# US 10,945,963 B2 · Photosensitive capsules and cosmetic and pharmaceutical use thereof

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- Number: US 10,945,963 B2
- Document ID: US10945963B2
- Status: Granted
- Kind: B2
- Application number: 15/025,098
- Filed: 2014-09-27
- Published: 2016-08-18
- Granted: 2021-03-16
- Earliest claimed: 2013-09-27
- Assignees: L'oreal
- Applicants: L'oreal
- Inventors: Andrew Greaves; Gleb Sukhorukov; Qiangying Yi
- Web page: https://patentgrep.com/patent/US10945963B2

## CPC

- A61K 9/5031: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)}
- A61K 8/11: Encapsulated compositions
- A61K 8/8194: {Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers}
- A61K 8/84: obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K 9/5073: {having two or more different coatings optionally including drug-containing subcoatings}
- A61Q 19/02: for chemically bleaching or whitening the skin
- A61K 2800/81: Preparation or application process involves irradiation
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

The invention relates to capsules of core/shell type, the core comprising an active agent; the shell comprising one or more concentric and alternating layers of a first photosensitive anionic amino polymer and of a second cationic polymer. The invention also relates to a cosmetic or pharmaceutical composition comprising such capsules. The invention also relates to a non-therapeutic cosmetic process for treating keratin materials, comprising the application to the keratin materials of a cosmetic composition comprising the said capsules, followed by exposure of the deposit formed on the keratin materials to natural light or to artificial light with a wavelength of between 360 and 600 nm.

## Claims

### Claim 1

Capsules of core/shell type, the core comprising an active agent;
comprising one or more concentric and alternating layers of a first photosensitive anionic polymer and of a second cationic polymer, wherein the first photosensitive anionic polymer is selected from the group of a substituted polyallylamine bearing primary amine groups substituted at a degree of substitution of at least 50% (numerical degree), with a group of formula (Ia) below:
in which:
R and R′ denote, independently, a hydrogen atom or a C1-C4 alkyl group or a C1-C4 alkoxy group, or a chlorine or fluorine atom or a nitro group;
R and R′ may together form a C6 aromatic ring;
Y denotes a —COOH or —SO3H group;
R″ and R″′ being such that:
when Y═—COOH, R″═R′″═H or R″═—OCH3 and R″═H or R″═OH and R′″═H or R″═Cl and R′″═H or R″═—CH3 and R′″═H or R″═OCH3 and R′″═OCH3 or R″═—NCO—CH3 and R″′═H or R″=isopropyl and R″′═CH3 or R″═H and R″′═F or R″=isopropyl and R″′═H;
when Y═—SO3H, R″═R″′═H or R″ and R″′ together form a C6 aromatic ring;
or salts thereof; and
poly{1-[4-(3-carboxy-4-hydroxyphenylazo)benzenesulfonamido]-1,2-ethanediyl or salts thereof;
and wherein the capsules are leaktight.

### Claim 2 (depends on 1)

Capsules according to claim 1, wherein the substituted polyallylamine has a degree of substitution of greater than 60%.

### Claim 3 (depends on 1)

Capsules according to claim 1, wherein the first polymer is poly{1-[4-(3-carboxy-4-hydroxyphenylazo)benzenesulfonamido]-1,2-ethanediyl, sodium salt}.

### Claim 4 (depends on 1)

Capsules according to claim 1, wherein the second cationic polymer is chosen from dimethyldiallylammonium chloride homopolymers.

### Claim 5 (depends on 1)

Capsules according to claim 1, wherein the first and second polymers are present in the capsules in a first polymer/second polymer weight ratio ranging from 0.5 to 1.5.

### Claim 6 (depends on 1)

Capsules according to claim 1, wherein the weight ratio of the first polymer plus the second polymer to the active agent ranges from 0.005 to 40.

### Claim 7 (depends on 1)

Capsules according to claim 1, wherein the core comprises an oil-in-water emulsifying surfactant when the active agent is liquid at room temperature and insoluble in water at 25° C. or when the active agent is solid at room temperature, insoluble in water and soluble in a water-immiscible organic solvent; all the conditions being at room temperature, 25° C.

### Claim 8 (depends on 1)

Capsules according to claim 1, wherein the core comprises one or more solid particles impregnated with the encapsulated active agent, and optionally a solvent to dissolve the encapsulated active agent when the active agent is a solid at room temperature.

### Claim 9 (depends on 8)

Capsules according to claim 8, wherein the particles are chosen from porous particles and hollow particles.

### Claim 10 (depends on 8)

Capsules according to claim 8, wherein the solid particles are chosen from silica, calcium carbonate, kaolin, talc, titanium dioxide, polyamide, (meth)acrylic polymer and glass particles.

### Claim 11 (depends on 8)

Capsules according to claim 8, wherein the solid particles have a mean size ranging from 10 nm to 50 μm.

### Claim 12 (depends on 1)

Capsules according to claim 1, wherein the capsules have a mean size ranging from 80 nm to 80 microns.

### Claim 13 (depends on 1)

Capsules according to claim 1, wherein the encapsulated active agent is chosen from fragrancing substances and cosmetic active agents.

### Claim 14 (depends on 13)

Cosmetic composition comprising, in a physiologically acceptable medium, capsules according to claim 13.

### Claim 15 (depends on 14)

Non-therapeutic cosmetic process for treating keratin materials, comprising the application to the keratin materials of a cosmetic composition according to claim 14, followed by exposure of the deposit formed on the keratin materials to natural light or to artificial light with a wavelength of between 360 and 600 nm.

### Claim 16 (depends on 1)

Capsules according to claim 1, wherein the encapsulated active agent is chosen from pharmaceutical active principles.

### Claim 17 (depends on 1)

Pharmaceutical composition comprising, in a physiologically acceptable medium, capsules according to claim 1, wherein the encapsulated active agent is chosen from pharmaceutical active principles.

### Claim 18 (depends on 1)

Capsules according to claim 1, wherein the second cationic polymer is selected from the group of homopolymers and copolymers of dimethyldiallylammonium salts and mixtures thereof.

### Claim 19 (depends on 1)

Capsules according to claim 1, wherein the first polymer is poly{1-[4-(3-carboxy-4-hydroxyphenylazo)benzenesulfonamido]-1,2-ethanediyl, sodium salt, the second cationic polymer is chosen from dimethyldiallylammonium chloride homopolymers, the first and second polymers are present in the capsules in a first polymer/second polymer weight ratio ranging from 0.5 to 1.5 and the encapsulated active agent is chosen from fragrancing substances.