Siloxane derivatives of amino acids having surface-active properties

Patent metadata

Field	Value
Publication number	US-11952394-B2
Application number	US-202117230278-A
Country	US
Kind code	B2
Filing date	Apr 14, 2021
Priority date	Aug 22, 2019
Publication date	Apr 9, 2024
Grant date	Apr 9, 2024

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 method of synthesizing a siloxane derivative of an amino acid, comprising:
alkylating an amino end group of 6-aminohexanoic acid to provide a disubstituted amine; and
reacting a carboxyl end group of the disubstituted amine with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative of the amino acid.

2. A method of synthesizing a siloxane derivative of the Formula I, comprising reacting a carboxyl end group of the following N-alkylated amino acid:

with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative of the amino acid of the 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.

3. The method of claim 2 , wherein in Formula I, n is an integer from 3 to 6.

4. The method of claim 3 , wherein in Formula I, n is 5.

5. The method of claim 1 , further comprising the additional step, prior to said alkylating step, of ring-opening caprolactam to form the 6-aminohexanoic acid.

6. The method of claim 2 , wherein the siloxane derivative of the amino acid is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide, having the following formula:

7. The method of claim 6 , further comprising the additional step, after said reacting step, of treating the siloxane derivative of the amino acid with hydrochloric acid to form 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexaminium chloride, having the following formula:

8. The method of claim 6 , further comprising the additional step, after said reacting step, of treating the siloxane derivative of the amino acid with methyl iodide to form 3 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethyl silyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

9. The method of claim 6 , further comprising the additional step, after said reacting step, of treating the siloxane derivative of the amino acid with hydrogen peroxide to form 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:

10. The method of claim 6 , further comprising the additional step, after said reacting step, of treating the siloxane derivative of the amino acid with 1,2-butane sultone to form 4-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

11. The method of claim 1 , wherein the siloxane derivative of the amino acid 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:

12. The method of claim 1 , wherein the siloxane derivative of the amino acid is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexaminium chloride, having the following formula:

13. The method of claim 1 , wherein the siloxane derivative of the amino acid is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethyl silyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

14. The method of claim 1 , wherein the siloxane derivative of the amino acid is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethyl silyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-amine oxide, having the following formula:

15. The method of claim 1 , wherein the siloxane derivative of the amino acid is 4-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

16. The method of claim 2 , further comprising the additional step, prior to said reacting step, of ring-opening caprolactam to form the 6-aminohexanoic acid.

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

• C07F7/0834 Primary

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