# US 11,992,546 B2 · Process of coloring keratinous material comprising the use of an organosilicon compound, an effect pigment, and a sealing reagent vi

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- Number: US 11,992,546 B2
- Document ID: US11992546B2
- Status: Granted
- Kind: B2
- Application number: 17/441,265
- Filed: 2020-03-13
- Published: 2022-05-19
- Granted: 2024-05-28
- Earliest claimed: 2019-03-19
- Assignees: Henkel AG & Co. KGaA
- Applicants: Henkel AG & Co. KGaA
- Inventors: Torsten Lechner; Gabriele Weser; Claudia Kolonko; Caroline Kriener; Ulrike Schumacher; Marc Nowottny; Juergen Schoepgens; Phillip Jaiser; Carsten Mathiaszyk
- Web page: https://patentgrep.com/patent/US11992546B2

## CPC

- A61K 8/585: {Organosilicon compounds}
- A61Q 5/065: {Preparations for temporary colouring the hair, e.g. direct dyes}
- A61K 8/0262: {Characterized by the central layer}
- A61K 8/26: Aluminium; Compounds thereof
- A61K 8/731: {Cellulose; Quaternized cellulose derivatives}
- A61K 8/8147: {Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers}
- A61K 8/8152: {Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers}
- A61K 8/891: saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61Q 5/06: Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61K 2800/412: Microsized, i.e. having sizes between 0.1 and 100 microns
- A61K 2800/54: Polymers characterized by specific structures/properties
- A61K 2800/5922: At least two compounds being classified in the same subclass of A61K8/18
- A61K 2800/623: Coating mediated by organosilicone compounds
- A61K 2800/884: Sequential application
- A61K 2800/94: Involves covalent bonding to the substrate
- 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

Provided herein is a process for dyeing keratinous material, in particular human hair, comprising the following steps: Application of an agent (a) to the keratinous material, wherein the agent (a) comprises: (a1) at least one organic silicon compound selected from the group of silanes having one, two or three silicon atoms, and (a2) at least one colorant compound comprising at least one substrate platelet-based pigment comprising a vacuum metallized pigment, and Application of an agent (b) to the keratinous material, wherein the agent (b) comprises: (b1) at least one sealing reagent.

## Claims

### Claim 1

A process for dyeing keratinous material comprising the following steps:
applying an agent (a) to the keratinous material, wherein the agent (a) comprises:
(a1) at least one organic silicon compound selected from the group of silanes having one, two or three silicon atoms, and
(a2) at least one colorant compound comprising at least one substrate platelet-based pigment comprising a vacuum metallized pigment, and
applying an agent (b) to the keratinous material, wherein the agent (b) comprises:
(b1) at least one sealing reagent.

### Claim 2 (depends on 1)

The process according to claim 1, wherein the agent (a) comprises at least one organic silicon compound (a1) of the formula (I) and/or (II)
R1R2N-L-Si(OR3)a(R4)b (I),
where
R1, R2 independently represent a hydrogen atom or a C1-C6 alkyl group,
L is a linear or branched divalent C1-C20 alkylene group,
R3, R4 independently of one another represent a C1-C6 alkyl group,
a, stands for an integer from 1 to 3, and
b stands for the integer 3-a, and
wherein in the organic silicon compound of formula (II)
(R5O)c(R6)d Si-(A)e-NR7-(A′)]f-[O-(A″)]g-[NR8-(A′″)]h-Si(R6′)d′(OR5′)c′ (II),
R5, R5′, R5″, 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 formula (III)
-(A″″)-Si(R6″)d″(OR5″)c″ (III),
c stands for an integer from 1 to 3,
d stands for the integer 3-c,
c″ stands ‘for an integer from 1 to 3,
d′ stands for the integer 3-c′,
c″ stands, for an integer from 1 to 3,
d″ stands for the integer 3-c″,
e stands for 0 or 1,
f stands for 0 or 1,
g stands for 0 or 1,
h stands for 0 or 1,
provided that at least one of e, f, g, and h is different from 0.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the agent (a) comprises at least one organic silicon compound (a1) of formula (I),
R1R2N-L-Si(OR3)a(R4)b (I),
where
R1, R2 both represent a hydrogen atom, and
L represents a linear, divalent C1-C6-alkylene group,
R3, R4 independently represent a methyl group or an ethyl group,
a stands for the number 3 and
b stands for the number 0.

