EP1423355A1 - P-phenylendiamines pontees - Google Patents

P-phenylendiamines pontees

Info

Publication number
EP1423355A1
EP1423355A1 EP02798707A EP02798707A EP1423355A1 EP 1423355 A1 EP1423355 A1 EP 1423355A1 EP 02798707 A EP02798707 A EP 02798707A EP 02798707 A EP02798707 A EP 02798707A EP 1423355 A1 EP1423355 A1 EP 1423355A1
Authority
EP
European Patent Office
Prior art keywords
bridged
phenylenediamines
amino
alkyl
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP02798707A
Other languages
German (de)
English (en)
Inventor
Georg KNÜBEL
David Rose
Bernd Meinigke
Horst Höffkes
Helmut Giesa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1423355A1 publication Critical patent/EP1423355A1/fr
Pending legal-status Critical Current

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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
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group 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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the present invention relates to new bridged p-phenylenediamines, their use as a developer component in oxidation colorants and to new oxidation colorants which contain the aforementioned bridged p-phenylenediamines.
  • the present invention further relates to a process for the preparation of the bridged p-phenylenediamines.
  • oxidation colorants play a preferred role here, since these enable particularly intensive colorations and have good fastness properties.
  • the oxidation colorants contain so-called developer components and coupler components as oxidation dye precursors.
  • the developer components are also referred to as oxidation bases.
  • the oxidation dye precursors and especially the developers have to meet a wide range of requirements:
  • They should be resistant to light, heat, sweat and the influence of chemical reducing agents, such as permanent wave fluids. Furthermore, they should not stain the scalp too much when used as a hair dye.
  • the oxidation dye products should be absolutely harmless from a toxicological and dermatological point of view.
  • Typical so-called coupler components are, for example, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols.
  • Particularly suitable coupler substances include 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, l-phenyl 3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, l, 3-bis (2 ', 4'-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro 6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-chloro-5-aminophenol.
  • Frequently used developer components are primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6- Tetraminopyrimidine and its derivatives.
  • the widely used developer components also include p-phenylenediamine (PPD) and methyl-p-phenylenediamine, which is also referred to as p-toluenediamine (PTD). These have been used in permanent oxidation hair colors for decades. Despite their good application properties, PPD and PTD cannot be used without hesitation. Both PPD and PTD are not considered to be completely harmless from a toxicological point of view.
  • PPD / PTD derivatives with very voluminous substituents have significantly poorer application properties Have properties and are therefore not or only poorly suited for use in oxidation colorants.
  • the aforementioned PPD / PTD-based developer substances with very voluminous substituents can often only achieve very poor color intensities.
  • DE 2518393 describes tetraaminobiphenyls and tetraaminodiphenyl ethers as developer components.
  • the aforementioned dimers are linked to one another via the benzene rings of the PPD units.
  • a first subject of the present invention are therefore bridged p-phenylenediamines of the general formula (I)
  • (B) is a polyoxaalkyl bridge that has at least two oxygen atoms: - X and Y independently of one another for H, Cl, F, a dC 4 alkyl, aminoalkyl, alkoxy, C 2 -C 4 dihydroxyalkyl, C 1 -C 4 monohydroxyalkyl or a C 2 -C alkenyl group stand; and
  • R 1, R 2, R 3 and R 4 independently of one another represent H, a CrC 4 alkyl, a C 1 -C 4 monohydroxyalkyl or a C 2 -C 4 dihydroxyalkyl group, and acid addition salts derived therefrom.
  • X and Y in formula (I) each represent one or more of the substituents specified above. Accordingly, the present invention also includes bridged p-phenylenediamines which, in addition to the two amino groups, have one, two, three or even four substituents on the benzene ring of the phenylenediamine unit (s).
  • Examples of the C 1 -C 4 alkyl groups mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and / or butyl. Ethyl and / or methyl are preferred alkyl groups.
  • a preferred Ci- alkoxy group according to the invention is, for example, a methoxy and / or an ethoxy group.
  • a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl and / or a 4-hydroxybutyl group can be mentioned as preferred examples of a C 1 -C -hydroxyalkyl group.
  • Particularly preferred C 2 -C 4 dihydroxyalkyl groups are, for example, 1,2-dihydroxyethyl, 1,2-dihydroxypropyl, 1,3-dihydroxypropyl, 2,3-dihydroxypropyl, 1,2-dihydroxybutyl, 1,3- Dihydroxybutyl, 1,4-dihydroxybutyl, 2,3-dihydroxybutyl, 2,4-dihydroxybutyl and / or 3,4-dihydroxybutyl groups.
  • Particularly suitable C 2 -C 4 alkenyl groups are the vinyl, the allyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl and / or the 2-methylpropenyl group.
  • the present invention relates to bridged p-phenylenediamines with a structure according to formula (II)
  • - X and Y independently of one another for H, Cl, F, a Q- alkyl, aminoalkyl, alkoxy, C 2 -C 4 dihydroxyalkyl, C 1 -C 4 monohydroxyalkyl or a C 2 -C - Alkenyl group; and
  • R 1, R 2, R 3 and R 4 independently of one another represent H, a C 1 -C 8 -alkyl, a C 1 -C 4 -monohydroxyalkyl or a C 2 -C 4 -dihydroxyalkyl group.
  • the present invention relates to bridged p-phenylenediamines with a structure according to formula (III)
  • - X and Y independently of one another for H, Cl, F, a C 1 -C 4 alkyl, aminoalkyl, alkoxy, C 2 -C dihydroxyalkyl, CrC 4 monohydroxyalkyl or a C 2 -C 4 - Alkenyl group; and - Rl, R2, R3 and R4 are independently H, a C ⁇ -C 4 alkyl, a C 4 CJ -Monohydroxyalkyl- or a C 2 -C 4 -dihydroxyalkyl stand.
  • the present invention relates to bridged p-phenylenediamines with a structure according to formula (IV)
  • - X and Y independently of one another for H, Cl, F, a C 1 -C 4 alkyl, aminoalkyl, alkoxy, C 2 -C dihydroxyalkyl, - monohydroxyalkyl or a C 2 -C 4 alkenyl group stand; and
  • Rl, R2, R3 and R4 independently represent H, a C alkyl, a Ci- C 4 -Monohydroxyalkyl- or a C 2 -C 4 -dihydroxyalkyl stand.
  • the above-mentioned amino compounds according to the invention can be easily converted into their corresponding acid addition salts.
  • the present invention also relates to the acid addition salts derived from the respective compounds.
  • Water-soluble, physiologically tolerable salts suitable according to the invention include, for example, the hydrochlorides, the hydrobromides, the sulfates, the phosphates, the acetates, the propionates, the citrates and the lactates. Hydrochlorides are particularly preferred.
  • a process for the preparation of the bridged p-phenylenediamines according to formulas (I), (II), (III) or (IV) according to the invention comprises the following steps: a) reaction of l-fluoro-4- nitrobenzene with a polyoxaalkyl diamine in the presence of a base, l-fluoro-4-nitrobenzene and the polyoxaalkyl diamine preferably being used in a ratio of 2: 1, and b) hydrogenation of the intermediate product obtained in step a).
  • Polyoxaalkyldiamines suitable according to the invention include linear or branched polyoxaalkyls which have at least two, preferably primary, amino groups.
  • the polyoxaalkyl provided with at least two terminal amino functions forms the “bridge” provided according to the invention in the resulting dimer.
  • triethylamine or triethanolamine is preferably used as the base. It is preferred to use the 1-fluoro-4-nitrobenzene, the polyoxaalkyl diamine and the base in a ratio of 2: 1: 2.
  • reaction of l-fluoro-4-nitrobenzene with polyoxoalkydiamine in DMSO is preferably carried out at elevated temperatures, preferably at a temperature of more than 50 ° C., particularly preferably at about 80 ° C.
  • the polyoxoalkyldiamine to be reacted is selected from the group comprising 2,2 '- (ethylenedioxy) diethylamine, 1,4-bis (3-aminopropoxy) butane and 4,7,10-trioxa-l, 13- tridecanediamine.
