Personal care formulations comprising 3-amino-3-methyl-2-butanol and use thereof
Patent Information
- Authority / Receiving Office
- EP · EP
- Patent Type
- Applications
- Current Assignee / Owner
- ADVANCION CORP
- Filing Date
- 2024-09-16
- Publication Date
- 2026-07-01
AI Technical Summary
Current personal care products, such as hair styling agents and sanitizing agents, rely on non-renewable petroleum-based raw materials, leading to environmental degradation and performance issues with renewable alternatives.
The use of 3-amino-3-methyl-2-butanol (AMB) in personal care formulations, which is a renewable, biobased compound that provides improved sustainability, low toxicity, and comparable or superior performance to petroleum-based alternatives.
AMB compositions offer high-performance, cost-effective solutions for personal care products, with enhanced curl retention, improved clarity in hand sanitizers, and superior SPF ratings in sunscreens, while reducing environmental impact.
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Figure US2024046917_03042025_PF_FP_ABST
Abstract
Description
[0001] Atty. Dkt. No.: 109691-0767 PERSONAL CARE FORMULATIONS COMPRISING 3-AMINO-3- METHYL-2-BUTANOL AND USE THEREOF CROSS-REFERENCE TO RELATED APPLICATIONS [1] This application claims the benefit of and priority to U.S. Provisional Appl. No. 63 / 540,850, filed September 27, 2023, which is incorporated herein by reference in its entirety for any and all purposes. TECHNICAL FIELD [2] The present technology relates generally to formulations comprising 3-amino-3- methyl-2-butanol for personal care products, hair styling, creams, lotions, sunscreens and the like. BACKGROUND [3] Many commonly used products including hair styling aerosols, non-aerosol (e.g., pump) sprays, hair styling gels, and hand sanitizers, among others, are made of compositions using chemicals typically derived from non-renewable raw materials such as petroleum. For example, hair styling aerosols, hair styling gels, and hand sanitizers incorporate many chemicals that are derived from petroleum, including neutralizing agents meant to partially or completely neutralize acid groups present in other chemicals in the composition. [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. [5] Thus, as explained above and in more details below, there remains a need for compositions for commonly used products such as hair styling agents and sanitizing agents made with natural, renewable starting materials that offer equivalent or better performance to current products. -1- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 SUMMARY [6] The present disclosure is directed to compositions and formulations comprising 3- amino-3-methyl-2-butanol (also known as 3-amino-3-methylbutan-2-ol; CAS No.: 13325-14- 9) for personal care formulations. 3-Amino-3-methyl-2-butanol has several advantages, including its improved sustainability profile, demonstrated by its ability to be manufactured as a renewable, biobased compound (i.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., NH3). Thus, the presently disclosed technology overcomes common adoption barriers associated with renewable personal care chemicals, such as poor performance and high cost, instead providing a high-performance, cost-effective solution with the potential for incorporating bio-based carbon. [7] In one aspect, the present technology provides compositions for personal care products comprising 3-amino-3-methyl-2-butanol. In some embodiments, the composition may be an aqueous based solution. For example, the composition may be an aqueous solution, mixture, dispersion, or emulsion. In some embodiments, the composition may include a molecule comprising an acid group, which may be a small molecule or a polymer comprising an acid group, and an amount of 3-amino-3-methyl-2-butanol effective to partially or completely neutralize the acid group. In some embodiments, the composition may include about 0.005 wt% to about 10 wt% of the 3-amino-3-methyl-2-butanol. The composition may include a mixture of alcohol and water. BRIEF DESCRIPTION OF THE DRAWINGS [8] FIG.1 provides the percent curl retention over time using Dow Hair Styling Resin with various neutralizing agents (triisopropanolamine (aka, 1,1′,1′′-nitrilotri(propan-2-ol)), 3- amino-3-methyl-2-butanol (AMB), triethanolamine, and 2-amino-2-methyl-1-propanol (AMP) in hair styling aerosols. FIG.1 indicates that the hair styling aerosol with AMB performed similarly to that with AMP and significantly better than those with triethanolamine (TEA) and triisopropanolamine (TIPA) to retain curls over time. -2- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 [9] FIG.2 demonstrates high humidity curl retention over time using Dow Hair Styling Resin with various neutralizing agents AMP, AMB, and triethanolamine, in hair styling gels. FIG.2 indicated that the hair styling gel with AMB performed similarly to that with AMP and significantly better than that with TEA.
[0010] FIGS.3A and 3B provide a comparison of the effects on hand sanitizer clarity by using varying amounts of thickening agent (i.e., Carbopol 980 at 0.25 wt% (FIG.3A) and 0.45 wt% (FIG.3B)) and different neutralizing agents (e.g., AMB and TEA). FIGS.3A and 3B indicated that hand sanitizers comprising AMB provided similar clarity to hand sanitizers comprising AMP and significantly better clarity than hand sanitizers comprising TEA.
[0011] FIG.4 is a bar graph showing the effect of dispersant (Tris-amino, AMP, AMB, TEA, NaOH) on SPF of various sunscreen formulations. The AMB-containing formulation provided the highest SPF rating of the formulations tested. DETAILED DESCRIPTION
[0012] The following terms are used throughout as defined below.
[0013] As used herein and in the appended claims, singular articles such as “a” and “an” and “the” and similar referents in the context of describing the elements (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. Recitation of ranges of values herein are merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or exemplary language (e.g., “such as”) provided herein, is intended merely to better illuminate the embodiments and does not pose a limitation on the scope of the claims unless otherwise stated. No language in the specification should be construed as indicating any non-claimed element as essential. -3- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767
[0014] As used herein, “about” will be understood by persons of ordinary skill in the art and will vary to some extent depending upon the context in which it is used. If there are uses of the term which are not clear to persons of ordinary skill in the art, given the context in which it is used, “about” will mean up to plus or minus 10% of the particular term – for example, “about 10 wt%” would be understood to mean “9 wt% to 11 wt%.” It is to be understood that when “about” precedes a term, the term is to be construed as disclosing “about” the term as well as the term without modification by “about” – for example, “about 10 wt%” discloses “9 wt% to 11 wt%” as well as disclosing “10 wt%.”
[0015] The phrase “and / or” as used in the present disclosure will be understood to mean any one of the recited members individually or a combination of any two or more thereof – for example, “A, B, and / or C” would mean “A or B or C; A and B; A and C; B and C; or the combination of A, B, and C.”
[0016] The term "alkyl" refers to a group, whether alone or as part of another group (e.g., in dialkylamino), encompasses straight and branched chain aliphatic groups (i.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.
[0017] The term "alkoxy" refers to a group in which an oxygen attached to a saturated straight or branched chain alkyl group. Unless otherwise indicated, the alkoxy group contains 1 to 6 carbon atoms (e.g. methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso- butoxy, sec-butoxy, tert-butoxy, n-pentoxy, neopentyloxy, iso-pentyloxy, n-hexyloxy or iso- hexyloxy), and in any embodiments, 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.
[0018] Groups described herein having two or more points of attachment (i.e., divalent, trivalent, or polyvalent) within the compound of the present technology are designated by use -4- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 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.
[0019] In general, “substituted” refers to an alkyl group, as defined above in which one or more bonds to a hydrogen atom contained therein are replaced by a bond to non-hydrogen or non-carbon atoms. Substituted groups also include groups in which one or more bonds to a carbon(s) or hydrogen(s) atom are replaced by one or more bonds, including double or triple bonds, to a heteroatom. In some embodiments, a substituted group is substituted with 1, 2, or 3 substituents. Examples of substituent groups include, but are not limited to, hydroxyl, amino, thiol, nitro, halo, ester, amido, carbonyl, or carboxylic acid. Unless otherwise indicated, the foregoing substituent groups are not themselves further substituted.
[0020] Unless stated otherwise, all the molecular weight (i.e., molar mass) data, number- average 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).
[0021] As used herein, “fixative” refers to the film forming component of a product. To form the films, the polymeric fixative (i.e., polymer) may be coalesced. Coalescence refers to the process where first the solvent (e.g., water and / or an alcohol such as ethanol) evaporates causing the polymeric fixative to be drawn together and then fused into irreversibly bound networked structures, so that the product cannot redissolve in the original carrier solvent. Polymeric fixative resin is also referred to as “fixative” and “polymeric fixative.”
[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. -5- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 3-Amino-3-methyl-2-butanol (“AMB”) Compositions
[0023] In an aspect, the present technology provides a composition for use in personal care applications, such as for use in hair styling aerosols, body lotions, mascara, hair colorants, sunscreens, hand sanitizers, cleansers, eye creams, exfoliants, shampoos, conditioners, hair masks, hair styling gels, hair styling mousse, dry shampoos, non-aerosol hair styling sprays, body washes, soaps, body scrubs, body butters, lipsticks, foundations, eye shadows, concealers, blushes, eyeliners, brow gels, lip glosses, lip balms, setting sprays, and / or shaving creams, where the composition includes about 30 wt% to about 99.99 wt% 3-amino-3- methyl-2-butanol, about 0.01 wt% to about 70 wt% water, and optionally an amino alcohol other than 3-amino-3-methyl-2-butanol (an “other amino alcohol”). In any embodiments, the compositions may include 3-amino-3-methyl-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-3- methyl-2-butanol. In any embodiments, the compositions may include at least about 90 wt% 3-amino-3-methyl-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 deionized, distilled or reverse osmosis (R.O.) water, or any combination thereof, including, -6- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 e.g., double distilled. In any embodiment herein, the purity and water content may be adjusted depending on the desired physical properties and end-use application.
[0025] In any embodiment herein, water and / or an other amino alcohol may be included in the compositions including 3-amino-3-methyl-2-butanol, e.g., to improve handling and / or modify performance characteristics. For example, addition of water to the compositions including 3-amino-3-methyl-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, 2- aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino- 1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-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., 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3- (ethylamino)-3-methylbutan-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%, or 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., 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2- methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3- methylbutan-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 -7- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 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.
[0026] In any embodiment herein, the composition may include less than about 2 wt% secondary amine (e.g., 3-(ethylamino)-3-methylbutan-2-ol, 2-(butylamino)ethanol, diethanolamine, diisopropanolamine (also referred to as 1-(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.
