WO2003030849A1 - Procede de coloration et de decoloration ulterieure de cheveux - Google Patents

Procede de coloration et de decoloration ulterieure de cheveux Download PDF

Info

Publication number
WO2003030849A1
WO2003030849A1 PCT/EP2002/010733 EP0210733W WO03030849A1 WO 2003030849 A1 WO2003030849 A1 WO 2003030849A1 EP 0210733 W EP0210733 W EP 0210733W WO 03030849 A1 WO03030849 A1 WO 03030849A1
Authority
WO
WIPO (PCT)
Prior art keywords
amino
acid
methyl
quinolinium
diamino
Prior art date
Application number
PCT/EP2002/010733
Other languages
German (de)
English (en)
Other versions
WO2003030849A8 (fr
Inventor
Doris Oberkobusch
Udo Erkens
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
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to EP02777203A priority Critical patent/EP1434560A1/fr
Publication of WO2003030849A1 publication Critical patent/WO2003030849A1/fr
Publication of WO2003030849A8 publication Critical patent/WO2003030849A8/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
    • 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 invention relates to a method and a kit for dyeing and later decolorizing keratin fibers, in particular human hair, and the use of decolorizing agents for removing oxy-dyeings from the keratin fiber.
  • the dyeing of keratin fibers can be carried out in the conventional sense either with direct dyes or with oxidation dyes.
  • the color pigments result from the oxidative coupling of one or more developer components with one another or with one or more coupler components. Coupler and developer components are also referred to as oxidation dye precursors.
  • the oxidation is mostly caused by an oxidizing agent such as H 2 O 2 , the frequent use of which can damage the structure of the hair fiber.
  • some oxidation dye precursors or certain mixtures of oxidation dye precursors can sometimes have a sensitizing effect on people with sensitive skin.
  • hair coloring with certain carbonyl components in combination with compounds with primary or secondary amino group or hydroxy group, aromatic hydroxy compounds and / or at least one CH-acidic compound is considered a new coloring principle.
  • Corresponding agents for coloring hair are disclosed, for example, in publication WO 00/38633.
  • a dyeing according to this new dyeing principle is referred to below as oxo dyeing.
  • colorations can be divided into three categories, permanent, semi-permanent and temporary. Oxidation hair colors cause e.g. permanent coloring of the hair. The color result is very durable and practically cannot be removed by washing your hair.
  • Direct dyes give the hair a semi-permanent to temporary
  • Semi-permanent dyeings can be removed from the hair fiber with approx. 2-10 hair washes, temporary dyeings can be removed by washing the hair.
  • the oxo dyeings are almost permanent and can be removed with 25-35 washes.
  • the consumer demands genuine, fashionable dyeings that do not damage the fiber structure and can be completely removed from the fiber in one procedure at the request of the user.
  • the publication DE 197 37 987 C1 discloses sulfur-containing agents for the reductive decolorization of hair which have been dyed with substantive dyes.
  • WO 98/22078 and EP 943316 A2 describe processes and agents used therein for reductive decolorization of hair colorations.
  • the decolourable hair dyeings are also permanent dyeings with oxidation dyes.
  • WO 01/28507 describes a multi-component kit for dyeing and decoloring dyeings. The colorations are achieved with a hair dye containing aldehydes or ketones in combination with CH-acidic compounds.
  • the object of the present invention is to provide a method by means of which dyeings are obtained which are qualitatively at least equivalent in terms of color depth, gray coverage and fastness properties in comparison with conventional oxidation hair dyeing agents, but without necessarily relying on oxidizing agents such as H 2 O 2 to be.
  • the hair fiber is less damaged.
  • a further object of the present invention is to remove the dyeing according to the invention obtained from the keratin fiber more effectively without degenerating the natural hair pigments and without achieving a shift in shades.
  • the present invention therefore relates to a process for dyeing and later decolorizing keratin fibers, in particular human hair, characterized in that in a dyeing procedure P1
  • a colorant containing at least one carbonyl compound (component A) and at least one compound (component B) with a primary or secondary amino group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids and from 2 to 9 Amino acids built oligopeptides, applied to the keratin fiber,
  • a decolorizing agent comprising at least one compound selected from a sulfur-containing compound, an ⁇ -oxocarboxylic acid, an aldehyde or a reductone applied to the fiber,
  • P3a another decolorizing agent containing at least one compound selected from a sulfur-containing compound, an ⁇ -oxocarboxylic acid, an aldehyde or a reductone applied to the fiber, ⁇ P3b) left on the fiber for 5-60 minutes and
  • the colorant contains at least one carbonyl compound of the formula I
  • R 1 represents a group -CHO or
  • R 3 represents a group -CO-R 6 , in which R 6 represents hydrogen, a CC 4 - alkyl group, an aryl group or a heteroaryl group, with the proviso that according to (a) R 2 , R 3 and R 4 or according to (b) R, R 2 and R 4 independently of one another represent a hydrogen atom, a halogen atom, a CC 4 alkyl group, a CC 4 alkoxy group, a hydroxy-C C alkoxy group, a hydroxy group, a nitro group , an amino group which can be substituted by CrC ⁇ alkyl groups, or a -C-C 4 acyl group, where two of the radicals together can form a fused benzene ring,
  • R 5 is an oxygen atom, a CrC ⁇ alkyl group, a C 2 -C 4 - alkenyl group, a C
  • R 5 is oxygen and is a halide, benzenesulfonate, tetrafluoroborate, p-toluenesulfonate, methanesulfonate, trifluoromethanesulfonate, perchlorate, 0.5 sulfate, hydrogen sulfate or tetrachlorozincate.
  • CrC alkyl groups in the compounds according to the invention are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl.
  • Preferred alkyl groups are methyl and ethyl, methyl is a particularly preferred alkyl group.
  • Preferred CC acyl groups are, for example, acetyl, propionyl and butyryl.
  • Methoxy, ethoxy, propoxy and butoxy are examples of preferred -CC alkoxy groups, a particularly preferred alkoxy group is the methoxy group.
  • Preferred hydroxy-CrC 4 - alkoxy groups are 2-hydroxyethyloxy and 3-hydroxypropyloxy.
  • Vinyl, allyl and 3-buten-1-yl are preferred C -C alkenyl groups.
  • Examples of preferred Aryl-CrC 4 - alkyl groups are benzyl, 2-phenylethyl and naphthylmethyl. Benzyl is particularly preferred.
  • Preferred heteroaryl groups are 5-, 6- and 7-membered aromatic heterocycles with 1 to 3 heteroatoms, which are selected from nitrogen, oxygen and sulfur.
  • Preferred aryl groups are, for example, phenyl, naphthyl and biphenyl, phenyl is a particularly preferred aryl group.
  • suitable halogen substituents are preferably fluorine, chlorine, bromine and iodine, and chlorine and bromine are particularly preferred. According to the invention, the other terms used are derived from the definitions given here.
  • the carbonyl compound of the formula I is selected from 2-formyl-1-methyl-quinolinium-, 4-formyl-1-methyl-quinolinium-, 5-formyl-1-methyl- quinolinium-, 6-formyl-1-methyl-quinolinium-, 7-formyl-1-methyl-quinolinium-, 8-formyl-1-methyl-quinolinium-, 5-formyl-1-ethyl-quinolinium-, 6-formyl -1-ethyl-quinolinium, 7-formyl-1-ethyl-quinolinium, 8-formyl-1-ethyl-quinolinium, 5-formyl-1-benzyl-quinolinium, 6-formyl-1-benzyl-quinolinium -, 7-formyl-1-benzyl-quinolinium-, 8-formyl-1-benzyl-quinolinium-, 5-formyl-1-allyl-quinolinium-, 6-formyl-1-methyl-quinolinium-, 4-formyl-1-methyl-
  • carbonyl compounds which are selected from the group that is formed from 1-methyl-5-oxo-indeno [1,2-b] pyridinium trifluoromethanesulfonate and from the carbonyl compounds used in the publications mentioned below are also preferred according to the invention which is expressly referred to here:
  • Aromatic nitro aldehydes according to WO-A1-00 / 38634, in particular 2,4-dinitrobenzaldehyde.
  • the carbonyl compounds are usually used in an amount of 0.03 to 65 mmol, in particular 1 to 40 mmol, in each case based on 100 g of the total colorant.
  • the carbonyl compounds used according to the invention are used together with at least one further component (component B), selected from compounds having primary or secondary amino groups, which in turn are selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides composed of 2 to 9 amino acids ,
  • component B selected from compounds having primary or secondary amino groups, which in turn are selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides composed of 2 to 9 amino acids .
  • component B selected from compounds having primary or secondary amino groups, which in turn are selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides composed of 2 to 9 amino acids .
  • component B Several different compounds of component B can also be used together.
  • the embodiment described above also includes the use of such substances as substantive colorants which are reaction products from the chemical reaction of the carbonyl compounds according to the invention with the compounds of component B.
  • Such reaction products can e.g. B. can be obtained by briefly heating the two reactants in stoichiometric amounts in an aqueous neutral to weakly alkaline medium, they either precipitate out of solution as a solid or by evaporation of the solution therefrom be isolated.
  • the reaction products can also be used in combination with other dyes or dye precursors.
  • Suitable compounds with primary or secondary amino group as component B are e.g. B. primary aromatic amines such as N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N- (2-hydroxyethyl) -N-ethyl-p-pheny!
  • R 7 represents a hydroxyl or an amino group which can be substituted by C 1-4 alkyl, C 1- hydroxyalkyl, C 1-4 alkoxy or C 1-4 alkoxy-d ⁇ alkyl groups,
  • R 8 , R 9 , R 10 , R 11 and R 12 independently of one another for a hydrogen atom, a hydroxyl or an amino group, which can be substituted by CC-alkyl-, CrC 4 -hydroxyalkyl, CC - alkoxy-, CC 4 -aminoalkyl- or CrGralkoxy-dO t -alkyl groups can be substituted, and.
  • Z 1 for a direct bond, a saturated or unsaturated carbon chain with 1 to 4 carbon atoms, optionally substituted by hydroxyl groups, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom, or a group with the formula III
  • Q is a direct bond, a CH 2 or CHOH group
  • Q 1 and Q "independently of one another for an oxygen atom, an NR 13 group, wherein R 13 is a hydrogen atom, a C 1-4 -alkyl or a hydroxy-C 1-4 -alkyl group, both groups also together with the rest of the molecule can form a 5-, 6- or 7-ring means the group O- (CH 2 ) p -NH or NH- (CH 2 ) p ⁇ O, where p and p 'are 2 or 3 , stand and
  • O is a number from 1 to 4,
  • 4,4'-diaminostilbene and its hydrochloride 4,4'-diaminostilbene-2,2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene and its hydrochloride, 4, 4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfide, 4,4'- Diaminodiphenyl sulfoxide, 4,4'-diaminodiphenylamine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4-diaminobenzophenone, 4,4'-diaminodiphenyl ether, 3,3 ', 4,4'-tetraaminodiphenyl, 3 , 3 ', 4,4'-tetraamino-benzophenone, 1,3-bis (2,4-diaminophenoxy) propane, 1,8-bis (2,4
  • the abovementioned compounds can be used both in free form and in the form of their physiologically tolerable salts, in particular as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable nitrogen-containing heterocyclic compounds are e.g. B. 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-amino-3-hydroxy-pyridine, 2,6-diamino-pyridine, 2,5-diamino-pyridine, 2- (aminoethylamino) -5-aminopyridine, 2,3-diamino-pyridine, 2-dimethylamino-5-amino-pyridine, 2-methylamino-3-amino-6-methoxy-pyridine, 2,3-diamino-6-methoxy-pyridine, 2,6- Dimethoxy-3,5-diamino-pyridine, 2,4,5-triamino-pyridine, 2,6-dihydroxy-3,4-dimethylpyridine, N- [2- (2,4-diaminophenyl) aminoethyl] -N - (5-amino-2-pyridyl) amine, N- [2- (4
  • the hydroxypyrimidines disclosed in DE-U1-299 08 573 can also be used as heterocyclic compounds.
  • the aforementioned compounds can be used both in free form and in the form of their physiologically salts in question, e.g. B. as salts of inorganic acids such as hydrochloric or sulfuric acid.
  • Preferred amino acids are all naturally occurring and synthetic ⁇ -amino acids, e.g. obtained by hydrolysis from vegetable or animal proteins, e.g. Collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein accessible amino acids. Both acidic and alkaline amino acids can be used. Preferred amino acids are arginine, histidine, tyrosine, phenylalanine, DOPA (dihydroxyphenylalanine), ornithine, proline, lysine and tryptophan. But also other amino acids, e.g. 6-aminocaproic acid and ⁇ -alanine can be used.
  • the oligopeptides can be naturally occurring or synthetic oligopeptides, but also the oligopeptides contained in polypeptide or protein hydrolyzates, provided that they have sufficient water solubility for use in the colorants according to the invention.
  • examples are e.g. Glutathione or the oligopeptides contained in the hydrolyzates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein. Use together with compounds having a primary or secondary amino group is preferred.
  • the compounds of component B are particularly preferably selected from the group consisting of N- (2-hydroxyethyl) -N-ethyl-p-phenylenediamine, 2-chloro-p-phenylenediamine, N, N-bis- (2-hydroxyethyl) ) -p-phenylenediamine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-amino-6-chloro-4-nitrophenol, p-phenylenediamine, 2- (2,5-diaminophenyl) ethanol, 2,5- Diaminotoluene, 3,4-methylenedioxyaniline, 2-amino-4- (2-hydroxyethylamino) anisole, 2- (2,4-diaminophenoxy) ethanol, 3-amino-2,4-dichlorophenol, 4-amino-2, 6-dichlorophenol, 2-methyl-5-aminophenol, 3-methyl-4-aminophenol, 2-methyl-5- (2-hydroxye
  • the compound having a primary or secondary amino group is not selected from 2-methylquinolinium and 4-methylquinolinium derivatives.
  • the above-mentioned compounds of component B can be used in an amount of 0.03 to 65 mmol, in particular 1 to 40 mmol, in each case based on 100 g of the entire colorant. Furthermore, it can be particularly preferred according to the invention to use the carbonyl compound and component B in a molar ratio of 2: 1 to 1: 2, in particular approximately equimolar.
  • the carbonyl compounds on the one hand and the compounds of component B on the other hand are preferably used in proportions such that the sum of the number of carbonyl groups of the carbonyl compounds and the sum of the number of amino groups of the compounds of component B are in a ratio of 2: 1 to 1: 2.
  • the agents used in the process according to the invention can additionally contain color enhancers.
  • the color enhancers are preferably selected from the group consisting of piperidine, piperidine-2-carboxylic acid, piperidine-3-carboxylic acid, piperidine-4-carboxylic acid, pyridine, 2-hydroxypyridine, 3-hydroxypyridine, 4-hydroxypyridine, imidazole, 1-methylimi- dazol, histidine, pyrrolidine, proline, pyrrolidone, pyrrolidone-5-carboxylic acid, pyrazole, 1,2,4-triazole, piperazidine, their derivatives and their physiologically tolerable salts.
  • the aforementioned color enhancers can be used in an amount of 0.03 to 65 mmol, in particular 1 to 40 mmol, in each case based on 100 g of the entire colorant.
  • Suitable metal salts are e.g. Formates, carbonates, halides, sulfates, butyrates, valerates, capronates, 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, calcium, strontium or barium, or of aluminum, manganese, iron, cobalt, copper or zinc, with sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate being preferred.
  • These salts are preferably present in an amount of 0.03 to 65 mmol, in particular 1 to 40 mmol, based on 100 g of the total colorant.
  • Oxidizing agents for example H 2 O 2
  • H 2 O 2 oxidizing agents
  • Oxidizing agents are generally used in an amount of 0.01 to 6% by weight, based on the application solution.
  • a preferred oxidizing agent for human hair is H 2 O 2 .
  • customary oxidation hair colors or substantive dyes are added to the colorants according to the invention in order to further modify the color shades.
  • the substantive dyes can e.g. B. can be selected from the group of nitrophenylenediamines, nitroaminophenols, anthraquinones or indophenols, such as those under the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 6, Basic Yellow 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, Basic Brown 17, Picramic Acid and 2- Amino-6-chIoro-4-nitrophenol known compounds and 4- Amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-nitro-1, 2,3,4-tetrahydroquinoxaline, 4-N-ethyl-1,
  • the individual components of the colorants which can be used in the process according to the invention can either be stored separately or together, either in a liquid to pasty preparation (aqueous or anhydrous) or as a dry powder. If the components are stored together in a liquid preparation, this should be largely anhydrous to reduce a reaction of the components.
  • the reactive components are only intimately mixed with one another immediately before use. In dry storage, a defined amount of warm (50 to 80 ° C) water is usually added before use and a homogeneous mixture is produced.
  • the colorants used in the process according to the invention can contain all the active ingredients, additives and auxiliaries known in such preparations.
  • the colorants or decolorants 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.
  • 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. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • Suifo-succinic 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 alkane sulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon atoms, alpha-sulfofatty acid methyl ester of fatty acids with 12 to 18 carbon atoms, alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH 2 -CH 2 O) x -SO 3 H, in which R is a preferably linear alkyl group with 10 to 18 C atoms and x 0 or 1 to 12,
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols with 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one -COO (" ⁇ - or -SOs ⁇ group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as N-alkyl-N, N dimethylammonium glycinate, for example cocoalkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example cocoacylaminopropyl dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, and the cocoacylaminoethyl-hydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name Coca
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 8-18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 C. Atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12-18 acyl sarcosine.
  • 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
  • Examples of the cationic surfactants which can be used in the colorants and decolorants according to the invention are, in particular, quaternary ammonium compounds.
  • Ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, for.
  • 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 stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are notable for their good biodegradability.
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to CTFA nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride”.
  • 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 division are understood to mean mixtures of homologs which are obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts.
  • narrow homolog distributions are obtained if, for example, hydrotaicites, 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.
  • auxiliaries and additives are, for example, nonionic polymers such as, for example, vinylpyrrolidone / acrylate copolymers,
  • Imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as, for example, acrylamidopropyl trimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyacrylic polymers, anionic polymers such as anionic polymers such as acids, vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate
  • Thickening agents 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 as e.g. B. bentonite or fully synthetic hydrocolloids such as e.g.
  • Structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin,
  • 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,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as whale, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether,
  • 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
  • constituents of the water-containing carrier are used for the production of the coloring and decolorizing agents used in the process according to the invention in amounts customary for this purpose; e.g. emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant.
  • the pH of the ready-to-use coloring and decolorization preparations according to the invention is usually between 2 and 11, preferably in a range from pH 5 to 10.
  • a decolorization procedure (P2) is carried out immediately after the dyeing procedure (P1) or after a longer period of time.
  • the longer period which can be between P1 and P2 of the method according to the invention, corresponds to 1 to 50 days.
  • the sulfur-containing compound contained in the decolorizing agents used is preferably selected from alkali metal or alkaline earth metal dithionite, alkali metal or alkaline earth metal sulfite, ammonium thioglycolate, calcium thioglycolate, cysteine, N-acetylcysteine, glutathione, cysteamine or its salts, homocysteine, penicetaldehyde and mercap.
  • a particularly preferred sulfur-containing compound is selected from an alkali metal and alkaline earth metal dithionite and L-cysteine.
  • ⁇ -Oxocarboxylic acids preferably contained in the decolorizing agents are selected from ⁇ -ketoglutaric acid, pyruvic acid and glyoxylic acid.
  • Glycolaldehyde and glyoxal are preferred aldehydes contained in the decolorizing agents.
  • the decolorizing agents preferably contain reductones selected from ascorbic acid, isoascorbic acid or their salts and esters, 2,3-dihydroxy-2-cyclopenten-1-one and hydroxypropanedial.
  • the decolorizing agent used in step P3a preferably contains at least one ⁇ -oxocarboxylic acid, in particular ⁇ -ketoglutaric acid, pyruvic acid and glyoxylic acid.
  • At least one compound selected from sulfur-containing compounds, ⁇ -oxocarboxylic acids, aldehydes and reductones is incorporated into a suitable carrier.
  • suitable carriers are e.g. B. thickened aqueous solutions, creams (emulsions), gels or surfactant-containing, foaming preparations, for. B. shampoos other preparations that are suitable for use on the hair.
  • a second subject of the invention is the use of an agent for decolorizing keratin fibers, in particular human hair, containing at least one Compound selected from sulfur-containing compounds, ⁇ -oxocarboxylic acids, aldehydes and reductones, with the proviso that the keratin fiber is visible through a colorant containing at least one carbonyl compound and as component B at least one compound with primary or secondary amino group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids and oligopeptides composed of 2 to 9 amino acids.
  • a third object of the invention is a kit for coloring and decolorizing keratin fibers, in particular human hair, which as separately assembled components in
  • Container (1) the colorant used in the method according to the invention and container (2) the decolorizing agent used in procedure P2 according to the invention
  • the carbonyl component and component B of the colorant can be packaged in two different containers 1 a and 1 b.
  • the kit according to the invention optionally contains, in addition to container 1, or containers 1a and 1b, two separately prepared decolorizing agents with the coloring agent.
  • This kit is used when the further decolorization procedure P3 is to be carried out in the process carried out.
  • the kit of this embodiment consists of three components, the coloring agent used in the method according to the invention in container (1) (or in containers 1a and 1b), the decolorizing agent used in procedure P2 in container (2) and in container (3 ) contains the additional decolorizing agent used in procedure P3. Examples
  • Component B (see table 1)
  • cetearylstearyl alcohol with about 20 EO units (INCI name: Ceteareth-20) (COGNIS)
  • the substances Hydrenol ® D, Lorol ® and Eumulgin ® B2 were used in. Melted 80 ° C, mixed with 80 ° C hot water containing Texapon ® NSO and Dehyton ® K, and emulsified with vigorous stirring. The emulsion was then cooled with gentle stirring. Sodium sulfite, ascorbic acid and the compound of component B (according to Table 1) were added with stirring. The emulsion was adjusted to pH 10 with aqueous ammonia solution (25%) and made up to 100 g with water. Compounds used in Table 1 as components B to prepare the color cream:
  • color gels were prepared which contain the carbonyl component.
  • the composition of the color gels is shown in Table 2.
  • the following carbonyl compounds (according to the invention) were used:
  • Methacrylic acid stearyl alcohol + 20-EO-ester
  • -acrylic acid copolymer INCCI name: Acrylates / Steareth-20 methacrylate copolymer
  • ROHM & HAAS ISP
  • Stearic acid isooctyl ester (INCI name: ethylhexyl stearate) (COGNIS) oleyl cetyl alcohol + 5-EO, vegetable-based (INCI name: Oleth-5) (COGNIS)
  • the carbonyl compound according to Table 2 was dissolved together with sodium sulfite and ascorbic acid in the 50 ° C hot water with the addition of ammonia (25% aqueous solution). Then Natrosol ® 250 HR was added, the pH was adjusted to 10 with ammonia and made up to 100 g with water.
  • N-allyl isatin was dissolved in the propylene carbonate and with Eumulgin ® O 5 V, Cetiol ® 868, Dehydol ® LS 4N and Aculyn ® 22 with stirring. ii) Coloring and colorimetric measurements
  • a color gel and a coloring cream were mixed in a weight ratio of 1: 1 and applied to natural strands of hair from Kerling.
  • the amount by weight of the color mixture applied was three times the weight of the hair to be dyed.
  • the used color cream / color combination are shown in Table 4. After an exposure time of the color mixture of 30 minutes at 32 ° C., the strands were washed out with water and dried.
  • the dyeing for the comparative tests was carried out as described in the examples in WO 01/28507 A1 using the color formulations of Examples 11, 12 and 13, but for better comparability with natural white hair from Kerling.
  • COGNIS Polyethylene glycol
  • the dyed lock of hair was moistened with a decolorizing agent immediately after the above-mentioned dyeing process (see Table 4).
  • the amount by weight of the decolorizing agent applied is three times the weight of the hair to be decolored.
  • the decolorizing agent was rinsed off the hair after an exposure time of 15 minutes.
  • the hair was then dried and measured colorimetrically using the Texflash DC 3881 from Datacolor to determine the CIE Lab values.
  • the amount by weight of the decolorizing agent applied is three times the weight of the hair to be decolored.
  • the exposure time is 60 minutes in the case of Examples 11 and 12 and 15 minutes in the case of Example 13.
  • the decolorizing agent was rinsed off the hair after the exposure time.
  • the hair was then dried and measured colorimetrically using the Texflash DC 3881 from Datacolor to determine the CIE Lab values.
  • the entries marked E5 in Table 4 under the heading "decolorizing agents” represent decolorization of the colored hair strand using a two-stage decolorization process.
  • the decolorizing agent E1 (see Table 3) was applied to the dyed lock of hair immediately after the above-mentioned dyeing process and rinsed out after an exposure time of 15 minutes.
  • the decolorizing agent E3 (see Table 3) was then applied to the hair and rinsed off from the hair after an exposure time of 10 minutes.
  • the hair was then dried and measured colorimetrically using the Texflash DC 3881 from Datacolor to determine the CIE Lab values.
  • the amount by weight of the respective decolorizing agent applied was three times the weight of the hair to be decolorized.
  • the color differences between the colored hair strand and the discolored hair strand result from the respective CIE Lab values according to the color spacing formula given below (see also DIN 6174, German standards, Benth Verlag GmbH, Berlin, 1975).
  • the undyed hair is used as a reference.
  • ⁇ E [( ⁇ L) 2 + ( ⁇ a) 2 + ( ⁇ b) 2 ] 1 ' 2 (color difference formula)
  • Table 4 summarizes the measured CIE Lab values and the calculated color difference of the dye-decolorization tests according to the invention using the method according to the invention.
  • Table 5 shows the measured CIE-Lab values of the decolorization process known from the prior art. The smaller the ⁇ E value, the better the initial hair color is achieved again after decolorization.

Abstract

Kit et procédé correspondant de coloration et de décoloration ultérieure de fibres kératiniques, en particulier de cheveux humains. Selon ledit procédé, (P1a) un colorant contenant au moins un composé carbonyle (constituant A) et au moins un composé à groupe amino primaire ou secondaire (constituant B), choisi parmi des amines aliphatiques ou aromatiques primaires ou secondaires, des composés hétérocycliques azotés et des oligopeptides constitués de 2 à 9 acides aminés, est appliqué sur les fibres kératiniques, (P1b) laissé 5 à 45 minutes sur les fibres kératiniques pour déployer son action, puis (P1c) rincé ou éliminé à l'aide d'un shampooing. Ledit procédé comporte également une procédure de décoloration (P2), effectuée immédiatement après la coloration ou au bout d'un certain temps. Cette procédure consiste (P2a) à appliquer sur les fibres un décolorant contenant au moins un composé choisi parmi un composé soufré, un acide alpha -oxocarboxylique, un aldéhyde ou une réductone, (P2b) à laisser agir le décolorant pendant 5 à 60 minutes sur les fibres, puis (P2c) à rincer les fibres.
PCT/EP2002/010733 2001-10-04 2002-09-25 Procede de coloration et de decoloration ulterieure de cheveux WO2003030849A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP02777203A EP1434560A1 (fr) 2001-10-04 2002-09-25 Procede de coloration et de decoloration ulterieure de cheveux

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2001148848 DE10148848A1 (de) 2001-10-04 2001-10-04 Verfahren zum Färben und späterem Entfärben von Haaren
DE10148848.3 2001-10-04

Publications (2)

Publication Number Publication Date
WO2003030849A1 true WO2003030849A1 (fr) 2003-04-17
WO2003030849A8 WO2003030849A8 (fr) 2004-12-29

Family

ID=7701296

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/010733 WO2003030849A1 (fr) 2001-10-04 2002-09-25 Procede de coloration et de decoloration ulterieure de cheveux

Country Status (3)

Country Link
EP (1) EP1434560A1 (fr)
DE (1) DE10148848A1 (fr)
WO (1) WO2003030849A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004025272A1 (de) * 2004-05-19 2005-12-08 Henkel Kgaa Verwendung von speziellen formylierten Chinoliniumderivaten in Kombination mit aminosubstituierten Diarylderivaten und mindestens einem weiteren primären oder sekundären, aromatischen Amin
DE102004025273A1 (de) * 2004-05-19 2005-12-08 Henkel Kgaa Verwendung von speziellen formylierten Chinoliniumderivaten in Komination mit 2-Amino-6-chlor-4-nitrophenol und mindestens einem weiteren primären oder sekundären, aromatischen Amin
DE102004025271A1 (de) * 2004-05-19 2005-12-08 Henkel Kgaa Verwendung von speziellen formylierten Chinoliniumderivaten in Kombination mit aminosubstituierten Pyrimidinderivaten und mindestens einem weiteren primären oder sekundären, aromatischen Amin

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1033375B (de) * 1956-03-07 1958-07-03 Wella Ag Verfahren zum Entfaerben von animalischen und pflanzlichen Fasern, die mit indigoiden Farbstoffen, gegebenenfalls im Gemisch mit 2-Oxy-1, 4-naphthochinon, gefaerbt sind
DE1151242B (de) * 1961-01-31 1963-07-11 Guenther Vogt Dipl Chem Dr Abziehmittel fuer gefaerbtes Keratinfaser-material, insbesondere fuer lebendes Haar
DE1194099B (de) * 1963-04-24 1965-06-03 Partipharm A G Verfahren zum Faerben menschlicher Haare
DE1492198A1 (de) * 1965-08-05 1969-12-04 Therachemie Chem Therapeut Haarfaerbemittel
US3800809A (en) * 1972-11-20 1974-04-02 Avon Prod Inc Bleaching composition for permanently dyed hair and method of use
US3892845A (en) * 1972-09-29 1975-07-01 Avon Prod Inc Hair shade adjuster
US5034014A (en) * 1990-06-18 1991-07-23 Clairol, Inc. Hair dye composition and method
EP0943316A2 (fr) * 1998-03-12 1999-09-22 Wella Aktiengesellschaft Agent pour colorer et decolorer des cheveux
WO2000033799A1 (fr) * 1998-12-07 2000-06-15 Wella Aktiengesellschaft Produit de coloration de fibres
WO2001028507A1 (fr) * 1999-10-20 2001-04-26 Wella Aktiengesellschaft Agent et procede pour la coloration de fibres
WO2002015855A1 (fr) * 2000-08-21 2002-02-28 L'oreal Composition de decoloration des fibres keratiniques teintes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10130144A1 (de) * 2001-06-22 2003-01-02 Wella Ag 1-Benzopyran-Derivate und deren Salze enthaltende Färbemittel

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1033375B (de) * 1956-03-07 1958-07-03 Wella Ag Verfahren zum Entfaerben von animalischen und pflanzlichen Fasern, die mit indigoiden Farbstoffen, gegebenenfalls im Gemisch mit 2-Oxy-1, 4-naphthochinon, gefaerbt sind
DE1151242B (de) * 1961-01-31 1963-07-11 Guenther Vogt Dipl Chem Dr Abziehmittel fuer gefaerbtes Keratinfaser-material, insbesondere fuer lebendes Haar
DE1194099B (de) * 1963-04-24 1965-06-03 Partipharm A G Verfahren zum Faerben menschlicher Haare
DE1492198A1 (de) * 1965-08-05 1969-12-04 Therachemie Chem Therapeut Haarfaerbemittel
US3892845A (en) * 1972-09-29 1975-07-01 Avon Prod Inc Hair shade adjuster
US3800809A (en) * 1972-11-20 1974-04-02 Avon Prod Inc Bleaching composition for permanently dyed hair and method of use
US5034014A (en) * 1990-06-18 1991-07-23 Clairol, Inc. Hair dye composition and method
EP0943316A2 (fr) * 1998-03-12 1999-09-22 Wella Aktiengesellschaft Agent pour colorer et decolorer des cheveux
WO2000033799A1 (fr) * 1998-12-07 2000-06-15 Wella Aktiengesellschaft Produit de coloration de fibres
WO2001028507A1 (fr) * 1999-10-20 2001-04-26 Wella Aktiengesellschaft Agent et procede pour la coloration de fibres
WO2002015855A1 (fr) * 2000-08-21 2002-02-28 L'oreal Composition de decoloration des fibres keratiniques teintes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1434560A1 *

Also Published As

Publication number Publication date
WO2003030849A8 (fr) 2004-12-29
DE10148848A1 (de) 2003-04-17
EP1434560A1 (fr) 2004-07-07

Similar Documents

Publication Publication Date Title
WO2000038636A1 (fr) Agent permettant de colorer les fibres de keratine
EP1239817B1 (fr) Utilisation de composes de methylquinolinium pour colorer des fibres keratiniques
WO2001089460A2 (fr) Agent de coloration pour fibres contenant de la keratine
EP1139988B1 (fr) Agents permettant de colorer les fibres de keratine
EP1300134B1 (fr) Agent pour teindre les fibres kératiniques avec des isophthalaldehydes
EP1758546B1 (fr) Utilisation de polyols speciaux pour inhiber la cristallisation d'aldehydes d'onium et de cetones d'onium
EP1300135B1 (fr) Agent pour la teinture des fibres kératiniques comprenant des derivés de 2-arylidène indolin-3-one
EP1292268B1 (fr) Agent de coloration de fibres keratiniques
EP1139990B1 (fr) Agent permettant de colorer les fibres de keratine
EP1362579B1 (fr) Agent pour teindre des fibres kératiniques
EP1758543B1 (fr) Utilisation de derives de quinolinium formyles speciaux, en combinaison avec des derives de diaryle substitues par amino et au moins une autre amine aromatique primaire ou secondaire
WO2003030849A1 (fr) Procede de coloration et de decoloration ulterieure de cheveux
DE19962880A1 (de) Mittel zum Färben von keratinhaltigen Fasern
EP1199065A2 (fr) Teinture de cheveux
EP1311231B1 (fr) Agent pour teindre des fibres keratiniques comprenant au moins un derive de oxocyclopentene
EP1292271B1 (fr) Agent pour teindre des fibres contenant de la keratine
EP1194116B1 (fr) Agent de coloration de fibres contenant de la keratine
DE10047480A1 (de) Mittel zum Färben von keratinhaltigen Fasern
EP1433785A1 (fr) Produits pour la teinture des fibres kératiniques
WO2001030312A1 (fr) Agent pour colorer des fibres a base de keratine
WO2001003661A1 (fr) Agent de coloration de fibres contenant de la keratine et comprenant au moins un compose aromatique nitroso
DE10218683A1 (de) Verfahren zum Betreiben eines Navigationssystems sowie Datenträger für ein Navigationssystem
DE10148842A1 (de) Mittel zum Färben von keratinhaltigen Fasern
WO2001089587A2 (fr) Agent pour la coloration de fibres keratiniques
WO2001010840A1 (fr) Azafluorenones quaternarises et leur utilisation dans des agents pour colorer des fibres a base de keratine

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU JP

AL Designated countries for regional patents

Kind code of ref document: A1

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

121 Ep: the epo has been informed by wipo that ep was designated in this application
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: 2002777203

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2002777203

Country of ref document: EP

CFP Corrected version of a pamphlet front page

Free format text: UNDER (57) PUBLISHED ABSTRACT REPLACED BY CORRECT ABSTRACT

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP