WO1999018917A2 - Agent for dyeing fibers containing keratin with a concentration of dehydroascorbic acid content - Google Patents

Agent for dyeing fibers containing keratin with a concentration of dehydroascorbic acid content Download PDF

Info

Publication number
WO1999018917A2
WO1999018917A2 PCT/EP1998/006310 EP9806310W WO9918917A2 WO 1999018917 A2 WO1999018917 A2 WO 1999018917A2 EP 9806310 W EP9806310 W EP 9806310W WO 9918917 A2 WO9918917 A2 WO 9918917A2
Authority
WO
Grant status
Application
Patent type
Prior art keywords
amino
ñure
hydroxy
methyl
compounds
Prior art date
Application number
PCT/EP1998/006310
Other languages
German (de)
French (fr)
Other versions
WO1999018917A3 (en )
Inventor
Hinrich Möller
Horst Höffkes
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

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/67Vitamins
    • A61K8/676Ascorbic acid, i.e. vitamin C
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/62Three oxygen atoms, e.g. ascorbic acid
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS, OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS, OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/30Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts

Abstract

The invention relates to an agent for dyeing fibers containing keratin. Said agent contains dehydroascorbic acid of formula (I) and at least one compound having a primary or secondary amino group or a hydroxy group selected from primary or secondary aliphatic or aromatic amines, heterocyclic compounds containing nitrogen, α- to φ- amino acids, oligopeptides and aromatic hydroxy compounds with 2 to 9 amino acids, and/or at least one CH active compound.

Description

"Formulations for coloring keratin-containing fibers with a content of dehydroascorbic"

The invention relates to an agent for coloring keratin fibers containing dehydroascorbic acid in combination with reactive components, the use of this agent for coloring keratin fibers and to a process for dyeing keratin-containing fibers.

For the dyeing of keratin fibers, for. B. hair, wool or furs, either direct dyes or oxidation dyes which are formed by oxidative coupling of one or more developer components with one another or with one or more coupler components generally used. Coupler and developer components are also referred to as oxidation dye precursors.

The developer components primary aromatic amines are commonly used with another in the para or ortho position free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof.

Special representatives are, for example, p-phenylenediamine, p-toluylenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- (2,5-diaminophenyl ) -ethanol, 2- (2,5-diaminophenoxy) -ethanol, 1-phenyl-3-carboxy-amido-4-amino-5-pyrazolone, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-Thamino-4-hydroxypyrimidine.

The coupler components usually m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are used. As coupler substances are in particular α-naphthol, 1 are, droxynaphthalin 5-, 2,7-, and 1, 7-dihydroxyacetone, 5-amino-2-methylphenol, m-aminophenol, resorcinol, Resorcinmono- methyl ether, m-phenylenediamine, 2 , 4-diaminophenoxyethanol, 1-phenyl-3-methyl-pyramid-.Zolon-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2,4-diaminophenoxy) propane, 2-resorcinol Chlorre- , 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol and 5-methylresorcinol.

With regard to further customary dye components, is made expressly to the series "Dermatology", edited by Ch. Culnan, H. Maibach, Marcel Dekker Inc., New York, Basel, 1986, Vol. 7, Ch. Zviak, The Science of Hair Care, . chapter 7, pages 248-250 (direct dyes), and chapter 8, pages 264 -. 267 (oxidation dyes), and the "European inventory of cosmetic raw Materials", 1996, published by the European Commission, available in diskette form from the Bundesverband der deutschen Commerce and Industry for pharmaceuticals, health products and personal care products eV, Mannheim, reference is made.

With oxidation dyes intensive colors with good fastness properties can indeed be achieved, however, the development of color is generally under the influence of oxidizing agents such as H 2 O 2, which may in some cases damage to the fibers. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors can occasionally have a sensitizing effect in people with sensitive skin. Direct dyes are applied under more conditions, but their disadvantage is that the colors often have inadequate fastness properties.

Object of the present invention is to provide a colorant for keratin fibers, in particular human hair, which are at least equivalent in terms of color depth, the gray coverage and fastness properties qualitatively with conventional oxidation, but are not 2 dependent necessarily on oxidizing agent such as H 2 O. Another object of the present invention is to provide colorant with which a wide variety can be obtained in the color shades. A staining of the skin should be avoided. In addition, the colorants must have no or only a very low awareness-raising potential. Surprisingly, it was found that combinations of Dehydroascor- ascorbic and at least one other component are outstandingly suitable for coloring keratin fibers. The agents provide colorations with excellent brilliance and depth and lead to various shades. The use of-oxidizing agents is not required, but it should not be ruled out in principle.

The present invention accordingly provides an agent for coloring keratin fibers containing

A) dehydroascorbic acid of the formula (I)

Figure imgf000005_0001

and

B) at least one compound with a primary or secondary amino group or hydroxy group chosen from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, α- to ω-amino acids, constructed from 2 to 9 amino acids in oligopeptides and aromatic hydroxy compounds, and / or at least one CH-active compound.

Keratin fibers wool, furs, feathers and in particular human hair to understand. The colorants according to the invention can in principle also for dyeing other natural fibers such as cotton, jute, sisal, linen or silk, modified natural fibers such as regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as polyamide, polyacrylonitrile, polyurethane and polyester fibers. The inventive compositions containing the compounds of the components A and B preferably in an amount of 0.03 to 65, particularly 1 to 40 mmol, each based on 100 g of the total colorant contained.

Under the present invention also such embodiments are, containing the reaction products of the individual components A and B.

Dehydroascorbic containing as component A is a known compound whose preparation is described in the literature and is commercially available.

