EP3223789A1 - Agents de coloration de fibres kératiniques contenant au moins un colorant azoïque cationique comprenant deux groupes hétérocycliques - Google Patents

Agents de coloration de fibres kératiniques contenant au moins un colorant azoïque cationique comprenant deux groupes hétérocycliques

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Publication number
EP3223789A1
EP3223789A1 EP15780859.3A EP15780859A EP3223789A1 EP 3223789 A1 EP3223789 A1 EP 3223789A1 EP 15780859 A EP15780859 A EP 15780859A EP 3223789 A1 EP3223789 A1 EP 3223789A1
Authority
EP
European Patent Office
Prior art keywords
phenyl
ium
salts
diazen
methyl
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.)
Withdrawn
Application number
EP15780859.3A
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German (de)
English (en)
Inventor
Antje Gebert-Schwarzwälder
Ralph Nemitz
Astrid Kroos
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
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Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP3223789A1 publication Critical patent/EP3223789A1/fr
Withdrawn legal-status Critical Current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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966—Triazines or their condensed derivatives
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • the present invention relates to color-changing agents of keratinic fibers, in particular human hair, containing (a) at least one cationic azo dye having two heterocyclic groups.
  • oxidation dyes For the dyeing of keratinic fibers, either direct dyes or oxidation dyes are generally used. Although intensive dyeings with good fastness properties can be obtained with oxidation dyes, the development of the color is generally carried out under the influence of oxidizing agents such. H2O2, which in some cases can result in damage to the fiber. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors may have a sensitizing effect on persons with sensitive skin. Direct dyes are applied under gentler conditions. Their disadvantage lies in the fact that the dyeings often have only insufficient fastness properties.
  • the expert uses substantive dyes of different classes of dyes.
  • the direct dyes known from the prior art include, for example, the class of nitro dyes, the anthraquinone dyes, the azo dyes, the triarylmethane dyes or the methine dyes. All of these classes of dyes should meet a specific requirement profile for use in the cosmetics sector. Thus, direct dyes should provide an intensive dyeing result and have the best possible fastness properties. Due to environmental influences, the color result obtained with substantive dyes should be influenced as little as possible, i. For example, the dyes should have good fastness to washing, lightfastness and rubfastness. Also, chemical influences that the keratinic fibers may be exposed to after the dyeing process (such as perms) should change the color result as little as possible.
  • the direct dyes should if possible also be compatible with the usual oxidizing agents used in bleaching processes (such as hydrogen peroxide and / or persulfates).
  • Cationic dyes are often characterized by a particularly high affinity for keratin fibers, which can be attributed to the interactions of the positive charges of the dyes with negatively charged structural components of the keratinic fibers. Therefore, it is often possible to achieve particularly intensive dyeings with cationic dyes.
  • Basic Orange 31 (alternative name: 2 - [(4-aminophenyl) azo] -1,3-dimethyl-1H-imidazolium chlorides, CAS No. 97404-02, which are well-known from the prior art are cationic azo dyes 9) and Basic Red 51 (alternative name: 2 - [((4-dimethylamino) phenyl) azo] -1,3-dimethyl-1H-imidazolium chloride, CAS No. 77061-58-6).
  • the object of the present application is therefore to provide colorants for keratinic fibers, in particular human hair, which have good performance properties in terms of color depth and fastness properties, in particular light fastness, rubfastness and wash fastness, as well as perspiration and cold wave fastness.
  • the direct dyes should have high stability to hydrogen peroxide and other oxidizing agents and not lose their positive fastness and dyeing properties.
  • as bright and intense colors as possible should be achieved.
  • the aforementioned dyes should also be particularly well compatible with the cationic azo dyes Basic Orange 31 and Basic Red 51.
  • a first object of the present invention is a means for color-changing keratinic fibers, in particular human hair, contained in a cosmetic carrier
  • Het 1 represents one of the structures (II), (I II), (IV), (V), (VI) or (VII),
  • R 1, R 2 independently of one another represent a hydrogen atom, a C 1 -C 6 -alkyl group
  • Halogen atom from the group chlorine, bromine, fluorine or iodine, for a Ci -Ce-
  • R 6 independently of one another are a C 1 -C 6 -alkyl group, a C 2 -C 6 -alkenyl group or a hydroxy-C 2 -C 6 -alkyl group,
  • R4, R5 independently represent a hydrogen atom, a Ci-Ce-alkyl group, a
  • Halogen atom from the group chlorine, bromine, fluorine or iodine, for a Ci -Ce-
  • Het 2 represents one of the structures (VI II), (IX), (X) (XI), (XII) or (XIII),
  • R 7 is a hydrogen atom or a C 1 -C 6 -alkyl group
  • Keratinic fibers, keratin-containing fibers or keratin fibers are understood to mean furs, wool, feathers and, in particular, human hair.
  • compositions according to the invention are primarily suitable for whitening keratin fibers, in principle there is nothing to prevent their use in other fields as well.
  • color change of keratin fibers encompasses any form of color change of the fibers, including in particular color changes encompassed by the terms tinting, bleaching, matting, oxidative dyeing, semi-permanent dyeing, permanent dyeing and temporary dyeing Coloring bleaching is understood to mean the simultaneous lightening and coloring of the keratinic fibers which can be achieved by the simultaneous use of oxidizing agent and dye in the staining modifying agent.
  • the agents according to the invention contain the substantive dyes of the formula (I) in a cosmetic vehicle.
  • This cosmetic carrier is preferably aqueous, alcoholic or aqueous-alcoholic.
  • such carriers are for example creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • a powdery or tablet-like formulation This is then mixed before use in an aqueous solvent or with organic solvents or with mixtures of water and organic solvents to obtain the application mixture.
  • an aqueous carrier contains at least 40% by weight, in particular at least 50% by weight, of water.
  • aqueous-alcoholic carriers are water-containing compositions containing from 3 to 70% by weight. a Ci -C4-alcohol, in particular ethanol or isopropanol to understand.
  • the compositions according to the invention may additionally contain other organic solvents, for example 4-methoxybutanol, ethyl diglycol, 1,2-propylene glycol, n-propanol, n-butanol, n-butylene glycol, glycerol, diethylene glycol monoethyl ether and diethylene glycol mono-n-butyl ether, contain. Preference is given to all water-soluble organic solvents.
  • Preferred agents according to the invention are characterized in that they additionally comprise a non-aqueous solvent, preferred agents according to the invention containing the solvent in a concentration of 0.1 to 30% by weight, preferably in a concentration of 1 to 20% by weight, very particularly preferably in a concentration of 2 to 10 wt .-%, each based on the agent.
  • the agents according to the invention contain at least one substantive dye of the formula (I).
  • R 1 to R 7 of the compounds of the formula (I) are described below by way of example:
  • Examples of a C 1 -C 6 -alkyl group are the groups methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl, n- Pentyl and n-hexyl.
  • Propyl, ethyl and methyl are preferred alkyl radicals.
  • Examples of a C2-C6 alkenyl group are vinyl, allyl, but-2-enyl, but-3-enyl and isobutenyl, preferred C2-C6 alkenyl radicals are vinyl and allyl.
  • Halogen atoms are selected from the group chlorine, bromine, fluorine and / or iodine, in which case chlorine and bromine are particularly preferred.
  • exemplary of a Ci-Ce alkoxy group, the methoxy, the ethoxy and the propoxy group can be mentioned.
  • a nitro group is a grouping -NO2 to understand.
  • Each substantive dye of the formula (I) has a cationic, heterocyclic end group Het 1.
  • Het 1 is an unsaturated heterocycle with a positive charge that is neutralized by the physiologically compatible counterion X-.
  • Het 1 represents a grouping from the group of formulas (II) to (VII)
  • Formula (II) represents a cationic thiazolium end group.
  • Formula (II I) represents a cationic imidazolium end group.
  • Formula (IV) represents a cationic, 1,2,4-triazolium end group.
  • Formula (V) represents a cationic 1, 3,4-thiadiazolium end group.
  • Formula (VI) represents a cationic 1, 2,4-thiadiazolium end group.
  • Formula (VII) represents a cationic pyrazolium end group.
  • the absorption spectrum of the dye and thus also the coloration of the dye can be influenced.
  • Het 1 stands for a heterocyclic end group of the formula (II).
  • Het 1 is selected from the heterocyclic end groups of the formulas (III) or (IV).
  • the agent (a) according to the invention contains at least one substantive dye of the general formula (I) in which
  • an agent according to the invention is characterized in that it contains (a) at least one substantive dye of the general formula (I) in which
  • Het1 represents one of the structures (II), (II I) or (IV)
  • the radicals R1 and R2 indicate the substituents on the phenyl ring of the substantive dye.
  • R 1 and R 2 independently of one another can be a hydrogen atom, a C 1 -C 6 -alkyl group, a halogen atom from the group consisting of chlorine, bromine, fluorine or iodine, a C 1 -C 6 -alkoxy group or a nitro group.
  • R 1 and R 2 independently of one another represent a hydrogen atom or a C 1 -C 6 -alkyl group, more preferably a hydrogen atom or a methyl group.
  • an agent according to the invention is characterized in that it contains (a) at least one substantive dye of the general formula (I) in which
  • R1 independently of one another represent a hydrogen atom or a C 1 -C 6 -alkyl group, preferably a hydrogen atom or a methyl group.
  • the heterocyclic group Het1 is selected from one of the structures of the formulas (I I) to (VII), these heterocyclic groups carrying the radicals R3, R4, R5 and / or R6.
  • the radicals R3 and R6 are each positioned on a nitrogen atom of the heterocycle and may independently of one another be a Ci-Ce-alkyl group, a C2-Ce-alkenyl group or a hydroxy-C2-Ce-alkyl group.
  • R4 and R5 are each located on a carbon atom of the heterocyclic end groups of the formulas (II) to (VII).
  • R4 and R5 independently of one another represent a hydrogen atom, a C 1 -C 6 -alkyl group, a halogen atom from the group consisting of chlorine, bromine, fluorine or iodine, a C 1 -C 6 -alkoxy group or a nitro group.
  • R 3 and R 6 independently of one another are a C 1 -C 6 -alkyl group, in particular a methyl group or an ethyl group.
  • an agent according to the invention is characterized in that it contains (a) at least one substantive dye of the general formula (I) in which
  • R3, R6 independently of one another are a C 1 -C 6 -alkyl group, preferably a methyl group or an ethyl group.
  • the dyes of the formula (I) according to the invention for the production of attractive and intense color shades are particularly suitable when R4 and R5 are independently a hydrogen atom or a Ci-Ce-alkyl group, in particular a hydrogen atom or a methyl group.
  • an agent according to the invention is characterized in that it contains (a) at least one substantive dye of the general formula (I) in which
  • R4, R5 independently of one another represent a hydrogen atom or a C 1 -C 6 -alkyl group, preferably a hydrogen atom or a methyl group.
  • composition according to the invention in a further particularly preferred embodiment is characterized in that it contains (a) at least one substantive dye of the general formula (I) in which
  • R 3 independently of one another are a C 1 -C 6 -alkyl group, preferably a methyl group or an ethyl group, and
  • R4, R5 independently of one another represent a hydrogen atom or a C 1 -C 6 -alkyl group, preferably a hydrogen atom or a methyl group.
  • the direct-acting dyes of the formula (I) according to the invention are characterized by the presence of a second heterocycle Het 2.
  • Het 2 is a saturated, uncharged heterocyclic system.
  • Het 2 represents one of the structures of formulas (VI II) to (XII I).
  • the structure of formula (IX) is a piperidinyl group linked via the N atom.
  • the structure of formula (X) is a pyrrolidinyl group linked via the N atom.
  • the structure of the formula (XI) is an azepine group linked via the N atom (alternative name: 1-azacycloheptyl group).
  • the structure of formula (XII) is a thiomorpholinyl group linked via the N atom.
  • the structure of formula (XIII) is a piperazinyl group linked via an N atom.
  • the Piperazinylendoli of formula (XIII) further carries the radical R7, which may be a hydrogen atom or a Ci-Ce-alkyl group.
  • R7 is a hydrogen atom or a methyl group.
  • a central object of the present invention was to find dyes with high stability to the usually employed in the bleaching of keratin fibers oxidizing agents (hydrogen peroxide + persulfates).
  • the finding of correspondingly stable dyes allows the simultaneous strong lightening and coloring of keratinic fibers.
  • the spatial orientation of this ring system may prevent the attack of the oxidant (i.e., the nucleophilic attack, e.g., a hydroxide anion HOO, is hindered by the steric orientation of the ring).
  • the oxidant i.e., the nucleophilic attack, e.g., a hydroxide anion HOO
  • heterocycle Het 2 stands for one of the structures (VIII), (IX) or (X).
  • an agent according to the invention is characterized in that it contains (a) at least one substantive dye of the general formula (I) in which
  • Het 2 represents one of the structures (VI II), (IX) or (X).
  • an agent according to the invention is also characterized in that it contains (a) at least one substantive dye of the general formula (I) in which
  • R7 represents a hydrogen atom or a methyl group.
  • the dyes of the formula (I) according to the invention are cationic azo dyes which are positively charged.
  • the positive charge is in each case neutralized by the anionic counterion X (of the structural units (II) to (VII)).
  • the cationic organic part is responsible for the coloring of the keratin fibers.
  • the counterion X serves only to preserve the electron neutrality, so that the exact nature of the counterions X does not play a significant role in achieving the desired color result. Since the dyes are used in cosmetic color change agents, the counterion must be physiologically compatible. Physiologically acceptable in this context means suitable for use in the cosmetic (i.e., for use on human hair and human skin).
  • the counterion X is a physiologically acceptable anion, which is preferably selected from the group chloride, bromide, iodide, methyl sulfate, methyl sulfonate, p-toluenesulfonate, acetate, hydrogen sulfate, Vz sulfate or Vz Tetrachlorozinkat.
  • Chloride is understood as meaning an anion Cl "
  • bromide is understood as meaning an anion Br
  • iodide is understood to mean an anion J-.”
  • Methylsulfate is understood to mean an anion H3COSO4.
  • an anion is "understood.
  • anion H3C is (CeH4) S03" H3CSO3 understood.
  • acetate is meant an anion H3CCOO-.
  • hydrogen sulfate is meant an anion HSO4 " .
  • Vz sulphate is understood to be one-half equivalent of the doubly negatively charged anion SO4 2 " .Vz tetrachlorozincate is understood to be half the equivalent of the doubly negatively charged anion ZnCU 2" .
  • an agent for color-changing keratinic fibers is characterized in that it comprises at least one compound of the general formula (I) which is selected from
  • the aforementioned compounds are cationic dyes wherein the organic cation is neutralized by the anion X-.
  • the anions X- are each a physiologically tolerable anion, preferably from the group consisting of chloride, bromide, iodide, methylsulfate, methylsulfonate, p-toluenesulfonate, acetate, hydrogensulfate, sulfate or tetrachlorozincate.
  • agents for dyeing keratinic fibers which contain at least one dye (a) of the formula (I) which is selected from the group consisting of
  • compositions according to the invention for Color change of keratinic fibers preferably contain the substantive dye or dyes of the formula (I) in a total amount of from 0.01 to 4.5% by weight, preferably from 0.05 to 2.8% by weight, more preferably from 0 , 1 to 2.2 w
  • an agent for dyeing keratinic fibers according to the invention is therefore characterized in that it contains, based on the total weight of the agent, one or more substantive dyes (a) of the formula (I) in a total amount of from 0.01 to 4 , 5 wt .-%, preferably from 0.05 to 2.8 wt .-%, more preferably from 0.1 to 2.2 wt .-% and particularly preferably from 0.2 to 1, 2 wt .-% contains.
  • the dyes of the general formula (I) can be prepared, for example, by the following method:
  • the educt 2-aminothiazole can be converted in concentrated sulfuric acid with nitrosyl sulfuric acid into the diazonium ion:
  • the 4-phenylmorpholine which can be used as starting material in the azo coupling reaction is commercially available, for example, from Acros or Aldrich.
  • the neutral dimer dye formed in the azo coupling reaction can be double quaternized with quaternizing agents.
  • the quaternization reaction is preferably in one polar aprotic solvents (such as DMSO, DMF etc.).
  • Suitable quaternizing agents are, for example, dimethyl sulfate, methyl bromide or p-toluenesulfonate.
  • the agents according to the invention additionally contain at least one surfactant. It has been found that very intense color results could be obtained in particular if the agents according to the invention additionally contained at least one anionic surfactant (b).
  • Surfactants are amphiphilic (bifunctional) compounds which consist of at least one hydrophobic and at least one hydrophilic moiety.
  • the hydrophobic moiety is preferably a hydrocarbon chain of 8-24 carbon atoms, which may be saturated or unsaturated, linear or branched. With particular preference, this alkyl chain is linear.
  • the hydrophilic moiety comprises a negatively charged hydrophilic moiety.
  • the negatively charged hydrophilic head group may be, for example, a carboxylic acid group bwz. the salt of a carboxylic acid group, a sulfonic acid group or the salt of the sulfonic acid group, a sulfuric acid ester group or the salt thereof, a phosphonic acid group or the salt of the phosphonic acid group, or a Phosphorklargration or the salt thereof.
  • the cosmetic agent according to the invention usually comprises an aqueous carrier.
  • the abovementioned hydrophilic head groups of the anionic surfactant- such as, for example, the carboxylic acid and the salts of the carboxylic acids-are in an equilibrium whose position is determined by the pH of the agent. If, for example, a fatty acid is used as the anionic surfactant, then a small proportion of the fatty acid is present in aqueous solution in the form of the protonated fatty acid, whereas the major part of the fatty acid is deprotonated in aqueous solution and converted in this way into the salt of the fatty acid. For this reason, the definition of an anionic surfactant also includes a surfactant with a - still protonated - acid group.
  • An anionic surfactant (b) for the purposes of the present invention contains no cationic groups, ie zwitterionic surfactants are not included in the definition of an anionic surfactant.
  • Anionic surfactants according to the invention are accordingly characterized by the presence of a water-solubilizing, anionic group such as. As a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 8 to 30 carbon atoms.
