed by a further three dips in pH 5.6 deionized water in order to remove loosely bound particles. Following the dipcoating, the wafers were dried with compressed air. The coated TEOS wafers were then imaged using a JCM 7000 Neoscope Benchtop SEM (3500* zoom, low vacuum, high probe current, BED-S signal, 10.0 kV landing voltage, 12.5 working distance, slow scan, 5120x3840 image) in 9 different locations per wafer.
[0106]
[0084] Treatment with the different cleaning formulations were conducted using contact or non-contact cleaning modes. Contact cleaning was conducted as follows. The coated wafers were cleaned using a 3-inch section from a polyvinyl alcohol (PVA) brush (H3FEN). The brush piece was attached to a 3D printed component attached to a motor, which rotated the brush at 300 rpm with 0.3 g pressure. During wafer cleaning, fresh cleaning solutions (1000 pM, pH 9.5) was supplied to the brush via a peristaltic pump at 75.0 mL / min. The cleaned TEOS wafers were then imaged via SEM as described above in the same 9 locations on the wafer.
[0107]
[0085] Noncontact cleaning was performed using a megasonic reactor bowl. Coated TEOS coupons were submerged into a megasonic reactor (Bowl Meg®, Prosys Inc) containing 250 mL of each cleaning solution and sonicated at 60 W for 1 minute. Fresh cleaning chemistry (1000 pM additive concentration) was supplied between trials to avoid recontamination.
[0108]
[0086] SEM images were analyzed using Fiji (ImageJ) software to quantify particles on the surface. Particle removal efficiency was calculated for each location on the wafer as follows: where County — particle count of wafer,
[0109] County — particle count of dirty wafer
[0110]
[0087] The results are summarized in FIGS. 2A-2C. FIGS. 2A-2C provide particle removal efficiency (“PRE (%)”) of TEOS wafers treated with different semiconductor cleaning solutions using contact and non-contact cleaning conditions. FIG. 2A is a graph of contact cleaning with different semiconductor cleaning solutions (deionized water (“DI”), SC-1, triethanolamine (“TEA”), Tris(hydroxymethyl)aminomethane (“TA”), 2-amino-2-methyl-l- propanol (“AMP”), or amino-2-butanol (“3-AB”, of the present technology). FIG. 2B is a graph of non-contact cleaning with different semiconductor cleaning solutions (3-amino-4- octanol (“Corrguard EXT”), 2-amino-2-methyl-l -propanol (“AMP”), or amino-2 -butanol (“3-AB”, of the present technology). FIG. 2C is a graph of contact cleaning with different semiconductor cleaning solutions (3-amino-4-octanol (“Corrguard EXT”), 2-amino-2- methyl-1 -propanol (“AMP”), or amino-2 -butanol (“3-AB”, of the present technology). The results shown in FIGS. 2A-2C indicated that wafers cleaned with 3AB demonstrated comparable or better cleaning than AMP based on percent particle removal efficiency (PRE).
[0111] Example 4. Aluminum Metal Surface Cleaning with Different Cleaning Formulations Including 3AB
[0112]
[0088] Contact angle analysis of various concentrations of the cleaning solutions (3 AB and AMP) were tested on bare aluminum metal samples. A 15 pL drop of each cleaning chemistry at pH 9.5 was pipetted on the surface of a clean, bare aluminum sample while filming a 10 second video (240 fps) using a CASIO Exilim HS EX-ZR700 camera. The video was then uploaded to FrameShots software where the video was split into images at 1 second intervals. The images were uploaded to Fiji (Imaged) software to measure the initial contact angle (t=0 seconds) and the dynamic contact angle (t=0 seconds to t=l 0 seconds) using the Drop Analysis-LB-ADSA plugin.
[0113]
[0089] Results of normalized average contact angle after cleaning with cleaning solutions at cleaning times of up to 10 seconds (s) are shown in FIGS. 3A-3B. FIGS. 3A-3B provide contact angle of aluminum surfaces treated with different semiconductor cleaning solutions at different concentrations. FIG. 3 A is a graph of initial contact angle of aluminum surfaces treated with different semiconductor cleaning solutions (2-amino-2-m ethyl- 1 -propanol (“AMP”) or amino-2 -butanol (“3-AB”, of the present technology). FIG. 3B is a graph of dynamic contact angle of aluminum surfaces treated with different semiconductor cleaning solutions (2-amino-2-methyl-l -propanol (“AMP”) or amino-2-butanol (“3-AB”, of the present technology). The results shown in FIGS. 3 A-3B indicated that aluminum cleaned with 3AB demonstrated comparable or better cleaning than AMP based on initial and dynamic contact angle analysis at all cleaning times. Example 5: Critical Micelle Concentration of Formulations Including 3AB
[0114]
[0090] Solutions for each indicated amnio alcohol (z.e., 2-amino-2-m ethyl- 1 -propanol (“AMP”) or amino-2 -butanol (“3-AB”)) were prepared at pH 9.5 at varying concentrations for each amino alcohol (0.001, 0.05, 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2 Molar). Each solution was examined using an Atago pocket refractometer to determine its refractive index. KCPS data was collected for each solution using a Malvern ZetaSizerNano ZS with disposable plastic cuvette sample holders, and the SOP was updated with each solution's respective refractive index. KCPS data was averaged across a minimum of ten trials and plotted against concentration to determine critical micelle concentration.