Suitable compounds having primary or secondary amino group as component B are for example primary aromatic amines, such as N, N-dimethyl, N, N-diethyl-, N- (2-hy- droxyethyl) -N-ethyl-, N, N-bis - (2-hydroxyethyl) -, N- (2-methoxyethyl), 2,3-, 2,4-, 2,5- dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy -4-morpholinoani- lin dihydrobromide, 2-, 3-, 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, o-, p-phenylenediamine, o-tolylenediamine, 2, 5-diaminotoluene, - phenol, -phenethol, 4-amino-3-methyl phenol, 2- (2,5-diaminophenyl) ethanol, 2,4-di- aminophenoxyethanol, 2- (2,5-diaminophenoxy) -ethanol, 4-methylamino-, 3-amino-4- (2'-hydroxyethyloxy) -, 3,4-Methylendiamino-, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro-, 4-methylamino-, 2- methyl-5-amino-, 3-methyl-4-amino-, 2-methyl-5- (2-hydro- xyethylamino) -, 6-methyl-3-amino-2-chloro-, 2-methyl-5- amino-4-chloro-, 3,4-methylenedi oxy, 5- (2-hydroxyethylamino) -4-methoxy-2-methyl-, 4-amino-2-hydroxymethylphenol, 1, 3-D iAmino-2,4-dimethoxybenzene, 2-, 3-, 4-aminobenzoic acid, -phenylacetic acid, 2,3-, 2,4-, 2,5-, 3,4-, 3,5-diaminobenzoic acid, 4-, 5-aminosalicylic acid, droxy- 3-amino-4-hy-, 4-amino-3-hydroxy-benzoic acid, 2-, 3-, 4-aminobenzenesulfonic acid, 3-amino-4-hydroxybenzoisulfonsäure, 4-amino-3-hydroxynaphthalene -1-sulfonic acid, 6-amino-7-hydroxynaphthalene-2-sulfonic acid, 7-amino-4-hydroxynaphthalene-2-sulfonic acid, 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid, 3-amino-2-naphthoic acid , 3-amino phthalic acid, 5-aminoisophthalic acid, 1, 3,5-, 1, 2,4-triaminobenzene, 1, 2,4,5-tetraamino benzene, 2,4,5-Thaminophenol, Pentaaminobenzol, Hexaaminobenzol, 2,4,6-triamine oresorcin, 4,5-Diaminobrenzcatechin, 4,6-Diaminopyrogallol, 3,5-diamino-4-hydroxy-catechol, aromatic anilines or phenols with a further aromatic radical as shown in the formula II are shown

Figure imgf000007_0001

( ")

in which R 1 is a hydroxy or an amino group which droxyalkyl- 1-4 hydrogencarbonates by C M alkyl, C or C ^ alkoxy-C ^ alkyl may be substituted,

R 2, R 3, R 4, R 5 and R 6 is hydrogen, a hydroxy or an amino group, by a C 1-4 alkyl, C 1-4 hydroxyalkyl, C 1-4 aminoalkyl, or C ^ alkoxy-C M alkyl group may be substituted, represent a carbon doer sulfonic acid group, and

Z is a direct bond, a saturated or unsaturated, optionally pen by Hydroxygrup- substituted carbon chain having 1 to 4 carbon atoms, a carbonyl, sulfonic fonyl- or imino group, an oxygen or sulfur atom, or a group having the

formula III

Z- (CH 2 -Y-CH 2 -Z ') 0 (III)

in which Y is a direct bond, a CH 2 - or CHOH group,

Z and Z 'independently represent an oxygen atom, an NR 7 group, wherein R is 1-4 alkyl group 7 is hydrogen, a C 1-4 alkyl, or hydroxy-C, the group

O- (CH 2) p -NH or NH- (CH 2) p.-O, wherein p and p 'are 2 or 3, and are o is a number from 1 to 4, such as 4,4'-diaminostilbene , 4,4'-diaminostilbene-2,2'-disulfonic acid, mono- or

di-Na salt, 4-amino-4'-dimethylaminostilben, 4,4'-diaminodiphenylmethane, sulfide, - sulfoxide, -amine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, - diphenylether, 3,3 ', 4,4'-Tetraaminodiphenyl, 3,3', 4,4'-tetraamino-benzophenone, 1, 3- bis (2,4-diaminophenoxy) propane, 1, 8-bis - (2,5-diaminophenoxy) -3,6-dioxaoctane, 1, 3-bis- (4-aminophenylamino) -propane, -2-propanol, 1, 3-bis [N- (4-aminophenyl) -2 hydroxy-ethylamino] -2-propanol, N, N-bis [2- (4-aminophenoxy) ethyl] methylamine, N-phenyl-1, 4- phenylenediamine. The abovementioned compounds may exist in free form and in the form of their physiologically acceptable salts, especially salts of inorganic acids such as hydrochloric or sulfuric acid, are used.

Suitable nitrogen-containing heterocyclic compounds are, for example 2-, 3-, 4-amino-, 2-amino-3-hydroxy-, 2,6-diamino-, 2,5-diamino-, 2,3-diamino-, 2-dimethylamino -5- amino-, 2-methylamino-3-amino-6-methoxy-, 2,3-diamino-6-methoxy-, 2,6-dimethoxy-3,5-diamino-, 2,4,5-triamino -, 2,6-dihydroxy-3,4-dimethylpyridine, 2,4-diamino-dihydroxy-5,6, 4,5,6-triamino-4-hydroxy-2,5,6-triamino, 2 -hydroxy-4,5,6-triamino, 2,4,5,6-tetraamino, 2-methylamino-4,5,6-triamino, 2,4-, 4,5-diamino-, 2- amino-4-methoxy-6-methyl-pyrimidine, 3,5-diaminopyrazole, -1, 2,4-triazole, 3-amino-, 3-amino-5- hydroxypyrazole, 2-, 3-, 8-aminoquinoline 4-amino-quinaldine, 2-, 6-aminonicotinic acid, 5-aminoisoquinoline, 5-, 6-aminoindazole, 5-, 7-amino-benzimidazole, benzothiazole, 2,5-dihydroxy-4-morpholinoaniline and indole and indoline derivatives such as 4-, 5-, 6-, 7-amino-indole, 5,6-dihydroxyindole, 5,6-dihydroxyindoline and 4-hydroxyindoline. The abovementioned compounds may exist in free form and in the form of their physiologically acceptable salts, for. B. be used as salts of inorganic acids such as hydrochloric or sulfuric acid.

As amino acids, preferably all naturally occurring and synthetic α-amino acids are suitable, for example, by hydrolysis from vegetable or animal proteins, for example collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein, accessible amino acids. Here can be used both acidic alkaline amino acids. Preferred amino acids are Argi- nin, histidine, tyrosine, phenylalanine, DOPA (dihydroxyphenylalanine), ornithine, lysine and tryptophan. But other amino acids such as 6-aminocaproic acid can be used.

The oligopeptides can thereby be naturally occurring or synthetic oligopeptides, but also the oligopeptides present in polypeptide or protein, provided they have one for use in the inventive colorants sufficient water solubility. Examples such as glutathione or the oligopeptides present in the hydrolyzates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein can be mentioned. Preference is given to the use is in conjunction with compounds having primary or secondary amino group or aromatic hydroxy compounds.

Suitable aromatic hydroxy compounds are, for example, 2-, 4-, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2-, 3-, 4-methoxy-, 3 dimethylamino, 2- (2-hy- droxyethyl) -, 3,4-methylenedioxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, -phenylessig- acid, gallic acid, 2,4,6-trihydroxybenzoic acid, -acetophenone, 2 -, 4-chlororesorcinol, 1-naphthol, 1, 5-, 2,3-, 2,7-dihydroxynaphthalene, 6-dimethylamino-4-hydroxy-2-naphthenic thalinsulfonsäure, 3,6-dihydroxy-2,7- naphthalene sulfonic acid.

CH-active compounds as 2,3,3-tetramethyl-3H-indolium iodide, 1 can be exemplified 1, 2,3,3-tetramethyl-3H-indolium-p-toluenesulfonate, 1,2,3,3-tetramethyl - thyl-3H-indolium methanesulfonate, Fischer's base (1, 3,3-trimethyl-2-methylenindo- lin), 2,3-dimethyl-benzothiazolium iodide, 2,3-dimethyl benzothiazolium-p-toluenesulfonate, rhodanine, rhodanine -3-acetic acid, 1-ethyl-2-chinaldiniumiodid, 1-methyl-2-chinaldiniumiodid barbituric acid, thiobarbituric acid, 1, 3-Dimethylthiobarbitursäure, diethyl thiobarbituric acid, oxindole, 3-lndoxylacetat, coumaranone and 1-methyl-3- phenyl-2-pyramid-zolinon.

In all colorants several different coloring substances can work in conjunction; Likewise, several different components from the groups of compounds having primary or secondary amino group, nitrogen-containing heterocycles, aromatic hydroxy compounds or amino acids may be used together.

It has been found advantageous the compositions of the invention alkali metal salts or ammonium salts of C -carboxylic acids or C Ce-hydroxycarboxylic acids and carbonic add. Examples of such salts include formate, acetate, propionate, butyrate, valerate, caproate, glycolate, lactate and carbonate. As ammonium cations also Hydroxyalkylammoniumkationen can be used. In the presence of oxidizing agents such as H 2 O 2, in the inventive use of dehydroascorbic can be dispensed with. However, it may be desirable under certain circumstances, to the agents to achieve nuances which are lighter than the keratin fibers to be dyed, add hydrogen peroxide or other oxidizing agents. Oxidizing agents are generally used in an amount of 0.01 to 6 wt .-%, based on the application solution. A preferred for human hair oxidant is H 2 O 2.

The colorants present invention provide a wide range of shades ranging from yellow to yellow brown, orange, brown orange, medium brown, dark brown, purple, dark purple to black; the fastness properties are excellent, the sensitization potential very low.

In a preferred embodiment, the colorants according to the invention to further modify the color nuance additionally contain customary direct dyes in addition to the present invention included compounds trophenylendiamine for example, from the group of Ni, nitroaminophenols, anthraquinones or indophenols, such as under the International names or commercial names of HC Yellow 2, HC Yellow 4, HC Yellow 6, Basic Yeliow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, disperse Violet 4, disperse Black 9, Basic Brown 16 and Basic Brown 17 and also picramic acid, 2-amino-6-chloro-4-nitrophenol, 4-amino-2-nitro-diphenylamine-2'-carboxylic acid, 6-nitro -1, 2,3,4-tetrahydroquinoxaline, 4-N-ethyl-1, 4-bis (2'-hydroxyethylamino) -2-nitrobenzene hydrochloride and 1-methyl-3-nitro-4- (2'-hydroxy - ethyl) aminobenzene. The agents of the invention according to this embodiment contain the dyes preferably in an amount of 0.01 to 20 wt .-%, based on the total colorant.

The colorants according to the invention can be black included, chamomile blossom, sandalwood, black tea, buckthorn bark, sage, logwood, madder root, Ca Techu, cedar and alkanet also contain naturally occurring dyes such as henna red, henna neutral, henna. It is not necessary that the oxidation dye precursors or the substantive dyes optionally present to be single compounds. Rather, may be caused by containing the manufacturing processes for the individual dyes, in minor amounts of other components in the novel dyes, to the extent they do not adversely affect the coloring result or eg toxicological, must be ruled out for other reasons.

The colorants according to the invention already provide intense colorations even at physiologically compatible temperatures of less than 45 ° C. They are therefore particularly suitable for dyeing human hair. For use on human hair, the colorants may be typically incorporated into an aqueous cosmetic carrier. Suitable water-containing cosmetic carriers are, for example, creams, emulsions, gels or even surfactant-containing foaming solutions, such as shampoos or other preparations, that are suitable for use on keratin fibers. it is also possible if necessary to incorporate the colorants into anhydrous carriers.

The colorants of the invention can include all known in such preparations active ingredients, additives and auxiliaries. In many cases, the colorants contain at least one surfactant, both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases it has proved advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.

Anionic surfactants suitable for use on the human body anionic surfactants are present in inventive preparations. These are characterized by a water solubilizing anionic group such. Example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having approximately 10 to 22 C-atoms. In addition, the molecule may col- Gly or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups. Examples of suitable anionic surfactants, each in the form of sodium, potassium and ammonium salts and the mono-, di- and Trialkanolam- ammonium salts having 2 or 3 carbon atoms in the alkanol group: linear fatty acids having 10 to 22 carbon atoms (soaps), ether carboxylic acids of formula RO- (CH 2 -CH 2 O) x -CH 2 COOH, = in which R is a linear alkyl group having 10 to 22 carbon atoms and x is 0 or 1 to 16, acyl sarcosides having 10 to 18 carbon atoms in the acyl group, acyl taurides having 10 to 18 carbon atoms in the acyl group, acyl isethionates containing 10 to 18 carbon atoms in the acyl group, sulfosuccinic acid mono- and dialkyl esters containing 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid -alkylpolyoxyethylester having 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkane sulfonates having 12 to 18 C atoms, linear alpha-olefin sulfonates containing 12 to 18 carbon atoms, alpha-sulfofatty acid methyl esters of fatty acids having 12 to 18 C -atoms, alkyl sulfates and alkyl polyglycol of Forme l RO (CH 2 -CH 2 O) x -SO 3 H, = in which R is a preferably linear alkyl group having 10 to 18 carbon atoms and x is 0 or 1 to 12,

Mixtures of surface-active hydroxysulfonates according to DE-A-37 25 030, sulfated hydroxyalkylpolyethylene and / or hydroxyalkylene propylene glycol ethers according to DE-A-37 23 354,

Sulfonates of unsaturated fatty acids having 12 to 24 carbon atoms and 1 to 6 double bonds according to DE-A-39 26 344,

Represent ester of tartaric acid and citric acid with alcohols which are addition products of approximately 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols having 8 to 22 carbon atoms.

Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 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 especially unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.

Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one in the molecule - wear or -SO 3 () group - COO (). Particularly suitable zwitterionic surfactants are the betaines such as N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyl dimethylammonium, N-acyl-aminopropyl-N, N-dimethyl- ammoniumglycinate, for example cocoacylaminopropyl dimethyl ammonium, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines carboxymethylglycinat each having 8 to 18 carbon atoms in the alkyl or acyl group as well as the Kokosacylaminoethylhydroxyethyl-. A preferred zwitterionic surfactant is known under the CTFA name Cocamidopropyl Betaine fatty acid amide derivative.

Ampholytic surfactants are surface-active compounds which, in addition to a C8-18 alkyl or acyl group in the molecule at least one free amino group and at least one -COOH or -SO3H group and are capable of forming inner salts. Examples of suitable ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkylaminobutyric acids, N-Alkyliminodi- propionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-Alkylsar- cosine, 2-alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 C atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C12-18 acyl sarcosine.

Non-ionic surfactants contain as hydrophilic group, for. B. a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether groups. Such compounds are for example

Addition products of 2 to 30 mol ethylene oxide and / or 0 to 5 mol propylene oxide onto linear fatty alcohols containing 8 to 22 carbon atoms, onto fatty acids containing 12 to 22

C-atoms and to alkylphenols containing 8 to 15 carbon atoms in the alkyl group,

C 12th 22 fatty acid monoesters and diesters of addition products of 1 to 30 mol

Ethylene oxide onto glycerol,

Figure imgf000013_0001
mono- and oligoglycosides and ethoxylated analogs thereof,

Addition products of 5 to 60 mol ethylene oxide onto castor oil and hydrogenated

Castor oil,

Adducts of ethylene oxide with sorbitan

Adducts of ethylene oxide with fatty acid.

Examples of the usable in the inventive hair treatment compositions cationic surfactants are especially quaternary ammonium compounds. Preference is given to ammonium halides such as alkyl, umhloride Dialkyldimethylmoni- and trialkyl such. B. cetyltrimethylammonium, Stearylrimethylammoniumchlorid, distearyldimethylammonium,

Lauryldimethylammoniumhlorid, lauryldimethylbenzylammoniumchloride and Tricetyl- methyl ammonium chloride. Further inventively usable cationic surfactants are the quaternized Proteinydrolysate.

According to the invention are also suitable cationic silicone oils such as the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning 929 Emulsion (containing a hydroxylamino-modified silicone which is also known as amodimethicone), SM -2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil.RTM-Quat 3270 and 3272 (manufacturer: Th Goldschmidt; diquaternary polydimethylsiloxanes quaternization nium-80.).

Alkylamidoamine, particularly fatty acid as the stearylamidopropyldimethylamine obtainable under the name Tego Amid®S 18, are characterized by a good conditioning effect particularly by their good biological degradability ness from.

Also very readily biodegradable quaternary Esterverbindungen are so-called "esterquats", such as the methyl marketed under the trademark Stepantex ® hydroxyalkyldialkoyloxyalkylammoniummethosulfate.

An example of a suitable cationic surfactant quaternary sugar derivative is the commercially available product Glucquat®100 represents, according to CTFA nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride".

When used as surfactants compounds with alkyl groups may be single compounds. However, it is generally preferred to proceed in the preparation of these substances from native vegetable or animal raw materials so that substance mixtures with different alkyl chain lengths dependent upon the particular raw material. The surfactants which are addition products of ethylene and / or propylene oxide with fatty alcohols or derivatives of these addition products, both products having a "normal" homologue distribution or those may be used with a narrow homolog distribution. "Normal" homologue distribution are mixtures of homologues are understood to mean that one metal hydroxides in the reaction of fatty alcohol and Alkyienoxid using alkali metals, alkali metal or alkali metal alcoholates as catalysts obtained. Narrowed homolog distributions are obtained, however, if hydrotalcite, alkaline earth 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 may be preferred.

Other active substances, auxiliaries and additives are, for example, nonionic polymers such as vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternized ary groups, dimethyldiallylammonium chloride polymers , acrylamide-dimethyldiallylammonium chloride copolymers, quaternized with diethyl sulfate dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-vinyl imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as Acrylamidopropyl- trimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate /tert.-Butylaminoethylmethacrylat/2-Hydroxypropylmethacrylat-Copo- mers, anionic polymers such as polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers Vinyiacetat / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert

Butylacrylamide terpolymers,

Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean flour, linseed, dextrans,

Cellulose derivatives, eg. Methyl cellulose, hydroxyalkyl cellulose and carboxymethyl methylcellulose, starch fractions and derivatives, such as amylose, amylopectin and dex- trine, clays such. For example, bentonite or fully synthetic hydrocolloids such as polyvinyl lyvinylalkohol,

Structurants, such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example Sojale- cithin, egg lecithin and cephalins, and silicone oils,

Proteinhydroiysate, particularly elastin, collagen, keratin, milk protein, soy protein and wheat protein, their condensation products with fatty acids and quaternized Proteinhydroiysate, perfume oils, dimethyl isosorbide and cyclodextrins,

Solubilizing agents such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol,

Antidandruff active ingredients such as piroctone olamine and zinc Omadine, further substances for adjusting the pH,

Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidone and salts thereof, plant extracts and vitamins, cholesterol, light stabilizers,

Thickeners like Zuckerester, polyol esters or polyol alkyl ethers, fats and waxes, such as spermaceti, beeswax, montan wax, paraffins, fatty alcohols and fatty acid ester, fatty acid alkanolamides,

Complexing agents such as EDTA, NTA and phosphonic acids,

Swelling and penetration substances, such as glycerin, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates, imidazoles, tannins, pyrrole, opacifiers, such as latex,

Pearlescent agents such as ethylene glycol mono- and distearate,

Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO2 and air and antioxidants.

The components of the water-containing carrier are used for the preparation of the colorants according to the invention in amounts customary for this purpose; For example, emulsifiers used in concentrations of 0.5 to 30 wt .-%, and thickeners in concentrations of from 0.1 to 25 wt .-% of the total colorant. For the coloring result, it may be advantageous to add the colorants ammonium or metal salts. Suitable metal salts are, for example formates, carbonates, halides, sulfates, butyrates, valerates, caproates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of alkali metals such as potassium, sodium or lithium, alkaline earth metals such as magnesium, Caicium, strontium or barium, or of aluminum, manganese, iron, cobalt, copper or zinc, sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, - chloride and acetate are preferred. These salts are preferably present in an amount of 0.03 to 65, particularly 1 to 40 mmol, based on 100 g of the colorant as a whole.

The pH of the ready to use dyeing preparations is usually between 2 and 11, preferably 5 to 9

Another object of the present invention relates to the use of dehydroascorbic acid of the formula (I)

Figure imgf000017_0001

in aqueous or organic-aqueous solution in the presence of at least one compound with a primary or secondary amino group or hydroxy group chosen from primary or secondary aliphatic or aromatic amines, heterocyclic compounds, α- to ω-amino acids, composed of two to nine amino acids and aromatic hydroxy compounds oligopeptides and / or at least one CH-active compound for dyeing keratin-containing fibers. Another object of the present invention relates to a process for dyeing keratin fibers in which a colorant containing dehydroascorbic acid and the compounds of component B mentioned above are used as coloring components. To carry out the process of the invention, the colorants are usually applied in the presence of a water-containing cosmetic carrier in an amount of 100 g to the hair, left there for about 30 minutes and then rinsed out or washed out with a commercially available hair shampoo.

The compounds of the components A and B can either be applied simultaneously to the hair or else one after the other, it being immaterial which of the components applied first. The ammonium or metal salts optionally present can thereby be added to the first or the second component. may be an interval of up to 30 minutes between the application of the first and the second component. Also, a pretreatment of the fibers with the salt solution is possible.

The components A and B of the compositions of the invention may either be stored separately or together, either (anhydrous or aqueous) in a liquid to paste-like preparation or as a dry powder. If the components are stored together in a liquid preparation, they should be substantially anhydrous in order to reduce reaction of the components. In the separate storage of the reactive components are intimately mixed with one another only immediately before use. In the dry storage, a defined amount of hot (from 50 to 80 ° C) water is usually added prior to the application and a homogeneous mixture prepared.

Examples

Preparing a staining solution

There was prepared a slurry of 10 mM dehydroascorbic acid, 10 mmol of a compound of component B, 10 mM sodium acetate and one drop of a 20% fatty alkyl ether sulfate solution in 100 ml of water. The slurry was heated briefly to about 80 ° C and filtered after cooling, the pH was then adjusted to. 6

In this dye solution, a strand of 90% non-pretreated human hair graying was at 30 ° C for 30 minutes, is introduced. The dyed tress was then 30 sec. Rinsed with lukewarm water, dried (30-40 ° C) air stream in the warm and then combed. After that, the colorations were assessed visually in daylight.

The respective color shades and color depths are shown in the following tables.

The color depth was it rated on the following scale:

no or a very pale coloration

(+) Weak intensity

+ Average intensity

+ (+) ++ moderate to severe intensity strong intensity

++ (+) strong to very strong intensity +++ very strong intensity T able 1

Colorations with dehydroascorbic

Component B Färbenuance Farbti "

2,5-diaminotoluene x H 2 SO 4 violet brown ++ (+) 2,4,5,6-tetra x H 2 SO 4 brown yellow + 1, 8-bis- (2,5-diaminophenoxy) -3,6- dioxaoctane x 4 HCI blue black +++ 2-methylamino-3-amino-6-methoxypyridine x 2HCl orange brown ++ 2- (2,5-diaminophenyl) -ethanol x H 2 SO 4 violet brown + (+) N, N-bis - (2-hydroxyethyl) -p-phenylenediamine x HCI violet brown ++ 4,4'-diaminodiphenylamine x H 2 SO 4 violet black +++ 2,6-dimethoxy-3,5-diaminopyridine x 2HCl brown black +++

