WO2002096382A1 - Composants revelateurs pour coloration capillaire d'oxydation - Google Patents

Composants revelateurs pour coloration capillaire d'oxydation Download PDF

Info

Publication number
WO2002096382A1
WO2002096382A1 PCT/EP2002/005521 EP0205521W WO02096382A1 WO 2002096382 A1 WO2002096382 A1 WO 2002096382A1 EP 0205521 W EP0205521 W EP 0205521W WO 02096382 A1 WO02096382 A1 WO 02096382A1
Authority
WO
WIPO (PCT)
Prior art keywords
amino
bis
group
methyl
aminophenol
Prior art date
Application number
PCT/EP2002/005521
Other languages
German (de)
English (en)
Inventor
David Rose
Bernd Meinigke
Horst Höffkes
Georg KNÜBEL
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO2002096382A1 publication Critical patent/WO2002096382A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C07C217/86—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings

Definitions

  • the invention relates to agents for dyeing keratin fibers which contain new p-phenylenediamine derivatives as developer components, a process for dyeing keratin fibers using these p-phenylenediamine derivatives and new p-phenylenediamine derivatives.
  • Keratin fibers are today treated in a variety of ways with hair cosmetic preparations. These include cleaning the hair with shampoos, care and regeneration with rinses and cures, as well as bleaching, dyeing and shaping the hair with dyes, tinting agents, waving agents and styling preparations. Means for changing or balancing the color of the scalp hair play an outstanding role.
  • 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 sensitive to shampooing, so that a frequently undesired shift in shade or even a visible "discoloration" occurs.
  • oxidation colorants are used for permanent, intensive dyeings with appropriate fastness properties, which ensure dyeing at relatively low temperatures and in short dyeing times.
  • 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 by the action of atmospheric oxygen with one another or by coupling with one or more coupler components.
  • a mixture of a large number of oxidation dye precursors usually has to be used for natural-looking dyeings; in many cases direct dyes are still used for shading.
  • Good oxidation dye precursors should primarily fulfill the following requirements: they must develop the desired color shades with sufficient intensity and fastness in the oxidative coupling. They must also have a good ability to draw onto the fiber, with no noticeable differences between stressed and freshly regrown hair, especially with human hair (leveling ability). They should be resistant to light, heat, friction and the influence of chemical reducing agents, e.g. Perm liquids. After all, if they are used as hair dye, they should stain the scalp as little as possible, and above all they should be harmless from a toxicological and dermatological point of view. Furthermore, there should be the possibility of easily removing a coloring obtained from the hair by bleaching, if it nevertheless does not correspond to the individual wishes of the individual and should therefore be reversed.
  • a first object of the invention is therefore an agent for dyeing keratin fibers, in particular human hair, which contains in a medium suitable for dyeing as oxidation dye precursors at least one developer component which is a p-phenylenediamine derivative of the general formula (I),
  • A, B, C and D independently of one another represent an -NH 2 , -NHR or -NR a R b group in which R, R a and R b independently of one another represent a dC 4 -alkyl radical, a C 2 - C 4 hydroxyalkyl radical or a C 2 -C 4 oligohydroxyalkyl radical,
  • R 1 and R 2 independently of one another represent hydrogen, halogen, a CrC-alkyl or '-hydroxyalkyl group, a C 2 -C -dihydroxyalkyl group or a CC 4 - hydroxyalkoxy group,
  • n is an integer from 2-10 and y is an integer from 1-8, with the proviso that n is greater than y .
  • Hydroxyalkyl group a C -C 4 - Dihydroxyalkyl or a C ⁇ - C4 -hydroxyalkoxy.
  • Examples of - -alkyl groups in the compounds according to the invention are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.
  • Preferred alkyl groups are methyl and ethyl, methyl is a particularly preferred alkyl group.
  • Preferred C 2 -C 4 hydroxyalkyl groups are the groups 2-hydroxyethyl, 3-hydroxypropyl or 4-hydroxybutyl; 2-Hydroxyethyl is a particularly preferred hydroxyalkyl group.
  • C 2 -C 4 -Dihydroxyalkyl phenomenon and C ⁇ -C 4 - hydroxyalkoxy groups are 2,3-dihydroxybutyl and 2-hydroxy-3-methoxypropyl.
  • preferred halogen substituents are chlorine, bromine and iodine, and chlorine and bromine are particularly preferred.
  • Particularly preferred p-phenylenediamine derivatives of the formula (I) are 1,3-bis- (2 ', 5'-diaminophenoxy) propan-2-ol; 1,4-bis (2 ', 5'-diaminophenoxy) butane-2,3-diol; 2 - ( ⁇ 4- [(2 ', 5'-diaminophenoxy) methyl] phenyl ⁇ methoxy) -1, 4-diaminobenzene and 2 - ( ⁇ 2 - [(2', 5'-diaminophenoxy) methyl] phenyl ⁇ methoxy) -l, 4-diaminobenzene and their physiologically tolerable salts.
  • the hydrochlorides are particularly preferred physiologically compatible salts of the abovementioned compounds.
  • the agents according to the invention can contain a coupler component.
  • a coupler component m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are usually used for this.
  • Coupler components preferred according to the invention are m-aminophenol and its derivatives, such as 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-.
  • m-aminophenol and its derivatives such as 5-amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminoph
  • 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, 1, 3-bis- (2 ', 4'- diaminophenoxy) propane, 1-methoxy-2-amino- 4- (2'-hydroxyethylamino) -benzoI, 1, 3-bis- (2 ', 4'-diaminophenyl) propane, 2,6-bis- (2'- hydroxyethylamino) -1-methylbenzene 1-ethoxy-2-bis- (2'-hydroxyethyl) -amino-4-aminobenzene and l-amino-3-bis- (2'-hydroxyemyl) aminobenzene, o-diamino benzene and its derivatives such as 3,4-diamino benzoic acid and 2,3-di
  • Di- or trihydroxybenzene derivatives such as, for example, resorcinol, resorcinol monomethyl 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-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3, 4-dimethylpyridine, 2,6-dihydroxy-4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine 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-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 2,3-dihydroxynaphthalene,
  • 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 7-
  • Pyrimidine derivatives such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-
  • Methylenedioxybenzene derivatives such as l-hydroxy-3,4-methylenedioxybenzene, l-amino-3,4-methylenedioxybenzene and l- (2'-hydroxyethyl) - amino-3, 4-methylenedioxybenzene,
  • coupler components are resorcinol, 1-naphthol, 2-amino-3-hydroxy-pyridine, 2-methyl-5-amino-phenol, 2,4-diaminophenoxyethanol, 1,3-bis- (2,4-diaminophenoxy ) -propane, 2,6-dimethoxy-3,5-diaminopyridine, 2-chloro-6-methyl-3-aminophenol, 2-methyl-4-chloro-5-aminophenol, l-hydroxy-2-methyl-naphthalene, 6- methoxy-2-methylamino-3-aminopyridine, 2,4-dichloro-3-aminophenol, 1-methoxy-2- amino-4- (2'-hydroxyethyl) aminobenzene, z, / - jumydroxynaphthalene and 2,6-dihydroxy-3, 4-dimethylpyridine.
  • coupler combinations of two or more coupler components can also be preferred to use coupler combinations of two or more coupler components. Couplings of 2-chloro-6-methyl-3-aminophenol / 6-methoxy-2-methylamino-3-aminopyridine, 2-methyl-5-aminophenol / 2,4- are particularly preferred coupler combinations.
  • Diaminophenoxyethanol 2,7-dihydroxynaphthalene / 2,6-dimethoxy-3,5-diaminopyridine and 2,6-dihydroxy-3,4-dimethylpyridine / 2,4-dichloro-3-aminophenol.
  • Coupler components and developer combinations are usually used.
  • Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof are usually used as further developer components used.
  • P-Phenylenediamine derivatives of the formula (E1) are particularly preferred
  • - G 1 represents a hydrogen atom, a -CC alkyl radical, a C1-C4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a C 4 ) alkyl radical, a 4'-aminophenyl radical or a d-Gt-alkyl radical who with a ⁇ . nitrogen-containing group, a phenyl or a 4'-aminophenyl radical,
  • - G stands for a hydrogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 2 -C polyhydroxyalkyl radical, a (C 1 -C 4 ) alkoxy (C 4 -C 4 ) alkyl radical or a C 1 -C 4 alkyl radical which is substituted by a nitrogen-containing group,
  • - G 3 represents a hydrogen atom, a halogen atom, such as a chlorine, bromine, iodine or fluorine atom, a C 1 -C 4 alkyl radical, a QQ monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a dQ-hydroxyalkoxy radical a C ⁇ -C 4 - Acetylaminoalkoxyrest, a C 1 -C 4 -Mesylaminoalkoxyrest or C ⁇ -C 4 - Carbamoylaminoalkoxyrest,
  • a halogen atom such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 -C 4 alkyl radical such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 -C 4 alkyl radical such as a chlorine, bromine, iodine or fluorine atom
  • - G 4 represents a hydrogen atom, a halogen atom or a C 1 -C 4 alkyl radical or
  • G 3 and G 4 are ortho to each other, they can together form a bridging ⁇ , ⁇ -alkylenedioxo group, such as an ethylenedioxy group.
  • Examples of the C 1 -C 4 -alkyl radicals 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 radicals.
  • Preferred C 1 -C 4 alkoxy radicals according to the invention are, for example, a methoxy or an ethoxy group.
  • Further preferred examples of a Cj-Ci-hydroxyalkyl group are a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group. A 2-hydroxyethyl group is particularly preferred.
  • C 2 -C 4 polyhydroxyalkyl group is the 1,2-dihydroxyethyl group.
  • halogen atoms according to the invention are F, Cl or Br atoms, CI atoms are very particularly preferred.
  • the other terms used are derived from the definitions given here.
  • nitrogen-containing groups of formula (II) are especially the amino groups, C 1 -C 4 monoalkylamino, C ⁇ -C 4 dialkylamino, Ct-C 4 - trialkylammonium groups, C 1 -C 4 -Monohydroxyalkylamino phenomenon, imidazolinium and ammonium.
  • Particularly preferred p-phenylenediamines of the formula (E1) are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p- phenylenediami, 2,6-dimethyl-p-phenylenediamine, 2,6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediarnine, N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p phenylenediamine, N, N-dipropyl-p-phenylenediamine, 4-amino-3-methyl- (N, N-diethyl) aniline, N, N-bis- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 4-N, N-bis (ß-hydroxyethyl) amino-2-methylaniline, 4-N, N-bis (
  • particularly preferred p-phenylenediamine derivatives of the formula (E1) are p-toluenediamine, p-phenylenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine and N, N-bis- ( ⁇ -hydroxyethyl) -p-phenylenediamine.
  • binuclear developer components which can be used in the coloring compositions according to the invention, one can name in particular the compounds which correspond to the following formula (E2) and their physiologically tolerable salts:
  • - Z 1 and Z 2 independently of one another represent a hydroxyl or NH 2 radical which is optionally substituted by a CrQ-alkyl radical, by a C 1 -C 4 -hydroxyalkyl radical and / or by a bridging Y or which is optionally part of a bridging ring system;
  • the bridge Y stands for an alkylene group with 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring which is interrupted or terminated by one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms may be and may be substituted by one or more hydroxyl or Q-Cs alkoxy groups, or a direct bond,
  • G 5 and G 6 independently of one another represent a hydrogen or halogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a C 1 -C 4 - Aminoalkyl radical or a direct connection to the bridging Y,
  • - G, G, G, G, G and G independently of one another represent a hydrogen atom, a direct bond to the bridge Y or a C 1 -C 4 -alkyl radical, with the provisos that the compounds of the formula (E2) only have a bridge Y. contain per molecule and the compounds of formula (E2) contain at least one amino group which carries at least one hydrogen atom.
  • Preferred dinuclear developer components of the formula (E2) are in particular: N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis- (4'-aminophenyl) -1,3-diamino-propan-2-ol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetra-methylenediamine, N, N ' -Bis- (ß-hydroxyethyl) -N, N'-bis- (4-aminophenyl) tetramethylene diamine, N, N'-bis (4-methylaminophenyl) tetramethylene diamine, N, N'-bis (ethyl) -N, N'- bis (4'-amino-3'-methylphenyl) ethylenediamine, bis (2-hydroxy-5-aminoph
  • Very particularly preferred dinuclear developer components of the formula (E2) are N, N'-bis ( ⁇ -hydroxy yl) -N, N'-bis- (4'-ammophenyl) -l, 3-diamino-propan-2-ol , Bis (2-hydroxy-5-aminophenyl) methane, N, N'-bis (4'-aminophenyl) -1,4-diazacycloheptane and l, 10-bis (2 ', 5'-diaminophenyl) -l, 4,7,10-tetraoxadecane or one of its physiologically tolerable salts.
  • P-Aminophenol derivatives of the formula (E3) are particularly preferred
  • G 13 represents a hydrogen atom, a halogen atom, a C 1 -C 4 -alkyl radical, a Ci
  • (-C-C 4 ) -alkyl radical a C 1 -C 4 -aminoalkyl radical, a hydroxy- (C ⁇ -C 4 ) -alkylamino radical, a -C-C 4 -hydroxyalkoxy radical, a C 1 -C 4 -hydroxyalkyl- (C 1 -bis C) -aminoalkyl radical or a (di-C ⁇ -C 4 alkylamino) - (-C-C) alkyl radical, and
  • - G 14 represents a hydrogen or halogen atom, a C 1 -C 4 alkyl radical, a CrC 4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a (Cr C 4 ) alkoxy- (C ⁇ - C 4 ) -alkyl radical, a C ⁇ -Q-aminoalkyl radical or a Ci- C 4 cyanoalkyl radical,
  • - G 15 represents hydrogen, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a phenyl radical or a benzyl radical, and
  • - G 16 represents hydrogen or a halogen atom.
  • Preferred p-aminophenols of the formula (L3) are in particular p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4 - amino-3-hydroxymethylphenol, 4-amino-2- (2-hydroxyethoxy) phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino- 2-aminomethylphenol, 4-amino-2- (ß-hydroxyethyl-aminomethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2-chlorophenol, 2,6-dichloro-4-aminophenol, 4-amino-2 - ((Diemylamino) methyl) phenol and their physiologically acceptable salts.
  • Very particularly preferred compounds of the formula (E3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol and 4-amino-2 - ((diethylamino) methyl) phenol.
  • the developer component can be selected from o-aminophenol and its derivatives, such as, for example, 2-amino-4-methylphenol or 2-amino-4-chlorophenol.
  • heterocyclic developer components such as the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically acceptable salts.
  • pyrimidine or pyrazole derivatives are preferred.
  • Preferred pyrimidine derivatives are, in particular, the compounds described in German patent DE 2 359 399, Japanese laid-open patent publication JP 02019576 A2 or in laid-open publication WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy- 2,5, 6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2.5, 6- triaminopyrimidine.
  • Preferred pyrazole derivatives are in particular the compounds described in the patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, EP-740931 and DE 195 43 988, such as 4,5- Diamino-l-methylpyrazole, 4,5-diamino-1 - ( ⁇ -hydroxyethyl) pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1 - (4'-chlorobenzyl) pyrazole, 4,5-diamino -l, 3-dimethylpyrazole, 4,5-diamino-3-methyl-1 - phenylpyrazole, 4,5-diamino-l-methyl - 5-pl ⁇ enylpyrazol, 4-amino-l, 3-dimethyl-5-hydrazinopyrazole, 1 -BerLzyl-4,5-diarnino-3-methylpyrazole
  • Preferred pyridine derivatives are, in particular, the compounds described in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino-pyridine, 2- (4-methoxyphenyl) amino-3-amino-pyridine, 2 , 3-diamino-6-methoxy-pyridine, 2- (ß-meth-oxyethyl) amino-3-amino-6-methoxy-pyridine and 3,4-diamino-pyridine.
  • Preferred pyrazole-pyrimidine derivatives are, in particular, the derivatives of pyrazoI- [1,5-a] -pyrimidine of the following formula (E4) and its tautomeric forms, provided that there is a tautomeric equilibrium:
  • G 17 , G 18 , G 19 and G 20 independently of one another represent a hydrogen atom, a C 4 -C 4 alkyl radical, an aryl radical, a C 1 -C 4 hydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical a ( C 1 -C 4 ) -Ai'koxy- (C 1 -C 4 ) -alkyl radical, a C!
  • -C 4 -aminoalkyl radical which can optionally be protected by an acetyl-ureide or sulfonyl radical, a (C 1 -C) alkylamino (C 1 -C 4 ) alkyl, a di - [(CrC 4 ) alkyl] - (C 1 -C 4 ) aminoalkyl, the dialkyl optionally having a carbon cycle or a heterocycle 5 or 6 chain links form a C 1 -C 4 hydroxyalkyl or a di (C 1 -C) - [hydroxyalkyl] - (C 1 -C) aminoalkyl radical, -
  • the X radicals independently of one another represent a hydrogen atom, a dC alkyl radical, an aryl radical, a C 1 -C 4 hydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a dC 4 aminoalkyl radical, a (C 1 -C
  • - i has the value 0, 1, 2 or 3
  • - n has the value 0 or 1, with the proviso that
  • n has the value 0, and the groups NG 17 G 18 and NG 19 G 20 occupy positions (2,3); (5,6); (6,7); (3.5) or (3.7);
  • pyrazole [1,5-a] pyrimidines of the above formula (E4) can be prepared as described in the literature by cyclization starting from an aminopyrazole or from hydrazine.
  • Additional developer components preferred according to the invention are pyrimidine derivatives, pyrazole derivatives, p-aminophenol derivatives and p-diaminobenzene derivatives.
  • additional developer components are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, N, N-bis ( ⁇ -hydroxyethyl) -p-phenylenediamine, N, N'-bis- ( ß-Hydroxyethyl) -N, N'-bis- (4'-aminophenyl) -1,3-diamino-propan-2-ol, bis- (2-hydroxy-5-aminophenyl) -methane, N, N'- Bis- (4'- aminophenyl) - 1, 4-diazacycloheptane, 1, 10-bis (2 ', 5'-diaminophenyl) - 1, 4.7, 10-tetra-oxadecane, p-aminophenol, 4-amino -3-methylphenol, 4-amino-3-fluorophenol, 4-amino-2
  • the hair colorants according to the invention preferably contain both the developer components and the coupler components in an amount of 0.005 to 10% by weight, preferably 0.1 to 5% by weight, based in each case on the total oxidation colorant.
  • Developer components and coupler components are generally used in approximately molar amounts to one another. If molar use has also proven to be expedient, 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 be included.
  • the agents according to the invention can furthermore contain precursors of nature-analogous dyes.
  • These groups can carry further substituents, e.g. B. in the form of etherification or esterification of the hydroxy group or an alkylation of the amino group.
  • Derivatives of 5,6-dihydroxyindoline of the formula (Ha) are particularly suitable as precursors of nature-analogous hair dyes,
  • R 1 stands for hydrogen, a dC 4 -allcyi group, a C 1 -C 4 hydroxyalkyl group, a C 3 -C 6 cycloalkyl group or a C 2 -C 4 alkenyl group, in particular a vinyl or allyl group,
  • R 2 stands for hydrogen or a -COOH group, where the -COOH group can also be present as a salt with a physiologically compatible cation
  • R 3 stands for hydrogen or a dC 4 alkyl group
  • R 4 stands for hydrogen, a C 1 -C alkyl group or a group -CO-R 6 , in which R 6 stands for a C 1 -C 4 alkyl group, and R 5 stands for one of the groups mentioned under R 4 , as well as physiologically tolerable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indoline are 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 and 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
  • N-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially that 5,6-Dihydroxyindolin.
  • R 1 stands for hydrogen, a CC -Ai ⁇ y ⁇ distr, a C 1 -C -hydroxyalkyl group, a C 3 -C 6 cycloalkyl group or a C 2 -C 4 alkenyl group, in particular one
  • R 2 stands for hydrogen or a -COOH group, where the -COOH group can also be present as a salt with a physiologically compatible cation
  • R 3 represents hydrogen or a dC -alkyl group
  • R 4 represents hydrogen, a C 1 -C 4 alkyl group or a group -CO-R 6 , in which
  • R represents a dC 4 alkyl group
  • R 5 stands for one of the groups mentioned under R 4 , as well as physiologically tolerable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indole 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.
  • N-methyl-5,6-dihydroxyindole N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole and in particular 5.6 -Dihydroxyindol.
  • the indoline and indole derivatives can be used in the colorants used in the process according to the invention both as free bases and in the form of their physiologically tolerable salts with inorganic or organic acids, for.
  • the indole or indoline derivatives are usually contained in these in amounts of 0.05-10% by weight, preferably 0.2-5% by weight.
  • the hair colorants according to the invention in addition to the oxidation dye precursors, also remove conventional direct dyes for further modification of the color shades.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred substantive dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, HC Orange 1, Disperse Orange 3, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, HC Red BN, HC Blue 2, HC Blue 12, Disperse Blue 3, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9 and Acid Black 52
  • aromatic systems which are substituted with a quaternary nitrogen group, such as, for example, Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, and
  • Preferred cationic direct dyes of group (c) are in particular the following compounds:
  • the compounds of the formulas (DZl), (DZ3) and (DZ5) are very particularly preferred cationic direct dyes of group (c).
  • the agents according to the invention in accordance with this embodiment preferably contain the substantive dyes in an amount of 0.01 to 20% by weight, based on the total colorant.
  • the preparations according to the invention can also contain dyes that occur naturally, such as those contained in henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • the agents according to the invention preferably contain dye precursors in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier are, for example, creams, emulsions, gels or also surfactant-containing foaming solutions, such as shampoos, aerosols or other preparations which are suitable for use on the hair.
  • surfactant-containing foaming solutions such as shampoos, aerosols or other preparations which are suitable for use on the hair.
  • aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing 3 to 70% by weight of a C 4 -C 4 alcohol, in particular ethanol or isopropanol.
  • the agents according to the invention can additionally contain other organic solvents, such as methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. All water-soluble organic solvents are preferred.
  • the agents according to the invention can furthermore contain all active substances, additives and auxiliary substances known for such preparations.
  • these agents contain at least one surfactant, in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases, however, it has proven advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • Suitable anionic surfactants in preparations 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 z. 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 aniide groups and hydroxyl groups.
  • anionic surfactants are, in each case in the form of the sodium, potassium and ammonium and the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group, linear fatty acids with 10 to 22 carbon atoms (soaps )
  • Ether carboxylic acids of the formula RO- (CH 2 -CH 2 O) x -CH 2 -COOH, in which R is a linear one
  • Alkyl group with 10 to 22 carbon atoms and x 0 or 1 to 16,
  • Atoms in the alkyl group and 1 to 6 oxyethyl groups linear alkanesulfonates with 12 to 18 C atoms, linear alpha-olefin sulfonates with 12 to 18 C atoms,
  • Alpha-sulfofatty acid methyl esters of fatty acids with 12 to 18 carbon atoms, alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH 2 -CH 2 O) x -SO 3 H, in which R is a preferably linear alkyl group with 10 to 18 carbon atoms and x 0 or 1 to 12,
  • 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
  • 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 in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • 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. Such alkyl radicals are, for example, 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 1 .
  • these compounds are made from natural fats and oils or mineral oils.
  • the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the respective working up of these compounds.
  • R consists essentially of C 8 and C 10 alkyl groups, consists essentially of C 12 - and C ⁇ -alkyl groups, essentially of C 8 -C 16 -alkyl groups or essentially of C 12 -Ci 6 -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.
  • alkyl polyglycosides which can be used according to the invention contain an average of 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 surface-active compounds that contain at least one quaternary ammonium group and at least one in the molecule
  • zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimemylammonium glycinate, N-acyl-aminopropyl-N, N-dimethyl-ammonium-glycinate, for example the cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, as well as the cocoacylaniinoethylhydroxyethylcarboxymethylglycinate.
  • 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 8 -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 are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N -alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each with about 8 to 18 C. Atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C 12- 1 8 - sarcosine.
  • the cationic surfactants used are, in particular, those of the quaternary ammonium compound, esterquat and amidoamine type.
  • 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, as well as 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.
  • Esterquats are known substances that have both at least one ester function and at least one quaternary ammonium group as a structural element contain.
  • 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 inventively particularly suitable compound from this group of substances that available under the name Tegoamid ® S 18 commercially stearamidopropyldimethylamine is dimethylamine.
  • the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Coming 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 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80).
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to INCI nomenclature a "lauryl methyl Gluceth-10 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 Mixtures of substances with different alkyl chain lengths depending on the respective raw material.
  • 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 homologues which are obtained as catalysts when fatty alcohol and alkylene oxide are reacted 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 agents according to the invention can preferably also contain a conditioning active ingredient selected from the group formed by cationic surfactants, cationic polymers, alkylamidoamines, paraffin oils, vegetable oils and synthetic oils.
  • Cationic polymers can be preferred as conditioning agents. These are usually polymers that have a quaternary nitrogen atom, for example in the form of a
  • Preferred cationic polymers are, for example, 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.
  • polymeric dimethyldiallylammonium salts and their copolymers with acrylic acid and esters and amides of acrylic acid and methacrylic acid The under the names Merquat ® 100 (poly (dimethyldiallylammom ' umchlorid)),
  • Merquat ® 550 (pimethyldiallylainmoniumchlorid-acrylamide copolymer) and Merquat ® 280 (Dimemyldiallyl-anrnioniumchlorid-acrylic acid copolymer commercially available products are examples of such cationic polymers.
  • Dialkylaminoacrylate and methacrylate such as vinylpyrrolidone-dimethylaminomethacrylate copolymers quaternized with diethyl sulfate.
  • Luviquat ® quaternized polyvinyl alcohol and those under the names
  • Polyquaternium 27 known polymers with quaternary nitrogen atoms in the
  • Polymer backbone Cationic polymers of the first four groups are particularly preferred; polyquaternium-2, polyquaternium-10 and polyquaternium-22 are very particularly preferred.
  • conditioning agents are silicone oils, 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 Corning under the names DC 190, DC 200, DC 344, DC 345 and DC 1401 as well as the commercial products Q2-7224 (manufacturer: Dow Coming; a stabilized trimethylsilylamodimethicone), Dow Coming® 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 (manufacturer: Th. Goldschmidt ; diquaternary polydimethylsiloxanes, Quaternium-80).
  • Paraffin oils synthetically produced oligomeric alkenes and vegetable oils such as jojoba oil, sunflower oil, orange oil, almond oil, wheat germ oil and peach seed oil can also be used as conditioning agents.
  • suitable hair-conditioning compounds are phospholipids, for example soy lecithin, egg lecithin and cephalins.
  • nonionic polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes
  • zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimemylaiTunoniumchloride / acrylate-acrylate / acrylate-acrylate / acrylate-acrylate / acrylate-acrylate / acrylate-copolymer / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers
  • anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers,
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such. B. bentonite or fully synthetic hydrocolloids such as e.g. polyvinyl alcohol,
  • Structurants such as maleic acid and lactic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins,
  • Protein hydrolyzates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids and quaternized protein hydrolyzates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solvents and intermediates such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol, active substances which improve the fiber structure, in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fructose, fructose and lactose,
  • Quaternized amines such as methyl 1-alkylamidoemyl-2-akylimidazolinium methosulfate - defoamers like silicones,
  • Anti-dandruff agents such as piroctone olamine, zinc omadine and climbazole, light stabilizers, in particular derivatized benzophenones, cinnamic acid derivatives and triazines,
  • Substances for adjusting the pH such as customary acids, in particular edible acids and bases,
  • Active ingredients such as allantoin, pyrrolidone carboxylic acids and their salts and bisabolol,
  • Vitamins, provitamins and vitamin precursors especially those of groups A, B 3 ,
  • Plant extracts such as the extracts from green tea, oak bark, nettle,
  • Melissa, hake, coltsfoot, marshmallow, meristem, ginseng and ginger root Melissa, hake, coltsfoot, marshmallow, meristem, ginseng and ginger root ,.
  • 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 glycerin, propylene glycol monoethyl ether, carbonates,
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers
  • Pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate,
  • a second subject of the invention is a process for coloring keratin fibers, in particular hair, using an oxidation colorant according to the invention.
  • the actual hair dye is expediently prepared immediately before use by mixing the preparation of the oxidizing agent with the preparation containing the dye precursors.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 12.
  • the use of hair colorants in a weakly alkaline environment is particularly preferred.
  • the application temperatures can range between 15 and 40 ° C.
  • the hair dye is removed from the hair to be colored by rinsing. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. a coloring shampoo was used.
  • the actual oxidative coloring of the fibers can basically be done with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially if, in addition to the coloring, a lightening effect on human hair is desired.
  • Persulfates, chlorites and in particular hydrogen peroxide or their adducts with urea, melamine and sodium borate are suitable as oxidizing agents. 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, ascorbate oxidase 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.
  • a third subject of the invention is the use of compounds of the formula (I) as developer components in oxidation colorants for dyeing keratin fibers, in particular hair.
  • New and thus a fourth object of the foundation are the compounds according to formula (I) according to Claim 1, which are characterized by the following combinations of substituents:
  • a base cream of the following composition was produced (unless otherwise stated, all information relates to the mass fraction in g):
  • Cocoamidopropyl betaine (30% solution) 25.0
  • Coupler components 7.5 mmol
  • the ingredients were mixed together in order. After the oxidation dye precursors and the inhibitor had been added, the pH of the emulsion was first adjusted to pH 10 using concentrated ammonia solution, and the mixture was then made up to 100 g with water. The oxidative development of the coloring was carried out with 3% hydrogen peroxide solution as the oxidation solution. For this purpose, 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) and mixed.
  • the coloring cream was applied to approx. 5 cm long strands of standardized, 90% gray, but not specially pretreated human hair and left there at 32 ° C for 30 minutes. After the dyeing process was completed, the hair was rinsed, washed with a conventional shampoo and then dried.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne des dérivés de p-phénylèndiamine de formule (I), dans laquelle A, B, C et D représentent indépendamment des groupes -NH2-, -NHR? ou -NRaRb-, R1 et R2¿ représentent indépendamment hydrogène, halogène, un groupe alkyle C¿1?-C4 ou hydroxyalkyle C1-C4, un groupe dihydroxyalkyle C2-C4 ou un groupe hydroxyalkoxy C1-C4 et E représente -O-(CnH2n-y(OH)y)-O-, avec n est un nombre entier allant de 2 à 10 et y est un nombre entier allant de 1 à 8, sous réserve que n soit supérieur à y, ou (II), avec x est un nombre entier allant de 1 à 5 et R?3¿ représente hydrogène, halogène, un groupe alkyle C¿1?-C4 ou hydroxyalkyle C1-C4, un groupe dihydroxyalkyle C2-C4 ou un groupe hydroxyalkoxy C1-C4. Ces dérivés de p-phénylèndiamine et leurs sels, physiologiquement compatibles, conviennent en tant que composants révélateurs dans la production de colorants d'oxydation, servant notamment à la coloration de cheveux humains.
PCT/EP2002/005521 2001-05-28 2002-05-18 Composants revelateurs pour coloration capillaire d'oxydation WO2002096382A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10125880.1 2001-05-28
DE2001125880 DE10125880A1 (de) 2001-05-28 2001-05-28 Neue Entwicklerkomponenten für Oxidationshaarfarben

Publications (1)

Publication Number Publication Date
WO2002096382A1 true WO2002096382A1 (fr) 2002-12-05

Family

ID=7686360

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/005521 WO2002096382A1 (fr) 2001-05-28 2002-05-18 Composants revelateurs pour coloration capillaire d'oxydation

Country Status (2)

Country Link
DE (1) DE10125880A1 (fr)
WO (1) WO2002096382A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1433470A1 (fr) * 2002-12-23 2004-06-30 Henkel Kommanditgesellschaft auf Aktien Composition de teinture des fibres kératiniques
EP1473023A1 (fr) * 2003-04-29 2004-11-03 L'oreal Composition tinctoriale comprenant le 2-chloro 6-méthyl 3-amino phénol à titre de coupleur, le para-aminophénol et le 3-méthyl 4-amino phénol à titre de base d'oxydation et un polymère épaississant associatif
US7276087B2 (en) 2003-04-29 2007-10-02 L'oreal S.A. Dye composition comprising 2-chloro-6-methyl-3-aminophenol as coupler, para-aminophenol and 3-methyl-4-aminophenol as oxidation bases and at least one associative thickening polymer
US7300470B2 (en) 2003-04-29 2007-11-27 L'oreal S.A. Dye composition comprising 2-chloro-6-methyl-3-aminophenol, at least two oxidation bases chosen from para-phenylenediamine derivatives and at least one associative thickening polymer
US7306630B2 (en) 2003-04-29 2007-12-11 L'oreal S.A. Composition comprising at least one coupler chosen from 2-chloro-6-methyl-3-aminophenol and addition salts thereof, at least one oxidation base, and at least one associative polymer comprising at least one C8-C30 fatty chain

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0036591A1 (fr) * 1980-03-22 1981-09-30 Henkel Kommanditgesellschaft auf Aktien Composants de coupleur pour colorants d'oxydation de cheveux, leur préparation et utilisation ainsi que colorants pour cheveux les contenant
DE3149330A1 (de) * 1981-12-12 1983-06-16 Henkel KGaA, 4000 Düsseldorf Hydroxyethylierte bis-(2,5-diaminophenoxy)-alkane und deren verwendung in haarfaerbemitteln
DE4102907A1 (de) * 1991-01-31 1992-08-06 Henkel Kgaa 2,5-diaminophenoxy-oxaalkane und deren verwendung als oxidationsfarbstoffvorprodukte

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0036591A1 (fr) * 1980-03-22 1981-09-30 Henkel Kommanditgesellschaft auf Aktien Composants de coupleur pour colorants d'oxydation de cheveux, leur préparation et utilisation ainsi que colorants pour cheveux les contenant
DE3149330A1 (de) * 1981-12-12 1983-06-16 Henkel KGaA, 4000 Düsseldorf Hydroxyethylierte bis-(2,5-diaminophenoxy)-alkane und deren verwendung in haarfaerbemitteln
DE4102907A1 (de) * 1991-01-31 1992-08-06 Henkel Kgaa 2,5-diaminophenoxy-oxaalkane und deren verwendung als oxidationsfarbstoffvorprodukte

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1433470A1 (fr) * 2002-12-23 2004-06-30 Henkel Kommanditgesellschaft auf Aktien Composition de teinture des fibres kératiniques
EP1473023A1 (fr) * 2003-04-29 2004-11-03 L'oreal Composition tinctoriale comprenant le 2-chloro 6-méthyl 3-amino phénol à titre de coupleur, le para-aminophénol et le 3-méthyl 4-amino phénol à titre de base d'oxydation et un polymère épaississant associatif
FR2854327A1 (fr) * 2003-04-29 2004-11-05 Oreal Composition tinctoriale comprenant le 2-chloro 6-methyl 3- aminophenol a titre de coupleur, le para-aminophenol et le 3-methyl 4-amino phenol a titre de base d'oxydation
US7276087B2 (en) 2003-04-29 2007-10-02 L'oreal S.A. Dye composition comprising 2-chloro-6-methyl-3-aminophenol as coupler, para-aminophenol and 3-methyl-4-aminophenol as oxidation bases and at least one associative thickening polymer
US7300470B2 (en) 2003-04-29 2007-11-27 L'oreal S.A. Dye composition comprising 2-chloro-6-methyl-3-aminophenol, at least two oxidation bases chosen from para-phenylenediamine derivatives and at least one associative thickening polymer
US7306630B2 (en) 2003-04-29 2007-12-11 L'oreal S.A. Composition comprising at least one coupler chosen from 2-chloro-6-methyl-3-aminophenol and addition salts thereof, at least one oxidation base, and at least one associative polymer comprising at least one C8-C30 fatty chain

Also Published As

Publication number Publication date
DE10125880A1 (de) 2002-12-05

Similar Documents

Publication Publication Date Title
DE10260834A1 (de) Neue Kupplerkomponenten
EP1304994B1 (fr) Nitrophenols substitues pyrrolyle en tant que colorants directs
WO2002032379A2 (fr) Colorants d'oxydation contenant 2-chloro-4-aminophenol
DE10118883A1 (de) Neue Kupplerkomponenten für Oxidationshaarfarben
WO2002058652A1 (fr) Nouveaux copulants pour colorants d'oxydation
WO2002096382A1 (fr) Composants revelateurs pour coloration capillaire d'oxydation
WO2003041671A2 (fr) Colorants d'oxydation contenant du bis-(5-amino-2-hydroxyphenyl)-methane
EP1292578B1 (fr) Derives de para-aminophenol et leur utilisation comme revelateurs pour la production de teintures d'oxydation
WO2002006207A2 (fr) Nouveaux copulants pour colorants d'oxydation
DE10103160A1 (de) Neue Kupplerkomponente für Oxidationsfärbemittel
WO2003053384A1 (fr) Nouvelle combinaison revelateurs-copulants contenant du 2,4-dichloro-3-aminophenol
EP1406577B1 (fr) Nouveaux composants de copulation destines a la coloration par oxydation des cheveux
WO2001097766A2 (fr) Colorant d'oxydation pour les cheveux
WO2002026200A1 (fr) Colorant d'oxydation contenant du 2-amino-5-methylphenol
WO2002010118A1 (fr) Colorants d'oxydation
WO2002026201A2 (fr) Colorants d'oxydation contenant 2-amino-5-methylphenol
DE10245426A1 (de) Neue Kupplerkomponenten
WO2002032385A1 (fr) Agents colorants d'oxydation contenant 2-chloro-p-aminophenol
WO2003053385A1 (fr) Nouveaux colorants d'oxydation contenant du 2,4-dichloro-3-aminophenol
DE10260836A1 (de) Neue Entwicklerkomponenten
WO2002026202A2 (fr) Colorants d'oxydation contenant 2-amino-5-methylphenol
WO2005117817A1 (fr) Constituants copulants m-phenylenediamine
WO2002005767A1 (fr) Colorants d'0xydation capillaires renfermant comme copulants au moins un diaminophenylether disubstitue en 2, 4
DE10237932A1 (de) Neue Entwicklerkomponenten
DE10260822A1 (de) Neue Kupplerkomponenten

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BR CA CN CZ HU JP NO PL RU SK US VN

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP