Siloxane derivatives of amino acids having surface-active properties

Patent metadata

Field	Value
Publication number	US-11008348-B2
Application number	US-202016990855-A
Country	US
Kind code	B2
Filing date	Aug 11, 2020
Priority date	Aug 22, 2019
Publication date	May 18, 2021
Grant date	May 18, 2021

Abstract

The present disclosure provides siloxane derivatives of amino acids that have 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 with a siloxane group to form a compound that is surface-active and has surfactant characteristics. The compounds have low critical micelle concentrations (CMC) as well as the ability to lower the surface tension of a liquid.

First claim

The invention claimed is:

1. A compound of Formula I:

wherein R 1 and R 2 may be the same or different, and comprise at least one group selected from the group consisting of C 1 -C 6 alkyl, optionally the C 1 -C 6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
n is an integer from 3 to 12;
the terminal nitrogen is optionally further substituted with R 3 , wherein R 3 is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C 1 -C 6 alkyl; and
an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide.

2. The compound of claim 1 , represented by Formula Ia:

wherein R 1 and R 2 may be the same or different, and comprise at least one group selected from the group consisting of C 1 -C 6 alkyl, optionally the C 1 -C 6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
m is an integer from 3 to 6;
the terminal nitrogen is optionally further substituted with R 3 , wherein R 3 is selected from the group consisting of hydrogen, oxygen, and C 1 -C 6 alkyl wherein the alkyl chain is optionally substituted with one or more substituents selected from the group consisting of carboxyl, carboxylate, and sulfonate; and
an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide.

3. The compound of claim 1 , represented by the following Formula Ib:

wherein R 1 and R 2 may be the same or different, and comprise at least one group selected from the group consisting of C 1 -C 6 alkyl, optionally the C 1 -C 6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
p is 5;
the terminal nitrogen is optionally further substituted with R 3 , wherein R 3 is selected from the group consisting of hydrogen, oxygen, and C 1 -C 6 alkyl, wherein the alkyl chain is optionally substituted with one or more substituents selected from the group consisting of carboxyl, carboxylate, and sulfonate; and
an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide.

4. The compound of claim 1 , wherein R 1 and R 2 are methyl.

5. The compound of claim 1 , wherein n is 5.

6. The compound of claim 5 , wherein R 3 is hydrogen.

7. The compound of claim 6 , wherein the counterion is selected from the group consisting of chloride, bromide, and iodide.

8. The compound of claim 7 , wherein the counterion is chloride.

9. The compound of claim 5 , wherein R 3 is methyl.

10. The compound of claim 9 , wherein the counterion is selected from the group consisting of chloride, bromide, and iodide.

11. The compound of claim 10 , wherein the counterion is iodide.

12. The compound of claim 5 , wherein R 3 is an oxygen atom.

13. The compound of claim 5 , wherein R 3 is C 1 -C 6 alkyl, substituted with sulfonate.

14. The compound of claim 5 , wherein the compound is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethyl silyl)oxy)trisiloxan-3-yl)propyl)hexanamide, having the following formula:

15. The compound of claim 8 , wherein the compound is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethyl silyl)oxy)trisiloxan-3-yl)propyl)hexaminium chloride, having the following formula:

16. The compound of claim 11 , wherein the compound is 3 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

17. The compound of claim 12 , wherein the compound is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-amine oxide, having the following formula:

18. The compound of claim 13 , wherein the compound is 4-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethyl silyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

19. The compound of claim 13 , wherien the compound is 5-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl) propyl)amino-6- oxohexyl)dimethylammonio)pentane-1-sulfonate, having the following formula:

Assignees

• Advansix Resins & Chemicals Llc

Inventors

• Asirvatham Edward
• Honciuc Andrei
• MIHALI Voichita

Classifications

• C09K23/54

  Silicon compounds · CPC title

• C07F7/089

  Treatments not covered by a preceding group · CPC title

• C09K23/28

  Aminocarboxylic acids (proteins and protein hydrolysates C09K23/30) · CPC title

• C07F7/0838 Primary

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title

• C07F7/0834 Primary

  Compounds having one or more O-Si linkage (for compounds with C-O-Si linkages see C07F7/18) · CPC title