Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
  • C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
  • C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
  • C07C215/80—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring containing at least two amino groups bound to the carbon skeleton

Definitions

• the invention relates to new aminophenol derivatives, their use for dyeing keratin fibers and dyes containing these compounds.
• conventional hair colorants are formulated either on the basis of oxidation dyes or on the basis of substantive dyes. Combinations of oxidation dyes and direct dyes are often used to achieve special shades.
• Good dyes are characterized by high color strength. Good sweat, heat, perm, wash and light fastness are also desired. They should also be safe from a toxicological and dermatological perspective. It is also advantageous if the substances have a high solubility in various base formulations.
• Coloring agents or tinting agents which contain so-called direct draws as the coloring component are usually used for temporary dyeings. These are dye molecules that attach directly to the hair and do not require an oxidative process to form the color. These dyes include, for example, henna, which is known from antiquity for coloring body and hair. These dyeings are generally significantly more sensitive to shampooing than the oxidative dyeings, so that a much undesired shift in nuances or even a visible "discoloration” occurs much more quickly. So-called oxidation colorants are used for permanent, intensive dyeings with appropriate fastness properties. 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 atmospheric oxygen with one another or under coupling with one or more coupler components.
• the oxidation colorants are characterized by excellent, long-lasting coloring results.
• a mixture of a larger number of oxidation dye precursors usually has to be used for natural-looking dyeings; in many cases direct dyes are also used for shading.
• a hairstyle usually has hair or hair zones of different ages and degrees of damage.
• One example of this is long hair, in which the hair tips, which have been exposed to all possible environmental influences for a long time, are generally significantly more damaged than the relatively freshly regrown hair zones.
• An oxidation coloring agent is therefore also required to have a high leveling capacity in order to obtain a consistently uniform hair color. There is therefore still a need for new, improved dye components.
• a first subject of the present invention are aminophenol derivatives of the general formula (I) with the substituent X of the general formula (II),
• Examples of the C 1 to C 4 alkyl groups mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl groups, the methyl group is particularly preferred.
• a preferred Cr to C 4 alkoxy group according to the invention is, for example, a methoxy or an ethoxy group. Examples of one are a hydroxymethyl or a hydroxyethyl group. Examples of an alkoxyalkyl group of the general formula -C a H 2a OC b H 2b + ⁇ are a methoxymethyl or a Methoxy ethyl group.
• examples of a halogen atom are an F, a Cl or a Br atom, an F or a Cl atom are particularly preferred.
• physiologically compatible inorganic cations are the cations of sodium, potassium and lithium and the ammonium ion.
• the sodium cation and the ammonium ion are particularly preferred.
• mono-, di- or tri-C-hydroxyalkylammonium is preferred as physiologically compatible organic cations.
• n is a number from 1 to 6 and which have a hydroxyl group on the aliphatic chain, for example a monohydroxypropyl diether group.
• compounds of the formula (I) are preferred in which the two aminophenol nuclei are linked in the ortho position to both OH groups.
• a second subject of the present invention is the use of the aforementioned aminophenol derivatives as developer components in oxidation hair colorants.
• oxidation colorants for dyeing keratin fibers containing coupler components and developer components in a water-containing carrier, which contains one of the aforementioned aminophenol derivatives as developer component.
• Keratin fibers mean furs, wool, feathers and in particular human hair.
• the oxidation colorants according to the invention are primarily suitable for dyeing keratin fibers, there is in principle nothing to prevent their use in other areas, particularly in color photography.
• the oxidation colorants according to the invention contain the developer components according to the invention and, if desired, can also contain further developer components and coupler components.
• Preferred developer components according to the invention are p-phenylenediamine, p-toluenediamine, p-aminophenol, o-aminophenol, 1- ( ⁇ -hydroxyethyl) -2,5-diaminobenzene, N, N-bis ( ⁇ -hydroxyethyl) - p-phenylenediamine, 2- (2 ', 5' -diaminophenoxy) ethanol,
• developer components are p-phenylenediamine, p-tolylene-diamine, p-aminophenol, 1- (2'-hydroxyethyl) -2,5-diaminobenzene, N, N-bis (2-hydroxyethyl) -p-phenylenediamine , 4-amino-3-methylphenol, 4-amino-2 - ((diethylamino) methyl) phenol, 2-aminomethyl-4-aminophenol, 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5 , 6- triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine and 4,5-diamino-l- (2'-hydroxyethyl) pyrazole.
• M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used as coupler components.
• Suitable coupler substances are in particular 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxy naphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, l -Phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1,3-bis (2,4-diaminophenoxy) propane, 2-chloro-resorcinol, 4-chloro-resorcinol , 2-chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol and
• Coupler components preferred according to the invention are m-aminophenol and its derivatives such as 5-amino-2-methylphenol, 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 and 2,4-dichloro-3-aminophenol , o-aminophenol and its derivatives, m-diaminobenzene and its derivatives such as, for example, 2,4-diaminophenoxyethanol
• Di- or trihydroxybenzene derivatives such as resorcinol, resorcinomino methyl ether, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2-chlororesorcinol, 4-chlororesorcinol, pyrogallol and 1, 2,4-trihydroxybenzene, pyridine derivatives such as 2,6 -Dihydroxypyridine, 2-amino-3-hydroxy-pyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxy-pyridine, 2,6-dihydroxy-3,4-dimethylpyridine , 2,6-dihydroxy-4-methylpyridine, 2,6- Diaminopyridine, 2,3-diamino-6-methoxypyridine and 3,5-diamino-2,6-dimethoxypyridine,
• Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1-naphthol, 1, 5-dihydroxynaphthalene, 1,6-
• Morpholine derivatives such as 6-hydroxybenzomorpholine and 6-aminobenzomorpholine,
• Pyrazole derivatives such as, for example, l-phenyl-3-methylpyrazol-5-one,
• Indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and
• Methylenedioxybenzene derivatives such as l-hydroxy-3,4-methylenedioxybenzene, l-amino-3,4-methylenedioxybenzene and l- (2'-hydroxyethyl) amino-3,4-methylenedioxybenzene.
• Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
• Preferred direct dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16 and Basic Brown 17 known compounds as well as 1,4-bis- (ß-hydroxyethyl ) -amino-2-nitrobenzene, 4-amino-2-nitrodiphenylamine-2 '-carboxylic acid, 6-nitro-l, 2,3,4-tetrahydroquinoxaline, hydroxyethyl-2-nitro-toluidine, picramic acid, 2-amino -6-chloro-4-nitrophenol, 4-ethyla
• preparations according to the invention can also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, 3
• Further dye components contained in the colorants according to the invention can also be indoles and indolines, and also their physiologically tolerable salts.
• Preferred examples are 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, 6-hydroxyindole, 6-aminoindole and 4-aminoindole.
• 5,6-dihydroxyindoline N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline , 5, 6-dihydroxyindoline-2-carboxylic acid, 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
• oxidation dye precursors or the substantive dyes each represent uniform compounds. Rather, in the hair colorants according to the invention, due to the production processes for the individual dyes, further components may be present in minor amounts, provided that these do not adversely affect the coloring result or for other reasons, e.g. toxicological, must be excluded.
• the coloring is oxidative, whether with atmospheric oxygen or other oxidizing agents such as hydrogen peroxide, weakly acidic to alkaline, ie adjusted to pH values in the range from about 5 to 11.
• the colorants contain alkalizing agents, usually alkali or alkaline earth metal hydroxides, ammonia or organic amines.
• Preferred alkalizing agents are monoethanolamine, monoisopropanolamine, 2-amino-2-methyl-propanol, 2-amino-2-methyl-l, 3-propanediol, 2-amino-2-ethyl-l, 3-propanediol, 2-amino-2 -methylbutanol and triethanolamine as well as alkali and alkaline earth metal hydroxides.
• Monoethanolamine, triethanolamine and 2-amino-2-methyl-propanol and 2-amino-2-methyl-1,3-propanediol are particularly preferred in this group. It is also possible to use ⁇ -amino acids such as ⁇ -aminocaproic acid as an alkalizing agent.
