# US 2011/0236341 A1 · Cosmetic method using a composition containing siloxane resins and a non-volatile oil

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- Number: US 2011/0236341 A1
- Document ID: US20110236341A1
- Status: Published application
- Kind: A1
- Application number: 13/132,195
- Filed: 2009-12-02
- Published: 2011-09-29
- Earliest claimed: 2008-12-02
- Assignees: L'oreal
- Inventors: Florence Dop
- Web page: https://patentgrep.com/patent/US20110236341A1

## CPC

- A61K 8/585: {Organosilicon compounds}
- A61K 8/06: Emulsions
- A61K 8/064: {Water-in-oil emulsions, e.g. Water-in-silicone emulsions}
- A61K 8/891: saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K 8/894: modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
- A61Q 1/02: Preparations containing skin colorants, e.g. pigments (preparations in powder form A61Q1/12)
- A61Q 1/06: Lipsticks
- A61Q 1/10: for eyes, e.g. eyeliner, mascara
- A61Q 1/12: Face or body powders for grooming, adorning or absorbing
- A61K 2800/594: Mixtures of polymers
- 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 a cosmetic method for making-up and/or caring for keratin materials, in particular the skin, whereby a cosmetic composition is applied to the keratin materials, said cosmetic composition taking the form of an emulsion and comprising siloxane resins and a non-volatile hydrocarbon oil. In particular, the invention relates to compositions used to care for or make-up the aforementioned keratin materials.

## Claims

### Claim 1

A cosmetic method for making up and/or caring for keratin materials, comprising applying, to said keratin materials a composition, in the form of an emulsion, wherein the composition comprises, in a physiologically acceptable medium:
a) a siloxane resin comprising at least 80 mol % of units:
(R′3SiO1/2)a (hereinafter “M” units) and
(ii) (SiO4/2)b (hereinafter “Q” units)
in which
R′ independently represents an alkyl group containing from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group,
with the condition that at least 95 mol % of the R′ groups are alkyl groups,
a and b are values strictly greater than 0,
and the ratio a/b is between 0.5 and 1.5;
b) a propyl silsesquioxane resin comprising at least 80 mol % of (R″SiO3/2) units (hereinafter “T” units) in which R″ independently represents an alkyl group comprising from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group, with the condition that at least 80 mol % of the R″ groups are propyl groups;
the weight ratio between the resins a) and b) being between 1/99 and 99/1, in particular between 85/15 and 15/85,
the resins a) and b) not being bonded to one another via covalent bonds,
and the number of M units in the final mixture being strictly less than the number of (T+Q) units;
and
c) at least one non-volatile C6-C22 hydrocarbon-based oil.

### Claim 2

A cosmetic method for making up and/or caring for keratin materials, comprising applying, to said keratin materials, of a composition comprising, in a physiologically acceptable medium:
a) a siloxane resin comprising at least 80 mol % of units:
(R′3SiO1/2)a (hereinafter “M” units) and
(ii) (SiO4/2)b (hereinafter “Q” units)
in which
R′ independently represents an alkyl group containing from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group,
with the condition that at least 95 mol % of the R′ groups are alkyl groups,
a and b are values strictly greater than 0,
and the ratio a/b is between 0.5 and 1.5;
b) a film-forming propyl silsesquioxane resin comprising at least 80 mol % of (R″SiO3/2) units (hereinafter “T” units) in which R″ independently represents an alkyl group containing comprising from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group, with the condition that at least 40 mol % of the R″ groups are propyl groups,
the weight ratio between the resins a) and b) being between 1/99 and 99/1, in particular between 85/15 and 15/85,
the resins a) and b) not being bonded to one another via covalent bonds,
and the number of M units in the final mixture being strictly less than the number of (T+Q) units;
and
c) at least one non-volatile C6-C22 hydrocarbon-based oil.

### Claim 3 (depends on 1)

The method as claimed in claim 1, wherein the siloxane and propyl silsesquioxane resins a) and b) are formulated in the composition via a mixture that can be obtained from a process comprising:
mixing a solution of siloxane resin with a solution of propyl silsesquioxane resin, then
heating, under the following specific conditions:
heating uniformly for at least one hour, preferably between 1 h and 5 h, at a single temperature or at temperature holds of between 90° C. and 250° C.;
provided that this heating is carried out without the presence of a catalyst for chemical condensation between the two resins.

### Claim 4 (depends on 1)

The method as claimed in claim 1, wherein said composition is an inverse or direct emulsion or a multiple emulsion, preferably an inverse emulsion.

### Claim 5 (depends on 1)

The method as claimed in claim 1, wherein said composition comprises an amount of siloxane resins a) and b), with respect to active material (dry matter), ranging from 0.5% to 35% by weight, relative to the total weight of the composition.

### Claim 6 (depends on 1)

The method as claimed in claim 1, wherein the non-volatile C6-C22 hydrocarbon-based oil is chosen from:
carbonates, of following formula (I): R1-O—C(═O)—O—R′1, with R1 and R′1, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C 12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring;
monoesters, of formula (II): R2-O—C(═O)—R′2, with R2 and R′2, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring;
diesters, of following formula (III): R3-O—C(═O)—R′3-C(═O)—O—R″3, with R3 and R″3, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C12, and preferentially C5 to C 10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring, and R′3 representing a saturated or unsaturated, C1 to C4, preferably C2 to C4, alkyl chain, for instance an alkylene chain derived from succinic, maleate, glutarate or adipate; in particular, R3 and R″3 are chosen from isobutyl, pentyl, neopentyl, hexyl, heptyl, neoheptyl, 2-ethylhexyl, octyl, nonyl and isononyl;
ethers, of following formula (IV): R4-O—R4′, with R4 and R4′, which may be identical or different, representing a linear or branched, saturated or unsaturated, C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring; in particular, R4 and R4′ are chosen from isobutyl, pentyl, neopentyl, hexyl, heptyl, neoheptyl, 2-ethylhexyl, octyl, nonyl and isononyl;
alkyl triesters, of formula (V): R5-O—C(O)—CH2—CH[—O—C(O)—R′5]—CH2—O—C(O)—R″5, with R5, R′5 and R″5, which may be identical or different, representing a linear or branched, saturated or unsaturated, C4-C10 alkyl chain;
diesters, of following formula (VI): R3-C(═O)—O—R′3-O—C(═O)—R″3, with R3 and R″3, which may be identical or different, representing a linear or branched, saturated or unsaturated, (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain, and R′3 representing a saturated or unsaturated, C1 to C4, preferably C2 to C4, alkylene chain, in particular 1,3-propanediol dicaprylate,
and mixtures thereof.

### Claim 7 (depends on 1)

The method as claimed in claim 1, wherein the non-volatile C6-C22 hydrocarbon-based oil is selected from the group consisting of dicaprylyl carbonate, bis(2-ethylhexyl) carbonate, diisobutyryl carbonate, dineopentyl carbonate, dipentyl carbonate, dineoheptyl carbonate, diheptyl carbonate, diisononyl carbonate, dinonyl carbonate, 2-ethylhexyl isobutyrate, 2-ethylhexyl butyrate, caprylyl butyrate, isononyl isobutyrate, 2-ethylhexyl hexanoate, isononyl hexanoate, neopentyl hexanoate, caprylyl heptanoate, octyl octanoate, isononyl isononanoate, dicaprylyl maleate, bis(2-ethylhexyl) succinate, dicaprylyl ether, caprylic/capric triglyceride, and mixtures thereof.

### Claim 8 (depends on 1)

The method as claimed in claim 1, wherein the non-volatile C6-C22 hydrocarbon-based oil is present in a content ranging from 1% to 60% by weight, relative to the total weight of the composition.

### Claim 9 (depends on 1)

The method as claimed in claim 1, wherein the composition also comprises at least one compound selected from the group consisting of an oil, a nonionic surfactant, an amphiphilic silicone elastomer, a pasty compound of nonanimal origin, a fatty-phase thickening or gelling rheological agent, a wax, a hydrophilic gelling agent, a filler, a dyestuff, a film-forming polymer, an ionic surfactant, a fiber, and mixtures thereof.

### Claim 10 (depends on 1)

A composition for making up and/or caring for keratin fibers, that can be used in a method as claimed in claim 1, in the form of an emulsion, comprising, in a physiologically acceptable medium, the siloxane resins a) and b) and at least one non-volatile C6-C22 hydrocarbon-based oil chosen from:
carbonates, of following formula (I): R1-O—C(═O)—O—R′1, with R1 and R′1, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring;
monoesters, of formula (II): R2-O—C(═O)—R′2, with R2 and R′2, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring;
diesters, of following formula (III): R3-O—C(═O)—R′3-C(═O)—O—R″3, with R3 and R″3, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring, and R′3 representing a saturated or unsaturated, C1 to C4, preferably C2 to C4, alkyl chain, for instance an alkylene chain derived from succinic, maleate, glutarate or adipate; in particular, R3 and R″3 are chosen from isobutyl, pentyl, neopentyl, hexyl, heptyl, neoheptyl, 2-ethylhexyl, octyl, nonyl and isononyl;
ethers, of following formula (IV): R4-O—R4′, with R4 and R4′, which may be identical or different, representing a linear or branched, saturated or unsaturated, C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring; in particular, R4 and R4′ are chosen from isobutyl, pentyl, neopentyl, hexyl, heptyl, neoheptyl, 2-ethylhexyl, octyl, nonyl and isononyl;
alkyl triesters, of formula (V): R5-O—C(O)—CH2—CH[—O—C(O)—R′5]—CH2—O—C(O)—R″5, with R5, R′5 and R″5, which may be identical or different, representing a linear or branched, saturated or unsaturated, C4-C10 alkyl chain;
diesters, of following formula (VI): R3-C(═O)—O—R′3-O—C(═O)—R″3, with R3 and R″3, which may be identical or different, representing a linear or branched, saturated or unsaturated, (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain, and R′3 representing a saturated or unsaturated, C1 to C4, preferably C2 to C4, alkylene chain, in particular 1,3-propanediol dicaprylate,
and mixtures thereof.

### Claim 11 (depends on 10)

The composition as claimed in claim 10, wherein the siloxane resin comprises at least 80 mol % of units:
(i) (R′3SiO1/2)a (hereinafter “M” units) and
(ii) (SiO4/2)b (hereinafter “Q” units)
in which
R′ independently represents an alkyl group containing from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group,
with the condition that at least 95 mol % of the R′ groups are alkyl groups,
a and b are values strictly greater than 0,
and the ratio a/b is between 0.5 and 1.5.

### Claim 12 (depends on 10)

The composition as claimed in claim 10, wherein said composition is an inverse or direct emulsion or a multiple emulsion.

### Claim 13 (depends on 10)

A cosmetic assembly comprising:
a container delimiting at least one compartment, said container being closed by means of a closing member; and
a composition placed inside said compartment, the composition being defined as claimed in claim 10.

### Claim 14 (depends on 13)

The cosmetic assembly as defined in claim 13, further comprising an applicator in the form of a block of foam or elastomer, a felt or a spatula.

### Claim 15 (depends on 2)

The method as claimed in claim 2, wherein the siloxane and propyl silsesquioxane resins a) and b) are formulated in the composition via a mixture that can be obtained from a process comprising:
mixing a solution of siloxane resin with a solution of propyl silsesquioxane resin, then
heating, under the following specific conditions:
heating uniformly for at least one hour, preferably between 1 h and 5 h, at a single temperature or at temperature holds of between 90° C. and 250° C.;
provided that this heating is carried out without the presence of a catalyst for chemical condensation between the two resins.

### Claim 16 (depends on 2)

The method as claimed in claim 2, wherein said composition is an inverse or direct emulsion or a multiple emulsion.

### Claim 17 (depends on 2)

The method as claimed in claim 2, wherein said composition comprises an amount of siloxane resins a) and b), with respect to active material (dry matter), ranging from 0.5% to 35% by weight, relative to the total weight of the composition.

### Claim 18 (depends on 2)

The method as claimed in claim 2, wherein the non-volatile C6-C22 hydrocarbon-based oil is chosen from:
carbonates, of following formula (I): R1-O—C(═O)—O—R′1, with R1 and R′1, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C 12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring;
monoesters, of formula (II): R2-O—C(═O)—R′2, with R2 and R′2, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C 12, and preferentially C5 to C 10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring;
diesters, of following formula (III): R3-O—C(═O)—R′3-C(═O)—O—R″3, with R3 and R″3, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring, and R′3 representing a saturated or unsaturated, C1 to C4, preferably C2 to C4, alkyl chain, for instance an alkylene chain derived from succinic, maleate, glutarate or adipate; in particular, R3 and R″3 are chosen from isobutyl, pentyl, neopentyl, hexyl, heptyl, neoheptyl, 2-ethylhexyl, octyl, nonyl and isononyl;
ethers, of following formula (IV): R4-O—R4′, with R4 and R4′, which may be identical or different, representing a linear or branched, saturated or unsaturated, C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring; in particular, R4 and R4′ are chosen from isobutyl, pentyl, neopentyl, hexyl, heptyl, neoheptyl, 2-ethylhexyl, octyl, nonyl and isononyl;
alkyl triesters, of formula (V): R5-O—C(O)—CH2—CH[—O—C(O)—R′5]—CH2—O—C(O)—R″5, with R5, R′5 and R″5, which may be identical or different, representing a linear or branched, saturated or unsaturated, C4-C10 alkyl chain;
diesters, of following formula (VI): R3-C(═O)—O—R′3-O—C(═O)—R″3, with R3 and R″3, which may be identical or different, representing a linear or branched, saturated or unsaturated, (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain, and R′3 representing a saturated or unsaturated, C1 to C4, preferably C2 to C4, alkylene chain, in particular 1,3-propanediol dicaprylate,
and mixtures thereof.

