Branched amino acid surfactants

Patent metadata

Field	Value
Publication number	US-11897834-B2
Application number	US-202117365770-A
Country	US
Kind code	B2
Filing date	Jul 1, 2021
Priority date	Jul 9, 2020
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

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.

First claim

The invention claimed is:

1. A compound of the following formula:

wherein R 1 is selected from the group consisting of hydrogen, an oxygen atom, and a substituted or unsubstituted C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates;
n is an integer from 2 to 5;
R 2 is C 5 or C 6 alkyl;
R 3 is C 3 or C 4 alkyl;
the terminal nitrogen is optionally further substituted with R 4 , wherein R 4 chosen from hydrogen, an oxygen atom, and a substituted or unsubstituted C 1 -C 6 alkyl, wherein the substituted C 1 -C 6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates;
and if R 4 is present then the compound comprises a counterion selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate.

2. 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:

3. The compound of claim 2 , having a critical micelle concentration (CMC) of about 21.30 mmol in water.

4. 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:

5. The compound of claim 4 , having a critical micelle concentration (CMC) of about 0.97 mmol in water.

6. 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.

7. 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:

8. The compound of claim 7 , having a critical micelle concentration (CMC) of about 27.47 mmol in water.

9. The compound of claim 1 , wherein the compound is 4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

10. The compound of claim 9 , having a critical micelle concentration (CMC) of about 0.54 mmol in water.

11. 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.

12. The compound of claim 1 , wherein the compound is 2-butyloctyl6-(dimethylamino)hexanoate N-oxide, having the following formula:

13. The compound of claim 12 , having a critical micelle concentration (CMC) of about 0.29 mmol in water.

14. 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.

15. A compound of the following formula:

wherein le is selected from the group consisting of an oxygen atom, and a substituted or unsubstituted C 1 -C 6 alkyl, wherein the substituted C 1 -C 6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates;
n is an integer from 2 to 5;
R 2 is C 5 -C 12 alkyl;
R 3 is C 3 -C 10 alkyl;
the terminal nitrogen is optionally further substituted with R 4 , wherein R 4 chosen from an oxygen atom, and a substituted or unsubstituted C 1 -C 6 alkyl, wherein the substituted C 1 -C 6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates;
and if R 4 is present then the compound comprises a counterion selected from the group consisting of chloride, bromide and iodide.

16. A liquid composition comprising:
a medium; and
a surfactant of the following formula:

wherein R 1 is selected from the group consisting of hydrogen, an oxygen atom, and a substituted or unsubstituted C 1 -C 6 alkyl, wherein the substituted C 1 -C 6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates;
n is an integer from 2 to 5;
R 2 is C 5 or C 6 alkyl;
R 3 is C 3 or C 4 alkyl;
the terminal nitrogen is optionally further substituted with R 4 , wherein R 4 chosen from hydrogen, an oxygen atom, and a substituted or unsubstituted C 1 -C 6 alkyl, wherein the substituted C 1 -C 6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates;
and if R 4 is present then the compound comprises a counterion selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate.

17. The composition of claim 16 , wherein the medium is water.

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 C 1 -C 6 alkyl, wherein the substituted C 1 -C 6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates;
n is an integer from 2 to 5;
R 2 is C 5 or C 6 alkyl;
R 3 is C 3 or C 4 alkyl;
the terminal nitrogen is optionally further substituted with R 4 , wherein R 4 chosen from an oxygen atom, and a substituted or unsubstituted C 1 -C 6 alkyl, wherein the substituted C 1 -C 6 alkyl comprises a group selected from the group consisting of carboxylates, hydroxyls, sulfonyls, or sulfonates;
and if R 4 is present then the compound comprises a counterion selected from the group consisting of chloride, bromide and iodide.

19. The composition of claim 18 , wherein the medium is water.

Assignees

• Advansix Resins & Chemicals Llc

Inventors

• Asirvatham Edward
• Honciuc Andrei
• MIHALI Voichita

Classifications

• C07C309/22 Primary

  containing carboxyl groups bound to the carbon skeleton · CPC title

• C07C229/08 Primary

  the nitrogen atom of the amino group being further bound to hydrogen atoms · CPC title

• C07C229/12

  to carbon atoms of acyclic carbon skeletons · CPC title

• C09K23/00

  Use of substances as emulsifying, wetting, dispersing, or foam-producing agents · CPC title

• C07C309/30 Primary

  of six-membered aromatic rings substituted by alkyl groups · CPC title