Process for preparing alkyl pyroglutamic acids

Patent metadata

Field	Value
Publication number	US-9260388-B2
Application number	US-201214364218-A
Country	US
Kind code	B2
Filing date	Dec 13, 2012
Priority date	Dec 15, 2011
Publication date	Feb 16, 2016
Grant date	Feb 16, 2016

Abstract

Disclosed are compounds of formulae (I) and (II) and salts, hydrates, or solvates thereof, where R 1 , R 2 , R 3 , R 5 , and R 6 are defined herein, compositions containing these compounds, methods of preparing these compounds, and methods of using these compounds in a variety of applications, such as a surfactant or additive in personal care products.

First claim

What is claimed is:

1. A compound of the formula (I):

or acceptable salts, hydrates, or solvates thereof; wherein
R 1 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, M + , or a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped;
where M + is a cation forming a salt;

R 2 and R 3 are independently C 2 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl, each optionally substituted with one or more of R 4 ; and
wherein R 4 is halogen, —CN, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —OH, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6 alkyl), —CON(C 1 -C 6 alkyl), —CON(C 1 -C 6 alkyl) 2 , C 3 -C 8 cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein each cycloalkyl, aryl, heteroaryl, and heterocyclyl are optionally substituted with one or more of halogen, —CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —OH, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6 alkyl), —CON(C 1 -C 6 alkyl), or —CON(C 1 -C 6 alkyl) 2 ;
or R 4 is polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped.

2. A compound according to claim 1 , wherein R 1 is hydrogen or M + .

3. A compound according to claim 1 , wherein R 1 is a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped.

4. A compound according to claim 1 , wherein R 2 is C n alkyl, and R 3 is C n-2 alkyl, each optionally substituted with one or more of R 4 , and wherein n is 4-12.

5. A compound according to claim 4 , wherein n is 5 or 10.

6. A compound according to claim 1 , which is:

7. A composition comprising a compound according to claim 1 , and at least one additive, excipient or diluent.

8. A compound according to claim 1 which is suitable as a surfactant, surface active additive, or phase transfer catalyst.

9. A compound according to claim 1 which is suitable in personal care formulations.

10. A personal care formulation comprising a compound according to claim 1 .

11. A personal care formulation comprising a composition according to claim 7 .

12. A method for carrying out phase transfer in a reaction system comprising adding to the system a compound according to claim 1 .

13. A method for carrying out phase transfer in a reaction system comprising adding to the system a composition according to claim 7 .

14. A personal care formulation according to claim 10 , where the formulation is a shampoo or a body wash formulation.

Assignees

• Dow Global Technologies Llc

Inventors

• Henton Daniel R
• Rand Cynthia L
• Ng Sze-Sze

Classifications

• B01J2231/005

  General concepts, e.g. reviews, relating to methods of using catalyst systems, the concept being defined by a common method or theory, e.g. microwave heating or multiple stereoselectivity · CPC title

• A61K8/4913

  having five membered rings, e.g. pyrrolidone carboxylic acid · CPC title

• C07D207/18

  having one double bond between ring members or between a ring member and a non-ring member · CPC title

• B01J2531/002

  Materials · CPC title

• A61Q5/02

  Preparations for cleaning the hair · CPC title