[0027] In any embodiment herein, the composition may exhibit a biobased content of the 3- amino-3-methyl-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-3-methyl-2-butanol in compositions of the present technology may be provided by using purely petroleum-based 3-amino-3-methyl-2-butanol (i.e., with 0% biobased content), using 3-amino-3-methyl-2-butanol produced in part with biobased starting materials, using combinations of purely petroleum-based 3-amino-3-methyl-2-butanol and 3-amino-3-methyl- 2-butanol produced in part or in whole with biobased starting materials, or¾for a biobased content of the 3-amino-3-methyl-2-butanol of 100%¾using 3-amino-3-methyl-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-3-methyl-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-3-methyl-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 10%, or may exhibit a -8- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 biobased content of the 3-amino-3-methyl-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 (i.e., 3-amino-3-methyl-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., NH3). Personal Care Products Comprising 3-Amino-3-methyl-2-butanol
[0028] In one aspect, the present technology provides compositions comprising 3-amino-3- methyl-2-butanol for use in personal care products. The composition may be a liquid, cream, scrub, bar, solution, emulsion, dispersion, slurry, gel, foam, mousse, or paste. Without being bound by any theory, incorporating 3-amino-3-methyl-2-butanol into personal care formulations may enhances the performance, rheology, and stability of a wide range of products. The 3-amino-3-methyl-2-butanol may be used to adjust pH, rheology, viscosity, emulsification, and / or product stabilization of the composition. In some embodiments, 3- amino-3-methyl-2-butanol may replace in part or in whole pH adjusters typically used in personal care products (e.g., monoethanolamine (MEA), ammonia, and triethanolamine). In some embodiments, the 3-amino-3-methyl-2-butanol may provide control of body odor and / or sweat odor.
[0029] The compositions of the present technology may be used as skincare products (e.g., cleansers, moisturizers, eye creams, exfoliants, sunscreens), hair care products (e.g., shampoos, conditioners, hair masks, hair styling gel, styling mousse, dry shampoos, hair styling aerosols, non-aerosol hair styling sprays, hair color products), body care products (e.g., body washes, soaps, body scrubs, body lotions, body butters, sunscreens), and / or makeups (e.g., color cosmetics, lipsticks, brow gel, foundation, eye shadow, concealer, blush, eyeliner, mascara, lip gloss, lip balm, setting spray). and / or personal hygiene products (e.g., shaving creams and hand sanitizers).
[0030] Compositions of the present technology may include a wide range of amounts of the 3-amino-3-methyl-2-butanol described herein. For example, the compositions may include about 0.005 wt% to about 10 wt% of 3-amino-3-methyl-2-butanol based on the total weight -9- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 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 0.02 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 0.4 wt% to about 3 wt%, about 0.2 wt% to about 2 wt%, about 0.1 wt% to about 1 wt%, about 0.2 wt% to about 0.3 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 3- amino-3-methyl-2-butanol, 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 3-amino-3-methyl-2-butanol based on the total weight of the composition.
[0031] In any aspect and / or embodiment herein, the composition may further include an amino alcohol other than 3-amino-3-methyl-2-butanol (an “other amino alcohol”), where exemplary other amino alcohols that may be included in a composition according to any embodiment herein include, but are not limited to, 2-aminoethanol, triethanolamine, 1-amino- 2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3- propanediol, 3-(ethylamino)-3-methylbutan-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., 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-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 -10- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 composition of any embodiment herein may include an other amino alcohol (e.g., 2- aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino- 1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-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.
[0032] As discussed previously, the composition may exhibit a biobased content of the 3- amino-3-methyl-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of 0% to 100%¾thus, in any embodiment herein, the composition may exhibit a biobased content of the 3-amino-3-methyl-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-3-methyl-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-3- methyl-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 25%. Accordingly, the 3-amino-3-methyl-2-butanol of any aspect and / or embodiment herein may be a renewable, biobased compound that exhibits low toxicity while concurrently providing comparable or superior performance as compared to petroleum- based alternatives and superior performance as compared to current renewable alternatives (e.g., NH3). -11- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767
[0033] Personal care compositions of the present technology may include a solvent. The solvent may include water, alcohol (ethanol, isopropanol, or a mixture thereof), vegetable oils (e.g., coconut oil, olive oil, sunflower oil, avocado oil, almond oil, argan oil, jojoba oil, flaxseed oil, sesame oil, and / or hemp oil), animal oils (e.g., lanolin, beeswax, and / or tallow), mineral oil, glycerin, glycol ethers (e.g., butylene glycol, propylene glycol, hexylene glycol, and / or ethylene glycol), silicones (e.g., dimethicone, cyclopentasiloxane, cyclohexasiloxane, trimethylsiloxysilicate, phenyl trimethicone, and / or polysilicone-11), or a combination of any two or more thereof. The solvent may be used as a carrier when preparing and / or applying the personal care 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 in-between 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 20 wt% to about 80 wt% solvent.
[0034] Personal care compositions of the present technology may include a mixture of alcohol (e.g., ethanol, isopropanol, or mixtures thereof) and water. For example, the composition may include a water and alcohol in a weight ratio of 300:1 to about 1:300, e.g., about 300:1, about 150:1, about 75:1, about 37:1, about 18:1, about 9:1, about 4:1, about 3:1, about 2:1, 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.
[0035] Personal care compositions of the present technology may include an emulsion. The emulsion may be a water-in-oil or oil-in-water emulsion. In some embodiments, water may make up the balance of the composition, which may be about 20 wt% to about 80 wt% of the -12- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 total composition. In addition to water, organic solvents may optionally be included as solvent. Examples include alcohols as described herein, ester oils like isopropyl myristate, cetyl myristate, 2-octyldodecyl myristate, coconut oil, olive oil, sunflower oil, avocado oil, almond oil, argan oil, jojoba oil, flaxseed oil, sesame oil, hemp oil, and mineral oil. Such ester oils may assist in emulsifying such emulsion compositions. The composition may include additional emulsifying agents (e.g., stearic acid). 3-amino-3-methyl-2-butanol may also assist in emulsifying such emulsion compositions. Where the composition comprises an emulsion and a pigment, the pigment may be dispersed in the oil phase or the aqueous phase.
[0036] Acidic neutralization additives used to partially or completely neutralize the acids and / or acid groups of polymers include 2-amino-2-methyl-1-propanol (AMP), 2-amino-2- methyl-1,3-propanediol (AMPD), ammonium hydroxide, morpholine, cyclohexylamine, dimethyl stearamine (DMS), monoethanolamine (MEA), diethanolamine (DEA), triethanolamine (TEA), monoisopropanolamine (MIPA), and triisopropanolamine (TIPA). 3- amino-3-methyl-2-butanol may be used to replace one or more of these neutralization agents in part or in whole. The composition may have a pH of about 5 to about 9, about 5.5 to about 8.5, about 6 to about 8, about 6.5 to about 7.5, or about 7.
[0037] In any embodiment herein, the composition may comprise a molecule comprising an acid group (i.e., one or more acid groups), and an amount of neutralization agent (i.e., 3- amino-3-methyl-2-butanol) effective to partially or completely neutralize the acid groups, and solvent. The molecule comprising the acid group may further be a polymer as described herein.
[0038] 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%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, or 40 wt%, of the molecule comprising the acid group, or any range including and / or in-between any two of these values. The composition may include about 0.001 wt% to about 40 wt% molecule comprising the acid group, e.g., about 0.01 wt% to about 40 wt%, about 0.05 wt% to about 15 wt%, about 0.1 wt% to about 5 wt%, about 10 wt% to about 30 wt%, or any range including and / or in- -13- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 between any two of these values. In some embodiments, the compositions may include about 0.1 wt% to about 5 wt% molecule comprising the acid group.
[0039] The acid group of the molecule comprising the acid group may include a carboxylic acid, sulfonic acid, phosphonic acid, and / or phosphoric acid group. The composition may include one or multiple molecules having acid groups, each independently having an acid group selected from the group consisting of carboxylic acids, sulfonic acids, phosphonic acids, phosphoric acid groups, or a combination of two or more thereof. In some embodiments, the molecule comprising the acid group includes a carboxylic acid. The carboxylic acid may include alpha hydroxycarboxylic acids (“AHAs”; e.g., glycolic acid, lactic acid, mandelic acid, and citric acid) and / or alkyl ether carboxylic acids. For example, the carboxylic acids may include isostearic acid, lauric acid, palmitic acid, oleic acid, stearic acid, lactic acid, myristic acid, acetic acid, propionic acid, succinic acid, glutaric acid, adipic acid, hexanoic acid, heptanoic acid, octanoic acid, sebacic acid, citric acid, and combinations of any two or more thereof. In some embodiments, the molecule comprising the acid group includes a sulfonic acid. The sulfonic acid may include alkyl sulfates and / or alkyl ether sulfates having the formula ROSO3M and R-O(C2H4O)xSO3M, respectively, wherein R is alkyl or alkenyl of from 8 to 18 carbon atoms, x is an integer having a value of from about 1 to about 10, and M is a cation such as ammonium, alkanolamines such as triethanolamine, monovalent metals such as sodium and potassium, and polyvalent metal cations such as magnesium, and calcium. For example, R may have 12 to 14 carbon atoms, in a linear rather than branched chain. For example, the sulfonic acid may include sodium lauryl sulfate and sodium lauryl ether sulfate, and combinations thereof. For example, the phosphoric acid group may be cetyl phosphate.
[0040] Any composition disclosed herein may further include an ester, e.g., isopropyl isostearate, hexyl laurate, isohexyl laurate, isohexyl palmitate, isopropyl palmitate, decyl oleate, isodecyl oleate, hexadecyl stearate, decyl stearate, isopropyl isostearate, dihexyldecyl adipate, lauryl lactate, myristyl lactate, cetyl lactate, oleyl stearate, oleyl oleate, oleyl myristate, lauryl acetate, cetyl propionate, oleyl adipate, C7 to C22 esters of succinic acid, diisopropyl adipate, diisohexyl adipate, diisopropyl sebacate, isocetyl stearoyl stearate, tristearyl citrate, and combinations of any two or more thereof. -14- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767
[0041] In some embodiments, 3-amino-3-methyl-2-butanol neutralizes at least about 20% of the molecule comprising the acid group (e.g., at least about 30%, at least about 40%, or at least about 50%). In some embodiments, the 3-amino-3-methyl-2-butanol neutralizes about 20% to about 100% of the molecule comprising the acid group (e.g., about 30% to about 90% or about 40% to about 80%). In some embodiments, the molar ratio of the 3-amino-3- methyl-2-butanol to the molecule comprising the acid group may be about 1:5 to about 5:1 (e.g., about 1:4 to about 2:1, about 1:3 to about 2:1, or about 1:2 to about 1:1).
[0042] In some embodiments, the molecule comprising the acid group may be a polymer (e.g., the polymer comprising one or more acid groups). Compositions may include the polymer, an amount of neutralization agent (e.g., 3-amino-3-methyl-2-butanol) effective to partially or completely neutralize the acid group, and solvent.
[0043] 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%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, or 40 wt%, of the polymer comprising acid groups, or any range including and / or in-between any two of these values. The composition may include about 0.001 wt% to about 40 wt% of the polymer comprising acid groups, e.g., about 0.01 wt% to about 40 wt%, about 0.05 wt% to about 15 wt%, about 0.1 wt% to about 5 wt%, about 0.5 wt% to about 4 wt%, about 0.1 wt% to about 1 wt%, about 10 wt% to about 30 wt%, about 2 wt% to about 15 wt%, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include about 0.1 wt% to about 5 wt% polymer comprising acid groups.