### Claim 19 (depends on 2)

The method as claimed in claim 2, wherein the non-volatile C6-C22 hydrocarbon-based oil is selected from the group consisting of dicaprylyl carbonate, bis(2-ethylhexyl) carbonate, diisobutyryl carbonate, dineopentyl carbonate, dipentyl carbonate, dineoheptyl carbonate, diheptyl carbonate, diisononyl carbonate, dinonyl carbonate, 2-ethylhexyl isobutyrate, 2-ethylhexyl butyrate, caprylyl butyrate, isononyl isobutyrate, 2-ethylhexyl hexanoate, isononyl hexanoate, neopentyl hexanoate, caprylyl heptanoate, octyl octanoate, isononyl isononanoate, dicaprylyl maleate, bis(2-ethylhexyl) succinate, dicaprylyl ether, caprylic/capric triglyceride, and mixtures thereof.

### Claim 20 (depends on 2)

The method as claimed in claim 2, wherein the non-volatile C6-C22 hydrocarbon-based oil is present in a content ranging from 1% to 60% by weight, relative to the total weight of the composition.

### Claim 21 (depends on 2)

The method as claimed in claim 2, wherein the composition further comprises at least one compound selected from the group consisting of an oil, a nonionic surfactant, an amphiphilic silicone elastomer, a pasty compound of nonanimal origin, a fatty-phase thickening or gelling rheological agent, a wax, a hydrophilic gelling agent, a filler, a dyestuff, a film-forming polymer, an ionic surfactant, a fiber, and mixtures thereof.

### Claim 22 (depends on 2)

A composition for making up and/or caring for keratin fibers, that can be used in a method as claimed in claim 2, in the form of an emulsion, comprising, in a physiologically acceptable medium, the siloxane resins a) and b) and at least one non-volatile C6-C22 hydrocarbon-based oil chosen from:
carbonates, of following formula (I): R1-O—C(═O)—O—R′1, with R1 and R′1, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring;
monoesters, of formula (II): R2-O—C(═O)—R′2, with R2 and R′2, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C 12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring;
diesters, of following formula (III): R3-O—C(═O)—R′3-C(═O)—O—R″3, with R3 and R″3, which may be identical or different, representing a linear or branched, saturated or unsaturated (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring, and R′3 representing a saturated or unsaturated, C1 to C4, preferably C2 to C4, alkyl chain, for instance an alkylene chain derived from succinic, maleate, glutarate or adipate; in particular, R3 and R″3 are chosen from isobutyl, pentyl, neopentyl, hexyl, heptyl, neoheptyl, 2-ethylhexyl, octyl, nonyl and isononyl;
ethers, of following formula (IV): R4-O—R4′, with R4 and R4′, which may be identical or different, representing a linear or branched, saturated or unsaturated, C4 to C12, and preferentially C5 to C10, alkyl chain optionally having at least one saturated or unsaturated, preferably saturated, ring; in particular, R4 and R4′ are chosen from isobutyl, pentyl, neopentyl, hexyl, heptyl, neoheptyl, 2-ethylhexyl, octyl, nonyl and isononyl;
alkyl triesters, of formula (V): R5-O—C(O)—CH2—CH[—O—C(O)—R′5]—CH2—O—C(O)—R″5, with R5, R′5 and R″5, which may be identical or different, representing a linear or branched, saturated or unsaturated, C4-C10 alkyl chain;
diesters, of following formula (VI): R3-C(═O)—O—R′3-O—C(═O)—R″3, with R3 and R″3, which may be identical or different, representing a linear or branched, saturated or unsaturated, (preferably saturated), C4 to C12, and preferentially C5 to C10, alkyl chain, and R′3 representing a saturated or unsaturated, C1 to C4, preferably C2 to C4, alkylene chain, in particular 1,3-propanediol dicaprylate,
and mixtures thereof.

### Claim 23 (depends on 2)

The composition as claimed in claim 2, wherein the siloxane resin comprises at least 80 mol % of units:
(i) (R′3SiO1/2)a (hereinafter “M” units) and
(ii) (SiO4/2)b (hereinafter “Q” units)
in which
R′ independently represents an alkyl group containing from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group,
with the condition that at least 95 mol % of the R′ groups are alkyl groups,
a and b are values strictly greater than 0,
and the ratio a/b is between 0.5 and 1.5.

### Claim 24 (depends on 2)

The composition as claimed in claim 2, wherein said composition is an inverse or direct emulsion or a multiple emulsion.

### Claim 25 (depends on 2)

A cosmetic assembly comprising:
a container delimiting at least one compartment, said container being closed by means of a closing member; and
a composition placed inside said compartment, the composition being defined as claimed in claim 2.

### Claim 26 (depends on 25)

The cosmetic assembly as defined in claim 25, also comprising an applicator in the form of a block of foam or elastomer, a felt or a spatula.