  • a water-solubilizing, anionic group such as.
  • a carboxylate, sulfate, sulfonate or phosphate group As a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 8 to 30 carbon atoms.
  • Polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be included.
  • anionic surfactants are alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and Dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionate
  • anionic surfactants according to the invention are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts having 2 to 4 C atoms in the alkanol group,
  • Sulfobernsteinklamono- and dialkyl esters having 8 to 24 carbon atoms in the alkyl group and sulfosuccinic monoalkylpolyoxyethylester having 8 to 24 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups.
  • Sulfosuccinic acid mono- and dialkyl esters can be prepared by reacting maleic anhydride with a fatty alcohol having 8-24 carbon atoms to form the maleic monoester of the fatty alcohol and further reacting with sodium sulfite to form the sulfosuccinic acid ester.
  • Particularly suitable sulfosuccinic acid esters are derived from fatty alcohol fractions containing 12-18 C Atoms off, as z. B. from coconut fatty acid or Kokosfett Maschinenmbaquiper are accessible by hydrogenation,
  • Alpha-sulfofatty acid methyl esters of fatty acids having 8 to 30 carbon atoms are alpha-sulfofatty acids having 8 to 30 carbon atoms.
  • Alkyl sulfates and alkyl polyglycol ether sulfates of formula R-0 (CH2 -CH20 -OS0 3 H, in which R is a preferably linear alkyl group having 8 to 30 carbon atoms and x is 0 or 1 to 12,
  • Hydroxysulfonates essentially corresponding to at least one of the following two formulas or mixtures thereof and salts thereof,
  • R 1 - 3M sulfated hydroxyalkylpolyethylene and / or hydroxyalkylene glycol ethers of the formula R 1 - 3M) -CHR 3 - (OCHR) n-OR 2 with R 1 , a linear alkyl radical having 1 to 24 C atoms, R 2 is a linear or branched, saturated alkyl radical with 1 to 24 C atoms, R 3 is hydrogen or a linear alkyl radical having 1 to 24 C atoms, R 4 is hydrogen or a methyl radical and M is hydrogen, ammonium, alkylammonium, alkanolammonium, in which the alkyl and alkanol radicals are each 1 having up to 4 carbon atoms, a metal atom selected from lithium, sodium, potassium, calcium or magnesium or and n is a number in the range of 0 are to 12, and further the total number of carbon atoms 2 contained in R 1 and R 3 to 44,
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols containing 8 to 22 carbon atoms, alkyl and / or alkenyl ether phosphates of the formula
  • R 1 is preferred for an aliphatic hydrocarbon radical having 8 to 30 carbon atoms
  • R 2 is hydrogen, a radical (CH 2 CH 2 0 or X, n for numbers from 1 to 10 and X is hydrogen, an alkali or alkaline earth metal or NR 3 R 4 R 5 R 6 , where R 3 to R 6 independently of one another represent hydrogen or a bis-hydrocarbon radical,
  • sulfated fatty acid alkylene glycol esters of the formula RCO AlkO in the RCO-- for a linear or branched, aliphatic, saturated and / or unsaturated acyl radical having 6 to 22 C atoms, Alk for CH 2 CH 2, CHCH 3 CH 2 and / or CH 2 CHCH 3, n for numbers from 0.5 to 5 and M for a metal such as alkali metal, in particular sodium, potassium, lithium, alkaline earth metal, in particular magnesium, calcium, zinc, or ammonium ion, such as + NR 3 R 4 R 5 R 6 , where R 3 to R 6 are independently hydrogen or a C1 to C4 - hydrocarbon radical,
  • R 8 CO is a linear or branched acyl radical having 6 to 22 carbon atoms
  • x, y and z are in total 0 or numbers of 1 to 30, preferably 2 to 10
  • X is an alkali or alkaline earth metal.
  • monoglyceride (ether) sulfates suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglyceride, oleic acid monoglyceride and tallow fatty acid monoglyceride and their ethylene oxide adducts with sulfur trioxide or chlorosulfonic acid in the form of their sodium salts.
  • monoglyceride sulfates are used, in which R 8 CO is a linear acyl radical having 8 to 18 carbon atoms,
  • Amide ether carboxylic acids R 1 -CO-NR 2 -CH 2 CH 2 -O- (CH 2 CH 2 O) n CH 2 COOM, wherein R 1 is a straight-chain or branched alkyl or alkenyl radical having a number of carbon atoms in the chain of 2 to 30, n is an integer from 1 to 20 and R 2 is hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl or iso-butyl and M is hydrogen or a metal such as alkali metal, especially sodium , Potassium, lithium, alkaline earth metal, in particular magnesium, calcium, zinc, or an ammonium ion, such as + NR 3 R 4 R 5 R 6 , where R 3 to R 6 are each independently hydrogen or a C 1 to C 4 hydrocarbon radical.
  • Such products are obtainable, for example, by the company Chem Y under the product name Akypo ®, and acyl glutamates of the formula XOOC-CH2CH2CH (C (NH) OR) -COOX, in which RCO is a linear or branched acyl group containing 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds and X is hydrogen, an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
  • R 1 -CO-NR 2 -CH 2 CH 2 -O- (CH 2 CH 2 O) 2 COOM with R 1 as a straight-chain or branched alkyl or alkenyl radical having a number of carbon atoms in the chain of 2 to 30, n is a an integer from 1 to 20 and R 2 is hydrogen, a methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl or iso-butyl radical and M is hydrogen or a metal such as alkali metal, in particular sodium, potassium, lithium, alkaline earth metal, in particular magnesium, calcium, zinc, or an ammonium ion, such as + NR 3 R 4 R 5 R 6 , where R 3 to R 6 independently of one another represent hydrogen or a C 1 to C 4 hydrocarbon radical.
  • Such products are obtainable, for example by the company Chem Y under the product name Akypo ®, and
  • an agent according to the invention is therefore characterized in that it contains (b) at least one anionic surfactant which is selected from the linear and branched fatty acids having 8 to 30 C atoms,
  • R is a linear alkyl group having 8 to 30 carbon atoms
  • x is an integer from 0 to 16
  • M is hydrogen or a metal such as alkali metal, in particular sodium, potassium, lithium, alkaline earth metal, in particular magnesium, calcium, zinc, or an ammonium ion (NH 4 + ),
  • R 1 is a C 2 -C 30 -alkyl group
  • y is an integer from 1 to 20,
  • R 2 is hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl or iso-butyl, and
  • M represents hydrogen or a metal such as an alkali metal, in particular sodium, potassium, lithium, an alkaline earth metal, in particular Vz magnesium, Vz calcium, Vz zinc, or an ammonium ion (NH4 + ).
  • an alkali metal in particular sodium, potassium, lithium, an alkaline earth metal, in particular Vz magnesium, Vz calcium, Vz zinc, or an ammonium ion (NH4 + ).
  • a particularly good paint absorption capability could be observed if at least one ether carboxylic acid of the formula R-O- (CH 2 -CH 2 O) -CH 2 -COOH or its salt was used as the anionic surfactant (b).
  • the use of - optionally ethoxylated - ether carboxylic acids is therefore explicitly very particularly preferred.
  • an agent according to the invention is therefore characterized in that at least one anionic surfactant (b) contains from the group of the ether carboxylic acids of the formula (B1)
  • R is a linear alkyl group having 8 to 30 carbon atoms
  • x is an integer from 0 to 16
  • M represents hydrogen or a metal such as an alkali metal, in particular sodium, potassium, lithium, an alkaline earth metal, in particular Vz magnesium, Vz calcium, Vz zinc, or an ammonium ion (NH4 + ).
  • x is particularly preferably the numbers 5, 6 or 7.
  • an agent according to the invention is therefore characterized in that the anionic surfactant (b) comprises at least one ether carboxylic acid of the formula (B1)
  • R is a linear alkyl group having 8 to 30 carbon atoms
  • x is the integer from 5 to 1, in particular the numbers 5, 6 or 7,
  • M is hydrogen or a metal such as an alkali metal, especially sodium, potassium, lithium
  • Alkaline earth metal in particular Vz magnesium, Vz calcium, Vz zinc, or an ammonium ion (NH4 + ) stands.
  • the very particularly preferred anionic surfactants of the formula (B1) are obtainable, for example, under the trade name
  • the agents according to the invention for dyeing keratinic fibers preferably contain one or more anionic surfactants (b) in a total amount of from 0.05 to 4.5% by weight, preferably from 0.1 to 2.1% by weight, more preferably from 0.15 to 1, 8 wt .-% and most preferably from 0.2 to 0.9 wt .-%.
  • the data in% by weight are based on the total amount of all anionic surfactants (b) which are related to the total amount of the colorant.
  • an agent for dyeing keratinic fibers according to the invention is therefore characterized in that it contains, based on the total weight of the composition, one or more anionic surfactants (b) in a total amount of 0.05 to 9.5 wt. %, preferably from 0.1 to 3.1 wt .-%, more preferably from 0.15 to 2.5 wt .-% and most preferably from 0.2 to 0.9 wt .-%.
  • the paint lift can be improved by using at least one anionic surfactant.
  • the use of at least one - optionally ethoxylated - ether carboxylic acid and / or its salt, as described in formula (B1), has proved to be particularly advantageous in this context.
  • the keratin fibers could be dyed in especially intense shades, especially when the ether carboxylic acid (s) and / or its salts were included as the main anionic surfactant in the composition of the invention.
  • the dyeing results were particularly intense when the inventive compositions contained one or more ether carboxylic acids of the formula (B1), and, moreover, if all other anionic surfactants used were only present in minor amounts.
  • the use of the ether carboxylic acid (s) of the formula (B1) as the main surfactant can be quantified by specifying a weight ratio which contains the total amount of anionic surfactants of the formula (B1) present in the total amount of all anionic surfactants (b) present in the composition Relation sets.
  • an agent for dyeing keratinic fibers according to the invention is therefore characterized in that the weight ratio of all the anionic surfactants of the formula (B1) present in the composition to the total amount of the anionic surfactants present in the composition is 0.5, is preferably 0.6, more preferably 0.75, and most preferably 0.9,
  • anionic surfactants of the formula (B1) are the following surfactants
  • R is a linear alkyl group having 8 to 30 C atoms
  • M is hydrogen or a metal such as alkali metal, in particular sodium, potassium, lithium, alkaline earth metal, in particular magnesium, calcium, zinc, or an ammonium ion (NH4 + ).
  • An agent for coloring keratinic fibers contains:
  • An agent for coloring keratinic fibers contains:
  • compositions according to the invention may also contain one or more cationic surfactants.
  • Cationic surfactants are understood to mean surfactants, ie surface-active compounds, each having one or more positive charges. Cationic surfactants contain only positive charges. Usually, these surfactants are composed of a hydrophobic part and a hydrophilic head group, wherein the hydrophobic part usually consists of a hydrocarbon skeleton (eg consisting of one or two linear or branched alkyl chains), and the positive charge (s) are located in the hydrophilic head group. Cationic surfactants adsorb at interfaces and aggregate in aqueous solution above the critical micelle concentration to positively charged micelles.
  • Quaternary ammonium compounds which can carry as hydrophobic radicals one or two alkyl chains with a chain length of 8 to 28 carbon atoms
  • quaternary phosphonium salts substituted with one or more alkyl chains having a chain length of 8 to 28 C atoms or
  • the cationic charge may also be in the form of an onium structure as part of a heterocyclic ring (e.g., an imidazolium ring or a pyridinium ring).
  • the cationic surfactant may also contain other uncharged functional groups, such as is the case with esterquats.
  • Suitable cationic surfactants of this type are, for example, physiologically tolerable salts of N, N, N-trimethyl-1-hexadecanaminium, in particular N, N, N-trimethyl-1-hexadecanaminium chloride, which is also sold under the trade name Dehyquart A-CA.
  • Another suitable cationic surfactant is a physiologically acceptable salt of dimethyl distearyldimethylammonium, more preferably dimethyl distearylammonium chloride.
  • cationic surfactants can be selected from the group of cationic imidazolium compounds.
  • composition according to the invention may contain the cationic surfactant (s) in a total amount of from 0.1 to 4.8% by weight, preferably from 0.2 to 2.4% by weight, more preferably from 0.3 to 1.8 Wt .-% - based on the total weight of the composition - included.
  • Agents suitable according to the invention can furthermore be characterized in that they additionally comprise at least one zwitterionic surfactant.
  • Suitable zwitterionic surfactants are betaines, N-alkyl-N, N-dimethylammonium glycinates, N-acylaminopropyl-N, N-dimethylammonium glycinates, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines.
  • a preferred zwitterionic surfactant is known by the INCI name Cocamidopropyl Betaine.
  • Agents suitable according to the invention are characterized in that the agent additionally contains at least one amphoteric surfactant.
  • Preferred 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.
  • Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 -C 18 -acylsarcosine.
  • the agents contain other, nonionic surfactants.
  • Preferred nonionic surfactants are alkylpolyglycosides and alkylene oxide addition products to fatty alcohols and fatty acids with in each case 2 to 30 mol of ethylene oxide per mole of fatty alcohol or fatty acid. Preparations having excellent properties are also obtained if they contain fatty acid esters of ethoxylated glycerol as nonionic surfactants.
  • the nonionic, zwitterionic or amphoteric surfactants are used in proportions of from 0.1 to 45% by weight, preferably from 1 to 30% by weight and very particularly preferably from 1 to 15% by weight, based on the total amount of ready-to-use agents.
  • the agents according to the invention additionally comprise at least one further substantive dye in addition to the compound of the formula (I).
  • the achievable range of nuances can be extended, and the dyeing properties can be further improved.
  • Direct dyes can be subdivided into anionic, cationic and nonionic substantive dyes.
  • the substantive dyes are preferably selected from the cationic substantive dyes, since these are well compatible with the dyes of general formula (I).
  • an agent according to the invention is characterized in that it additionally contains at least one further cationic substantive dye which is different from the dyes of the formula (I).
  • One or more dyes from the group Basic Yellow 87, Basic Orange 31, Basic Red 51, Basic Violet 2 and Cationic Blue 347 have proven to be particularly compatible.
  • the dyes of the formula (I) with the cationic azo dyes Basic Orange 31 and Basic Red 51 are particularly well compatible. By combining a dye of the formula (I) with Basic Orange 31 and / or Basice Red 51, nuances can be produced in the entire color spectrum-apart from purely yellow shades.
  • an agent according to the invention is characterized in that it additionally contains Basic Orange 31 and / or Basic Red 51.
  • composition according to the invention may additionally contain at least one nonionic substantive dye.
  • This can be selected from the group 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 7, HC Red 10 , HC Red 1, HC Red 13, HC Red BN, HC Blue 2, HC Blue 1 1, HC Blue 12, Disperse Blue 3, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, 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-amin
  • anionic direct dyes may also be present, which are available under the international names or trade names 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, Acid Black 52, Bromophenol Blue and Tetrabromophenol Blue are known.
  • the agents according to the invention can furthermore also be used together with oxidation dyes.
  • Such oxidation colorants additionally contain at least one oxidation dye precursor, preferably at least one developer-type oxidation dye precursor and at least one coupler-type oxidation dye precursor.
  • Particularly suitable developer-type oxidation dye precursors are selected from at least one compound from the group formed from p-phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, 2- (1,2-dihydroxyethyl ) -p-phenylenediamine, N, N-bis- (2-hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p- phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1 H -imidazol-1-yl) propyl] amine, N, N'-bis (2-hydroxyethyl) -N, N ' bis (4-aminophenyl) -1, 3-diamino-propan-2-ol, bis (2-hydroxy-5-aminophenyl) -methane, 1, 3-bis (2,5-diaminophenoxy) propane 2-
  • coupler-type oxidation dye precursors are selected from the group formed from 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 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, 2 - ( ⁇ 3 - [(2-hydroxyethyl) amino] -4-methoxy-5-methylphenyl ⁇ amino) ethanol,
  • the additional substantive dyes, developer components and coupler components are preferably used in a proportion of 0.0001 to 5.0 wt .-%, preferably 0.001 to 3.5 wt .-%, each based on the ready-to-use agent.
  • developer components and coupler components are generally used in approximately molar amounts to each other.
  • a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components in a molar ratio of 1: 0.5 to 1: 3, in particular 1: 1 to 1: 2 , can stand.
  • the agents according to the invention additionally comprise an oxidizing agent, preferably hydrogen peroxide and / or one of its solid addition products of organic or inorganic compounds.
  • an oxidizing agent preferably hydrogen peroxide and / or one of its solid addition products of organic or inorganic compounds.
  • hydrogen peroxide itself is used as the aqueous solution.
  • concentration of a hydrogen peroxide solution in the composition according to the invention is determined on the one hand by the legal requirements and on the other hand by the desired effect; preferably 6 to 12 wt .-% solutions are used in water.
  • wt .-% based on the total weight of the ready-to-use agent, 0.5 to 20 wt .-%, preferably 1 to 12.5 wt .-%, particularly preferably 2.5 to 10 Wt .-% and in particular 3 to 6 wt .-% hydrogen peroxide, each based on the total weight of the composition.
  • an agent according to the invention is characterized in that, based on the total weight of the composition, it is 0.5 to 12.5% by weight, preferably 2.5 to 10% by weight and in particular 3 to 6 Wt .-% hydrogen peroxide.
  • the composition may further contain at least one peroxo salt.
  • Suitable peroxo salts are inorganic peroxo compounds, preferably selected from the group formed from ammonium peroxodisulfate, alkali metal peroxodisulfates, ammonium peroxomonosulfate, alkali metal peroxomonosulfates, alkali metal peroxodiphosphates and alkaline earth metal peroxides.
  • peroxodisulfates in particular ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate.
  • an agent according to the invention is characterized in that it additionally contains at least one persulfate from the group consisting of ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate.
  • the persulfates are each in an amount of 0.5 to 20 wt .-%, preferably 1 to 12.5 wt .-%, particularly preferably 2.5 to 10 wt .-% and in particular 3 to 6 wt .-%, based on the total weight of the ready-to-use agent, contained in the agent according to the invention.
  • an agent according to the invention is characterized in that it contains at least one persulfate from the group consisting of ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate.
  • Ammonium peroxodisulphate is a compound of the formula ( ⁇ ⁇ ) which is a compound of the formula K2S2O8 which is a compound of the formula K2S2O8
  • Sodium peroxodisulphate is a compound of the formula Formula Na2S20s.
  • an agent according to the invention is characterized in that it contains, based on the total weight of the agent, one or more persulfates from the group consisting of ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate in a total amount of 0.5 to 20% by weight, preferably from 1, 0 to 12.5 wt .-%, more preferably from 2.5 to 10 wt .-% and particularly preferably from 3.0 to 6.0 wt .-%.
  • the direct-acting dyes of the general formula (I) according to the invention have themselves proved to be particularly stable to certain mixtures of ammonium peroxodisulfate, potassium peroxodisulfate and sodium peroxodisulfate.
  • an agent according to the invention is characterized in that it contains, based on the total weight of the agent,
  • the dyeing and / or matting agent may contain further bleaching power boosters to enhance the bleaching effect, such as, for example, tetraacetylethylenediamine (TAED), 1,5-diacetyl-2,4-dioxo-hexahydro-1,3,5-triazine (DADHT), Tetraacetylglycoluril (TAGU), N-nonanoylsuccinimide (NOSI), n-nonanoyl or isononanoyloxybenzenesulfonate (n- or i-NOBS), phthalic anhydride, triacetin, ethylene glycol diacetate and 2,5-diacetoxy-2,5-dihydrofuran and carbonate salts or bicarbonate salts in particular ammonium bicarbonate, ammonium carbonate, sodium bicarbonate, disodium carbonate, potassium bicarbonate, dipotassium carbonate and calcium carbonate, and nitrogen-containing, heterocyclic bleach booster
  • At least one SiC> 2 compound such as silicic acid or silicates, in particular water glasses, may additionally be added to the composition according to the invention.
  • the SiC> 2 compounds may be preferred according to the invention, in amounts of 0.05 wt .-% to 15 wt .-%, particularly preferably in amounts of 0.15 wt .-% to 10 wt .-% and very particularly preferably in amounts of from 0.2% by weight to 5% by weight, based in each case on the anhydrous composition according to the invention.
  • the colorants may further contain additional active ingredients, auxiliaries and additives in order to improve the dyeing performance and to adjust further desired properties of the agents.
  • the colorants are provided as a liquid preparation and the agents therefore optionally additionally added a further surfactant, said surfactants depending on the field of application as surfactants or as emulsifiers: They are preferably selected from anionic, zwitterionic, amphoteric and nonionic surfactants and emulsifiers ,
  • the colorants of the invention may contain other auxiliaries and additives.
  • the agent contains at least one thickener.
  • these thickeners there are no fundamental restrictions. Both organic and purely inorganic thickening agents can be used.
  • Suitable thickeners are anionic synthetic polymers
  • guar gums such as nonionic guar gums, scleroglucan gums or xanthan gums, gum arabic, ghatti gum, karaya gum, gum tragacanth, carrageenan gum, agar, locust bean gum, pectins, alginates, starch fractions and derivatives such as amylose, Amylopectin and dextrins, as well as cellulose derivatives such as methylcellulose, carboxyalkylcelluloses and hydroxyalkylcelluloses;
  • nonionic, fully synthetic polymers such as polyvinyl alcohol or polyvinylpyrrolidinone; as well as inorganic thickening agents, in particular phyllosilicates such as, for example, bentonite, especially smectites, such as montmorillonite or hectorite.
  • the pH of the ready-to-use agent is between 7 and 11, in particular between 8 and 10.5.
  • the pH values are pH values which were measured at a temperature of 22 ° C.
  • the alkalizing agents which can be used in accordance with the invention for adjusting the preferred pH can be selected from the group consisting of ammonia, alkanolamines, basic amino acids and inorganic alkalizing agents such as (earth) alkali metal hydroxides, (earth) alkali metal metasilicates, (alkaline) alkaline metal phosphates and (Alkaline) alkali metal hydrogen phosphates.
  • Preferred inorganic alkalizing agents are magnesium carbonate, sodium hydroxide, potassium hydroxide, sodium silicate and sodium metasilicate.
  • Organic alkalizing agents which can be used according to the invention are preferably selected from monoethanolamine, 2-amino-2-methylpropanol and triethanolamine.
  • the basic amino acids which can be used as alkalizing agents according to the invention are preferably selected from the group formed from arginine, lysine, ornithine and histidine, more preferably arginine.
  • further preferred agents according to the invention are characterized in that they additionally contain an organic alkalizing agent.
  • An embodiment of the first subject of the invention is characterized in that the agent additionally contains at least one alkalizing agent which is selected from the group consisting of ammonia, alkanolamines and basic amino acids, in particular ammonia, monoethanolamine and arginine or its compatible salts.
  • the colorants in particular if they additionally contain hydrogen peroxide, contain at least one stabilizer or complexing agent.
  • stabilizers are phenacetin, alkali benzoates (sodium benzoate) and salicylic acid.
  • all complexing agents of the prior art can be used.
  • preferred Complexing agents are nitrogen-containing polycarboxylic acids, in particular EDTA and EDDS, and phosphonates, in particular 1-hydroxyethane-1, 1-diphosphonate (HEDP) and / or ethylenediaminetetramethylenephosphonate (EDTMP) and / or diethylenetriaminepentamethylenephosphonate (DTPMP) or their sodium salts.
  • the agents according to the invention may contain other active ingredients, auxiliaries and additives, for example nonionic polymers such as, for example, vinylpyrrolidinone / vinyl acrylate copolymers, polyvinylpyrrolidinone, vinylpyrrolidinone / vinyl acetate copolymers, polyethylene glycols and polysiloxanes; additional silicones, such as volatile or nonvolatile, straight-chain, branched or cyclic, crosslinked or uncrosslinked 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 copo
  • the choice of these other substances will be made by those skilled in the art according to the desired properties of the agents. With regard to further optional components and the amounts of these components used, reference is expressly made to the relevant manuals known to the person skilled in the art.
  • the additional active ingredients and auxiliaries are preferably used in the agents according to the invention in amounts of from 0.0001 to 25% by weight, in particular from 0.0005 to 15% by weight, based on the total weight of the application mixture.
  • the means of the first subject of the invention can be used in processes for changing the color of keratinic fibers, as in dyeing processes, but in particular also in processes for the simultaneous bleaching and dyeing of human hair.
  • the agents according to the invention can be formulated as single-component agents or as multicomponent agents, such as two-component agents or three-component agents, and used accordingly. Separation into multicomponent systems is particularly suitable where incompatibilities of the ingredients are to be expected or feared; the agent to be used in such systems is manufactured by the consumer just prior to use by mixing the component.
  • the agent according to the invention for the color change of keratinic fibers is always understood to mean the ready-to-use agent.
  • the agent according to the invention is made available to the user in the form of a one-component agent, then the ready-to-use agent need not first be prepared, but can be taken directly from the container in which it was made up and applied to the keratinic fibers.
  • Bleaching agents are usually two-component products in which an oxidizing agent-containing component (A1) shortly before application with an (alkalizing) agent
  • the agent according to the invention is the ready-to-use agent which was prepared shortly before use by mixing (A1) and (A2).
  • Alkalizing agent are made up.
  • the ready-to-use agent is prepared by mixing three components shortly before application to the human hair
  • the component (A1) at least one substantive dye of the general formula (I) and at least one alkalizing agent
  • Component (A2) contains at least one first oxidizing agent (for example hydrogen peroxide) and
  • - Component (A3) contains at least one second oxidizing agent (eg one or more peroxodisulfate salts).
  • the heat supply can be done by an external heat source, such as warm air of a hot air blower, as well as, especially in a hair lightening on the living subjects, by the body temperature of the subject. In the latter case, the treated batch is usually covered with a hood.
  • An exposure phase at room temperature is also according to the invention. In particular, the temperature during the exposure time between 20 ° C and 40 ° C, in particular between 25 ° C and 38 ° C.
  • the remaining dyeing preparation is rinsed with water or a cleaning agent from the hair.
  • a cleaning agent can be used in particular commercial shampoo, in particular then can be dispensed with the detergent and the rinsing can be done with water when the brightening agent has a strong surfactant-containing carrier.
  • Direct adduct 1 3-methyl-2- ⁇ 2- [4- (morpholin-4-yl) phenyl] diazene-1-yl ⁇ -1,3-thiazol-3-ium methylsulfate
  • the direct dyes DZ1 and DZ2 were each pre-dissolved in a little water and mixed with the remaining formulation ingredients.
  • Each of the color creams E and V1 was mixed in a weight ratio of 1: 1: 1 with the developer emulsion and with the bleaching powder.
  • Each 1, 8 g of the dyeing cream were applied to an approximately 6 cm long strand of human hair (Kerling Euronaturhaar, 80% gray) and left there for 30 minutes at 30 ° C. After completion of the exposure time, the hair was rinsed, washed with a conventional shampoo and then dried. After drying, the color and intensity of the streaks were visually evaluated under the daylight lamp.
  • Cetearyl Alcohol 1, 0 1, 0 (C16 / C18-fatty alcohol)
  • Cocoamidopropyl betaine (zwitterionic surfactant) 1, 0 -
  • the first five components were melted together. This melt was emulsified with hot water, then the dye dissolved in propylene glycol was added and the ammonium sulfate solution added. The indicated pH was adjusted with ammonia, then made up to 100 g with water.
  • Each 1, 8 g of the dyeing cream were applied to an approximately 6 cm long strand of human hair (Kerling Euronaturhaar, 80% gray) and left there for 30 minutes at 30 ° C. After completion of the exposure time, the hair was rinsed, washed with a conventional shampoo and then dried. After drying, the color and intensity of the streaks were visually evaluated under the daylight lamp.

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Abstract

L'invention concerne des agents de coloration de fibres kératiniques, notamment de cheveux humains, contenant dans un excipient cosmétique : (a) au moins un colorant direct de formule (I) dans laquelle Het 1 représente un hétérocycle cationique insaturé et Het 2 représente un hétérocycle non chargé saturé.
EP15780859.3A 2014-11-25 2015-10-14 Agents de coloration de fibres kératiniques contenant au moins un colorant azoïque cationique comprenant deux groupes hétérocycliques Withdrawn EP3223789A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102014223934.6A DE102014223934A1 (de) 2014-11-25 2014-11-25 Mittel zur Farbveränderung von keratinischen Fasern, enthaltend mindestens einen kationischen Azofarbstoff mit zwei heterozyklischen Gruppen
PCT/EP2015/073778 WO2016083014A1 (fr) 2014-11-25 2015-10-14 Agents de coloration de fibres kératiniques contenant au moins un colorant azoïque cationique comprenant deux groupes hétérocycliques

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EP3223789A1 true EP3223789A1 (fr) 2017-10-04

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US10034823B2 (en) * 2016-09-16 2018-07-31 Noxell Corporation Method of coloring hair with washfast blue imidazolium direct dye compounds
EP3512488B1 (fr) * 2016-09-13 2023-12-06 Wella Operations US, LLC Compositions de coloration capillaire comprenant des imidazoliums stables bleu-violet à bleu

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FR2757388B1 (fr) * 1996-12-23 1999-11-12 Oreal Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
FR2780881B1 (fr) * 1998-07-09 2001-08-10 Oreal Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un polymere epaississant
FR2822697B1 (fr) * 2001-04-02 2003-07-25 Oreal Nouvelle composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant azoique cationique particulier
FR2822694B1 (fr) * 2001-04-02 2005-02-04 Oreal Nouvelle composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant azoique cationique particulier
DE102005003821A1 (de) * 2005-01-27 2006-08-10 Wella Ag Mittel zur Färbung von Keratinfasern
DE102007018380A1 (de) * 2007-04-17 2008-10-30 Henkel Ag & Co. Kgaa Kationische Direktzieher und Mittel zum Färben von keratinhaltigen Fasern

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