• oxidizing agents such as, in particular, hydrogen peroxide or its adducts with urea, melamine or sodium borate can be used to form the actual hair colors from the oxidation dye precursors.
• oxidation with atmospheric oxygen as the only oxidizing agent can be preferred. It is also possible to carry out the oxidation with the aid of enzymes, the enzymes being used both for producing oxidizing per compounds and for enhancing the action of a small amount of oxidizing agents present.
• the enzymes (enzyme class 1: oxidoreductases) can transfer electrons from suitable developer components (reducing agents) to atmospheric oxygen.
• Oxidases such as tyrosinase and laccase are preferred, but also glucose oxidase, uricase or pyruvate oxidase. Furthermore, the procedure should be mentioned to increase the effect of small amounts (e.g. 1% and less, based on the total agent) of hydrogen peroxide by peroxidases.
• the preparation of the oxidizing agent is then expediently mixed with the preparation with the dye precursors immediately before dyeing the hair.
• the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 10. It is particularly preferred to use the hair dye in a weakly alkaline environment.
• the application temperatures can be in a range between 15 and 40 ° C., preferably at the temperature of the scalp. After an exposure time of approx. 5 to 45, especially 15 to 30, minutes the hair dye is removed from the hair to be dyed by rinsing. Washing with a shampoo is not necessary if a carrier with a high surfactant content, e.g. B. a coloring shampoo was used.
• the preparation with the dye precursors can be applied to the hair without prior mixing with the oxidation component.
• the oxidation component is then applied, if necessary after an intermediate rinse.
• rinsing is then carried out and, if desired, re-shampooing.
• the corresponding agent is adjusted to a pH of about 4 to 7.
• air oxidation is initially sought, the agent applied preferably having a pH of 7 to 10.
• the use of acidified peroxidisulfate solutions as the oxidizing agent can be preferred.
• the formation of the color can be supported and increased by adding certain metal ions to the agent.
• metal ions are, for example, Zn 2+ , Cu 2+ , Fe + , Fe 3+ , Mn 2+ , Mn 4+ , Li + , Mg 2+ , Ca 2+ and Al.
• Zn, Cu and Mn are particularly suitable.
• the metal ions can be used in the form of any physiologically acceptable salt.
• Preferred salts are the acetates, sulfates, halides, lactates and tartrates.
• the oxidation dye precursors are incorporated into a suitable water-containing carrier.
• suitable water-containing carrier are, for example, creams, emulsions, gels or also surfactant-containing foaming solutions, for example shampoos, aerosols or other preparations which are suitable for use on the hair.
• the colorants according to the invention can furthermore contain all active substances, additives and auxiliaries known for such preparations.
• the colorants contain at least one surfactant, with both anionic and zwitterionic, ampholytic, cationic and surfactants being suitable in principle. In many cases, however, it has proven advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
• Suitable anionic surfactants in agents according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
• the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
• suitable anionic surfactants are, in each case in the form of the sodium, potassium, magnesium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group,
• Ether carboxylic acids of the formula R-O- (CH -CH O) -CH -COOH, in which R is a linear one
• amide ether carboxylates of the formula [R-NH (-CH 2 -CH 2 -O) n -CH 2 -COO] m Z, in which R is for one linear or branched, saturated or unsaturated acyl radical with 2 to 29 C atoms, n for integers from 1 to 10, m for the numbers 1 or 2 and Z for a cation from the group of alkali or alkaline earth metals, acyl sarcosides with 10 up to 18 C atoms in the acyl group, acyl taurides with 10 to 18 C atoms in the acyl group, acyl isethionates with 10 to 18 C atoms in the acyl group,
• Esters of tartaric acid and citric acid with alcohols the addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols with 8 to 22 carbon atoms, coconut monoglyceride sulfates.
• Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and sulfosuccinic acid and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid mono- alkyl polyoxyethyl ester with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups and soaps.
• Non-ionic surfactants contain z.
