IP Library › Granted Patent US 11,918,670
Granted Patent B2
US 11,918,670 · App. 17/905,835 · Granted Mar 5, 2024

Mixture composition comprising glycolipids and triethyl citrate

Inventors: Kathrin Daniela Brandt (Duesseldorf, DE); Stefan Julian Liebig (Duesseldorf, DE); Hans Henning Wenk (Muelheim an der Ruhr, DE); Manuela Salmina-Petersen (Hamburg, DE); Christoph Tölle (Duisburg, DE); Alina Muss (Essen, DE)
Assignees: Evonik Operations GmbH; Evonik Dr. Straelmans GmbH
A61K8/37A61K8/046A61K8/602A61Q19/10
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Quick Facts
Patent No.
US 11,918,670
App. No.
17/905,835
Granted
Mar 5, 2024
Kind
B2
Abstract

A composition contains glycolipids and triethyl citrate (TEC). The TEC can assist in stabilizing a foam of a corresponding aqueous composition. A method can be used for preparing a corresponding formulation, preferably a cosmetical or pharmaceutical formulation, by providing the composition and diluting the composition. The pH of the composition may be adjusted during the dilution by adding an organic or inorganic base.

Claims (85)

1. A composition, comprising:

0.2% by weight to 70% by weight of at least one glycolipid,

0.01% by weight to 14% by weight of triethyl citrate, and

water,

wherein the percentages by weight refer to the total composition, wherein a weight ratio of all glycolipids to all triethyl citrate comprised in the composition is in a range of from 5:1 to 20:1.

2. The composition according to claim 1 , wherein a pH of the composition at 25° C. is from 4.5 to 7.0.

3. The composition according to claim 1 ,

wherein the composition comprises 40% by weight to 70% by weight of the at least one glycolipid, wherein the percentages by weight refer to the total composition.

4. The composition according to claim 1 ,

wherein the composition comprises 0.2% by weight to 12%, by weight of the at least one glycolipid, wherein the percentages by weight refer to the total composition.

5. The composition according to claim 1 , wherein said composition comprises 51% by weight to 95% by weight of diRL-C10C10,

wherein the percentages by weight refer to a sum total of all rhamnolipids present,

wherein diRL-C10C10 is a di-rhamnolipid of formula (I) or salts thereof, in which radicals R 1 and R 2 ═(CH 2 ) o —CH 3 wherein o==6,

wherein formula (I) is

wherein

m=1,

n=1.

6. The composition according to claim 1 , wherein said composition comprises 0.5% by weight to 9% by weight of monoRL-C10C10, wherein the percentages by weight refer to a sum total of all rhamnolipids present,

monoRL-C10C10 is a mono-rhamnolipid of formula (I) in which radicals R 1 and R 2 ═(CH 2 ) o —CH 3 wherein o=6,

wherein formula (I) is

wherein

m=1,

n=0.

7. The composition according to claim 1 , which comprises di-rhamnolipids and mono-rhamnolipids,

wherein a weight ratio of all di-rhamnolipids present to all mono-rhamnolipids present is greater than 51:49.

8. The composition according to claim 1 , wherein said composition comprises 0.5 to 25% by weight of diRL-C10C12, wherein the percentages by weight refer to a sum total of all rhamnolipids present,

wherein diRL-C10C12 is a di-rhamnolipid of formula (I) and salts thereof, in which one of radicals R 1 and R 2 ═(CH 2 ) o —CH 3 wherein o=6 and remaining radical R 1 or R 2 ═(CH 2 ) o —CH 3 wherein o=8,

wherein formula (I) is

wherein

m=1,

n=1.

9. The composition according to claim 1 , wherein said composition comprises:

0.1% by weight to 5% by weight of monoRL-C10C12, and/or

0.1% by weight to 5% by weight of monoRL-C10C12:1,

wherein the percentages by weight refer to a sum total of all rhamnolipids present,

wherein monoRL-C10C12 is a mono-rhamnolipid of formula (I), in which one of radicals R 1 and R 2 ═(CH 2 ) o —CH 3 wherein o=6 and remaining radical R 1 or R 2 ═(CH 2 ) o —CH 3 wherein o=8,

wherein monoRL-C10C12:1 is a mono-rhamnolipid of formula (I), in which one of radicals R 1 and R 2 ═(CH 2 ) o —CH 3 where o=6 and remaining radical R 1 or R 2 =an unbranched, unsubstituted hydrocarbon radical having 9 carbon atoms having 1 double bond,

wherein formula (I) is

wherein

m=1,

n=0.

