Cosmetic process for attenuating wrinkles

Patent metadata

Field	Value
Publication number	US-10328014-B2
Application number	US-201515536320-A
Country	US
Kind code	B2
Filing date	Dec 10, 2015
Priority date	Dec 16, 2014
Publication date	Jun 25, 2019
Grant date	Jun 25, 2019

Abstract

The invention relates to a cosmetic process for caring for the skin, more particularly facial skin, in particular wrinkled skin, comprising the topical application to the skin of a cosmetic composition comprising a grafted polysaccharide polymer (I) and exposure of the treated skin to light radiation, polymer (I) being of formula:

PS—(CO—NH-L-X) a (COOH) b

in which PS denotes the basic backbone of the polysaccharide bearing the carboxylic acid groups;

L is a divalent hydrocarbon-based group containing from 1 to 20 carbon atoms;

X denotes a photoactive group of azide or diazirine type;

a denotes the content of COOH groups substituted with the group —NH-L-X;

b denotes the content of unsubstituted free COOH groups;

a being between 0.01 and 0.8; b being between 0.2 and 0.99;

a+b=1

The invention also relates to the polymers (I) bearing a photoactive group X of diazirine type and to a composition comprising such a polymer in a physiologically acceptable medium.

First claim

The invention claimed is:

1. A cosmetic process for caring for skin comprising:
(i) a step consisting in applying to the skin a cosmetic composition comprising, in a physiologically acceptable medium, at least 0.3% by weight, relative to the total weight of the composition, of a grafted polysaccharide polymer of formula:
PS—(CO—NH-L-X) a (COOH) b

in which PS denotes a basic backbone of a polysaccharide bearing carboxylic acid groups;
L is a linear, branched or cyclic, saturated or unsaturated divalent hydrocarbon-based group comprising from 1 to 20 carbon atoms, wherein said divalent hydrocarbon-based group may optionally be interrupted with one or more non-adjacent heteroatoms chosen from sulfur, oxygen, or a group chosen from —NH—, —COO—, —CONH—, —O—CO—NH— or —NH—CO—NH—, and wherein said divalent hydrocarbon-based group optionally comprises one or more groups chosen from hydroxyl, amine, thiol, carboxylic acid, amide and cyano groups;
X denotes an azide or diazirine photoactive group;
(a) denotes a content of COOH groups of the polysaccharide that are substituted with the group —NH-L-X;
(b) denotes a content of unsubstituted COOH groups of the polysaccharide;
(a) being between 0.01 and 0.8; (b) being between 0.2 and 0.99; and (a+b)=1; and
(ii) a step consisting in exposing the skin to light radiation.

2. The process according to claim 1 , wherein the polysaccharide comprises one or more base units chosen from uronic acid, glucuronic acid and mannuronic acid.

3. The process according to claim 1 , wherein the polysaccharide is chosen from hyaluronic acid, chondroitin, chondroitin sulfate, alginic acid, heparin, heparin sulfate and xanthan gum.

4. The process according to claim 1 , wherein the polysaccharide is hyaluronic acid.

5. The process according to claim 1 , wherein a (a) is between 0.1 and 0.6 and (b) is between 0.4 and 0.9.

6. The process according to claim 1 , wherein the group L is chosen from the following groups:

7. The process according to claim 1 , wherein the photoactive group X is chosen from the following groups:

wherein (*) represents the bond with the group L.

8. The process according to claim 1 , wherein the group X-L- is chosen from:

9. The process according to claim 1 , wherein the grafted polysaccharide polymer has a weight-average molecular weight ranging from 5,000 daltons to 1,000,000 daltons determined by liquid chromatography, using 0.1 M sodium chloride and 330 mg/l of sodium azide in water as eluent, with dextran as standard, and using Wyatt Optilab T-Rex refractometer and Wyatt Dawn-Heleos II light scattering detectors.

10. The process according to claim 1 , wherein the grafted polysaccharide polymer is present in the composition in a content ranging from 0.3% to 10% by weight, relative to the total weight of the composition.

