Method for dyeing keratinous material, comprising the use of an organosilicon compound, an hydroxycarboxylic acid ester, a diol and a dyeing compound

Patent metadata

Field	Value
Publication number	US-11883518-B2
Application number	US-202017785878-A
Country	US
Kind code	B2
Filing date	Oct 16, 2020
Priority date	Dec 16, 2019
Publication date	Jan 30, 2024
Grant date	Jan 30, 2024

Abstract

The subject of the present disclosure is a method 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 hydroxycarboxylic acid ester, (a3) at least one diol and Application of an agent (b) to the keratinous material, wherein the agent (b) comprises:
(b1) at least one sealing reagent,
wherein at least one of the agents (a) and (b) further comprises at least one colorant compound selected from the group of pigments and/or direct dyes.

First claim

The invention claimed is:

1. A method for dyeing keratinous material, the method comprising the steps of:
applying an agent (a) to the keratinous material, wherein the agent (a) comprises:
(a1) an organic silicon compound selected from the group of silanes having one, two or three silicon atoms,
(a2) a hydroxycarboxylic acid ester, and
(a3) a diol and

applying an agent (b) to the keratinous material, wherein the agent (b) comprises:
(b1) a sealing reagent,

wherein at least one of the agents (a) and (b) further comprises at least one colorant compound selected from the group of pigments and/or direct dyes.

2. The method according to claim 1 , wherein the agent (a) comprises the organic silicon compound (a1) of a formula (I) and/or a formula (II)
R 1 R 2 N-L-Si(OR 3 ) a (R 4 ) b   (I),

where
R 1 , R 2 independently represent 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 , R 4 are independent of each other and represent a C 1 -C 6 alkyl group,
a represents an integer from 1 to 3, and
b is the integer 3-a, and
wherein in the organic silicon compound of formula (II)
(R 5 O) c (R 6 ) d S i -(A )e -[NR 7 -(A′)] f -[O-(A″)] g -[NR 8 -(A′″)] h -Si(R 6 ′) d ′(OR 5 ′) c ′  (II),

wherein
R5, R5′, R5″, R6, R6′ and R6″ independently represent a C 1 -C 6 alkyl group,
A, A′, A″, A′″ and A″″ independently represent a linear or branched C 1 -C 20 divalent alkylene group,
R 7 and R 8 independently represent 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 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,

with the proviso that at least one of the radicals from e, f, g and h is different from 0.

3. The method according to claim 2 , wherein the agent (a) comprises the organic silicon compound (a1) of the formula (I),
R 1 R 2 N-L-Si(OR 3 ) a (R 4 ) b   (I),

where
R 1 , and R 2 both represent a hydrogen atom,
L is a linear, divalent C 1 -C 6 alkylene group,
R 3 , and R 4 independently represent a methyl group or an ethyl group,
a stands for number 3 and
b stands for number 0.

4. The method according to claim 2 , wherein the agent (a) comprises the organic silicon compound (a1) of the formula (I) selected from the group 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
combinations thereof.

5. The method according to claim 2 , wherein the agent (a) comprises the organic silicon compound (a1) of the formula (II),
(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),

where
e and f both stand for number 1,
g and h both stand for number 0,
A and A′ independently of one another 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).

6. The method according to claim 1 , wherein the agent (a) comprises the organic silicon compound (a1) of a formula (IV),
R 9 Si(OR 10 ) k (R 11 ) m   (IV),

where
R 9 stands for a C 1 -C 18 alkyl group,
R 10 represents a hydrogen atom or a C 1 -C 6 alkyl group,
R 11 stands for a C 1 -C 6 alkyl group
k is an integer from 1 to 3, and
m stands for the integer 3-k.

7. The method according to claim 6 , wherein the agent (a) comprises the organic silicon compound (a1) of the formula (IV) selected from the group of:
Methyltrimethoxysilane
Methyltriethoxysilane
Ethyltrimethoxysilane
Ethyltriethoxysilane
Propyltrimethoxysilane
Propyltriethoxysilane
Hexyltrimethoxysilane
Hexyltriethoxysilane
Octyltrimethoxysilane
Octyltriethoxysilane
Dodecyltrimethoxysilane,
Dodecyltriethoxysilane,
Octadecyltrimethoxysilane,
Octadecyltriethoxysilane and
Mixtures thereof.

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

9. The method of claim 8 , wherein the sealing reagent comprises a compound selected from the group of film-forming polymers, alkalizing agents, acidifying agents, and mixtures thereof.

10. The method according to claim 1 , wherein the agent (a) comprises citric acid triethyl ester as the hydroxycarboxylic acid ester (a2).

11. The method according to claim 1 , wherein the agent (a) comprises the diol (a3) selected from the group of ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, and combinations thereof.

12. The method according to claim 1 , wherein the agent (a) and the agent (b) each further comprise at least one colorant compound selected from the group of pigments and/or direct dyes.

13. The method according to claim 1 , wherein the agent (b) further comprises a colorant compound selected from the group of pigments and/or direct dyes comprising at least one pigment selected from the group of lamellar metallic substrate platelet-based pigments, lenticular metallic substrate platelet-based pigments, vacuum metallized pigment (VMP), lenticular metallic substrate platelet, pigments based on a metallic substrate platelet comprising “vacuum metallized pigment” (VMP), pigments based on natural or synthetic mica coated with at least one metal oxide, pigments based on natural or synthetic mica coated with a metal oxychloride, and combinations thereof.

14. The method according to claim 1 , wherein the agent (a) further comprises a coloring compound selected from the group of pigments and/or direct dyes comprising at least one pigment selected from the group of carmine, quinacridone, phthalocyanine, sorghum, blue pigments having the color index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments having the color index numbers CI 11680, CI 11710, CI 15985, CI 19140, CI 20040, CI 21100, CI 21108, CI 47000, CI 47005, green pigments with the Color Index numbers CI 61565, CI 61570, CI 74260, orange pigments with the Color Index numbers CI 11725, CI 15510, CI 45370, 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, CI 75470, colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates, bronze pigments and mixtures thereof;
and wherein the composition (b) further comprises a coloring compound selected from the group of pigments and/or direct-acting dyes which comprises at least one pigment selected from the group of pigments based on a lamellar metallic substrate platelet, pigments based on a lenticular metallic substrate platelet, pigments based on a metallic substrate platelet comprising “vacuum metallized pigment” (VMP), pigments based on mica coated with a metal o

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Krohn Rene
• Hippe Thomas
• Brender Jessica
• Hoepfner Stefan

Classifications

• A61K8/585 Primary

  Organosilicon compounds · CPC title

• A61K8/345

  containing more than one hydroxy group · CPC title

• A61K8/37

  Esters of carboxylic acids · CPC title

• A61Q5/10

  Preparations for permanently dyeing the hair · CPC title

• A61K2800/432

  Direct dyes · CPC title