Photoactive grafted polysaccharide and use thereof in cosmetics

Patent metadata

Field	Value
Publication number	US-10456607-B2
Application number	US-201515529215-A
Country	US
Kind code	B2
Filing date	Nov 30, 2015
Priority date	Nov 28, 2014
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

The invention also relates to a composition comprising the polymer (I) in a physiologically acceptable medium, and also to a cosmetic process for caring for the skin, comprising the topical application to the skin of said composition and exposure of the treated skin to light radiation.

First claim

The invention claimed is:

1. A polysaccharide polymer grafted with photoactive groups of an azide or diazirine of formula (I):
PS—(O—CO-L-X) a (OH) b   (I)

in which PS denotes the basic backbone of the polysaccharide bearing the hydroxyl groups;
L is a linear, branched or cyclic, saturated or unsaturated divalent hydrocarbon-based group comprising from 1 to 20 carbon atoms, which may be interrupted with one or more non-adjacent heteroatoms chosen from sulfur, oxygen, or —NH—, —COO—, —CONH—, —O—CO—NH— or —NH—CO—NH— groups, said divalent group optionally substituted with one or more groups chosen from hydroxyl, amine, thiol, carboxylic acid, amide, cyano, and acyl (C 1 -C 4 )amino groups;
X denotes the azide or diazirine photoactive group;
a denotes the content of OH groups substituted with the photoactive group;
b denotes the content of unsubstituted free OH groups;
a being between 0.02 and 0.5; b being between 0.5 and 0.98;
and a+b=1;
with the exception of compounds (I) for which:
PS is dextran and -L-X=—(CH 2 ) 5 —N 3
PS is hyaluronic acid and -L-X=—(CH 2 ) 3 —N 3 .

2. The polymer as claimed in claim 1 , wherein the polysaccharide comprises one or more base units chosen from uronic acid, glucuronic acid and mannuronic acid.

3. The polymer as claimed in claim 1 , wherein the polysaccharide is chosen from hyaluronic acid, chondroitin, chondroitin sulfate, alginic acid, heparin, heparin sulfate, xanthan gum, dextran and cellulose.

4. The polymer as claimed in claim 1 , wherein the polysaccharide is hyaluronic acid or alginic acid.

5. The polymer as claimed in claim 1 , wherein a is between 0.02 and 0.4 and b is between 0.6 and 0.98.

6. The polymer as claimed in claim 1 , wherein L is chosen from the following groups:

7. The polymer as claimed in claim 1 , wherein the photoactive group X is chosen from the following groups:

8. The polymer as claimed in that claim 1 , wherein the group X-L- is chosen from:

9. The polymer as claimed in claim 1 , wherein the polymer has a weight-average molecular weight ranging from 5000 daltons to 1,000,000 daltons as determined by liquid chromatography with 0.1 M sodium chloride and 330 mg/l of sodium azide in water as an eluent and dextran as the standard, using Wyatt Optilab T-Rex refractometer and Wyatt Dawn-Heleos II light scattering detectors.

10. A composition comprising, in a physiologically acceptable medium, a grafted polysaccharide (I) as claimed in claim 1 .

11. The composition as claimed in claim 10 the grafted polysaccharide (I) is present in a content ranging from 0.1% to 10% by weight, relative to the total weight of the composition.

12. The composition as claimed in claim 10 , which comprises a cosmetic adjuvant chosen from water, emulsifiers, preserving agents, sequestrants, fragrances, thickeners, oils, waxes and film-forming polymers.

13. The composition as claimed in claim 10 , which is in the form of an oil-in-water emulsion or an aqueous gel.

14. A cosmetic process for caring for the skin comprising:
(i) applying to the skin a composition comprising, in a physiologically acceptable medium, a grafted polysaccharide (I),
(ii) exposing the treated skin to light radiation,
the grafted polymer (I) being a polysaccharide polymer grafted with photoactive groups of an azide or diazirine of formula:
PS—(O—CO-L-X) a (OH) b   (I)

in which PS denotes the basic backbone of the polysaccharide bearing the hydroxyl groups;
L is a linear, branched or cyclic, saturated or unsaturated divalent hydrocarbon-based group comprising from 1 to 20 carbon atoms, which may be interrupted with one or more non-adjacent heteroatoms chosen from sulfur, oxygen, or —NH—, —COO—, —CONH—, —O—CO—NH— or —NH—CO—NH— groups, said divalent group being optionally substituted with one or more groups chosen from hydroxyl, amine, thiol, carboxylic acid, amide, cyano, and acyl (C 1 -C 4 )amino groups;
X denotes the azide or diazirine photoactive group;
a denotes the content of OH groups substituted with the photoactive group;
b denotes the content of unsubstituted free OH groups;
a being between 0.02 and 0.5; b being between 0.5 and 0.98;
and a+b=1.

15. The process as claimed in claim 14 , wherein the polysaccharide comprises one or more base units chosen from uronic acid, glucuronic acid and mannuronic acid.

16. The process as claimed in claim 14 , wherein the polysaccharide is chosen from hyaluronic acid, chondroitin, chondroitin sulfate, alginic acid, heparin, heparin sulfate, xanthan gum, dextran and cellulose.

17. The process as claim 14 , wherein the polysaccharide is hyaluronic acid or alginic acid.

18. The process as claimed in claim 14 , wherein a is between 0.02 and 0.4 and b is between 0.6 and 0.98.

19. The process as claimed in claim 14 , wherein L is chosen from the following groups:

20. The process as claimed in claim 14 , wherein the photoactive group X may be chosen from the following groups:

21. The process as claimed in claim 14 , wherein the group X-L- is chosen from:

22. The process as claimed in claim 14 , wherein it the polymer has a weight-average molecular weight ranging from 5000 daltons to 1,000,000 daltons as determined by liquid chromatography with 0.1 M sodium chloride and 330 mg/l of sodium azide in water as an eluent and dextran as the standard, using Wyatt Optilab T-Rex refractometer and Wyatt Dawn-Heleos II light scattering detectors.

23. The process as claimed in claim 14 , wherein the grafted polysaccharide (I) is present in a content ranging from 0.1% to 10% by weight, relative to the total weight of the composition.

24. The process as claimed in claim 14 , in which the step consisting in applying light radiation is performed after or at the same time as the step consisting in applying the cosmetic composition comprising the grafted polysaccharide (I).

25. The process as claimed in claim 14 , in which (ii) applying light radiation is performed after (i) applying the cosmetic composition comprising the grafted polysaccharide (I).

26. The process as claimed in claim 14 , wherein the light radiation is natural light or artificial light with a wavelength of between 360 nm and 600 nm.

27. The process as claimed in claim 14 , in which the light radiation has a source chosen from arc lamps; fluorescent lamps; incandescent lamps; light emitting diodes and lasers.

28. The process as claimed in claim 14 , in which the exposure time to t

Assignees

• Oreal

Inventors

• Greaves Andrew

Classifications

• A61K8/731

  Cellulose; Quaternized cellulose derivatives · CPC title

• C08B37/0072

  Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates · CPC title

• A61K8/73

  Polysaccharides · CPC title

• A61K8/735 Primary

  Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof · CPC title

• A61K2800/54

  Polymers characterized by specific structures/properties · CPC title