EP2640351A2 - Utilisation de dérivés d'acide ascorbique pour teinter des fibres kératiniques - Google Patents

Utilisation de dérivés d'acide ascorbique pour teinter des fibres kératiniques

Info

Publication number
EP2640351A2
EP2640351A2 EP11773197.6A EP11773197A EP2640351A2 EP 2640351 A2 EP2640351 A2 EP 2640351A2 EP 11773197 A EP11773197 A EP 11773197A EP 2640351 A2 EP2640351 A2 EP 2640351A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
formula
atoms
straight
chain
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Withdrawn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
EP11773197.6A
Other languages
German (de)
English (en)
Inventor
Thomas Rudolph
Michaela Oberle
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.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP2640351A2 publication Critical patent/EP2640351A2/fr
Withdrawn legal-status Critical Current

Links

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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/32—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using oxidation dyes
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • 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
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the invention relates to the use of specific ascorbic acid derivatives for dyeing keratin-containing fibers or as substantive dyes for producing an agent for dyeing keratin-containing fibers and to processes for dyeing keratin-containing fibers, in particular for dyeing human hair.
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • Development component (oxidation base, developer) using oxidizing agents, e.g. Hydrogen peroxide, reacted to or partially in the keratin fiber to dye.
  • oxidizing agents e.g. Hydrogen peroxide
  • alkaline and oxidative conditions usually prevail at least during the dyeing process.
  • the oxidative environment is necessary so that the development component can be oxidized and in one
  • Coupling reaction with the coupling component can react at least to a precursor of a dye.
  • the alkaline environment serves on the one hand to develop the oxidative effect of e.g. Hydrogen peroxide and the other the opening of the fiber structure, so that the
  • Coupling component and / or the developing component and / or resulting dyes or their precursors can penetrate deeper into the fiber.
  • Both components preferably contain unsubstituted or substituted hydroxy or amine groups, preferably in the ortho and para positions in the development component and in the meta position in the case of
  • Coupling component In the formation of such a dye from the coupling component and the development component can also take place a binding of the dye to the fiber.
  • Hydrogen peroxide may in some cases damage the fiber. Furthermore, some can
  • Oxidation dye precursors sometimes have a sensitizing effect in persons with sensitive skin.
  • Direct dyes are applied under gentler conditions, but their disadvantage lies in the fact that the dyes often have only insufficient fastness properties.
  • Fastness properties are, for example, lightfastness, friction, perspiration and washfastness.
  • Keratin braven fibers which have a good connectivity of the Have dye molecules to the fiber, so that can be dyed more durable, at the same time have good fastness properties and achieve intense colorations.
  • the substantive dyes should have sufficient stability to hydrogen peroxide or should not lose their positive fastness and dyeing properties.
  • the ascorbic acid derivatives of the formula I or II, as described below are very suitable as substantive dyes for the dyeing of keratin-containing fibers.
  • the color effects are characterized by the fact that the color effect is resistant to washing and color-stable and produces a high gloss.
  • the achievable color values can produce an intensified blue coordinate and thus generate a modern, cool color impression.
  • Detergents such as a hair shampoo, can occur.
  • Hair dyeing additionally stabilized dye molecules to stabilize.
  • dye molecules to stabilize.
  • light-sensitive and oxidation-sensitive substantive dye molecules can be stabilized.
  • Methods for stabilization include e.g. both the pretreatment of the hair with ascorbic acid derivatives of the formula I or II before the actual dyeing procedure, as well as a
  • An object of the invention is therefore the use of compounds of formula I or II
  • R 1 or R 2 are each independently of one another hydroxy, -O-alkyl, -OC (O) -alkyl, -OPO 3 M or O-glycosyl,
  • Alkyl is a straight-chain or branched alkyl group having 1 to 10 C atoms
  • M alkali or alkaline earth metal cation or H means
  • R 3 or R 4 are each independently hydroxy or the formula
  • R 5 to R 9 are each independently H, -OH, straight-chain or branched alkoxy group having 1 to 20 C atoms, fluorinated straight-chain or branched alkoxy group having 1 to 20 C atoms, -A, -NH 2 , -NHA, -NA 2 , -NH- (CH 2 -CH 2 -O) n -H, -N [(CH 2 -CH 2 -O) n -H] 2 , - [NHA 2 ] X, - [NA 3 ] X, -S0 3 H, - [S0 3 ] X, 2H-benzotriazol-2-yl or -OC (0) -alkyl,
  • A is a straight-chain or branched alkyl group having 1 to 20 C atoms and
  • X is the counterion to the cations [NHA 2 ] + and [NA 3 ] + or the anion [S0 3 ] " , with the proviso that at least one of R 3 or R 4 of the formula
  • Another object of the invention is the use of
  • R 1 or R 2 are each independently of one another hydroxy, -O-alkyl, -OC (O) -alkyl, -OPO 3 M or O-glycosyl,
  • Alkyl is a straight-chain or branched alkyl group having 1 to 10 C atoms
  • M alkali or alkaline earth metal cation or H means
  • R 3 or R 4 are each independently hydroxy or the formula
  • R 5 to R 9 are each independently of one another H, -OH, straight-chain or branched alkoxy group having 1 to 20 C atoms, fluorinated straight-chain or branched alkoxy group having 1 to 20 C atoms, -A, -NH 2 , -NHA, -NA 2 , -NH- (CH 2 -CH 2 -O) n -H, -N [(CH 2 -CH 2 -O) n -H] 2 , - [NHA 2 ] X, - [NA 3 ] X, -SO 3 H, - [SO 3 ] X, 2H-benzotriazol-2-yl or -OC (O) -alkyl,
  • A is a straight-chain or branched alkyl group having 1 to 20 C atoms and
  • X is the counterion to the cations [NHA 2] + and [ ⁇ 3 ⁇ or the anion [SO 3] ",
  • Keratin-containing fibers are preferably human hair, wool, furs or feathers.
  • the compounds of the invention are in principle but also for dyeing other natural fibers, such as cotton, jute, sisal, linen or silk, or
  • Dyeing modified natural fibers such as regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose.
  • the keratin-containing fiber is human hair.
  • dieing of keratin-containing fibers used according to the invention encompasses any form of color change of the fibers, including in particular the color changes encompassed by the terms tinting, bleaching, oxidative dyeing, semi-permanent dyeing, permanent dyeing and temporary dyeing have a lighter color result in comparison to the starting color, such as, for example, bleaching, the term “dyeing of keratin-containing fibers" is preferred to mean
  • Tinting or a temporary, semi-permanent or permanent coloring understood.
  • the compounds of the formula I are, for example, from
  • Compounds can be used for product protection of sensitive components in cosmetic preparations, for example of dyes or dye components in corresponding
  • the compounds of the formula I are able to protect dyed hair from a color change.
  • dehydroascorbic acid derivatives are an oxidized form of the ascorbic acid derivatives of the formula I.
  • ascorbic acid for example, the following reaction, i. in the
  • the dehydroascorbic acid can be reduced back to ascorbic acid.
  • the corresponding statements in this regard also apply to the compounds of formula II.
  • Dehydroascorbic acid applies to the following designations as shown in the above Rekationsschema.
  • FR2939035 describes ascorbic acid acetals and their use for dyeing hair.
  • Produce color effects for example, as a coupling component for dyeing the keratin fibers with oxidation dyes are suitable.
  • the compounds of the formula I or II, and the compounds of the formula I or II indicated below as being preferred are suitable for penetrating through the hair cuticle into the hair cake, resulting in complete and lasting hair dyeing over the hair entire hair is achievable.
  • the compounds of the formula I or II and the compounds of the formula I or II indicated below as preferred improve hair moisture by excellent hydration of the hair keratin. With the hair moisture thus improving the hair structure properties, especially the hair elasticity.
  • Compounds of the formula I or II are outstandingly suitable for distributing themselves homogeneously in or on keratin-containing fibers or skin, in particular on human hair, and thus to form continuous coatings.
  • a very pronounced homogeneous antioxidative potential on the fiber or the Produce skin which is significantly improved compared to ascorbic acid.
  • alkyl denotes a straight-chain or branched alkyl group having 1 to 10 C atoms, for example having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 C atoms, for example methyl, ethyl, isopropyl , n-propyl, isobutyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, ethylhexyl, n-nonyl or n-decyl.
  • Suitable alkoxy radicals for R 1 or R 2 are those whose alkyl group contains 1 to 10 C atoms, preferably 1 to 6 C atoms, particularly preferably 1 to 4 C atoms.
  • Examples of particularly preferred alkoxy groups are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy or tert-butoxy.
  • the group -OPO 3 M is preferably the -OPO 3 H group, but it is also possible to use salts of the formula I where M in formula I is an alkali metal cation, for example Na or K, or an alkaline earth metal cation, for example of Mg or Ca, corresponds.
  • a carbohydrate in position 2 or 3 of the basic structure ascorbic acid referred to in formula I as O-glycosyl
  • monosaccharides such as ribose, arabinose xylose, lyxose, allose, altrose, glucose, mannose, gulose, idose, galactose, talose, ribulose, xylulose, psicose, fructose, sorbose or tagatose.
  • both isomers ie in each case the D or L forms are included.
  • glucose, galactose or fructose are used.
  • disaccharides are also suitable, such as sucrose (or else called sucrose), lactose, trehalose, maltose, cellobiose, gentiobiose or melibiose.
  • sucrose or else called sucrose
  • lactose lactose
  • trehalose maltose
  • maltose cellobiose
  • gentiobiose melibiose
  • disaccharides are preferably sucrose or lactose, particularly preferably sucrose used.
  • the radical R 1 in formula I is hydroxy and R 2 is -O-alkyl, -OC (O) -alkyl, -OPO 3 M or O-glycosyl, as described above.
  • the radical R 2 in formula I is hydroxy and R 1 is -O-alkyl, -OC (O) -alkyl, -OPO 3 M or O-glycosyl, as described above.
  • both radicals R 2 and R are hydroxy.
  • R 3 or R 4 are each independently of one another hydroxy or a radical of the formula III
  • R 5 to R 9 are each independently of one another H, -OH, straight-chain or branched alkoxy group having 1 to 20 C atoms, fluorinated straight-chain or branched alkoxy group having 1 to 20 C atoms, -A, -NH 2 ( -NHA, -NA 2 , -NH- (CH 2 -CH 2 -O) n -H, -N [(CH 2 -CH 2 -O) n -H] 2 , - [NHA 2 ] X, - [NA 3 ] X, -SO 3 H, - [SO 3 ] X, 2H-benzotriazol-2-yl or -OC (O) -alkyl,
  • A is a straight-chain or branched alkyl group having 1 to 20 C atoms and
  • X is the counterion to the cations [NHA 2 ] + and [NA 3 ] + or the anion [SO 3 ] " ,
  • Dehydroascorbic acid ie preferably the radical R 4 is the formula III and R 3 is H.
  • Dehydroascorbinklauregrundgerüst this can be present in the D or L form or as a, in particular non-equimolar, mixture of the two enantiomeric forms.
  • the L-ascorbic acid or the L-dehydroascorbic acid is derivatized.
  • A denotes a straight-chain or branched alkyl group having 1 to 20 C atoms.
  • A is preferably a straight-chain or branched alkyl group having 1 to 10 C atoms, as described above.
  • A is preferably a straight-chain or branched alkyl group having 1 to 4 C atoms.
  • n is an integer from 1 to 25, preferably an integer from 1, 2, 3, 4 or 5.
  • X describes the counterion for the cations [NHA 2 ] + and [NA 3 ] + , where A has one of the meanings given above, preferably CI “ , Br “ , ⁇ or [SO 4] 2 " or the counterion of the anion [SO 3] " , preferably an ammonium ion or an alkali metal or alkaline earth metal cation such as Na + , K + , Mg 2+ or Ca 2+ .
  • Ascorbinklagerüsts is deprotonated and the charge is by a counter cation, such as an alkali or
  • the substituents R 5 to R 9 in the compounds of the formula I or II are preferably each independently H, straight-chain or branched alkoxy group having 1 to 20 C atoms, fluorinated straight-chain or
  • alkoxy group having 1 to 20 C atoms or -OC (O) -alkyl, wherein alkyl has a meaning given above or as preferred.
  • Alkoxy group preferably 1 to 10 C-atoms, most preferably 1 to 4 C-atoms.
  • the fluorinated straight-chain or branched alkoxy group preferably has 1 to 10 C atoms, very particularly preferably 1 to 4 C atoms.
  • At least one substituent of the substituents R 5 to R 9 is preferably a straight-chain or branched alkoxy group, as described above.
  • the radical R 6 is H.
  • the radical R 8 is H. More preferably, the radical R 5 is H or a straight-chain or branched alkoxy group, as described above.
  • the radical R 9 is H or a straight-chain or branched alkoxy group, as described above.
  • the radical R 7 is a straight-chain or branched alkoxy group having 1 to 20 C atoms, a fluorinated straight-chain or branched
  • the radical R 7 is particularly preferably a straight-chain alkoxy group having 1 to 10 C atoms, very particularly preferably 1 to 4 C atoms.
  • Preferred individual compounds of the formula I are the compounds
  • the compounds of the formula I or of the formula II can be prepared by processes as described in WO 2008/017346 or in WO 2010/127756. In particular, the compounds of formula I or II are prepared via esterifications. The necessary
  • the compounds of the formula I or II, as described above or described as preferred, are used in particular in agents for dyeing the keratin-containing fibers, in particular for dyeing human hair, which are selected for example from a color consolidator, a Farbnönlotion, a Farbfönschaum, a color rinse , a color gel or a color cream. However, they may also be included in permanent hair coloring agents, for example in multi-component systems.
  • the corresponding agents for dyeing the keratin-containing fibers as described above preferably contain the compound (s) of the formula I and / or II in amounts above 0.01% by weight and below 10% by weight, based in each case on the entire remedy.
  • Preferred agents for dyeing keratin-containing fibers are characterized in that they contain the compound (s) of the formula I or II in amounts of 0.05 to 5 wt .-%, preferably from 0.1 to 2.5 wt .-%, especially preferably from 0.25 to 1, 5 wt .-% and in particular from 0.4 to 1 wt .-%, each based on the total agent.
  • the corresponding agents containing at least one compound of the formula I and / or of the formula II are used for the color change of keratin-containing fibers, as described above, in particular human hair.
  • the color change can be carried out solely on the basis of the compound (s) of the formula I or II, but the agents can also additionally be used
  • color-changing substances such as more
  • the at least one compound of the formula I and / or of the formula II is preferably used in colorants which additionally contain 0.001 to 5% by weight of one or more several oxidation dye precursors and / or more direct
  • the agent for dyeing the keratin-containing fibers comprising at least one compound of the formula I and / or of the formula II, as before
  • an agent containing the oxidizing agent as the first component is often separated from the other colorant containing, for example, the first
  • Oxidation dye precursors used are used.
  • the agents may comprise or contain, substantially or consist of the said necessary or optional ingredients. Any compounds or components that can be used in the compositions are either known and commercially available or can be synthesized by known methods.
  • Another object of the invention is a process for dyeing keratin fibers, wherein an agent for dyeing keratin fibers containing at least one compound of formula I and / or II, as described above or described as preferred, at least once applied daily or at least twice or several times in succession on the keratin fiber, left on the fiber for some time, usually about 20 to 45 minutes, and then rinsed again or washed out with a shampoo.
  • the application period of the agent containing the at least one compound of the formula I and / or II is limited to one day, it is necessary to apply the agent to the keratin-containing fiber at least twice, preferably two to five times
  • Pretreatment can be dispensed with.
  • a further subject of the invention is a process for dyeing keratin-containing fibers, wherein an agent for dyeing keratin-containing fibers comprising at least one compound of formula I and / or II, as described above or described as preferred, on the pre-treated by means of a pretreatment keratin-containing Applied fiber, some time, usually about 20 to 45 minutes, left on the fiber, and then rinsed again or washed out with a shampoo.
  • Such a pretreatment agent may be basic, acidic or neutral, but is preferably basic in the process according to the invention.
  • the pretreatment agent preferably has NH 3 and / or (NH 4 ) CO 3 .
  • the pretreatment step is performed before the dyeing step, but it is also a simultaneous implementation of pretreatment step and dyeing step with appropriate formulation conceivable.
  • compositions containing at least one compound of formula I and / or II are prepared in which at least one compound of formula I and / or II, as described above, with at least one suitable carrier for cosmetic, pharmaceutical, dermatological preparations or household products and optionally excipients and / or fillers are mixed, in particular dispersed and / or emulsified and / or dissolved.
  • the compositions comprising the at least one compound of the formula I and / or II may contain further oxidation dye components.
  • Coupler components usually permit at least one substitution of a chemical residue of the coupler by the oxidized form of the developer component. This forms a covalent bond between the coupler and the developer component.
  • Couplers are preferably cyclic compounds which carry on cycle at least two groups selected from (i) optionally substituted amino groups and / or (ii) hydroxy groups. These groups are conjugated by a double bond system. When the cyclic compound is a six-membered ring, said groups are preferably in ortho position or meta position to each other.
  • 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.
  • Suitable developer-type oxidation dye components are p-phenylenediamine and its derivatives.
  • Suitable p-phenylenediamines are selected from one or more compounds of the group formed from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethyl p-phenylenediamine, 2,6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N, N-dipropylamine p-phenylenediamine, 4-amino-3-methyl- (N, N-diethyl) aniline, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 4-N, N
  • p-phenylenediamine derivatives are selected from at least one compound of the group p-phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, 2- (1, 2-dihydroxyethyl) -p-phenylenediamine, N, N Bis (2-hydroxyethyl) -p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1H-imidazol-1-yl) propyl] amine, 2-methoxymethyl-p- phenylenediamine and the physiologically acceptable salts of these compounds.
  • suitable developer components which can be used are compounds which contain at least two aromatic nuclei which are substituted by amino and / or hydroxyl groups.
  • further suitable developer components are selected from at least one compound of the group formed from N, N'-bis (2-hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diaminopropan-2 ol, N, N'-bis (2-hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4 , -aminophenyl) -tetrmethylenediamine, N, N 'Bis- (2-hydroxyethyl) -N, N , -bis- (4 , -aminophenyl) -tetramethylenediamine, N, N'-bis- (4- (methylamino) phenyl) tetramethylenediamine, N ) N'- Dieth
  • binuclear Developer components are selected from 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) -propan-2-ol, N, N'-bis (4-aminophenyl) -1, 4-diazacycloheptane, 1, 10-bis- (2,5-diaminophenyl) - 1, 4,7,10-tetraoxadecan or one of the physiologically acceptable salts of these compounds.
  • p-aminophenol derivative or one of its physiologically tolerable salts.
  • Preferred p-aminophenols are p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methyl-phenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4-amino-3-hydroxymethylphenol , 4-Amino-2- (2-hydroxyethoxy) phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethyl-phenol, 4-amino-2-aminomethylphenol, 4 -Amino-2- (2-hydroxyethylaminomethyl) phenol, 4-amino-2- (1,2-dihydroxyethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2-chlorophenol, 4-amino-2 , 6-dichlorophenol, 4-amino-2- (die
  • Particularly preferred compounds are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- (1, 2-dihydroxyethyl) phenol and 4-amino-2- (diethylaminomethyl) phenol.
  • the developer component may be selected from o-aminophenol and its derivatives such as 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.
  • the developer component may be selected from heterocyclic developer components, such as pyrimidine derivatives, pyrazole derivatives, pyrazolopyrimidine derivatives or their physiologically acceptable salts.
  • Preferred pyrimidine derivatives are in particular the compounds 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino ⁇ .Se-triaminopyrimidine , 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine.
  • pyrazole derivatives are the compounds selected from 4,5-diamino-1-methylpyrazole, 4,5-diamino-1- (2-hydroxyethyl) pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1- (4'-chlorobenzyl) pyrazole, 4,5-diamino-1,3-dimethylpyrazole, 4 , 5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino 3-methylpyrazole, 4,5-diamino-3-t-butyl-1-methylpyrazole, 4,5-diamino-1-t-butyl-3-methylpyrazole, 4,5-diamino-1- (2-hydroxyethyl) 3-methylpyrazole,
  • Particularly suitable pyrazolopyrimidines are pyrazolo [1,5-a] pyrimidines, with preferred pyrazolo [1,5-a] pyrimidines being selected from pyrazolo [1,5-a] pyrimidine-3,7-diamine, 2,5-dimethyl pyrazolo [1,5-a] pyrimidine-3,7-diamine, pyrazolo [1,5-a] pyrimidine-3,5-diamine, 2,7-dimethylpyrazolo [1,5-a] pyrimidine-3,5 -diamine, 3-aminopyrazolo [1,5-a] pyrimidin-7-ol, 3-aminopyrazolo [1,5-a] pyrimidin-5-ol, 2- (3-aminopyrazolo [1, 5-a] pyrimidin-7-ylamino) ethanol, 2- (7-aminopyrazolo [1,5-a] pyrimidin-3-ylamin
  • developer components are selected from at least one compound from the group formed from p-phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine,
  • developer components are p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1 H imidazol-1-yl) propyl] amine, and / or 4,5-diamino-1- (2-hydroxyethyl) pyrazole and their physiologically acceptable salts.
  • the developer components are preferably used in an amount of 0.0001 to 10 wt .-%, preferably 0.001 to 5 wt .-%, each based on the total colorant.
  • Suitable coupler-type oxidation dye components are preferably selected from m-aminophenol and / or its derivatives, m-diaminobenzene and / or derivatives thereof, o-diaminobenzene and / or derivatives thereof, o-aminophenol and / or derivatives thereof, naphthalene derivatives having at least one hydroxy group, Di- or trihydroxybenzene and / or derivatives thereof, pyridine derivatives, pyrimidine derivatives, monohydroxyindole derivatives and / or monoaminoindole derivatives, monohydroxyindoline derivatives and / or monoaminoindoline derivatives, pyrazolone derivatives, such as, for example, 1-phenyl-3-methylpyrazol-5-one, Morpholine derivatives such as 6-hydroxybenzomorpholine or 6-aminobenzomorpholine,
  • Quinoxaline derivatives such as 6-methyl-1,2,3,4-tetrahydroquinoxaline and / or mixtures of two or more compounds from one or more of these classes.
  • Further usable coupler components such as m-aminophenols or derivatives thereof, are preferably selected from at least one compound from the group formed from 3-aminophenol, 5-amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3 Amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2,6-dimethyl-3-aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5-amino-4-chloro-2 methylphenol, 5-amino-4-methoxy-2-methylphenol, 5- (2'-hydroxyethyl) amino-2-methylphenol, 3-diethylaminophenol, N-cyclopentyl-3-aminophenol, 1, 3-dihydroxy-5- (methylamitio ) benzen
  • Coupler components such as e.g. 3-diaminobenzenes or their derivatives, are preferably selected from at least one compound from the group formed from m-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, 2- ( ⁇ 3 - [(2-hydroxyethyl) amino] -2-methoxy-5-methylphenyl ⁇ amino) ethanol, 2- ( ⁇ 3 - [(2-hydroxyethyl) amino] -4,5-dimethylphenyl ⁇ amino) ethanol
  • Coupler components such as e.g. o-diaminobenzenes or their derivatives are preferably selected from at least one compound from the group formed from 3,4-diaminobenzoic acid and 2,3-diamino-1-methylbenzene and their physiologically acceptable salts.
  • Coupler components such as di- or trihydroxybenzenes and their derivatives, are selected from at least one compound of the group formed from resorcinol, resorcinol monomethyl ether, 2-methylresorcinol, 5-methylresorcinol, 2.5- Dimethylresorcinol, 2-chlororesorcinol, 4-chlororesorcinol, pyrogallol and 1,2,4-trihydroxybenzene.
  • Pyridine derivatives are selected from at least one compound of the group formed from 2,6-dihydroxypyridine, 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6 -methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dihydroxy-4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine, 3,5-diamino-2,6 -dimethoxypyridine, 3,4-diaminopyridine, 2- (2-methoxyethyl) amino-3-amino-6-methoxypyridine, 2- (4'-methoxyphenyl) amino-3-aminopyridine and their physiologically acceptable salts.
  • Pyridine derivatives are selected from at least one compound of the group formed from 2,6-dihydroxypyridine, 2-amino-3-hydroxypyridine, 2-amino-5-chloro
  • Suitable naphthalene derivatives having at least one hydroxyl group as the coupler component are selected from at least one compound of the group formed from 1-naphthol, 2-methyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1-naphthol, 1 , 3-
  • Dihydroxynaphthalene 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 2,3-dihydroxynaphthalene.
  • Suitable coupler component indole derivatives are selected from 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole and their physiologically acceptable salts.
  • Indoline derivatives suitable as a coupler component are preferably selected from 4-hydroxyindoline, 6-hydroxyindoline and 7-hydroxyindoline and their physiologically acceptable salts.
  • Suitable pyrimidine derivatives as the coupler component are selected from at least one compound of the group formed from 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine , 2-amino-4-methylpyrimidine, 2-amino-4-hydroxy-6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine and their physiologically acceptable salts.
  • Suitable coupler components are selected 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-
  • resorcinol particularly preferred are resorcinol, 2-methylresorcinol, 5-amino-2-methylphenol, 3-aminophenol, 2- (2,4-diaminophenoxy) ethanol, 1, 3-bis (2,4-diaminophenoxy) propane, 1 Methoxy-2-amino-4- (2'-hydroxyethylamino) benzene, 2-amino-3-hydroxypyridine and 1-naphthol and one of their physiologically acceptable salts.
  • the coupler components are preferably used in an amount of 0.0001 to 10 wt .-%, preferably 0.001 to 5 wt .-%, each based on the total agent.
  • dyeing or tinting agents which contain as coloring component so-called direct drawers. These are dye molecules directly on the Apply substrate and do not need an oxidative process to form the paint. These dyes include, for example, the henna already known from antiquity for coloring body and hair. These dyeings are generally much more sensitive to shampooing than the oxidative dyeings, so that a much more undesirable change in shade or even a visible, homogeneous color loss occurs much more quickly.
  • compositions according to the invention may contain at least one further substantive dye. These are dyes that are applied directly to the hair and do not require an oxidative process to form the color. Direct dyes are
  • nitrophenylenediamines usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • the substantive dyes are used, in each case preferably in an amount of 0.001 to 20 wt .-%, based on the total preparation.
  • the total amount of substantive dyes is preferably at most 20% by weight.
  • Direct dyes can be subdivided into anionic, cationic and nonionic substantive dyes.
  • Preferred anionic substantive dyes are those under the international designations (INCI) 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 and Acid Black 52 known compounds.
  • Basic Blue 26, Basic Violet 2 and Basic Violet 14 aromatic systems substituted with a quaternary nitrogen group, such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as
  • Suitable nonionic substantive dyes are in particular nonionic nitro and quinone dyes and neutral azo dyes.
  • direct dyes also naturally occurring dyes may be used, as for example in henna red, henna neutral, henna black, chamomile flower, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included.
  • a first class of oxo dye precursors are compounds with
  • This first class is called a component (Oxo1).
  • Oxofarbstoffvor area form CH-acidic compounds and compounds having primary or secondary amino group or hydroxy group, which in turn are selected from compounds of the group formed from primary or secondary aromatic amines,
  • This second class is called a component (Oxo2).
  • the aforementioned components (oxo1) and (oxo2) are generally not themselves dyes, and therefore are not in themselves suitable for coloring keratin-containing fibers. In combination, they form in a non-oxidative process called oxo dyeing, Dyes off. The resulting dyeings are partial
  • Oxidation staining are comparable.
  • Carbonyl group contains (component (Oxo1))
  • Reactive carbonyl compounds as component (oxo1) have in the context of the invention at least one carbonyl group as a reactive group which reacts with the component (oxo2) to form a covalent bond.
  • Preferred reactive carbonyl compounds are selected from compounds which have at least one formyl group and / or at least one keto group, in particular at least one
  • Compounds are used as component (Oxo1), in which the reactive carbonyl group is derivatized or masked such that the reactivity of the carbon atom of the derivatized carbonyl group over the component (Oxo2) is always present.
  • component (Oxo1) in which the reactive carbonyl group is derivatized or masked such that the reactivity of the carbon atom of the derivatized carbonyl group over the component (Oxo2) is always present.
  • These derivatives are preferably addition compounds
  • Component (Oxo1) is derived in this case c) from an aldehyde) to the carbon atom of the carbonyl group of the reactive carbonyl compound.
  • Benzaldehyde and / or cinnamaldehyde and / or naphthaldehyde and / or at least one derivative of these abovementioned aldehydes, which in particular carry one or more hydroxyl, alkoxy or amino substituents, are very particularly preferably used as the reactive carbonyl component in the oxo dyeing.
  • CH-acidic compounds are generally considered those compounds which carry a bound to an aliphatic carbon atom hydrogen atom, wherein due to electron-withdrawing substituents activation of the corresponding carbon-hydrogen bond is effected.
  • CH-acid compounds there are no limits to the choice of CH-acid compounds, as long as the
  • a visible to the human eye colored compound is obtained.
  • these are preferably those CH-acidic compounds which contain an aromatic and / or a heterocyclic radical.
  • the heterocyclic radical may again be alphatic or aromatic.
  • Particularly preferred are the CH-acidic
  • the CH-acidic compounds of the oxo dye precursors of the component (oxo2a) are most preferably selected from at least one compound of the group consisting of 2- (2-furoyl) -acetonitrile, 2- (5-bromo-2-furoyl) -acetonitrile, 2- (5-methyl-2-trifluoromethyl-3-furoyl) -acetonitrile, 3- (2,5-dimethyl-3-furyl) -3-oxopropanitrile, 2- (2-thenoyl) -acetonitrile, 2- (3-thenoyl) -acetonitrile, 2- (5-fluoro-2-thenoyl) - acetonitrile, 2- (5-chloro-2-thenoyl) -acetonitrile, 2- (5-bro-2-thenoyl) -acetonitrile, 2- (2,5-dimethylpyrrol-3-oyl) -acetonitrile, 1H
  • component (Oxo2b) at least one
  • Oxidation dye precursor having at least one primary or secondary amino group and / or at least one hydroxy group can be used. Preferred suitable representatives are found under the execution of the oxidation dye precursors. However, it is
  • the above-mentioned compounds of component (Oxo1) and the component (Oxo2) are, when used, each preferably in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the total Means, used.
  • the agents additionally preferably contain hydrogen peroxide.
  • Such agents for dyeing and optionally simultaneously whitening keratin-containing fibers are particularly preferred which contain from 0.5 to 15% by weight, preferably from 1 to 12.5% by weight, particularly preferably from 2.5 to 10% by weight. and in particular 3 to 6 wt .-% hydrogen peroxide (calculated as 100% H 2 0 2 ) included.
  • the hydrogen peroxide can also be used in the form of its addition compound to solid carriers, is preferred
  • Hydrogen peroxide itself used.
  • the hydrogen peroxide is added as a solution or in the form of a solid addition compound of hydrogen peroxide to inorganic or organic compounds, such as
  • aqueous hydrogen peroxide solutions Very particular preference is given to aqueous hydrogen peroxide solutions.
  • 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 6-12% solutions in water are used.
  • at least one bleach booster is additionally preferred in cosmetic preparations
  • Bleach boosters are preferably used to increase the bleaching action of the oxidizing agent, in particular the hydrogen peroxide.
  • Suitable bleach boosters are
  • Bleach boosters are preferably peroxo compounds, in particular inorganic peroxo compounds.
  • bleach-enhancing compounds are preferably peroxo compounds, in particular inorganic peroxo compounds.
  • peroxo compounds Hydrogen peroxide itself.
  • selection of peroxo compounds is not subject to any restrictions.
  • Preferred peroxo compounds are peroxydisulfate salts, persulfate salts, peroxydiphosphate salts
  • the peroxydisulfates in particular ammonium peroxydisulfate, are preferred.
  • agents for dyeing and, if appropriate, simultaneous lightening of keratinic fibers are preferred, which additionally contain 0.01 to 2% by weight.
  • ammonium peroxydisulfate and preferred agents containing at least two different peroxydisulfates are also particularly preferred.
  • persulfates in particular the mixture of potassium peroxosulfate, referred to as Caro's salt,
  • the bleach boosters are contained in the cosmetic agents according to the invention preferably in amounts of from 5 to 30% by weight, in particular in amounts of from 8 to 20% by weight, based in each case on the weight of the ready-to-use agent.
  • the dyeing and / or brightening agents contain nonionic surfactants.
  • Such surfactants having an HLB of 5.0 and greater are preferred.
  • HLB value is expressly on the remarks in Hugo Janistyn, Handbook of the
  • Particularly preferred non-ionic surface-active substances are substances that are commercially available as solids or liquids in pure form because of their ease of processing.
  • Alkyl chain lengths such as those obtained with products based on natural fats and oils. Even with alkoxylated products, mixtures of different degrees of alkoxylation are usually present.
  • purity in this context refers rather to the fact that the selected substances should preferably be free from solvents, stabilizers and other impurities.
  • Compositions contain at least one ammonium compound from the group ammonium chloride, ammonium carbonate, ammonium bicarbonate, ammonium sulfate and / or ammonium carbamate in an amount of 0.5 to 10, preferably 1 to 5 wt .-%, based on the total composition of the composition.
  • the dyeing and / or brightening agents according to the invention may contain further active ingredients, auxiliaries and additives, such as
  • nonionic polymers such as vinyl pyrrolidone / vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone / vinyl acetate copolymers and polysiloxanes,
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallylammonium chloride copolymers, diethyl sulfate quaternized dimethylaminoethylmethacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol,
  • anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert-butyl acrylamide terpolymers
  • Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, Linseed gums, dextrans, cellulose derivatives, eg methylcellulose, hydroxyalkylcellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as e.g. As bentonite or fully synthetic hydrocolloids such.
  • polyvinyl alcohol polyvinyl alcohol
  • hair-conditioning compounds such as phospholipids, for example soya lecithin, egg lecithin and cephalins,
  • Protein hydrolysates in particular elastin, collagen, keratin,
  • Solvents and investigators such as ethanol, isopropanol, ethylene glycol, propylene glycol, propylene glycol, glycerol and diethylene glycol,
  • fiber-structure-improving active substances in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fructose, fructose and lactose,
  • quaternized amines such as methyl-1-alkylamidoethyl-2-alkylimidazolinium methosulfate
  • Anti-dandruff agents such as Piroctone Olamine, Zinc Omadine and Climbazole,
  • Cinnamic acid derivatives and triazines Cinnamic acid derivatives and triazines
  • Substances for adjusting the pH for example customary acids, in particular edible acids and bases,
  • panthenol pantothenic acid
  • allantoin allantoin
  • Vitamins such as extracts of green tea, oak bark, nettle, witch hazel, hops, chamomile, burdock root,
  • Consistency factors such as sugar esters, polyol esters or polyalkyl ethers
  • -Complexing agents such as EDTA, NTA, ß-alaninediacetic and
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers
  • Pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate,
  • Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air,
  • compositions according to the invention may contain the ingredients 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 or other preparations which are suitable for use on the hair.
  • a powdered or tablet-shaped formulation which is preferred for dyeing and / or brightening agents.
  • aqueous-alcoholic solutions are aqueous solutions containing from 3 to 70% by weight of a C 1 -C 4 -alcohol, in particular ethanol or isopropanol.
  • aqueous-alcoholic solutions may additionally contain other organic solvents, such as
  • Preferred agents are characterized in that they additionally contain a nonaqueous solvent, with particularly preferred agents containing the solvent in a concentration of 0.1-30% by weight, preferably in a concentration of 1-20% by weight, very particularly preferably in a concentration of 2%. 10 weight percent, each based on the agent included.
  • the solvent is selected from:
  • the pH of the compositions according to the invention can be determined by suitable
  • Ingredients such as acidifiers or alkalizers can be adjusted in a wide range.
  • Oxidative staining of the keratin-containing fibers can in principle be carried out with atmospheric oxygen in the presence of oxidation dye precursors.
  • a chemical oxidizing agent is used.
  • the oxidizing agents are persulfates, chlorites and in particular
  • the agents may contain metal ions or metal ion complexes, for example Cu, Fe, Mn or Ru ions or complexes of these ions.
  • metal ions or metal ion complexes for example Cu, Fe, Mn or Ru ions or complexes of these ions.
  • the complexing agents can be selected from polycarboxylic acids, geminal diphosphonic acids, aminophosphonic acids, phosphonopolycarboxylic acids, cyclodextrins, aminodicarboxylic acids, polyacetals or phosphonates.
  • the agents are formulated low in water or anhydrous.
  • Preferred agents are characterized in that they contain less than 5 wt .-%, preferably less than 2 wt .-%, more preferably less than 1 wt .-% and in particular less than 0.5 wt .-% water.
  • the water content of the agents can be determined, for example, by means of titration according to Karl Fischer.
  • R 1 or R 2 are each independently of one another hydroxy, -O-alkyl, -OC (O) -alkyl, -OPO 3 M or O-glycosyl,
  • Alkyl is a straight-chain or branched alkyl group having 1 to 10 C atoms
  • M alkali or alkaline earth metal cation or H means
  • R 3 or R 4 are each independently hydroxy or the formula
  • R 5 to R 6 are each independently H, -OH, -OA, -A, -NH 2 , -NHA, - NA 2) -NH- (CH 2 -CH 2 -O) n -H, -N [( CH 2 -CH 2 -O) n -H] 2 , - [NHA 2 ] X, - [NA 3 ] X, -SO 3 H, - [SO 3 ] X or 2H-benzotriazol-2-yl and
  • A is alkyl having 1 to 4 C atoms
  • n is an integer from 1 to 25,
  • X is the counterion to the cations [NHA 2 ] + and [NA 3 ] + or the anion [SO 3 ] - and
  • Y and Z are each independently -ascorbyl, hydroxy, -O-2-ethylhexyl, -O-hexyl, -OA or -NH-C (CH 3 ) 3 ,
  • agents for dyeing keratinous fibers may be included in agents for dyeing keratinous fibers, whether for product protection of sensitive ingredients of the composition, as direct dye or oxidation dye component.
  • Three hair fluids (hair rinses) a), b), c) are examined for their coloring effect by application to strands of hair (Euro hair blond).
  • Recipe a) contains 1% of the UV filter 4-methoxycinnamic acid 6-O-ascorbate.
  • formulations containing equimolar amounts of ascorbic acid (0.52% in formulation b)) and ascorbic acid acetonide (0.64% in formulation c)) are used.
  • the base formulation used for a), b), c) contains the following
  • the components of the oil and water phase are combined in each case, the mixtures heated on the steam bath (80 ° C) and dissolved or melted with stirring.
  • the oil phase is emulsified in portions into the water phase.
  • the remission probe used is the model Harrick, Barellino (Serial No BRLVA358431109019, wavelength range 360-830nm, interval 1nm, observation angle 2 °, illumination CIED65, baseline correction against white standard (barium sulfate)).
  • Carbomer mica, dimethiconol, trideceth-12, tocopheryl acetate, perfume, isoleucine, lysine, sodium benzoate, Cl 77891, PPG-9.
  • Advantages of the following listed formulations are that they have a very favorable influence on the properties of the hair, such as hair handling, combability, smoothness, volume, body, elasticity and gloss.
  • Example 2 hair conditioner
  • Example 3 hair conditioner
  • propellant gases e.g. Propane or butane or mixtures thereof are used.
  • Example 9 Intensive Tinting Application (developer containing 4-ethoxycinnamic acid 6-O-ascorbate in place of hydrogen peroxide)
  • 10mL developer B commercial developer emulsion see below
  • the respective mixtures are homogenized by shaking in air.
  • Tinting Care Cream Aqua, Cetearyl Alcohol,
  • Ethanolamines Sodium Laureth Sulfates, Cocamidopropyl Betaine, coconut Alcohol, Toluene-2,5-Diamines Sulfates, Polyquaternium-22, Ceteareth-20, Sodium Chlorides, 2-Methylresorcinol, Disodium Cocoamphodipropionate, Sodium Sulphites, Ascorbic Acid, Macademia Ternifolia Seed Oil, Sodium silicate, 4-chlororesorcinol, perfume, etidronic acid, 2-amino-3-hydroxypyridine, resorcinol, 2-amino-6-chloro-4-nitrophenol, m-aminophenol, methyl alcohol.
  • Ingredients Developer B Aqua, Hydrogen peroxide, Acrylates Copolymer, Etidronic Acid, Sodium Laureth Sulfate, 2,6-Dicarboxypyridine, Disodium Pyrophosphate, Dimethicone

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation de dérivés spéciaux d'acide ascorbique pour teinter des fibres kératiniques, à savoir en tant que colorants directs pour la production d'un produit pour teinter des fibres kératiniques, ainsi qu'un procédé pour teinter des fibres kératiniques, notamment des cheveux humains.
EP11773197.6A 2010-11-19 2011-10-19 Utilisation de dérivés d'acide ascorbique pour teinter des fibres kératiniques Withdrawn EP2640351A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010051725A DE102010051725A1 (de) 2010-11-19 2010-11-19 Verwendung von Ascorbinsäurederivaten zur Färbung von keratinhaltigen Fasern
PCT/EP2011/005269 WO2012065671A2 (fr) 2010-11-19 2011-10-19 Utilisation de dérivés d'acide ascorbique pour teinter des fibres kératiniques

Publications (1)

Publication Number Publication Date
EP2640351A2 true EP2640351A2 (fr) 2013-09-25

Family

ID=45390051

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11773197.6A Withdrawn EP2640351A2 (fr) 2010-11-19 2011-10-19 Utilisation de dérivés d'acide ascorbique pour teinter des fibres kératiniques

Country Status (5)

Country Link
US (1) US8702813B2 (fr)
EP (1) EP2640351A2 (fr)
JP (1) JP2013544247A (fr)
DE (1) DE102010051725A1 (fr)
WO (1) WO2012065671A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013225191A1 (de) 2013-12-06 2015-06-11 Henkel Ag & Co. Kgaa Mittel zum oxidativen Färben von Haaren enthaltend spezielle Kombinationen von Entwicklern und Kupplern
DE102013225183A1 (de) * 2013-12-06 2015-06-11 Henkel Ag & Co. Kgaa Mittel zum Färben von Haaren enthaltend spezielle Kombinationen von Entwicklern und Kupplern
DE102017221773A1 (de) * 2017-12-04 2019-06-06 Henkel Ag & Co. Kgaa Kosmetische Zusammensetzung zur Behandlung von keratinischen Fasern
DE102018222024A1 (de) * 2018-12-18 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum Färben von keratinischem Material mit Färbemittel und saurem Nachbehandlungsmittel

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19607751A1 (de) * 1996-02-29 1997-09-04 Henkel Kgaa Neue Aminophenol-Derivate und deren Verwendung
US5961666A (en) * 1997-11-19 1999-10-05 Lim; Mu-Ill Hair dye compositions containing 3-substituted-4-aminophenols and 2-substituted-1-naphthols
FR2785183B1 (fr) 1998-11-04 2002-04-05 Oreal COMPOSITION TINCTORIALE CONTENANT UN COLORANT DIRECT CATIONIQUE ET UNE PYRAZOLO-[1,5-a]- PYRIMIDINE A TITRE DE BASE D'OXYDATION, ET PROCEDES DE TEINTURE
DE19913427A1 (de) * 1999-03-25 2000-09-28 Wella Ag Verwendung von reduzierenden Verbindungen zur Verstärkung und Strukturverbesserung von Keratin enthaltenden Materialien
JP4083702B2 (ja) * 2004-04-09 2008-04-30 ホーユー株式会社 酸化染毛剤組成物
FR2887440B1 (fr) * 2005-06-28 2009-07-10 Oreal Procede de traitement photoprotecteur des fibres keratiniques par application de chaleur
DE102006037724A1 (de) * 2006-08-11 2008-02-14 Merck Patent Gmbh Verwendung von Ascorbinsäurederivaten zur Funktionalisierung von Matrices
JP5284593B2 (ja) * 2007-02-26 2013-09-11 ホーユー株式会社 染色処理方法
JP2009035509A (ja) * 2007-08-01 2009-02-19 Green Products Laboratory Ltd アスコルビン酸エステル及びその合成方法
FR2939035B1 (fr) 2008-11-28 2011-01-21 Oreal Utilisation de derives acetaliques de l'acide ascorbique en coloration des fibres keratiniques humaines, composition les comprenant, procede de coloration et dispositif
US8598228B2 (en) 2009-05-08 2013-12-03 Merck Patent Gmbh Cinnamic acid ascorbates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2012065671A2 *

Also Published As

Publication number Publication date
WO2012065671A3 (fr) 2012-07-26
US20130228192A1 (en) 2013-09-05
US8702813B2 (en) 2014-04-22
WO2012065671A2 (fr) 2012-05-24
JP2013544247A (ja) 2013-12-12
DE102010051725A1 (de) 2012-05-24

Similar Documents

Publication Publication Date Title
WO2009135700A1 (fr) Agent éclaircissant contenant des dérivés d'acylpyridinium cationiques, des co-activateurs de blanchiment et du peroxyde d'hydrogène
DE102005013488A1 (de) Mittel zum gleichzeitigen Färben und Aufhellen von keratinhaltigen Fasern
EP2315576A1 (fr) Dérivés cationiques d'acétylpyridine servant d'activateurs d'éclaircissement
DE102009029043A1 (de) Intensive, schonende Färbemittel
EP2306967B1 (fr) Coloration au moyen d'un polymère cationisable
WO2010022995A1 (fr) Dérivés cationiques de dihydroisochinoline servant d'activateurs de décoloration
EP2477701B1 (fr) Produit de coloration et d'éclaircissement doux ayant une performance d'éclaircissement améliorée
EP2143414A2 (fr) Colorant d'oxydation contenant un aminoacide basique, du sulfate d'ammonium et des alkanolamines
EP2640351A2 (fr) Utilisation de dérivés d'acide ascorbique pour teinter des fibres kératiniques
EP2440174B1 (fr) Post-traitement pour fixer la couleur
DE102009044920A1 (de) Verwendung bestimmter Aminosäuren in Färbemitteln keratinischer Fasern zur Farbintensivierung
DE102011085416A1 (de) Farbintensivierung durch Haarfärbemittel mit Polysaccharid-Kombination
DE102009027678A1 (de) Färbemittel mit verbessertem Farberhalt
EP2787989A1 (fr) Dérivés du glucuronolactone comme substances auto-bronzantes
EP2356978B1 (fr) Colorant doté d'acides aminés déterminés
EP2552394B1 (fr) Agent colorant comprenant un complexe d'acylpyridinium lipophile
DE102009054569A1 (de) Pflegende Haarbehandlungsmittel zur Farbveränderung
WO2010072576A2 (fr) Colorant capillaire à action soignante
DE102009001483A1 (de) Haarbehandlungsmittel mit Kirschkernöl/-blütenextrakt
DE102009029275A1 (de) Pflegende Haarfarbe
EP1772168A1 (fr) Procédé de teinture oxidative de fibres kératiniques
DE102011085173A1 (de) Intensive Haarfärbemittel mit Zuckerzusatz
DE202009000769U1 (de) Neue Färbemittel
DE102013226039A1 (de) Pflegende Färbe- und Blondiermittel
DE102013226144A1 (de) "Pflegende Färbe- und Blondiermittel mit verbessertem Volumen"

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20130412

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

DAX Request for extension of the european patent (deleted)
GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RIC1 Information provided on ipc code assigned before grant

Ipc: D06P 1/32 20060101ALI20160718BHEP

Ipc: A61Q 5/10 20060101ALI20160718BHEP

Ipc: A61K 8/49 20060101ALI20160718BHEP

Ipc: A61Q 5/02 20060101ALI20160718BHEP

Ipc: A61Q 5/06 20060101ALI20160718BHEP

Ipc: A61K 8/67 20060101AFI20160718BHEP

Ipc: A61Q 5/12 20060101ALI20160718BHEP

INTG Intention to grant announced

Effective date: 20160819

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20170103