Rhamnolipid amides for hair scent retention

Patent metadata

Field	Value
Publication number	US-10941173-B2
Application number	US-201716074828-A
Country	US
Kind code	B2
Filing date	Feb 15, 2017
Priority date	Feb 22, 2016
Publication date	Mar 9, 2021
Grant date	Mar 9, 2021

Abstract

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

First claim

The invention claimed is:

1. A Rhamnolipid amide according the formula (I)

where
m=2, 1 or 0,
n=1 or 0
R 1 =organic radical having 2 to 24 of carbon atoms,
R 2 =independently of one another, identical or different, organic radical having 2 to 24, carbon atoms,
R 3a =a structure selected from the group consisting of,

wherein
R 4 and R 5 =independently of one another, identical or different alkyl radical having 1 to 6 carbon atoms,
R 6 =an alkylene group having 1 to 6 carbon atoms, and

where
R 7 =an alkylene group having 1 to 22 carbon atoms,
Z=H, OH, OR 8 where
R 8 =alkyl radical having 1 to 6 carbon atoms, and
R 6 =an alkylene group having 1 to 6 carbon atoms, and
R 3b =hydrogen.

2. The rhamnolipid amide according to claim 1 wherein
R 4 and R 5 =independently of one another, identical or different alkyl radical having 1 to 3 carbon atoms,
R 6 =an alkylene group having 2 to 3 carbon atoms,
R 7 =an alkylene group having 2 to 18 carbon atoms, and
R 8 =alkyl radical having 1 to 3 carbon atoms.

3. The rhamnolipid amide according to claim 1 , wherein
R 6 =an alkylene group having 1 to 3 carbon atoms, and
R 7 =an alkylene group having 1 to 18 carbon atoms.

4. The rhamnolipid amide according to claim 1 , wherein
m=1 or 0,
n=1,
R 1 =organic radical having 5 to 13 carbon atoms,
R 2 =independently of one another, identical or different, organic radical having 5 to 13 carbon atoms, and
R 3b =organic radical having 4 to 8 carbon atoms or H.

5. The rhamnolipid amide 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 =independently of one another, identical or different, organic radical having 2 to 24 selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 where o=1 to 23, and
R 3b =H.

6. The rhamnolipid amide 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 wherein o=4 to 12,
R 2 =independently of one another, identical or different, organic radical having 2 to 24 selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 ) o —CH 3 wherein o=4 to 12, and
R 3b =H.

7. The rhamnolipid amide according to claim 1 , wherein
R 4 and R 5 =independently of one another, identical or different alkyl radical having 1 carbon atom,
R 6 =an alkylene group having 2 to 3 carbon atoms,
R 7 =an alkylene group having 3 to 8 carbon atoms,
Z=H, OH, OR 8 where
R 8 =alkyl radical having 1 carbon atoms, and

R 3b =H.

8. A cosmetic formulation comprising the rhamnolipid amide according to claim 1 .

9. A hair fragrance comprising the rhamnolipid amide according to claim 8 .

10. A process for the preparation of rhamnolipid amides comprising the process steps
A) providing a rhamnolipid,
B) reacting the rhamnolipid with at least one coupling reagent,
C) reacting the rhamnolipid activated by process step B) with an amine, and optionally
D) purifying out a rhamnolipid amide as set forth in claim 1 .

11. The process according to claim 10 , wherein in process step B) the coupling reagent is selected from the group consisting of dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide 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.

12. The process according to claim 10 , wherein in process step C) at least one catalyst selected from the the group consisting of N-ethyldiisopropylamine, trialkylamines, pyridine, 4-dimethylaminopyridine and hydroxybenzotriazole.

13. The process according to claim 10 , wherein in process step B) the coupling reagent used is at least one selected from the group consisting of dicyclohexylcarbodiimide and diisopropylcarbodiimide.

14. The process according to claim 10 , wherein in that in process step C) at least one catalyst is hydroxybenzotriazole.

15. The process according to claim 11 , wherein in that in process step C) at least one catalyst is hydroxybenzotriazole.

16. A Rhamnolipid amide comprising the 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,
R 3a =a structure selected from the group consisting of

wherein
R 4 and R=independently of one another, identical or different alkyl radical having 1 to
6 carbon atoms,
R 6 =an alkylene group having 1 to 3 carbon atoms, and

where
R 7 =an alkylene group having 1 to 22 carbon atoms,
Z=H, OH, OR 8 where

R 8 =alkyl radical having 1 to 3 carbon atoms, and
R ab =hydrogen.

17. The rhamnolipid amide according to claim 16 wherein
R 4 and R 5 =independently of one another, identical or different alkyl radical having 1 to 3 carbon atoms,
R 6 =an alkylene group having 2 to 3 carbon atoms,
R 7 =an alkylene group having 2 to 18 carbon atoms.

18. The rhamnolipid amide according to claim 16 , 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, and
R 2 =independently of one another, identical or different, organic radical having 2 to 24 selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH 2 )o-CH 3 where o=1 to 23.

19. The rhamnolipid amide according to claim 16 , wherein
m=1 or 0,
n=1,
R 1 =organic radical having 5 to 13 carbon atoms, and
R 2 =independently of one another, identical or different, organic radical having 5 to 13 carbon atoms.

Assignees

• 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

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title

• A61Q5/02

  Preparations for cleaning the hair · CPC title

• C07H15/04

  attached to an oxygen atom of the saccharide radical · CPC title

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• C07H15/06 Primary

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