[0044] The acid groups of the polymer comprising acid groups may include carboxyl, sulfonyl, phosphonyl, phosphoryl groups, or a combination of any two or more thereof. In some embodiments, the composition may comprise multiple polymers having acid groups, with each polymer having acid groups independently chosen from carboxyl, sulfonyl, phosphonyl, phosphoryl groups, or a combination of any two or more thereof. In some embodiments, the acid functional groups are carboxyl groups. In some embodiments, the polymers may have acid values of about 0.1 to about 10 mEq / g. In some embodiments, the -15- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 polymers may have acid values of about 0.5 to about 5 mEq / g or about 1 to about 4 mg mEq / g.
[0045] The polymer comprising acid groups may be selected from the group consisting of polyacrylate copolymers, vinyl acetate copolymer, or combinations thereof. In some embodiments, the polymer comprising acid groups may be ethyl acrylate, methyl methacrylate and methacrylic acid copolymer; ethyl acrylate, t-butyl acrylate and methacrylic acid copolymer; octyl acrylamide, acrylates and butylaminoethyl methacrylate copolymer; methacrylic acid, n-butyl acrylate and methyl methacrylate copolymer; methacrylic acid, n- butyl acrylate and ethyl methacrylate copolymer; butyl acrylate, methyl methacrylate, hydroxyethyl methacrylate and methacrylic acid copolymer; vinyl acetate, crotonates and vinyl neodecanoate copolymer; a butyl ester of vinyl methyl ether and maleic anhydride copolymer; an ethyl ester of vinyl methyl ether and maleic anhydride copolymer; vinyl acetate and vinylpyrrollidone copolymer; acrylates / steareth-20 methacrylate crosspolymer; hyaluronic acid; carbomers; or copolymers or mixtures of any two or more thereof.
[0046] Compositions of the present technology may include one or more polymers comprising acid groups with a wide range of molecular weights. For example, the compositions may include polymers comprising acid groups with an average molecular weight of at least about 10 kDa, at least about 25 kDa, at least about 50 kDa, at least about 100 kDa, at least about 150 kDa, at least about 200 kDa, at least about 250 kDa, at least about 300 kDa, at least about 400 kDa, at least about 500 kDa, at least about 600 kDa, at least about 700 kDa, at least about 800 kDa, at least about 900 kDa, or at least about 1000 kDa, or a range between and including any two of the foregoing values. For example, the compositions may include polymers comprising acid groups with an average molecular weight of about 10 kDa to about 1000 kDa, of about 25 kDa to about 500 kDa, about 300 kDa to about 400 kDa, 600 kDa to about 700 kDa, or about 50 kDa to about 300 kDa. The polymer comprising acid groups may be cross-linked.
[0047] In some embodiments, 3-amino-3-methyl-2-butanol neutralizes at least about 20% of the acid functional groups on the polymer (e.g., at least about 30%, at least about 40%, or at least about 50%). In some embodiments, the 3-amino-3-methyl-2-butanol neutralizes about 20% to about 100% of the acid functional groups on the polymer (e.g., about 30% to about -16- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 90% or about 40% to about 80%). In some embodiments, the molar ratio of the 3-amino-3- methyl-2-butanol to the acid functional groups on the polymer may be about 1:5 to about 5:1 (e.g., about 1:4 to about 2:1, about 1:3 to about 2:1, or about 1:2 to about 1:1).
[0048] In any embodiment, the composition may further comprise one or more additives selected from a preservative, thickener, water-miscible co-solvent, water immiscible co- solvent, anti-microbial, non-ionic polymer, dye, fragrance, and corrosion inhibitors.
[0049] In some embodiments, the composition may comprise anionic and / or zwitterionic surfactants. The anionic and / or zwitterionic surfactant may be selected from the group consisting of fatty acids, alkyl sulfates, alkyl(oxyalkyl)(n) sulfates where n is the average degree of alkoxylation from 1 to 3, alkyl sulfonates, alkenyl sulfonates, alkylamidealkylbetaines, and combinations of two or more thereof. For example, the anionic and / or zwitterionic surfactant may be sodium lauryl sulfate, ammonium lauryl sulfate, sodium or ammonium laureth(n) sulfate where n is the average degree of ethoxylation from 1 to 3, alkoxyalkylsodium lauryl sulfate, sodium laureth sulfate, cocamidopropyl betaine, and combinations of two or more thereof. In some embodiments, the composition may comprise about 1% to about 50% of the anionic and / or zwitterionic surfactant. In some embodiments, the composition may comprise about 5% to about 40% of the anionic and / or zwitterionic surfactant.
[0050] In some embodiments, the composition may comprise alcohol. In some embodiments, the alcohol may be ethanol, n-propanol, isopropanol, or a combination of two or more thereof. For example, in some embodiments, the composition may include at least about 20 wt% alcohol, at least about 25 wt% alcohol, at least about 30 wt% alcohol, at least about 35 wt% alcohol, at least about 40 wt% alcohol, at least about 45 wt% alcohol, at least about 50 wt% alcohol, at least about 55 wt% alcohol, at least about 60 wt% alcohol, at least about 65 wt% alcohol, at least about 70 wt% alcohol, at least about 75 wt% alcohol, at least about 80 wt% alcohol, at least about 85 wt% alcohol, at least about 90 wt% alcohol, or a range between and including any two of the foregoing values. For example, in some embodiments, the compositions may comprise from about 40% to about 95% of the alcohol, from about 50% to about 80% of the alcohol, or from about 60% to about 70% of the alcohol. -17- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 Hair Styling Aerosols and Similar Products
[0051] In one aspect, the present technology provides compositions for hair styling aerosols and similar products comprising acrylate resins, neutralization agents (i.e., 3-amino-3- methyl-2-butanol), propellants, and / or solvents. Without being bound by any theory, the 3- amino-3-methyl-2-butanol may provide in-can corrosion protection in addition to acting as a neutralizing agent.
[0052] In some embodiments, the hair styling aerosol composition may comprise an acrylic resin. For example, the acrylic resin may include an acrylate / hydroxyester acrylate copolymer. The acrylic resin may include AMPHOMER® (Nouryon), ACUDYNE™ 180 (Dow), ACUDYNE 1000 (Dow), AMERHOLD, LUVIMER 100P, LUVIMER 36D, LUVIMER 30E, ACULYN 88, ACULYN 44, ACULYN 33A, or a combination of any two or more thereof. In some embodiments the composition may include acetate resins or combinations of acetate and acrylate resins. For example, RESYN 28-2930, GANTREZ ES- 225, and LUVISKOL VA may also be used. Amounts of such resins may range from about 0.001 wt% to about 15 wt%, e.g., any of about 0.001, 0.01, 0.1, 1, 2, 3, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 wt% or a range between and including any two of the foregoing values, such as about 0.2 wt% to about 15 wt%, 0.02 wt% to about 0.3 wt%, 2 wt% to about 15 wt%, about 2 wt% to about 4 wt% , about 4 wt% to about 7 wt% or about 6 wt% to about 10 wt%.
[0053] In some embodiments, the hair styling aerosol composition may comprise propellants such as propane, butane, isobutane, dimethyl ether, 1-1-difluorethane, methyl acetate, or a combination of two or more thereof. VOC propellants may make up to about 30-35 wt% of the compositions. Low VOC propellants such as 152A may make up to 40-50% of the compositions.
[0054] The hair styling aerosol compositions may include a wide range of amounts of the neutralization agent 3-amino-3-methyl-2-butanol described herein. For example, the compositions may include about 0.005 wt% to about 10 wt% of 3-amino-3-methyl-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 0.02 wt% to about 2 wt%, about 0.05 wt% to about 1 -18- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 wt%, about 0.1 wt% to about 20 wt%, about 0.1 wt% to about 5 wt%, about 0.4 wt% to about 3 wt%, about 0.2 wt% to about 2 wt%, about 0.1 wt% to about 1 wt%, about 0.2 wt% to about 0.3 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 3-amino-3-methyl-2-butanol, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include from about 0.4 wt% to about 3 wt% of the 3-amino-3-methyl-2-butanol based on the total weight of the composition.
[0055] The hair styling aerosol compositions may include water. In some embodiments, the compositions may include at least about 5 wt% water, at least about 10 wt% water, at least about 15 wt% water, at least about 20 wt% water, at least about 25 wt% water, at least about 30 wt% water, at least about 40 wt% water, at least about 50 wt% water, at least about 60 wt% water, at least about 70 wt% water at least about 80 wt% water, at least about 85 wt% water, at least about 90 wt% water, or a range between and including any two of the foregoing values. In some embodiments, the compositions may include less than 1 wt%, less than 0.1 wt%, less than 0.01 wt%, or less than 0.001 wt% water. In some embodiments, the compositions may include about 0.001 wt% to about 0.1 wt%, about 0.01 wt% to about 1 wt%, or about 5 wt% to about 30 wt% water. In some embodiments, the compositions may include about 25 wt% to about 35 wt% water.
[0056] The hair styling aerosol compositions may also include an alcohol (e.g., ethanol) In some embodiments, the compositions may include at least about 20 wt%, at least about 25 wt%, at least about 30 wt%, at least about 35 wt%, at least about 40 wt%, at least about 45 wt%, at least about 50 wt%, at least about 55 wt%, at least about 60 wt%, at least about 65 wt%, at least about 70 wt%, at least about 75 wt%, at least about 80 wt%, at least about 85 wt%, at least about 90 wt% of alcohol, or a range between and including any two of the foregoing values. For example, in some embodiments, the compositions include about 10 -19- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 wt% to about 90 wt%, or about 40 wt% to about 60 wt% ethanol. In some embodiments, the compositions include about 50 wt% ethanol. Hair Styling Gels and Similar Products
[0057] In an aspect, the present technology provides compositions for hair styling gels and similar products comprising film forming agents and fixatives (e.g., ACUDYNE™ 1000), neutralization agents (i.e., 3-amino-3-methyl-2-butanol), suspending agents and stabilizers (e.g., ACULYN™ 88), preservatives (e.g., Euxyl® PE 9010), and / or water. Compositions of the present technology may include polymers comprising acid groups used as film forming agents and / or fixatives (e.g., ACUDYNE™ 1000). The film forming agents and / or fixatives may include an acrylate / hydroxyester acrylate copolymer.
[0058] For example, the hair styling gel compositions may include from about 0.01 wt% to about 10 wt% of the film forming agent and fixative based on the total weight of the composition, including from about 0.05 wt% to about 5 wt%, from about 0.5 wt% to about 4 wt%, from about 1 wt% to about 3 wt%, or from about 1.5 wt% to about 2.5 wt%. In some embodiments, the compositions may include about 0.5 wt%, about 1.0 wt%, about 1.5 wt%, about 1.6 wt%, about 1.7 wt%, about 1.8 wt%, about 1.9 wt%, about 2.0 wt%, about 2.1 wt%, about 2.2 wt%, about 2.3 wt%, about 2.4 wt%, about 2.5 wt%, about 3.0 wt%, about 3.5 wt%, about 4.0 wt%, or about 5.0 wt% of the film forming agents and fixatives, or a range between and including any two of the foregoing values.
