WO2009103798A1 - Sels de 9- [4- (amino)phényl] -acridinium utilisés comme colorants directs cationiques pour colorer des fibres contenant de la kératine - Google Patents

Sels de 9- [4- (amino)phényl] -acridinium utilisés comme colorants directs cationiques pour colorer des fibres contenant de la kératine Download PDF

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Publication number
WO2009103798A1
WO2009103798A1 PCT/EP2009/052060 EP2009052060W WO2009103798A1 WO 2009103798 A1 WO2009103798 A1 WO 2009103798A1 EP 2009052060 W EP2009052060 W EP 2009052060W WO 2009103798 A1 WO2009103798 A1 WO 2009103798A1
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group
phenyl
salts
acridinium
hydroxyethyl
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PCT/EP2009/052060
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German (de)
English (en)
Inventor
Wibke Gross
Ralph Nemitz
Denise Fuhr
Anja Reichert
Astrid Kleen
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Henkel Ag & Co. Kgaa
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Priority to EP09712165A priority Critical patent/EP2245013A1/fr
Publication of WO2009103798A1 publication Critical patent/WO2009103798A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B15/00—Acridine dyes

Definitions

  • the invention relates to novel cationic dyes and agents for dyeing and optionally simultaneous lightening of keratin-containing fibers, in particular human hair, which contain these dyes, the use of these cationic dyes for dyeing
  • keratin-containing fibers For the dyeing of keratin-containing fibers are generally either substantive
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • the developer components are usually primary aromatic amines having a further, in the para or ortho position free or substituted hydroxy or amino group,
  • Diaminopyridine derivatives 1,3-bis(trimethyl)-2-aminopyrazolone derivatives
  • 2,4,5,6 2-aminopyrazolone-2-aminopyridine derivatives
  • m-phenylenediamine derivatives naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives are generally used.
  • Suitable coupler substances are in particular ⁇ -naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4 -Diaminophenoxyethanol, 2-amino-4- (2-hydroxyethylamino) -anisole (Lehmann's Blue), 1-phenyl-3-methyl-pyrazol-5-one, 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, 3-amino-6-methoxy-2-methylamino pyridine and 3,5-diamino-2,6-dimethoxypyridine.
  • oxidation dyes Although intensive dyeings having good fastness properties can be obtained with oxidation dyes, the development of the color generally takes place under the influence of oxidizing agents, such as, for example. H 2 O 2 , which in some cases may result in damage to the fiber. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors can sometimes sensitize people with sensitive skin. Direct dyes are applied under gentler conditions, you Disadvantage lies in the fact that the dyeings often have only insufficient fastness properties.
  • the object of the present invention is to provide colorants for keratin-containing fibers, in particular human hair, which are at least equivalent in terms of color depth and fastness properties, such as light fastness, rubfastness and washfastness, as well as perspiration and cold wave fastness, to the usual oxidation hair colorants
  • colorants for keratin-containing fibers, in particular human hair
  • fastness properties such as light fastness, rubfastness and washfastness, as well as perspiration and cold wave fastness
  • B. H 2 O 2 instructed to be.
  • direct drawers should have sufficient stability against H 2 O 2 and not lose their positive fastness and dyeing properties.
  • the colorants must have no or only a very low sensitizing potential and may under no circumstances be mutagenic.
  • as bright and intense colors as possible should be achieved.
  • the present invention relates, in a first embodiment, to agents for dyeing and, if appropriate, simultaneous lightening of keratin fibers, in particular human hair, comprising at least one cationic compound of the formula (Ia):
  • R 1 in the R 1, R 2, R 3, R 4 independently represent a hydrogen atom, a C 1 -C 6 - alkyl group, a C 2 -C e alkenyl group, a Ci-C ⁇ -hydroxyalkyl group, a C 2 -C 6 - Polyhydroxyalkyl group, a halogen atom, a carboxyl group, a nitrile group, a carbamoyl group, a sulfonamido group, a carboxamido group, an alkyloxycarbonyl group or a sulfonic acid group, wherein the two radicals R 1 and R 2 or R 3 and R 4 together form another fused, carbocyclic or heterocyclic ring may optionally bear a substituent R 12 ,
  • R 5 is a C 1 -C 6 -alkyl group, a C 2 -C 6 -alkenyl group, a C 2 -C 6 -
  • Hydroxyalkyl group a C 2 -C 6 polyhydroxyalkyl group, a C 1 -C 6 - alkoxy-C r C 6 alkyl group, an amino-Ci-C 6 alkyl group, a di-C 1 -C 6 - alkylamino-C 2 C 6 alkyl group, a cyano-dC 6 alkyl group or a substituent of the formulas II to VII:
  • R 6 and R 7 independently represent a hydrogen atom, a C 1 -C 6 - alkyl group, a C 2 -C e alkenyl group, a C-
  • R 8 and R 9 independently of one another represent a substituent which is defined as R 5 or together form a 5-, 6- or 7-membered ring which may optionally carry further substituents or heteroatoms,
  • R 10 and R 11 independently represent a hydrogen atom, a Ci-C 6 - alkyl group, a Ci-C 6 hydroxyalkyl group, a C 2 -C 6 - polyhydroxyalkyl group, a C 2 -C 6 alkenyl group, an aryl group or a heteroaryl
  • R 12 is a hydrogen atom, a C T -C ⁇ -alkyl group, a C 2 -C 6 -
  • Alkenyl group a C 1 -C 6 hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a halogen atom, a carboxyl group, a nitrile group, a carbamoyl group, a sulfonamido group, a carboxamido group, an alkyloxycarbonyl group or a sulfonic acid group and
  • X- is a monovalent anion, preferably a halide (chloride, bromide, iodide or fluoride), hydrogen sulfate, V 2 sulfate, V 2 tetrachlorozincate, p- benzenesulfonate, p-toluenesulfonate, acetate, tetrafluoroborate, trifluoromethanesulfonate, hexafluorophosphate, methane sulfate or methanesulfonate , Keratin fibers are wool, furs, feathers and especially human hair to understand.
  • the colorants of the invention can in principle but also for dyeing other natural fibers such.
  • keratin fibers As cotton, jute, sisal, linen or silk, modified natural fibers such. As regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose can be used.
  • the term "dyeing of keratin fibers" used according to the invention encompasses any form of color change of the fibers. In particular, the color changes encompassed by the terms tinting, bleaching, oxidative dyeing, semi-permanent dyeing, permanent dyeing and temporary dyeing are included.
  • Examples of (C 1 to C 6 ) -alkyl radicals are the groups methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl and tert-butyl, n-pentyl and n-hexyl.
  • Propyl, ethyl and methyl are preferred alkyl radicals.
  • Examples of corresponding cyclic alkyl groups are cyclopentyl and cyclohexyl.
  • Examples of preferred (C 2 to C 6 ) alkenyl radicals are vinyl and allyl.
  • a (C 1 to C 6 ) -Monohydroxyalkyl a hydroxymethyl, a 2-hydroxyethyl, a 2-hydroxy propyl, a 3-hydroxypropyl, a 4-hydroxybutyl group, a 5-Hydroxypentyl- and a 6-hydroxyethyl group may be mentioned.
  • a 2-hydroxyethyl group is particularly preferred.
  • Examples of a (C 2 to C 6 ) -polyhydroxyalkyl group are the 2,3-dihydroxypropyl group, 3,4-
  • Preferred (C 1 to C 6 ) alkoxy groups according to the invention are, for example, a methoxy or an ethoxy group.
  • Methoxyhexyl group are examples of inventive (C 1 to C 6 ) alkoxy (C 2 to C 6 ) - alkyl groups.
  • a preferred hydroxy (C 1 -C 6 ) -alkoxy group is the 2-hydroxyethoxy group.
  • halogen atoms are F, Cl, Br or I atoms, with Br or Cl atoms being very particularly preferred
  • aminomethyl 2-aminoethyl, 3-aminopropyl, 2-dimethylaminoethyl, diethylaminomethyl,
  • Dimethylaminoethyl, dimethylamino and the amino group are particularly preferred.
  • Preferred aryl (C 1 -C 3) -alkyl groups are benzyl and 2-phenylethyl.
  • radical R5 is a dC 6 alkyl group
  • radicals R6 and R7 independently of one another represent a hydrogen atom, a
  • R6 and R7 are each a hydrogen atom.
  • radicals R8 and R9 are independently a dC 6 alkyl group, a C 2 -C e alkenyl group or a C 2 -C 6 -
  • R8 and R9 independently of one another for a
  • Methyl group an allyl group or a 2-hydroxyethyl group. Furthermore, it is preferred according to the invention if R 8 and R 9 are identical substituents or together form a 5-, 6- or 7-membered ring, which may optionally be further
  • R 8 and R 9 are a 2-hydroxyethyl group.
  • the direct dyes it is in particular very particularly preferred in which represent R1, R2, R3 and R4 is a hydrogen atom, the radical R 5 is a C- ⁇ -C6 alkyl group or a C 2 -C 6 - represents alkenyl, it is at residues R6 and R7 independently is a hydrogen atom, a hydroxy group, a halogen atom (especially chloride or bromide) or an alkoxy group and the radicals R8 and R9 are independently a C 1 -C 6 - alkyl group, a C 2 -C 6 alkenyl group, or a C 2 -C 6 hydroxyalkyl group, or when R 8 and R 9 together form a 5-, 6- or 7-membered ring which may optionally carry further substituents or heteroatoms.
  • R1, R2, R3 and R4 represent a hydrogen atom
  • the radical R5 represents a methyl group or an allyl group
  • the radicals R6 and R7 independently of one another are a hydrogen atom, a hydroxy group Is halogen atom (in particular chloride or bromide) or a methoxy group
  • the radicals R 8 and R 9 are, independently of one another, a methyl group, an ethyl group, an allyl group or a 2-hydroxyethyl group, or together with the nitrogen atom which carries them, a piperidine ring, a morpholine ring, form a piperazine ring or a pyrrolidine ring.
  • compositions according to the invention for dyeing and, if appropriate, simultaneous lightening of keratinic fibers comprise at least one cationic compound from the group of
  • the salts of 9- ⁇ 4- [bis (2-hydroxyethyl) amino] phenyl ⁇ -10-methylacridinium, especially 9- ⁇ 4- [bis (2-hydroxyethyl) amino] phenyl ⁇ -10-methylacridinium-p -toluenesulfonate, the 9- ⁇ 4- [bis (2-hydroxyethyl) amino] phenyl ⁇ -10-methylacrylonidinium bromide, the 9- ⁇ 4- [bis (2-hydroxyethyl) amino] - phenyl ⁇ -10-methylacridinium chloride and the the 9- ⁇ 4- [bis (2-hydroxyethyl) amino] phenyl ⁇ -10-methylacridinium acetate are very particularly preferred direct drawers according to the invention.
  • compositions according to the invention containing the salts disclosed therein are also particularly preferred.
  • the compositions according to the invention for dyeing and, if appropriate, simultaneous brightening of keratin fibers preferably contain the compound (s) of the formula (Ia) in amounts above 1 ppm and below 10% by weight, in each case based on the total agent.
  • Preferred agents according to the invention for dyeing and optionally simultaneously lightening keratinic fibers are characterized in that they contain the compound (s) of the formula (Ia) in amounts of from 0.001 to 5% by weight, preferably from 0.0025 to 2.5% by weight. %, more preferably from 0.005 to 1, 5 wt .-% and in particular from 0.01 to 1 wt .-%, each based on the total agent.
  • the agents according to the invention serve to change the color of keratinic fibers, in particular human hair.
  • the color change can be effected solely on the basis of the cationic compound (s) of the formula (Ia), but the agents according to the invention can also additionally contain further color-modifying substances, for example substantive dyes and / or oxidation dyes.
  • Compositions according to the invention for dyeing and, if appropriate, simultaneous lightening of keratinic fibers which additionally contain, based on their weight, from 0.001 to 5% by weight of one or more oxidation dye precursors and / or direct dyes, are preferred.
  • 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 one another or with coupling with one or more coupler components.
  • the oxidation dyes are characterized by excellent, long-lasting dyeing results. For naturally acting dyeings but usually a mixture of a larger number of oxidation dye precursors must be used; In many cases, direct dyes are still used for shading.
  • the developer components are usually primary aromatic amines having a further, in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5, 6- tetraaminopyrimidine and its derivatives used.
  • Very particularly preferred developer components are selected from at least one compound from the group formed from p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ⁇ -dihydroxyethyl) -p phenylenediamine, N, N-bis ( ⁇ -hydroxyethyl) -p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1 H -imidazol-1-yl) propyl] amine, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4-aminophenyl) -1, 3-diamino-propan-2-ol, 2-methoxymethyl-p-phenylenediamine, bis (2 -hydroxy-5-aminophenyl) -methane, 1, 3-bis (2,5-diaminophenoxy) -propan-2
  • Coupler components do not form a significant color within the framework of the oxidative dyeing alone, but always require the presence of developer components. Therefore, it is preferred according to the invention that at least one coupler component is additionally used when using at least one developer component. Coupler components according to the invention allow 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.
  • coupler components according to the invention are selected from m-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- (diethylamino) -phenol, N-cyclopentyl-3-aminophenol, 1, 3-dihydroxy-5- (methylamino) -benzene, 3-ethylamino-4-methylphenol, 2,4- Dichloro-3-aminophenol, 2- (2,4-diaminophenoxy) ethanol, 1, 3-bis (2,4-diaminophenoxy)
  • the coupler components are preferably used in an amount of 0.005 to 20 wt .-%, preferably 0.1 to 5 wt .-%, each based on the ready oxidation dye.
  • 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.
  • dyeing or tinting agents which contain as coloring component so-called direct drawers. These are dye molecules that attach directly to the substrate and do not require 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 rapid undesirable change in shade or even a visible, homogeneous color loss occurs much faster.
  • compositions according to the invention may contain at least one further substantive dye.
  • these are dyes that raise directly on the hair and do not require an oxidative process to form the color.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • the substantive dyes are each preferably used in an amount of 0.001 to 20 wt .-%, based on the total application 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 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. Preferred cationic substantive dyes are included
  • 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 (C) substantive dyes containing a heterocycle having at least one quaternary nitrogen atom, as mentioned for example in EP-A2-998 908, to which reference is explicitly made at this point in claims 6 to 11 are called.
  • the compounds known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51 are very particularly preferred cationic substantive dyes of group (c).
  • the cationic direct dyes which are sold under the trademark Arianor ®, according to the invention are also very particularly preferred cationic direct 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 HC Red 11, HC Red 11, HC Red 11, HC Blue 11, HC Blue 2, HC Blue 11, HC Blue 12, Disperse Blue 3, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9 well-known compounds, as well 1,4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis (2-hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- (2-hydroxyethyl) ammophenol, 2- (2-hydroxyethyl) amino-4,6-dinitrophenol, 4 - [(2-hydroxyethyl) amino] -3-nitro-1-methylbenzene, 1-amino-4- (2-hydroxyethyl) amino-5- chloro-2-nitrobenzene, 4-amino-3-nitro
  • the substantive dyes each represent uniform compounds. Rather, due to the production process for the individual dyes, minor amounts of other components may be included, as far as these do not adversely affect the dyeing result or for other reasons, e.g. toxicological, must be excluded.
  • 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.
  • precursors of the natural hair dye melanin are applied to the substrate, eg hair; These then form naturally-analogous dyes in the course of oxidative processes in the hair.
  • multiple use of agents with 5,6-dihydroxyindoline it is possible to reproduce natural hair color to people with graying hair.
  • the dyeing can be done with atmospheric oxygen as the sole oxidant, so that no further oxidizing agent must be used. In individuals with originally medium blond to brown hair, the indoline can be used as the sole dye precursor.
  • a first class of oxo dye precursors are compounds having at least one reactive carbonyl group. This first class is called a component (Oxo1).
  • a second class of oxo dye precursors form CH-acidic compounds and compounds having primary or secondary amino groups or hydroxy groups, which in turn are selected from compounds of the group formed from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds and aromatic hydroxy compounds. 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 dyes in a non-oxidative process of so-called oxo dyeing. The resulting dyeings have partially color fastness on the keratin-containing fiber, which are comparable to those of the oxidation dyeing
  • the Nuancenspektrum achievable with the gentle oxo staining is very broad and the color obtained often has an acceptable brilliance and color depth.
  • the oxo staining method can be readily combined with the oxidative staining system.
  • Oxofarbstoffvor pas is preferably a combination of at least one compound containing at least one reactive carbonyl group (component (oxo 1)) with at least one compound (component Oxo2)
  • (Oxo2b) Compounds having primary or secondary amino group or hydroxy group selected from at least one compound of the group formed from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds and aromatic hydroxy compounds.
  • 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 carry at least one formyl group and / or at least one keto group, in particular at least one formyl group.
  • those compounds according to the invention are also suitable 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 with respect to the component (Oxo2) is always present.
  • component (Oxo1) is preferably addition compounds a) of amines and their derivatives to form imines or oximes as addition compound b) of alcohols to form acetals or ketals as addition compound c) of water to form hydrates as addition compound (component (Oxo1) is derived in in this case c) from an aldehyde) to the carbon atom of the carbonyl group of the reactive carbonyl compound.
  • Very particularly preferred reactive carbonyl compounds according to the invention are selected from 4-hydroxy-2-methoxybenzaldehyde, 2-chloro-3,4-dihydroxybenzaldehyde, 2-bromo-3,4-dihydroxybenzaldehyde, 3,4-dihydroxy-5-methoxybenzaldehyde, 2,3 Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde and 2,4-dimethoxybenzaldehyde.
  • CH-acidic compounds according to the invention are selected from the physiologically acceptable salts of 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium and of 1,2-dihydro-1,3-one , 4,6-tetramethyl-2-oxo-pyrimidonium and 2- (cyanomethyl) -benzimidazole.
  • component (Oxo2b) at least one oxidation dye precursor having at least one primary or secondary amino group and / or at least one hydroxyl group can be used. Preferred suitable representatives are found under the execution of the oxidation dye precursors.
  • the compounds of the component (oxo2) are selected only among CH-acidic compounds.
  • 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 according to the invention additionally preferably comprise hydrogen peroxide.
  • agents according to the invention for dyeing and, if appropriate, simultaneous lightening of keratinic fibers are particularly preferred, which contain 0.5 to 15% by weight, preferably 1 to 12.5% by weight, particularly preferably 2.5 to 10% by weight and in particular 3 to 6 wt .-% hydrogen peroxide (calculated as 100% H 2 O 2) included.
  • the hydrogen peroxide may also be used in the form of its attachment compounds to solid supports, preferably hydrogen peroxide itself is 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, for example, sodium perborate, Sodium percarbonate, magnesium percarbonate, sodium percarbamide, polyvinylpyrrolidone n H 2 O 2 (Ii is a positive integer greater than 0), urea peroxide and melamine peroxide used.
  • very particularly preferred according to the invention are aqueous hydrogen peroxide solutions.
  • the concentration of a hydrogen peroxide solution is determined on the one hand by the legal requirements and on the other hand by the desired effect; preferably 6 to 12 percent solutions in water are used.
  • At least one bleach booster is preferably used in the cosmetic compositions according to the invention.
  • Bleach boosters are preferably used to increase the bleaching action of the oxidizing agent, in particular the hydrogen peroxide.
  • Suitable bleach boosters are (BV-i) compounds which, under perhydrolysis conditions, give aliphatic peroxycarboxylic acids and / or optionally substituted perbenzoic acid, and / or
  • Bleach boosters are preferably peroxo compounds, in particular inorganic peroxo compounds.
  • the bleach-enhancing peroxy compounds according to the invention there are no addition products of hydrogen peroxide to other components and also not hydrogen peroxide itself.
  • the choice of peroxo compounds is subject to no restrictions.
  • Preferred peroxy compounds are peroxydisulfate salts, persulfate salts, peroxydiphosphate salts (especially ammonium peroxydisulfate, potassium peroxodisulfate, sodium peroxydisulfate, ammonium persulfate, potassium persulfate, sodium persulfate, potassium peroxydiphosphate) and peroxides (such as barium peroxide and magnesium peroxide).
  • the peroxydisulfates in particular ammonium peroxydisulfate
  • the bleach boosters are in the cosmetic compositions according to the invention preferably in amounts of 5 to 30 wt .-%, in particular in amounts of 8 to 20 wt .-%, each based on the
  • Weight of ready to use agent included.
  • the colorant according to the invention contains at least one care substance.
  • the color-modifying agent according to the invention contains as care substance at least one cationic surfactant.
  • Preference according to the invention is given to cationic surfactants of the quaternary ammonium type, which
  • Preferred quaternary ammonium compounds are cetyltrimethylammonium chloride and stearyltrimethylammonium chloride
  • Preferred ester quats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
  • cationic surfactants suitable according to the invention are those under the INCI names
  • the cationic surfactants are contained in the compositions according to the invention preferably in amounts of 0.05 to 10 wt .-%, based on the total application preparation. Amounts of 0.1 to 5 wt .-% are particularly preferred.
  • the color-modifying agents contain as care substance at least one nourishing polymer.
  • a first group of caring polymers are the cationic polymers.
  • Cationic polymers are polymers according to the invention which have a group in the main and / or side chain which may be “temporary” or “permanent” cationic.
  • “permanently cationic” refers to those polymers which have a cationic group independently of the pH of the agent These are generally polymers which contain a quaternary nitrogen atom, for example in the form of an ammonium group
  • Preferred cationic groups are quaternary ammonium groups
  • those polymers in which the quaternary ammonium group is bonded to a polymer main chain composed of acrylic acid, methacrylic acid or derivatives thereof via a C 1-4 hydrocarbon group have been found to be particularly suitable.
  • Particularly suitable cationic polymers are the optionally crosslinked homopolymers and copolymers of methacryloyloxyethyltrimethylammonium chloride.
  • the homopolymer bears the INCI name Polyquaternium-37.
  • Corresponding copolymers preferably contain acrylamide, methacrylamide, acrylic acid as nonionogenic monomer units. 4- alkyl esters and methacrylic acid-C- M- alkyl esters Among these non-ionic monomers, the acrylamide is particularly preferred.
  • These copolymers can also be crosslinked, as described above in the case of the homopolymers.
  • quaternized cellulose derivatives such as are available under the names of Celquat ® and Polymer JR ® commercially.
  • the compounds Celquat ® H 100, Celquat ® L 200 and Polymer JR ⁇ 400 are preferred quaternized cellulose derivatives, cationic alkyl polyglycosides according to DE-PS 44 13 686, cationized honey, for example the commercial product Honeyquat ® 50, cationic guar derivatives, such as in particular the products sold under the trade names Cosmedia® ® guar and Jaguar ® products,
  • Polysiloxanes having quaternary groups such as the commercially available products Q2-7224 (manufactured by Dow Corning, a stabilized trimethylsilylamide dimethicone), Dow Corning® 929 emulsion (containing a hydroxylamino-modified silicone, also referred to as amodimethicones), SM -2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and AbiP-Quat 3270 and 3272 (manufacturer: Th.
  • Q2-7224 manufactured by Dow Corning, a stabilized trimethylsilylamide dimethicone
  • Dow Corning® 929 emulsion containing a hydroxylamino-modified silicone, also referred to as amodimethicones
  • SM -2059 manufactured by General Electric
  • SLM-55067 manufactured by Wacker
  • AbiP-Quat 3270 and 3272 manufactured by Th.
  • Such compounds are sold under the names Gafquat ® 734 and Gafquat ® 755 commercially,
  • Vinylpyrrolidone-vinyl imidazolium copolymers such as those offered under the names Luviquat ® FC 370, FC 550, FC 905 and HM 552, quaternized polyvinyl alcohol, as well as by the names of Polyquaternium 2, Polyquaternium 17, Polyquaternium 18 and Polyquaternium 27, having quaternary Nitrogen atoms in the polymer backbone.
  • cationized protein hydrolysates are to be counted among the cationic polymers, wherein the underlying protein hydrolyzate from the animal, for example from collagen, milk or
  • Keratin from the plant, for example, from wheat, corn, rice, potatoes, soy or almonds, marine life forms, such as fish collagen or algae, or biotechnologically derived protein hydrolysates, may originate. Very particular preference is given to the cationic protein hydrolysates and derivatives based on plants.
  • amphoteric polymers are those under the INCI name
  • the color-modifying agents of the invention more preferably contain the cationic polymers
  • the color-modifying agents according to the invention comprise at least one UV filter.
  • Two preferred UV filters with cationic groups are those available as commercial products
  • Cinnamic acid compounds trimethylammonium chloride (lncroquat ® UV-283) and dodecyl tosylate (Escalol ® HP 610).
  • the teaching of the invention also includes the use of a combination of several UV filters.
  • the combination of at least one water-insoluble UV filter with at least one UV filter with a cationic group is preferred.
  • the UV filters are contained in the compositions of the invention usually in amounts of 0.01-5 wt .-%, based on the total application preparation. Amounts of 0.1-2.5 wt .-% are preferred.
  • the color-modifying agents according to the invention contain as care substance at least one vitamin, one provitamin, one
  • Vitamin precursor and one of their derivatives.
  • the color-modifying agents according to the invention preferably contain vitamins, provitamins and
  • Vitamin precursors from groups A, B, C, E and H may be very particularly preferred according to the invention.
  • Panthenol, pantolactone, pyridoxine and its derivatives as well may be very particularly preferred according to the invention.
  • Nicotinic acid amide and biotin are also particularly preferred.
  • the Ganz according to the invention particularly suitable are the extracts of Moringa Olifeira, green tea, almond, aloe vera,
  • the plant extracts can be used according to the invention both in pure and in diluted form. If they are used in diluted form, they usually contain about 2 to 80 wt .-% of active substance and used as solvent in their recovery
  • Extracting agent or extractant mixture may be preferred.
  • the color-modifying agents according to the invention contain as care substance at least one protein hydrolyzate and one of its
  • Animal protein hydrolysates are, for example, elastin, collagen, keratin, silk and milk protein hydrolysates, which may also be present in the form of salts.
  • Such products are, for example, under the trademarks Dehylan ® (Cognis), Promois ® (Interorgana) Collapuron ®
  • Preferred according to the invention is the use of protein hydrolysates of plant origin, eg. B. soy, almond, pea, potato and wheat
  • Such products are, for example, under the trademarks Gluadin ® (Cognis), diamine ® (Diamalt) ® (Inolex),
  • Crotein ® (Croda) available.
