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EP4496556A1 - Agent de coloration oxydative de fibres de kératine, contenant au moins un précurseur de colorant d'oxydation du type révélateur, au moins un précurseur de colorant d'oxydation du type coupleur et de l'isatine - Google Patents

Agent de coloration oxydative de fibres de kératine, contenant au moins un précurseur de colorant d'oxydation du type révélateur, au moins un précurseur de colorant d'oxydation du type coupleur et de l'isatine

Info

Publication number
EP4496556A1
EP4496556A1 EP23700397.5A EP23700397A EP4496556A1 EP 4496556 A1 EP4496556 A1 EP 4496556A1 EP 23700397 A EP23700397 A EP 23700397A EP 4496556 A1 EP4496556 A1 EP 4496556A1
Authority
EP
European Patent Office
Prior art keywords
weight
agent
amino
oxidation dye
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP23700397.5A
Other languages
German (de)
English (en)
Inventor
Thomas Hippe
Astrid Kleen
Hartmut Manneck
Stefan Hoepfner
Tugce Cansev
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP4496556A1 publication Critical patent/EP4496556A1/fr
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A61K2800/4324—Direct dyes in preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits

Definitions

  • Agent for the oxidative coloring of keratin fibers containing at least one developer-type oxidation dye precursor, at least one coupler-type oxidation dye precursor and isatin
  • the subject of the present invention is a cosmetic agent for the oxidative coloring of keratin fibers, which contains at least one oxidation dye precursor of the developer type (a), at least one oxidation dye precursor of the coupler type (b) and isatin (c).
  • Another item is a multi-component packaging unit (kit-of-parts), which separately assembled comprises two agents in two containers, the agent in the first container containing the ingredients (a), (b) and (c) and the agent in second container contains at least one oxidizing agent from the group consisting of hydrogen peroxide and its addition products to organic or inorganic compounds.
  • kit-of-parts which separately assembled comprises two agents in two containers, the agent in the first container containing the ingredients (a), (b) and (c) and the agent in second container contains at least one oxidizing agent from the group consisting of hydrogen peroxide and its addition products to organic or inorganic compounds.
  • Another subject is a process for the oxidative dyeing of keratin fibers, in which an agent containing (a), (b) and (c) is applied to the keratin fibers and rinsed out again after an exposure time.
  • oxidation dyes are used for permanent, intensive dyeing with appropriate fastness properties.
  • Such colorants usually contain oxidation dye precursors, so-called developer components and coupler components, which form the actual dyes among themselves under the influence of oxidizing agents such as hydrogen peroxide.
  • the oxidation dyes are characterized by excellent, long-lasting dyeing results.
  • oxidation dye precursors themselves are not colored, but the actual dyes are only formed during the course of application through contact of the oxidation dye precursors with the oxidizing agent (hydrogen peroxide).
  • the developers used as oxidation dye precursors (such as p-phenylenediamine or its derivatives) are first oxidatively converted by hydrogen peroxide into a reactive intermediate, also called quinoneimine or quinonediimine, which then reacts in an oxidative coupling reaction with the couplers to form the respective dye.
  • quinoneimine reactive intermediate
  • quinonediimine reactive intermediate
  • hair can be colored in both intense fashion shades and natural shades by choosing the appropriate developer components and coupler components.
  • oxidative dyes A large area of application for oxidative dyes is the coloring of graying hair in a natural shade that is similar to the hair color that the user had when he was younger.
  • the expert knows the use of developers based on the base of 1,4-diaminobenzene (para-phenylenediamine) and couplers with a resorcinol structure (1,3-dihydroxybenzene). .
  • oxidation dyes have been used for decades. Although they are only intended for extracorporeal use on keratin fibers such as scalp hair, eyelashes and eyebrows, contact of the dye with the scalp cannot be completely avoided during application.
  • SCCP Scientific Committee on Consumer Products
  • some of the oxidation dye precursors in particular some of the oxidation bases of the para-phenylenediamine type, may have a certain sensitization potential. Therefore, before using the dye on the hair, customers are recommended to conduct a preliminary test with a small amount of the dye on the skin to rule out allergic reactions during or after the dyeing process. In addition to skin sensitization, other physiological effects are also monitored.
  • Resorcinol, 4-chloro-resorcinol and 2-methyl-resorcinol are common oxidation dye precursors with a 1,3-dihydroxybenzene base.
  • the SCCP concluded that the use of resorcinol in oxidative hair dyes is considered safe at a resorcinol concentration of up to 1.25% by weight in the ready-to-use mixture.
  • the aim of the present invention was to provide an agent for oxidative dyeing of keratin fibers, particularly human hair, capable of covering a wide range of colors, particularly a natural range of colors with cool natural tones and warm natural tones as well as a gold color series that leads to colorings with high fastness properties, without the affecting product safety.
  • coloring in these natural shades should be possible without the use of recorcine-type couplers.
  • an oxidative colorant which contains at least one oxidation dye precursor of the developer type (a) and at least one oxidation dye precursor of the coupler type (b) and isatin (c).
  • a first subject of the present invention is an agent for the oxidative dyeing of keratin fibers, in particular human hair, contained in a cosmetic carrier
  • keratin fibers mean all animal hair, e.g. wool, horsehair, angora hair, fur, feathers and products or textiles made from them. However, the keratin fibers are preferably human hair.
  • agents for oxidative dyeing of the keratin fibers used according to the invention refers to oxidative dyes.
  • Oxidative colorants contain oxidation dyes Preliminary products, so-called developers and coupler components. Developer and coupler diffuse separately into the keratin fiber and form the actual dyes in a chemical reaction under the influence of an alkalizing agent (e.g. ammonia) and an oxidizing agent (hydrogen peroxide).
  • an alkalizing agent e.g. ammonia
  • an oxidizing agent hydrogen peroxide
  • the keratin fiber is lightened to a greater or lesser extent during coloring, as the oxidizing agent not only initiates the dye formation process of developers and couplers, but also oxidatively destroys the hair's own pigments (melanins).
  • the oxidative coloring can therefore be primarily a coloring (with a high proportion of dye) or primarily a lightening (with a high proportion of oxidizing agent).
  • the oxidation dye precursors are mainly used to nuance the lightening result.
  • the agents according to the invention contain the components essential to the invention in a cosmetic carrier, preferably in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a cosmetic carrier preferably in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier for the purpose of hair coloring, such carriers are, for example, creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, foam aerosols, foam formulations or other preparations that are suitable for use on the hair.
  • the oxidative dye described above is a ready-to-use dye that is applied in this form containing the components (a) and (b) and (c) for use on the keratin fibers.
  • Oxidative dyes contain oxidation dye precursors, so-called developers and coupler components, to form the color. Developer and coupler diffuse separately into the keratin fiber and, under the influence of ammonia as an alkalizing agent and an oxidizing agent (usually hydrogen peroxide), form the actual dyes in a chemical reaction with one another. Depending on the amount of oxidizing agent used, the keratin fiber is lightened to a greater or lesser extent during coloring, as the oxidizing agent not only initiates the dye formation process of developers and couplers, but also oxidatively destroys the hair's own pigments (melanins).
  • the oxidative coloring can therefore be primarily a coloring (with a high proportion of dye) or primarily a lightening (with a high proportion of oxidizing agent).
  • the oxidation dye precursors are mainly used to nuance the lightening result.
  • the oxidative dyes according to the invention contain at least one oxidation dye precursor of the developer type, also referred to as developer for short.
  • developer-type oxidation dye precursors are selected from the group consisting of p-toluenediamine, 2-methoxymethyl-p-phenylenediamine, 2-(2-hydroxyethyl)-p-phenylenediamine, N,N-bis-(2-hydroxyethyl)- p-phenylenediamine, p-phenylenediamine and their physiologically tolerated salts.
  • an agent according to the invention is therefore characterized in that it contains at least one oxidation dye precursor of developer type (a), which is selected from the group consisting of p-toluenediamine, 2-methoxymethyl-p-phenylenediamine, 2-(2-hydroxyethyl )-p-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, p-phenylenediamine and their physiologically tolerated salts.
  • developer type (a) is selected from the group consisting of p-toluenediamine, 2-methoxymethyl-p-phenylenediamine, 2-(2-hydroxyethyl )-p-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, p-phenylenediamine and their physiologically tolerated salts.
  • p-Toluenediamine is also alternatively referred to as 2,5-toluenediamine, p-toluenediamine (abbreviation: PTD), 2,5-diaminotoluene, 2-methyl-p-phenylenediamine or 2,5-diaminomethylbenzene.
  • PTD has the CAS number 95-70-5.
  • 2-Methoxymethyl-p-phenylenediamine is alternatively known as 2-methoxymethyl-1,4-benzene-diamine and has the CAS number 337906-36-2 in the form of its free base.
  • 2-(2-Hydroxyethyl)-p-phenylenediamine is alternatively referred to as 2-(2,5-diaminophenyl)ethanol and has the CAS number 93841-24-8 in the form of its free base.
  • N,N-Bis-(2-hydroxyethyl)-p-phenylenediamine has the CAS number 7575-35-1 in the form of its free base.
  • an oxidative coloring agent which contains a developer (a) of the aforementioned group with the basic structure of 1,4-diaminobenzene
  • hair could be colored with very high intensity in natural shades, in particular in dark brown, medium brown and dark blonde shades.
  • hair could be dyed in a shade that was particularly similar to the shade obtained with a dye containing the classic combination of PDT and resorcinol.
  • Agents which contain at least one oxidation dye precursor of developer type (a), which is selected from the group consisting of p-toluenediamine, 2-methoxymethyl-p-phenylenediamine and their physiologically tolerated salts, have proven to be particularly suitable for solving the problem according to the invention .
  • an agent according to the invention is therefore characterized in that it contains at least one oxidation dye precursor of developer type (a), which is selected from the group consisting of p-toluenediamine, 2-methoxymethyl-p-phenylenediamine and their physiologically tolerated salts.
  • developer type (a) which is selected from the group consisting of p-toluenediamine, 2-methoxymethyl-p-phenylenediamine and their physiologically tolerated salts.
  • the agent according to the invention can also contain other developers (a). Developers from the group consisting of 4-amino-3-methylphenol, p-aminophenol, 4,5-diamino-1-(2-hydroxyethyl)pyrazole and their physiologically tolerated salts are particularly suitable for this. These developers can be used either as a sole component of the group or together with one or more developers with a basic structure of p-phenylenediamine.
  • an agent according to the invention is therefore characterized in that it contains at least one oxidation dye precursor of developer type (a), which is selected from the group consisting of 4-amino-3-methylphenol, p-aminophenol, 4,5-diaminophenol. 1-(2-hydroxyethyl)pyrazole and their physiologically tolerated salts.
  • developer type (a) which is selected from the group consisting of 4-amino-3-methylphenol, p-aminophenol, 4,5-diaminophenol. 1-(2-hydroxyethyl)pyrazole and their physiologically tolerated salts.
  • the developers of the above-mentioned groups can be used in the form of their free base or in the form of their physiologically tolerated salts in the agent according to the invention.
  • a physiologically tolerable salt is understood to mean a salt of the developer that is well tolerated by the user under physiological conditions, i.e. during use of the agent.
  • Physiologically compatible salts are in particular the chlorides, bromides, sulfates and hemisulfates of the developers (a).
  • an agent according to the invention is therefore characterized in that it contains at least one oxidation dye precursor of developer type (a), which is selected from the group consisting of p-toluenediamine, p-toluenediamine sulfate, p-toluenediamine chloride, p -Toluenediamine bromide, 2-methoxymethyl-p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine sulfate, 2-methoxymethyl-p-phenylenediamine chloride and 2-methoxymethyl-p-phenylenediamine bromide, , 4,5-diamino-1- (2-hydroxyethyl)pyrazole chloride, 4,5-diamino-1-(2-hydroxyethyl)pyrazole bromide and , 4,5-diamino-1-(2-hydroxyethyl)pyrazole sulfate.
  • developer type (a) is selected from the group consisting of
  • the developer or developers are preferably used in certain quantity ranges in the agent according to the invention.
  • the agent preferably contains - based on the total weight of the agent - one or more oxidation dye precursors of developer type (a) in a total amount of 0.001 to 10.0% by weight, preferably 0.01 to 6.0% by weight preferably from 0.1 to 5.0% by weight and very particularly preferably from 0.15 to 4.7% by weight.
  • an agent according to the invention is therefore characterized in that - based on the total weight of the agent - it contains one or more oxidation dye precursors of developer type (a) in a total amount of 0.001 to 10.0% by weight, preferably 0. 01 to 6.0% by weight, more preferably from 0.1 to 5.0% by weight and most preferably from 0.15 to 4.7% by weight.
  • the agent additionally contains one or more further oxidation dye precursors of the developer type, which are selected from the group bis-(2-hydroxy-5-aminophenyl)methane, 1,3-bis-(2 ,5-diaminophenoxy)propan-2-ol,
  • N,N'-Bis-(4-aminophenyl)-1,4-diazacycloheptane 1,10-bis-(2,5-diaminophenyl)-1,4,7,10-tetraoxadecane,
  • 4-Amino-2-aminomethylphenol 4-amino-2-(1,2-dihydroxyethyl)phenol, 4-amino-2-(diethylaminomethyl)phenol, 2,4,5,6-tetraaminopyrimidine, 4-hydroxy- 2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-tri-aminopyrimidine, 2,3-diamino-6,7-dihydro-1 H,5H-pyrazolo[1,2-a]pyrazole-1 -on and their physiologically tolerated salts.
  • the additional developer or developers can - based on the total weight of the agent - in a total amount of 0.001 to 10.0% by weight, preferably from 0.01 to 6.0% by weight, more preferably of
  • the agent may contain 0.1 to 5.0% by weight and very particularly preferably from 0.15 to 4.7% by weight.
  • the base color of the natural shade can be created by combining the developer (a) with Isatin (c).
  • the oxidation dye contains at least one oxidation dye precursor of the coupler type (b) in addition to the oxidation dye precursors (a) and isatin (c).
  • Very suitable couplers can be selected, for example, from the group of 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol,
  • an agent according to the invention is therefore characterized in that it contains at least one oxidation dye precursor of coupler type (b), which is selected from the group consisting of 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2- chloro-6-methyl-phenol, 2-hydroxy-4-aminophenoxyethanol, 5-amino-4-chloro-2-methylphenol, 5-(2-hydroxyethyl)-amino-2-methylphenol, 2,4-dichloro-3- aminophenol, 2-aminophenol, 3-phenylenediamine, 2-(2,4-diaminophenoxy)ethanol, 1,3-bis(2,4-diaminophenoxy)propane, 1-methoxy-2-amino-4-(2- hydroxyethylamino)-benzene, 1,3-bis(2,4-diaminophenyl)propane, 2,6-bis(2'-hydroxyethylamino)-1-methylbenzene, 1-amino-3-
  • the colorant additionally contained one or more couplers (b) which were selected from the group consisting of 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-amino-3-hydroxypyridine, 1-methoxy-2-amino-4-(2-hydroxyethyl-amino)benzene, 6-hydroxyindole or or mixtures of these compounds or their physiological compatible salts.
  • couplers (b) from this group is explicitly particularly preferred.
  • an agent according to the invention is therefore characterized in that it contains at least one oxidation dye precursor of the coupler type (b), which is selected from the group consisting of 3-aminophenol, 5-amino-2-methylphenol, 3-amino- 2-chloro-6-methylphenol, 2-amino-3-hydroxypyridine, 1-methoxy-2-amino-4-(2-hydroxyethylamino)benzene, 6-hydroxyindole and their physiologically tolerated salts.
  • the couplers from group (b) described above are preferably used in certain quantitative ranges in the agent according to the invention.
  • the agent - based on the total weight of the agent - contained one or more oxidation dye precursors of the coupler type (b) in a total amount of 0.001 to 10% by weight, preferably 0.01 to 5% by weight. %, more preferably from 0.1 to 3.5% by weight and very particularly preferably from 0.15 to 2.5% by weight.
  • an agent according to the invention is therefore characterized in that - based on the total weight of the agent - it contains one or more oxidation dye precursors of the coupler type (b) in a total amount of 0.001 to 10% by weight, preferably from 0.01 to 5% by weight, more preferably from 0.1 to 3.5% by weight and very particularly preferably from 0.15 to 2.5% by weight.
  • the means of the present application should be used to develop intensive colorings in the natural tone range, which reproduce as closely as possible the nuances produced with resorcinol-containing dyes, without having to rely on the use of resorcinol-type couplers .
  • Couplers of the resorcinol type or couplers from the group of resorcinols are understood to mean 1,3-dihydroxybenzene and its derivatives.
  • Derivatives of 1,3-dihydroxybenzene are all compounds that have a 1,3-dihydroxybenzene green structure and carry further substituents, although both hydroxy groups of 1,3-dihydroxybenzene must still be present.
  • Couplers from the group of resorcinols therefore include, in particular, resorcinol, 2-methylresorcinol and 4-chlororesorcinol.
  • couplers should be avoided in the agents of the present application, so it is preferred if the total amount of coupler-type oxidation dye precursors contained in the agent comes from the group of resorcinols, in particular from the group of resorcinol, 2-methylresorcinol and 4-chlororesorcinol , below 0.1% by weight, preferably below 0.05% by weight, particularly preferably below 0.01% by weight and most preferably at 0% by weight.
  • an agent according to the invention is therefore characterized in that - based on the total weight of the agent - the total amount of coupler-type oxidation dye precursors contained in the agent from the group of resorcinols, in particular from the group of resorcinol, 2-methylresorcinol and 4-chlororesorcinol, below 0.1% by weight, preferably below 0.05% by weight, particularly preferably below 0.01% by weight and very particularly is preferably 0% by weight.
  • the third component essential to the invention is the oxidative dye isatin (c).
  • Isatin is the compound of the formula (ISA), which can alternatively be referred to as 2,3-indoline-dione or as 2,3-dioxoindoline
  • Isatin has the CAS number 91-56-5.
  • isatin (c) is preferably contained in certain quantity ranges in the agent according to the invention. Particularly good results were obtained when the agent - based on the total weight of the agent - contained 0.001 to 10% by weight, preferably 0.01 to 5% by weight, more preferably 0.1 to 3.5% by weight. and very particularly preferably contained 0.15 to 2.5% by weight of isatin (c).
  • an agent according to the invention is therefore characterized in that - based on the total weight of the agent - it contains 0.001 to 10% by weight, preferably 0.01 to 5% by weight, more preferably 0.1 to 3%. 5% by weight and very particularly preferably 0.15 to 2.5% by weight of isatin (c).
  • Isatin can be purchased commercially from various suppliers such as Acros, Sigma Aldrich, Thermo Scientific, etc.
  • the nuance resulting from coloring the hair depends on the amount of developer(s) (a) and coupler(s) (b) used, as well as on the amount of isatin (c) contained in the agent. As is known from usual dyeing practice, the higher the amounts of developer (a), coupler (b) and isatin (c) used, the higher the intensity of the coloring. The naturalness of the However, the coloring obtained can be controlled by the quantitative ratio in which the developers of group (a) and isatin (c) are used in the oxidative colorant.
  • the colorings produced on the hair then had a particularly high similarity to the colorings obtained with resorcinol-type couplers when the agent contained the developers (a) and isatin (c) in a weight ratio of 2:1 to 1:2, preferably from 1.9:1 to 1:1, more preferably from 1.9:1 to 1.1:1, even more preferably from 1.8:1 to 1.1:1 and very particularly preferred from 1.7:1 to 1.2:1.
  • This effect was particularly observed in the darker natural shades such as dark brown and medium blonde.
  • an agent according to the invention is therefore characterized in that the weight ratio of all developers of group (a) contained in the agent to the isatin (c) contained in the agent, i.e. the weight ratio (a)/(c), is at one Value from 2:1 to 1:2, preferably from 1.9:1 to 1:1, more preferably from 1.9:1 to 1.1:1, even more preferably from 1.8:1 to 1.1 :1 and most preferably from 1.7:1 to 1.2:1.
  • the developer (or developers) (a) is used either in the same amount as isatin (c) or in up to 1.9 -fold excess weight is used on average.
  • the developers (a) are particularly preferably used in a 1.2-fold to 1.7-fold excess weight compared to isatin (c).
  • the oxidative dye according to the invention preferably contains at least one oxidizing agent (d), which is particularly preferably hydrogen peroxide and/or the addition products of hydrogen peroxide to organic or inorganic compounds.
  • hydrogen peroxide itself is used as an aqueous solution in the oxidative colorant.
  • concentration of a hydrogen peroxide solution is determined on the one hand by the legal requirements and on the other hand by the desired effect; Preferably 6 to 12% by weight solutions in water are used.
  • Oxidative preferred ones according to the invention are characterized in that they contain 0.5 to 20% by weight, preferably 1 to 12.5% by weight, more preferably 2.5 to 10% by weight and particularly preferably 3 to 8% by weight. % hydrogen peroxide, based on the total weight of the oxidative colorant.
  • an agent according to the invention is therefore characterized in that it
  • (d) contains at least one oxidizing agent from the group consisting of hydrogen peroxide and its addition products to organic or inorganic compounds.
  • an agent according to the invention is characterized in that - based on the total weight of the agent - it contains 0.5 to 20% by weight, preferably 1 to 12.5% by weight, more preferably 2.5 to 10 % by weight and particularly preferably 3 to 8% by weight of hydrogen peroxide (d).
  • direct dyes 0.5 to 20% by weight, preferably 1 to 12.5% by weight, more preferably 2.5 to 10 % by weight and particularly preferably 3 to 8% by weight of hydrogen peroxide (d).
  • the agents according to the invention can optionally contain at least one substantive dye.
  • These are dyes that are absorbed directly into the hair and do not require an oxidative process to form the color.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones, triarylmethane dyes or indophenols.
  • the direct dyes are each preferably used in an amount of 0.001 to 20% by weight, in particular 0.05 to 5% by weight, based on the entire application preparation.
  • the total amount of direct dyes is preferably at most 3% by weight.
  • Direct dyes can be divided into anionic, cationic and nonionic direct dyes, which are selected and used by the person skilled in the art according to the requirements of the carrier base.
  • Preferred anionic direct dyes are those under the international names or trade names Bromophenol blue, Tetrabromophenol blue, Acid Yellow 1, Yellow 10, Acid Yellow 23, Acid Yellow 36, Acid Orange 7, Acid Red 33, Acid Red 52, Pigment Red 57:1, Acid Blue 7, Acid Green 50, Acid Violet 43, Acid Black 1 and Acid Black 52 are known compounds.
  • Preferred cationic direct dyes are Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14, Basic Yellow 57, Basic Red 76, Basic Blue 16, Basic Blue 347 (Cationic Blue 347 / Dystar), HC Blue No. 16, Basic Blue 99, Basic Brown 16, Basic Brown 17, Yellow 87, Basic Orange 31 and Basic Red 51.
  • Nonionic nitro and quinone dyes and neutral azo dyes are particularly suitable as nonionic direct dyes.
  • Preferred nonionic direct dyes are those under the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, HC Orange 1, Disperse Orange 3, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, HC Red BN, HC Blue 2, HC Blue 11, HC Blue 12, Disperse Blue 3, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9 known compounds, as well 1,4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis-(2-hydroxyethyl)-amino-2-nitrobenzene, 3-nitro-4-(2-hydroxyethyl)- aminophenol, 2-(2-hydroxyethyl)amino-4,6-dinitrophenol, 4-[(2-hydroxyethyl)amino]-3-nitro-1-methylbenzene, 1-amino-4-(2-hydroxyethyl)-amino- 5-chloro-2-nitrobenzene, 4-a
  • Dyeing processes on keratin fibers usually take place in an alkaline environment. In order to protect the keratin fibers and the skin as much as possible, setting a pH value that is too high is not desirable. It is therefore preferred if the pH value of the ready-to-use agent is between 6 and 11, in particular between 7 and 10.5.
  • the pH values in the sense of the present invention are pH values that were measured at a temperature of 22 ° C.
  • the alkalizing agents that can be used according to the invention to adjust the preferred pH value can be from the group formed by ammonia, alkanolamines, basic amino acids, as well as inorganic alkalizing agents such as (earth) alkali metal hydroxides, (earth) alkali metal metasilicates, (earth) alkali metal phosphates and ( Earth alkali metal hydrogen phosphates can be selected.
  • Preferred inorganic alkalinizing agents are magnesium carbonate, sodium hydroxide, potassium hydroxide, sodium silicate and sodium metasilicate.
  • Organic alkalinizing agents that can be used according to the invention are preferably selected from monoethanolamine, 2-amino-2-methylpropanol and triethanolamine.
  • the basic amino acids that can be used as alkalizing agents according to the invention are preferably selected from the group formed by arginine, lysine, ornithine and histidine, particularly preferably arginine. other ingredients in the agent
  • an emulsifier or a surfactant is also added to the oxidative colorants, with surface-active substances depending on the area of application as surfactants or as emulsifiers and are selected from anionic, cationic, zwitterionic, amphoteric and nonionic surfactants and emulsifiers.
  • an agent according to the invention is therefore characterized in that it contains at least one surfactant selected from the group of anionic, amphoteric, zwitterionic and nonionic surfactants.
  • anionic surface-active substances suitable for use on the human body are suitable as anionic surfactants in agents according to the invention. These are characterized by a water-solubilizing, anionic group such as a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with around 8 to 30 carbon atoms.
  • anionic group such as a carboxylate, sulfate, sulfonate or phosphate group
  • a lipophilic alkyl group with around 8 to 30 carbon atoms.
  • the molecule may contain glycol or polyglycol ether groups, ester, ether and amide groups as well as hydroxyl groups.
  • anionic surfactants are, each in the form of the sodium, potassium and ammonium as well as the mono, di- and trialkanolammonium salts with 2 to 4 carbon atoms in the alkanol group, linear and branched fatty acids with 8 to 30 carbon atoms ( Soap),
  • Alkyl sulfates and alkyl ether sulfates of the formula RO(CH2CH2O) X SO3H, in which R is a preferably linear alkyl group with 8 to 30 carbon atoms and x 0 or 1 to 12,
  • Esters of tartaric acid and citric acid with alcohols which represent addition products of about 2-15 molecules of ethylene oxide and/or propylene oxide with fatty alcohols with 8 to 22 carbon atoms, alkyl and/or alkenyl ether phosphates of the formula in which R preferably represents an aliphatic, optionally unsaturated hydrocarbon radical with 8 to 30 carbon atoms, R' represents hydrogen, a radical (CH2CH2O) y R and x and y independently represent a number from 1 to 10, sulfated fatty acid alkylene glycol esters of the formula RC( O)O(alkO) n SO3H, in which R represents a linear or branched, aliphatic, saturated and/or unsaturated alkyl radical with 6 to 22 carbon atoms, alk represents CH2CH2, CHCH3CH2 and/or CH2CHCH3 and n represents a number of 0 .5 to 5, monoglyceride sulfates and monoglyceride ether
  • Preferred anionic surfactants are alkyl sulfates, alkyl ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule.
  • Zwitterionic surfactants are those surface-active compounds that have at least one quaternary ammonium group and at least one carboxylate, sulfonate or sulfate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N,N-dimethylammonium glycinates, for example cocoacylaminopropyl-dimethylammonium glycinate, and 2-alkyl -3-carboxymethyl-3-hydroxyethyl-imidazolines, each with 8 to 18 carbon atoms in the alkyl or acyl group, as well as the cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • a preferred zwitterionic surfactant is
  • Amphoteric surfactants are those surface-active compounds which, in addition to a Cs-C24 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SOsH group in the molecule and are capable of forming internal salts.
  • amphoteric surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 24 carbon atoms in the alkyl group.
  • Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2-Ci8-acylsarcosine.
  • Non-ionic surfactants included as hydrophilic group e.g. B. a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group. Examples of such connections are:
  • Polyglycerol esters and alkoxylated polyglycerol esters such as poly(3)glycerol diisostearate (commercial product: Lameform®TGI (Henkel)) and poly(2)glycerol polyhydroxy stearate
  • Polyol fatty acid esters such as the commercial product Hydagen® HSP (Cognis) or Sovermol types (Cognis), higher alkoxylated, preferably propoxylated and especially ethoxylated, mono-, di- and triglycerides, such as glycerol monolaurate + 20 ethylene oxide and glycerol monostearate + 20 ethylene oxide, amine oxides,
  • Sorbitan fatty acid esters and addition products of ethylene oxide to sorbitan fatty acid esters such as the polysorbates and sorbitan monolaurate + 20 mol of ethylene oxide (EO), sugar fatty acid esters and addition products of ethylene oxide to sugar fatty acid esters, addition products of ethylene oxide to fatty acid alkanolamides and fatty amines, fatty acid N-alkylglucamides,
  • Preferred representatives of this class are, for example, nonylphenol + 9 EO and octylphenol + 8 EO;
  • the alkyl polyglycosides that can be used according to the invention can only contain a specific alkyl radical R. However, these compounds are usually made from natural fats and oils or mineral oils. In this case, the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the respective workup of these compounds.
  • C8-C22 alkyl mono- and oligoglycosides and their ethoxylated analogues are particularly suitable as nonionic surfactants. In particular, the non-ethoxylated compounds have proven to be particularly suitable.
  • sugar building block Z any mono- or oligosaccharides can be used as the sugar building block Z.
  • Sugars with 5 or 6 carbon atoms and the corresponding oligosaccharides are usually used.
  • Such sugars are, for example, glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, old rose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar building blocks are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides that can be used according to the invention contain on average 1.1 to 5 sugar units. Alkyl polyglycosides with x values of 1.1 to 2.0 are preferred. Alkyl glycosides in which x is 1.1 to 1.8 are very particularly preferred.
  • alkoxylated homologues of the alkyl polyglycosides mentioned can also be used according to the invention. These homologs can contain on average up to 10 ethylene oxide and/or propylene oxide units per alkyl glycoside unit.
  • alkylene oxide addition products to saturated linear fatty alcohols and fatty acids each containing 2 to 30 moles of ethylene oxide per mole of fatty alcohol or fatty acid, have proven to be further preferred nonionic surfactants.
  • Preparations with excellent properties are also obtained if they contain fatty acid esters of ethoxylated glycerin as nonionic surfactants.
  • nonionic surface-active substances are substances that are commercially available in pure form as solids or liquids.
  • the definition of purity in this context does not refer to chemically pure compounds. Rather, especially when it comes to natural-based products, Mixtures of different homologues are used, for example with different alkyl chain lengths, as are obtained in products based on natural fats and oils. Even with alkoxylated products there are usually mixtures of different degrees of alkoxylation.
  • the term purity refers rather to the fact that the substances selected should preferably be free of solvents, additives and other accompanying substances.
  • both products with a "normal” homolog distribution and those with a narrow homolog distribution can be used.
  • “Normal” homolog distribution means mixtures of homologs that are obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts. Narrowed homolog distributions, on the other hand, are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution may be preferred.
  • anionic, nonionic, zwitterionic or amphoteric surfactants are used in amounts of 0.1 to 45% by weight, preferably 1 to 30% by weight and very particularly preferably 1 to 15% by weight, based on the total amount of the agent ready for use .
  • quaternary ammonium compounds are ammonium halides, especially chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B.
  • cetyltrimethylammonium chloride stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83.
  • the long alkyl chains of the surfactants mentioned above preferably have 10 to 18 carbon atoms.
  • Further cationic surfactants that can be used according to the invention are the quaternized protein hydrolysates.
  • the alkylamidoamines are usually produced by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines and, in addition to a good conditioning effect, are particularly characterized by their good biodegradability.
  • An inventive A particularly suitable compound from this group of substances is stearamidopropyl-dimethylamine, which is commercially available under the name Tegoamid® S 18.
  • Esterquats are also very biodegradable. Esterquats are known substances that contain both at least one ester function and at least one quaternary ammonium group as a structural element. Preferred esterquats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyl dialkylamines. Such products are sold, for example, under the trademarks Stepantex®, Dehyquart® and Armocare®.
  • the cationic surfactants are preferably contained in the agents used according to the invention in amounts of 0.05 to 10% by weight, based on the agent as a whole. Amounts of 0.1 to 5% by weight are particularly preferred.
  • nonionic, zwitterionic and/or amphoteric surfactants and mixtures thereof may be preferred.
  • the effect of the active ingredient according to the invention can be increased by emulsifiers.
  • emulsifiers are:
  • Ci2-C22 fatty acid mono- and diesters of addition products of 1 to 30 mol of ethylene oxide with polyols with 3 to 6 carbon atoms, in particular with glycerol,
  • sterols whereby sterols are understood to be a group of steroids that carry a hydroxyl group on carbon atom 3 of the steroid structure and are isolated both from animal tissue (zoosterols) and from vegetable fats (phytosterols).
  • zoosterols are cholesterol and lanosterol.
  • suitable phytosterols are ergosterol, stigmasterol and sitosterol.
  • mycosterols are also isolated from fungi and yeasts.
  • Phospholipids especially glucose phospholipids, e.g. B. as lecithins or phosphatidylcholines from e.g. egg yolks or plant seeds (e.g. soybeans), fatty acid esters of sugars and sugar alcohols, such as sorbitol
  • Polyglycerols and polyglycerol derivatives such as polyglycerol poly-12-hydroxystearate (commercial product Dehymuls® PGPH)
  • Linear and branched fatty acids with 8 to 30 carbon atoms and their Na, K, ammonium, Ca, Mg and Zn salts.
  • the agents according to the invention preferably contain the emulsifiers in amounts of 0.1 to 25% by weight, in particular 0.5 to 15% by weight, based on the total amount of the agent ready for use.
  • Non-ionic emulsifiers or surfactants with an HLB value of 10-15 can be particularly preferred according to the invention.
  • emulsifiers which do not contain ethylene oxide and/or propylene oxide in the molecule may be particularly preferred.
  • an agent according to the invention is characterized in that - based on the total weight of the agent - the total amount of fat components contained in the agent is below 25% by weight, preferably below 20% by weight, more preferably below 15 % by weight and most preferably below 13% by weight.
  • fat components are understood to mean organic compounds with a solubility in water at room temperature (22 ° C) and atmospheric pressure (760 mmHg) of less than 1% by weight, preferably less than 0.1% by weight.
  • the definition of fat components explicitly only includes uncharged (ie non-ionic) compounds.
  • Fat components have at least one saturated or unsaturated alkyl group with at least 8 carbon atoms.
  • the molecular weight of the fat components is a maximum of 5000 g/mol, preferably a maximum of 2500 g/mol and particularly preferably a maximum of 1000 g/mol.
  • the fat components are neither polyoxyalkylated nor polyglycerylated compounds.
  • fat components are understood to be the components from the group of C12-C30 fatty alcohols, Ci2-C3o fatty acid triglycerides and/or hydrocarbons.
  • non-ionic substances are explicitly considered as fat components.
  • Charged compounds such as fatty acids and their salts are not considered fat components.
  • the Ci2-C30 fatty alcohols can be saturated, mono- or polyunsaturated, linear or branched fatty alcohols with 12 to 30 carbon atoms.
  • Ci2-C30 fatty alcohols examples include dodecan-1-ol (dodecyl alcohol, lauryl alcohol), tetradecan-1-ol (tetradecyl alcohol, myristyl alcohol), hexadecan-1-ol (hexadecyl alcohol, cetyl alcohol, palmityl alcohol), octadecane -1-ol (octadecyl alcohol, stearyl alcohol), arachyl alcohol (eicosan-1-ol), heneicosyl alcohol (heneicosan-1-ol) and/or behenyl alcohol (docosan-1-ol).
  • dodecan-1-ol dodecyl alcohol, lauryl alcohol
  • tetradecan-1-ol tetradecyl alcohol, myristyl alcohol
  • hexadecan-1-ol hexadecyl alcohol, cetyl alcohol, palmityl alcohol
  • Linear, unsaturated fatty alcohols are, for example, (9Z)-octadec-9-en-1-ol (oleyl alcohol), (9E)-octadec-9-en-1-ol (elaidyl alcohol), (9Z,12Z)-octadeca-9, 12-dien-1-ol (linoleyl alcohol), (9Z,12Z,15Z)-octadeca-9,12,15-trien-1-ol (linolenoyl alcohol), gadoleyl alcohol ((9Z)-eicos-9-en-1- ol), arachidone alcohol ((5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraen-1-ol), erucyl alcohol ((13Z)-docos-13-en-1-ol) and/ or brassidyl alcohol ((13E)-docosen-1-ol).
  • Ci2-C3o fatty acid triglyceride is understood to mean the triester of the trihydric alcohol glycerol with three equivalents of fatty acid. Both structurally identical and different fatty acids within a triglyceride molecule can be involved in the ester formation.
  • fatty acids are to be understood as meaning saturated or unsaturated, unbranched or branched, unsubstituted or substituted Ci2-C3o carboxylic acids.
  • Unsaturated fatty acids can be monounsaturated or polyunsaturated. In the case of an unsaturated fatty acid, its C-C double bond(s) can have the cis or trans configuration.
  • esters based on glycerol with a fatty acid are esters based on glycerol with a fatty acid, the fatty acid being selected from the group consisting of dodecanoic acid (lauric acid), tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), tetracosanoic acid (lignoceric acid), octadecanoic acid (stearic acid), eicosanoic acid ( Arachidic acid), docosanoic acid (behenic acid), petroselinic acid [(Z)-6-octadecenoic acid], palmitoleic acid [(9Z)-hexadec-9-enoic acid], oleic acid [(9Z)-octadec-9-enoic acid], elaidine acid [(9E) -Octadec-9-enoic acid], erucic acid [(13Z)-doco
  • the fatty acid triglycerides can also be of natural origin.
  • Hydrocarbons are compounds consisting exclusively of carbon and hydrogen atoms with 8 to 80 carbon atoms. Particularly preferred in this context are aliphatic hydrocarbons such as mineral oils, liquid paraffin oils (e.g. Paraffinium Liquidum or Paraffinum Perliquidum), isoparaffin oils, semi-solid paraffin oils, paraffin waxes, hard paraffin (Paraffinum Solidum), Vaseline and polydecenes.
  • Paraffinum Liquidum and Paraffinium Perliquidum have proven to be particularly suitable in this context.
  • the hydrocarbon is particularly preferably paraffinum liquidum, also called white oil.
  • Paraffinum Liquidum is a mixture of purified, saturated, aliphatic hydrocarbons, which largely consists of hydrocarbon chains with a C chain distribution of 25 to 35 C atoms.
  • the products according to the invention contain at least one stabilizer or complexing agent.
  • Common complexing agents and stabilizers that are preferred in the context of the present invention are, for example, polyoxycarboxylic acids, polyamines, ethylenediaminetetraacetic acid (EDTA), N-hydroxyethylethylenediaminetriacetic acid, diethylenetriaminepentaacetic acid (DTPA), ethylenediaminedisuccinic acid (EDDS), hydroxyethyliminodiacetic acid, nitridodiacetic acid-3-propionic acid, isoserine diacetic acid, N,N-Di-(2-hydroxy-ethyl)glycine, N-(1,2-dicarboxy-2-hydroxyethyl)glycine, N-(1,2-dicarboxy-2-hydroxyethyl)aspartic acid or nitrilotriacetic acid (NTA), Ethylenediamine diglutaric acid (EDGA), 2-hydroxyprop
  • these complexing agents are at least partially present as anions. It is irrelevant whether they are introduced in the form of acids or in the form of salts. If used as salts, alkali metal, ammonium or alkyl ammonium salts, in particular sodium salts, are preferred.
  • Complexing agents preferred according to the invention are nitrogen-containing polycarboxylic acids, in particular EDTA, and phosphonates, preferably hydroxyalkane or aminoalkane phosphonates and in particular 1-hydroxyethane-1,1-diphosphonate (HEDP) or its di- or tetrasodium salt and / or ethylenediaminetetramethylene phosphonate (EDTMP) or its Hexasodium salt and/or diethylene triamine pentamethylene phosphonate (DTPMP) or its hepta or octasodium salt.
  • HEDP 1-hydroxyethane-1,1-diphosphonate
  • EDTMP ethylenediaminetetramethylene phosphonate
  • DTPMP diethylene triamine pentamethylene phosphonate
  • the colorants according to the invention preferably contain further auxiliaries and additives. According to the invention, it has proven to be preferred if the agents contain at least one thickener. There are no fundamental restrictions with regard to these thickeners. Both organic and purely inorganic thickeners can be used.
  • the thickener is an anionic, synthetic polymer.
  • Preferred anionic groups are the carboxylate and sulfonate groups.
  • anionic monomers from which the polymeric anionic thickeners can consist are acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic anhydride and 2-acrylamido-2-methylpropanesulfonic acid.
  • the acidic groups can be present in whole or in part as sodium, potassium, ammonium, mono- or triethanolammonium salt.
  • Preferred monomers are maleic anhydride and, in particular, 2-acrylamido-2-methylpropanesulfonic acid and acrylic acid.
  • Preferred anionic homopolymers are uncrosslinked and crosslinked polyacrylic acids. Allyl ethers of pentaerythritol, sucrose and propylene can be preferred crosslinking agents. Such compounds are commercially available, for example, under the trademark Carbopol®. Also preferred is the homopolymer of 2-acrylamido-2-methylpropanesulfonic acid, which is commercially available, for example, under the name Rheotik®11-80.
  • copolymers of at least one anionic monomer and at least one nonionic monomer are acrylamide, methacrylamide, acrylic acid esters, methacrylic acid esters, itaconic acid mono- and diesters, vinylpyrrolidinone, vinyl ethers and vinyl esters.
  • the anionic acrylic acid and/or methacrylic acid polymers or copolymers are preferably present in the agents according to the invention in an amount of 0.1 to 10% by weight, particularly preferably 1 to 5% by weight, based in each case on the weight of the Means, included.
  • Preferred anionic copolymers are, for example, copolymers of acrylic acid, methacrylic acid or their Ci-Ce alkyl esters, as sold under the INCI declaration Acrylates Copolymers.
  • a preferred commercial product is, for example, Aculyn® 33 from Rohm & Haas.
  • copolymers of acrylic acid, methacrylic acid or their Ci-Ce alkyl esters and the esters of an ethylenically unsaturated acid and an alkoxylated fatty alcohol are, in particular, acrylic acid, methacrylic acid and itaconic acid;
  • Suitable alkoxylated fatty alcohols are, in particular, Steareth-20 or Ceteth-20.
  • Such copolymers are sold by Rohm & Haas under the trade name Aculyn® 22 and by National Starch under the trade names Structure® 2001 and Structure® 3001.
  • Preferred anionic copolymers are also acrylic acid-acrylamide copolymers and in particular polyacrylamide copolymers with monomers containing sulfonic acid groups.
  • a particularly preferred anionic copolymer consists of 70 to 55 mol% acrylamide and 30 to 45 mol% 2-acrylamido-2-methylpropanesulfonic acid, where the sulfonic acid group is wholly or partly as sodium, potassium, ammonium, mono- or triethanolammonium. Salt is present.
  • This copolymer can also be crosslinked, polyolefinically unsaturated compounds such as tetraallyloxythane, allyl sucrose, allyl pentaerythritol and methylene bisacrylamide being preferably used as crosslinking agents.
  • a polymer is contained in the commercial products Sepigel®305 and Simulgel® 600 from SEPPIC.
  • a maleic acid-methyl vinyl ether copolymer crosslinked with 1,9-decadiene is commercially available under the name Stabileze® QM.
  • the thickener is a cationic synthetic polymer.
  • Preferred cationic groups are quaternary ammonium groups.
  • polymers in which the quaternary ammonium group is bonded via a C1-C4 hydrocarbon group to a polymer main chain made up of acrylic acid, methacrylic acid or their derivatives have proven to be particularly suitable.
  • R1 represents a methyl group R2, R3 and R4 stand for methyl groups m has the value 2,
  • Halide ions especially chloride, are preferred.
  • a particularly suitable homopolymer is the, if desired crosslinked, poly(methacryloxyethyltrimethylammonium chloride) with the INCI name Polyquaternium-37.
  • the crosslinking can be carried out using polyolefinically unsaturated compounds, for example divinylbenzene, tetraallyloxyethane, methylene bisacrylamide, diallyl ether, polyallyl polyglyceryl ether, or allyl ethers of sugars or sugar derivatives such as erythritol, pentaerythritol, arabitol, mannitol, sorbitol, sucrose or glucose.
  • Methylenebisacrylamide is a preferred crosslinking agent.
  • the homopolymer is preferably used in the form of a non-aqueous polymer dispersion, which should not have a polymer content of less than 30% by weight.
  • a non-aqueous polymer dispersion which should not have a polymer content of less than 30% by weight.
  • Such polymer dispersions are available under the names Salcare® SC 95 (approx. 50% polymer content, further component: mineral oil (INCI name: Mineral Oil) and tridecyl-polyoxypropylene-polyoxyethylene ether (INCI name: PPG-1-Trideceth-6) ) and Salcare® SC 96 (approx.
  • Copolymers with monomer units according to formula (HP-1) preferably contain acrylamide, methacrylamide, Ci-C4 alkyl acrylate and Ci-C4 alkyl methacrylate as nonionic monomer units. Among these nonionic monomers, acrylamide is particularly preferred. These copolymers can also be crosslinked, as described above in the case of homopolymers. A preferred copolymer according to the invention is the crosslinked acrylamide-methacroyloxyethyltrimethylammonium chloride copolymer. Such copolymers, in which the monomers are present in a weight ratio of approximately 20:80, are commercially available as an approximately 50% non-aqueous polymer dispersion under the name Salcare® SC 92.
  • naturally occurring thickeners are used.
  • Preferred thickeners in this embodiment are, for example, non-ionic guar gum.
  • both modified and unmodified guar gums can be used.
  • Unmodified guargums for example, are sold under the trade name Jaguar® C distributed by Rhone Poulenc.
  • Modified guar gums preferred according to the invention contain Ci-Ce hydroxyalkyl groups. The groups hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl are preferred. Guargums modified in this way are known in the art and can be produced, for example, by reacting the guargums with alkylene oxides.
  • the degree of hydroxyalkylation which corresponds to the number of alkylene oxide molecules consumed in relation to the number of free hydroxyl groups of the guar gum, is preferably between 0.4 and 1.2.
  • Guargums modified in this way are commercially available under the trade names Jaguar® HP8, Jaguar® HP60, Jaguar® HP120, Jaguar® DC 293 and Jaguar® HP105 from Rhone Poulenc.
  • biosaccharide gums of microbial origin such as the scleroglucangums or xanthan gums
  • gums from plant exudates such as gum arabic, ghatti gum, karaya gum, tragacanth gum, carrageenan gum, agar agar, locust bean gum, pectins
  • Alginates, starch fractions and derivatives such as amylose, amylopectin and dextrins, cellulose derivatives such as methylcellulose, carboxyalkylcelluloses and hydroxyalkylcelluloses.
  • Preferred hydroxyalkyl celluloses are in particular the hydroxyethyl celluloses, which are sold under the names Cellosize® from Amerchol and Natrosol® from Hercules.
  • Suitable carboxyalkyl celluloses are in particular the carboxymethyl celluloses, as sold under the names Blanose® by Aquaion, Aquasorb® and Ambergum® by Hercules and Cellgon® by Montello.
  • Starch and its derivatives are also preferred.
  • Starch is a storage substance in plants that occurs primarily in tubers and roots, in grain seeds and in fruits and can be obtained in high yields from a variety of plants.
  • the polysaccharide which is insoluble in cold water and forms a colloidal solution in boiling water, can be obtained, for example, from potatoes, cassava, batata, maranta, corn, cereals, rice, legumes such as peas and beans, bananas or the pulp of certain palm varieties (for example the sago palm).
  • Natural starches obtained from plants and/or chemically or physically modified starches can be used according to the invention. A modification can be achieved, for example, by introducing different functional groups on one or more of the hydroxyl groups of the starch.
  • esters, ethers or amides of starch with optionally substituted Ci-C4o radicals are usually esters, ethers or amides of starch with optionally substituted Ci-C4o radicals.
  • One etherified with a 2-hydroxypropyl group is particularly advantageous Corn starch, such as that sold by National Starch under the trade name Amaze®.
  • nonionic, fully synthetic polymers such as polyvinyl alcohol or polyvinylpyrrolidinone
  • thickeners can also be used as thickeners according to the invention.
  • Preferred nonionic, fully synthetic polymers are sold, for example, by BASF under the trade name Luviskol®.
  • Luviskol® Luviskol®
  • nonionic polymers also enable a significant improvement in the sensory feel of the resulting preparations.
  • Layered silicates (polymeric, crystalline sodium disilicates) have proven to be particularly suitable as inorganic thickeners for the purposes of the present invention.
  • clays in particular magnesium aluminum silicates, such as bentonite, especially smectites, such as montmorillonite or hectorite, which can optionally also be suitably modified, and synthetic layered silicates, such as the magnesium layered silicate sold by Süd Chemie under the trade name Optigel®, are preferred .
  • At least one optionally hydrated SiCh compound is preferably additionally added.
  • the optionally hydrated SiCh compounds in amounts of 0.05% by weight to 15% by weight, particularly preferably in amounts of 0.15% by weight to 10% by weight and very particularly preferably used in amounts of 0.2% by weight to 5% by weight, in each case based on the agents according to the invention.
  • the quantities indicate the content of the SiO2 compounds (without their water content) in the products.
  • the present invention is in principle not subject to any restrictions.
  • Silicas, their oligomers and polymers and their salts are preferred.
  • Preferred salts are the alkali salts, especially the potassium and sodium salts.
  • the sodium salts are particularly preferred.
  • the optionally hydrated SiO2 compounds can be present in various forms.
  • the SiO2 compounds are preferably used in the form of silica gels (silica gel) or, particularly preferably, as water glass. Some of these SiO2 compounds can be present in aqueous solution.
  • water glasses which are formed from a silicate of the formula (SiO2)n(Na 2 O) m (K2O)p are particularly preferred, where n stands for a positive rational number and m and p independently stand for a positive rational number or for 0, with the provisos that at least one of the parameters m or p is different from 0 and the ratio between n and the sum of m and p is between 1:4 and 4:1. Metasilicates in which the ratio between n and the sum of m and p is 1:2 or less are preferred.
  • the water glasses can also contain small amounts of other additives, such as phosphates or magnesium salts.
  • Water glasses that are particularly preferred according to the invention are sold, among others, by the company Henkel under the names Ferrosil® 119, Natro nwasserg las 40/42, Portil® A, Portil® AW and Portil® W and by the company Akzo under the name Britesil® C20.
  • the oxidative colorants are preferably formulated as flowable preparations.
  • agents according to the invention can contain other active ingredients, auxiliaries and additives, such as nonionic polymers such as vinylpyrrolidinone/vinylacrylate copolymers, polyvinylpyrrolidinone, vinylpyrrolidinone/vinylacetate copolymers, polyethylene glycols and polysiloxanes;
  • nonionic polymers such as vinylpyrrolidinone/vinylacrylate copolymers, polyvinylpyrrolidinone, vinylpyrrolidinone/vinylacetate copolymers, polyethylene glycols and polysiloxanes;
  • Silicones such as volatile or non-volatile, straight-chain, branched or cyclic, cross-linked or non-cross-linked polyalkylsiloxanes (such as dimethicones or cyclomethicones), polyarylsiloxanes and/or polyalkylarylsiloxanes, in particular polysiloxanes with organofunctional groups, such as substituted or unsubstituted amines (amodimethicones), carboxyl, alkoxy - and/or hydroxyl groups (dimethicone copolyols), linear polysiloxane (A)-polyoxyalkylene (B) block copolymers, grafted silicone polymers with a non-silicone-containing, organic backbone or with a polysiloxane backbone, such as that under the INCI name Bis-PEG/PPG- 20/20 Dimethicone commercial product Abil B 8832 from Degussa, or mixtures thereof; cationic polymers such
  • copolymers dimethylaminoethyl methacrylate-vinylpyrrolidinone copolymers quaternized with diethyl sulfate, vinylpyrrolidinone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol; zwitterionic and amphoteric polymers such as acrylamidopropyl-trimethylammonium chloride/acrylate copolymers and octylacrylamide/methyl methacrylate/tert-butylaminoethyl methacrylate/2-hydroxypropyl methacrylate copolymers, diallyldimethylammonium chloride/acrylate copolymers, t-butylaminoethyl methacrylate/N-(1,1 ,3,3-Tetramethylbutyl)acrylamide/acrylate(/methacrylate) copolymers, anionic polymers such as polyacrylic acids, cross-linked polyacrylic acids, vinyl acetate
  • Copolymers and acrylic acid/ethyl acrylate/N-t-butyl acrylamide terpolymers, other thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. B. methylcellulose, hydroxyalkylcellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B. bentonite or fully synthetic hydrocolloids such as. B.
  • polyvinyl alcohol such as glucose, maleic acid and lactic acid
  • hair conditioning compounds such as phospholipids, for example soy lecithin, egg lecitin and cephalins as well as silicone oils, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol, active ingredients that improve fiber structure, in particular mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose, quaternized amines such as methyl-1-alkylamidoethyl-2 -alkylimidazolinium methosulfate defoamers such as silicones, dyes for coloring the agent, anti-dandruff active ingredients such as piroctone olamine, zinc omadine and climbazole, amino acids and oligopeptides, in particular arginine and/or serine,
  • active ingredients that improve fiber structure in particular mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose, quaternized amines such as methyl-1-
  • Animal and/or plant-based protein hydrolysates such as elastin, collagen, keratin, silk and milk protein protein hydrolysates, or almond, rice, pea, potato and wheat protein hydrolysates, as well as in the form of their fatty acids Condensation products or optionally anionically or cationically modified derivatives, vegetable oils, for example macadamia nut oil, kukui nut oil, palm oil, amaranth seed oil, peach kernel oil, avocado oil, olive oil, coconut oil, rapeseed oil, sesame oil, jojoba oil, soybean oil, peanut oil, evening primrose oil and tea tree oil light stabilizers, in particular derivatized benzophenones, cinnamic acid derivatives and triazines, Substances for adjusting the pH value, such as common acids, especially recreational acids and bases,
  • Active ingredients such as panthenol, pantothenic acid, pantolactone, allantoin, pyrrolidinone carboxylic acids and their salts as well as bisabolol,
  • Polyphenols in particular hydroxycinnamic acids, 6,7-dihydroxycoumarins, hydroxybenzoic acids, catechins, tannins, leucoanthocyanidins, anthocyanidins, flavanones, flavones and flavonols;
  • Ceramides preferably the sphingolipids such as ceramides I, ceramides II, ceramides 1, ceramides 2, ceramides 3, ceramides 5 and ceramides 6, or pseudoceramides, such as in particular N-(Cs-C22-acyl)-(C8-C22-acyl)- hydroxyproline,
  • Vitamins, provitamins and vitamin precursors especially those of groups A, B3, Bs, Be, C, E, F and H,
  • Plant extracts such as the extracts of aloe vera, angelica, anise, apricot, benzoin, bergamot, birch, nettle, calmus, cassis, costus, marshmallow, oak bark, elemi, tarragon, spruce needle, galbanum, geranium, ginseng, grapefruit, guaiac wood, green Tea, witch hazel, hazel, hops, coltsfoot, ginger root, iris, jasmine, chamomile, cardamom, clover, burdock root, pine, kiwi, coconut, coriander, caraway, mountain pine, lavender, lemongrass, lily, lime, lime blossom, litchi, mace, Mallow, almond, mango, lemon balm, melon, meristem, myrrh, neroli, olibanum, opoponax, orange, patchouli, petitgrain, pine, thyme, rooibos, roses,
  • Consistency agents such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as spermaceti, beeswax, montan wax and paraffins,
  • Pearlescent agents such as ethylene glycol mono- and distearate as well as PEG-3 distearate, pigments,
  • Stabilizing agents for hydrogen peroxide and other oxidizing agents propellants such as propane-butane mixtures, N2O, dimethyl ether, CO2 and air, antioxidants.
  • the additional active ingredients and auxiliary substances are preferably used in the agents according to the invention in amounts of 0.0001 to 10% by weight, in particular 0.0005 to 5% by weight, based on the total weight of the application mixture.
  • Multi-component packaging unit (kit-of-parts)
  • the agents according to the invention are agents for oxidative dyeing or dyeing and lightening hair.
  • the oxidation dye precursors react with the oxidizing agent to form the actual dyes.
  • the agents according to the invention are therefore usually formulated as multi-component agents, usually as two-component agents.
  • the first component contains the oxidation dye precursors (a) and (b) as well as isatin (c), which is mixed with a second component containing the oxidizing agent (d) shortly before use. Both components are usually mixed together in a ratio of 1:3 to 3:1, preferably 1:2 to 2:1.
  • This mixture of the component containing color cream and optionally alkalizing agent and the component containing oxidizing agent is referred to as the application mixture or the ready-to-use agent.
  • a second object of the present invention is a multi-component packaging unit (kit-of-parts) for the oxidative coloring of keratin fibers, in particular human hair, comprising, separately assembled, a first container with a dye (F), which contains
  • the colorant can alternatively be referred to as a color cream.
  • Method for the oxidative coloring of ketatin fibers
  • oxidative colorant according to the invention of the first subject of the invention or the multi-component packaging unit are ideal for use in corresponding coloring processes
  • a further subject of the present invention is therefore a method for the oxidative dyeing of keratin fibers, in particular human hair, in which an agent, as disclosed in detail in the description of the first subject of the invention, is applied to the keratin fibers and rinsed out again after an exposure time becomes.
  • the agent While the agent is acting on the fiber, it can be advantageous to support the dyeing process by applying heat.
  • the heat can be supplied by an external heat source, such as warm air from a warm air blower, as well as, particularly when dyeing hair on a living subject, by the subject's body temperature.
  • the area to be dyed is usually covered with a hood.
  • the temperature during the exposure time is between 10 °C and 45 °C, in particular between 20 °C and 40 °C.
  • the dyes according to the invention produce intensive coloring even at physiologically tolerable temperatures of below 45 ° C. They are therefore particularly suitable for dyeing human hair.
  • the base formulation for the color cream described in Table 1 was prepared. The ones in the
  • the nuances of these dyes showed an almost exact color match with the resorcinol-containing dyes known from the prior art based on the color creams F1, F3 and F5.
  • Nuances in the natural tone range with a reddish color could also be obtained by using dyes according to the invention using the color creams F8, F10 and F12.
  • the shades in the red-blonde and copper-blond range also matched very well in color with the resorcinol-containing dyes known from the prior art based on the color creams F7, F9 and F11.
  • the base formulation for the color cream described in Table 1 was prepared.
  • the mixtures of oxidation dye precursors described in Table 4 were each incorporated into the color cream.
  • Each of the color creams produced in this way was mixed with the oxidizing agent preparation OX in a ratio of 1:1.
  • Each of the ready-to-use dyes prepared in this way was then applied to a strand of hair (Kerling company, natural white) and left there for a period of 30 minutes.
  • the application mixture was then rinsed out with a shampoo and dried.
  • the hair strands were then measured colorimetrically (measuring the Lab values).
  • Table 4 (all information in% by weight, based on the total weight of the color cream) Table 4 continued (all information in% by weight, based on the total weight of the color cream)

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Abstract

La présente invention concerne un agent de coloration oxydative de fibres kératiniques, en particulier de cheveux humains, contenant dans un support cosmétique (a) au moins un précurseur de colorant d'oxydation du type révélateur, et (b) au moins un précurseur de colorant d'oxydation du type coupleur, et (c) de l'isatine.
EP23700397.5A 2022-03-21 2023-01-03 Agent de coloration oxydative de fibres de kératine, contenant au moins un précurseur de colorant d'oxydation du type révélateur, au moins un précurseur de colorant d'oxydation du type coupleur et de l'isatine Pending EP4496556A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102022202753.1A DE102022202753B3 (de) 2022-03-21 2022-03-21 Mittel zur oxidativen Färbung von Keratinfasern, enthaltend mindestens ein Oxidationsfarbstoff-vorprodukt vom Entwicklertyp, mindestens ein Oxidationsfarbstoffvorprodukt vom Kupplertyp und Isatin
PCT/EP2023/050060 WO2023179919A1 (fr) 2022-03-21 2023-01-03 Agent de coloration oxydative de fibres de kératine, contenant au moins un précurseur de colorant d'oxydation du type révélateur, au moins un précurseur de colorant d'oxydation du type coupleur et de l'isatine

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EP4496556A1 true EP4496556A1 (fr) 2025-01-29

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EP23700397.5A Pending EP4496556A1 (fr) 2022-03-21 2023-01-03 Agent de coloration oxydative de fibres de kératine, contenant au moins un précurseur de colorant d'oxydation du type révélateur, au moins un précurseur de colorant d'oxydation du type coupleur et de l'isatine

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US (1) US20250017838A1 (fr)
EP (1) EP4496556A1 (fr)
DE (1) DE102022202753B3 (fr)
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DE2716671A1 (de) * 1977-04-15 1978-10-19 Henkel Kgaa Haarfaerbemittel
DE19717282A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Verwendung von 1-substituierten Isatinen zum Färben von keratinhaltigen Fasern
DE102009029043A1 (de) 2009-08-31 2011-03-03 Henkel Ag & Co. Kgaa Intensive, schonende Färbemittel
DE102011081190A1 (de) * 2011-08-18 2013-02-21 Henkel Ag & Co. Kgaa Mittel zum Behandeln keratinischer Fasern, enthaltend spezifische Aminosilikone und Alkali-sierungsmittel
US12485076B2 (en) * 2019-03-19 2025-12-02 Kao Corporation Liquid hair dye composition

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