Claims

Patentanspr├╝che
1. means for Färben keratin-containing fibers, which enthält (A) Dehydroascorbinsäure of formula (I)
Figure imgf000021_0001
and
(B) at least one compound with prim├ñrer sekund├ñrer or amino group or hydroxy group, ausgew├ñhlt from prim├ñren sekund├ñren or aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, ╬▒- to ╧ë-Aminos├ñuren ​​from 2 to 9 Aminos├ñuren ​​constructed oligopeptides and aromatic hydroxy compounds, and / or at least one CH-active compound.
2. The composition according to claim 1, characterized in that daß the compounds of component B are ausgewählt from primären sekundären or amines from the group consisting of N- (2-hy- droxyethyl) -N-ethyl -, N- (2-methoxyethyl), 2,3-, 2,4-, 2,5-dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, N, N-bis (2- hydroxyethyl) -p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline dihydrobromide, 2-, 3-, 4-aminophenol, o-, p-phenylenediamine, 2,4-diaminophenoxyethanol, 2- (2,5-diaminophenyl ) -ethanol, 2,5-diaminotoluene, -phenol, -phenethol, 4-methylamino-, 3-amino-4- (2'-hy droxyethyloxy) -, 3,4-Methylendiamino-, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro-, 4-methylamino-, 3,4-methylenedioxy-, 3-methyl-4-amino-, 2-methyl-5- (2-hydroxyethylamino) -, 6-methyl-3 amino-2-chloro-, 6-methyl-3-amino-2-chloro-, 5- (2-hydroxyethylamino) -4-methoxy-2-methyl-, 4-amino-2-aminomethyl-phenol, 4- amino-2-hydroxymethyl-phenol, 3,4-methylenedioxyphenol, 1, 3-diamino-2,4-dimethoxybenzene, 2-, 3-, 4-aminobenzoic äure, -phenylessigsäure, 2,3-, 2,4-, 2,5-, 3,4-, 3,5-Diaminobenzoesäure, 4-, 5-Aminosalicylsäure, 3-amino-4 droxy- hydrogencarbonates, 4-amino-3-hydroxy-benzoesäure, 2-, 3-, 4-Aminobenzolsulfonsäure, 3-amino-4-hydroxybenzolsulfonsäure, 4-amino-3-hydroxynaphthalene-sulfonsà Nure, 6-amino-7-hydroxynaphthalene-2-sulfonsäure, 7-amino-4-hydroxynaphthalene-2- sulfonsäure, 4-amino-5-hydroxynaphthalene-2,7-disulfonsäure, 3-amino- 2-naphthenic thoesäure, 3-Aminophthalsäure, 5-Aminoisophthalsäure, 1,3,5, 1, 2,4-triamino benzene, 1, 2,4,5-tetraaminobenzene tetrahydrochloride, 2 , 4,5-Triaminophenol trihydrochloride, Pentaaminobenzol-penta hydrochloride, Hexaaminobenzol-hexahydro- chloride, 2,4,6-Triaminoresorcin trihydrochloride, 4,5-Diaminobrenzcatechinsulfat, 4,6-Diaminopyrogallol dihydrochloride, 3,5-diamino -4-hydroxybrenzcatechin- sulfate, aromatic anilines or phenols with a further aromatic radical, such as 4,4'-diaminostilbene dihydrochloride, 4,4'-diaminostilbene-2,2 '-disulfonsäure, Na salt, 4,4'-diaminodiphenylmethane, sulfide, sulfoxide, -amine, 4,4'-dia- minodiphenylamin-2-sulfonsäure, 4,4'-diaminobenzophenone, -diphenyl , 3,3 ', 4,4'-Tetraaminodiphenyl tetrahydrochloride, 3,3', 4,4'-tetraamino-benzophenone, 1, 3-bis (2,4-diaminophenoxy) -propane tetrahydrochloride, 1 , 8-bis- (2,5-diamino nophenoxy) -3,6-dioxaoctane tetrahydrochloride, 1, 3-bis- (4-aminophenylamino) - propane, -2-propanol, 1, 3-bis [N - (4-aminophenyl) -2-hydroxyethylamino] -2-propanol, N, N-bis [2- (4-aminophenoxy) -ethyl] methylamine trihydrochloride, nitrogen-containing heterocyclic compounds selected from the group consisting of
2-, 3-, 4-amino-, 2-amino-3-hydroxy-, 2,6-diamino-, 2,5-diamino-, 2,3-diamino-, 2-dimethylamino-5-amino-, 3-amino-2-methylamino-6-methoxy-, 2,3-diamino-6- methoxy-, 3,5-diamino-2,6-dimethoxy-, 2,4,5-triamino, 2,6- dihydroxy-3,4-di-methylpyridine, 4,5,6-triamino-2-hydroxy-4,5,6-triamino-4-hydroxy-2,5,6-triamino-2,4,5 , 6-tetraamino, 2-methylamino-4,5,6-triamino, 2,4-, 4,5-dia- mino-, 2-amino-4-methoxy-6-methyl-pyrimidine, 2.3 , 4-trimethylpyrrole, 2,4-dimethyl-3-ethyl-pyrrole, 3,5-diaminopyrazole, -1,2,4-triazole, 3-amino-, 3-amino-5-hydroxypyrazole, 2-, 3- , 8-aminoquinoline, 4-amino-quinaldine, 2-, 6-Aminonicotin- säure, 5-aminoisoquinoline, 5-, 6-aminoindazole, 5-, 7-amino-benzimidazole, - benzothiazole, 2,5-dihydroxy -4-morpholino aniline and indole and Indolinderiva- th such as 4-, 5-, 6-, 7-aminoindole, 4-, 5-, 6-, 7-hydroxyindole, 5,6-dihydroxyindole, 5,6-Dihydroxyindolin and 4-hydroxyindoline, and in each case from the formed with pre preferably inorganic physiologically Säuren äglichen salts of these compounds, aromatic hydroxy compounds selected from the group consisting of 2-, 4-, 5- methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, Brenzkate- chin, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2- , 3-, 4- methoxy, 3-dimethylamino-, 2- (2-hydroxyethyl) -, 3,4-methylenedioxyphenol, 2,4-, 3,4-Dihydroxybenzoesäure, -phenylessigsäure, Gallussäure , 2,4,6-Trihy- droxybenzoesäure, -acetophenone, 2-, 4-chlororesorcinol, 1-naphthol, 1, 5-, 2,3-, 2,7-dihydroxynaphthalene, 6-dimethylamino-4-hydroxy -2-naphthalinsulfonsäure, 3,6-dihydroxy-2,7-naphthalinsulfonsäure, and
CH-active compounds selected from the group consisting of 1, 2,3,3-tetramethyl-3H-indolium iodide, 2,3,3-tetramethyl-3-indolium-p-toluenesulfonate 1, 1, 2,3,3- tetramethyl-3-indolium methane sulfonate, 2,3-dimethyl-benzothiazolium iodide, 2,3-dimethyl benzothiazolium-p-toluenesulfonate, rhodanine, rhodanine-3-essigsäure, 1-ethyl (methyl) -2 -chinaldiniumiodid, Barbitursäure, thiobarbitursäure, 1, 3-dimethyl methyl (ethyl) thiobarbitursäure, oxindole, coumaranone and 1-methyl-3-phenyl-2-pyramid-zolinon.
3. Composition according to claim 1 or 2, characterized in that daß the compounds of the components A and B in an amount of 0.03 to 65, particularly 1 to 40 mmol, each based on 100 g of the total Färbemittels, are included.
4. Means according to one of Anspr├╝che 1 to 3, characterized in that it da├ƒ alkali metal, ammonium and / or substituted by hydroxyalkyl ammonium salts of C-Cg Carbons├ñuren, C ^ Ce-Hydroxycarbons├ñuren ​​and / or Kohlens├ñure enth├ñlt.
5. A composition according to any of Ansprüche 1 to 4, characterized in that are daß oxidizing agent in an amount of 0.01 to 6 wt .-%, based on the Anwendungslösung used.
6. A composition according to any of Ansprüche 1 to 5, characterized in that daß as the oxidant H 2 O is used. 2
7. The composition according to Ansprüche 1 to 6, characterized in that daß anionic, zwitterionic and / or nonionic surfactants are used.
8. Use of Dehydroascorbinsäure of formula (I)
Figure imgf000024_0001
in w├ñ├ƒriger or organic-w├ñ├ƒriger L├╢sung in the presence of at least one compound with prim├ñrer sekund├ñrer or amino group or hydroxy group, ausgew├ñhlt from prim├ñren sekund├ñren or aliphatic or aromatic amines nitrogen-containing heterocyclic compounds, ╬▒- to ╧ë- Aminos├ñuren, composed of two to nine Aminos├ñuren ​​oligopeptides and aromatic hydroxy compounds, and / or at least one CH-active compound for F├ñrben keratin-containing fibers.
9. A method for Färben keratin-containing fibers, wherein a Färbemittel containing
(A) Dehydroascorbinsäure of formula (I)
Figure imgf000024_0002
(B) at least one compound with prim├ñrer sekund├ñrer or amino group or hydroxy group, ausgew├ñhlt from prim├ñren sekund├ñren or aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, ╬▒- to ╧ë-Aminos├ñuren ​​from 2 to 9 Aminos├ñuren ​​constructed oligopeptides and aromatic hydroxy compounds, and / or at least one CH-active compound applied and ├╝bliche cosmetic ingredients to the keratin fibers, left for some time, ├╝blicherweise about 30 minutes on the fiber and is anschlie├ƒend ausgesp├╝lt again or washed out with a shampoo.
PCT/EP1998/006310 1997-10-14 1998-10-05 Agent for dyeing fibers containing keratin with a concentration of dehydroascorbic acid content WO1999018917A3 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE1997145354 DE19745354A1 (en) 1997-10-14 1997-10-14 Color containing dehydroascorbic acid and coupler for dyeing keratinous fibers, especially human hair
DE19745354.6 1997-10-14

