IP Library Granted Patent US 12,459,963
Granted Patent B2
US 12,459,963 · App. 18/597,102 · Granted Nov 4, 2025

Siloxane derivatives of amino acids having surface-active properties

Inventors: Edward Asirvatham (Chatham, NJ); Andrei Honciuc (Iasi, RO); Voichita Mihali (Basel, CH)
Assignee: AdvanSix Resins & Chemicals LLC
C07F7/0834
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Quick Facts
Patent No.
US 12,459,963
App. No.
18/597,102
Granted
Nov 4, 2025
Kind
B2
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.

Claims (23)

1 . A liquid medium, comprising:

water; and

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 liquid medium of claim 1 , wherein R 1 and R 2 are methyl.

3 . The liquid medium of claim 1 , wherein n is 5.

4 . The liquid medium of claim 3 , wherein R 3 is hydrogen.

5 . The liquid medium of claim 4 , wherein the counterion is selected from the group consisting of chloride, bromide, and iodide.

6 . The liquid medium of claim 5 , wherein the counterion is chloride.

7 . The liquid medium of claim 3 , wherein R 3 is methyl.

8 . The liquid medium of claim 7 , wherein the counterion is selected from the group consisting of chloride, bromide, and iodide.

9 . The liquid medium of claim 8 , wherein the counterion is iodide.

10 . The liquid medium of claim 3 , wherein R 3 is an oxygen atom.

11 . The liquid medium of claim 3 , wherein R 3 is C 1 -C 6 alkyl, substituted with sulfonate.

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

13 . The liquid medium of claim 6 , wherein the compound 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:

14 . The liquid medium of claim 9 , 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:

15 . The liquid medium of claim 10 , 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:

16 . The liquid medium of claim 11 , wherein the compound 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:

17 . The liquid medium of claim 11 , wherein 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:

Continuity (4)
Continuation 17230278 · Apr 14, 2021
Continuation 16990855 · Aug 11, 2020
Provisional Application 62890341 · Aug 22, 2019
Related Publication 20240294556A1 · Sep 5, 2024
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