[0115]
[0091] FIGS. 4A-4B provide critical micelle concentration with different additives (2-amino- 2-methyl-l -propanol (“AMP”) or amino-2 -butanol (“3-AB”, of the present technology) and different concentrations, measured using light scattering intensity measured in kilocounts per second (“kcps”). FIG. 4A is a graph of critical micelle concentration for 3AB. FIG. 4B is a graph of critical micelle concentration for AMP. The results indicate 3AB provides similar critical micelle concentration as AMP.
[0116] Example 6 - Lithium Iron Phosphate Slurry for Lithium-Ion Batteries
[0117]
[0092] Slurry dispersions of the cathode material lithium iron phosphate (LiFePO4; “LFP”) were prepared with AMP, 3-AB and / or a phosphoric ester (such as DV2703 from Solvay, BYK ET 3000 from BYK, etc) as shown in Table 3. Formulation Comp. 1 is comparison formulation without any dispersant additives, Comp. 2 included a commercial phosphoric ester (DV2703 from Solvay) as the dispersant, and Comp. 3 included AMP as dispersant. Sample 1 included 3-AB as a dispersant, and Sample 2 included the commercial phosphoric ester (DV2703 from Solvay) together with 3-AB. To form the formulations, polyvinylidene fluoride (PVDF Solef 5130 from Solvay) was dissolved in NMP solvent at a concentration of about 5 wt% PVDF in NMP solution. The dispersants, LFP, NMP, Super P carbon black (SP), and pre-prepared PVDF in NMP solution were weighed into a plastic container. Then the mixture was mixed using a planetary centrifugal mixer (Thinky ARE 310) at 2,000 rpm for 2 minutes. The mixture was further mixed with handheld homogenizer (IKA T18) at 23,000 rpm for 5 minutes. The solids weight ratio of LFP:SP:PVDF was 95:2.5:2.5. The solids weight ratio was based on the solids in the slurry, not based on the total weight. The total weight percentage of solids in the resulting slurry was 49 wt%. All formulations were tested for viscosity and stability of the slurries. Viscosity was tested using a viscometer (Brookfield DV2T) at the speed of 12 rpm with spindle #64.
[0118]
[0093] The results are summarized in Table 4. The results indicated that dispersants 3-AB and AMP in LFP slurries led to a lower and more stable viscosity compared to the sample without dispersant and with phosphoric ester dispersant, where 3-AB exhibited much better performance than AMP and further improvement was achieved by using 3-AB together with a phosphoric ester.
[0119] Table 3. LFP Electrode Slurries with AMP, 3-AB, and DV2703
[0120] Table 4. Viscosity of LFP electrode slurries at 12 rpm with spindle #64 Example 7 - Lithium Manganese Iron Phosphate Slurry for Lithium-Ion Batteries
[0121]
[0094] Slurry dispersions including the cathode active material lithium manganese iron phosphate (LiMnxFe(i-X)P04, LMFP) were prepared with AMP, 3-AB, or a phosphoric ester (such as DV2703 from Solvay, BYK ET 3000 from BYK, etc) having the formulations shown in Table 5. Formulation Comp. 4 is comparison formulation without any dispersant additives, Comp. 5 included commercial phosphoric ester (DV2703 from Solvay) as dispersant, and Comp. 6 included AMP as the dispersant. Sample 3 included 3-AB as dispersant. Viscosity with different addition amount of 3-AB was also tested. All formulations were tested for viscosity and stability of the slurries. To form the formulation, PVDF was dissolved in NMP solvent to make a solution with 5 wt% PVDF in NMP.
[0122] Amounts of dispersant, LMFP, NMP, Super P carbon black (SP), and PVDF in NMP solution were weighted into a plastic container. Then the mixture was mixed using a planetary centrifugal mixer (Thinky ARE 310) at 2,000 rpm for 5 minutes. The mixture was further mixed with handheld homogenizer (IKA T18) at 23,000 rpm for 5 minutes. The solids weight ratio of LMFP: SP: PVDF was 96: 1 :3. The solids weight ratio was based on the solids in the slurry, not based on the total weight. The total weight percentage of solids in the resulting slurry was 48 wt%. Viscosity was tested using a viscometer (Brookfield DV2T) at the speed of 12 rpm with spindle #64.
[0123]
[0095] The results are summarized in Table 6. The results indicated that using 3-AB as the dispersant in LMFP slurry led to a lower and more stable viscosity compared to compositions without dispersants and the other dispersents.
