# US 11,439,578 B2 · Agent for dyeing hair, containing at least one organic silicon compound, a coloring compound and a film-forming, hydrophilic polymer

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- Number: US 11,439,578 B2
- Document ID: US11439578B2
- Status: Granted
- Kind: B2
- Application number: 17/052,085
- Filed: 2019-03-21
- Published: 2021-11-25
- Granted: 2022-09-13
- Earliest claimed: 2018-03-07
- Assignees: Henkel AG & Co. KGaA
- Applicants: Henkel AG & Co. KGaA
- Inventors: Torsten Lechner; Marc Nowottny; Juergen Schoepgens
- Web page: https://patentgrep.com/patent/US11439578B2

## CPC

- A61K 8/585: {Organosilicon compounds}
- A61K 8/26: Aluminium; Compounds thereof
- A61K 8/342: {Alcohols having more than seven atoms in an unbroken chain}
- A61K 8/345: {containing more than one hydroxy group}
- A61K 8/365: Hydroxycarboxylic acids; Ketocarboxylic acids
- A61K 8/375: {the alcohol moiety containing more than one hydroxy group}
- A61K 8/39: Derivatives containing from 2 to 10 oxyalkylene groups
- A61K 8/442: {substituted by amido group(s)}
- A61K 8/8164: {Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)}
- A61K 8/8176: {Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers}
- A61K 8/8182: {Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers}
- A61Q 5/10: Preparations for permanently dyeing the hair
- A61Q 5/12: Preparations containing hair conditioners
- A61K 2800/4324: in preparations for permanently dyeing the hair
- A61K 2800/436: Interference pigments, e.g. Iridescent, Pearlescent
- A61K 2800/87: Application Devices; Containers; Packaging
- 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 subject of the present disclosure is a composition for coloring keratinous material, in particular human hair, containing in a cosmetic carrier (a) at least one organic silicon compound selected from silanes having one, two or three silicon atoms, said organic silicon compound further comprising one or more basic chemical functions and one or more hydroxyl groups or hydrolysable groups per molecule, (b) at least one colorant compound from the group of pigments and/or direct dyes, and (c) at least one film-forming hydrophilic polymer.

## Claims

### Claim 1

A composition for dyeing keratinous material, comprising in a cosmetic carrier
(a) at least one organic silicon compound selected from silanes having one, two or three silicon atoms, said organic silicon compound further comprising one or more basic chemical functions and one or more hydroxyl groups or hydrolysable groups per molecule,
(b) at least one colorant compound selected from the group of pigments, direct dyes, and combinations thereof, and
(c) at least one film-forming hydrophilic polymer, wherein the film-forming hydrophilic polymer has a solubility in water at a temperature 25 degrees Celsius and a pressure of 760 millimeters of mercury of more than 1% by weight.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein the composition comprises (a) at least one organic silicon compound of formula (I) and/or (II),
R1R2N-L-Si(OR3)a(R4)b (I),
where
R1, and R2 independently represent a hydrogen atom or a C1-C6 alkyl group,
L is a linear or branched divalent C1-C20 alkylene group,
R3 represents a hydrogen atom or a C1-C6 alkyl group,
R4 represents a C1-C6 alkyl group,
a, stands for an integer from 1 to 3, and
b stands for the integer 3-a,
(R5O)c(R6)dSi-(A)c-[NR7-(A′)]f-[O-(A″)]g-[NR8-(A′″)]h—Si(R6′)d′(OR5′)c′ (II),
where
R5, R5′, and 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′, and A″, independently of one another represent a linear or branched divalent C1-C20alkylene 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),
where
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 composition according to claim 1, wherein the composition comprises (a) at least one organic silicon compound of the 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.

### Claim 4 (depends on 2)

The composition according to claim 2, wherein the composition comprises (a) at least one organic silicon compound of the formula (I),
where
R3, R4 independently of one another represent a methyl group or an ethyl group and
a stands for the number 3 and
b stands for the number 0.

### Claim 5 (depends on 2)

The composition according to claim 2 wherein the composition comprises (a) at least one organic silicon compound of the formula (I) which is 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,
1-(2-Dimethylaminoethyl)silantriol, and combinations thereof.

### Claim 6 (depends on 2)

The composition according to claim 2, wherein the composition comprises (a) at least one organic silicon compound of formula (II),
where
R5 and R5′ independently represent a methyl group or an ethyl group,
c and c′ both stand for the number 3 and
d and d′ both stand for the number 0.

### Claim 7 (depends on 2)

The composition according to claim 2, wherein the composition comprises (a) at least one organic silicon compound of formula (II),
(R5O)c(R6)dSi-(A)c-[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 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 8 (depends on 2)

The composition according to claim 2, wherein the composition comprises (a) at least one organic silicon compound of the formula (II) which is selected from the group 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 combinations thereof.

