Rhamnolipid amides for hair scent retention
The invention provides derivatives of rhamnolipids, formulations comprising these, and the use thereof.
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.