Process for preparing alkyl pyroglutamic acids

Patent metadata

Field	Value
Publication number	US-2016237033-A1
Application number	US-201615045921-A
Country	US
Kind code	A1
Filing date	Feb 17, 2016
Priority date	Dec 15, 2011
Publication date	Aug 18, 2016
Grant date	—

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

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 cycoalkyl, 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 composition comprising at least two compounds selected from the 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 2 -C 24 alkyl, unbranched or branched C 2 -C 24 alkenyl, unbranched or branched C 2 -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 2 -C 24 alkyl, unbranched or branched C 2 -C 24 alkenyl, unbranched or branched C 2 -C 24 alkynyl, O 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 .

9 . A composition according to claim 8 further comprising at least one additive, excipient or diluent.

10 . A composition according to claim 8 , comprising at least two compounds of formula (II).

11 . A composition according to claim 10 , comprising at least two compounds that are:

12 . A composition according to claim 12 , comprising at least two compounds that are:

13 . A compound according to claim 1 , for use as a surfactant, surface active additive, or phase transfer catalyst.

14 . A compound according to claim 1 for use in personal care formulations.

15 . A method of preparing a compound of formula (IV) or a mixture of one or more compounds of formula (IV):

or acceptable salts, hydrates, or solvates thereof; wherein
R 11 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 can be capped or uncapped;
where M + is a cation forming a salt;

R 12 is unbranched or branched C 3 -C 24 alkyl, unbranched or branched C 3 -C 24 alkenyl, or unbranched or branched C 3 -C 24 alkynyl, each optionally substituted with one or more of R 15 ; and
wherein R 15 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 ;

comprising
treating a glutamate of formula:

wherein each R 14 is independently selected form hydrogen, M + , C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, —(C 1 -C 6 alkyl-0) 1-4 H, aryl, aryl(C 1 -C 6 alkyl), or polyoxyalkylene unit;

with an aldehyde of formula:

Assignees

• Dow Global Technologies Llc

Inventors

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

Classifications

• C11D3/28

  Heterocyclic compounds containing nitrogen in the ring · 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

• C11D3/32

  Amides; Substituted amides · CPC title

• A61Q19/10

  Washing or bathing preparations · CPC title