IP Library › Granted Patent US 12,497,426
Granted Patent B2
US 12,497,426 · App. 18/005,942 · Granted Dec 16, 2025

Rhamnolipid oligo-esters

Inventors: Xin Lu (Essen, DE); Jochen Kleinen (Heinsberg, DE); Hans Henning Wenk (Muelheim an der Ruhr, DE)
Assignee: Evonik Operations GmbH
C07H15/06A61K8/604A61Q15/00C07H1/00
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Quick Facts
Patent No.
US 12,497,426
App. No.
18/005,942
Granted
Dec 16, 2025
Kind
B2
Abstract

A rhamnolipid ester is useful as a cosmetic additive. A method of its production involves providing at least one rhamnolipid, reacting the at least one rhamnolipid with at least one coupling reagent, reacting the at least one rhamnolipid with a polyhydric alcohol having 1 to 32 carbon atoms, and optionally purifying the at least one rhamnolipid ester.

Claims (54)

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

general formula (I),

wherein

m=independently of one another, identical or different, 2, 1, or 0,

n=independently of one another, identical or different, 1 or 0,

Z=2 to 10,

R 1 =independently of one another, identical or different, an organic radical having 2 to 24 carbon atoms,

R 2 =independently of one another, identical or different, an organic radical having 2 to 24 carbon atoms, and

A is a z-valent organic radical.

2 . The rhamnolipid ester according to claim 1 , wherein a rhamnolipid radical of the general formula (I) is selected from the group consisting of diRL-C10C10, diRL-C8C10, diRL-C10C12, diRL-C10C12:1, and monoRL-C10C10.

3 . The rhamnolipid ester according to claim 1 , wherein

z=2, and

A is a two valent hydrocarbyl radical, which can be substituted by one or more hydroxyl groups.

4 . The rhamnolipid ester according to claim 1 , wherein

z=2, and

A is selected from the group consisting of

5 . The rhamnolipid ester according to claim 1 , wherein

z=2, and

A is selected from the group consisting of

6 . The rhamnolipid ester according to claim 1 , wherein

a rhamnolipid radical of the general formula (1) is selected from the group consisting of diRL-C10C10, diRL-C8C10, diRL-C10C12, diRL-C10C12:1, and monoRL-C10C10,

z=2, and

A is selected from the group consisting of

wherein

R 3 =R 4 =H, r=t=0, s=0 to 8, 10, 12, or 14,

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

8 . A cosmetic formulation for anti-perspirant applications, comprising:

the rhamnolipid ester according to claim 1 .

9 . The rhamnolipid ester according to claim 1 , wherein in general formula (I),

R 1 =independently of one another, an optionally branched, optionally substituted, and optionally unsaturated alkyl radical; and/or

R 2 =independently of one another, an optionally branched, optionally substituted, and optionally unsaturated alkyl radical.

10 . The rhamnolipid ester according to claim 1 , wherein in general formula (1),

R 1 =independently of one another, selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl, tridecenyl, and (CH 2 ) o —CH 3 wherein o=1 to 23.

11 . The rhamnolipid ester according to claim 1 , wherein in general formula (I),

R 2 =independently of one another, selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl, tridecenyl, and (CH 2 ) o —CH 3 wherein o=1 to 23.

12 . The rhamnolipid ester according to claim 3 , wherein A is

wherein

R 3 and R 4 are CH 3 or H,

r=0 to 3,

s=0 to 24, and

t=0 to 24.

13 . The rhamnolipid ester according to claim 3 , wherein A is

14 . A process for the preparation of at least one rhamnolipid ester according to claim 1 , comprising:

A) providing at least one rhamnolipid,

B) reacting the at least one rhamnolipid with at least one coupling reagent,

C) reacting the at least one rhamnolipid activated by B) with a polyhydric alcohol having 1 to 32 carbon atoms, to obtain the at least one rhamnolipid ester, and

optionally,

D) purifying the at least one rhamnolipid ester.

15 . The process according to claim 14 , wherein in B), the at least one coupling reagent 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.

16 . The process according to claim 14 , wherein the reacting in C) is with at least one catalyst selected from the group consisting of N-ethyldiisopropylamine, trialkylamine, pyridine, 4-dimethylaminopyridine, and hydroxybenzotriazole.

17 . The process according to claim 14 , wherein in A), the at least one rhamnolipid is selected from the group consisting of diRLC10C10, diC8C10, diRLC10C12, diRLC10C12:1, monoRLC10C10, and a mixture thereof.

18 . The process according to claim 14 , wherein in C), the polyhydric alcohol is at least one selected from the group of 1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,2-hexanediol, 2,5-hexanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octandiol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, 1,2-dodecanediol, 1,2-tetradecandiol, 1,14-tetradecanediol, and 1,16-hexadecanediol.

19 . A method, comprising:

adding the rhamnolipid ester according to claim 1 to a formulation for inhibiting body odor and/or sweat.

Priority Claims (1)
EP 20187101 · Jul 22, 2020 · regional
Continuity (1)
Related Publication 20230348514A1 · Nov 2, 2023
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