Amino acid surfactants

Patent metadata

Field	Value
Publication number	US-11795143-B2
Application number	US-202117154916-A
Country	US
Kind code	B2
Filing date	Jan 21, 2021
Priority date	Jan 29, 2020
Publication date	Oct 24, 2023
Grant date	Oct 24, 2023

Abstract

The present disclosure provides 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 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 method of synthesizing an amino acid surfactant, comprising the steps of:
(1) opening a lactam to yield an amino acid having an N-terminus;
(2) reacting the N-terminus of the amino acid with an alkylating agent to yield a tertiary amine;
(3) reacting the tertiary amine with an alcohol under acidic conditions to yield an amino acid ester having an N-terminus; and
(4) reacting the N-terminus of the amino acid ester with a sulfonating agent to yield an amino acid surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from C 1 -C 6 alkyl.

2. The method of claim 1 , wherein in step 1, the lactam is caprolactam.

3. The method of claim 1 , wherein in step 2, the alkylating agent is formaldehyde or paraformaldehyde.

4. The method of claim 1 , wherein in step 3, the alcohol is dodecanol.

5. The method of claim 1 , wherein in step 3, the acid is p-toluene sulfonic acid.

6. The method of claim 1 , wherein in step 4, the sulfonating agent is 1,4-butanesultone.

Assignees

• Advansix Resins & Chemicals Llc

Inventors

• Asirvatham Edward
• Honciuc Andrei
• MIHALI Voichita

Classifications

• C07C309/14 Primary

  containing amino groups bound to the carbon skeleton · CPC title

• A61K8/466

  containing sulfonic acid derivatives; Salts · CPC title

• A61Q5/02

  Preparations for cleaning the hair · CPC title

• A61Q5/12

  Preparations containing hair conditioners · CPC title

• C07C303/22

  from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; {from sulfonic halides by reactions not involving the formation of halosulfonyl groups} · CPC title