  • the protein hydrolysates are in the color-changing agents according to the invention in
  • Wt .-% and most preferably in amounts of 0.05 wt .-% up to 5 wt .-%, each based on the total application preparation included.
  • the color-modifying agents according to the invention contain these active ingredients preferably in amounts of 0.001 to 2, in particular from 0.01 to 0.5 wt .-%, each based on the total
  • the color-changing agents according to the invention contain as care substance at least one monosaccharide or oligosaccharide.
  • the preparations according to the invention contain a heated, that is to say caramelized sugar, preferably caramelized, cane sugar.
  • the mono- or oligosaccharides are contained in the hair treatment compositions according to the invention preferably in an amount of 0.1 to 8 wt .-%, in particular 1 to 5 wt .-%, based on the total application preparation.
  • the inventive preparation contains (B) as
  • Care product at least one silicone oil and / or a silicone gum.
  • suitable silicones or silicone gums are especially dialkyl and
  • Alkylarylsiloxanes such as dimethylpolysiloxane and methylphenyl-polysiloxane, and their alkoxylated, quaternized or anionic derivatives.
  • silicones examples include Oligomeric polydimethylcyclosiloxanes (INCI name: Cyclomethicone), in particular the tetrameric and pentameric compounds sold as commercial products DC 344 and DC 345, respectively, by Dow Corning,
  • Hexamethyl disiloxane (INCI name: Hexamethyldisiloxane), z. B. the product sold under the name Abil ® K 520,
  • Polydimethylsiloxane polymers (INCI name: Dimethicone), z.
  • the products sold under the name DC 200 by Dow Corning polyphenylmethylsiloxanes (INCI name 1 phenyl trimethicone), for example the commercial product DC 556 fluid from Dow Corning,
  • Sihcon glycol copolymers (INCI name: Dimethicone Copolyol), z.
  • esters and partial esters of silicone glycol copolymers such as, for example, by the company Fanning under the trade name LIM Fancorsil ® (INCI name: dimethicone copolyol Meadowfoamate) are distributed,
  • Hydroxy-terminated dimethylsiloxanes e.g. Dow Corning's commercial products DC 1401 and Q2-1403, aminofunctional polydimethylsiloxanes and hydroxylamine-modified silicones (INCI name: Amodimethicone and Quaternium-80), such as the commercial products XF42-B1989 (manufactured by GE Toshiba Silicones) Q2-7224 (manufacturer: Dow Corning, a stabilized trimethylsilylamodimethicone), Dow Corning® 939 emulsion (containing a hydroxylamino-modified silicone, also referred to as amodimethicones), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker), and ABIP-Quat 3270 and 3272 (manufacturer: Th. Goldschmidt), anionic silicone oils, such as the product Dow Corning ® 1784 amino-modified organo
  • the preparations according to the invention preferably contain the silicones in amounts of from 0.01 to 10% by weight, in particular from 0.1 to 5% by weight, based on the total application preparation.
  • the color change agents according to the invention contain at least one oil body and / or a wax as a care substance.
  • the natural and synthetic cosmetic oil bodies include, for example: vegetable oils liquid paraffin oils, isoparaffin oils and synthetic hydrocarbons and di-n-alkyl ethers having a total of between 12 and 36 carbon atoms,
  • Dicarboxylic acid esters symmetrical, unsymmetrical or cyclic esters of carbonic acid with fatty alcohols
  • Fatty acids with glycerine Fatty acid partial glycerides, which are monoglycerides, diglycerides and their technical
  • the amount used of the natural and synthetic cosmetic oil bodies in the color-modifying agents according to the invention is usually 0.1-30% by weight, based on the total application preparation, preferably 0.1-20% by weight, and in particular 0.1-15% by weight. -%.
  • the preparation further contains at least one flavonoid. Very particularly preferred flavonoids according to the invention
  • Tiliroside [(2R, 3R, 4S, 5R, 6S) -6- [5,7-dihydroxy-2- (4-hydroxyphenyl) -4-oxo-chromen-3-yl] oxy-3,4,5 -trihydroxy-oxan-2-yl] methyl (E) -3- (4-hydroxyphenyl) prop-2-enoate; INCI name: Tiliroside, CAS No. 20316-62-5),
  • Rutin sulfate (3,3 ', 4', 4,7-pentahydroxyflavone-3-rhamnoglucoside, INCI name Disodium Rutinyl Disulfate),
  • Troxerutin (2- [3,4-bis (2-hydroxyethoxy) phenyl] -5-hydroxy-7- (2-hydroxyethoxy) -3- [3, 4,5-trihydroxy-6 - [(3,4, 5-trihydroxy-6-methyl-oxan-2-yl) oxymethyl] oxan-2-yl] oxy-chromen-4-one; INCI name: troxerutin, CAS No. 96304-71-1) and
  • isoquercetin (2- (3,4-dihydroxyphenyl) -5,7-dihydroxy-3 [(2S, 3R, 4S, 5R, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) oxan-2-one yl] oxy-chromen-4-one; CAS No. 482-35-9).
  • a very particularly preferred flavonoid according to the invention is tiliroside.
  • the flavonoids of the formula (I) are preferably present in the preparations according to the invention in an amount of from 0.0001 to 5% by weight, in particular from 0.002 to 1% by weight, based in each case on the pure active compound and the entire ready-to-use agent.
  • Particularly preferred care substances in the context of the present invention are, in particular, vitamin C, ubiquinones, panthenol and its derivatives, ectoin, chamomile extract, bisabolol, olive oil, royal jelly, mung bean extract and Moringa Olifeira extract
  • the dyeing and / or brightening agents according to the invention contain nonionic surfactants.
  • nonionic surfactants are the alkoxylated fatty alcohols, the alkoxylated fatty acids and the alkylphenols and alkylphenol alkoxylates.
  • Agents according to the invention which contain non-ionic surface-active substances in amounts of 1 to 5% by weight have proved to be particularly advantageous.
  • the dyeing and / or brightening agents according to the invention may contain all known in such preparations active ingredients, additives and excipients.
  • the agents contain at least one surfactant, in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable.
  • Anionic surfactants may be very particularly preferred.
  • Preferred anionic surfactants are alkyl sulfates, ether carboxylic acid salts having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule such as C 12 H 25 - (C 2 H 4 O) 6 -CH 2 -COONa and in particular salts of saturated and especially unsaturated C8-C22 carboxylic acids such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • anionic surfactants should preferably be present in solid, in particular powder form. Very particular preference is given to solid soaps, especially sodium stearate, at room temperature. These are preferably present in amounts of 5 to 20 wt .-%, in particular 10 to 15 wt .-%, before.
  • Particularly suitable nonionic surfactants are C 8 -C 22 -alkyl mono- and oligoglycosides and their ethoxylated analogs. In particular, the nonethoxylated compounds have been found to be particularly suitable.
  • ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. Cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride and tricetylmethyl ammonium chloride.
  • Further cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • Alkylamidoamines in particular fatty acid amidoamines, such as the stearylamidopropyldimethylamine obtainable under the name Tego Amid® S 18, are distinguished not only by a good conditioning action but also by their good biodegradability. Also very good biodegradability are quaternary Ester für styrene, so-called "esterquats", such as the Distearoylethylhydroxyethylammoniurnmethosulfat available in a blend with Cetearylalkohle under the name Dehyquart® ® F 75 miles.
  • esterquats such as the Distearoylethylhydroxyethylammoniurnmethosulfat available in a blend with Cetearylalkohle under the name Dehyquart® ® F 75 miles.
  • the compounds containing alkyl groups used as surfactants may each be uniform substances. However, it is usually preferred to start from the production of these substances from native plant or animal raw materials, so as to obtain substance mixtures with different, depending on the particular raw material alkyl chain lengths.
  • compositions according to the invention may contain at least one ammonium compound from the group of ammonium chloride, ammonium carbonate, ammonium bicarbonate, ammonium sulfate and / or ammonium carbamate in an amount of from 0.5 to 10, preferably 1 to 5 wt .-%, based on the total composition of the composition.
  • compositions of 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 to be understood as meaning aqueous solutions containing from 3 to 70% by weight of a C 1 -C 4 -alkoxy, in particular ethanol or isopropanol.
  • compositions according to the invention may additionally contain further organic solvents, for example methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. Preference is given to all water-soluble organic solvents.
  • Preferred agents according to the invention are characterized in that they additionally contain a nonaqueous solvent, particularly preferred compositions according to the invention the solvent in a concentration of 0.1 to 30 weight percent, preferably in a concentration of 1 to 20 weight percent, most preferably in a concentration of 2 - 10 weight percent, each based on the agent included.
  • the solvent is selected from ethanol, n-propanol, isoropanol, n-butanol, propylene glycol, n-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, phenoxyethanol and benzyl alcohol and their mixtures.
  • the pH of the compositions according to the invention can be adjusted within a wide range by suitable ingredients such as acidifying agent or alkalizing agent.
  • Oxidative dyeing of the fibers can in principle be carried out with atmospheric oxygen in the presence of oxidation dye precursors.
  • 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. Accordingly, the presence of oxidation dye precursors is not a mandatory requirement for the use of oxidizing agents in the compositions according to the invention.
  • Suitable oxidizing agents are persulfates, chlorites and in particular hydrogen peroxide or its addition products of urea, melamine and sodium borate.
  • the oxidation colorant can also be applied to the hair together with a catalyst which promotes the oxidation of the dye precursors, e.g. by atmospheric oxygen, activated.
  • catalysts are e.g. Metal ions, iodides, quinones or certain enzymes.
  • the actual colorant is expediently immediately before use by mixing the preparation of the oxidizing agent with the preparation containing the compounds of the formula I and, if appropriate, dye precursors, produced.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 12. Particularly preferred is the use of the hair dye in a weakly alkaline medium.
  • the application temperatures can be in a range between 15 and 40 0 C.
  • the hair dye is removed by rinsing of the hair to be dyed. The washing with a shampoo is omitted if a strong surfactant-containing carrier, such as a dyeing shampoo was used.
  • compositions of the invention are mixed immediately before application with a hydrogen peroxide solution.
  • concentration of this hydrogen peroxide solution is determined on the one hand by the legal requirements and on the other hand by the desired effect; As a rule, 6-12% solutions in water are used.
  • the proportions of dyeing and / or lightening agent and hydrogen peroxide solution are usually in the range 1: 1 to 1: 2, with an excess of hydrogen peroxide solution is particularly selected when no too pronounced Blondier Stil is desired.
  • Complex images are substances that can complex metal ions.
  • Preferred complexing agents are so-called chelate complexing agents, ie substances which form cyclic compounds with metal ions, a single ligand occupying more than one coordination site on a central atom, i. H. at least "bidentate".
  • chelate complexing agents ie substances which form cyclic compounds with metal ions, a single ligand occupying more than one coordination site on a central atom, i. H. at least "bidentate”.
  • normally stretched compounds are closed by complex formation via an ion into rings.
  • the number of bound ligands depends on the coordination number of the central ion.
  • chelating agents from the groups of (i) polycarboxylic acids in which the sum of the carboxyl and optionally
  • Hydroxyl groups is at least 5, (ii) nitrogen-containing mono- or polycarboxylic acids, (iii) geminal diphosphonic acids, (iv) aminophosphonic acids, (v) phosphonopolycarboxylic acids, (vi) cyclodextrins.
  • a preferred class of substances with complex-forming properties are the phosphonates. These are, in particular, hydroxyalkane or aminoalkanephosphonates. Among the hydroxyalkanephosphonates, 1-hydroxyethane-1,1-diphosphonate (HEDP) is of particular importance. It is preferably used as the sodium salt, the disodium salt neutral and the tetrasodium salt alkaline (pH 9).
  • Preferred aminoalkane phosphonates are ethylenediamine tetramethylene phosphonate (EDTMP), diethylene pentamine methylene phosphonate (DTPMP) and their higher homologs. They are preferably used in the form of the neutrally reacting sodium salts, eg. B.
  • the complexing agent used here is preferably HEDP from the class of phosphonates.
  • the aminoalkanephosphonates also have a pronounced heavy metal binding capacity. Accordingly, in particular if the agents also contain bleach, it may be preferable to use aminoalkanephosphonates, in particular DTPMP, or to use mixtures of the phosphonates mentioned. These substances will be described below.
  • phosphonates preferably hydroxyalkane or aminoalkane phosphonates and in particular 1-hydroxyethane-1,1-diphosphonate (HEDP) or its di- or tetrasodium salt and / or ethylenediamine tetramethylene phosphonate (EDTMP) or its hexasodium salt and / or diethylene triamine pentamethylene phosphonate (DTPMP ) or its hepta- or octasodium salt.
  • HEDP 1-hydroxyethane-1,1-diphosphonate
  • ETMP ethylenediamine tetramethylene phosphonate
  • DTPMP diethylene triamine pentamethylene phosphonate
  • Particularly preferred agents according to the invention contain one or more substances from the group
  • NTA nitrilotriacetic acid
  • EDDG ethylenediamine-N-N'-diglutaric acid
  • a second subject of the present invention is a process for dyeing and possibly simultaneously brightening keratin fibers, in particular human hair, in which, if desired, a pretreatment agent M1 is applied to the fiber, then an agent M2 on the fiber is used, if desired the agent M2 the application is added a further agent M3, this agent M2 is rinsed off the fiber after a period of 5-30 minutes and after the treatment optionally an aftertreatment agent M4 is applied to the fiber and rinsed off after a contact time of a few minutes, wherein at least one of the agents M1, M2 or M3 a means according to the invention.
  • the agents according to the invention can accordingly be formulated as single-component agents (dyeing and whitening agents M2 or aftertreatment agents M4), as two-component agents (M2 + M3) or as three-component agents (M2 + M3 + M4) and used accordingly. Separation into multicomponent systems is particularly suitable where incompatibilities of the ingredients are to be expected or feared; the agent to be used in such systems is manufactured by the consumer just prior to use by mixing the component.
  • a dyeing and whitening process in which the whitening cream and the oxidizing agent are initially separate is preferred.
  • a further subject of the present invention is therefore a process for dyeing and lightening human hair, in which an aqueous-based composition containing hydrogen peroxide is mixed with an agent according to the invention to form a homogeneous composition and applied to the hair.
  • the aqueous-based composition contains 1 to 20% by weight, preferably 2 to 10% by weight and in particular 3 to 6% by weight of hydrogen peroxide, calculated as 100% H 2, by weight O 2 .
  • Further preferred processes according to the invention of this type are characterized in that the aqueous-based composition containing hydrogen peroxide with an agent according to the invention in a weight ratio of 1: 5 to 10: 1, preferably 1.2 to 5: 1 and especially 1: 2 to 2: 1 a homogeneous composition, and this is applied to the hair.
  • a further subject of the present invention is therefore a process for dyeing and lightening human hair which comprises an aqueous-based composition containing hydrogen peroxide with a further agent containing preferably at least one alkalinity donor and / or substantive hair dye and / or at least one oxidation dye precursor, and a composition according to the invention mixed to a homogeneous composition, and this is applied to the hair.
  • a further subject of the present invention is therefore the use of cationic compounds of the formula (Ia):
  • R 1, R 2, R 3, R 4 independently represent a hydrogen atom, a C 1 -C 6 - alkyl group, a C 2 -C 6 alkenyl group, a C-
  • R 5 stands for a C
  • Hydroxyalkyl group a C 2 -C 6 polyhydroxyalkyl group, a C 1 -C 6 - alkoxy-CrC 6 alkyl group, an amino-Ci-C 6 alkyl group, a di-C 1 -C 6 - alkylamino-C 2 -C 6- alkyl group, a cyano-d-C ⁇ -alkyl group or a substituent of the formulas II to VII. 1
  • R 6 and R 7 independently represent a hydrogen atom, a Ci-C 6 - alkyl group, a C 2 -C 6 alkenyl group, a Ci-C 6 hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a halogen atom (chloride , bromide, iodide or fluoride), a carboxyl group, a nitrile group, a carbamoyl group, a sulfonamido group, a carboxamido group, a Alkyloxycarbonylguppe, a sulfonic acid group, a Ci-C 6 - alkoxy group, a hydroxy group, an amino group or a C 1 -C 6 - dialkylamino
  • R 8 and R 9 independently of one another represent a substituent which is defined as R 5 or together form a 5-, 6- or 7-membered ring which may optionally carry further substituents or heteroatoms,
  • R 10 and R 11 independently represent a hydrogen atom, a CrC 6 - alkyl group, a C- ⁇ -C 6 hydroxyalkyl group, a C 2 -C 6 - polyhydroxyalkyl group, a C 2 -C e alkenyl group, an aryl group or a heteroaryl
  • R 12 represents a hydrogen atom, a dC 6 alkyl group, a C 2 -C 6 -
  • Alkenyl group a C 1 -C 6 hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a halogen atom, a carboxyl group, a nitrile group, a carbamoyl group, a sulfonamido group, a carboxamido group, an alkyloxycarbonyl group or a sulfonic acid group and
  • X is a monovalent anion, preferably halide (chloride,
  • the mutated mutandis applies to the preferred agents.
  • R 1 ', R 2 ', R 3 ', R 4 stand for a hydrogen atom
  • R 5 ' represents allyl group or a 2-hydroxyethyl group
  • R 6 'and R 7' are each independently a hydrogen atom, a C 1 -C 6 - alkyl group, a C 2 -C ⁇ alkenyl group, a Ci-C ⁇ -hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a halogen atom ( Chloride, bromide, iodide or fluoride), carboxyl group, nitrile group, carbamoyl group, sulfonamido group, carboxamido group, alkyloxycarbonyl group, sulfonic acid group, C 1 -C 6 alkoxy group, hydroxy group, amino group or C 1 -C 6 - dialkylamino group,
  • R 8 'and R 9 ' independently of one another represent a substituent which is defined as R 5 or together form a 5-, 6- or 7-membered ring which may optionally carry further substituents or heteroatoms,
  • X " is a monovalent anion, preferably halide (chloride,
  • R 1 ', R 2', R 3 ', R 4 independently represent a hydrogen atom, a C 1 -C 6 - alkyl group, a C 2 -C 6 alkenyl group, a Ci-C 6 hydroxyalkyl group, a C 2 C 6 polyhydroxyalkyl group, a halogen atom, a carboxyl group, a nitrile group, a carbamoyl group, a sulfonamido group, a carboxamido group, an alkyloxycarbonyl group or a sulfonic acid group, where the two radicals R 1 and R 2 or R 3 and R 4 together form a further fused, may form a carbocyclic or heterocyclic ring optionally bearing a substituent R 10 ',
  • R 5 ' represents a -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 -
  • Hydroxyalkyl group a C 2 -C 6 polyhydroxyalkyl group, a C 1 -C 6 - alkoxy-CrC 6 alkyl group, an amino-Ci-C 6 alkyl group, a di-C 1 -C 6 - alkylamino-C 2 -C 6- alkyl group, a cyano-d-C ⁇ -alkyl group
  • R 6 'and R 7' are each independently a hydrogen atom, a C 1 -C 6 - alkyl group, a C 2 -C 6 alkenyl group, a dC 6 hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a halogen atom ( Chloride, bromide, iodide or fluoride), carboxyl group, nitrile group, carbamoyl group, sulfonamido group, carboxamido group, alkyloxycarbonyl group, sulfonic acid group, C 1 -C 6 alkoxy group, hydroxy group, amino group or C 1 -C 6 - dialkylamino group,
  • R 8 'and R 9 ' together form a 5-, 6- or 7-membered ring which may optionally carry further substituents or heteroatoms,
  • R 10 stands for a hydrogen atom, a dC 6 alkyl group, a C 2 -C 6 -
  • Alkenyl group a C 1 -C 6 hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a halogen atom, a carboxyl group, a nitrile group, a carbamoyl group, a sulfonamido group, a carboxamido group, an alkyloxycarbonyl group or a sulfonic acid group and
  • X " is a monovalent anion, preferably halide (chloride,
  • Particularly preferred cationic compounds according to the invention are selected from the group of
  • Particularly preferred cationic compounds according to the invention are 10-allyl-9- [4- (dimethylamino) phenyl] acridinium bromide, 10-allyl-9- [4-
  • the 9- ⁇ 4- [bis (2-hydroxyethyl) amino] phenyl ⁇ -10-methylacridinium p-toluenesulfonate, the, 9- ⁇ 4- [bis (2-hydroxyethyl) amino] phenyl ⁇ -10-methylacridinium bromide, the 9- ⁇ 4- [bis (2-hydroxyethyl) amino] phenyl ⁇ -10-methylacridinium chloride and the 9- ⁇ 4- [bis (2-hydroxyethyl) amino] phenyl ⁇ -10-methylacr ⁇ dinium Acetate are very particularly preferred according to the invention.
  • the oil was separated from the rest of the reaction and dissolved in 500 ml of dichloromethane.
  • the organic phase was washed with water until the water phase was only slightly colored. Then the organic phase was dried with magnesium sulfate and concentrated in a rotary evaporator to give a dark blue powder.
  • the first nine components were melted together at 80 ° C., after which the dye was added. This mixture was emulsified with a solution of the ammonium sulfate in 30 g of water. Subsequently, a swelling of 1, 0 g Natrosol ® 250 HR in 15.0 g of water was added. The pH stated in Table 2 was adjusted with 0.1% sodium hydroxide solution, then made up to 100 g with water.
  • the Stenol ® 16/18 was melted together with Eumulgin ® B1 and Dehyquart ® A-CA, the melt was then emulsified with hot water. Then, the dye and the aqueous ammonium sulfate solution were added. The pH was with ammonia bwz. Citric acid was adjusted to the value given in the table, then it was made up to 100 g with water. 2.1 .3 Anionic coloring cream
  • Lorol ® (techn.) 5.0 g
  • the first 8 components were melted together at 80 0 C, then 1, 2-propanediol and the Schwarzzieher were added with stirring.
  • the following 3 components were dissolved or suspended in one part of the water and also added to the base. With water was made up to about 95 g, the pH stated in the table was adjusted with citric acid or 0.1 percent sodium hydroxide solution. It was then made up to 100 g with stirring with stirring.
  • Carbopol ® Ultrez 10 polyacrylate (INCI name: Carbomer) (Lubrizol) Cetiol ® HE Coconut monoglyceride with approx. 7.3 EO units (INCI name: PEG-7 Glyceryl Cocoate) (Cognis)
  • Dow Corning ® 580 Wax mixture of stearoxytrimethylsilane and stearyl alcohol about 40% stearyl alcohol, INCI name: stearoxytrimethylsilane, stearyl alcohol) (Dow Corning)
  • Eumulgin ® B2 Cetylstearylalkohol with about 20 EO units (INCI name: Ceteareth-20): ((Cognis) Eumulgin ® 05 oleyl-cetyl alcohol with about 5 EO units from plants (oleth-5 INCI name) Cognis) Eumulgin ® RH 40 hardened castor oil with approx. 40 EO units (INCI name: PEG-40 Hydrogenated Castor OiI) (Cognis)
  • Hydrenol ® DC 16 -i 8 fatty alcohol (INCI name: Cetearyl Alcohol) (Cognis) Lorol (techn.f C 12-i 8 fatty alcohol (INCI name: Coconut Alcohol) (Cognis) Natrosol ® 250 HR hydroxyethyl cellulose (INCI Designation: hydroxyethylcellulose) (Hercules)
  • Polydiol ® polyethylene glycol 400 (INCI name: PEG-8) (Cognis) Stenol 1618 ® C 16-i 8 fatty alcohol (INCI name: Cetearyl Alcohol) (Cognis) Texapon ® NSO-UP lauryl ether sulfate, sodium salt (ca. 27 5% active ingredient, INCI name: Sodium Laureth Sulfate) (Cognis)
  • the number of the coloring cream refers in each case to the corresponding subchapter of paragraph 2.1:

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Abstract

La présente invention concerne des composés cationiques de formule (Ia) dans laquelle R1 à R9 et X- sont définis dans la revendication 1, lesquels composés sont conçus pour colorer des fibres de kératine, notamment des cheveux humains, et ne font en partie, en tant que tels, pas encore l'objet d'une invention en l'état de la technique. Les colorations contenant ces composés permettent d'obtenir des nuances de couleur extrêmes et intenses, notamment dans la gamme du bleu et du violet, avec de très bonnes caractéristiques de résistance. Ces colorants directs permettent également d'obtenir des nuances lumineuses, sans atténuation de l'intensité et de la brillance de la couleur, lorsqu'ils sont utilisés conjointement à des agents oxydants tels que de l'eau oxygénée ou un mélange d'eau oxygénée et de peroxydisulfates.
PCT/EP2009/052060 2008-02-22 2009-02-20 Sels de 9- [4- (amino)phényl] -acridinium utilisés comme colorants directs cationiques pour colorer des fibres contenant de la kératine WO2009103798A1 (fr)

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WO2019057451A1 (fr) * 2017-08-29 2019-03-28 Universität Basel Colorants organiques à petites molécules
WO2023197005A3 (fr) * 2022-04-08 2023-11-30 Oregon Health & Science University Inhibiteurs à petites molécules de l'énolase 1 et de l'énolase 3

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EP2609905A1 (fr) 2011-12-29 2013-07-03 KPSS-Kao Professional Salon Services GmbH Composition de teinture capillaire

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013174871A1 (fr) 2012-05-23 2013-11-28 L'oreal Procédé de teinture de fibres kératiniques comprenant une teinture/un pigment, un composé photoactif et une source lumineuse
US9730876B2 (en) 2012-05-23 2017-08-15 L'oreal Process for dyeing keratin fibres comprising a dye-pigment, a photoactive compound and a light source
WO2019057451A1 (fr) * 2017-08-29 2019-03-28 Universität Basel Colorants organiques à petites molécules
CN111315829A (zh) * 2017-08-29 2020-06-19 巴塞尔大学 小分子有机染料
US11214687B2 (en) 2017-08-29 2022-01-04 Universität Basel Small-molecule organic dyes
CN111315829B (zh) * 2017-08-29 2022-11-04 巴塞尔大学 小分子有机染料
WO2023197005A3 (fr) * 2022-04-08 2023-11-30 Oregon Health & Science University Inhibiteurs à petites molécules de l'énolase 1 et de l'énolase 3

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DE102009001039A1 (de) 2009-12-03

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