Process for preparing alkyl pyroglutamic acids

Patent metadata

Field	Value
Publication number	US-10577319-B2
Application number	US-201815918552-A
Country	US
Kind code	B2
Filing date	Mar 12, 2018
Priority date	Dec 15, 2011
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

Abstract

Disclosed are compounds of formulae:

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

The invention claimed is:

1. A composition comprising at least two compounds selected from the group consisting of compounds of formula (II):

or acceptable salts, hydrates, or solvates thereof; wherein
R 5 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 6 is unbranched or branched C 7 -C 24 alkyl, unbranched or branched C 7 -C 24 alkenyl, unbranched or branched C 8 -C 24 alkynyl, C 3 -C 8 cycloalkyl, or C 3 -C 8 cycloalkyl(C 1 -C 6 alkyl), each optionally substituted with one or more of R 7 ; and
wherein R 7 is 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), —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 ; and

of formula (III):

or acceptable salts, hydrates, or solvates thereof; wherein
each R 8 is independently 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 9 is unbranched or branched C 7 -C 24 alkyl, unbranched or branched C 8 -C 24 alkenyl, unbranched or branched C 7 -C 24 alkynyl, C 3 -C 8 cycloalkyl, or C 3 -C 8 cycloalkyl(C 1 -C 6 alkyl), each optionally substituted with one or more of R 10 ; and
wherein R 10 is 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), —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 .

2. A composition according to claim 1 further comprising at least one additive, excipient or diluent.

3. A composition according to claim 1 , comprising at least two compounds of formula (II).

4. A composition according to claim 3 , comprising at least two compounds that are:

5. A composition according to claim 1 , comprising at least two compounds that are:

Assignees

• Dow Global Technologies Llc

Inventors

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

Classifications

• C11D1/10

  Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof · CPC title

• A61K8/44

  Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof · CPC title

• C11D3/33

  Amino carboxylic acids · CPC title

• C11D3/28

  Heterocyclic compounds containing nitrogen in the ring · CPC title

• A61Q5/02

  Preparations for cleaning the hair · CPC title