# US 2014/0155352 A1 · Cosmetic treatment processes and kit

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0155352 A1
- Document ID: US20140155352A1
- Status: Published application
- Kind: A1
- Application number: 14/130,597
- Filed: 2012-07-09
- Published: 2014-06-05
- Earliest claimed: 2011-07-07
- Assignees: L'oreal
- Inventors: Anne-Claude Dublanchet; Christian Blaise
- Web page: https://patentgrep.com/patent/US20140155352A1

## CPC

- A61K 8/4953: {containing pyrimidine ring derivatives, e.g. minoxidil}
- A61K 8/4926: {having six membered rings}
- A61K 8/4966: {Triazines or their condensed derivatives}
- A61K 8/585: {Organosilicon compounds}
- A61Q 3/00: Manicure or pedicure preparations
- A61Q 5/00: Preparations for care of the hair
- A61Q 5/10: Preparations for permanently dyeing the hair
- A61Q 5/12: Preparations containing hair conditioners
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- A61Q 19/00: Preparations for care of the skin
- A61K 2800/43: Pigments; Dyes
- A61K 2800/884: Sequential application
- 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 present invention relates to a cosmetic process for treating keratin materials, which can give them, especially in a long-lasting and reversible manner, interesting cosmetic properties; this process comprising the application to said materials: in a first stage, of a cosmetic composition comprising at least one graftable species, comprising at least one unit of formula (Ia): and in a second stage, of a cosmetic composition comprising at least one cosmetic active agent bearing at least one unit of formula (Ia): The invention also relates to a kit comprising said compositions.

## Claims

### Claim 1

A cosmetic process for treating keratin materials, comprising the application to said materials:
in a first stage, of a cosmetic composition comprising at least one graftable species, comprising at least one unit of formula (Ia):
and in a second stage, of a cosmetic composition comprising at least one cosmetic active agent bearing at least one unit of formula (Ia):

### Claim 2

A cosmetic process for treating keratin materials, comprising the application to said materials of a cosmetic composition comprising, as a mixture:
at least one graftable species, comprising at least one unit of formula (Ia):
and at least one cosmetic active agent bearing at least one unit of formula (Ia):

### Claim 3 (depends on 1)

The process as claimed in claim 1, in which the graftable species bearing the unit (Ia) is chosen from the compounds of formula (II), and salts and solvates thereof:
in which:
X represents a linear or branched, saturated or unsaturated, divalent C1-C30 hydrocarbon-based chain, optionally interrupted with and/or bearing, at one or both of its ends, one or more divalent groups chosen from —N(R)—, —N+(R)(R′)—, —O—, —S—, —C(O)—, —SO2—, and an aromatic or non-aromatic, saturated or unsaturated, fused or non-fused divalent C3-C7 (hetero)cyclic radical, optionally comprising one or more identical or different heteroatoms chosen from N, S and O, optionally substituted with OH or NR″R′″;
with R and R′, which may be identical or different, chosen from a hydrogen, a linear or branched, saturated or unsaturated C1-C4 alkyl radical, optionally substituted with OH and/or NR″R′″,
with R″ and R′″, which may be identical or different, chosen from H or a linear or branched, saturated or unsaturated C1-C4 alkyl radical;
p is equal to 0 or 1;
q is equal to 0 or 1;
Y represents a linear, branched and/or cyclic, saturated or unsaturated divalent C1-C18 hydrocarbon-based chain, optionally substituted with OH and/or NR″R′″,
W represents a unit for grafting onto keratin materials.

### Claim 4 (depends on 1)

The process as claimed in claim 1, in which W represents:
(i) a thiol,
(ii) a protected thiol of formula —S—Pr with Pr representing:
a) a protecting group such as a saturated or unsaturated, fused or non-fused, aromatic or non-aromatic C5-C6 heterocycle, optionally comprising N, O, S and/or P heteroatoms;
b) an sp2 carbon protecting group;
c) an sp3 carbon protecting group;
d) a metal protecting group;
e) a substituted sulfur atom protecting group,
f) a photosensitive protecting group;
(iii) a nucleofugal group;
(iv) a group containing one or more activated carbons or activated bonds;
(v) a group containing one or more siloxanes

### Claim 5 (depends on 1)

The process as claimed in claim 1, in which the graftable species bearing the unit (Ia) is chosen from the following compounds:

### Claim 6 (depends on 1)

The process as claimed in claim 1, in which the graftable species bearing the unit (Ia) is in an amount of from 0.1% to 10% by weight in the composition comprising it.

### Claim 7 (depends on 1)

The process as claimed in claim 1, in which the cosmetic active agent bearing at least one unit of formula (Ia) is chosen from the following compounds, alone or as a mixture:
cosmetic active agents for caring for keratin fibers;
dyeing active agents, especially direct dyes and fluorescent dyes;
polymeric hydrophilic chains;
silicone chains;
fatty substances;
UV-screening agents;
hyaluronic acid;
capsules;
it being understood that these cosmetic active agents bear at least one unit of formula (Ia).

### Claim 8 (depends on 1)

The process as claimed in claim 1, in which the cosmetic active agent is a cosmetic active agent for caring for keratin fibers of formula (III), and also the salts, addition salts, isomers, solvates, especially hydrates, and tautomeric forms thereof:
in which:
R1=H and R2=methyl; and
Z represents a monovalent radical chosen from:
(i) a linear or branched C9 to C32 (saturated) alkyl radical;
(ii) a linear or branched C9 to C32 (unsaturated) alkene radical;
said radicals optionally being substituted with 1 to 8 groups chosen from —OH, —OR, —SO3H, —SO3R, —SO2NRR′, —COOH, —NRR′ and —N+RR′R″, with R, R′ and R″=H or C1-C6 alkyl; and/or said radicals optionally comprising 1 to 8 divalent groups chosen, alone or as a mixture, from —NH— (or ═NH), —O—, —C(O)—, —C(═NH)—, —N+(CH3)2-An− (An−: anion); or alternatively —N=(trivalent).

### Claim 9 (depends on 1)

The process as claimed in claim 1, in which the cosmetic active agent is a supramolecular oil, which is obtainable by reaction between:
on the one hand, at least one oil bearing at least one nucleophilic and/or electrophilic reactive function, and
on the other hand, at least one junction group capable of establishing hydrogen bonds with one or more partner junction groups, each junction group pairing involving at least 3 hydrogen bonds, said junction group bearing at least one reactive function capable of reacting with the reactive function borne by the oil, said junction group comprising at least one unit of formula (I′) or (II′):
in which:
R1 and R3, which may be identical or different, represent a divalent carbon-based radical chosen from (i) a linear or branched C1-C32 alkyl group, (ii) a C4-C16 cycloalkyl group and (iii) a C4-C16 aryl group; optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si and P; and/or optionally substituted with an ester or amide function or with a C1-C12 alkyl radical; or a mixture of these groups;
R2 represents CH3.

### Claim 10 (depends on 1)

The process as claimed in claim 1, in which the cosmetic active agent is a supramolecular wax, which is obtainable by reaction between:
at least one wax bearing at least one reactive function chosen from OH and COOH, or even anhydride, and
at least one junction group capable of establishing hydrogen bonds with one or more partner junction groups, each junction group pairing involving at least 4 hydrogen bonds, said junction group bearing at least one “complementary” reactive function capable of reacting with the reactive function borne by the wax, said junction group comprising at least one unit of formula (I′) or (II′):
in which:
R1 and R3, which may be identical or different, represent a divalent carbon-based radical chosen from (i) a linear or branched C1-C32 alkyl group, (ii) a C4-C16 cycloalkyl group and (iii) a C4-C16 aryl group; optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si and P; and/or optionally substituted with an ester or amide function or with a C1-C12 alkyl radical; or a mixture of these groups;
R2 represents CH3.

### Claim 11 (depends on 1)

The process as claimed in claim 1, in which the cosmetic active agent is a UV-screening agent of formula (Ib) or (IIb) below:
in which:
n=1, 2 or 3;
m=0 or 1;
w=0 or 1; the value of w is conditioned by the nature of the groups A1 and A2 as specifically mentioned in the definition of said groups;
with the condition that when w=0, then the radical A1 and the diradical A2 cannot end with a nitrogen;
q=0 or 1; the value of q is conditioned by the nature of the groups A1 and A2 as specifically mentioned in the definition of said groups;
R1=methyl and R2=H;
Z represents a multivalent radical (divalent to tetravalent, depending on the value of n) chosen from:
(i) a linear or branched, saturated or unsaturated C1-C32 carbon-based and especially hydrocarbon-based radical; optionally interrupted or substituted, one or more times, with an optionally aromatic C3-C12 (hetero)cycle; or
(ii) an optionally aromatic C3-C12 carbon-based and especially hydrocarbon-based (hetero)cyclic radical; optionally substituted with one or more linear or branched, saturated or unsaturated C1-C32 carbon-based and especially hydrocarbon-based radicals;
(iii) a radical —(C5-C6)cycloalkyl(C1-C12)alkyl-
said radical Z possibly being:
(1) substituted with 1 to 12 identical or different groups chosen from —OH, —SO3R, —OSO3R, —SO3H, —OSO3H, —COOH, —COOR, —CONRR′, C1-C4 alkyl and —N+RR′R″, An−
and/or
(2) interrupted or terminated with 1 to 5 identical or different groups chosen from the divalent groups: —S—, —NH— (or ═NH), —O—, —C(O)—, —SO2—, or combinations thereof, for instance —NHC(O)—, —C(O)NH—, —OC(O)—, —C(O)O—, or
with Ra=H or halogen, especially Cl, or C1-C6 alkyl; and R, R′ and R″, which may be identical or different, being H or a linear or branched C1-C12 alkyl radical; it being understood that said radical Z comprises at least one heteroatom chosen from N, O and S; when Z is interrupted or substituted with a cationic group, the electrical neutrality of the compounds of formula (Ib) is ensured by a cosmetically acceptable anion or mixture of anions An−;
Z may also denote a covalent bond for the compounds of formula (Ib) when n=1 and q=0, Z′1 not being able to denote a covalent bond;
Z1 and Z′1, which may be identical or different, denote a divalent radical Z; Z′1 not being able to denote a covalent bond;
Z2 is a linear or branched divalent C1-C32 alkyl radical;
the monoradicals A1 corresponding to one of the formulae (IIIa) to (XIIa) below:
a) para-aminobenzoate:
b) cinnamate, benzalmalonate or cyanoacrylate:
it being understood that:
q=w=x=1 when Z is not a covalent bond, and
q=x=0 when Z is a covalent bond
c) benzophenone:
d) benzylidenecamphor:
e) benzotriazole:
with X═O or NH
Ak=linear saturated divalent C1-C6, preferably C2, alkyl radical.
f) s-triazine:
with the radicals A3, which may be identical or different, representing the radicals A1 of formula (IIIa), (IVa), (Va), (VIa) or (IXa);
the diradicals A2 corresponding to one of the formulae (IIIb) to (VIIb) below:
a/ para-aminobenzoate:
with X═O or NH
b/ cinnamate, benzalmalonate or cyanoacrylate:
with X═O or NH
c/ benzophenone:
d/ benzylidenecamphor:
e/ s-triazine:
with A4 representing a radical of formula (IIIa), (IVa), (Va), (VIa) or (IXa);
in which:
R1 represents a linear or branched C1-C30 alkyl or C3-C30 alkenyl radical, which may bear one or more hydroxyl substituents and which may contain in the carbon-based chain an alkyl ring, one or more heteroatoms chosen from oxygen, nitrogen and silicon atoms, an optionally substituted C6-C20 aryl radical;
R2 and R′2 represent, independently, a linear or branched C1-C10 alkoxy radical, a linear or branched C1-C10 alkyl radical, a linear or branched C2-C8 alkenyl radical or —OSi(CH3)3, two adjacent radicals R2 together optionally forming an alkylidenedioxy group in which the alkylidene group contains from 1 to 2 carbon atoms (i.e. a group —O—(CH2)t—O— with t=1 or 2),
p and p′ are, independently, 0, 1 or 2,
R3 is hydrogen, a C1-C4 alkyl radical, or a radical chosen from
—(C═O)XR1, —CN, —(C═O)R1, —SO2R4 with R1 having the same definition as above and
R4 represents a linear or branched C1-C12 alkyl radical or a C6-C20 aryl radical, which is optionally substituted,
R5 represents a divalent C2-C8 alkyl radical,
X represents oxygen or a radical —NR6 with R6 being a linear or branched C1-C8 alkyl radical.

### Claim 12 (depends on 1)

The process as claimed in claim 1, in which the cosmetic active agent is a capsule which is obtainable by reaction between:
on the one hand, at least one preformed capsule, bearing at least one reactive function, especially at the surface, said reactive function possibly being nucleophilic or electrophilic, and
on the other hand, at least one junction group capable of establishing hydrogen bonds with one or more partner junction groups, each junction group pairing involving at least 3 hydrogen bonds, said junction group bearing at least one reactive function capable of reacting with the reactive function borne by said capsule, said junction group comprising at least one unit of formula (I′) or (II′):
in which:
R1 and R3, which may be identical or different, represent a divalent carbon-based radical chosen from (i) a linear or branched C1-C32 alkyl group, (ii) a C4-C16 cycloalkyl group and (iii) a C4-C16 aryl group; optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si and P; and/or optionally substituted with an ester or amide function or with a C1-C12 alkyl radical; or a mixture of these groups;
R2 represents a methyl radical.

### Claim 13 (depends on 1)

The process as claimed in claim 1, in which the cosmetic active agent bearing at least one unit of formula (Ia), or the mixture of such active agents, is present in the composition in an amount of from 0.01% to 50% by weight relative to the total weight of the composition.

### Claim 14

A kit comprising, firstly, a cosmetic composition comprising at least one graftable species comprising at least one unit of formula (Ia), and, secondly, a second cosmetic composition comprising at least one cosmetic active agent bearing at least one unit of formula (Ia):
each composition being packaged in a packaging assembly.

### Claim 15 (depends on 2)

The process as claimed in claim 2, in which the graftable species bearing the unit (Ia) is chosen from the compounds of formula (II), and salts and solvates thereof:
in which:
X represents a linear or branched, saturated or unsaturated, divalent C1-C30 hydrocarbon-based chain, optionally interrupted with and/or bearing, at one or both of its ends, one or more divalent groups chosen from —N(R)—, —N+(R)(R′)—, —O—, —S—, —C(O)—, —SO2—, and an aromatic or non-aromatic, saturated or unsaturated, fused or non-fused divalent C3-C7 (hetero)cyclic radical, optionally comprising one or more identical or different heteroatoms chosen from N, S and O, optionally substituted with OH or NR″R′″;
with R and R′, which may be identical or different, chosen from a hydrogen, a linear or branched, saturated or unsaturated C1-C4 alkyl radical, optionally substituted with OH and/or NR″R′″,
with R″ and R′″, which may be identical or different, chosen from H or a linear or branched, saturated or unsaturated C1-C4 alkyl radical;
p is equal to 0 or 1;
q is equal to 0 or 1;
Y represents a linear, branched and/or cyclic, saturated or unsaturated divalent C1-C18 hydrocarbon-based chain, optionally substituted with OH and/or NR″R′″,
W represents a unit for grafting onto keratin materials.

### Claim 16 (depends on 2)

The process as claimed in claim 2, in which W represents:
(i) a thiol,
(ii) a protected thiol of formula —S—Pr with Pr representing:
a) a protecting group such as a saturated or unsaturated, fused or non-fused, aromatic or non-aromatic C5-C6 heterocycle, optionally comprising N, O, S and/or P heteroatoms;
b) an sp2 carbon protecting group;
c) an sp3 carbon protecting group;
d) a metal protecting group;
e) a substituted sulfur atom protecting group,
f) a photosensitive protecting group;
(iii) a nucleofugal group;
(iv) a group containing one or more activated carbons or activated bonds;
(v) a group containing one or more siloxanes.

### Claim 17 (depends on 3)

The process as claimed in claim 3, in which W represents:
(i) a thiol,
(ii) a protected thiol of formula —S—Pr with Pr representing:
a) a protecting group such as a saturated or unsaturated, fused or non-fused, aromatic or non-aromatic C5-C6 heterocycle, optionally comprising N, O, S and/or P heteroatoms;
b) an sp2 carbon protecting group;
c) an sp3 carbon protecting group;
d) a metal protecting group;
e) a substituted sulfur atom protecting group,
f) a photosensitive protecting group;
(iii) a nucleofugal group;
(iv) a group containing one or more activated carbons or activated bonds;
(v) a group containing one or more siloxanes.

### Claim 18 (depends on 2)

The process as claimed in claim 2, in which the graftable species bearing the unit (Ia) is chosen from the following compounds:

### Claim 19 (depends on 3)

The process as claimed in claim 3, in which the graftable species bearing the unit (Ia) is chosen from the following compounds:

### Claim 20 (depends on 4)

The process as claimed in claim 4, in which the graftable species bearing the unit (Ia) is chosen from the following compounds: