Agent for dyeing keratin material, containing at least two organosilicon compounds that are different from each other, at least one pigment and at least one liquid fatty component and/or a solvent

Patent metadata

Field	Value
Publication number	US-12329840-B2
Application number	US-202218272368-A
Country	US
Kind code	B2
Filing date	Jan 12, 2022
Priority date	Feb 5, 2021
Publication date	Jun 17, 2025
Grant date	Jun 17, 2025

Abstract

An agent for dyeing keratin material, such as human hair, may include at least two organosilicon compounds different from each other. Each organosilicon compound may be independently selected from silanes with one, two, or three silicon atoms, and the organosilicon compound may include one or more hydroxyl groups and/or hydrolyzable groups per molecule. The agent may include at least one pigment, and at least one fatty component that is liquid at 20° C. and/or an organic solvent. The agent may be used for dyeing keratin material.

First claim

The invention claimed is:

1. An agent for dyeing keratin material, the agent comprising:
at least two organosilicon compounds, wherein each organosilicon compound is a silane with one, two, or three silicon atoms that comprises one or more hydroxyl groups and/or hydrolyzable groups per molecule;
at least one pigment;
at least one fatty component that is a liquid at 20° C. and/or an organic solvent; and
water in an amount ranging from 0 to 25.0 wt. %, based on the total weight of the agent.

2. The agent of claim 1 , wherein the at least two organosilicon compounds comprise at least one first organosilicon compound of formula (I) and/or (II):
R 1 R 2 N-L-Si(OR 3 ) a (R 4 ) b   (I)

wherein: R 1 and R 2 are each, independently, a hydrogen atom or a C 1 -C 6 alkyl group, L is a linear or branched divalent C 1 -C 20 alkylene group, R 3 and R 4 are each, independently, a C 1 -C 6 alkyl group, a is 1, 2 or 3, and b is 3-a, and
(R 5 O) c (R 6 ) d Si—(A) e —[NR 7 —(A′)] f —[O—(A″)] g —[NR 8 —(A′″)] h —Si(R 6 ′) d′ (OR 5 ′) c′   (II)

wherein:
R 5 , R 5 ′, R 5 ″, R 6 , R 6 ′ and R 6 ″ represent are each, independently, of one another, a C 1 -C 6 alkyl group,
A, A′, A″, A′″ and A″″ are each, independently, a linear or branched, divalent C 1 -C 20 alkylene group,
R 7 and R 8 are each, independently, a hydrogen atom, a C 1 -C 6 alkyl group, a hydroxy C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, an amino C 1 -C 6 alkyl group, or a group of formula (III):
(A″″)-Si(R 6 ″) d ″(OR 5 ″) c ″  (III)

wherein:
c is 1, 2 or 3,
d is 3-c,
c′ is 1, 2 or 3,
d′ is 3-c′,
c″ is 1, 2 or 3,
d″ is 3-c′,
e is 0 or 1,
f is 0 or 1,
g is 0 or 1, and
h is 0 or 1,
with the proviso that at least one of e, f, g and h is not 0.

3. The agent of claim 2 , wherein the at least one first organosilicon compound of formula (I) is represented by:
R 1 R 2 N-L-Si(OR 3 ) a (R 4 ) b   (I)

wherein:
R 1 and R 2 are both hydrogen atom,
L is a linear, divalent C 1 -C 6 alkylene group,
R 3 and R 4 are each, independently, a methyl group or an ethyl group,
a is 3, and
b is 0.

4. The agent of claim 2 , wherein the at least one first organosilicon compound of formula (I) is selected from the group consisting of:
(3-aminopropyl) trimethoxysilane,
(3-aminopropyl)triethoxysilane,
(2-aminoethyl)trimethoxysilane,
(2-aminoethyl)triethoxysilane,
(3-dimethylaminopropyl) trimethoxysilane,
(3-dimethylaminopropyl)triethoxysilane,
(2-dimethylaminoethyl)trimethoxysilane,
(2-dimethylaminoethyl)triethoxysilane, and
any combination thereof.

