# US 12,109,298 B2 · Improving the fastness to washing of pigment-containing dyes by using an oxidative pretreatment agent > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,109,298 B2 - Document ID: US12109298B2 - Status: Granted - Kind: B2 - Application number: 17/913,725 - Filed: 2021-02-01 - Published: 2023-03-30 - Granted: 2024-10-08 - Earliest claimed: 2020-03-24 - Assignees: Henkel AG & Co. KGaA - Applicants: Henkel AG & Co. KGaA - Inventors: Constanze Kruck; Sandra Hilbig; Melanie Moch; Daniela Kessler-Becker - Web page: https://patentgrep.com/patent/US12109298B2 ## CPC - A61K 8/898: containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine - A61Q 5/065: {Preparations for temporary colouring the hair, e.g. direct dyes} - A61K 8/22: Peroxides; Oxygen; Ozone - A61K 8/23: Sulfur; Selenium; Tellurium; Compounds thereof - A61K 8/25: Silicon; Compounds thereof - A61Q 5/10: Preparations for permanently dyeing the hair - A61K 2800/4324: in preparations for permanently dyeing the hair - 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 A process and a kit-of-parts for dyeing keratinous material, in particular human hair, are provided. An exemplary process includes applying a pre-treatment agent (V) to the keratinous material, wherein the pre-treatment agent in a cosmetic carrier includes at least one oxidizing agent (V-1), and applying a colorant (F) to the keratinous material, the colorant being in a cosmetic carrier and including (F-1) at least one amino-functionalized silicone polymer and (F-2) at least one pigment. ## Claims ### Claim 1 A process for dyeing keratinous material comprising: applying a pre-treatment agent (V) to the keratinous material, wherein the pre-treatment agent in a cosmetic carrier comprises at least one oxidizing agent (V-1), after applying the pre-treatment agent (V) to the keratinous material, exposing the pretreatment agent to the keratinous fibers for a period of 2 to 45 minutes; rinsing out the pretreatment agent with water; after rinsing out the pretreatment, applying a colorant (F) to the keratinous material, the colorant being in a cosmetic carrier and comprising (F-1) at least one amino-functionalized silicone polymer and (F-2) at least one pigment; exposing the colorant to the keratinous fibers for a period of from 15 seconds to 45 minutes, and rinsing out the colorant with water. ### Claim 2 A process for dyeing human hair comprising: applying a pre-treatment agent (V) in a first cosmetic carrier to the human hair, wherein the pre-treatment agent comprises at least one oxidizing agent (V-1), and applying a colorant (F) in a second cosmetic carrier to the human hair, wherein the colorant comprises at least one amino-functionalized silicone polymer (F-1) and at least one pigment (F-2), wherein the at least one oxidizing agent (V-1) is selected from the group consisting of hydrogen peroxide, ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate. ### Claim 3 (depends on 1) The process according to claim 1, wherein the pretreatment agent (V) comprises (V-1) hydrogen peroxide and (V-2) at least one persulfate selected from the group consisting of ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate. ### Claim 4 (depends on 1) The process according to claim 1, wherein the pretreatment agent (V)—based on the total weight of the pretreatment agent—comprises 0.1 to 12.0 wt. % of (V-1) hydrogen peroxide. ### Claim 5 (depends on 1) The process according to claim 1, wherein the pretreatment agent (V)—based on the total weight of the pretreatment agent—comprises (V-2) one or more persulfates selected from the group consisting of ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate in a total amount of from 5.0 to 30.0 wt %. ### Claim 6 (depends on 1) The process according to claim 1, wherein the colorant (F) comprises at least one amino-functionalized silicone polymer (F-1) having at least one secondary amino group. ### Claim 7 (depends on 1) The process according to claim 1, wherein the colorant (F) comprises at least one amino-functionalized silicone polymer (F-1) comprising at least one structural unit of the formula (Si amino), where ALK1 and ALK2 independently represent a linear or branched C1-C20 divalent alkylene group. ### Claim 8 (depends on 1) The process according to claim 1, wherein the colorant (F) comprises at least one amino-functionalized silicone polymer (F-1) comprising structural units of the formula (Si-I) and of the formula (Si-II) ### Claim 9 (depends on 1) The process