[0059] The hair styling gel compositions may include suspending agents and stabilizers (e.g., ACULYN™ 88). For example, the compositions may include from about 0.005 wt% to about 10 wt% of the suspending agents and stabilizers based on the total weight of the composition, including from about 0.05 wt% to about 5 wt%, from about 1 wt% to about 4 wt%, from about 2 wt% to about 4 wt%, or from about 2.5 wt% to about 3.5 wt%. In some embodiments, the compositions may include about 0.5 wt%, about 1.0 wt%, about 1.5 wt%, about 2.0 wt%, about 2.5 wt%, about 2.6 wt%, about 2.7 wt%, about 2.8 wt%, about 2.9 wt%, about 3.0 wt%, about 3.1 wt%, about 3.2 wt%, about 3.3 wt%, about 3.4 wt%, about 3.5 wt%, about 4.0 wt%, about 4.5 wt%, or about 5.0 wt% of the suspending agents and stabilizers, or a range between and including any two of the foregoing values. -20- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767
[0060] The hair styling gel compositions may include a wide range of amounts of the neutralization agent 3-amino-3-methyl-2-butanol described herein. For example, the compositions may include about 0.005 wt% to about 10 wt% of 3-amino-3-methyl-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 0.02 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 0.4 wt% to about 3 wt%, about 0.2 wt% to about 2 wt%, about 0.1 wt% to about 1 wt%, about 0.2 wt% to about 0.3 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 3-amino-3-methyl-2-butanol, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include from about 0.1 wt% to about 0.5 wt% of the 3-amino-3-methyl-2-butanol based on the total weight of the composition.
[0061] The hair styling gel compositions may include water. In some embodiments, the compositions may include at least about 20 wt% water, at least about 25 wt% water, at least about 30 wt% water, at least about 35 wt% water, at least about 40 wt% water, at least about 45 wt% water, at least about 50 wt% water, at least about 55 wt% water, at least about 60 wt% water, at least about 65 wt% water, at least about 70 wt% water, at least about 75 wt% water, at least about 80 wt% water, at least about 85 wt% water, at least about 90 wt% water, or a range between and including any two of the foregoing values. In some embodiments, the compositions may include about 20 wt% to about 99 wt% water, about 35 wt% to about 97 wt%, about 45 wt% to about 95 wt%, about 50 wt% to about 95 wt%, or a range between and including any two of the foregoing values. In some embodiments, the compositions may include about 93 wt% to about 98 wt% water.
[0062] Compositions of the present technology may include a wide range of preservatives (e.g., Euxyl® PE 9010). For example, the compositions may include from about 0.01 wt% to -21- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 about 10 wt% of preservative based on the total weight of the composition, including from about 0.05 wt% to about 5 wt%, from about 0.05 wt% to about 2 wt%, from about 0.05 wt% to about 1 wt%, from about 0.25 wt% to about 0.75 wt%, from about 0.35 wt% to about 0.65 wt%, or from about 0.4 wt% to about 0.6 wt%. In some embodiments, the compositions may include about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt% about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1 wt%, about 1.5 wt%, about 2 wt%, about 3 wt%, about 4 wt%, or about 5 wt% of preservative, or a range between and including any two of the foregoing values. Hand Sanitizers and Similar Products
[0063] In one aspect, the present technology provides compositions for hand sanitizers and similar products comprising thickening agents (e.g., Carbopol® 980, a polymer including acid groups), neutralization agents (i.e., 3-amino-3-methyl-2-butanol), disinfectants (e.g., ethanol), and / or water.
[0064] The hand sanitizer compositions of the present technology may include a wide range of amounts of the neutralization agent 3-amino-3-methyl-2-butanol described herein. For example, the compositions may include about 0.005 wt% to about 10 wt% of 3-amino-3- methyl-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 0.02 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 0.4 wt% to about 3 wt%, about 0.2 wt% to about 2 wt%, about 0.1 wt% to about 1 wt%, about 0.2 wt% to about 0.3 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 3-amino-3-methyl-2-butanol, or any range including and / or in- between any two of these values. In some embodiments, the compositions may include from about 0.01 wt% to about 0.1 wt% of the 3-amino-3-methyl-2-butanol based on the total weight of the composition. -22- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767
[0065] The hand sanitizer compositions of the present technology may include thickening agents such as Carbopol® 980 (a crosslinked polyacrylic acid) or an acrylates / steareth-20 methacrylate crosspolymer. For example, the compositions may include from about 0.05 wt% to about 10 wt% of thickening agent based on the total weight of the composition, including from about 0.05 wt% to about 5 wt%, from about 0.05 wt% to about 2 wt%, from about 0.05 wt% to about 0.5 wt%, from about 0.05 wt% to about 0.3 wt%, from about 0.1 wt% to about 0.3 wt%, or from about 0.2 wt% to about 0.3 wt%. In some embodiments, the compositions may include about 0.05 wt%, about 0.1 wt%, about 0.15 wt%, about 0.2 wt%, about 0.25 wt%, about 0.3 wt%, about 0.35 wt%, about 0.4 wt%, about 0.45 wt%, about 0.5 wt%, about 0.75 wt%, or about 1 wt%, or a range between and including any two of the foregoing values.
[0066] The hand sanitizer compositions of the present technology may include water. In some embodiments, the compositions may include at least about 10 wt% water, at least about 15 wt% water, at least about 20 wt% water, at least about 25 wt% water, at least about 30 wt% water, at least about 35 wt% water, or at least about 40 wt% water, or a range between and including any two of the foregoing values. In some embodiments, the compositions may include about 20 wt% to about 40 wt% water, about 25 wt% to about 35 wt%, about 27 wt% to about 33 wt%, about 28 wt% to about 32 wt%, or a range between and including any two of the foregoing values.
[0067] The hand sanitizer compositions of the present technology may also include an alcohol, e.g., ethanol, isopropanol, or mixtures thereof. In some embodiments, the compositions may include at least about 20 wt% alcohol, at least about 25 wt% alcohol, at least about 30 wt% alcohol, at least about 35 wt% alcohol, at least about 40 wt% alcohol, at least about 45 wt% alcohol, at least about 50 wt% alcohol, at least about 55 wt% alcohol, at least about 60 wt% alcohol, at least about 65 wt% alcohol, at least about 70 wt% alcohol, at least about 75 wt% alcohol, at least about 80 wt% alcohol, at least about 85 wt% alcohol, at least about 90 wt% alcohol, or a range between and including any two of the foregoing values. -23- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 Pigmented Products and Suncreens
[0068] Personal care compositions of the present technology may include a pigment (e.g., for use as a sunscreen and / or a color cosmetic). Examples of color cosmetics include lipsticks, foundations, concealers, blushes, eye shadow, eyeliners, lip glosses, lip balms, brow gels, tinted sunscreens, and similar products. The pigment may have the form of a powder, such that the composition is an emulsion or dispersion. In some embodiments, the pigment may be a metal, metal oxide, ceramic, or carbon-containing material. Illustrative pigments comprise titanium dioxide, zinc oxide, black iron oxide, red iron oxide, aluminum oxide, aluminum metal, mica, ultramarines, carmine, carbon black, and combinations of any two or more thereof. The composition 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%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, or 40 wt%, of the pigment, or any range including and / or in-between any two of these values. The composition may include about 0.001 wt% to about 40 wt% pigment, e.g., about 0.01 wt% to about 40 wt%, about 0.05 wt% to about 15 wt%, about 0.1 wt% to about 5 wt%, about 0.5 wt% to about 4 wt%, about 0.1 wt% to about 1 wt%, about 10 wt% to about 30 wt%, about 2 wt% to about 20 wt%, or any range including and / or in between any two of these values.
[0069] In an aspect, the present technology provides compositions for color cosmetics and similar products. The color cosmetics may include a pigment, neutralization agents (i.e., 3- amino-3-methyl-2-butanol), and solvent.
[0070] In an aspect, the present technology provides compositions for sunscreens and similar products. The sunscreen compositions may be mineral sunscreen compositions that include a pigment, a surfactant (e.g., fatty acids like stearic acid), neutralization agents (i.e., 3-amino-3- methyl-2-butanol), and solvent. The sunscreen compositions may alternatively or additionally include chemical sunscreens (e.g., phenylbenzimidazole sulfonic acid and aminobenzoic acids), neutralization agents (i.e., 3-amino-3-methyl-2-butanol), and solvent. -24- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767
[0071] In some embodiments of the sunscreen compositions, the pigment comprises a metal oxide used as a mineral sunscreen. For example, the pigment may include titanium oxide, zinc oxide, or a combination thereof. Amounts of such pigments may range from about 2 wt% to about 75 wt%, e.g., any of about 2, 4, 6, 8, 10, 12, 14, 16, 18, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, or 75 wt%, or a range between and including any two of the foregoing values, such as about 5 wt% to about 30 wt%, about 10 wt% to about 20 wt%, or about 14 wt%.
[0072] In some embodiments of the sunscreen compositions, the chemical sunscreen comprises phenylbenzimidazole sulfonic acid and / or an aminobenzoic acid (e.g., para- aminobenzoic acid (PABA), glyceryl PABA, padimate O (octyl dimethyl PABA), roxadimate, and a combination of any two or more thereof). Amounts of such chemical sunscreens may range from about 2 wt% to about 75 wt%, e.g., any of about 2, 4, 6, 8, 10, 12, 14, 16, 18, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, or 75 wt%, or a range between and including any two of the foregoing values, such as about 5 wt% to about 30 wt%, about 10 wt% to about 20 wt%, or about 14 wt%.
[0073] Sunscreen and / or color cosmetic compositions of the present technology may include a wide range of surfactants. For example, the surfactant may be stearic acid. For example, the compositions may include from about 0.005 wt% to about 40 wt% of the surfactant based on the total weight of the composition, including from about 0.05 wt% to about 20 wt%, from about 1 wt% to about 20 wt%, from about 2 wt% to about 20 wt%, or from about 25 wt% to about 15 wt%. In some embodiments, the compositions may include about 1.0 wt%, about 2.0 wt%, about 3.0 wt%, about 4.0 wt%, about 5.0 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 40 wt% of the surfactant, or a range between and including any two of the foregoing values.
[0074] Sunscreen and / or color cosmetic compositions of the present technology may include a wide range of amounts of the neutralization agent 3-amino-3-methyl-2-butanol described herein. For example, the compositions may include about 0.005 wt% to about 10 wt% of 3- amino-3-methyl-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 0.02 wt% to about 2 wt%, about -25- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 0.05 wt% to about 1 wt%, about 0.1 wt% to about 20 wt%, about 0.1 wt% to about 5 wt%, about 0.4 wt% to about 3 wt%, about 0.2 wt% to about 2 wt%, about 0.1 wt% to about 1 wt%, about 0.2 wt% to about 0.3 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 3-amino-3-methyl-2-butanol, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include from about 0.01 wt% to about 0.1 wt% of the 3-amino-3-methyl-2-butanol based on the total weight of the composition.
[0075] Sunscreen and / or color cosmetic compositions of the present technology may further include additional neutralization agents besides 3-amino-3-methyl-2-butanol to provide pH balancing. The additional neutralization agent may be selected from triethanolamine, sodium hydroxide, aminomethyl propanol, tromomethamine, or a combination of two or more thereof. The additional neutralization agent may be present in an amount of about 0.005 wt% to about 10 wt%, e.g., about 0.01 wt% to about 0.1 wt%.
[0076] Sunscreen and / or color cosmetic compositions of the present technology may further include a humectant to attract moisture to the skin and provide skin hydration and moisturizing properties. Illustrative humectants include sugar alcohols (e.g., glycerol), polyalkylene glycol (e.g., polyethylene glycol), hydroxyethyl urea, hyaluronic acid, ceramides, glycerin, or combinations of any two or more thereof. The humectant may be present in an amount of about 0.1 wt% to about 50 wt%, e.g., 0.1 wt% to about 20 wt%, about 0.1 wt% to about 10 wt%, about 0.1 wt% to about 5 wt%, about 1 wt% to about 5 wt%, or about 3 wt%.
[0077] Sunscreen and / or color cosmetic compositions of the present technology may include a wide range of preservatives (e.g., a mixture of benzyl alcohol, ethylhexylglycerin, and tocopherol; and / or Euxyl® PE 9010). For example, the compositions may include from about 0.01 wt% to about 10 wt% of preservative based on the total weight of the composition, including from about 0.05 wt% to about 5 wt%, from about 0.05 wt% to about 2 wt%, from -26- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 about 0.05 wt% to about 1 wt%, from about 0.25 wt% to about 0.75 wt%, from about 0.35 wt% to about 0.65 wt%, or from about 0.4 wt% to about 0.6 wt%. In some embodiments, the compositions may include about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt% about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1 wt%, about 1.5 wt%, about 2 wt%, about 3 wt%, about 4 wt%, or about 5 wt% of preservative, or a range between and including any two of the foregoing values.
[0078] Sunscreen and / or color cosmetic compositions of the present technology may include a wide range of emollients (e.g., caprylic / capric triglyceride and / or C12-15 alkyl benzoate, silicone oils, and synthetic esters). For example, the compositions may include from about 0.005 wt% to about 40 wt% of the emollients based on the total weight of the composition, including from about 0.05 wt% to about 20 wt%, from about 1 wt% to about 20 wt%, from about 2 wt% to about 20 wt%, or from about 25 wt% to about 15 wt%. In some embodiments, the compositions may include about 1.0 wt%, about 2.0 wt%, about 3.0 wt%, about 4.0 wt%, about 5.0 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 40 wt% of the emollients, or a range between and including any two of the foregoing values.
[0079] Where the sunscreen and / or color cosmetic composition of the present technology comprises an emulsion, the composition may include a wide range of emulsifying agents. For example, the emulsifying agent may include ester oils as disclosed herein, glyceryl stearate, polysorbate 20, and any combination of two or more thereof. Lotions, creams, low-pigment and pigment-free cosmetics, and similar products
[0080] In an aspect, the present technology provides compositions for lotions, creams, low- pigment and pigment-free cosmetics, and similar products for application to the skin of the face or body, or to eyelashes or eyebrows. Non-limiting examples of pigment-free and low- pigment cosmetics include types of mascaras, foundations, lipsticks, blushes, eye shadows, lip glosses, and brow gels. Low-pigment cosmetics may have, e.g., less than 10 wt%, 5 wt%, 2 wt%, or 1 wt% pigment. Pigment-free and low-pigment cosmetics may be used to create a more natural look, for people who prefer a less intense color, or for those who are sensitive to -27- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 certain pigments. These compositions comprise a polymer comprising acid groups, neutralization agents (i.e., 3-amino-3-methyl-2-butanol), and solvent.
[0081] The polymer with acid groups may act as a thickening agent, emulsifier, stabilizer, film-forming agent, humectant, fixative, or a combination of any two or more thereof. Illustrative polymers comprising acid groups that may be included in the lotion or cream compositions disclosed herein include carbomers, polyacrylic acid, sodium hyaluronate / hyaluronic acid, and acrylic acid copolymers.
[0082] The lotions, creams, low-pigment and pigment-free cosmetic compositions of the present technology may include a wide range of amounts of the neutralization agent 3-amino- 3-methyl-2-butanol described herein. For example, the compositions may include about 0.005 wt% to about 10 wt% of 3-amino-3-methyl-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 0.02 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 0.4 wt% to about 3 wt%, about 0.2 wt% to about 2 wt%, about 0.1 wt% to about 1 wt%, about 0.2 wt% to about 0.3 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 3- amino-3-methyl-2-butanol, or any range including and / or in-between any two of these values. In some embodiments, the compositions may include from about 0.1 wt% to about 10 wt% of the 3-amino-3-methyl-2-butanol based on the total weight of the composition.
[0083] The lotions, creams, low-pigment and pigment-free cosmetic compositions of the present technology may further include a humectant to attract moisture to the skin and provide skin hydration and moisturizing properties. Illustrative humectants include sugar alcohols (e.g., glycerol), polyalkylene glycol (e.g., polyethylene glycol), hydroxyethyl urea, hyaluronic acid, ceramides, glycerin, or combinations of any two or more thereof. The humectant may be present in an amount of about 0.1 wt% to about 50 wt%, e.g., 0.1 wt% to -28- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 about 20 wt%, about 0.1 wt% to about 10 wt%, about 0.1 wt% to about 5 wt%, about 1 wt% to about 5 wt%, or about 3 wt%.
[0084] The lotions, creams, low-pigment and pigment-free cosmetic compositions of the present technology may include a wide range of emollients (e.g., caprylic / capric triglyceride and / or C12-15 alkyl benzoate, coconut oil, olive oil, sunflower oil, avocado oil, almond oil, argan oil, jojoba oil, flaxseed oil, sesame oil, hemp oil, silicone oils, and synthetic esters). For example, the compositions may include from about 0.005 wt% to about 40 wt% of the emollients based on the total weight of the composition, including from about 0.05 wt% to about 20 wt%, from about 1 wt% to about 20 wt%, from about 2 wt% to about 20 wt%, or from about 25 wt% to about 15 wt%. In some embodiments, the compositions may include about 1.0 wt%, about 2.0 wt%, about 3.0 wt%, about 4.0 wt%, about 5.0 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 40 wt% of the emollients, or a range between and including any two of the foregoing values.
[0085] Where the lotions, creams, low-pigment and pigment-free cosmetic compositions of the present technology comprises an emulsion, the composition may include a wide range of emulsifying agents. For example, the emulsifying agent may include ester oils as disclosed herein, glyceryl stearate, polysorbate 20, and any combination of two or more thereof.
[0086] The lotions, creams, low-pigment and pigment-free cosmetic compositions of the present technology may include a wide range of preservatives (e.g., a mixture of benzyl alcohol, ethylhexylglycerin, and tocopherol; and / or Euxyl® PE 9010). For example, the compositions may include from about 0.01 wt% to about 10 wt% of preservative based on the total weight of the composition, including from about 0.05 wt% to about 5 wt%, from about 0.05 wt% to about 2 wt%, from about 0.05 wt% to about 1 wt%, from about 0.25 wt% to about 0.75 wt%, from about 0.35 wt% to about 0.65 wt%, or from about 0.4 wt% to about 0.6 wt%. In some embodiments, the compositions may include about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt% about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1 wt%, about 1.5 wt%, about 2 wt%, about 3 wt%, about 4 wt%, or about 5 wt% of preservative, or a range between and including any two of the foregoing values. -29- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 Methods of Manufacturing the Personal Care Products
[0087] The compositions described herein may be manufactured by conventional personal care manufacturing techniques, which are well known to those skilled in the art. Typically, the compositions are manufactured by a two-step process. First, a mixture of some or all of the components of the composition besides the neutralizing agent (i.e., AMB) is prepared by mixing (e.g., high shear agitation to provide a high viscosity and high solids mixture). This step of the process is intended to form a homogeneous mixture with a stable pH.
[0088] The second step of the personal care manufacturing process includes adding an effective amount of the neutralizing agent to neutralize or partially neutralize acidic components of the composition (e.g. the molecule including an acid group, such as when the molecule includes a polymer including an acid group) to achieve a predetermined pH of the composition. In some embodiments, the pH of the composition may be raised to about 5 to about 9 or about 6 to about 8.
[0089] In accordance with any of the foregoing embodiments, also provided herein is a method comprising adding to a composition comprising a molecule comprising an acid group, an effective amount of 3-amino-3-methyl-2-butanol to raise the pH of the composition, stabilize the composition, and / or at least partially neutralize any acid groups in the composition. Here, at least partially neutralizing an acid group means adding 3-amino-3- methyl-2-butanol in sufficient amounts to reduce the acidity of the solution such that the pH of the solution increases by at least 0.1 unit without necessarily reaching neutralizing pH 7. In some embodiments, the pH of the composition after neutralizing may be about 5 to about 9 or about 6 to about 8. In some embodiments, the composition is stable for at least about 1 month, at least about 2 months, at least about 3 months, at least about 6 months, at least about 12 months, or at least about 24 months. In some embodiments, the 3-methyl-2-butanol neutralizes at least about 20% of the acid groups (e.g., at least about 30%, at least about 40%, or at least about 50%). In some embodiments, the 3-methyl-2-butanol neutralizes about 20% to about 100% of the acid groups of the polymer comprising acid groups (e.g., about 30% to about 90% or about 40% to about 80%). -30- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767
[0090] 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).
[0091] Unless otherwise indicated, ratios, percentages, parts, and the like are by weight.
[0092] 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. EXAMPLES General Information
[0093] The IUPAC names and abbreviations of the compounds tested herein are provided below. -31- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 Example 1. Synthesis of Renewable Biobased 3-Amino-3-methyl-2-butanol Synthesis of renewable 2-nitropropane (2NP).
[0094] Titanium silicalite-1 (5.0 g, TS-1, ACS Material), bio-based acetone (29 g, 0.5 mol, MilliporeSigma), and 10% aqueous ammonia (170.3 g, 1.0 mol) were charged into a 3-neck flask equipped with a condenser. The mixture was heated to 60 to 65 °C and then 35% aqueous hydrogen peroxide (145.7 g, 1.5 mol) was added dropwise over a 2-hour period while maintaining the internal temperature of the reaction mixture below 70 °C. After addition of hydrogen peroxide, the mixture was kept at 65 °C for 2-4 hours until all intermediate oxime reacted according to GC. The reaction mixture was cooled to room temperature and filtered. 2NP was separated from the aqueous layer using a separatory funnel and then dried using anhydrous sodium sulfate. The isolated yield of 2NP was 75% with purity of 97%. -32- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 Synthesis of renewable 3-nitro-3-methyl-2-butanol (NMB) and renewable 3-amino-3-methyl- 2-butanol (AMB).
[0095] 2-Nitropropane (1 mol, 97%, from previous step) 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 ambient temperature overnight. GC-FID analysis indicated 91% conversion of 2NP to NMB. The reaction mixture was then fed into a stainless steel reactor containing Raney Nickel (10 wt%) and methanol with 650 psi hydrogen at 50-80 °C. Upon complete reaction, the mixture was separated from the catalyst and distilled at ambient pressure. The fraction containing the desired product was collected at 158-162 °C and recovered as a colorless liquid. The isolated yield was 70% and the purity was 96% 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 μm film thickness; carrier gas flow rate: 1 mL / min helium; gas chromatograph: Agilent model 7890, Series II). Example 2. Purification and Dilution of 3-Amino-3-methyl-2-butanol
[0096] A portion of the product from Example 1 was crystallized from diethyl ether to provide a purity of 99.6%. Dilutions were prepared by mixing AMB with deionized water at 40 °C. The resulting solutions were cooled until the samples solidified. Table 1 below shows melting point data for AMB samples at different purity levels and dilutions. Sample 1 is the distilled product from Example 1. Sample 2 is Sample 1 plus water. Sample 3 is the crystallized form of the product from Example 1. Sample 4 is Sample 3 plus water. Higher levels of impurities and water provided lower melting points. Table 1. Properties of 3-amino-3-methyl-2-butanol at different purities and moisture content -33- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767
[0097] The isolated product may be diluted with water to 90% activity by weight to improve stability. Example 3. Preparation and Performance of Hair Styling Aerosols Containing 3- Amino-3-methyl-2-butanol
[0098] Hair styling formulations of Table 2 were prepared in accordance with the following protocol: 1. Measured the desired amount of solvents: ethanol or ethanol and water. 2. Added the fixative polymer. 3. Added neutralizer based on acidity and desired neutralization level of the polymer, mixed well. 4. Charged desired amount of above concentrate in an aerosol can, charged with propellant.
[0099] Composition A was non-aqueous, whereas composition B contained water as well. Table 2. Exemplary formulations for hair styling aerosols. -34- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 *Blend of isobutane and propane. **1,1-Difluoroethane.
[0100] High humidity curl retention was measured at various timepoints for up to 24 hours. The high humidity curl retention ability was tested for each exemplary formulation from Table 2 using the following protocol: 1. Prepared the desired concentration of polymer solution in ethanol. 2. Neutralized to 100% using the neutralizer under consideration. 3. Prepared hair tresses for testing. Used newly washed / conditioned tresses. 4. Applied and combed through 0.8 grams of neutralized polymer solution to tress to evenly distribute polymer solution. 5. Curled hair onto curling rod securing the curls. 6. Dried curls at 55°C for 15 minutes in an explosion-proof oven. 7. Ensured that curls were thoroughly dried. 8. Removed and hung curls. 9. Noted the length of curls over time under 90% RH at 30°C.
[0101] FIG.1 indicates that the formulation with AMB performed similarly to that with AMP and significantly better than those with TEA and TIPA to retain curls over time. Example 4. Performance of Hair Styling Gels Comprising 3-amino-3-methyl-2-butanol
[0102] Hair styling gels of Table 3 were prepared using the following protocol: 1. Measured the desired amount of water, added preservative 2. Added Acudyne or other polymer, mixed well 3. Added the rheology modifier - Aculyn 88 4. Added neutralizer while monitoring pH, continued to the desired pH of 7.0-7.5 5. If needed, QS with water -35- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 Table 3. Exemplary formulations for hair styling gels using various neutralizing agents. * Soft / hard polymer in emulsion particles including acrylates / hydroxyesters acrylates copolymer. ** A thickener / rheology modifier containing acrylates / steareth-20 methacrylate crosspolymer. *** A cosmetic preservative including 90 wt% phenoxyethanol and 10 wt% ethylhexylglycerin.
[0103] Compositions C and E are comparative; composition D contained AMB in accordance with the present technology. FIG.2 indicated that 3-amino-3-methyl-2-butanol performed similarly to 2-amino-2-methyl-1-propanol and significantly better than triethanolamine. Example 5. Hand Sanitizer Formulations Containing 3-Amino-3-methyl-2-butanol and Performance Properties
[0104] The hand sanitizers of Table 4 were prepared as follows: 1. Measured desired amount of water. -36- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 2. Added the rheology modifier - Carbopol 980 in this case. Mixed well until Carbopol was fully hydrated. 3. Added ethanol. 4. Added neutralizer to pH 7.0-7.2.
[0105] Compositions F, H, I, and K are comparative; compositions G and J contained AMB in accordance with the present technology. Table 4. Exemplary formulations for hand sanitizers using various neutralizing agents with 0.25 wt% or 0.45 wt% Carbopol 980 thickening agent. * Rheology modifier including crosslinked polyacrylic acid.
[0106] The viscosities of the formulations from Table 4 were measured with a Brookfield viscometer, spindle RV4 at 6 rpm. Results are shown in Table 5. -37- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 Table 5. Viscosity in centipoise (cP) of hand sanitizer formulations using various neutralizing agents and 0.25 wt% Carbopol 980 (F, G, H) and 0.45 wt% Carbopol 980 (I, J, K).
[0107] Table 4 indicates that formulations comprising 3-amino-3-methyl-2-butanol resulted in similar viscosity to formulations comprising 2-amino-2-methyl-1-propanol and significantly higher viscosity than formulations comprising triethanolamine.
[0108] FIGS.3A and 3B indicated that formulations comprising 3-amino-3-methyl-2-butanol with 0.25 wt% (4A) and 0.45 wt% (4B) Carbopol 980 provided similar clarity to formulations comprising 2-amino-2-methyl-1-propanol and significantly better clarity than formulations comprising triethanolamine. Turbidity measurements for these formulations were obtained using an Orion™ AQUAfast AQ3010 Turbidity Meter and are set forth in Table 5 as well. Example 6. Preparation and Performance of Sunscreen Formulation Containing 3- Amino-3-methyl-2-butanol
[0109] The five sunscreen formulations of Table 6 were prepared using the following protocol: 1. Heat phase to 75°C, mix well 2. Premix phase B, and add to A while mixing at 300 rpm and heating at 75°C -38- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 3. Separately heat phase C to 75°C 4. Add C to A and B, mix using a speed mixer at 2000 rpm for 1 min
[0110] Compositions L-O are comparative; composition P contained AMB. Table 6. Sunscreen Formulations
[0111] SPF was measured for each formulation according to the ISO 24443: 2021 standard, specific for determining the “SPF” sun protection index. Briefly, a quantity of 30 mg of the sunscreen to be tested was applied to sandblasted polymethacrylate (PMMA) plates with specific area to arrive at a dosage of 1.2 mg / cm². The samples to be tested were applied to the rough phase of the plate using a bare finger pre-saturated with product in order to obtain the most homogeneous film possible. A series of 16 measurements was then carried out -39- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 using a UV-2600240V IVDD spectrophotometer (manufacturer: SHIMADZU) or Lambda 1050+ (manufacturer: PERKINELMER) equipped with an integrating sphere between 290 and 400 nm. An average of the absorbance of the measurements was then calculated, thus making it possible to obtain the sun photoprotection indices SPF, UVA, and LOC. Results are shown in FIG.4. Results indicated the AMB-containing formulation provided the highest SPF rating of any formulation tested. EQUIVALENTS
[0112] 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.
[0113] 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.
[0114] The embodiments, illustratively described herein may suitably be practiced in the absence of any element or elements, limitation or limitations, not specifically disclosed -40- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 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.
[0115] 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.
[0116] 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.
[0117] All publications, patent applications, issued patents, and other documents (for example, journals, 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 -41- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 in its entirety. Definitions that are contained in text incorporated by reference are excluded to the extent that they contradict definitions in this disclosure.
