Gentle hair color pretreatment with silicone and oily oxidants

• US 8,790,417 B2
• Filed: 12/18/2013
• Issued: 07/29/2014
• Est. Priority Date: 12/19/2012
• Status: Active Grant

• Current Assignee: Henkel AG & Co KGaA
• Original Assignee: Henkel AG & Co KGaA
• Inventors: Schweinsberg, Matthias, Baek, Jisook, Kleen, Astrid, Schulze zur Wiesche, Erik
• Primary Examiner(s): ELHILO, EISA B
• Application Number:
  US14/132,155
• Publication Number:
  US 20140165303A1
• Time in Patent Office: 223 Days
• Field of Search: 840/5, 840/6, 858/1, 424/70.1
• US Class Current: 8/405
• CPC Class Codes: A61K 2800/884 Sequential application
• CPC Class Codes: A61K 8/25 Silicon; Compounds thereof
• CPC Class Codes: A61K 8/31 Hydrocarbons
• CPC Class Codes: A61K 8/585 Organosilicon compounds
• CPC Class Codes: A61K 8/898 containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• CPC Class Codes: A61K 8/92 Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
• CPC Class Codes: A61Q 5/10 Preparations for permanently dyeing the hair

Abstract

Methods and compounds are provided for oxidative coloring of keratinic fibers, in particular hair. The method includes applying a pretreatment agent onto the hair, where the pretreatment agent includes at least one 4-morpholinomethyl-substituted silicone. A hair coloring agent is applied to the hair subsequent to the pretreatment agent within a time span from about 1 second to about 24 hours. The hair coloring agent is obtained by mixing a composition (A), which contains at least one oxidation dye precursor of the developer type and at least one oxidation dye precursor of the coupler type, with a composition (B) that contains at least one oxidizing agent. Composition (B) contains at least one cosmetic oil in a total quantity from 10 to 80 wt %, based on the weight of composition (B).

Claims

1. A method for oxidative coloring of keratinic fibers, in particular of hair, the method comprising the steps of:

applying a pretreatment agent onto the keratinic fibers, in particular onto the hair, wherein the pretreatment agent contains;

at least one 4-morpholinomethyl-substituted silicone of formula (V),

2. The method according to claim 1, wherein applying the pretreatment agent further comprises applying the pretreatment agent wherein the pretreatment agent contains the at least one 4-morpholinomethyl-substituted silicone of formula (V) in which

m>

(n+o) resp. (a+b+c)>

(n+o), preferably

m>

8(n+o) resp. (a+b+c)>

8(n+o), particularly preferably

m>

25(n+o) resp. (a+b+c)>

25(n+o), more preferably

m>

77(n+o) resp. (a+b+c)>

77(n+o), and in particular

m>

200(n+o) resp. (a+b+c)>

200(n+o).

3. The method according to claim 1, wherein applying the pretreatment agent further comprises applying the pretreatment agent wherein the pretreatment agent contains, based on its weight, the at least one 4-morpholinomethyl-substituted silicone in a total quantity from about 0.001 to about 5 wt %, based on the total weight of the pretreatment agent.

4. The method according to claim 1, wherein applying the pretreatment agent further comprises applying the pretreatment agent, wherein the pretreatment agent contains, based on its weight, the at least one 4-morpholinomethyl-substituted silicone of formula (V) that respectively comprises at least one of the structural units of formulas (I), (II), and (III), in a total quantity from about 0.001 to about 5 wt %, based on the total weight of the pretreatment agent.

5. The method according to claim 1, wherein applying the pretreatment agent further comprises applying the pretreatment agent wherein the pretreatment agent contains a hydroxy-terminated 4-morpholinomethyl-substituted silicone in which the molar ratio of hydroxy to alkoxy is in the range from about 0.2:

1 to about 0.4;

1.

6. The method according to claim 1, wherein applying the pretreatment agent further comprises applying the pretreatment agent wherein the weight-average molar mass of the at least one 4-morpholinomethyl-substituted silicone of formula (V) is in the range from about 2,000 to about 1,000,000 grams per mole.

7. The method according to claim 1, wherein applying the pretreatment agent further comprises applying the pretreatment agent wherein the at least one 4-morpholinomethyl-substituted silicone of formula (V) is present in the form of an oil-in-water emulsion in which the number-average size of the silicone particles in the emulsion is in the range from about 3 to about 500 nanometers.

8. The method according to claim 1, wherein applying a hair coloring agent onto the keratinic fibers further comprises applying a hair coloring agent onto the keratinic fibers wherein the at least one cosmetic oil that is contained in composition (B) in a total quantity from about 10 to about 80 wt %, based on the weight of composition (B), is selected from:

paraffin oils, including C₁₈ to C₃₀ isoparaffins;

benzoic acid esters of linear or branched C_8-22 alkanols;

fatty alcohols having 6 to 30 carbon atoms, which are unsaturated or branched and saturated or branched and unsaturated;

triglycerides of linear or branched, saturated or unsaturated, optionally hydroxylated C_8-30 fatty acids, in particular natural oils;

dicarboxylic acid esters of linear or branched C₂ to C₁₀ alkanols;

esters of linear or branched, saturated or unsaturated fatty alcohols having 2 to 30 carbon atoms with linear or branched, saturated or unsaturated fatty acids having 2 to 30 carbon atoms, which can be hydroxylated;

addition products of 1 to 5 propylene oxide units with mono- or polyvalent C_8-22 alkanols;

addition products of at least 6 ethylene oxide and/or propylene oxide units with mono- or polyvalent C_3-22 alkanols;

C₈ to C₂₂ fatty alcohol esters of monovalent or polyvalent C₂ to C₇ hydroxycarboxylic acids;

symmetrical, asymmetrical, or cyclic esters of carbonic acid with C_3-22 alkanols, C_3-22 alkanediols, or C_3-22 alkanetriols;

esters of dimers of unsaturated C₁₂ to C₂₂ fatty acids (dimer fatty acids) with monovalent linear, branched, or cyclic C₂ to C₁₈ alkanols or with polyvalent linear or branched C₂ to C₆ alkanols;

silicone oils; and

mixtures of the aforementioned substances.

9. The method according to claim 1, wherein applying a hair coloring agent onto the keratinic fibers further comprises applying a hair coloring agent onto the keratinic fibers wherein composition (B) contains the at least one cosmetic oil in a total quantity from about 12 to about 70 wt %, based on the weight of composition (B).

10. The method according to claim 1, wherein applying a hair coloring agent onto the keratinic fibers further comprises applying a hair coloring agent onto the keratinic fibers wherein composition (B) contains:

about 1 to about 24 wt % hydrogen peroxide (calculated as 100% H₂O₂);

furthermore

at least one cosmetic oil in a total quantity from about 12 to about 70 wt %;

furthermore

at least one surfactant in a total quantity from about 0.1 to about 5 wt %;

as well as

at least one linear saturated alkanol having 12 to 30 carbon atoms, in a total quantity from about 0.1 to about 10 wt %;

where all “

wt %”

indications refer to the weight of composition (B).

11. The method according to claim 1, wherein applying a hair coloring agent onto the keratinic fibers further comprises applying a hair coloring agent onto the keratinic fibers wherein the hair coloring agent contains the at least one cosmetic oil in a total quantity from about 5 to about 50 wt %, based on the total weight of the hair coloring agent.

12. The method according to claim 1 further comprising:

rinsing out the hair, drying the hair, or combinations of rinsing and drying the hair, wherein drying the hair further comprises drying the hair with a towel, allowing the hair to air-dry, blow drying the hair, drying the hair with a drying hood, or combinations thereof, wherein drying the hair further comprises drying the hair at a temperature of from about 20°

C. to about 150°

C., and wherein rinsing out the hair and/or drying the hair is performed from about 2 seconds to about 120 minutes after applying the pretreatment agent onto the hair.

13. The method according to claim 1 further comprising:

drying the hair, wherein drying the hair further comprises drying the hair with a towel, allowing the hair to air-dry, blow drying the hair, drying the hair with a drying hood, or combinations thereof, wherein drying the hair further comprises drying the hair at a temperature of from about 20°

C. to about 150°

C., wherein drying the hair is performed from about 2 seconds to about 120 minutes after applying the pretreatment agent onto the hair, and wherein drying the hair further comprises drying the hair without rinsing out the hair such that no rinsing out of the hair occurs between applying the pretreatment agent and the drying of the hair.

14. The method according to claim 1, wherein applying a hair coloring agent onto the keratinic fibers further comprises applying a hair coloring agent onto the keratinic fibers from about 30 seconds to about 20 minutes after applying the pretreatment agent onto the hair.

15. The method according claim 1, wherein applying a hair coloring agent onto the keratinic fibers further comprises applying a hair coloring agent onto the keratinic fibers wherein the combination of the at least one oxidation dye precursor of the developer type and the at least one oxidation dye precursor of the coupler type applied is selected from at least one of the following combinations, where the amine compounds and the nitrogen heterocycles can also be present in the form of their physiologically acceptable salts:

p-toluoylenediamine/resorcinol;

p-toluoylenediamine/2-methylresorcinol;

p-toluoylenediamine/5-amino-2-methylphenol;

p-toluoylenediamine/3-aminophenol;

p-toluoylenediamine/2-(2,4-diaminophenoxy)ethanol;

p-toluoylenediamine/1,3-bis(2,4-diaminophenoxy)propane;

p-toluoylenediamine/1-methoxy-2-amino-4-(2-hydroxyethylamino)benzene;

p-toluoylenediamine/2-amino-3-hydroxypyridine;

p-toluoylenediamine/1-naphthol;

2-(2-hydroxyethyl)-p-phenylenediamine/resorcinol;

2-(2-hydroxyethyl)-p-phenylenediamine/2-methylresorcinol;

2-(2-hydroxyethyl)-p-phenylenediamine/5-amino-2-methylphenol;

2-(2-hydroxyethyl)-p-phenylenediamine/3-aminophenol;

2-(2-hydroxyethyl)-p-phenylenediamine/2-(2,4-diaminophenoxy)ethanol;

2-(2-hydroxyethyl)-p-phenylenediamine/1,3-bis(2,4-diaminophenoxy)propane;

2-(2-hydroxyethyl)-p-phenylenediamine/1-methoxy-2-amino-4-(2-hydroxyethylamino)benzene;

2-(2-hydroxyethyl)-p-phenylenediamine/2-amino-3-hydroxypyridine;

2-(2-hydroxyethyl)-p-phenylenediamine/1-naphthol;

2-methoxymethyl-p-phenylenediamine/resorcinol;

2-methoxymethyl-p-phenylenediamine/2-methylresorcinol;

2-methoxymethyl-p-phenylenediamine/5-amino-2-methylphenol;

2-methoxymethyl-p-phenylenediamine/3-aminophenol;

2-methoxymethyl-p-phenylenediamine/2-(2,4-diaminophenoxy)ethanol;

2-methoxymethyl-p-phenylenediamine/1,3-bis(2,4-diaminophenoxy)propane;

2-methoxymethyl-p-phenylenediamine/1-methoxy-2-amino-4-(2-hydroxyethylamino)benzene;

2-methoxymethyl-p-phenylenediamine/2-amino-3-hydroxypyridine;

2-methoxymethyl-p-phenylenediamine/1-naphthol;

N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine/resorcinol;

N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine 2-methylresorcinol;

N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine/5-amino-2-methylphenol;

N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine 3-aminophenol;

N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine/2-(2,4-diaminophenoxy)ethanol;

N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine/1,3-bis(2,4-diaminophenoxy)propane;

N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine/1-methoxy-2-amino-4-(2-hydroxyethylamino)benzene;

N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine/2-amino-3-hydroxypyridine;

N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine/1-naphthol;

4,5-diamino-1-(2-hydroxyethyl)pyrazole/resorcinol;

4,5-diamino-1-(2-hydroxyethyl)pyrazole/2-methylresorcinol;

4,5-diamino-1-(2-hydroxyethyl)pyrazole/5-amino-2-methylphenol;

4,5-diamino-1-(2-hydroxyethyl)pyrazole/3-aminophenol;

4,5-diamino-1-(2-hydroxyethyl)pyrazole/2-(2,4-diaminophenoxy)ethanol;

4,5-diamino-1-(2-hydroxyethyl)pyrazole/1,3-bis(2,4-diaminophenoxy)propane;

4,5-diamino-1-(2-hydroxyethyl)pyrazole 1-methoxy-2-amino-4-(2-hydroxyethylamino)benzene;

4,5-diamino-1-(2-hydroxyethyl)pyrazole/2-amino-3-hydroxypyridine;

4,5-diamino-1-(2-hydroxyethyl)pyrazole/1-naphthol.