# US 11,897,834 B2 · Branched amino acid surfactants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,897,834 B2 - Document ID: US11897834B2 - Status: Granted - Kind: B2 - Application number: 17/365,770 - Filed: 2021-07-01 - Published: 2022-01-13 - Granted: 2024-02-13 - Earliest claimed: 2020-07-09 - Assignees: AdvanSix Resins & Chemicals LLC - Applicants: AdvanSix Resins & Chemicals LLC - Inventors: Edward Asirvatham; Andrei Honciuc; Voichita Mihali - Web page: https://patentgrep.com/patent/US11897834B2 ## CPC - C07C 309/22: containing carboxyl groups bound to the carbon skeleton - C07C 309/30: of six-membered aromatic rings substituted by alkyl groups - C07C 229/08: the nitrogen atom of the amino group being further bound to hydrogen atoms - C07C 229/12: to carbon atoms of acyclic carbon skeletons - C07C 291/04: containing amino-oxide bonds - C07C 309/14: containing amino groups bound to the carbon skeleton - C11D 1/46: Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols - C11D 1/75: Amino oxides - C11D 1/92: Sulfobetaines {; Sulfitobetaines} - C09K 23/00: Use of substances as emulsifying, wetting, dispersing, or foam-producing agents - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract The present disclosure provides derivatives of amino acids that have branched alkyl structures and surface-active properties. The amino acid can be naturally-occurring or synthetic, or they may be obtained via a ring-opening reaction of a lactam, such as caprolactam. The amino acid may be functionalized to form a compound that is surface-active and have advantageous surfactant characteristics. The compounds of the present disclosure have low critical micelle concentrations (CMC) as well as superior ability to lower the surface tension of a liquid. ## Claims ### Claim 1 A compound of the following formula: wherein R1 is selected from the group consisting of hydrogen, an oxygen atom, and a substituted or unsubstituted C1-C6 alkyl, wherein the C1-C6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates; n is an integer from 2 to 5; R2 is C5 or C6 alkyl; R3 is C3 or C4 alkyl; the terminal nitrogen is optionally further substituted with R4, wherein R4 chosen from hydrogen, an oxygen atom, and a substituted or unsubstituted C1-C6 alkyl, wherein the substituted C1-C6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates; and if R4 is present then the compound comprises a counterion selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate. ### Claim 2 (depends on 1) The compound of claim 1, wherein the compound is 6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula: ### Claim 3 (depends on 2) The compound of claim 2, having a critical micelle concentration (CMC) of about 21.30 mmol in water. ### Claim 4 (depends on 1) The compound of claim 1, wherein the compound is 6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula: ### Claim 5 (depends on 4) The compound of claim 4, having a critical micelle concentration (CMC) of about 0.97 mmol in water. ### Claim 6 (depends on 4) The compound of claim 4, having a surface tension in water equal to or less than 30 mN/m at a surface age of 100 ms or greater. ### Claim 7 (depends on 1) The compound of claim 1, wherein the compound is 6-((2-butyl octyl)oxy)-N,N-dim ethyl-6-oxohexan-1-aminium chloride, having the following formula: ### Claim 8 (depends on 7) The compound of claim 7, having a critical micelle concentration (CMC) of about 27.47 mmol in water. ### Claim 9 (depends on 1) The compound of claim 1, wherein the compound is 4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula: ### Claim 10 (depends on 9) The compound of claim 9, having a critical micelle concentration (CMC) of about 0.54 mmol in water. ### Claim 11 (depends on 9) The compound of claim 9, having a surface tension in water equal to or less than 36 mN/m at a surface age of 100 ms or greater. ### Claim 12 (depends on 1) The compound of claim 1, wherein the compound is 2-butyloctyl6-(dimethylamino)hexanoate N-oxide, having the following formula: ### Claim 13 (depends on 12) The compound of claim 12, having a critical micelle concentration (CMC) of about 0.29 mmol in water. ### Claim 14 (depends on 12) The compound of claim 12, having a surface tension in water equal to or less than 30 mN/m at a surface age of 1,000 ms or greater. ### Claim 15 A compound of the following formula: wherein le is selected from the group consisting of an oxygen atom, and a substituted or unsubstituted C1-C6 alkyl, wherein the substituted C1-C6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates; n is an integer from 2 to 5; R2 is C5-C12 alkyl; R3 is C3-C10 alkyl; the terminal nitrogen is optionally further substituted with R4, wherein R4 chosen from an oxygen atom, and a substituted or unsubstituted C1-C6 alkyl, wherein the substituted C1-C6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates; and if R4 is present then the compound comprises a counterion selected from the group consisting of chloride, bromide and iodide. ### Claim 16 A liquid composition comprising: a medium; and a surfactant of the following formula: wherein R1 is selected from the group consisting of hydrogen, an oxygen atom, and a substituted or unsubstituted C1-C6 alkyl, wherein the substituted C1-C6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates; n is an integer from 2 to 5; R2 is C5 or C6 alkyl; R3 is C3 or C4 alkyl; the terminal nitrogen is optionally further substituted with R4, wherein R4 chosen from hydrogen, an oxygen atom, and a substituted or unsubstituted C1-C6 alkyl, wherein the substituted C1-C6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates; and if R4 is present then the compound comprises a counterion selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate. ### Claim 17 (depends on 16) The composition of claim 16, wherein the medium is water. ### Claim 18 A liquid composition comprising: a medium; and a surfactant of the following formula: wherein le is selected from the group consisting of an oxygen atom, and a substituted or unsubstituted C1-C6 alkyl, wherein the substituted C1-C6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates; n is an integer from 2 to 5; R2 is C5 or C6 alkyl; R3 is C3 or C4 alkyl; the terminal nitrogen is optionally further substituted with R4, wherein R4 chosen from an oxygen atom, and a substituted or unsubstituted C1-C6 alkyl, wherein the substituted C1-C6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates; and if R4 is present then the compound comprises a counterion selected from the group consisting of chloride, bromide and iodide. ### Claim 19 (depends on 18) The composition of claim 18, wherein the medium is water.