11. The process according to claim 10 , wherein the step (ii) consisting in exposing the skin to light radiation is performed after or at the same time as the step (i) consisting in applying to the skin the cosmetic composition.

12. The process according to claim 10 , wherein the step (ii) consisting in exposing the skin to light radiation is performed after the step (i) consisting in applying to the skin the cosmetic composition.

13. The process according to claim 1 , wherein the light radiation is natural light or artificial light with a wavelength of between 360 nm and 600 nm.

14. The process according to claim 1 , in which the light radiation has a source chosen from arc lamps, fluorescent lamps, incandescent lamps, light emitting diodes and lasers.

15. The process according to claim 1 , wherein exposure time of the skin to the light radiation in step (ii) is at least 5 seconds.

16. The process according to claim 1 , wherein the composition is in the form of an oil-in-water emulsion or an aqueous gel.

17. The process according to claim 1 , wherein the cosmetic composition is applied to wrinkled skin for attenuating wrinkles.

18. A grafted polysaccharide polymer of formula:
PS—(CO—NH-L-X) a (COOH) b

in which PS denotes a basic backbone of a polysaccharide bearing carboxylic acid groups;
L is a linear, branched or cyclic, saturated or unsaturated divalent hydrocarbon-based group comprising from 1 to 20 carbon atoms, wherein said divalent hydrocarbon-based group may optionally be interrupted with one or more non-adjacent heteroatoms chosen from sulfur, oxygen, or a group chosen from —NH—, —COO—, —O—CO—NH— or —NH—CO—NH—, and wherein said divalent hydrocarbon-based group optionally comprises one or more groups chosen from hydroxyl, amine, thiol, carboxylic acid, amide and cyano groups;
X denotes a diazirine photoactive group;
(a) denotes a content of COOH groups of the polysaccharide that are substituted with the group —NH-L-X;
(b) denotes a content of unsubstituted COOH groups of the polysaccharide;
(a) being between 0.01 and 0.8; (b) being between 0.2 and 0.99, and (a+b)=1.

19. The grafted polysaccharide polymer according to claim 18 , wherein the polysaccharide comprises one or more base units chosen from uronic acid, glucuronic acid and mannuronic acid.

20. The grafted polysaccharide polymer according to claim 18 , wherein the polysaccharide is chosen from hyaluronic acid, chondroitin, chondroitin sulfate, alginic acid, heparin, heparin sulfate and xanthan gum.

21. The grafted polysaccharide polymer according to claim 18 , wherein the polysaccharide is hyaluronic acid.

22. The grafted polysaccharide polymer according to claim 18 , wherein a (a) is between 0.1 and 0.6 and (b) is between 0.4 and 0.9.

23. The grafted polysaccharide polymer according to claim 18 , wherein the group L is chosen from the following groups:

24. The grafted polysaccharide polymer according to claim 18 , wherein the photoactive group X may be chosen from the following groups:

wherein (*) represents the bond with the photoactive group L.

25. The grafted polysaccharide polymer according to claim 18 , wherein the group X-L- is chosen from:

26. The grafted polysaccharide polymer according to claim 18 , wherein the grafted polysaccharide polymer has a weight-average molecular weight ranging from 5,000 daltons to 1,000,000 daltons determined by liquid chromatography, using 0.1 M sodium chloride and 330 mg/l of sodium azide in water as eluent, with dextran as standard, and using Wyatt Optilab T-Rex refractometer and Wyatt Dawn-Heleos II light scattering detectors.

27. A composition comprising, in a physiologically acceptable medium, the grafted polysaccharide polymer according to claim 18 .

28. The composition ac

Assignees

• Oreal

Inventors

• Greaves Andrew

Classifications

• A61K8/73

  Polysaccharides · CPC title

• A61Q19/08

  Anti-ageing preparations · CPC title

• A61N2005/0651

  Diodes · CPC title

• C08B37/0084

  Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates · CPC title

• C08L5/08

  Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof · CPC title