according to claim 1, wherein the colorant (F) comprises—based on the total weight of the colorant—one or more amino-functionalized silicone polymers (F-1) in a total amount of from 0.1 to 8.0 wt. %. ### Claim 10 (depends on 1) The process according to claim 1, wherein the colorant (F) comprises at least inorganic pigment (F-2) selected from the group consisting of colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates, bronze pigments, and/or from mica- or mica-based colored pigments coated with at least one metal oxide and/or a metal oxychloride. ### Claim 11 (depends on 1) The process according to claim 1, wherein the colorant (F) comprises at least one organic pigment (F-2) selected from the group consisting of carmine, quinacridone, phthalocyanine, Sorgho, blue pigments with the Color Index numbers Cl 42090, CI 69800, CI 69825, CI 73000, CI 74100, 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, CI 47005, green pigments with Color Index numbers CI 61565, CI 61570, CI 74260, orange pigments with Color Index numbers CI 11725, CI 15510, CI 45370, CI 71105, red pigments with 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. ### Claim 12 (depends on 1) The process according to claim 1, wherein the colorant (F) comprises—based on the total weight of the colorant—one or more pigments (F-2) in a total amount of from 0.01 to 10.0 wt. %. ### Claim 13 (depends on 1) The process according to claim 1, wherein the colorant (F) comprises direct dyes, and wherein the total amount of direct dyes contained in the colorant (F) based on the total weight of the colorant (F)—is below 0.1 wt. %. ### Claim 14 (depends on 1) The process according to claim 1, further comprising waiting for a period of at most 24 hours after rinsing out the pretreatment agent with water before applying the colorant (F) to the keratinous material. ### Claim 15 (depends on 1) The process of claim 1, wherein the keratinous material is oxidative pretreated human hair. ### Claim 16 A process for dyeing keratinous material comprising: applying a pre-treatment agent (V) to the keratinous material, wherein the pre-treatment agent in a cosmetic carrier comprises at least one oxidizing agent (V-1), and wherein the pretreatment agent (V)—based on the total weight of the pretreatment agent—comprises 3.0 to 6.0 wt. % of (V-1) hydrogen peroxide; rinsing out the pretreatment agent (V) with water and applying a colorant (F) to the keratinous material, the colorant being in a cosmetic carrier and comprising (F-1) at least one amino-functionalized silicone polymer and (F-2) at least one pigment. ### Claim 17 (depends on 16) The process according to claim 16, wherein the pretreatment agent (V)—based on the total weight of the pretreatment agent—comprises (V-2) one or more persulfates selected from the group consisting of ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate in a total amount of from 14.0 to 21.0 wt %. ### Claim 18 (depends on 17) The process according to claim 17, wherein: the keratinous material is oxidative pretreated human hair; the colorant (F) comprises—based on the total weight of the colorant—one or more pigments (F-2) in a total amount of from 0.25 to 1.5 wt. %; the colorant (F) comprises direct dyes; the total amount of direct dyes contained in the colorant (F)—based on the total weight of the colorant (F)—is below 0.001 wt. %; the colorant (F) comprises—based on the total weight of the colorant—one or more amino-functionalized silicone polymers (F-1) in a total amount of from 0.4 to 2.5 wt. %; and the colorant (F) comprises at least inorganic pigment (F-2) selected from the group consisting of colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates, bronze pigments, and/or from mica- or mica-based colored pigments coated with at least one metal oxide and/or a metal oxychloride. ### Claim 19 (depends on 1) The process according to claim 1, further comprising waiting for a period of at most 3 hours after rinsing out the pretreatment agent with water before applying the colorant (F) to the keratinous material. ### Claim 20 (depends on 2) The process according to claim 2 wherein: the pretreatment agent (V), based on the total weight of the pretreatment agent, comprises 0.1 to 12.0 wt. % of (V-1) hydrogen peroxide; and the pretreatment agent (V), based on the total weight of the pretreatment agent, comprises 5.0 to 30.0 wt % of (V-2) at least one persulfate selected from the group consisting of ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate.