WO2016020112A1 - Produit précurseur de colorants d'oxydation - Google Patents

Produit précurseur de colorants d'oxydation Download PDF

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Publication number
WO2016020112A1
WO2016020112A1 PCT/EP2015/064414 EP2015064414W WO2016020112A1 WO 2016020112 A1 WO2016020112 A1 WO 2016020112A1 EP 2015064414 W EP2015064414 W EP 2015064414W WO 2016020112 A1 WO2016020112 A1 WO 2016020112A1
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Prior art keywords
group
amino
hydroxy
alkyl group
oxidation dye
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PCT/EP2015/064414
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German (de)
English (en)
Inventor
Antje Gebert-Schwarzwälder
Ralph Nemitz
Astrid Kroos
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Henkel Ag & Co. Kgaa
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Publication of WO2016020112A1 publication Critical patent/WO2016020112A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/418—Amines containing nitro groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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

Definitions

  • the invention relates to agents for oxidative dyeing change of keratin fibers, in particular human hair, which contain new oxidation dye precursors of the type of oxy, thio and / or aza-bisbenzene. Furthermore, the invention relates to the use of these oxidation dye precursors in the dyeing of keratinic fibers to obtain dyeings having improved perspiration fastness.
  • the change in the shape and color of the hair is an important area of modern cosmetics dar.
  • fashionable color design of hairstyles or lamination of gray hair or even white hair with fashionable or natural colors the consumer accesses to color-changing agents.
  • oxidation colorants For permanent, intensive colorations with corresponding fastness properties, so-called oxidation colorants are used. Such colorants usually contain oxidation dye precursors, so-called developer components and coupler components. The developer components form the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with coupling with one or more coupler components. The oxidation colorants are characterized by intensive, outstanding, long-lasting dyeing results.
  • coupler components m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used.
  • Suitable coupler substances are in particular 1-naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3 -methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis- (2,4-diaminophenoxy) -propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3 -aminophenol, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-chloro-5-aminophenol.
  • Good oxidation dye precursors should fulfill the following conditions in the first place: They must in the oxidative coupling, the desired color shades in sufficient intensity and Train authenticity. You must also have a good AufziehFab on the fiber, especially in human hair no significant differences between strained and freshly regrowed hair may exist (leveling ability). They should be resistant to light, heat, sweat, friction and the influence of chemical reducing agents, eg permanent wave liquids. After all, they should not stain the scalp too much, and above all, they should be safe from a toxicological and dermatological point of view. Furthermore, the coloring obtained by bleaching should be easily removed from the hair again, if the person treated expresses a short-term change in color (good color removal behavior).
  • the object of the present invention was therefore to find new coupler components which meet the requirements imposed on oxidation dye precursors and provide intensive colorations with good fastness properties, in particular with good perspiration fastness.
  • a first object of the invention is a means for oxidative color change keratinischer
  • Y1, Y2 independently of one another represent a group R6R7N-, a hydroxy group, a C 1 -C 6 -alkyl group or a cyano group,
  • X represents an oxygen atom (-O-), a sulfur atom (-S-) or a
  • R1, R2, R5 independently of one another represent a hydrogen atom, a ⁇ - ⁇ -alkyl group, a C2-C6-alkenyl group, a hydroxy-C2-C6-alkyl group, a polyhydroxy-C2-C6-alkyl group, a hydroxy group, a ⁇ - ⁇ Alkoxy group, a cyano group, a C 1 -C 6 -alkoxycarbonyl group, a nitro group, an aryl group or a halogen atom (fluorine, chlorine,
  • R3, R4 independently represent a hydrogen atom, a ⁇ - ⁇ -
  • Alkyl group a C2-C6 alkenyl group, a hydroxy-C2-C6-alkyl group, a polyhydroxy-C2-C6-alkyl group, a hydroxy group, a ⁇ - ⁇ - alkoxy group, an amino group, a group R9R10N-, a cyano group, a Ci -C6-alkoxycarbonyl group, a nitro group, an aryl group or a halogen atom (fluorine, chlorine, bromine or iodine),
  • R6, R7, R8, R9, R10 independently represent a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a hydroxy-C2-C6 alkyl group, a polyhydroxy-C2-C6 alkyl group or an aryl group with the proviso that at least one of the radicals from the group Y1 and Y2 stands for one group
  • Keratin fibers are wool, furs, feathers and especially human hair.
  • the colorants of the invention can in principle but also for dyeing other natural fibers such.
  • cotton, jute, sisal, linen or silk modified natural fibers, such as regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose can be used.
  • the agents according to the invention contain the oxidation dye precursors (A) of the formula (I) in a cosmetic carrier, preferably in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a cosmetic carrier preferably in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier are, for example, creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, foam aerosols, foam formulations or other preparations which are suitable for use on the hair.