[0124]
[0096] The dispersing performance of different amount of 3-AB from 0 to 0.8% (by weight) in the LMFP slurries was studied. The viscosity performance of the slurries were measured at 0 hour, 6 hours, and 24 hours. The results were shown in Table 7. The viscosity decreased further when the amount of 3-AB increased in the formulation. The higher the amount of 3- AB, the lower viscosity of the slurry. The viscosities of the fresh (0 h) and aged (6 and 12 h) slurries showed the consistent trend of improved performance of viscosity and its stability. Further increase of the amount of 3-AB may improve the dispersing performance of the slurries even further. Table 5. LMFP electrode slurries with different dispersants
[0125] Table 6. Viscosity of LMFP electrode Slurries with different dispersants
[0126]
[0097]
[0127] Table 7. Viscosity of LMFP electrode slurries with different amounts of 3-AB upon different storage time (0 hour, 6 hours and 24 hours) EQUIVALENTS
[0128]
[0098] 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.
[0129]
[0099] 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.
[0130]
[0100] 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.
[0131]
[0101] 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.
[0132]
[0102] 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.
[0133]
[0103] All publications, patent applications, issued patents, and other documents (for examplejournals, articles and / or textbooks) referred to in this specification are herein 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.
[0134]
[0104] 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:
[0135] A. A composition comprising a solvent and 3-amino-2-butanol in a weight ratio of 300: 1 to about 1 :300, optionally wherein the composition exhibits a biobased content of the 3- amino-2-butanol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24, optionally wherein the solvent is a non-aqueous solvent.
[0136] B. The composition of Paragraph A, comprising the solvent and 3-amino-2-butanol in a weight ratio of 2: 1 to about 1 :2.
[0137] C. The composition of Paragraph A or Paragraph B, wherein the solvent comprises methyl isobutyl ketone, ethyl propyl ketone, acetophenone, dimethylformamide, N-methyl-2- pyrrolidone (NMP), acetonitrile, dimethyl sulfoxide, or a combination of two or more thereof, optionally wherein the solvent is a non-aqueous solvent.
[0138] D. The composition of Paragraph A, comprising about 40 wt% to about 99 wt% solvent and about 0.01 wt% to about 10 wt% 3-amino-2-butanol.
[0139] E. The composition of any one of Paragraphs A-D, further comprising a conductive material, a semiconductor material, or a combination thereof.
[0140] F. The composition of Paragraph E, comprising about 5 wt% to about 90 wt% conductive material.
[0141] G. The composition of Paragraph E or Paragraph F, wherein the conductive material comprises a lithium-ion battery cathode material.
[0142] H. The composition of Paragraph G, wherein the lithium-ion battery cathode material comprises lithium iron phosphate, lithium manganese iron phosphate, lithium nickel manganese cobalt oxide, lithium cobalt oxide, lithium nickel oxide, lithium manganese oxide, lithium nickel cobalt aluminum oxide, lithium titanate, or a combination of any two or more thereof. I. The composition of Paragraph G or Paragraph H, wherein the lithium-ion battery cathode material comprises lithium iron phosphate in an amount of about 20 wt% to about 70 wt%.
[0143] J. The composition of Paragraph G or Paragraph H, wherein the lithium-ion battery cathode material comprises nickel cobalt aluminum oxide in an amount of about 40 wt% to about 80 wt%.
[0144] K. The composition of Paragraph E or Paragraph F, wherein the conductive material comprises a lithium-ion battery anode material.
[0145] L. The composition of Paragraph K, wherein the lithium-ion battery anode material comprises graphite, lithium, silicon, or a combination of any two or more thereof.
[0146] M. The composition of any one of Paragraphs A-L, comprising about 40 wt% to about 60 wt% solvent and about 0.05 wt% to about 5 wt% 3 -amino-2 -butanol.
[0147] N. The composition of any one of Paragraphs A-M, comprising about 0.1 wt% to about 3 wt% 3 -amino-2 -butanol.
[0148] O. The composition of any one of Paragraphs E-N, wherein the conductive material comprises a conductive carbon.
[0149] P. The composition of Paragraph O, comprising about 80 wt% to about 98 wt% solvent and about 0.5 wt% to about 10 wt% 3-amino-2-butanol.
[0150] Q. The composition of Paragraph O or Paragraph P, wherein the conductive carbon material comprises single walled carbon nanotubes, multi-walled carbon nanotubes, carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, graphene, or a combination of any two or more thereof.
[0151] R. The composition of any one of Paragraphs A-Q, further comprising a lithium-ion battery separator polymer. S. The composition of Paragraph R, wherein the lithium-ion battery separator polymer comprises polyethylene, polypropylene, poly(vinylidene fluoride), polyamide, polyethylene oxide, or any combination or copolymer of any two or more thereof.
[0152] T. The composition of any one of Paragraphs A-S, further comprising an amino alcohol other than 3 -amino-2 -butanol (an “other amino alcohol”).
[0153] U. The composition of Paragraph T, wherein the other amino alcohol is 3-amino-3-methyl-2- butanol, 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)-3- methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof.
[0154] V. The composition of Paragraph T or Paragraph U, wherein the composition comprises about 0.01 wt% to about 5 wt% of the other amino alcohol.
[0155] W. The composition of any one of Paragraphs T-V, wherein the other amino alcohol compri ses 3 -(ethylamino)-butan-2-ol .
[0156] X. A method of making a composition of any one of Paragraph A-W, the method comprising combining 3-amino-2-butanol with a purity of at least 95 wt% with sufficient nonaqueous solvent to provide the composition.
[0157] Y. The method of Paragraph X, wherein the method further comprises mixing the combined
[0158] 3 -amino-2 -butanol and non-aqueous solvent until a homogenous solution is obtained.
[0159] Z. A lithium-ion battery electrode slurry comprising a conductive material, a solvent, and 3- amino-2-butanol, optionally wherein the lithium-ion battery electrode slurry exhibits a biobased content of the 3 -amino-2 -butanol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
[0160] AA. The lithium-ion battery electrode slurry of Paragraph Z, comprising about 40 wt% to about 99 wt% solvent and about 0.01 wt% to about 10 wt% 3 -amino-2 -butanol. AB. The lithium-ion battery electrode slurry of Paragraph Z, comprising about 40 wt% to about 60 wt% solvent and about 0.05 wt% to about 5 wt% 3 -amino-2 -butanol.
[0161] AC. The lithium-ion battery electrode slurry of Paragraph Z, comprising about 0.1 wt% to about 3 wt% 3 -amino-2 -butanol.
[0162] AD. The lithium-ion battery electrode slurry of any one of Paragraphs Z-AC, comprising about 5 wt% to about 90 wt% conductive material.
[0163] AE. The lithium-ion battery electrode slurry of any one of Paragraphs A- AD, wherein the conductive material comprises a lithium-ion battery cathode material.
[0164] AF. The lithium-ion battery electrode slurry of Paragraph AE, wherein the lithium-ion battery cathode material comprises lithium iron phosphate, lithium manganese iron phosphate, lithium nickel manganese cobalt oxide, lithium cobalt oxide, lithium nickel oxide, lithium manganese oxide, lithium nickel cobalt aluminum oxide, lithium titanate, or a combination of any two or more thereof.
[0165] AG. The lithium-ion battery electrode slurry of Paragraph AF, wherein the lithium-ion battery cathode material comprises lithium iron phosphate in an amount of about 20 wt% to about 70 wt%.
[0166] AH. The lithium-ion battery electrode slurry of Paragraph AF, wherein the lithium-ion battery cathode material comprises nickel cobalt aluminum oxide in an amount of about 40 wt% to about 80 wt%.
[0167] Al. The lithium-ion battery electrode slurry of any one of Paragraphs Z-AD, wherein the conductive material comprises a lithium-ion battery anode material.
[0168] AJ. The lithium-ion battery electrode slurry of Paragraph Al, wherein the lithium-ion battery anode material comprises graphite, lithium metal, silicon, or a combination of any two or more thereof.
[0169] AK. The lithium-ion battery electrode slurry of any one of Paragraphs Z-AJ, further comprising a polymeric binder. AL. The lithium-ion battery electrode slurry of Paragraph AK, wherein the polymeric binder comprises polyvinylidene fluoride, styrene-butadiene copolymer, carboxymethyl cellulose, polyacrylate latex or a mixture of any two or more thereof.
[0170] AM. The lithium-ion battery electrode slurry of Paragraph AL, wherein the polymeric binder is styrene-butadiene copolymer or carboxymethyl cellulose.
[0171] AN. The lithium-ion battery electrode slurry of any one of Paragraphs Z-AM, further comprising a conductive carbon.
[0172] AO. The lithium-ion battery electrode slurry of Paragraph AN, wherein the conductive carbon material comprises single walled carbon nanotubes, multi-walled carbon nanotubes, carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, graphene, or a combination of any two or more thereof.
[0173] AP. The lithium-ion battery electrode slurry of any one of Paragraphs Z-AO, wherein the solvent comprises N-methyl-2-pyrrolidone or water.
[0174] AQ. A method of making a lithium-ion battery electrode slurry of any one of Paragraphs Y-
[0175] AO, the method comprising combining 3 -amino-2 -butanol with a purity of at least 95 wt% with sufficient solvent and sufficient conductive material to provide the composition.
[0176] AR. The method of Paragraph AQ, wherein the method further comprises mixing the combined 3-amino-2-butanol, the conductive material, and the solvent until a homogenous slurry is obtained.
[0177] AS. A composition comprising: about 5 wt% to about 30 wt% of a polymer comprising polyethylene, polypropylene, poly(vinylidene fluoride), polyamide, polyethylene oxide, polypropylene oxide, or any combination or copolymer of any two or more thereof; about 0.01 wt% to about 10 wt% 3-amino-2-butanol; and a solvent; optionally wherein the composition exhibits a biobased content of the 3-amino-2- butanol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
[0178] AT. The composition of Paragraph AS, wherein the polymer comprises a copolymer of polyethylene oxide and polypropylene oxide.
[0179] AU. The composition of Paragraph AS or Paragraph AT, wherein the solvent comprises N- methyl-2-pyrrolidone.
[0180] AV. A method of making the composition of any one of Paragraphs AS to AU, the method comprising combining 3 -amino-2 -butanol with a purity of at least 95 wt% with sufficient polymer and sufficient solvent to provide the composition.
[0181] AW. The method of Paragraph AV, wherein the method further comprises mixing the combined 3-amino-2-butanol, the polymer, and the solvent until a homogenous solution is obtained.
[0182] AX. A composition comprising conductive carbon, a solvent, and 3-amino-2-butanol, optionally wherein the composition exhibits a biobased content of the 3-amino-2- butanol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
[0183] AY. The composition of Paragraph AX, wherein the conductive carbon comprises single walled carbon nanotubes, multi-walled carbon nanotubes, carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, graphene, or a combination of any two or more thereof.
[0184] AZ. The composition of Paragraph AX or Paragraph AY, comprising 0.2 wt% to 20 wt% conductive carbon and about 0.2 wt.% to about 20 wt.% 3-amino-2-butanol.
[0185] BA. A composition comprising: about 0.001 wt% to about 40 wt% of 3-amino-2-butanol; and about 10 wt% to about 99 wt% glycol ether; optionally wherein the composition exhibits a biobased content of the 3-amino-2- butanol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
[0186] BB. The composition of Paragraph BA, wherein the glycol ether comprises butyldiglycol, 2-
[0187] (2-ethoxyethoxy)ethanol, or a combination thereof.
[0188] BC. The composition of Paragraph BA or Paragraph BB, further comprising about 2 wt% to about 40 wt% of N-methyl pyrrolidone.
[0189] BD. The composition of any one of Paragraphs BA to BC, further comprising about 2 wt% to about 60 wt% water.
[0190] BE. A composition comprising: about 0.001 wt% to about 40 wt% of 3-amino-2-butanol; about 5 wt% to about 40 wt% oxidizer; and about 50 wt% to about 90 wt% water: optionally wherein the composition exhibits a biobased content of the 3-amino-2- butanol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
[0191] BF. The composition of Paragraph BE, wherein the oxidizing agent comprises hydrogen peroxide or a peroxy acid.
[0192] BG. The composition of Paragraph BE, further comprising about 2 wt% to about 40 wt% of oxalic acid.
[0193] BH. The composition of any one of Paragraphs BE to BG, further comprising about 0.01 wt% to about 1 wt% benzotri azole.
[0194] BI. The composition of any one of Paragraphs BE to BH, wherein the composition has a pH of about 4 to about 5.
[0195] BJ. A composition comprising: about 0.001 wt% to about 40 wt% of 3-amino-2-butanol; about 1 wt% to about 40 wt% of a quaternary ammonium salt; and about 50 wt% to about 95 wt% water; optionally wherein the composition exhibits a biobased content of the 3-amino-2- butanol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
[0196] BK. The composition of Paragraph BJ, wherein the quaternary ammonium salt comprises tetramethylammonium hydroxide.
[0197] BL. The composition of Paragraph BJ or Paragraph BK, further comprising about 0.01 wt% to about 1 wt% benzotri azole.
[0198] BM. The composition of any one of Paragraphs BJ to BL, further comprising about 0.01 wt% to about 1 wt% gallic acid.
[0199] BN. The composition of any one of Paragraphs BJ to BM, further comprising about 0.05 wt% to about 2 wt% dodecylbenzene sulfonic acid.
[0200] BO. The composition of any one of Paragraphs BJ to BN, wherein the composition has a pH of about 9 to about 10.
[0201] BP. The composition of any one of Paragraphs BJ to BO, wherein the composition has total metals of about 3 ppb to about 100 ppb.
[0202] BQ. The composition of any one of Paragraphs BJ to BP, further comprising an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”).
[0203] BR. The composition of Paragraph BQ, wherein the other amino alcohol is 3-amino-3- methyl-2-butanol, 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)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof.
[0204] BS. The composition of Paragraph BQ or Paragraph BR, wherein the composition comprises about 0.01 wt% to about 5 wt% of the other amino alcohol. BT. The composition of any one of Paragraphs BQ to BS, wherein the other amino alcohol compri ses 3 -(ethylamino)-butan-2-ol .
[0205] BU. The composition of any one of Paragraphs BJ to BT, comprising about 0.001 wt% to about 2 wt% 3 -amino-2 -butanol.
[0206] BV. The composition of any one of Paragraphs BJ to BU, comprising about 0.01 wt% to about 1 wt% 3 -amino-2 -butanol.
[0207] BW. The composition of any one of Paragraphs BJ to BV, comprising about 0.03 wt% to about 0.5 wt% 3-amino-2-butanol.
[0208] BX. The composition of any one of Paragraphs BJ to BW, comprising about 0.05 wt% to about 0.3 wt% 3-amino-2-butanol.
[0209] BY. A composition comprising about 0.001 wt% to about 40 wt% of 3-amino-2-butanol; about 5 wt% to about 40 wt% hydroxylamine; and about 50 wt% to about 90 wt% water, optionally wherein the composition exhibits a biobased content of the 3-amino- 2-butanol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
[0210] BZ. A composition for use in electrical and electronic applications, the composition comprising about 30 wt% to about 99.99 wt% 3-amino-2-butanol; about 0.01 wt% to about 70 wt% water; and optionally an amino alcohol other than 3 -amino-2 -butanol (an “other amino alcohol”).
[0211] CA. The composition for use of Paragraph BZ, wherein the composition is for use in transparent conductors and sensors, semiconductor films for sensors, photovoltaics, for use in lithium-ion batteries, battery manufacturing, semiconductor materials and devices, the manufacture of semiconductor materials and devices as a cleaning formulation, and / or preparing semiconductor devices (such as diodes, transistors, integrated circuits, photonic devices, memory devices, and / or sensors). CB. The composition for use of Paragraph BZ or Paragraph CA, the composition comprising about 0.01 wt% to about 60 wt% of the other amino alcohol.
[0212] CC. The composition for use of Paragraph CB, comprising not more than 1 wt% of the other amino alcohol.
[0213] CD. The composition for use of any one of Paragraphs BZ-CC, comprising about 85 wt% to about 95 wt% 3-amino-2-butanol and about 5 wt% to about 15 wt% water.
[0214] CE. The composition for use of any one of Paragraphs BZ-CD, comprising about 90 wt% 3- amino-2-butanol, about 10 wt% water, and less than 1 wt% of the other amino alcohol.
[0215] CF. The composition for use of any one of Paragraphs BZ-CE, wherein the composition comprises less than 2 wt% secondary amine.
[0216] CG. The composition for use of any one of Paragraphs BZ-CF, wherein the composition further comprises not more than 5 wt% of the other amino alcohol.
[0217] CH. The composition for use of any one of Paragraphs BZ-CG, wherein the other amino alcohol is 3-amino-3-methyl-2-butanol, 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)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof.
[0218] CI. The composition for use of any one of Paragraphs BZ-CH, wherein the composition comprises at least about 0.01 wt% of the other amino alcohol.
[0219] CJ. The composition for use of any one of Paragraphs BZ-CI, wherein the composition comprises 3-(ethylamino)-butan-2-ol in addition to 3-amino-2-butanol.
[0220] CK. The composition for use of any one of Paragraphs BZ-CJ, wherein the composition exhibits a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
[0105] Other embodiments are set forth in the following claims, along with the full scope of equivalents to which such claims are entitled.
Claims
ClaimsWHAT IS CLAIMED IS:
1. A composition comprising a solvent and 3-amino-2-butanol in a weight ratio of 300: 1 to about 1:300, optionally wherein the solvent is a non-aqueous solvent.
2. The composition of Claim 1, comprising the solvent and 3 -amino-2 -butanol in a weight ratio of 2: 1 to about 1 :2.
3. The composition of Claim 1, wherein the solvent is a non-aqueous solvent that comprises methyl isobutyl ketone, ethyl propyl ketone, acetophenone, dimethylformamide, N- methyl-2-pyrrolidone (NMP), acetonitrile, dimethyl sulfoxide, or a combination of two or more thereof.
4. The composition of Claim 1, comprising about 40 wt% to about 99 wt% solvent and about0.01 wt% to about 10 wt% 3-amino-2-butanol.
5. The composition of Claim 1, further comprising a conductive material, a semiconductor material, or a combination thereof.
6. The composition of Claim 5, comprising about 5 wt% to about 90 wt% conductive material.
7. The composition of Claim 5, wherein the conductive material comprises a lithium-ion battery cathode material.
8. The composition of Claim 7, wherein the lithium-ion battery cathode material comprises lithium iron phosphate, lithium manganese iron phosphate, lithium nickel manganese cobalt oxide, lithium cobalt oxide, lithium nickel oxide, lithium manganese oxide, lithium nickel cobalt aluminum oxide, lithium titanate, or a combination of any two or more thereof.
9. The composition of Claim 7, wherein the lithium-ion battery cathode material comprises lithium iron phosphate in an amount of about 20 wt% to about 70 wt%.
10. The composition of Claim 7, wherein the lithium-ion battery cathode material comprises nickel cobalt aluminum oxide in an amount of about 40 wt% to about 80 wt%.
11. The composition of Claim 5, wherein the conductive material comprises a lithium-ion battery anode material.
12. The composition of Claim 11, wherein the lithium-ion battery anode material comprises graphite, lithium, silicon, or a combination of any two or more thereof.
13. The composition of Claim 1, comprising about 40 wt% to about 60 wt% solvent and about 0.05 wt% to about 5 wt% 3-amino-2-butanol.
14. The composition of Claim 1, comprising about 0.1 wt% to about 3 wt% 3-amino-2- butanol.
15. The composition of Claim 5, wherein the conductive material comprises a conductive carbon.
16. The composition of Claim 15, comprising about 80 wt% to about 98 wt% solvent and about 0.5 wt% to about 10 wt% 3-amino-2-butanol.
17. The composition of Claim 15, wherein the conductive carbon comprises single walled carbon nanotubes, multi-walled carbon nanotubes, carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, graphene, or a combination of any two or more thereof.
18. The composition of Claim 1, further comprising a lithium-ion battery separator polymer.
19. The composition of Claim 18, wherein the lithium-ion battery separator polymer comprises polyethylene, polypropylene, poly(vinylidene fluoride), polyamide, polyethylene oxide, or any combination or copolymer of any two or more thereof.
20. The composition of Claim 1, further comprising an amino alcohol other than 3-amino-2- butanol (an “other amino alcohol”).