  • the bridged bis [(4-nitrophenyl) amino] compound obtained in step a) of the process according to the invention is reduced in step b) below to the corresponding bis [(4-ammophenyl) amino] compound.
  • the nitro groups can be hydrogenated by processes known per se. For example, the Catalytic hydrogenation with hydrogen in the presence of palladium on activated carbon (Pd / C) has been demonstrated.
  • an oxidation colorant for dyeing keratin fibers which contains as developer component at least one polyoxaalkyl-bridged p-phenylenediamine according to the invention.
  • the oxidation colorant in addition to the at least one developer component, comprises at least one coupler component.
  • Keratin fibers or keratin fibers in the sense of the present invention are to be understood according to the invention as furs, wool, feathers, hair 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
  • Oxidation colorants in an aqueous carrier or in powder form are particularly preferred for the purposes of the present invention.
  • coupler substances known in the prior art can be used as coupler components.
  • the oxidation colorant contains at least one coupler component selected from the group comprising m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives.
  • Coupler components preferred according to the invention are m-aminophenol and its derivatives, such as 5-amino-2-methylphenol, 5- ( ⁇ -hydroxyethyl) 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, 1,3-dihydroxy-5- (methylamino) benzene, 3-
  • m-aminophenol and its derivatives such as 5-amino-2-methylphenol, 5- ( ⁇ -hydroxyethyl) amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3-amino-2
  • Diaminophenoxyethanol 1, 3-bis (2 ', 4'-diaminophenoxy) propane, 1-methoxy-2-amino-4- (2'-hydroxyethylamino) benzene, 1, 3-bis (2', 4 ' -diaminophenyl) -propane, 2,6-
  • Resorcinol monomethyl ether 2-methylresorcinol, 5-methylresorcinol, 2,5-
  • 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-
  • Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-
  • 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-
  • hydroxyindole - Pyrimidine derivatives, such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-amino-4-methylpyrimidine, 2-amino -4-hydroxy-6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine, or
  • Methylenedioxybenzene derivatives such as l-hydroxy-3,4-methylenedioxybenzene, l-amino-3,4-methylenedioxybenzene and l- (2'-hydroxyethyl) - amino-3, 4-methylenedioxybenzene.
  • Suitable coupler substances are in particular 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomino methyl ether, m-phenylenediamine, l-phenyl -3-methyl-5-pyrazolone, 2,4-dichloro-3-aminophenol, l, 3-bis- (2,, 4'-diaminophenoxy) propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2 -Chlor-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol, 3,5-diamino-2-methoxytoluene, 5- (ß-hydroxyethyl) amino-2-methylphenol and 2-methyl-4-chloro-5-aminophenol.
  • the oxidation colorant according to the invention comprises, in addition to at least one polyoxaalkyl-bridged p-phenylenediamine according to the invention, at least one further developer component, preferably selected from the group comprising 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N, N-bis ( 2'-hydroxyethyl) -p-phenylenediamine, 2- (2 ', 5'-diaminophenyl) ethanol, 2- (2', 5'-diaminophenoxy) ethanol, 4-amino-3-methylphenol, 2-aminomethyl 4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triamino-4-hydroxypyrimidine, 1, 3-N, N'-bis (2'-hydroxyethyl) - N, N '-bis (4' -aminophen
  • Additional developer components preferred according to the invention further comprise p-phenylenediamine, p-toluenediamine, p-aminophenol, o-aminophenol, 1- (2'-hydroxyethyl) -2,5-diaminobenzene, N, N-bis (2'-hydroxyethyl) - p-phenylenediamine, 2- (2 ', 5'-diaminophenoxy) ethanol, 4-amino-3-methylphenol, 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2-
  • the hair colorant can contain any other developer component in addition to the polyoxaalkyl-bridged p-phenylenediamine according to the invention.
  • the hair colorants according to the invention contain the developer components in an amount of 0.005 to 20% by weight, preferably 0.01 to 15% by weight, more preferably 0.1 to 10% by weight, particularly preferably 0.3 to 5% by weight, most preferably 0.5 to 3% by weight, e.g. 1 and / or 2% by weight, and coupler components in an amount of 0.005 to 20% by weight, preferably 0.01 to 15% by weight, more preferably 0.1 to 10% by weight, particularly preferably 0 , 3 to 5% by weight, most preferably 0.5 to 3% by weight, e.g. 1 and / or 2 wt .-%, each based on the total oxidation colorant.
  • developer components and coupler components are generally used in approximately equimolar amounts (taking into account the number of reactive centers in the respective components). If the equimolar 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 colorant additionally contains at least one substantive dye.
  • 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
  • the agents according to the invention can also contain a cationic direct dye.
  • a cationic direct dye is particularly preferred.
  • 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
  • the compounds of the formulas (DZl), (DZ3) and (DZ5) are very particularly preferred cationic direct dyes of group (c).
  • the cationic direct dyes, which are sold under the trademark Arianor ® are, according to the invention also particularly preferred substantive dyes.
  • 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 agents according to the invention can also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten tree bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • the agents according to the invention preferably contain the substantive dyes in an amount of 0.005 to 20% by weight, preferably 0.01 to 15% by weight, more preferably 0.1 to 10% by weight, particularly preferably 0.3 to 5 % By weight, most preferably 0.5 to 3% by weight, e.g. 1 and / or 2 wt .-%, based on the total oxidation colorant.
  • oxidation dye precursors or the substantive dyes are in each case uniform compounds. Rather, in the hair colorants according to the invention, due to the production processes for the individual dyes, further components may also 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 oxidation dye precursors can be incorporated into a cosmetically suitable, for example water-containing carrier.
  • a cosmetically suitable for example water-containing carrier.
  • Such carriers are for the purpose of hair coloring, for example creams, emulsions, gels or also surfactant-containing foaming solutions, for example shampoos, Foam aerosols or other preparations that 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, both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle. In many cases, however, it has proven advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • the agents according to the invention preferably contain surfactants in an amount of 0.1 to 30% by weight, preferably 1 to 20% by weight and particularly preferably 2 to 10% by weight.
  • 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 a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • anionic group such as 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.
  • 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 and / or branched fatty acids with 8 to 22 ° C.
  • Sulfosuccinic acid mono- and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid mono-alkyl polyoxyethyl esters with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkanesulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon 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, O) ⁇ -SO 3 H, in which R is one 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
  • 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 2 -carboxylic acids, such as oleic acid, stearic acid , Isostearic acid and palmitic acid.
  • the agents according to the invention can preferably contain anionic surfactants in an amount of 0.5 to 30% by weight, preferably 1 to 20% by weight.
  • Zwitterionic surfactants are those surface-active compounds which have 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 N-alkyl-N, N dimethylammonium glycinates, for example cocoalkyl dimemylammoniumglycinat, N-acyl-aminopropyl-N, N-dimethylammonium glycinates, for example cocoacylaminopropyl dimethylammom 'umglycinat, and 2- A ⁇ kyl-3-carboxymethyl-3-hydroxyethyl imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group and cocoacylaminoethylhydroxyethylcarboxymethylglycineate
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the INCI
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C 8 . 18 -alkyl or -acyl group in the molecule contain at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts.
  • suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N- alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-
  • Alkyltaurines N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylamino propionate and C 12 . 18 acylsar cosm.
  • the agents according to the invention can preferably contain ampholytic surfactants in an amount of 0.1 to 20% by weight, preferably 1 to 10% by weight.
  • Nonionic surfactants contain z as a hydrophilic group.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such connections are, for example
  • Esters e.g. with tartaric acid and / or citric acid
  • the agents according to the invention can preferably contain nonionic surfactants in an amount of 0.1 to 30% by weight, preferably 1 to 20% by weight.
  • cationic surfactants are 'compounds existed in particular, quaternary Ammom. Preference is given to ammonium halides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and Trialkylmemylammom 'umchloride, for example cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, Lauryldimethylammomumchlorid, Lauryldimemylbenzylammoniumchlorid and Tricetyl- methylammomumchlorid.
  • 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 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 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80).
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimemylamine available under the name Tego Amid ® S 18, are characterized in particular by their good biodegradability.
  • fatty acid amidoamines such as the stearylamidopropyldimemylamine available under the name Tego Amid ® S 18, are characterized in particular by their good biodegradability.
  • biodegradability are quaternary Esterasticen, so-called “esterquats”, such as those sold under the trademark Stepantex ® hy ⁇ lroxyalkyldialkoyloxyalkyl methyl-ammom 'ummethosulfate as well as the products marketed under the trade name Dehyquart ® products such as Dehyquart ® AU-46th
  • 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 agents according to the invention can preferably contain cationic surfactants in an amount of 0.1 to 20% by weight, preferably 1 to 10% by weight.
  • the compounds with alkyl groups used as surfactants 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.
  • anionic surfactants in combination with zwitterionic surfactants can be particularly preferred.
  • compositions which additionally contain a cationic polymer are also preferred according to the invention.
  • the permanent cationic polymers are preferred among the cationic polymers.
  • polymers which have a cationic group irrespective of the pH of the composition are referred to as “permanently cationic”. These are usually polymers that contain a quaternary nitrogen atom, for example in the form of an ammonium group.
  • 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, polysiloxanes with quaternary groups, such as, 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 (Manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-
  • 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 vinyl pyrrolidone with quaternized derivatives of dialkylamino acrylate and methacrylate such as, for example, vinyl pyrrolidone-dimethylaminomethacrylate copolymers quaternized with diethyl sulfate.
  • Such compounds are available under the names Gafquat ® 734 and Gafquat ® 755 commercially Vinylpyirolidon-Vmylimidazoliummethochlorid copolymers, such as those offered under the names Luviquat ® FC 370, FC 550, FC 905 and HM 552, quaternized polyvinyl alcohol, as well as the under the names Polyquaternium 2, Polyquaternium 17, Polyquaternium 18 and Polyquaternium 27 known polymers with quaternary nitrogen atoms in the main polymer chain.
  • cationic polymers those under the names Polyquaternium-24 (commercial product e.g. Quatrisoft ® LM 200), Polyquatemium-32, Polyquaternium-35 and Polyquaternium-37 (commercial products e.g. Salcare ® SC 92 and Salcare ® SC 95) known polymers.
  • Copolymer 845 manufactured by the manufacturer: ISP
  • Gaffix ® VC 713 manufactured by the 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.
  • Katiom cellulose derivatives, in particular the commercial product Polymer ® JR 400, and polymers of the type Polyquaternium-2, in particular the commercial product Mirapol ® Al 5, are very particularly preferred cationic polymers.
  • the agents according to the invention can preferably contain cationic polymers in an amount of 0.1 to 10% by weight, preferably 0.2 to 5% by weight.
  • amphopolymers can also be used as an alternative to the cationic polymers.
  • Ampho-polymers are amphoteric polymers, ie polymers that contain both free amino groups and free - COOH or SO 3 H groups in the molecule and are capable of forming internal salts, zwitterionic polymers that contain quaternary ammonium groups and - COO " - or
  • Amphoporymer 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
  • Amphopolymers are composed of unsaturated carboxylic acid (e.g. acrylic and methacrylic acid), cationically derivatized unsaturated carboxylic acid (e.g.
  • acrylamidopropyltrimethylammonium chloride and optionally other ionic or nonionic monomers, such as in German Offenlegungsschrift 39 29 973 and the prior art cited therein.
  • Terpolymers of acrylic acid, methyl acrylate and methacrylamidopropyltrimom ' chloride, as are commercially available under the name Merquat ® 2001 N, as well as the commercial product Merquat ® 280 can also be used according to the invention.
  • Particularly preferred polymers are, for example, acrylantrdopropytrimemylainmoniumchlori ⁇ VAcrylat copolymers and / or octylacrylamide memyl -methacryla ⁇ / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers.
  • the agents according to the invention can preferably contain amphopolymers in an amount of 0.1 to 10% by weight.
  • the agents according to the invention likewise preferably contain at least one non-ionic or anionic polymer with thickening properties.
  • Preferred are optionally crosslinked polyacrylic acids, cellulose derivatives, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, and xanthan gum.
  • the agents according to the invention can preferably contain nonionic and / or anionic polymers in an amount of 0.1 to 25% by weight.
  • 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 polyvinyl alcohol, stericants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, and silicone oils,
  • 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,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol,
  • Anti-dandruff agents such as piroctone olamine and zinc omadine, other substances for adjusting the pH value,
  • Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and their salts, plant extracts and vitamins, cholesterol, light stabilizers,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters, 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
  • Blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air as well as antioxidants.
  • the constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose;
  • emulsifiers are used in concentrations of 0.1 to 30% by weight, preferably 0.2 to 10% by weight, particularly preferably 0.3 to 5% by weight, most preferably 0.5 to 3% by weight. %
  • thickeners in concentrations of 0.1 to 25% by weight, preferably 0.2 to 10 % By weight, particularly preferably 0.3 to 5% by weight, most preferably 0.5 to 2% by weight, in each case based on the total amount of the colorant.
  • the oxidative development of the coloring can take place with atmospheric oxygen.
  • a chemical oxidizing agent can also be used. This is particularly preferred 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 (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 enzymes can serve to enhance the effect of small amounts of oxidizing agents present.
  • An example of such an enzymatic process is the procedure 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 expediently mixed with the preparation from the oxidation dye precursors immediately before hair coloring.
  • the resulting ready-to-use hair color preparation should have a pH in the range from 6 to 13, preferably in a range from 8 to 12, most preferably in a range from 9 to 11. It is particularly preferred to use the hair dye in a weakly alkaline environment.
  • the application temperatures can range between 15 and 40 ° C. After an exposure time of approx. 30 minutes, 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.
  • Another object of this invention is the use of the aforementioned agents for dyeing keratin fibers.
  • Triethylamine 10.5 gl, 4-bis (3-aminopropoxy) butane and 14.4 g l-fluoro-4-nitrobenzene added. After stirring for 20 h at 80 ° C., the mixture was poured onto 1 l of ice water after cooling. The resulting precipitate was filtered off and washed with water. The mixture was then dried at 50 ° C in a vacuum. Yield: 21.3 g (95%) mp: 112-115 ° C
  • the substances to be investigated were suspended separately from the developer and coupler in distilled water or dissolved with heating. 1/400 mol developer or coupler were used in each case. Then ammonia ( ⁇ 1 ml; 25% ammonia solution) was added until the pH was between 9 and 10. A solution was created by adding Ammomak.
  • the dissolved developers and couplers were worked into the hot cream in succession.
  • the mixture was then made up to 97 g with distilled water and the pH was adjusted to 9.5 with Ammomak. After filling up to 100 g with distilled water, the mixture was stirred cold ( ⁇ 30 ° C.), a homogeneous cream being formed.
  • the cream was diluted as follows for the different colors:
  • a lock of hair (80% gray; 330 mg to 370 mg in weight) was added to each of the mixtures thus obtained.
  • the mixtures and the strands of hair were then each placed on a watch glass and the strands of hair were well embedded in the coloring creams. After 30 minutes ( ⁇ 1 minute) of exposure at room temperature, the strands of hair were removed and washed with Texapon EVR ® (Na lauryl ether sulfate) until the excess color was removed.
  • the strands of hair were air-dried and their color was determined and noted under the daylight lamp (color testing device HE240A) (Taschenlexikon der Weg Weg, A. Kornerup and JH Wanscher, 3rd unchanged edition 1981, MUSTER-SCHMIDT Verlag; Zurich, Göttingen).

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Abstract

La présente invention concerne de nouvelles p-phénylènediamines pontées, leur utilisation comme composants révélateurs dans des colorants d'oxydation ainsi que de nouveaux colorants d'oxydation, contenant les p-phénylènediamines pontées susmentionnées. Cette invention concerne également un procédé de production de p-phénylènediamines pontées. Dans le cadre de la présente invention, il a été démontré que des p-phénylènediamines, pontées par un polyoxyalkyle, de formule (I) s'utilisent comme composants révélateurs, de façon remarquable, dans des colorants d'oxydation.
EP02798707A 2001-09-07 2002-09-04 P-phenylendiamines pontees Pending EP1423355A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10144226A DE10144226A1 (de) 2001-09-07 2001-09-07 Neue verbrückte p-Phenylendiamine
DE10144226 2001-09-07
PCT/EP2002/009875 WO2003024917A1 (fr) 2001-09-07 2002-09-04 P-phenylendiamines pontees

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EP1423355A1 true EP1423355A1 (fr) 2004-06-02

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US (1) US20040199018A1 (fr)
EP (1) EP1423355A1 (fr)
JP (1) JP2005503409A (fr)
DE (1) DE10144226A1 (fr)
WO (1) WO2003024917A1 (fr)

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GB0324159D0 (en) * 2003-10-15 2003-11-19 Glaxo Group Ltd Novel compounds
FR2864533B1 (fr) 2003-12-29 2006-02-17 Oreal P-phenylenediamine secondaire double particuliere, composition tinctoriale la comprenant et procede de coloration mettant en oeuvre la composition
US7413580B2 (en) 2005-06-29 2008-08-19 L'oreal S.A. Double para-phenylenediamines joined by a linker arm substituted with one or more carboxylic radicals and/or derivatives and use in dyeing
US20070011828A1 (en) * 2005-06-29 2007-01-18 Stephane Sabelle Novel double para-phenylenediamines joined by a branched aliphatic group and method of dyeing keratin fibers
FR2887878B1 (fr) * 2005-06-29 2010-09-24 Oreal Nouvelles para-phenylenediamines doubles reliees par un bras de liaison comportant un radical cyclique sature et utilisation en coloration
US7422609B2 (en) 2005-06-29 2008-09-09 Oreal Double para-phenylenediamines joined by an aromatic group for dyeing keratin fibers
ATE554081T1 (de) 2007-09-06 2012-05-15 Glaxo Group Ltd Piperazinderivate mit affinität zum histamin-h3- rezeptor
CN105902404A (zh) * 2016-06-14 2016-08-31 知识产权全资有限公司 强发成分以及强发的方法
EP3727599B8 (fr) 2017-12-21 2023-11-22 Laboratoire Biosthetique Kosmetik GmbH & Co. KG Agent de coloration de fibres de kératine contenant une combinaison d'un dérivé de p-phénylène et de 2,7-naphthaline diol et son utilisation pour déduire la dominante jaune dans la chevelure

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LU56631A1 (fr) * 1968-08-02 1970-02-02
DE3723354A1 (de) * 1987-07-15 1989-01-26 Henkel Kgaa Sulfatierte hydroxy-mischether, verfahren zu ihrer herstellung und ihre verwendung
DE3725030A1 (de) * 1987-07-29 1989-02-09 Henkel Kgaa Oberflaechenaktive hydroxysulfonate
DE3942574A1 (de) * 1989-12-22 1991-06-27 Basf Ag Polytetrahydrofuranderivate mit endstaendigen aromatischen gruppen
US5260484A (en) * 1989-12-22 1993-11-09 Basf Aktiengesellschaft Polytetrahydrofuran derivatives having terminal aromatic groups
DE4234887A1 (de) * 1992-10-16 1994-04-21 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 4,5-Diaminopyrazolderivaten sowie neue 4,5-Diaminopyrazolderivate und Verfahren zu ihrer Herstellung
FR2733749B1 (fr) * 1995-05-05 1997-06-13 Oreal Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
DE19707545A1 (de) * 1997-02-26 1998-08-27 Henkel Kgaa Neue Diazacycloheptan-Derivate und deren Verwendung

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WO2003024917A1 (fr) 2003-03-27

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