10. The composition according to claim 1 , wherein said composition comprises:

0.5% by weight to 15% by weight of diRL-C10C12:1,

0.5 to 25% by weight of diRL-C10C12,

0.1% by weight to 5% by weight of monoRL-C10C12, and

0.1% by weight to 5% by weight of monoRL-C10C12:1,

wherein the percentages by weight refer to a sum total of all rhamnolipids present,

wherein diRL-C10C12:1 is a di-rhamnolipid of formula (I), in which n=1 and one of radicals R 1 and R 2 ═(CH 2 ) o —CH 3 wherein o=6 and remaining radical R 1 or R 2 =an unbranched, unsubstituted hydrocarbon radical having 9 carbon atoms having 1 double bond,

wherein diRL-C10C12 is a di-rhamnolipid of formula (I) and salts thereof, in which n=1 and one of radicals R 1 and R 2 ═(CH 2 ) o —CH 3 wherein o=6 and remaining radical R 1 or R 2 ═(CH 2 ) o —CH 3 wherein o=8,

wherein monoRL-C10C12 is a mono-rhamnolipid of formula (I), in which n=0 and one of radicals R 1 and R 2 ═(CH 2 ) o —CH 3 wherein o=6 and remaining radical R 1 or R 2 ═(CH 2 ) o —CH 3 wherein o=8,

wherein monoRL-C10C12:1 is a mono-rhamnolipid of formula (I), in which n=0 and one of radicals R 1 and R 2 ═(CH 2 ) o —CH 3 where o=6 and remaining radical R 1 or R 2 =an unbranched, unsubstituted hydrocarbon radical having 9 carbon atoms having 1 double bond,

wherein formula (I) is

wherein

m=1.

11. The composition according to claim 1 , wherein said composition comprises at least one preservative selected from the group consisting of p-anisic acid, levulinic acid, lactic acid, citric acid, and a salt of the aforementioned acids.

12. A method for preparing a formulation of at least one glycolipid, the method comprising:

a) providing a composition comprising

40% by weight to 70% by weight of at least one glycolipid,

2.0% by weight to 14% by weight of triethyl citrate, and

water,

 wherein the percentages by weight refer to the total composition, wherein a weight ratio of all glycolipids to all triethyl citrate comprised in the composition is in a range of from 5:1 to 20:1, and

b) diluting the composition with at least partially water to a formulation comprising 0.2% by weight to 12% by weight of the at least one glycolipid, where the percentages by weight refer to the total formulation.

13. The method according to claim 12 , wherein a pH of the formulation in b) is adjusted to a pH of at 25° C. from 4.5 to 7.0.

14. A method, comprising:

adding triethyl citrate to an aqueous composition containing at least one glycolipid, to stabilize a foam of the aqueous composition, thereby obtaining a stabilized foam of the aqueous composition which comprises

0.2% by weight to 70% by weight of said at least one glycolipid,

0.01% by weight to 14% by weight of said triethyl citrate, and

water,

wherein the percentages by weight refer to the total stabilized foam, wherein a weight ratio of all glycolipids to all triethyl citrate comprised in the stabilized foam is in a range of from 5:1 to 20:1.

15. The composition according to claim 1 , comprising:

0.4% by weight to 55% by weight of the at least one glycolipid, and

0.02% by weight to 11% by weight of triethyl citrate,

wherein the percentages by weight refer to the total composition.

16. The composition according to claim 9 , wherein the composition comprises:

0.1% by weight to 5% by weight of the monoRL-C10C12, and

0.1% by weight to 5% by weight of the monoRL-C10C12:1,

wherein the percentages by weight refer to the sum total of all rhamnolipids present,

wherein monoRL-C10C12 is a mono-rhamnolipid of formula (I), in which n=0 and one of radicals R 1 and R 2 ═(CH 2 ) o —CH 3 wherein o=6 and remaining radical R 1 or R 2 =an (CH 2 ) o —CH 3 wherein o=8,

wherein monoRL-C10C12:1 is a mono-rhamnolipid of formula (I), in which n=0 and one of radicals R 1 and R 2 ═(CH 2 ) o —CH 3 where o=6 and remaining radical R 1 or R 2 =an unbranched, unsubstituted hydrocarbon radical having 9 carbon atoms having 1 double bond,

wherein formula (I) is

wherein

m=1.

17. The composition according to claim 11 , wherein the composition comprises the at least one preservative at a concentration of from 0.01% by weight to 14% by weight, where the percentages by weight refer to the total composition.

18. The method according to claim 12 , wherein the formulation is a cosmetical or pharmaceutical composition.

19. The method according to claim 13 , wherein the pH of the formulation is adjusted in b) by adding an organic or inorganic base.

Assignments (1)
MERGER Recorded Sep 15, 2025
From: EVONIK DR. STRAETMANS GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 072259/0959 →
Priority Claims (1)
EP 20162304 · Mar 11, 2020 · regional
Continuity (1)
Related Publication 20230121094A1 · Apr 20, 2023
Cited By (1)
US 12,448,588