[0118] 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: A. A composition comprising: a molecule comprising an acid group; 3-amino-3-methyl-2-butanol; and a solvent, optionally wherein the solvent comprises water and / or an alcohol. B. The composition of Paragraph A, comprising an amount of 3-amino-3-methyl-2-butanol effective to partially or completely neutralize the molecule. C. The composition of Paragraph A, wherein the composition comprises about 0.001 wt% to about 40 wt% of the molecule comprising the acid group. D. The composition of any one of the preceding Paragraphs, wherein the composition comprises about 0.01 wt% to about 40 wt% of the molecule comprising the acid group. E. The composition of any one of the preceding Paragraphs, wherein the composition comprises about 0.05 wt% to about 15 wt% of the molecule comprising the acid group. F. The composition of any one of the preceding Paragraphs, wherein the composition comprises about 0.1 wt% to about 5 wt% of the molecule comprising the acid group. G. The composition of any one of the preceding Paragraphs, wherein the composition comprises about 10 wt% to about 30 wt% of the molecule comprising the acid group. -42- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 H. The composition of any one of the preceding Paragraphs, wherein the acid group of the molecule comprising the acid group is selected from the group consisting of carboxylic acid, sulfonic acid, phosphonic acid, or phosphoric acid group. I. The composition of claim any one of the preceding Paragraphs, comprising multiple molecules comprising acid groups, each molecule having an acid gorup independently selected from the group consisting of carboxylic acid, sulfonic acid, phosphonic acid, or phosphoric acid, or a combination of two or more thereof. J. The composition of claim any one of the preceding Paragraphs, wherein the molecule comprising the acid group is a carboxylic acid. K. The composition of Paragraph A, wherein the molecule comprising the acid group is a polymer comprising acid groups. L. The composition of Paragraph K, wherein the polymer is present at an amount of about 0.05 wt% to about 40 wt% of the total weight of the composition. M. The composition of Paragraph K or Paragraph L, wherein the polymer is present at an amount of about 0.1 wt% to about 15 wt% of the total weight of the composition. N. The composition of any one of Paragraphs K-M0, wherein the polymer is present at an amount of about 0.1 wt% to about 5 wt% of the total weight of the composition. O. The composition of Paragraph K or Paragraph L, wherein the polymer is present at an amount of about 10 wt% to about 30 wt% of the total weight of the composition. P. The composition of any one of Paragraphs K-O0, wherein the acid groups of the polymer are selected from the group consisting of carboxyl groups, sulfonyl groups, phosphonyl groups, phosphoryl groups, or a combination of two or more thereof. Q. The composition of any one of Paragraphs K-P0, wherein the acid groups of the polymer comprise carboxyl groups. -43- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 R. The composition of any one of Paragraphs K-Q0, wherein the polymer is selected from the group consisting of polyacrylate copolymers, vinyl acetate copolymer, or combinations thereof. S. The composition of any one of Paragraphs K-R0, wherein the polymer is selected from the group consisting of cross-linked polyacrylic acid; ethyl acrylate, methyl methacrylate and methacrylic acid copolymer; ethyl acrylate, t-butyl acrylate and methacrylic acid copolymer; octyl acrylamide, acrylates and butylaminoethyl methacrylate copolymer; methacrylic acid, n-butyl acrylate and methyl methacrylate copolymer; methacrylic acid, n-butyl acrylate and ethyl methacrylate copolymer; butyl acrylate, methyl methacrylate, hydroxyethyl methacrylate and methacrylic acid copolymer; vinyl acetate, crotonates and vinyl neodecanoate copolymer; a butyl ester of vinyl methyl ether and maleic anhydride copolymer; an ethyl ester of vinyl methyl ether and maleic anhydride copolymer; vinyl acetate and vinylpyrrollidone copolymer; acrylates / steareth-20 methacrylate crosspolymer; hyaluronic acid; carbomers; and mixtures of any two or more thereof. T. The composition of any one of Paragraphs K-S, wherein the polymer has a weight average molecular weight of about 10 to about 1000 kDa. U. The composition of any one of Paragraphs K-T, wherein the polymer is cross-linked. V. The composition of any one of the preceding Paragraphs, wherein 3-amino-3-methyl-2- butanol is present in an amount of about 0.005 wt% to about 10 wt% of the total weight of the composition. W. The composition of any one of the preceding Paragraphs, wherein 3-amino-3-methyl-2- butanol is present in an amount of about 0.02 wt% to about 2 wt% of the total weight of the composition. X. The composition of any one of the preceding Paragraphs, further comprising one or more additives selected from a preservative, thickener, water-miscible co-solvent, water immiscible co-solvent, anti-microbial, non-ionic polymer, dye, fragrance, and corrosion inhibitors. -44- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 Y. The composition of any one of the preceding Paragraphs, further comprising an anionic and / or zwitterionic surfactant. Z. The composition of Paragraph Y, wherein the anionic and / or zwitterionic surfactant is selected from the group consisting of fatty acids, alkyl sulfates, alkyl(oxyalkyl)(n) sulfates where n is the average degree of alkoxylation from 1 to 3, alkyl sulfonates, alkenyl sulfonates, alkylamidealkylbetaines, and combinations of two or more thereof. AA. The composition of Paragraph Y or Paragraph Z, wherein the anionic and / or zwitterionic surfactant is selected from the group consisting of sodium lauryl sulfate, ammonium lauryl sulfate, sodium or ammonium laureth(n) sulfate where n is the average degree of ethoxylation from 1 to 3, alkoxyalkylsodium lauryl sulfate, sodium laureth sulfate, cocamidopropyl betaine, and combinations of two or more thereof. AB. The composition of any one of Paragraphs Y-AA, comprising about 1 wt% to about 50 wt% of the anionic and / or zwitterionic surfactant. AC. The composition of any one of Paragraphs Y-AB, comprising about 5 wt% to about 40 wt% of the anionic and / or zwitterionic surfactant. AD. The composition of any one of Paragraphs K-AC, further comprising an alcohol selected from ethanol, n-propanol, isopropanol, or combination of two or more thereof. AE. The composition of Paragraph AD, comprising about 40 wt% to about 95 wt% of the alcohol. AF. The composition of Paragraph AD or Paragraph AE, comprising about 60 wt% to about 70 wt% of the alcohol. AG. The composition of any one of Paragraphs AD to AF, comprising about 0.1 wt% to about 1 wt% polymer and about 0.02 wt% to about 0.3 wt% 3-amino-3-methyl-2- butanol. -45- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 AH. The composition of any one of Paragraphs K-AG, further comprising acrylates / steareth- 20 methacrylate crosspolymer thickener and wherein the polymer is an acrylates / hydroxyesters acrylates copolymer. AI. The composition of Paragraph AH, comprising about 0.5 wt% to about 4 wt% of the polymer, about 0.1 wt% to about 1 wt% 3-amino-3-methyl-2-butanol, and about 1 wt% to about 10 wt% thickener. AJ. The composition of any one of Paragraphs K-AI, comprising about 2 wt% to about 15 wt% of the polymer and about 0.4 to about 3 wt% 3-amino-3-methyl-2-butanol, and wherein the polymer is an acrylates / hydroxyesters acrylates copolymer. AK. The composition of Paragraph AJ, further comprising a propellant. AL. The composition of Paragraph AK, wherein the propellant is selected from the group consisting of methyl acetate, dimethyl ether, propane, n-butane, isobutane, and mixtures of two or more thereof. AM. The composition of any one of Paragraphs AJ-AL further comprising about 10 wt% to about 90 wt% ethanol. AN. The composition of any one of the preceding Paragraphs, wherein the composition comprises about 40 wt% to about 60 wt % water and has a pH of about 6 to about 8. AO. The composition of any one of Paragraph K-AI, further comprising about 2 wt% to about 75 wt% pigment. AP. The composition of Paragraph AO, wherein the pigment comprises titanium dioxide, zinc oxide, or a combination thereof. AQ. The composition of Paragraph AO or Paragraph AP comprising about 2 wt% to about 15 wt% of the polymer and about 0.02 wt% to about 2 wt% 3-amino-3-methyl-2- butanol. AR. The composition of any one of the preceding Paragraphs, wherein the composition further comprises an amino alcohol other than 3-amino-3-methyl-2-butanol. -46- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 AS. The composition of the preceding Paragraphs, wherein the amino alcohol is 2- aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2- amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2- ol, or a combination of any two or more thereof. AT. The composition of Paragraph AR or Paragraph AS, wherein the composition comprises at least about 0.01 wt% of the amino alcohol. AU. The composition of any one of Paragraphs AR-AT, wherein the composition comprises 3-(ethylamino)-3-methylbutan-2-ol in addition to 3-amino-3-methyl-2-butanol. AV. The composition of any one of the preceding Paragraphs, wherein the composition exhibits a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24. AW. The composition of any one of the preceding Paragraphs, wherein the composition comprises about 0.001 wt% to about 0.5 wt% secondary amines. AX. The composition of any one of the preceding Paragraphs, wherein the composition is a hair styling aerosol, a body lotion, a mascara, a hair colorant, a sunscreen, a hand sanitizer, a cleanser, an eye cream, an exfoliant, a shampoo, a conditioner, a hair mask, a hair styling gel, a hair styling mousse, a dry shampoo, a non-aerosol hair styling spray, a body wash, a soap, a body scrub, a body butter, a lipstick, a foundation, an eye shadow, a concealer, a blush, an eyeliner, a brow gel, a lip gloss, a lip balm, a setting spray, or a shaving cream. AY. A method of making a composition of any one of Paragraphs A-J, the method comprising combining 3-amino-3-methyl-2-butanol with a purity of at least 95 wt% and the molecule comprising the acid group, with sufficient water to provide the composition. AZ. The method of Paragraph AY, wherein the method further comprises mixing the combined 3-amino-3-methyl-2-butanol, the molecule comprising the acid group, and water until a homogenous solution is obtained. -47- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 BA. A composition for use in personal care products, the composition comprising about 30 wt% to about 99.99 wt% 3-amino-3-methyl-2-butanol; about 0.01 wt% to about 70 wt% water; and optionally an amino alcohol other than 3-amino-3-methyl-2-butanol (an “other amino alcohol”). BB. The composition for use of Paragraph BA, wherein the composition is for use in hair styling aerosols, body lotions, mascara, hair colorants, sunscreens, hand sanitizers, cleansers, eye creams, exfoliants, shampoos, conditioners, hair masks, hair styling gels, hair styling mousse, dry shampoos, non-aerosol hair styling sprays, body washes, soaps, body scrubs, body butters, lipsticks, foundations, eye shadows, concealers, blushes, eyeliners, brow gels, lip glosses, lip balms, setting sprays, and / or shaving creams. BC. The composition for use of Paragraph BA or Paragraph BB, the composition comprising about 0.01 wt% to about 60 wt% of the other amino alcohol. BD. The composition for use of Paragraph BC, comprising not more than 1 wt% of the other amino alcohol. BE. The composition for use of any one of Paragraphs BA-BD, comprising about 70 wt% to about 95 wt% 3-amino-3-methyl-2-butanol and about 5 wt% to about 30 wt% water. BF. The composition for use of any one of Paragraphs BA-BE, comprising about 90 wt% 3- amino-3-methyl-2-butanol, about 10 wt% water, and less than 1 wt% of the other amino alcohol. BG. The composition for use of any one of Paragraphs BA-BF, wherein the composition comprises less than 2 wt% secondary amine. BH. The composition for use of any one of Paragraphs BA-BG, wherein the composition further comprises not more than 5 wt% of the other amino alcohol. BI. The composition for use of any one of Paragraphs BA-BH, wherein the composition further comprises not more than 0.5 wt% of the other amino alcohol. -48- 4882-7047-2420.1 Atty. Dkt. No.: 109691-0767 BJ. The composition for use of any one of Paragraphs BA-BI, wherein the other amino alcohol is 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl- 1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3- methylbutan-2-ol, or a combination of any two or more thereof. BK. The composition for use of any one of Paragraphs BA-BJ, wherein the composition comprises at least about 0.01 wt% of the other amino alcohol. BL. The composition for use of any one of Paragraphs BA-BK, wherein the composition comprises 3-(ethylamino)-3-methylbutan-2-ol in addition to 3-amino-3-methyl-2- butanol. BM. The composition for use of any one of Paragraphs BA-BL, wherein the composition exhibits a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
[0119] Other embodiments are set forth in the following claims, along with the full scope of equivalents to which such claims are entitled. -49- 4882-7047-2420.1
Claims
Atty. Dkt. No.: 109691-0767 WHAT IS CLAIMED IS:
1. A composition comprising: a molecule comprising an acid group; 3-amino-3-methyl-2-butanol; and a solvent, optionally wherein the solvent comprises water and / or an alcohol.
2. The composition of Claim 1, comprising an amount of 3-amino-3-methyl-2-butanol effective to partially or completely neutralize the molecule.
3. The composition of Claim 1, wherein the composition comprises about 0.001 wt% to about 40 wt% of the molecule comprising the acid group.
4. The composition of Claim 1, wherein the composition comprises about 0.01 wt% to about 40 wt% of the molecule comprising the acid group.
5. The composition of Claim 1, wherein the composition comprises about 0.05 wt% to about 15 wt% of the molecule comprising the acid group.
6. The composition of Claim 1, wherein the composition comprises about 0.1 wt% to about 5 wt% of the molecule comprising the acid group.
7. The composition of Claim 1, wherein the composition comprises about 10 wt% to about 30 wt% of the molecule comprising the acid group.
8. The composition of Claim 1, wherein the acid group of the molecule comprising the acid group is selected from the group consisting of carboxylic acid, sulfonic acid, phosphonic acid, or phosphoric acid group.
9. The composition of Claim 1, comprising multiple molecules comprising acid groups, each molecule having an acid group independently selected from the group consisting of carboxylic acid, sulfonic acid, phosphonic acid, or phosphoric acid, or a combination of two or more thereof. -50- 4882-7047-2420.1Atty. Dkt. No.: 109691-0767 10. The composition of Claim 1, wherein the molecule comprising the acid group is a carboxylic acid.
11. The composition of Claim 1, wherein the molecule comprising the acid group is a polymer comprising acid groups.
12. The composition of Claim 11, wherein the polymer is present at an amount of about 0.05 wt% to about 40 wt% of the total weight of the composition.
13. The composition of Claim 11, wherein the polymer is present at an amount of about 0.1 wt% to about 15 wt% of the total weight of the composition.
14. The composition of Claim 11, wherein the polymer is present at an amount of about 0.1 wt% to about 5 wt% of the total weight of the composition.
15. The composition of Claim 11, wherein the polymer is present at an amount of about 10 wt% to about 30 wt% of the total weight of the composition.
16. The composition of Claim 11, wherein the acid groups of the polymer are selected from the group consisting of carboxyl groups, sulfonyl groups, phosphonyl groups, phosphoryl groups, or a combination of two or more thereof.
17. The composition of Claim 11, wherein the acid groups of the polymer comprise carboxyl groups.
18. The composition of Claim 11, wherein the polymer is selected from the group consisting of polyacrylate copolymers, vinyl acetate copolymer, or combinations thereof.
19. The composition of Claim 11, wherein the polymer is selected from the group consisting of cross-linked polyacrylic acid; ethyl acrylate, methyl methacrylate and methacrylic acid copolymer; ethyl acrylate, t-butyl acrylate and methacrylic acid copolymer; octyl acrylamide, acrylates and butylaminoethyl methacrylate copolymer; methacrylic acid, n-butyl acrylate and methyl methacrylate copolymer; methacrylic acid, n-butyl acrylate and ethyl methacrylate copolymer; butyl acrylate, methyl methacrylate, hydroxyethyl methacrylate and methacrylic acid copolymer; vinyl acetate, crotonates -51- 4882-7047-2420.1Atty. Dkt. No.: 109691-0767 and vinyl neodecanoate copolymer; a butyl ester of vinyl methyl ether and maleic anhydride copolymer; an ethyl ester of vinyl methyl ether and maleic anhydride copolymer; vinyl acetate and vinylpyrrollidone copolymer; acrylates / steareth-20 methacrylate crosspolymer; hyaluronic acid; carbomers; and mixtures of any two or more thereof.
20. The composition of Claim 11, wherein the polymer has a weight average molecular weight of about 10 to about 1000 kDa.
21. The composition of Claim 11, wherein the polymer is cross-linked.
22. The composition of Claim 1, wherein 3-amino-3-methyl-2-butanol is present in an amount of about 0.005 wt% to about 10 wt% of the total weight of the composition.
23. The composition of Claim 1, wherein 3-amino-3-methyl-2-butanol is present in an amount of about 0.02 wt% to about 2 wt% of the total weight of the composition.
24. The composition of Claim 1, further comprising one or more additives selected from a preservative, thickener, water-miscible co-solvent, water immiscible co-solvent, anti- microbial, non-ionic polymer, dye, fragrance, and corrosion inhibitors.
25. The composition of Claim 1, further comprising an anionic and / or zwitterionic surfactant.
26. The composition of Claim 25, wherein the anionic and / or zwitterionic surfactant is selected from the group consisting of fatty acids, alkyl sulfates, alkyl(oxyalkyl)(n) sulfates where n is the average degree of alkoxylation from 1 to 3, alkyl sulfonates, alkenyl sulfonates, alkylamidealkylbetaines, and combinations of two or more thereof.
27. The composition of Claim 25, wherein the anionic and / or zwitterionic surfactant is selected from the group consisting of sodium lauryl sulfate, ammonium lauryl sulfate, sodium or ammonium laureth(n) sulfate where n is the average degree of ethoxylation from 1 to 3, alkoxyalkylsodium lauryl sulfate, sodium laureth sulfate, cocamidopropyl betaine, and combinations of two or more thereof. -52- 4882-7047-2420.1Atty. Dkt. No.: 109691-0767 28. The composition of Claim 25, comprising about 1 wt% to about 50 wt% of the anionic and / or zwitterionic surfactant.
29. The composition of Claim 25, comprising about 5 wt% to about 40 wt% of the anionic and / or zwitterionic surfactant.
30. The composition of Claim 11, further comprising an alcohol selected from ethanol, n- propanol, isopropanol, or combination of two or more thereof.
31. The composition of Claim 30, comprising about 40 wt% to about 95 wt% of the alcohol.
32. The composition of Claim 30, comprising about 60 wt% to about 70 wt% of the alcohol.
33. The composition of Claim 30, comprising about 0.1 wt% to about 1 wt% polymer and about 0.02 wt% to about 0.3 wt% 3-amino-3-methyl-2-butanol.
34. The composition of Claim 11, further comprising acrylates / steareth-20 methacrylate crosspolymer thickener and wherein the polymer is an acrylates / hydroxyesters acrylates copolymer.
35. The composition of Claim 34, comprising about 0.5 wt% to about 4 wt% of the polymer, about 0.1 wt% to about 1 wt% 3-amino-3-methyl-2-butanol, and about 1 wt% to about 10 wt% thickener.
36. The composition of Claim 11, comprising about 2 wt% to about 15 wt% of the polymer and about 0.4 to about 3 wt% 3-amino-3-methyl-2-butanol, and wherein the polymer is an acrylates / hydroxyesters acrylates copolymer.
37. The composition of Claim 36, further comprising a propellant.
38. The composition of Claim 37, wherein the propellant is selected from the group consisting of methyl acetate, dimethyl ether, propane, n-butane, isobutane, and mixtures of two or more thereof.
39. The composition of Claim 36, further comprising about 10 wt% to about 90 wt% ethanol. -53- 4882-7047-2420.1Atty. Dkt. No.: 109691-0767 40. The composition of Claim 1, wherein the composition comprises about 40 wt% to about 60 wt % water and has a pH of about 6 to about 8.
41. The composition of Claim 11, further comprising about 2 wt% to about 75 wt% pigment.
42. The composition of Claim 41, wherein the pigment comprises titanium dioxide, zinc oxide, or a combination thereof.
43. The composition of Claim 41, comprising about 2 wt% to about 15 wt% of the polymer and about 0.02 wt% to about 2 wt% 3-amino-3-methyl-2-butanol.
44. The composition of Claim 1, wherein the composition further comprises an amino alcohol other than 3-amino-3-methyl-2-butanol.
45. The composition of Claim 44, wherein the amino alcohol is 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1- butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2-ol, or a combination of any two or more thereof.
46. The composition of Claim 44, wherein the composition comprises at least about 0.01 wt% of the amino alcohol.
47. The composition of Claim 44, wherein the composition comprises 3-(ethylamino)-3- methylbutan-2-ol in addition to 3-amino-3-methyl-2-butanol.
48. The composition of Claim 1, wherein the composition exhibits a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
49. The composition of Claim 1, wherein the composition comprises about 0.001 wt% to about 0.5 wt% secondary amines.
50. The composition of Claim 1, wherein the composition is a hair styling aerosol, a body lotion, a mascara, a hair colorant, a sunscreen, a hand sanitizer, a cleanser, an eye cream, an exfoliant, a shampoo, a conditioner, a hair mask, a hair styling gel, a hair styling mousse, a dry shampoo, a non-aerosol hair styling spray, a body wash, a soap, -54- 4882-7047-2420.1Atty. Dkt. No.: 109691-0767 a body scrub, a body butter, a lipstick, a brow gel, a foundation, a concealer, a blush, an eye shadow, an eyeliner, a lip gloss, a lip balm, a setting spray, or a shaving cream.
51. A method of making a composition of Claim 1, the method comprising combining 3- amino-3-methyl-2-butanol with a purity of at least 95 wt% and the molecule comprising the acid group, with sufficient water to provide the composition.
52. The method of Claim 50, wherein the method further comprises mixing the combined 3- amino-3-methyl-2-butanol, the molecule comprising the acid group, and water until a homogenous solution is obtained.
53. A composition for use in personal care products, the composition comprising about 50 wt% to about 99.99 wt% 3-amino-3-methyl-2-butanol; about 0.01 wt% to about 50 wt% water; and optionally an amino alcohol other than 3-amino-3-methyl-2-butanol (an “other amino alcohol”).
54. The composition for use of Claim 53, wherein the composition is for use in hair styling aerosols, body lotions, mascara, hair colorants, sunscreens, hand sanitizers, cleansers, eye creams, exfoliants, shampoos, conditioners, hair masks, hair styling gels, hair styling mousse, dry shampoos, non-aerosol hair styling sprays, body washes, soaps, body scrubs, body butters, lipsticks, foundations, eye shadows, concealers, blushes, eyeliners, brow gels, lip glosses, lip balms, setting sprays, and / or shaving creams.
55. The composition for use of Claim 53, the composition comprising about 0.01 wt% to about 60 wt% of the other amino alcohol.
56. The composition for use of Claim 55, comprising not more than 1 wt% of the other amino alcohol.
57. The composition for use of Claim 53, comprising about 70 wt% to about 95 wt% 3- amino-3-methyl-2-butanol and about 5 wt% to about 30 wt% water.
58. The composition for use of Claim 53, comprising about 90 wt% 3-amino-3-methyl-2- butanol, about 10 wt% water, and less than 1 wt% of the other amino alcohol. -55- 4882-7047-2420.1Atty. Dkt. No.: 109691-0767 59. The composition for use of Claim 53, wherein the composition comprises less than 2 wt% secondary amine.
60. The composition for use of Claim 53, wherein the composition further comprises not more than 5 wt% of the other amino alcohol.
61. The composition for use of Claim 53, wherein the composition further comprises not more than 0.5 wt% of the other amino alcohol.
62. The composition for use of Claim 61, wherein the other amino alcohol is 2- aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2- amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2- ol, or a combination of any two or more thereof.
63. The composition for use of Claim 61, wherein the composition comprises at least about 0.01 wt% of the other amino alcohol.
64. The composition for use of Claim 61, wherein the composition comprises 3- (ethylamino)-3-methylbutan-2-ol in addition to 3-amino-3-methyl-2-butanol.
65. The composition for use of Claim 53, wherein the composition exhibits a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24. -56- 4882-7047-2420.1