### Claim 4 (depends on 2)

The process according to claim 2, wherein the agent (a) comprises at least one organic silicon compound (a1) of formula (I) selected from the group of
(3-Aminopropyl)triethoxysilane,
(3-Aminopropyl)trimethoxysilane,
-1-(3-Aminopropyl)silantriol,
(2-Aminoethyl)triethoxysilane,
(2-Aminoethyl)trimethoxysilane,
-1-(2-Aminoethyl)silantriol,
(3-Dimethylaminopropyl)triethoxysilane,
(3-Dimethylaminopropyl)trimethoxysilane,
-1-(3-Dimethylaminopropyl)silantriol,
(2-Dimethylaminoethyl)triethoxysilane,
(2-dimethylaminoethyl)trimethoxysilane, and/or
1-(2-Dimethylaminoethyl)silantriol.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the agent (a) comprises at least one organic silicon compound (a1) of formula (II),
(R5O)c(R6)d Si-(A)e-[NR7-(A′)]f-[O-(A″)]g-[NR8-(A′″)]h-Si(R6′)d′(OR5′)c′ (II),
where
e and f both stand for the number 1,
g and h both stand for the number 0,
A and A′ independently represent a linear, divalent C1-C6 alkylene 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)
-(A″″)-Si(R6″)d″(OR5″)c″ (III),
c stands for an integer from 1 to 3,
d stands for the integer 3-c,
c″ stands ‘for an integer from 1 to 3,
d′ stands for the integer 3-c′,
c″ stands, for an integer from 1 to 3,
d″ stands for the integer 3-c″,
e stands for 0 or 1,
f stands for 0 or 1,
g stands for 0 or 1,
h stands for 0 or 1,
provided that at least one of e, f, g, and h is different from 0.

### Claim 6 (depends on 2)

The process according to claim 2, wherein the agent (a) comprises at least one organic silicon compound (a1) of formula (II) selected from the group of
3-(Trimethoxysilyl)-N43-(trimethoxysilyl)propyl]-1-propanamine,
3-(Triethoxysilyl)-N-[3-(triethoxysilyl) propyl]-1-propanamine,
N-Methyl-3-(trimethoxysilyl)-N43-(trimethoxysilyl)propyl]-1-propanamine,
N-Methyl-3-(triethoxysilyl)-N43-(triethoxysilyl)propyl]-1-propane amine,
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, and/or
N,N-bis[3-(triethoxysilyl)propyl]-2-propen-1-amine.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the agent (a) comprises at least one organic silicon compound (a1) of formula (IV),
R9Si(OR10)k(R11)m (IV),
where
R9 stands for a C1-C18 is 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.

### Claim 8 (depends on 7)

The process according to claim 7, wherein the agent (a) comprises at least one organic silicon compound (a1) of formula (IV) selected from the group of:
Methyltrimethoxysilane,
Methyltriethoxysilane,
Ethyltrimethoxysilane,
Ethyltriethoxysilane,
Hexyltrimethoxysilane,
Hexyltriethoxysilane,
Octyltrimethoxysilane,
Octyltriethoxysilane,
Dodecyltrimethoxysilane,
Dodecyltriethoxysilane,
Octadecyltrimethoxysilane,
Octadecyltriethoxysilane, and
Mixtures of these.

### Claim 9 (depends on 1)

The process according to claim 1, wherein the agent (a) comprises at least two structurally different organic silicon compounds (a1).

### Claim 10 (depends on 1)

The process according to claim 1, wherein the substrate platelet comprises a material selected from the group of metals, metal alloys and metal oxides.

### Claim 11 (depends on 1)

The process of claim 1, wherein the substrate platelet comprises aluminum.

### Claim 12 (depends on 1)

The process according to claim 1, wherein the substrate platelet comprises a coating A of at least one low refractive index metal oxide and/or metal oxide hydrate having a refractive index of at most about 1.8.

### Claim 13 (depends on 1)

The process according to claim 1, wherein the substrate platelet comprises a coating B of at least one highly refractive metal oxide having a refractive index of at least about 1.9.

### Claim 14

The process according to 13, wherein the substrate platelet has a further coating C of at least one metal oxide and/or metal oxide hydrate which is different from the underlying coating B.

### Claim 15

A kit-of-parts for dyeing keratinous material, comprising separately packaged
a first container comprising an agent (a′), wherein the agent (a′) comprises:
(a1) at least one organic silicon compound selected from the group of silanes having one, two or three silicon atoms, and
a second container comprising an agent (a″), the agent (a″) comprising:
(a2) at least one colorant compound comprising at least one substrate platelet-based pigment comprising a vacuum metallized pigment,
a third container containing an agent (b), wherein the agent (b) comprises:
(b1) at least one sealing reagent.

### Claim 16 (depends on 3)

The process according to claim 3, wherein L represents a propylene group (—CH2—CH2—CH2—) or an ethylene group (—CH2—CH2—).

### Claim 17 (depends on 1)

The process according to claim 1, wherein the agent (a) comprises at least one organic silicon compound (a1) of formula (I),
R1R2N-L-Si(OR3)a(R4)b (I),
where
R1, R2 both represent a hydrogen atom, and
L represents a linear, divalent C1-C6-alkylene group,
R3, R4 independently represent a methyl group or an ethyl group,
a stands for the number 3 and
b stands for the number 0, and at least one organic silicone compound (a1) of formula (IV),
R9Si(OR10)k(R11)m (IV),
where
R9 stands for 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.

### Claim 18 (depends on 1)

The process according to claim 1, wherein the at least one at least one sealing reagent (b1) comprises a compound selected from the group of film-forming polymers, alkalizing agents, acidifying agents, and mixtures thereof.

### Claim 19 (depends on 18)

The process according to claim 18, wherein the at least one at least one sealing reagent (b1) comprises a film-forming polymer.

### Claim 20 (depends on 19)

The process according to claim 19, wherein the at least one at least one sealing reagent (b1) comprises an ethylene/sodium acrylate copolymer.