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP19980954334 EP1028695A1 (en) 1997-10-14 1998-10-05 Agent for dyeing fibers containing keratin with a concentration of dehydroascorbic acid content
JP2000515555A JP2001519372A (en) 1997-10-14 1998-10-05 Dehydroascorbic acid-containing composition for dyeing keratin-containing fibers

Publications (2)

Publication Number Publication Date
WO1999018917A2 true true WO1999018917A2 (en) 1999-04-22
WO1999018917A3 true WO1999018917A3 (en) 1999-06-24

Family

ID=7845509

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/006310 WO1999018917A3 (en) 1997-10-14 1998-10-05 Agent for dyeing fibers containing keratin with a concentration of dehydroascorbic acid content

Country Status (4)

Country Link
EP (1) EP1028695A1 (en)
JP (1) JP2001519372A (en)
DE (1) DE19745354A1 (en)
WO (1) WO1999018917A3 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009010688A2 (en) * 2007-07-09 2009-01-22 L'oreal Skin-colouring composition containing a self-tanning agent and a colorant obtained by reacting an amine with dehydroascorbic acid or one of the monomer, polymer or isomer derivatives thereof
WO2011084810A2 (en) * 2009-12-21 2011-07-14 E. I. Du Pont De Nemours And Company 2,4,5-triaminophenols and related compounds
WO2011084762A2 (en) * 2009-12-21 2011-07-14 E. I. Du Pont De Nemours And Company 2,4,5-triaminophenols and related compounds
FR2967683A1 (en) * 2010-11-24 2012-05-25 Oreal New direct dyes unit derived from ascorbic acid, the dye composition comprising and method for dyeing human keratin materials from these dyes

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19852611C1 (en) * 1998-11-14 2000-09-07 Wella Ag Use of dehydroascorbic acid in fixing agents as well as compositions and methods for permanent hair shaping
DE10045856A1 (en) 2000-09-14 2002-03-28 Henkel Kgaa Colorant for keratin fibers, useful for coloring fur, wool, feathers and especially human hair, contains benzo(b)furan-3-one or benzo(b)thiophen-3-one derivative(s) and reactive carbonyl or methine-active compound(s)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1338063A (en) * 1962-10-25 1963-09-20 Interpal S A Hair dye
US5203875A (en) * 1991-03-28 1993-04-20 L'oreal Dyeing composition for keratinous fibers, containing oxidation dye precursors and hydroxybenzofurane used as couplers, and dyeing process using these compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1338063A (en) * 1962-10-25 1963-09-20 Interpal S A Hair dye
US5203875A (en) * 1991-03-28 1993-04-20 L'oreal Dyeing composition for keratinous fibers, containing oxidation dye precursors and hydroxybenzofurane used as couplers, and dyeing process using these compositions

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100221203A1 (en) * 2007-07-09 2010-09-02 L'oreal Dehydroascorbic acid or monomeric, polymeric or isomeric derivative thereof and an amine for artificially coloring the skin
WO2009010684A2 (en) * 2007-07-09 2009-01-22 L'oreal Process for dyeing human keratin materials using an ortho-diphenol and dehydroascorbic acid or a monomeric, polymeric or isomeric derivative thereof
WO2009010686A2 (en) * 2007-07-09 2009-01-22 L'oreal Process for making up the skin, the lips or the nails using a dye obtained by reacting an amine with dehydroascorbic acid or a monomeric, polymeric or isomeric derivative
WO2009010684A3 (en) * 2007-07-09 2009-04-16 Patrick Choisy Process for dyeing human keratin materials using an ortho-diphenol and dehydroascorbic acid or a monomeric, polymeric or isomeric derivative thereof
WO2009010686A3 (en) * 2007-07-09 2009-04-16 Charlotte Feltin Process for making up the skin, the lips or the nails using a dye obtained by reacting an amine with dehydroascorbic acid or a monomeric, polymeric or isomeric derivative
WO2009010685A3 (en) * 2007-07-09 2009-04-23 Patrick Choisy Skin-colouring method using dehydroascorbic acid or one of the monomer, polymer or isomer derivatives thereof and an amine
WO2009010688A3 (en) * 2007-07-09 2009-04-23 Guillaume Cassin Skin-colouring composition containing a self-tanning agent and a colorant obtained by reacting an amine with dehydroascorbic acid or one of the monomer, polymer or isomer derivatives thereof
WO2009010688A2 (en) * 2007-07-09 2009-01-22 L'oreal Skin-colouring composition containing a self-tanning agent and a colorant obtained by reacting an amine with dehydroascorbic acid or one of the monomer, polymer or isomer derivatives thereof
WO2011084810A2 (en) * 2009-12-21 2011-07-14 E. I. Du Pont De Nemours And Company 2,4,5-triaminophenols and related compounds
WO2011084762A2 (en) * 2009-12-21 2011-07-14 E. I. Du Pont De Nemours And Company 2,4,5-triaminophenols and related compounds
WO2011084762A3 (en) * 2009-12-21 2011-10-06 E. I. Du Pont De Nemours And Company 2,4,5-triaminophenols and related compounds
WO2011084810A3 (en) * 2009-12-21 2011-10-13 E. I. Du Pont De Nemours And Company 2,4,5-triaminophenols and related compounds
FR2967683A1 (en) * 2010-11-24 2012-05-25 Oreal New direct dyes unit derived from ascorbic acid, the dye composition comprising and method for dyeing human keratin materials from these dyes
WO2012069476A1 (en) * 2010-11-24 2012-05-31 L'oreal Novel direct dyes containing an ascorbic acid-based unit, dye composition comprising them and process for dyeing human keratin materials using these dyes

Also Published As

Publication number Publication date Type
WO1999018917A3 (en) 1999-06-24 application
DE19745354A1 (en) 1999-04-15 application
JP2001519372A (en) 2001-10-23 application
EP1028695A1 (en) 2000-08-23 application

Similar Documents

Publication Publication Date Title
US6165230A (en) 1,4-diazacycloheptane derivatives and their use in hair oxidation dyes
US6537330B1 (en) Colorants
EP1568354A1 (en) Oxidative dyeing composition
WO1997004739A1 (en) Oxidation colorants for dyeing keratinic fibers, containing a special combination of alkalisation agents
US20030106167A1 (en) New colouring combination
DE10148845A1 (en) Dyeing keratin fibers, especially human hair, using diazonium salt or carbonyl compound and oxidizing agent, gives strong shades of good wash fastness
WO2000029036A2 (en) Colorants with transition metal complexes
US6371993B1 (en) Utilization of onium aldehydes and onium ketones for dying fibers containing keratin
US6648925B1 (en) Coloring agent comprising transition metals
DE10118271A1 (en) Hair-dyeing compositions contain new and known diazo-thiazole derivatives as direct dyes, optionally in combination with oxidation dyes
EP0873745A2 (en) Dyestuff for keratinous fibers
DE4335623A1 (en) Indolinone derivatives for dyeing keratin-containing fibres
WO2001034106A1 (en) Agent for colouring keratin containing fibres
DE4434494A1 (en) 2-hydroxy-1-ethanone derivatives for dyeing keratin-containing fibers
WO2000038636A1 (en) Agent for dying keratin fibers
DE19949033A1 (en) hair coloring
DE19914927A1 (en) Agent for care of keratinic fibers, especially human hair, used e.g. for dyeing hair, comprises surfactant and conditioner
DE19914926A1 (en) Composition for coloring keratinic fibres, especially human hair, contains a dye precursor and/or a dye and a cationic surface active agent of the fatty acid aminopropyl PG-dimonium chloride phosphate type
EP0873744A2 (en) Use of heterocyclic carbonyl compounds for dying keratinous fibers
DE19717224A1 (en) Use of unsaturated aldehydes for dyeing keratin fibers
WO2001003651A2 (en) Agent for dyeing fibres containing keratin
GB2337530A (en) Direct hair-colouring compositions based on phenalenone derivatives
DE4335628A1 (en) Composition for dyeing keratin-containing fibres
US6770102B1 (en) Agent for dying keratin fibers
DE19926377A1 (en) Formulations for coloring keratin-containing fibers

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

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: A2

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

121 Ep: the epo has been informed by wipo that ep was designated in this application
AL Designated countries for regional patents

Kind code of ref document: A3

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

AK Designated states

Kind code of ref document: A3

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

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 1998954334

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 11500/99

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 09529561

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 1998954334

Country of ref document: EP

NENP Non-entry into the national phase in:

Ref country code: CA

WWW Wipo information: withdrawn in national office

Ref document number: 1998954334

Country of ref document: EP