### Claim 9 (depends on 1)

The composition according to claim 1, wherein the film-forming hydrophilic polymer has a solubility in water at the temperature 25 degrees Celsius and the pressure of 760 millimeters of mercury of more than 2% by weight.

### Claim 10 (depends on 9)

The composition according to claim 9, wherein the film-forming hydrophilic polymer comprises polyvinylpyrrolidone (PVP).

### Claim 11 (depends on 10)

The composition according to claim 10, wherein the polyvinylpyrrolidone (PVP) has a molecular weight of about 40,000 g/mol.

### Claim 12

A multicomponent packaging unit (kit-of-parts) for dyeing keratinous material comprising:
a first container containing a cosmetic product (I),
a second container containing a cosmetic product (II), and
a third container containing a cosmetic product (III),
where
the cosmetic product (I) comprises at least one organic silicon compound (a) selected from silanes having one, two or three silicon atoms, said organic silicon compound further comprising one or more basic chemical functions and one or more hydroxyl groups or hydrolysable groups per molecule,
the cosmetic product (II) comprises water, and
the cosmetic product (III) comprises at least one colorant compound (b) selected from the group of pigments, direct dyes, and combinations thereof, and at least one film-forming hydrophilic polymer (c), wherein the at least one film-forming hydrophilic polymer has a solubility of more than 1% by weight in water at a temperature of 25 degrees Celsius and a pressure of 760 millimeters of mercury.

### Claim 13 (depends on 12)

The multicomponent packaging unit (kit-of-parts) according to claim 12, wherein the at least one film-forming hydrophilic polymer (c) comprises polyvinylpyrrolidone (PVP) with a solubility of more than 2% by weight in water at the temperature of 25 degrees Celsius and the pressure of 760 millimeters of mercury.

### Claim 14 (depends on 13)

The multicomponent packaging unit (kit-of-parts) according to claim 13, wherein the cosmetic product (III) comprises the polyvinylpyrrolidone (PVP) in an amount of 9% by weight, based on a total weigh of the cosmetic product (III).

### Claim 15 (depends on 14)

The multicomponent packaging unit (kit-of-parts) according to claim 14, wherein the polyvinylpyrrolidone (PVP) has a molecular weight of about 40,000 g/mol.

### Claim 16 (depends on 1)

The agent according to claim 1, wherein the at least one film-forming hydrophilic polymer (c) is selected from the group of polyvinylpyrrolidone (PVP), vinylpyrrolidone/vinyl acetate copolymers, vinylpyrrolidone/styrene copolymers, Vinylpyrrolidone/ethylene copolymers, vinylpyrrolidone/propylene copolymers, vinylpyrrolidone/vinyl caprolactam copolymers, vinylpyrrolidone/vinyl formamide copolymers, vinylpyrrolidone/vinyl alcohol copolymers, and combinations thereof.

### Claim 17

A method for dyeing keratinous material comprising the following steps in the order indicated:
(1) applying a pretreatment agent (V) to the keratinous material, the pretreatment agent (V) comprising, in a water-containing cosmetic carrier, at least one organic silicon compound (a) selected from silanes having one, two or three silicon atoms, said organic silicon compound further comprising one or more basic chemical functions and one or more hydroxyl groups or hydrolysable groups per molecule, and
(2) applying a coloring agent (F) to the keratinous material, the coloring agent comprising at least one colorant compound (b) selected from the group of pigments, direct dyes, and combinations thereof, and at least one film-forming hydrophilic polymer (c), wherein the at least one film-forming hydrophilic polymer has a solubility of more than 1% by weight in water at a temperature of 25 degrees Celsius and a pressure of 760 millimeters of mercury.

### Claim 18 (depends on 17)

The method according to claim 17, further comprising: mixing a first agent (I) and a second agent (II) to produce the pre-treatment agent (V) before application on the keratinous material, wherein
the first agent (I) comprises the least one organic silicon compound (a),
the second agent (II) comprises water,
the at least one film-forming hydrophilic polymer has a solubility of more than 2% by weight in water at a temperature of 25 degrees Celsius and a pressure of 760 millimeters of mercury, the at least one film-forming hydrophilic polymer comprises polyvinylpyrrolidone (PVP), and
the coloring agent (F) comprises the polyvinylpyrrolidone (PVP) in an amount of 9 weight percent, based on a total weight of the coloring agent (F).

### Claim 19 (depends on 17)

A method according to claim 17, comprising the following steps in the order indicated
(1) applying the pre-treatment agent (V) onto the keratinous material,
(2) allowing the pre-treatment agent (V) to act for a period of from about 10 seconds to about 10 minutes,
(3) optionally rinsing out the pre-treatment agent (V),
(4) applying the coloring agent (F) onto the keratinous material,
(5) allowing the coloring agent (F) to react for a period of from about 30 seconds to about 30 minutes and
(6) optionally applying a conditioner, and
(7) rinsing the keratinous material.

### Claim 20 (depends on 19)

The method according to claim 19, wherein the conditioner comprises at least one cationic and/or non-ionic surfactant.