• B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
• Such connections are, for example
• Preferred nonionic surfactants are alkyl polyglycosides of the general formula RO- (Z). These connections are characterized by the following parameters.
• the alkyl radical R contains 6 to 22 carbon atoms and can be either linear or branched. Primary linear and methyl-branched aliphatic radicals in the 2-position are preferred. Examples of such alkyl radicals are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. 1-Octyl, 1-decyl, 1-lauryl, 1-myristyl are particularly preferred. When using so-called "oxo alcohols" as starting materials, compounds with an odd number of carbon atoms in the alkyl chain predominate.
• the alkyl polyglycosides which can be used according to the invention can contain, for example, only a certain alkyl radical R. Usually, however, these compounds are made from natural fats and oils or mineral oils. In this case, the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the respective working up of these compounds.
• Alkylpolyglycosides in which R consists essentially of C o - and C 1 u -alkyl groups, essentially of C - and C -alkyl groups, essentially of C 8 - to C, 16 -alkyl groups or essentially of C - are particularly preferred. to C alkyl groups.
• Any mono- or oligosaccharides can be used as sugar building block Z.
• Sugar with 5 or 6 carbon atoms and the corresponding oligosaccharides are usually used.
• sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, old rose, mannose, gulose, idose, talose and sucrose.
• Preferred sugar units are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
• the alkyl polyglycosides which can be used according to the invention contain on average 1.1 to 5 sugar units. Alkyl polyglycosides with x values from 1.1 to 1.6 are preferred. Alkyl glycosides in which x is 1.1 to 1.4 are very particularly preferred.
• the alkyl glycosides can also serve to improve the fixation of fragrance components on the hair.
• the person skilled in the art will preferably resort to this substance class as a further ingredient of the preparations according to the invention.
• alkoxylated homologs of the alkyl polyglycosides mentioned can also be used according to the invention. These homologues can contain an average of up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
• zwitterionic surfactants can be used, in particular as co-surfactants.
• Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO - or -SO group in the molecule.
• Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammonium glycinate, the cocoacylaminopropyl-dimethylammonium glycinate, and 2- Alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
• a preferred zwitterionic surfactant is the fatty acid amide derivative known under the INCI name Cocamidopropyl Betaine.
• Ampholytic surfactants are also particularly suitable as co-surfactants.
• Ampholytic surfactants are surface-active compounds which, in addition to a C 18 -C 18 -alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and to form internal salts are qualified.
• ampholytic surfactants are N-alkyl glycine, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
• Particularly preferred ampholytic surfactants are the N-coconut alkyl aminopropionate, the coconut acylaminoethyl aminopropionate and the C 8 -acyl sarcosine.
• cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds, esterquats and amidoamines.
• Preferred quaternary ammonium compounds are ammonium halides, especially chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, and the compounds known under the INCI names Quaternium-27 and Quaternium-83 compounds Imidazol.
• the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
• Ester quats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
• 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.
• Such products are sold, for example, under the trademarks Stepantex ® , Dehyquart ® and Armocare ® .
• the alkylamidoamines are usually produced by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
• An invented 1f dung particularly suitable according to compound from this group is that available under the name Tegoamid ® S 18 commercially stearamidopropyl dimethylamine.
• a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® L00, according to INCI nomenclature a "lauryl methyl Gluceth-lO Hydroxypropyl Dimonium Chloride".
• the compounds with alkyl groups used as surfactant can each be uniform substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with different alkyl chain lengths depending on the respective raw material are obtained.
• both products with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
• “Normal” homolog distribution is understood to mean mixtures of homologs which are obtained as catalysts from the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
• narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
• the oxidation colorants used according to the invention contain a care substance.
• This care substance is preferably selected from the group formed by cationic polymers, silicones and protein hydrolyzates and their derivatives. 1?
• a first group of cationic polymers are the so-called “temporarily cationic” polymers. These polymers usually contain an amino group which is present as a quaternary ammonium group at certain pH values and is therefore cationic.
• the permanent cationic polymers are preferred among the cationic polymers.
• polymers which have a cationic group irrespective of the pH of the agent are referred to as “permanently cationic”. These are generally polymers which contain a quaternary nitrogen atom, for example in the form of an ammonium group.
• Preferred cationic polymers are, for example, quaternized Cellulose derivatives, as are commercially available under the names Celquat ® and Polymer JR ®
• the compounds Celquat ® H 100, Celquat ® L 200 and Polymer JR ® 400 are preferred quaternized cellulose derivatives, polysiloxanes with quaternary groups, for example the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning ® 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (Her adherer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80),
• Cationic guar derivatives such as in particular the products sold under the trade names Cosmedia Guar and Jaguar,
• Polymeric dimethyldiallylammonium salts and their copolymers with esters and amides of acrylic acid and methacrylic acid are examples of such cationic polymers,
• Copolymers of vinylpyrrolidone with quaternized derivatives of dialkylaminoalkyl acrylate and methacrylate such as, for example, vinylpyrrolidone-dimethylaminoethyl methacrylate copolymers quaternized with diethyl sulfate.
• Such compounds are commercially available under the names Gafquat ® 734 and Gafquat ® 755, VinylpyrTolidon-Vinylimidazoliummethochlorid copolymers, as they are offered under the names Luviquat ® FC 370, FC 550, FC 905 and HM 552, quaternized polyvinyl alcohol, as well as the polymers known under the names Polyquaternium 2. Polyquaternium 17, Polyquaternium 18 and Polyquaternium 27 with quaternary nitrogen atoms in the polymer main chain.
• cationic polymers those under the names Polyquaternium-24 (commercial product e.g. Quatrisoft ® LM 200), Polyquaternium-32, Polyquaternium-35 and Polyquaternium-37 (commercial products e.g. Salcare SC 92 and Salcare ® SC 95) known polymers.
• copolymers of vinyl pyrrolidone such as those available as commercial products Copolymer 845 (manufacturer: ISP), Gaffix ® VC 713 (manufacturer: ISP), Gafquat ® ASCP 1011, Gafquat ® HS 110, Luviquat ® 8155 and Luviquat ® MS 370 are.
• Cationic polymers preferred according to the invention are quaternized cellulose derivatives, polymeric dimethyldiallylammonium salts, polyquaternium-27 and their copolymers and also polymers of the polyquaternium-2 type.
• Cationic cellulose derivatives, in particular the commercial product Polymer ® JR 400, and polymers of the type polyquaternium-2, in particular the commercial product Mirapol ® A-15, are very particularly preferred cationic polymers.
• the cationic polymers are contained in the agents used according to the invention preferably in amounts of 0.05 to 10% by weight, based on the total agent. Amounts of 0.1 to 5% by weight are particularly preferred.
• Ampho-polymers are also suitable as a care substance in combination with or as an alternative to cationic polymers.
• amphoteric polymers are amphoteric polymers, i. H. Polymers that contain both free amino groups and free - COOH or SO H groups in the molecule and are capable of forming internal salts,
• amphopolymer suitable is that available under the name Amphomer ® acrylic resin which is a copolymer of tert-butylaminoethyl methacrylate. N- (l, l, 3,3-tetramethylbutyl) acrylamide and two or more monomers from the group consisting of acrylic acid, methacrylic acid and their simple esters. Also preferred amphopolymers are composed of unsaturated carboxylic acids (e.g. acrylic and methacrylic acid), cationically derivatized unsaturated carboxylic acids (e.g.
• acrylic amidopropyl trimethyl ammonium chloride and optionally other ionic or nonionic monomers, such as the German published application 39 29 973 and the state of the art cited therein.
• Care substances which can be used according to the invention are furthermore silicone oils and silicone gums, in particular dialkyl- and alkylarylsiloxanes, such as, for example, dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated and quaternized analogs.
• silicone oils and silicone gums in particular dialkyl- and alkylarylsiloxanes, such as, for example, dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated and quaternized analogs.
• silicones examples include the products sold by Dow Coming under the names DC 190, DC 200 and DC 1401 and the commercial products DC 344 and DC 345 from Dow Coming, Q2-7224 (manufacturer: Dow Coming; a stabilized trimethylsilylamodimethicone), Dow Corning ® 929 emulsion (containing a hydroxylamino-modified silicone, which is also known as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80) and the commercial product Fancorsil ® LIM-1.
• a suitable anionic silicone oil is the product Dow Corning ® 1784.
• Protein hydrolyzates are product mixtures that are obtained by acidic, basic or enzymatically catalyzed breakdown of proteins (proteins). According to the invention, protein hydrolyzates of both vegetable and animal origin can be used.
• Animal protein hydrolyzates are, for example, elastin, collagen, keratin, silk and milk protein protein hydrolyzates. which can also be in the form of salts.
• Such products are, for example, under the trademarks Dehylan ® (Henkel), Promois ® (Interorgana), Collapuron ® (Henkel), Nutrilan ® (Grünau), Gelita-Sol ® (Deutsche Gelatine Fabriken Stoess & Co), Lexein ® (Inolex) and Kerasol ® (Croda) sold.
• protein hydrolysates of plant origin e.g. B. soy, almond, pea, potato and wheat protein hydrolyzates.
• Such products are available, for example, under the trademarks Gluadin ® (Henkel), DiaMin ® (Diamalt), Lexein ® (Inolex) and Crotein ® (Croda).
• amino acid mixtures obtained in some other way can optionally be used in their place. It is also possible, although less preferred, to use derivatives of the protein hydrolyzates, for example in the form of their fatty acid condensation products or cationically derivatized. Such products are sold for example under the names Lamepon ® (Henkel), Lexein ® (Inolex), Crolastin ® (Croda), Crotein ® (Croda), Lamequat® ® and Croquat ®.
• the protein hydrolyzates or their derivatives are contained in the oxidation coloring agents used according to the invention preferably in amounts of 0.1 to 5% by weight, based on the total agent. Amounts of 0.1 to 2% by weight are particularly preferred.
• the oxidizing coloring agents can in principle contain all further components known to the person skilled in the art for such cosmetic agents.
• auxiliaries and additives are, for example Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. As methyl cellulose, hydroxyalkyl cellulose and carboxy methyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B. bentonite or fully synthetic hydrocolloids such.
• Structurants such as maleic acid and lactic acid, hair-conditioner compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, perfume oils, dimethyl isosorbide and cyclodextrins,
• Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol, active substances that improve fiber structure, in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fructose, fructose and lactose, anti-dandruff substances such as piroctone olamine, zinc omadine and Climbazole, light stabilizers, in particular derivatized benzophenones, cinnamic acid derivatives and triazines,
• active substances that improve fiber structure in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fructose, fructose and lactose, anti-dandruff substances such as piroctone olamine, zinc omadine and Climbazole, light stabilizers, in particular derivatized benzophenones, cinnamic
• Substances for adjusting the pH such as customary acids, in particular edible acids and bases,
• Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and their salts, bisabolol, plant extracts and vitamins cholesterol,
• Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax and paraffins, fatty acid alkanolamides,
• Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates, opacifiers such as latex,
• Pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate, stabilizing agents for hydrogen peroxide and other oxidizing agents, Blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air.
• Cetylstearyl alcohol with approx. 20 EO units (INCI name: Ceteareth-20)
• the dye precursors were dissolved in the water at 50 ° C. with the addition of sodium sulfite, ammonium sulfate and ammonia.
• the coloring cream thus obtained was mixed in a ratio of 2: 1 with a 3% H 2 O 2 solution and applied to 5 cm long strands of standardized, 80% gray, but not specially pretreated human hair (Kerling). After a contact time of 30 minutes at 32 ° C., the hair was rinsed, washed out with a customary shampoo and then dried.
• the colors were characterized by high wash fastness and bright colors.

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• 1999
  • 1999-10-22 DE DE1999151008 patent/DE19951008A1/de not_active Withdrawn
• 2000
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  • 2000-10-13 WO PCT/EP2000/010073 patent/WO2001030743A1/de not_active Application Discontinuation
  • 2000-10-13 EP EP00975865A patent/EP1222161A1/de not_active Ceased
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