Rhamnolipid esters as nonionic surfactants for cosmetic use

Patent metadata

Field	Value
Publication number	US-10676495-B2
Application number	US-201716075298-A
Country	US
Kind code	B2
Filing date	Feb 15, 2017
Priority date	Feb 22, 2016
Publication date	Jun 9, 2020
Grant date	Jun 9, 2020

Abstract

The invention provides ester derivatives of rhamnolipids, formulations comprising these, and the use thereof.

First claim

The invention claimed is:

1. A rhamnolipid ester of the general formula (I)

wherein
m=2, 1 or 0
n=1 or 0
R 1 =organic radical having 2 to 24 carbon atoms,
R 2 =independently of one another, identical or different, organic radical having 2 to 24 carbon atoms, and
R 3 is selected from the group consisting of branched or linear alkyl radicals having 12 to 18 carbon atoms.

2. The rhamnolipid ester according to claim 1 , wherein R 3 is selected from the group of the radicals R 3 derived from OHR 3 =natural fatty alcohol.

3. The rhamnolipid ester according to claim 1 , wherein the R 3 is selected from the group consisting of lauryl, myristyl, palmityl and stearyl radicals.

4. A process for the preparation of rhamnolipid ester comprising the process steps of
A) providing at least one rhamnolipid,
B) reacting the rhamnolipid with at least one coupling reagent,
C) reacting the rhamnolipid activated by process step B) with an alcohol having 1 to 32 carbon atoms, and optionally
D) purifying the rhamnolipid ester.

5. The process according to claim 4 , wherein in process step B) the coupling reagent used is at least one selected from the group consisting of dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N-cyclohexyl-N′-(2′-morpholinoethyl)carbodiimide metho-p-toluenesulphonate, N-benzyl-N′-3′ dimethylaminopropylcarbodiimide hydrochloride, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, N-ethylcarbodiimide hydrochloride and carbonyldiimidazole.

6. The process according to claim 4 , wherein in process step C) at least one catalyst selected from the group consisting of N-ethyldiisopropylamine, trialkylamines, pyridine, 4-dimethylaminopyridine and hydroxybenzotriazole.

7. A cosmetic formulation, comprising at least one rhamnolipid ester according to claim 1 .

8. A cosmetic application comprising the rhamnolipid ester according to a formulation according to claim 7 .

9. A cosmetic application comprising the rhamnolipid ester according to a formulation according to claim 7 in formulations for inhibiting hair growth.

10. The rhamnolipid ester according to claim 1 , wherein
m=1 or 0,
n=1
R 1 =organic radical selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=1 to 23,
R 2 =organic radical having 5 to 13 carbon atoms and selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=1 to 23.

11. The rhamnolipid ester according to claim 1 , wherein
m=1 or 0,
n=1
R 1 =organic radical selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=4 to 12,
R 2 =organic radical having 5 to 13 carbon atoms and selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=4 to 12.

12. The rhamnolipid ester according to claim 1 , wherein R 3 is selected from branched or linear alkyl radicals having 12 to 18 carbon atoms.

13. The process according to claim 4 , wherein in process step B) the coupling reagent used is selected from the group consisting of dicyclohexylcarbodiimide and diisopropylcarbodiimide.

14. The process according to claim 4 , wherein in process step C) at least one catalyst is hydroxybenzotriazole.

15. A shaving application comprising the rhamnolipid ester according to a formulation according to claim 7 .

16. The process according to claim 4 , wherein for the rhamnolipid ester is the general formula (I)

wherein
m=2, 1 or 0
n=1 or 0
R 1 =organic radical having 2 to 24 carbon atoms,
R 2 =independently of one another, identical or different, organic radical having 2 to 24 carbon atoms, and
R 3 is selected from the group consisting of branched or linear alkyl radicals having 12 to 18 carbon atoms.

17. The process of claim 4 , wherein
m=1 or 0,
n=1
R 1 =organic radical selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=1 to 23,
R 2 =organic radical having 5 to 13 carbon atoms and selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=1 to 23.

18. The process of claim 4 , wherein
m=1 or 0,
n=1
R 1 =organic radical selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=4 to 12,
R 2 =organic radical having 5 to 13 carbon atoms and selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=4 to 12.

19. The process of claim 4 , wherein R 3 is selected from branched or linear alkyl radicals having 12 to 18 carbon atoms,
m=1 or 0,
n=1
R 1 =organic radical selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=4 to 12,
R 2 =organic radical having 5 to 13 carbon atoms and selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=1 to 23.

20. The process of claim 4 , wherein the R 3 is selected from the group consisting of lauryl, myristyl, palmityl and stearyl radicals.

Assignees

• Evonik Degussa Gmbh
• Evonik Operations Gmbh

Inventors

• Lu Xin
• Nattland Sandra
• Van Logchem Monica Desiree
• Wenk Hans Henning
• Cabirol Fabien
• Dahl Verena
• Scheuermann Ralph
• Brandt Kathrin Daniela
• Kleinen Jochen

Classifications

• A61K8/604

  Alkylpolyglycosides; Derivatives thereof, e.g. esters · CPC title

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title

• C07H15/06 Primary

  being a hydroxyalkyl group esterified by a fatty acid · CPC title

• A61Q7/02

  Preparations for inhibiting or slowing hair growth · CPC title

• A61Q9/02

  Shaving preparations · CPC title