  • surfactant-containing foaming solutions such as shampoos, foam aerosols, foam formulations or other preparations which are suitable for use on the hair.
  • aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing from 3 to 70% by weight of a C 1 -C 4 -alcohol, in particular ethanol or isopropanol.
  • the compositions of the invention may additionally contain other organic solvents, such as methoxybutanol, benzyl alcohol, ethyl diglycol or 1, 2-propylene glycol. Preference is given to all water-soluble organic solvents.
  • oxidative color change agent refers to oxidative dyeing agents which contain at least one oxidation dye precursor of formula (I)
  • the formation of the dyeing may be effected by the presence of atmospheric oxygen, but preferably by the presence of an oxidizing agent other than atmospheric oxygen.
  • the keratin fiber is at the same time lightened more or less strongly during dyeing since the oxidizing agent not only enhances the dye formation process of the dye Developers and couplers initiated, but also the hair-borne pigments (melanins) oxidatively destroyed.
  • the oxidative color change may therefore primarily be a coloration (with a high proportion of dyestuff) or, primarily, a lightening (with a high proportion of oxidant).
  • the oxidation dye precursors are used mainly for the nuance of the Aufhell Librariess.
  • the agents according to the invention for the oxidative color change of keratinic fibers contain, as an oxidation dye precursor (A) essential to the invention, one or more compounds of the formula (I).
  • the compounds of formula (I) are coupler type oxidation dye precursors. The following are examples of the substituents mentioned in formula (I)
  • Y1, Y2, X, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are mentioned by way of example:
  • a hydroxy group means a group -OH.
  • C 1 -C 6 -alkyl radicals are -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH (CH 3 ) 2, -CH 2 CH 2 CH 2 CH 3 , -CH 2 CH (CH 3 ) 2, -CH (CH 3 ) CH 2 CH 3 , -C (CH 3 ) 3 , - (CH 2) 4 CH 3 , - (CH 2) 5 CH 3 .
  • Particularly preferred alkyl radicals are methyl and ethyl.
  • C2-C6 alkenyl groups are prop-2-enyl (allyl group), 2-methyl-prop-2-enyl, but-3-enyl, but-2-enyl, pent-4-enyl or pent-3-enyl
  • Examples of C 1 -C 6 hydroxyalkyl groups are -CH 2 OH, CH 2 CH 2 OH, -CH 2 CH 2 CH 2 OH, -CH 2 CH (OH) CH 3 , -CH 2 CH 2 CH 2 CH 2 OH, with -CH 2 CH 2 OH being preferred.
  • Examples of C 2 -C 6 polyhydroxyalkyl groups are 2,3-dihydroxypropyl group, 3,4-dihydroxybutyl group, 2,4-dihydroxybutyl group and 1, 2-dihydroxyethyl group.
  • Examples of O-Ce-alkoxy groups are -OCH 3 , -OCH 2 CH 3 , -OCH 2 CH 2 CH 3 , -OCH (CH 3 ) 2 or -OC (CH 3 ) 3 , preferred is the methoxy group (-OCH 3 ).
  • An amino group means a group -NH2.
  • a cyano group means a group -C ⁇ N.
  • Examples of a C 1 -C 6 -alkoxycarbonyl group are a methoxycarbonyl group (H 3 COC (O) -) an ethoxycarbonyl group, an n-propoxycarbonyl group.
  • the phenyl group is a preferred example of an aryl group.
  • Examples of halogen are fluorine, chlorine, bromine or iodine. Preferred halogen atoms are fluorine, chlorine and bromine.
  • oxidation dye precursors of the formulas (I) in which R 1, R 2 and R 5 independently of one another represent hydrogen, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkoxy group or a halogen atom (fluorine, chlorine, bromine or iodine) are preferred, because with these oxidation dyes particularly intense dyeings could be obtained.
  • the radicals R 1, R 2 and R 5 independently of one another represent a hydrogen atom or a C 1 -C 6 -alkyl group. From the group of the C1-C6-alkyl groups in turn, the methyl group is very particularly preferred.
  • an agent according to the invention is therefore characterized in that it contains at least one oxidation dye precursor of the formula (I) in which R 1, R 2 and R 5 independently of one another represent hydrogen or a C 1 -C 6 -alkyl group.
  • oxidation dye precursors of the formula (I) are used, in which R3 and R4 independently of one another for a hydrogen atom, a Ci-C6-alkyl group, a hydroxy group, a Ci-C6-alkoxy group, an amino group or a Nitro devis stand.
  • R 3 and R 4 independently of one another represent a hydrogen atom, a C 1 -C 6 -alkyl group, an amino group or a nitro group.
  • an agent according to the invention is therefore characterized in that it contains at least one oxidation dye precursor of the formula (I) in which R3 and R4 independently of one another represent hydrogen, a C 1 -C 6 -alkyl group, an amino group or a nitro group.
  • the substituent X may represent an oxygen atom (-O-), a sulfur atom (-S-) or a group -NR8-.
  • the substituent X Via the substituent X, the two aromatic systems of the oxidation dye precursors of the formula (I) are linked together.
  • the substituent X is an electron-rich heteroatom (with free electron pairs), which activates the two aromatic systems, so that both ring systems are capable of reacting with further oxidation dye precursors.
  • the group X also influences the absorption properties of the dye formed during the oxidative dyeing process.
  • R8 is preferably a hydrogen atom for steric reasons. It has been found to be particularly preferable if X represents an oxygen atom (-O-) or a group -NR8-, where R8 represents a hydrogen atom.
  • an agent according to the invention is therefore characterized in that it contains at least one oxidation dye precursor of the formula (I) in which X is an oxygen atom (-O-) or a group -NR8-, where R8 is a Hydrogen atom is.
  • the radicals Y1 and Y2 independently of one another may be a group R6R7N-, a hydroxy group, a C 1 -C 6 -alkyl group or a cyano group.
  • the proviso is that at least one of the radicals from the group Y1 and Y2 is a group R6R7N-, since the presence of at least one group R6R7N- in the coupler structures of the formula (I) has proven to be a prerequisite for a sufficiently intense color result.
  • the radicals R 6 and R 7 can in turn be selected independently of one another from a hydrogen atom, a C 1 -C 6 -alkyl group, a C 2 -C 6 -alkenyl group, a hydroxy-C 2 -C 6 -alkyl group, a polyhydroxy-C 2 -C 6 -alkyl group or an aryl group.
  • the radicals R6 and R7 are both a hydrogen atom, in this case, the group R6R7N- is an amino group.
  • oxidation dye precursors of the formula (I) are used in which radicals Y1 and / or Y2 stand for an amino group.
  • a further particularly preferred embodiment is accordingly characterized in that the agent according to the invention comprises at least one oxidation dye precursor of the formula (I) in which Y1 is an amino group and / or Y2 is an amino group.
  • an agent according to the invention is characterized in that it comprises at least one oxidation dye precursor of the formula (I) in which Y1 is an amino group and Y2 is an amino group.
  • an agent according to the invention is characterized in that it comprises at least one oxidation dye precursor of the formula (I) in which Y1 is an amino group or Y2 is an amino group.
  • the dyeing and fastness properties of the oxidation dye precursors of the formula (I) according to the invention are particularly good if one of the two radicals from the group Y1 and Y2 is an amino group and the other of the two radicals is a hydroxy group.
  • the agent according to the invention contains at least one oxidation dye precursor of the formula (I) in which
  • - Y1 is a hydroxy group and Y2 is an amino group or
  • - Y1 is an amino group and Y2 is a hydroxy group.
  • the oxidation dye precursors of the formula (I) are therefore very particularly preferred in which R 1 is a hydrogen atom or a methyl group, R 2 is a hydrogen atom or a methyl group, R 3 is a hydrogen atom, R 4 represents a hydrogen atom, a methyl group, an amino group or a nitro group and R 5 represents a hydrogen atom or a methyl group.
  • agents according to the invention comprise at least one oxidation dye precursor of the formula (I) in which
  • R1 represents a hydrogen atom or a methyl group
  • R2 is a hydrogen atom or a methyl group
  • - R3 is a hydrogen atom
  • R4 represents a hydrogen atom, a methyl group, an amino group or a nitro group
  • R5 represents a hydrogen atom or a methyl group.
  • a further particularly preferred embodiment is accordingly characterized in that the agent according to the invention contains at least one oxidation dye precursor of the formula (I) in which
  • an agent according to the invention is characterized in that it comprises at least one oxidation dye precursor of the formula (I) which is selected from
  • the oxidation dye precursors (A) of the formula (I) according to the invention are amino compounds. These can also be used in the form of their physiologically tolerated salts, in particular the chlorides, the sulfates and bromides. Further preferred salts are derived from sulfonic acids, such as benzenesulfonates, p-toluenesulfone sulfonates, C 1 -C 4 -alkanesulfonates or trifluoromethanesulfonates. Depending on the number of amino groups present in the compounds according to the invention, mono-, di-, tri-, tetra- and higher adducts may be present as salts.
  • physiologically acceptable salts of the oxidation dye precursors (A) of the formula (I) are in particular the hydrochlorides, the hydrobromides and the sulfates of these compounds.
  • the oxidation dye precursor or products (A) of the formula (I) can be used in the compositions according to the invention in a total amount of from 0.001 to 5.0% by weight, preferably from 0.1 to 4.5% by weight, more preferably from 0 From 2 to 4.0% by weight, and more preferably from 0.3 to 3.5% by weight, based on the total weight of the composition.
  • an agent according to the invention is therefore characterized in that it comprises (A) one or more oxidation dye precursors of the formula (I) in a total amount of from 0.001 to 5.0% by weight, preferably from 0.1 to 4, 5 wt .-%, more preferably from 0.2 to 4.0 wt .-% and particularly preferably from 0.3 to 3.5 wt .-% - based on the total weight of the composition - contains.
  • the oxidation dye precursors of formula (I) are coupler type compounds.
  • the compositions according to the invention therefore preferably comprise at least one further oxidation dye precursor of the developer type (numbered as oxidation dye precursors from group (B).
  • Preferred further developer components are selected 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) -propan-2-ol, N, N'-bis (4-
  • Particularly preferred additional developer components are p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1H - Imidazol-1 -yl) propyl] amine and / or 4,5-diamino-1 - (2-hydroxyethyl) pyrazole and their physiologically acceptable salts.
  • the physiologically acceptable salts of the oxidation dye precursors of the developer type from group (B) are in particular the hydrochlorides, hydrobromides and sulfates of these compounds.
  • the oxidation dyes of the formula (I) react with the developers (B) from the group consisting of p-phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, N, N-bis (2) hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1H-imidazol-1-yl) propyl] amine, bis (2 -hydroxy-5-aminophenyl) methane, 4-aminophenol, 4-amino-3-methylphenol, 4,5-diamino-1- (2-hydroxyethyl) pyrazole, 2,4,5,6-t
  • an agent according to the invention is therefore characterized in that it additionally contains (B) one or more oxidation dye precursors from the group formed from p-phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) -p phenylenediamine, N, N-bis- (2-hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1H-imidazole) 1 -yl) propyl] amine, bis (2-hydroxy-5-aminophenyl) methane, 4-aminophenol, 4-amino-3-methylphenol, 4,5-diamino-1- (2-hydroxyethyl) pyrazole, 2 , 4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,
  • the agents according to the invention may contain the developer component (s) from group (B) in a total amount of from 0.001 to 5.0% by weight, preferably from 0.1 to 4.5% by weight, more preferably from 0.2 to 4.0 wt .-% and particularly preferably from 0.3 to 3.5 wt .-% - based on the total weight of the composition - included.
  • an agent according to the invention is therefore characterized in that it contains one or more oxidation dye precursors from group (B) in a total amount of from 0.001 to 5.0% by weight, preferably from 0.1 to 4.5% by weight .-%, more preferably from 0.2 to 4.0 wt .-% and particularly preferably from 0.3 to 3.5 wt .-% - based on the total weight of the composition - contains.
  • compositions of the invention may additionally contain other coupler-type oxidation dyes other than the compounds of formula (I).
  • Coupler components do not form a significant color within the framework of the oxidative dyeing alone, but always require the presence of developer components. Coupler components permit at least one substitution of a chemical residue of the coupler by the oxidized form of the developer component. Covalent bonds form between coupler and developer components.
  • o-aminophenol derivatives such as o-aminophenol
  • Naphthalene derivatives having at least one hydroxy group having at least one hydroxy group
  • Pyrazolone derivatives such as 1-phenyl-3-methylpyrazol-5-one,
  • Morpholine derivatives such as, for example, 6-hydroxybenzomorpholine or 6-aminobenzomorpholine,
  • couplers from the group (C) together with the oxidation dye precursors (A) of the formula (I) and the developers from the group (B) form very intense colors, therefore, preferred are the couplers (C) 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- 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-methylbenz
  • an agent according to the invention is therefore characterized in that it additionally contains (C) one or more oxidation dye precursors from the group which is 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-hydroxyethoxyethyl)
  • the agents according to the invention may in principle contain one or more coupler components from group (C) in a total amount of from 0.001 to 10.0% by weight, based on the total weight of the composition.
  • the coupler (s) from the group (C) is preferably in the total amount of from 0.001 to 5.0% by weight, preferably from 0.025 to 4.5% by weight, more preferably from 0.05 to 4 , 0 wt .-% and particularly preferably from 0, 1 to 3.5 wt .-% - based on the total weight of the composition - included.
  • an agent according to the invention is therefore characterized in that it contains one or more oxidation dye precursors from group (C) in a total amount of from 0.001 to 5.0% by weight, preferably from 0.025 to 4.5% by weight. %, more preferably from 0.05 to 4.0 wt .-% and particularly preferably from 0, 1 to 3.5 wt .-% - based on the total weight of the composition - contains.
  • All of the abovementioned quantities for the total amount of the oxidation dye precursors (A) of the formula (I) in the composition according to the invention relate to the total weight of the compounds of the formula (I) in the color cream, i. in the storage stable formulation prior to preparation of the application mixture and prior to mixing with a second, oxidant-containing component.
  • All of the abovementioned quantities for the total amount of the oxidation dye precursors (B) in the composition according to the invention relate to their total weight in the color cream, i. in the storage stable formulation prior to preparation of the application mixture and prior to mixing with a second, oxidant-containing component.
  • All of the abovementioned quantities for the total amount of the oxidation dye precursors (C) in the composition according to the invention relate to their total weight in the color cream, i. in the storage stable formulation prior to preparation of the application mixture and prior to mixing with a second, oxidizing agent-containing component.
  • the agents according to the invention may additionally contain at least one substantive dye. These are dyes that raise directly on the hair and no need oxidative process to form the paint. Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones, triarylmethane dyes or indophenols.
  • the substantive dyes are each preferably used in an amount of 0.001 to 20 wt .-%, in particular from 0.05 to 5 wt .-%, each based on the total application preparation.
  • the total amount of substantive dyes is preferably at most 3% by weight.
  • Direct dyes may be subdivided into anionic, cationic and nonionic substantive dyes which are selected and used by those skilled in the art according to the requirements of the carrier base.
  • Preferred anionic substantive dyes are those having the international designations or trade names bromophenol blue, tetrabromophenol blue, Acid Yellow 1, Yellow 10, Acid Yellow 23, Acid Yellow 36, Acid Orange 7, Acid Red 33, Acid Red 52, Pigment Red 57: 1, Acid Blue 7, Acid Green 50, Acid Violet 43, Acid Black 1 and Acid Black 52 known compounds.
  • Preferred cationic substantive dyes are Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14, Basic Yellow 57, Basic Red 76, Basic Blue 16, Basic Blue 347 (Cationic Blue 347 / Dystar), HC Blue No. 16, Basic Brown 16, Basic Brown 16, Basic Brown 17, Yellow 87, Basic Orange 31 and Basic Red 51.
  • Suitable nonionic substantive dyes are in particular nonionic nitro and quinone dyes and neutral azo dyes.
  • Preferred nonionic substantive dyes are those under the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, HC Orange 1, Disperse Orange 3, HC Red 1, HC Red 3, HC Red 10, HC Red 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 known compounds , and 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-a
  • the agents according to the invention may also contain naturally-analogous dyes in addition to the compound or compounds of the formula (I).
  • Compositions according to the invention which comprise precursors of naturally-analogous dyes are preferably used as air-oxidative colorants. Consequently, in this embodiment said compositions are not added with an additional oxidizing agent.
  • Particularly suitable precursors of naturally-analogous hair dyes are derivatives of 5,6-dihydroxyindoline, in particular 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5 , 6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and also 5,6-dihydroxy-indoline-2-carboxylic acid, and also derivatives of 5,6-dihydroxyindole, in particular 5,6-dihydroxyindole, N-methyl- 5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, and physiologically acceptable salts the above compounds.
  • the dye precursors of naturally-analogous dyes are each preferably used in an amount of from 0.001 to 5% by weight, based on the total application preparation.
  • the development of the color can in principle be done with atmospheric oxygen.
  • a chemical oxidizing agent is used, especially if, in addition to the coloring, a lightening effect on human hair is desired. This lightening effect may be desired regardless of the staining method.
  • the oxidizing agent are persulfates, peroxodisulfates, chlorites, hypochlorites and in particular hydrogen peroxide and / or one of its solid addition products of organic or inorganic compounds in question.
  • oxidation dye precursors and oxidizing agents themselves are expediently prepared separately from each other and brought into contact only immediately before use.
  • agents are preferred which are characterized in that they are prepared immediately before use by mixing at least two preparations, wherein the at least two preparations are provided in at least two separately prepared containers and wherein a container is a colorant (K1) which contains in a cosmetic carrier at least one oxidation dye precursor (A) according to formula (I), and a further container contains an oxidizing agent preparation (K2) containing at least one oxidizing agent.
  • products containing the agents according to the invention are accordingly packaged as multicomponent packaging units (kit-of-parts) containing
  • K1 a first component which is a previously described inventive agent (containing at least one oxidation dye precursor (A) according to formula (I)) and K2: a second component which is an oxidizing agent preparation. Shortly before use, K1 and K2 are mixed together to form the ready-to-use colorant.
  • the agents (K1) and (K2) can be mixed together, for example, in a mixing ratio of 1: 4 to 4: 1.
