Estolide composition for topical applications

Patent metadata

Field	Value
Publication number	US-12076429-B2
Application number	US-202117909038-A
Country	US
Kind code	B2
Filing date	Mar 17, 2021
Priority date	Mar 19, 2020
Publication date	Sep 3, 2024
Grant date	Sep 3, 2024

Abstract

The invention relates to an estolide ester composition with improved sensory properties for cosmetic or pharmaceutical topical applications.

First claim

We claim:

1. An estolide ester composition obtained by the process comprising:
a) an addition reaction of a saturated fatty acid composition (C1) to an unsaturated fatty acid composition (C2) in the presence of a catalyst in order to obtain an acid estolide composition (C3), and
b) optionally, a treatment step for removing unsaturated fatty acids and/or saturated fatty acids from the acid estolide composition (C3) and/or a separation step for separating the acid monoestolides from the acid polyestolides present in the acid estolide composition (C3) in order to obtain a treated acid estolide composition (C3bis), and
c) an esterification reaction of the acid estolides of the acid estolide composition (C3), or, if any, of the treated acid estolide composition (C3bis), using an alcohol composition (C4) comprising one or more linear or branched alcohols with 2 to 6 carbon atoms, in order to obtain an estolide ester composition (C5),
said saturated fatty acid composition (C1) comprising saturated fatty acids with 10 to 20 carbon atoms,
said unsaturated fatty acid composition (C2) comprising at least 85% by weight of mono-unsaturated fatty acids with 8 to 22 carbon atoms, with respect to the total weight of the unsaturated fatty acid composition (C2).

2. The estolide ester composition according to claim 1 , wherein the acid estolide composition (C3) undergoes a treatment step to remove unsaturated fatty acids and/or saturated fatty acids, in order to obtain a treated acid estolide composition (C3bis).

3. The estolide ester composition according to claim 1 , wherein the acid estolide composition (C3) or if any (C3bis) undergoes a separation step for separating the acid monoestolides from the acid polyestolides present in the acid estolide composition.

4. The estolide ester composition according to claim 1 , wherein, at the end of the esterification reaction, the estolide ester composition (C5) undergoes a treatment step for removing the alcohols.

5. The estolide ester composition according to claim 1 , wherein it comprises at least compounds with the formula (I):

wherein:
R1 is a linear or branched alkylene radical with 1 to 19 carbon atoms,
R2 is a hydrogen atom or a linear or branched alkyl radical with 1 to 19 carbon atoms,
R3 is a linear or branched alkyl radical with 2 to 6 carbon atoms,
R4 is a linear or branched alkyl radical with 9 to 19 carbon atoms,
x is an integer equal to 0 or 1,
where it is understood that the sum of the carbon atoms of the radicals R1 and R2 ranges from 5 to 19,
n is an integer greater than or equal to zero.

6. The estolide ester composition according to claim 5 , wherein it contains at least 30% by weight of compounds with the formula (I), with respect to the total weight of the estolide ester composition.

7. The estolide ester composition according to claim 1 , wherein it has an iodine number lower than or equal to 12 g/100 g of iodine as measured according to the NF EN ISO 3961 method.

8. The estolide ester composition according to any claim 1 , having an estolide number of from 1.0 to 1.3.

9. Method for preparing a cosmetic composition, the method comprising using the estolide ester composition according to claim 1 .

10. A cosmetic composition comprising:
at least one estolide ester composition according to claim 1 , and
at least one fatty substance and/or at least one cosmetic additive, said fatty substance and said cosmetic additive being different from said estolide esters.

11. The cosmetic composition according to claim 10 , comprising, with respect to the total weight of the cosmetic composition:
from 1 to 80% by weight of estolide ester composition(s),
from 1 to 80% by weight of fatty substances other than the estolides chosen from hydrocarbon oils, vegetable oils, vegetable butters, fatty ethers and alcohols, oily esters, alkanes and silicone oils,
from 0.1 to 30% by weight of cosmetic additives chosen from surfactants, preservatives, sequestering agents, antioxidants, fragrances, coloring materials, fillers, thickeners, slimming agents, and mixtures thereof.

12. The composition according to claim 1 , wherein the acid estolide composition (C3) undergoes a treatment step by molecular distillation to remove unsaturated fatty acids and/or saturated fatty acids, in order to obtain a treated acid estolide composition (C3bis).

13. The composition according to claim 1 , wherein, at the end of the esterification reaction, the estolide ester composition (C5) undergoes a treatment step by molecular distillation for removing the alcohols.

14. The composition according to claim 5 , wherein it contains at least 40% by weight of compounds with the formula (I), with respect to the total weight of the estolide ester composition.

15. The composition according to claim 1 , wherein it has an iodine number from 1 to 10 g/100 g of iodine, as measured according to the NF EN ISO 3961 method.

16. Method according to claim 9 , wherein the estolide composition is used as an emollient of the cosmetic composition.

17. The cosmetic composition according to claim 10 , comprising, with respect to the total weight of the cosmetic composition:
i. from 5 to 50% by weight of estolide ester composition(s),
ii. from 20 to 60% by weight of fatty substances other than the estolides chosen from hydrocarbon oils, vegetable oils, vegetable butters, fatty ethers and alcohols, oily esters, alkanes and silicone oils,
iii. from 1 to 20% by weight of cosmetic additives chosen from surfactants, preservatives, sequestering agents, antioxidants, fragrances, coloring materials, fillers, thickeners, slimming agents, and mixtures thereof.

18. An estolide ester composition obtained by the process comprising:
a) an addition reaction of a saturated fatty acid composition (C1) to an unsaturated fatty acid composition (C2) in the presence of a catalyst in order to obtain an acid estolide composition (C3), and
b) optionally, a treatment step for removing unsaturated fatty acids and/or saturated fatty acids from the acid estolide composition (C3) and/or a separation step for separating the acid monoestolides from the acid polyestolides present in the acid estolide composition (C3) in order to obtain a treated acid estolide composition (C3bis), and
c) an esterification reaction of the acid estolides of the acid estolide composition (C3), or, if any, of the treated acid estolide composition (C3bis), using an alcohol composition (C4) comprising one or more linear or branched alcohols with 2 to 6 carbon atoms, in order to obtain an estolide ester composition (C5),
said saturated fatty acid composition (C1) comprising saturated fatty acids with 10 to 20 carbon atoms,
said unsaturated fatty acid composition (C2) comprising at least 85% by weight of mono-unsaturated fatty acids with 8 to 22 carbon atoms, with respect to the total weight of the unsaturated fatty acid composition (C2),
wherein the unsaturated fatty acids in the unsaturated fatty acid composition are monoacids which do not comprise any function other than the acid function and the carbon-carbon double bond.

Assignees

• Totalenergies Onetech

Inventors

• Crozet Delphine
• Limoges Alice
• Swoboda Benjamin

Classifications

• C07C69/675

  of saturated hydroxy-carboxylic acids · CPC title

• A61Q1/00

  Make-up preparations; Body powders; Preparations for removing make-up · CPC title

• A61K2800/10

  General cosmetic use · CPC title

• A61K8/361

  Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof · CPC title

• A61K8/34

  Alcohols · CPC title