# US 11,998,629 B2 · Method for dyeing keratinous material, comprising the use of an organosilicon compound, an effect pigment and a film-forming polymer

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

- Number: US 11,998,629 B2
- Document ID: US11998629B2
- Status: Granted
- Kind: B2
- Application number: 17/762,027
- Filed: 2020-08-25
- Published: 2022-10-27
- Granted: 2024-06-04
- Earliest claimed: 2019-09-18
- Assignees: Henkel AG & Co. KGaA
- Applicants: Henkel AG & Co. KGaA
- Inventors: Rene Krohn; Thomas Hippe; Stefan Hoepfner; Jessica Brender
- Web page: https://patentgrep.com/patent/US11998629B2

## CPC

- A61K 8/585: {Organosilicon compounds}
- A61K 8/0262: {Characterized by the central layer}
- A61K 8/26: Aluminium; Compounds thereof
- A61K 8/29: Titanium; Compounds thereof
- A61K 8/365: Hydroxycarboxylic acids; Ketocarboxylic acids
- A61K 8/8158: {Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers}
- A61K 8/8176: {Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers}
- A61Q 5/065: {Preparations for temporary colouring the hair, e.g. direct dyes}
- A61Q 5/10: Preparations for permanently dyeing the hair
- A61K 2800/43: Pigments; Dyes
- A61K 2800/436: Interference pigments, e.g. Iridescent, Pearlescent
- A61K 2800/884: Sequential application
- A61K 2800/95: Involves in-situ formation or cross-linking 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

A method and a kit-of-parts are provided for dyeing keratinous material. The method includes applying a first agent to the keratinous material and applying an second agent to the keratinous material. The first agent includes at least one organic silicon compound. The second agent comprises at least one colorant compound and at least one film-forming polymer. The colorant compound includes at least one effect pigment including a substrate platelet including synthetic mica. The colorant compound further includes a coating including at least a first metal oxide (hydrate) layer.

## Claims

### Claim 1

A method for dyeing keratinous material, comprising the following steps:
applying a first agent (a) to the keratinous material, wherein the first agent (a) comprises:
(a1) at least one organic silicon compound of the formula (I) and at least one organic silicon compound of the formula (IV),
where in the organic silicon compound of the formula (I):
R1R2N-L-Si(OR3)a(R4)b (I),
R1, R2 independently represent a hydrogen atom or a C1-C6-Alkyl group,
L represents a linear or branched divalent C1-C20-alkylene group,
R3 represents a hydrogen atom or for a C1-C6-Alkyl group,
R4 represents a C1-C6-Alkyl group,
a represents an integer from 1 to 3, and
b stands for the integer 3−a, and
where in the organic silicon compound of the formula (IV):
R9Si(OR10)k(R11)m (IV),
R9 represents a C1-C18-alkyl group,
R10 represents a hydrogen atom or a C1-C6-alkyl group,
R11 represents a C1-C6-alkyl group,
k is an integer from 1 to 3, and
m stands for the integer 3−k, and
applying a second agent (b) to the keratinous material, wherein the second agent (b) comprises:
(b1) at least one colorant compound comprising at least one effect pigment comprising a substrate platelet comprising synthetic mica, and a coating comprising at least a first metal oxide (hydrate) layer, and
(b2) at least one film-forming polymer.

### Claim 2 (depends on 1)

The method according to claim 1, wherein
R1 and R2 each represent a hydrogen atom,
L represents a propylene group (—CH2—CH2—CH2—) or an ethylene group (—CH2—CH2—),
R3 represents a hydrogen atom, an ethyl group, or a methyl group,
R4 represents a methyl group or an ethyl group,
a represents the number 3, and
b represents the number 0.

### Claim 3 (depends on 1)

The method of claim 1, wherein the first agent (a) further comprises at least one organic silicon compound of the formula (II)
(R5O)c(R6)dSi-(A)e-[NR7-(A′)]f-[O-(A″)]g-[NR8-(A′″)]h-Si(R6′)d′(OR5′)c′ (II),
where
R5, R5′, R5″ independently represent a hydrogen atom or a C1-C6-Alkyl group,
R6, R6′ and R6″ independently represent a C1-C6-Alkyl group,
A, A′, A″, A′″ and A″″ independently represent a linear or branched divalent C1-C20-alkylene group,
R7 and R8 independently represent a hydrogen atom, a C1-C6 alkyl group, a hydroxy-C1-C6 alkyl group, a C2-C6-Alkenyl group, an amino-C1-C6-alkyl group or a group of the formula (III):
(A″″)-Si(R6″)d″(OR5″)c″ (III),
where
c represents an integer from 1 to 3,
d represents the integer 3−c,
c′ represents an integer from 1 to 3,
d′ represents the integer 3−c′,
c″ represents an integer from 1 to 3,
d″ represents the integer 3−c″,
e represents 0 or 1,
f represents 0 or 1,
g represents 0 or 1,
h represents 0 or 1,
wherein at least one of the residues from e, f, g and h is different from 0.

### Claim 4 (depends on 1)

The method of claim 1, wherein
R1 and R2 each represent a hydrogen atom,
L represents a linear, divalent C1-C6 alkylene group,
R3 represents a hydrogen atom, an ethyl group, or a methyl group,
R4 represents a methyl group or an ethyl group,
a represents the number 3, and
b represents the number 0.

### Claim 5 (depends on 1)

The method of claim 1, wherein the first agent (a) comprises at least one organic silicon compound of formula (I) selected from the group consisting of:
(3-Aminopropyl)triethoxysilane;
(3-Aminopropyl)trimethoxysilane;
1-(3-aminopropyl)silanetriol;
(2-Aminoethyl)triethoxysilane;
(2-Aminoethyl)trimethoxysilane;
1-(2-aminoethyl)silanetriol;
(3-Dimethylaminopropyl)triethoxysilane;
(3-Dimethylaminopropyl)trimethoxysilane;
1-(3-Dimethylaminopropyl)silanetriol;
(2-dimethylaminoethyl)triethoxysilane;
(2-dimethylaminoethyl)trimethoxysilane;
1-(2-dimethylaminoethyl)silanetriol; and
Mixtures thereof.

### Claim 6 (depends on 3)

The method of claim 3, wherein the first agent (a) further comprises at least one organic silicon compound of the formula (II),
(R5O)c(R6)dSi-(A)e-[NR7-(A′)]f-[O-(A″)]g-[NR8-(A′″)h-Si(R6′)d′(OR5′)c′′ (II),
where
e and f both represent the number 1,
g and h both represent the number 0,
A and A′ independently represent a linear, divalent C1-C6 alkylene group, and
R7 represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a group of formula (III).

### Claim 7 (depends on 3)

The method of claim 3, wherein the at least one organic silicon compound of formula (II) is selected from the group consisting of:
3-(Trimethoxysilyl)-N-[3-(trimethoxysilyl)propyl]-1-propanamine;
3-(Triethoxysilyl)-N-[3-(triethoxysilyl)propyl]-1-propanamine;
N-methyl-3-(trimethoxysilyl)-N-[3-(trimethoxysilyl)propyl]-1-propanamine;
N-methyl-3-(triethoxysilyl)-N-[3-(triethoxysilyl)propyl]-1-propanamine;
2-[Bis[3-(trimethoxysilyl)propyl]amino]ethanol;
2-[Bis[3-(triethoxysilyl)propyl]amino]ethanol;
3-(Trimethoxysilyl)-N,N-bis[3-(trimethoxysilyl)propyl]-1-propanamine;
3-(triethoxysilyl)-N,N-bis[3-(triethoxysilyl)propyl]-1-propanamine;
N1,N1-bis[3-(trimethoxysilyl)propyl]-1,2-ethanediamine;
N1,N1-bis[3-(triethoxysilyl)propyl]-1,2-ethanediamine;
N,N-bis[3-(trimethoxysilyl)propyl]-2-propen-1-amine;
N,N-bis[3-(triethoxysilyl)propyl]-2-propen-1-amine; and
Mixtures thereof.

### Claim 8 (depends on 1)

The method of claim 1, wherein the at least one organic silicon compound of formula (IV) is selected from the group consisting of:
Methyltrimethoxysilane;
Methyltriethoxysilane;
Ethyltrimethoxysilane;
Ethyltriethoxysilane;
Propyltrimethoxysilane;
Propyltriethoxysilane;
Hexyltrimethoxysilane;
Hexyltriethoxysilane;
Octyltrimethoxysilane;
Octyltriethoxysilane;
Dodecyltrimethoxysilane;
Dodecyltriethoxysilane;
Octadecyltrimethoxysilane;
Octadecyltriethoxysilane; and
Mixtures thereof.

### Claim 9 (depends on 1)

The method of claim 1, wherein the first metal oxide (hydrate) layer comprises titanium dioxide (TiO2).

### Claim 10 (depends on 1)

The method of claim 1, wherein the coating further comprises a second metal oxide (hydrate) layer.

### Claim 11 (depends on 10)

The method of claim 10, wherein the second metal oxide (hydrate) layer is a metal oxide (hydrate) selected from the group consisting of tin oxide (SnO2), silicon oxide (SiO2), aluminum oxide (Al2O3), Iron oxide (Fe2O3 and/or Fe3O4), and mixtures thereof.

### Claim 12 (depends on 10)

The method of claim 10, wherein the second metal oxide (hydrate) layer comprises tin oxide (SnO2).

### Claim 13 (depends on 1)

The method of claim 1, wherein the first agent (a) further comprises at least one coloring compound (a2), which is selected from the group of colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates, bronze pigments, colored pigments based on mica coated with at least one metal oxide, and colored pigments based on mica coated with a metal oxychloride.

### Claim 14

A multi-component packaging unit (kit-of-parts) for dyeing keratinous material, comprising separately assembled
a first container comprising a first agent (a), wherein the first agent (a) comprises at least one organic silicon compound of the formula (I) and at least one organic silicon compound of the formula (IV),
where in the organic silicon compound of the formula (I):
R1R2N-L-Si(OR3)a(R4)b (I),
R1, R2 independently represent a hydrogen atom or a C1-C6-Alkyl group,
L represents a linear or branched divalent C1-C20-alkylene group,
R3 represents a hydrogen atom or for a C1-C6-Alkyl group,
R4 represents a C1-C6-Alkyl group,
a represents an integer from 1 to 3, and
b stands for the integer 3−a, and
where in the organic silicon compound of the formula (IV):
R9Si(OR10)k(R11)m (IV),
R9 represents a C1-C18-alkyl group,
R10 represents a hydrogen atom or a C1-C6-alkyl group,
R11 represents a C1-C6-alkyl group,
k is an integer from 1 to 3, and
m stands for the integer 3−k, and
a second container containing a second agent (b), wherein the second agent (b) comprises: (b 1) at least one colorant compound comprising at least one effect pigment comprising a substrate platelet comprising synthetic mica, and a coating comprising at least a first metal oxide (hydrate) layer, and
(b2) at least one film-forming polymer.