21. The composition of Claim 20, wherein the other amino alcohol is 3-amino-3-methyl-2- butanol, 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)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof.
22. The composition of Claim 20, wherein the composition comprises about 0.01 wt% to about 5 wt% of the other amino alcohol.
23. The composition of Claim 20, wherein the other amino alcohol comprises 3-(ethylamino)-butan-2-ol.
24. A method of making a composition of Claim 1, the method comprising combining 3- amino-2-butanol with a purity of at least 95 wt% with sufficient solvent to provide the composition.
25. The method of Claim 24, wherein the method further comprises mixing the combined 3- amino-2-butanol and solvent until a homogenous solution is obtained.
26. A lithium-ion battery electrode slurry comprising a conductive material, a solvent, and 3- amino-2-butanol.
27. The lithium-ion battery electrode slurry of Claim 26, comprising about 40 wt% to about99 wt% solvent and about 0.01 wt% to about 10 wt% 3-amino-2-butanol.
28. The lithium-ion battery electrode slurry of Claim 26, comprising about 40 wt% to about60 wt% solvent and about 0.05 wt% to about 5 wt% 3-amino-2-butanol.
29. The lithium-ion battery electrode slurry of Claim 26, comprising about 0.1 wt% to about3 wt% 3-amino-2-butanol.
30. The lithium-ion battery electrode slurry of Claim 26, comprising about 5 wt% to about90 wt% conductive material.
31. The lithium-ion battery electrode slurry of Claim 26, wherein the conductive material comprises a lithium-ion battery cathode material.
32. The lithium-ion battery electrode slurry of Claim 31, wherein the lithium-ion battery cathode material comprises lithium iron phosphate, lithium manganese ironphosphate, lithium nickel manganese cobalt oxide, lithium cobalt oxide, lithium nickel oxide, lithium manganese oxide, lithium nickel cobalt aluminum oxide, lithium titanate, or a combination of any two or more thereof.
33. The lithium-ion battery electrode slurry of Claim 32, wherein the lithium-ion battery cathode material comprises lithium iron phosphate in an amount of about 20 wt% to about 70 wt%.
34. The lithium-ion battery electrode slurry of Claim 32, wherein the lithium-ion battery cathode material comprises nickel cobalt aluminum oxide in an amount of about 40 wt% to about 80 wt%.
35. The lithium-ion battery electrode slurry of Claim 26, wherein the conductive material comprises a lithium-ion battery anode material.
36. The lithium-ion battery electrode slurry of Claim 35, wherein the lithium-ion battery anode material comprises graphite, lithium metal, silicon, or a combination of any two or more thereof.
37. The lithium-ion battery electrode slurry of Claim 26, further comprising a polymeric binder.
38. The lithium-ion battery electrode slurry of Claim 37, wherein the polymeric binder comprises polyvinylidene fluoride, styrene-butadiene copolymer, carboxymethyl cellulose, polyacrylate latex or a mixture of any two or more thereof.
39. The lithium-ion battery electrode slurry of Claim 38, wherein the polymeric binder is styrene-butadiene copolymer or carboxymethyl cellulose.
40. The lithium-ion battery electrode slurry of Claim 26, further comprising a conductive carbon.
41. The lithium-ion battery electrode slurry of Claim 40, wherein the conductive carbon material comprises single walled carbon nanotubes, multi-walled carbon nanotubes,carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, graphene, or a combination of any two or more thereof.
42. The lithium-ion battery electrode slurry of Claim 26, wherein the solvent comprises N- methyl-2-pyrrolidone or water.
43. A method of making a lithium-ion battery electrode slurry of Claim 26, the method comprising combining 3 -amino-2 -butanol with a purity of at least 95 wt% with sufficient solvent and sufficient conductive material to provide the composition.
44. The method of Claim 43, wherein the method further comprises mixing the combined 3- amino-2-butanol, the conductive material, and the solvent until a homogenous slurry is obtained.
45. A composition comprising: about 5 wt% to about 30 wt% of a polymer comprising polyethylene, polypropylene, poly(vinylidene fluoride), polyamide, polyethylene oxide, polypropylene oxide, or any combination or copolymer of any two or more thereof; about 0.01 wt% to about 10 wt% 3-amino-2-butanol; and a solvent.
46. The composition of Claim 45, wherein the polymer comprises a copolymer of polyethylene oxide and polypropylene oxide.
47. The composition of Claim 45, wherein the solvent comprises N-methyl-2-pyrrolidone.
48. A method of making the composition of Claim 45, the method comprising combining 3- amino-2-butanol with a purity of at least 95 wt% with sufficient polymer and sufficient solvent to provide the composition.
49. The method of Claim 48, wherein the method further comprises mixing the combined 3- amino-2-butanol, the polymer, and the solvent until a homogenous solution is obtained.
50. A composition comprising conductive carbon, a solvent, and 3 -amino-2 -butanol.
51. The composition of Claim 50, wherein the conductive carbon comprises single walled carbon nanotubes, multi-walled carbon nanotubes, carbon black, amorphous carbon, mesoporous carbon, carbon nanofiber, graphite, graphene, or a combination of any two or more thereof.
52. The composition of Claim 50, comprising 0.2 wt% to 20 wt% conductive carbon and about 0.2 wt.% to about 20 wt.% 3-amino-2-butanol.
53. A composition comprising: about 0.001 wt% to about 40 wt% of 3-amino-2-butanol; and about 10 wt% to about 99 wt% glycol ether.
54. The composition of Claim 53, wherein the glycol ether comprises butyldiglycol, 2-(2- ethoxyethoxy)ethanol, or a combination thereof.
55. The composition of Claim 53, further comprising about 2 wt% to about 40 wt% of N- methyl pyrrolidone.
56. The composition of Claim 53, further comprising about 2 wt% to about 60 wt% water.
57. A composition comprising: about 0.001 wt% to about 40 wt% of 3-amino-2-butanol; about 5 wt% to about 40 wt% oxidizing agent; and about 50 wt% to about 90 wt% water.
58. The composition of Claim 57, wherein the oxidizing agent comprises hydrogen peroxide or a peroxy acid.
59. The composition of Claim 57, further comprising about 2 wt% to about 40 wt% of oxalic acid.
60. The composition of Claim 57, further comprising about 0.01 wt% to about 1 wt% benzotri azole.
61. The composition of Claim 57, wherein the composition has a pH of about 4 to about 5.
62. A composition comprising: about 0.001 wt% to about 40 wt% of 3-amino-2-butanol; about 1 wt% to about 40 wt% of a quaternary ammonium salt; and about 50 wt% to about 95 wt% water.
63. The composition of Claim 62, wherein the quaternary ammonium salt comprises tetramethylammonium hydroxide.
64. The composition of Claim 62, further comprising about 0.01 wt% to about 1 wt% benzotri azole.
65. The composition of Claim 62, further comprising about 0.01 wt% to about 1 wt% gallic acid.
66. The composition of Claim 62, further comprising about 0.05 wt% to about 2 wt% dodecylbenzene sulfonic acid.
67. The composition of Claim 62, wherein the composition has a pH of about 9 to about 10.
68. The composition of Claim 53, wherein the composition has total metals of about 3 ppb to about 100 ppb.
69. The composition of Claim 53, further comprising an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”).
70. The composition of Claim 69, wherein the other amino alcohol is 3-amino-3-methyl-2- butanol, 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)-3- methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof.
71. The composition of Claim 69, wherein the composition comprises about 0.01 wt% to about 5 wt% of the other amino alcohol.
72. The composition of Claim 69, wherein the other amino alcohol comprises 3-(ethylamino)-butan-2-ol.
73. The composition of Claim 53, comprising about 0.001 wt% to about 2 wt% 3-amino-2- butanol.
74. The composition of Claim 53, comprising about 0.01 wt% to about 1 wt% 3-amino-2- butanol.
75. The composition of Claim 53, comprising about 0.03 wt% to about 0.5 wt% 3-amino-2- butanol.
76. The composition of Claim 53, comprising about 0.05 wt% to about 0.3 wt% 3-amino-2- butanol.
77. A composition comprising: about 0.001 wt% to about 40 wt% of 3-amino-2-butanol; about 5 wt% to about 40 wt% hydroxylamine; and about 50 wt% to about 90 wt% water.
78. A composition for use in electrical and electronic applications, the composition comprising about 30 wt% to about 99.99 wt% 3-amino-2-butanol; about 0.01 wt% to about 70 wt% water; and optionally an amino alcohol other than 3 -amino-2 -butanol (an “other amino alcohol”).
79. The composition for use of Claim 78, wherein the composition is for use in transparent conductors and sensors, semiconductor films for sensors, photovoltaics, for use in lithium-ion batteries, battery manufacturing, semiconductor materials and devices, the manufacture of semiconductor materials and devices as a cleaning formulation, and / or preparing semiconductor devices.
80. The composition for use of Claim 78, the composition comprising about 0.01 wt% to about 60 wt% of the other amino alcohol.
81. The composition for use of Claim 80, comprising not more than 1 wt% of the other amino alcohol.
82. The composition for use of Claim 78, comprising about 70 wt% to about 95 wt% 3- amino-2-butanol and about 5 wt% to about 30 wt% water.
83. The composition for use of Claim 78, comprising about 90 wt% 3 -amino-2 -butanol, about 10 wt% water, and less than 1 wt% of the other amino alcohol.
84. The composition for use of Claim 78, wherein the composition comprises less than 2 wt% secondary amine.
85. The composition for use of Claim 78, wherein the composition further comprises not more than 5 wt% of the other amino alcohol.
86. The composition for use of Claim 85, wherein the other amino alcohol is 3-amino-3- methyl-2-butanol, 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)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol,or a combination of any two or more thereof.
87. The composition for use of Claim 85, wherein the composition comprises at least about0.01 wt% of the other amino alcohol.
88. The composition for use of Claim 85, wherein the composition comprises 3-(ethylamino)-butan-2-ol in addition to 3-amino-2-butanol.
89. The composition for use of Claim 78, wherein the composition exhibits a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
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