  • mixing ratios of 1: 2 to 2: 1 are usual, the mixing ratios in each case referring to the ratio of the amounts by weight of (K1) and (K2) (eg 200 g of the agent (K1) can be mixed with 100 g of the agent (K2). to be mixed this results in a mixing ratio of 2: 1).
  • the oxidizing agent preparation (K2) preferably contains as the oxidizing agent hydrogen peroxide and / or one of its solid addition products of organic or inorganic compounds, such as urea, melamine and sodium borate.
  • the amount of oxidizing agent in the ready-to-use agent is preferably from 0.5 to 12% by weight, preferably from 2 to 10% by weight, more preferably from 3 to 6% by weight (calculated as 100% strength H.sub.2 O.sub.2), based in each case on ready to use means.
  • Such oxidizer formulations are preferably aqueous, flowable oxidizer formulations.
  • Preferred preparations are characterized in that the flowable oxidizing agent preparation - based on their weight - 40 to 90 wt .-%, preferably 50 to 85 wt .-%, particularly preferably 55 to 80 wt .-%, more preferably 60 to 77, 5 wt .-% and in particular 65 to 75 wt .-% water.
  • the oxidation dye can also be applied to the hair together with a catalyst which activates the oxidation of the dye precursors.
  • a catalyst which activates the oxidation of the dye precursors.
  • Such catalysts are z.
  • the ready-to-use oxidative colorant is preferably adjusted to an alkaline pH.
  • the dyeing processes on keratin fibers also usually take place in an alkaline medium.
  • the pH of the ready-to-use agent is from 8.0 to 10.5, more preferably from 8.7 to 10.3, even more preferably from 9.0 to 10.2, and most preferably from 9.2 to 10.1.
  • the pH values given are values measured at a temperature of 22 ° C with a glass electrode.
  • the alkalizing agents which can be used according to 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, (earth) Alkali metal phosphates and (earth) alkali metal hydrogen phosphates.
  • Preferred inorganic alkalizing agents are 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 or the alkalizing agents are compounded together with the oxidation dye precursors in the dyeing preparation (K1).
  • the dyeing preparation (K1) and / or the oxidizing agent preparation (K2) may additionally be added with at least one SiC compound, such as silicic acid or silicates, in particular waterglasses.
  • the SiO 2 compound may in this case be present in the dyeing preparation (K1) and / or in the oxidizing agent preparation (K2).
  • the SiC compounds in amounts of 0.05 wt .-% to 15% by weight, more preferably in amounts of 0, 15 wt .-% to 10 wt .-% and most preferably in Amounts of 0.2 wt .-% to 5 wt .-%, in each case based on the total weight of the dyeing preparation (K1) or on the total weight of the oxidizing agent preparation (K2) to use.
  • the oxidative color-changing agents i.e., the coloring preparation (K1) and / or the oxidizing agent preparation (K2)
  • the ready-to-use 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 anionic, zwitterionic, amphoteric and nonionic surfactants and emulsifiers selected.
  • Agents suitable according to the invention are characterized in that the agent additionally contains at least one anionic surfactant.
  • Preferred anionic surfactants are fatty acids, alkyl sulfates, alkyl ether sulfates and ether carboxylic acids having 10 to 20 carbon atoms in the alkyl group and up to 16 glycol ether groups in the molecule.
  • Agents suitable according to the invention are characterized in that the agent additionally contains at least one zwitterionic surfactant.
  • Preferred zwitterionic surfactants are betaines, N-alkyl- ⁇ , ⁇ -dimethylammonium glycinates, N-acyl-aminopropyl-N, N-dimethylammoniumglycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazoline.
  • 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-alkyl propionic 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, as Kokosacylaminoethylaminopropionat and Ci2-Ci8-Acylsarcosin.
  • the agents contain other, nonionic surfactants.
  • Preferred nonionic surfactants are alkyl polyglycosides and alkylene oxide adducts of fatty alcohols and fatty acids with in each case 2 to 30 moles 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 ready-to-use color-change agents may also contain at least one thickener.
  • thickeners there are no fundamental restrictions. Both organic and purely inorganic thickening agents can be used. Suitable thickeners are anionic, synthetic polymers, cationic, synthetic polymers, naturally occurring thickeners, such as nonionic guar gums, scleroglucan gums or xanthan gums, gum arabic, ghatti gum, karaya gum, tragacanth gum, carrageenan gum, agar agar, Locust bean gum, pectins, alginates, starch fractions and derivatives such as amylose, amylopectin and dextrins, as well as cellulose derivatives such as methylcellulose, carboxyalkylcelluloses and hydroxyalkylcelluloses, nonionic fully synthetic polymers such as polyvinyl alcohol or polyvinylpyrrolidinone; and inorganic thickening agents, in particular phyllosilicate
  • the colorants in particular if they additionally contain hydrogen peroxide, contain at least one stabilizer or complexing agent.
  • Particularly preferred stabilizers are phenacetin, alkali benzoates (sodium benzoate) and salicylic acid.
  • all complexing agents of the prior art can be used.
  • Preferred complexing agents according to the invention are nitrogen-containing polycarboxylic acids, in particular EDTA and EDDS, and phosphonates, in particular 1-hydroxyethane-1, 1-diphosphonate (HEDP) and / or ethylenediamine tetramethylenephosphonate (EDTMP) and / or diethylenetriaminepentamethylenephosphonate (DTPMP) or their sodium salts.
  • the agents according to the invention may contain further 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, especially polysiloxanes with organofunctional groups, such as substituted or unsubstituted amines (amodimethicones), carboxyl, alkoxy and / or hydroxyl groups (dimethicone copolyols), linear polysiloxane (A) polyoxyalkylene (B) block copolymers
  • the choice of these other substances will be made by those skilled in the art according to the desired properties of the agents.
  • additional active ingredients and auxiliaries are preferably present 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 in each case on the total weight of the dyeing preparation (K1) and / or the oxidizing agent preparation (K2) used.
  • the oxidation dye precursors (A) of the formula (I) can be dyed in particular with one or more oxidation dye precursors of the developer type (from the aforementioned group (B)) on keratinic fibers.
  • the dyeings obtained in this way are characterized by a very good perspiration fastness.
  • a further subject of the present invention is therefore the use of an oxidation dye precursor of the formula (I) in the dyeing of keratinic fibers to produce dyeings having improved perspiration fastness,
  • Y1, Y2 independently of one another represent a group R6R7N-, a hydroxy group, a C 1 -C 6 -alkyl group or a cyano group,
  • X represents an oxygen atom (-O-), a sulfur atom (-S-) or a
  • R 1, R 2, R 5 independently represent a hydrogen atom, a C 1 -C 6 -alkyl group, a C 2 -C 6 -alkenyl group, a hydroxy-C 2 -C 6 -alkyl group, a polyhydroxy-C 2 -C 6 -alkyl group, a hydroxy group, a C 1 -C 6 Alkoxy group, a cyano group, a C 1 -C 6 -alkoxycarbonyl group, a nitro group, an aryl group or a halogen atom (fluorine, chlorine, bromine or iodine),
  • R3, R4 independently of one another represent a hydrogen atom, a C 1 -C 6 -alkyl group, a C 2 -C 6 -alkenyl group, a hydroxy-C 2 -C 6 -alkyl group, a polyhydroxy-C 2 -C 6 -alkyl group, a hydroxy group, a C 1 -C 6 -alkoxy group , an amino group, a group R 9 R 10 N-, a cyano group, a C 1 -C 6 -alkoxycarbonyl group, a nitro group, an aryl group or a halogen atom (fluorine, chlorine, bromine or iodine),
  • R 6, R 7, R 8, R 9, R 10 independently of one another represent a hydrogen atom, a C 1 -C 6 -alkyl group, a C 2 -C 6 -alkenyl group, a hydroxy-C 2 -C 6 -alkyl group, a polyhydroxy-C 2 -C 6 -alkyl group or an aryl group,
  • 3-Fluoroaniline (50.0 g, 0.45 mol) was initially charged at room temperature and acetic anhydride (15.0 ml, 1.04 mol, 2.3 eq.) Were slowly added dropwise with stirring, so that the temperature did not exceed 50 ° C. After completion of the addition, the mixture was stirred for 3 h at 50 ° C and the mixture was then poured onto ice-water. The precipitate was filtered off and washed with water. After drying, 3-fluoroacetanilide (53.1 g, 0.35 mol, 77%) was obtained as a white solid.
  • 3-fluoroacetanilide (53.0 g, 0.35 mol) was dissolved in conc. Sulfuric acid (175.0 ml) at 0 - 5 ° C dissolved. With stirring, a solution of nitrating acid (175.0 ml of concentrated sulfuric acid and 28.0 ml of concentrated nitric acid) was slowly added dropwise so that the temperature did not exceed 5 ° C. After the addition was stirred for 2 h at 5 ° C and the mixture was then poured onto ice water. The mixture was extracted with ethyl acetate and the organic phase was concentrated. The residue was half-concentrated in 500 ml.
  • N- (3-Fluoro-4-methylphenyl) acetamide (22.0 g, 0.13 mol) was dissolved in conc. Sulfuric acid (125.0 ml) at 0 - 5 ° C dissolved. With stirring, 1.0 ml of conc. Sulfuric acid slowly added dropwise so that the temperature did not exceed 5 ° C. After completion of the addition, stirring was continued overnight at room temperature and the mixture was subsequently poured into ice-water. The precipitate was filtered off and washed with water. The residue was semi-concentrated in 150 ml. Hydrochloric acid heated for 5 h at reflux, neutralized after cooling with sodium hydroxide solution and the mixture extracted with ethyl acetate. The combined organic phases were concentrated to give 5-fluoro-4-methyl-2-nitroaniline as a white solid (4.7 g, 0.03 mol, 21%).
  • Coupler component 3 mmol
  • Ci6-i8 fatty alcohol (INCI name: Cetearyl alcohol) (Cognis)
  • Ci2-i8 fatty alcohol (INCI name: Coconut alcohol) (Cognis)
  • the dyeing cream thus obtained was mixed in a ratio of 1: 1 with the following developer dispersion having a hydrogen peroxide content of 6%.
  • K1 colorations with 4-N- (3-aminophenyl) benzene-1, 2,4-triamine trihydrochloride (K1)

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Abstract

L'invention concerne des moyens de modification, par oxydation, de la couleur de fibres kératiniques, en particulier des cheveux des hommes. Lesdits moyens contiennent, dans un support cosmétique (A), au moins un produit précurseur de colorants d'oxydation de la formule (I) et/ou un sel physiologiquement acceptable de ce dernier, dans laquelle formule : Y1, Y2 représentent indépendamment l'un de l'autre un groupe R6R7N-, un groupe hydroxy, un groupe alkyle en C1-C6 ou un groupe cyano ; X représente un atome d'oxygène (-O-), un atome de soufre (-S-) ou un groupe -NR8- ; R1, R2, R5 représentent indépendamment les uns des autres un atome d'hydrogène, un groupe alkyle en C1-C6, un groupe alcényle en C2-C6, un groupe alkyle hydroxy en C2-C6, un groupe alkyle polyhydroxy en C2-C6, un groupe hydroxy, un groupe alcoxy en C1-C6, un groupe cyano, un groupe carbonyle alcoxy en C1-C6, un groupe nitro, un groupe aryle ou un atome d'halogène (fluor, chlore, brome ou iode) ; R3 et R4 représentent indépendamment l'un de l'autre un atome d'hydrogène, un groupe alkyle en C1-C6, un groupe alcényle en C2-C6, un groupe alkyl hydroxy en C2-C6, un groupe alkyl polyhydroxy en C2-C6, un groupe hydroxy, un groupe alcoxy en C1-C6, un groupe amino, un groupe R9R10N-, un groupe cyano, un groupe carbonyle alcoxy en C1-C6, un groupe nitro, un groupe aryle ou un atome d'halogène (fluor, chlore, brome ou iode) ; R6, R7, R8, R9, R10 représentent indépendamment les uns des autres un atome d'hydrogène, un groupe alkyle en C1-C6, un groupe alcényle en C2-C6, un groupe alkyle hydroxy en C2-C6, un groupe alkyle polyhydroxy en C2-C6 ou un groupe aryle à la condition qu'au moins un des radicaux issus du groupe Y1 et Y2 représente un groupe R6R7N-.
PCT/EP2015/064414 2014-08-06 2015-06-25 Produit précurseur de colorants d'oxydation WO2016020112A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999011231A1 (fr) * 1997-09-01 1999-03-11 L'oreal Composition pour la teinture d'oxydation des fibres keratiniques
WO2001003651A2 (fr) * 1999-07-13 2001-01-18 Henkel Kommanditgesellschaft Auf Aktien Substance destinee a la teinture de fibres keratiniques
WO2006099115A2 (fr) * 2005-03-11 2006-09-21 The Procter & Gamble Company Nouvelles compositions de coloration capillaire destinees a etre utilisees en colorations pour cheveux oxydatives
WO2012146530A1 (fr) * 2011-04-29 2012-11-01 L'oreal Composition de coloration utilisant un coupleur dérivé de méta-aminophénol dans un milieu riche en substances grasses, procédés et dispositifs

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999011231A1 (fr) * 1997-09-01 1999-03-11 L'oreal Composition pour la teinture d'oxydation des fibres keratiniques
WO2001003651A2 (fr) * 1999-07-13 2001-01-18 Henkel Kommanditgesellschaft Auf Aktien Substance destinee a la teinture de fibres keratiniques
WO2006099115A2 (fr) * 2005-03-11 2006-09-21 The Procter & Gamble Company Nouvelles compositions de coloration capillaire destinees a etre utilisees en colorations pour cheveux oxydatives
WO2012146530A1 (fr) * 2011-04-29 2012-11-01 L'oreal Composition de coloration utilisant un coupleur dérivé de méta-aminophénol dans un milieu riche en substances grasses, procédés et dispositifs

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