5. The agent of claim 2 , wherein the at least one first organosilicon compound of formula (II) is represented by:
(R 5 O) c (R 6 ) d Si—(A) e —[NR 7 —(A′)] f —[O—(A″)] g —[NR 8 —(A′″)] h —Si(R 6 ′) d′ (OR 5 ′) c′   (II)

wherein:
e and f are both 1,
g and h are both 0,
A and A′ are each, independently, a linear, divalent C 1 -C 6 alkylene group, and
R 7 represents R 7 is a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group, or a group of formula (III).

6. The agent of claim 2 , wherein the at least one first organosilicon 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
any combination thereof.

7. The agent to of claim 1 , wherein the at least two organosilicon compounds comprise at least one second organosilicon compound of formula (IV):
R 9 Si(OR 10 ) k (R 11 ) m   (IV)

wherein:
R 9 is a C 1 -C 12 alkyl group,
R 10 is a hydrogen atom or a C 1 -C 6 alkyl group,
R 11 is a C 1 -C 6 alkyl group,
k is 1, 2 or 3, and
m is 3-k.

8. The agent of claim 7 , wherein the at least one second organosilicon compound of formula (IV) is selected from the group consisting of:
methyltrimethoxysilane,
methyltriethoxysilane,
ethyltrimethoxysilane,
ethyltriethoxysilane,
hexyltrimethoxysilane,
hexyltriethoxysilane,
octyltrimethoxysilane,
octyltriethoxysilane,
dodecyltrimethoxysilane,
dodecyltriethoxysilane, and
combinations any combination thereof.

9. The agent of claim 2 , wherein the at least one first organosilicon compound is present in an amount ranging from 0.1 to 99.0 wt. %, based on the total weight of the agent.

10. The agent to of claim 7 , wherein the at least one second organosilicon compound is present in an amount ranging from 0.1 to 99.0 wt. %, based on the total weight of the agent.

11. The agent of claim 1 , wherein the at least one pigment is selected from the group consisting of colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulphates, bronze pigments, mica-based colored pigments coated with at least one metal oxide, metal oxychloride oxychlorides, and any combination thereof.

12. The agent of claim 1 , wherein the at least one pigment is selected from the group consisting of carmine, quinacridone, phthalocyanine, sorghum, blue pigments with the Color Index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, or CI 74160, yellow pigments with the Color Index numbers CI 11680, CI 11710, CI 15985, CI 19140, CI 20040, CI 21100, CI 21108, CI 47000, or CI 47005, green pigments with the Color Index numbers CI 61565, CI 61570, or CI 74260, orange pigments with the Color Index numbers CI 11725, CI 15510, CI 45370, or CI 71105, red pigments with the Color Index numbers CI 12085, CI 12120, CI 12370, CI 12420, CI 12490, CI 14700, CI 15525, CI 15580, CI 15620, CI 15630, CI 15800, CI 15850, CI 15865, CI 15880, CI 17200, CI 26100, CI 45380, CI 45410, CI 58000, CI 73360, CI 73915 and/or CI 75470, and any combination thereof.

13. The agent of claim 1 , wherein the at least one pigment is present in an amount ranging from 1.0 to 20.0 wt. %, based on the total weight of the agent.

14. The agent of claim 1 , wherein the at least one fatty component is selected from the group consisting of linear silicone oils, cyclic silicone oils, hydrocarbon oils, liquid fatty acid triglycerides, liquid fatty alcohols, ester oils, and any combination thereof.

15. The agent of claim 1 , wherein the at least one fatty component comprises at least one silicone oil of formula (V) and/or (VI):

wherein z is an integer from 0 to 10,000,

wherein y is 1, 2, 3, 4 or 5.

16. The agent according to of claim 1 , wherein the at least one fatty component is present in an amount ranging from 1.0 to 99 wt. %, based on the total weight of the agent.

17. The agent of claim 1 , further comprising at least one solvent selected from the group consisting of ethanol, isopropanol, 1,2-pro

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Jaiser Phillip
• Lechner Torsten
• Schoepgens Juergen
• Nowottny Marc
• Mathiaszyk Carsten
• Walter Andreas
• Kruppa Carolin
• Tairi Avni

Classifications

• A61Q5/10

  Preparations for permanently dyeing the hair · CPC title

• A61K2800/95

  Involves in-situ formation or cross-linking of polymers · CPC title

• A61K8/891

  saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone · CPC title

• A61K8/345

  containing more than one hydroxy group · CPC title

• A61K8/34

  Alcohols · CPC title