WO2000076466A1 - Derives de xanthene pour teindre des fibres contenant de la keratine - Google Patents

Derives de xanthene pour teindre des fibres contenant de la keratine Download PDF

Info

Publication number
WO2000076466A1
WO2000076466A1 PCT/EP2000/005044 EP0005044W WO0076466A1 WO 2000076466 A1 WO2000076466 A1 WO 2000076466A1 EP 0005044 W EP0005044 W EP 0005044W WO 0076466 A1 WO0076466 A1 WO 0076466A1
Authority
WO
WIPO (PCT)
Prior art keywords
amino
group
acid
methyl
hydroxy
Prior art date
Application number
PCT/EP2000/005044
Other languages
German (de)
English (en)
Inventor
Hinrich Möller
Bernd Meinigke
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 AU58106/00A priority Critical patent/AU5810600A/en
Publication of WO2000076466A1 publication Critical patent/WO2000076466A1/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
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes

Definitions

  • the invention relates to an agent for dyeing keratin-containing fibers, in particular human hair, which contains xanthene derivatives, the use of these xanthene derivatives as a coloring component in hair dye compositions and a process for dyeing keratin-containing fibers, in particular human hair.
  • keratin fibers e.g. B. hair, wool or fur
  • 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
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof are usually used as developer components used.
  • Special representatives are, for example, p-phenylenediamine, p-toluenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- (2.5 - diaminophenyethanol, 2- (2,5-diaminophenoxy) ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazolon-5, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2 -Hydroxy-methyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives are generally used as coupler components.
  • coupler substances are ⁇ -naphthol, 1, 5-, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-diaminophenoxyethanol , 2-amino-4- (2-hydroxyethylamino) anisole (Lehmanns Blau), 1-phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1, 3-bis- (2, 4-diaminophenoxy) propane, 2-chlororesorcinol, 4- %
  • Chlororesorcinol 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 3-amino-6-methoxy-2-methylamino-pyridine and 3,5-diamino-2,6-dimethoxypyridine.
  • oxidation dyes intensive dyeings can be achieved with good fastness properties, but the development of the color is usually done under the influence of oxidizing agents such. B. H 2 O 2 , which in some cases can damage the fiber. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors can sometimes have a sensitizing effect on people with sensitive skin. Direct dyes are applied under gentler conditions, but their disadvantage is that the dyeings often have inadequate fastness properties.
  • the object of the present invention is to provide colorants for keratin fibers, in particular human hair, which are qualitatively at least equivalent to the usual oxidation hair colorants in terms of color depth, gray coverage and fastness properties, but without necessarily relying on oxidizing agents such as e.g. B. H 2 O 2 to be instructed.
  • the colorants may have no or only a very low sensitization potential.
  • the xanthene derivatives shown in the formula I are also outstandingly suitable for dyeing keratin-containing fibers in the absence of oxidizing agents. They result in colorations with outstanding brilliance and depth of color and lead to diverse color nuances. However, the use of oxidizing agents should not be excluded in principle.
  • the invention relates to an agent for dyeing keratin fibers, in particular human hair, containing at least one xanthene derivative of the formula I,
  • R 1 represents a hydrogen atom, a C 1-4 carboxyl or a sulfo group
  • R 2 , R 3 , R ⁇ R 5 stand for a hydrogen atom, a C 1 -C 4 alkyl group, CC 4 alkoxy group or hydroxy group, and if X 2 stands for an oxygen atom, then X 1 is a hydroxy group which can also be present as an alkali, alkaline earth or ammonium salt, or when X 1 represents an amino group which can optionally carry one or two methyl substituents or together with R 2 and / or R 3 a fused 5-, 6- or 7-membered ring, then X 2 is a group + NA 1 A 2 U " , in which A 1 and A 2 independently of one another represent hydrogen or a methyl group or together with R 4 and / or R 5 a fused 5-, 6th - or 7-membered ring form and U " stands for an equivalent of a halide, sulfate, sulfonate or carboxylate anion, or physiologically acceptable salts thereof.
  • Keratin-containing fibers are wool, furs, feathers and in particular human hair.
  • the colorants according to the invention can also be used for dyeing other natural fibers, such as, for. B. cotton, jute, sisal, linen or silk, modified natural fibers, such as. B. regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as. B. polyamide, polyacrylonitrile, polyurethane and polyester fibers can be used.
  • the compounds with the formula I are preferably selected from the group of the following xanthene derivatives pyrogallol red, 9-phenyl-2,6,7-trihydroxy-3-fluorene, rhodamine 116 perchlorate, rhodamine 101, rhodamine-110 chloride, fluorescein and any of these Mixtures.
  • xanthene derivatives with the formula I are preferably used in the agents according to the invention in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the total colorant. They can be used as direct coloring agents as the only coloring component or both in a mixture with other direct drawing agents and also in the presence of conventional oxidation dye precursors or other hair coloring systems.
  • Coloring agents which contain the xanthene derivatives with the formula I alone as the coloring component are preferably used for coloring in the range from red-orange, red-brown and violet. Colorings with an even higher brilliance and improved fastness properties (light fastness, wash fastness, rub fastness) over a wide range of shades from orange, red, brown orange, medium brown, violet, dark violet to blue black and black are achieved if the compounds used according to the invention with formula I together with at least one further component (hereinafter referred to as component B), selected from compounds having a primary or secondary amino group or hydroxyl group, selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, from 2 to 9 amino acids, oligopeptides and aromatic hydroxy compounds , and / or CH-active compounds can be used.
  • component B further component selected from compounds having a primary or secondary amino group or hydroxyl group, selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, from
  • the above-mentioned compounds of component B can be used in an amount of 0.03 to 65, in particular 1 to 40 mmol, in each case based on 100 g of the total colorant.
  • reaction products which are reaction products of xanthene derivatives of the formula I with the compounds of component B mentioned as direct colorants.
  • reaction products can e.g. B. can be obtained by briefly heating the two components in stoichiometric amounts in an aqueous neutral to weakly alkaline medium, where they either precipitate out of the solution as a solid or are isolated therefrom by evaporation of the solution.
  • 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, N, N-diethyl, N- (2-hydroxyethyl) -N-ethyl, N, N-bis (2-hydroxyethyl) -, N- (2 -Methoxyethyl-), 2,3-, 2,4-, 2,5-dichloro-p-phenylene diamine, 2-chloro-p-phenylene diamine, 2,5-dihydroxy-4-morpholinoaniline dihydrobromide, 2-, 3- , 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, o-, p-phenylenediamine, o-toluenediamine, 2,5-diaminotoluene, -phenol, - phenethole, 4-amino-3- methylphenol, 2- (2,5-diaminopheny
  • R 7 , R 8 , R 9 , R 0 and R 11 represents hydrogen, a hydroxy or an amino group which can be substituted by C 1-4 alkyl, C 1-4 hydroxyalkyl, C 1-4 alkoxy, C 1-4 aminoalkyl or C ⁇ alkoxy-C ⁇ alkyl groups can be substituted, and
  • Q for a direct bond, a saturated or unsaturated carbon chain with 1 to 4 carbon atoms optionally substituted by hydroxy groups, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom, or a group with the formula
  • Y is a direct bond, a CH 2 or CHOH group, Z and Z independently of one another for an oxygen atom, an NR 12 group in which R 12 is hydrogen, a C 1-4 alkyl or a hydroxy-C ⁇ alkyl group, the group O- (CH 2 ) p -NH or NH- (CH 2 ) p '-0, where p and p' are 2 or 3, and o is a number from 1 to 4, such as 4,4'-diaminostilbene and its hydrochloride, 4,4'-diaminostilbene - 2,2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene and its hydrochlorind, 4,4'-diaminodiphenylmethane, sulfide, sulfoxide, amine, 4,4 ' -Diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzoph
  • 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-, 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-dihydroxy-5,6-diamino-, 4,5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2-hydroxy-4 , 5,6-triamino-, 2,4,5,6-tetraamino-, 2-methyiamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-amin
  • Suitable aromatic hydroxy compounds are e.g. B. 2-, 4-, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, Phloroglucin, hydroxyhydroquinone, 2-, 3-, 4-methoxy, 3-dimethylamino, 2- (2-hydroxyethyl) -, 3,4-methylenedoxoxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, phenylacetic acid , Gallic acid, 2,4,6-tr ⁇ hydroxybenzoic acid, -acetophenone, 2-, 4-chloro-resorcinol, 1-naphthol, 1, 5-, 2,3-, 2,7-dihydroxy-naphthalene, 6-dimethyl-4-hydroxy-2 - Naphthahnsulfonsaure, 3,6-D ⁇ hydroxy-2,7-naphthal ⁇ nsulfon
  • CH-active compounds which may be mentioned are 1, 2,3,3-tetramethyl-3H-indolumium, 1, 2,3,3-tetramethyl-3H-indolum-p-toluenesulfonate, 1, 2,3,3-tetramethyl - 3H- ⁇ ndol ⁇ um methanesulfonate, Fischer's base (1, 3,3-T ⁇ methyl-2-methylen ⁇ ndol ⁇ n), 2,3-dimethyl-benzothiazo umiodide, 2,3-dimethyl-benzoth ⁇ azol ⁇ um-p-toluenesulfonate, rhodanine, Rhodan ⁇ n-3- Ess ⁇ gsaure, 1-methyl-2-ch ⁇ nald ⁇ n ⁇ um- ⁇ od ⁇ d, 1-ethyl-2-ch ⁇ nald ⁇ n ⁇ um- ⁇ od ⁇ d, 1, 4-dimethylquinonium iodide, barbituric acid, thiobarbituric acid, 1, 3-di
  • Preferred amino acids are all naturally occurring and synthetic ⁇ -amino acids, for. B the amino acids accessible by hydrolysis from vegetable or animal proteins, e.g. collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein. Both acidic and alkaline amino acids can be used. Preferred amino acids are arginine, histidine, tyrosine, phenylalanine, DOPA (dihydroxyphenylalanine), ornithine, lysine and tryptophan. However, other amino acids, such as 6-aminocaproic acid, can also be used
  • the oligopeptides can be naturally occurring or synthetic oligopeptides, but also the oligopeptides contained in polypeptide or protein hydrolyzates, provided they have sufficient water solubility for use in the colorants according to the invention.
  • Examples include glutathione and those in the hydrolysates of Oligopeptides containing collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein are preferred.
  • Agents which contain the compounds of the formula I together with compounds having a primary or secondary amino group or with aromatic hydroxy compounds are preferred 3
  • the compounds of component B are particularly preferably selected from the group consisting of N- (2-hydroxyethyl) -N-ethyl-, 2-chloro-p-phenylenediamine, N, N- bis (2-hydroxyethyl) -p-phenylenediamine, 4-aminophenol, p-phenylenediamine, 2- (2,5-diaminophenyl) ethanol, 2,5-diaminotoluene, 3,4-methylenedioxyaniline, 2-amino-4- (2-hydroxyethylamino) anisole, 2- (2nd , 4-diaminophenoxy) ethanol, 3-amino-2,4-dichloro, 2-methyl-5-amino, 3-methyl-4-amino, 2-methyl-5- (2-hydroxyethylamino) -, 2-methyl-5-amino-4-chloro, 6-methyl-3-amino-2-chloro, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4
  • Oxidizing agents e.g. B. H 2 O 2
  • 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 .
  • the colorants according to the invention contain, in addition to the compounds according to the invention, customary direct dyes, for example, for further modification of the color shades.
  • customary direct dyes for example, for further modification of the color shades.
  • B. from the group of nitro phenylenediamines, nitroaminophenols, anthraquinones or indophenols, such as. B.
  • HC Yellow 2 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 and Basic Brown 17 known compounds as well as picramic acid 2-amino-6-chloro-4-nitrophenol, 4-amino-2-nitrodiphenylamine -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'-hydroxyethyl) aminobenzene.
  • the inventive agents according to this embodiment contain the 40 direct dyes preferably in an amount of 0.01 to 20 wt .-%, based on the total colorant.
  • preparations according to the invention can also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • preparations according to the invention can also contain reactive carbonyl compounds, such as aldehydes and other oxo compounds in combination with suitable amines, phenols or CH-active compounds, as are described in many patents.
  • reactive carbonyl compounds such as aldehydes and other oxo compounds in combination with suitable amines, phenols or CH-active compounds, as are described in many patents.
  • oxidation dye precursors or the optional direct dyes each represent uniform compounds. Rather, in the colorants according to the invention, due to the production process for the individual dyes, further components may be present in minor amounts, provided that these do not adversely affect the coloring result or for other reasons, e.g. B. toxicological, must be excluded.
  • the colorants according to the invention produce intensive colorations even at physiologically tolerable temperatures of below 45 ° C. They are therefore particularly suitable for dyeing human hair.
  • the colorants can usually be incorporated into a water-containing cosmetic carrier.
  • Suitable water-containing cosmetic carriers are e.g. B. creams, emulsions, gels or surfactant-containing foaming solutions such.
  • the colorants according to the invention can contain all active substances, additives and auxiliaries known in such preparations.
  • the colorants contain at least one surfactant, in principle both anionic and ZwA zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases, however, it has proven advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • Suitable anionic surfactants in preparations according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group,
  • Ether carboxylic acids of the formula RO- (CH 2 -CH 2 O) x -CH 2 -COOH, in which R is a linear alkyl group with 10 to 22 C atoms and x 0 or 1 to 16, acyl sarcosides with 10 to 18 C- Atoms in the acyl group, acyl taurides with 10 to 18 C atoms in the acyl group, acyl isethionates with 10 to 18 C atoms in the acyl group,
  • Mono and dialkyl sulfosuccinic acid with 8 to 18 carbon atoms in the alkyl group and mono alkyl polyoxyethyl sulfosuccinate 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 the addition products of about 2 to 15 molecules of ethylene oxide and / or propylene oxide to 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 those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO ⁇ or -S ⁇ 3 H group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammonium glycinate, for example the 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 cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C 8 . 18 -alkyl or -acyl group in the molecule contain at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts.
  • 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. ⁇ J
  • 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 hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • Ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride.
  • 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 Am ⁇ d®S 18, are characterized not only by a good conditioning effect, but also by their good biodegradability
  • estersquats such as the methylhydroxyalkyldialkoyloxyalkylammonium marketed under the trade Stepantex® ®
  • quaternary sugar derivative that can be used as a cationic surfactant is the commercial product Glucquat®100, according to the CTFA nomenclature a "lauryl methyl gluceth-10 hydroxypropyl dimonium chloride"
  • the compounds with alkyl groups used as surfactants can in each case be uniform substances. However, it is generally preferred to use native 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 narrow homolog distribution can be used.
  • "Normal" homolog distribution is 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, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts The use of products with a narrow homolog distribution can be preferred
  • nonionic polymers such as, for example, vinyl pyrrolidone / vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone / vinyl acetate copolymers and polysiloxanes
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallylammonium chloride copolymers, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, vinylpyrrolidone copolymers
  • Imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as, for example, acrylic amidopropyl-trimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert.-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers such as polyesters, anionic polyesters - Acids, vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate
  • Copolymers vinyl acetate / butyl maleate / isobomylacrylate 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 cum, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such. B. bentonite or fully synthetic hydrocolloids such.
  • Protein hydrolyzates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids and quaternized protein hydrolyzates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol,
  • Anti-dandruff agents such as piroctone olamine and zinc omadine, other substances for adjusting the pH value,
  • Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and their salts, plant extracts and vitamins, cholesterol, light stabilizers, Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as 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
  • the constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose; z.
  • 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.
  • Suitable metal salts are e.g. B. 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, in particular 1 to 40, mmol based on 100 g of the total colorant.
  • the pH of the ready-to-use coloring preparations is usually between 2 and 11, preferably between 5 and 9.
  • Another object of the present invention relates to the use of xanthene derivatives having the formula I.
  • R 1 represents a hydrogen atom, a CC 4 carboxyl or a sulfo group
  • R 2 , R 3 , R 4 , R 5 represent a hydrogen atom, a C 1 -C 4 alkyl group, C r C 4 alkoxy group or a hydroxyl group, if X 2 represents an oxygen atom, then X 1 is a hydroxyl group , which can also be in the form of an alkali, alkaline earth or ammonium salt, or if X 1 represents an amino group which can optionally carry one or two methyl substituents or together with R 2 and / or R 3 a fused 5-, 6th - or forms a 7-membered ring, then X 2 is a group + NA 1 A 2 U " , in which A 1 and A 2 independently represent hydrogen or a methyl group or together with R 4 and / or R 5 is a fused-on 5- , 6- or 7- membered ring form and U " stands for an equivalent of a halide, sulfate, sulfonate or carboxylate anion, or their physiological
  • Yet another object of the present invention relates to a process for dyeing keratin-containing fibers, in particular human hair, in which a colorant comprising A) at least one xanthene derivative with the formula I, M
  • R 1 represents a hydrogen atom, a C 1 -C 4 carboxyl or a sulfo group
  • R 2 , R 3 , R 4 , R 5 stand for a hydrogen atom, a C ⁇ C ⁇ alkyl group, C r C 4 alkoxy group or hydroxy group, if X 2 stands for an oxygen atom, then X 1 is a hydroxy group which can also be present as an alkali, alkaline earth or ammonium salt, or if X 1 represents an amino group which can optionally carry one or two methyl substituents or together with R 2 and / or R 3 a fused 5-, 6- or 7-membered ring forms, then X 2 is a group + NA 1 A 2 U ' , wherein A 1 and A 2 independently of one another represent hydrogen or a methyl group or together with R 4 and / or R 5 a fused 5-, 6th - or 7-membered ring form and U " stands for an equivalent of a halide, sulfate, sulfonate or carboxylate anion, or their physiologically acceptable salts and B) at
  • the xanthene derivatives of the formula I and the compounds of component B can either be applied to the hair simultaneously or else in succession, it being irrelevant which of the two components is applied first.
  • the optionally contained ammonium or metal salts can be added to the first or the second component. There may be an interval of up to 30 minutes between the application of the first and the second component. Pretreatment of the fibers with the saline solution is also possible.
  • the xanthene derivatives of the formula I and the compounds of component B 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. When stored separately, the reactive components are only intimately mixed with one another immediately before use. In dry storage, a defined amount of warm (30 to 80 ° C) water is usually added before use and a homogeneous mixture is produced.
  • a slurry of 5 mmol of a xanthene derivative with the formula I, possibly 5 mmol of an oxidation dye precursor of component B and 5 mmol of sodium acetate and a drop of a 20% strength fatty alkyl ether sulfate solution in 50 ml of water at 60 ° C. were prepared. The slurries were mixed together after cooling to 30 ° C and adjusted to pH 6 with dilute NaOH or hydrochloric acid.
  • a strand of 90% gray, untreated human hair was placed in this coloring solution at 30 ° C. for 30 minutes.
  • the tress was then rinsed with lukewarm water for 30 seconds, dried with warm air and then combed out.
  • the color depth was rated on the following scale:

Landscapes

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

Abstract

Produit permettant de teindre des fibres contenant de la kératine, en particulier des cheveux humains, qui contient au moins un dérivé de xanthène de formule (I), dans laquelle R1 représente un atome d'hydrogène, un groupe carboxyle C¿1?-C4 ou sulfo, R?2, R3, R4, R5¿ représentent un atome d'hydrogène, un groupe alkyle C¿1?-C4, un groupe alcoxy C1-C4 ou un groupe hydroxy. Lorsque X?2¿ représente un atome d'oxygène, X1 représente un groupe hydroxy qui peut être également présent sous forme de sel alcalin, alcalino-terreux ou d'ammonium, ou, lorsque X1 représente un groupe amino, qui peut éventuellement porter un ou deux substituants méthyle ou forme conjointement avec R2 et/ou R3 un noyau condensé à 5, 6 ou 7 chaînons, X2 représente un groupe ?+NA1A2 U-¿, dans lequel A1 et A2 représentent indépendamment l'un de l'autre hydrogène ou un groupe méthyle, ou forment conjointement avec R4 et/ou R5 un noyau condensé à 5, 6 ou 7 chaînons et U- représente un équivalent d'un anion d'halogénure, de sulfate, de sulfonate ou de carboxylate. La présente invention concerne également des sels physiologiquement acceptables desdits produits.
PCT/EP2000/005044 1999-06-10 2000-06-02 Derives de xanthene pour teindre des fibres contenant de la keratine WO2000076466A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU58106/00A AU5810600A (en) 1999-06-10 2000-06-02 Xanthene derivatives for dying keratin fibers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19926377.9 1999-06-10
DE1999126377 DE19926377A1 (de) 1999-06-10 1999-06-10 Mittel zum Färben von keratinhaltigen Fasern

Publications (1)

Publication Number Publication Date
WO2000076466A1 true WO2000076466A1 (fr) 2000-12-21

Family

ID=7910731

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/005044 WO2000076466A1 (fr) 1999-06-10 2000-06-02 Derives de xanthene pour teindre des fibres contenant de la keratine

Country Status (3)

Country Link
AU (1) AU5810600A (fr)
DE (1) DE19926377A1 (fr)
WO (1) WO2000076466A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1972327A1 (fr) * 2007-03-20 2008-09-24 L'Oreal Utilisation pour la coloration des fibres kératiniques d'une composition comprenant un composé halochromique et / ou le colorant correspondant à ce composé
US7467094B2 (en) 1999-06-23 2008-12-16 Visicu, Inc. System and method for accounting and billing patients in a hospital environment
CN102276735A (zh) * 2011-05-05 2011-12-14 淮海工学院 纤维素基多功能螯合材料及其制备方法和应用
EP2428230A1 (fr) * 2008-12-25 2012-03-14 Canon Kabushiki Kaisha Sonde pour cellules auditives ciliées.
CN104672198A (zh) * 2013-11-26 2015-06-03 住友化学株式会社 化合物及着色固化性树脂组合物

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2830192B1 (fr) 2001-09-28 2004-08-20 Oreal Composition tinctoriale comprenant une base d'oxydation du type diaminopyrazole et un coupleur pyrazolo-azole
FR2830189B1 (fr) * 2001-09-28 2004-10-01 Oreal Composition de teinture a effet eclaircissant pour fibres keratiniques humaines
US7736631B2 (en) 2003-04-01 2010-06-15 L'oreal S.A. Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing
FR2853235B1 (fr) * 2003-04-01 2008-10-03 Oreal Composition de coloration pour matieres keratiniques humaines comprenant un colorant fluorescent et un compose particulier a fonction acide, procede et utilisation
EP1627025B1 (fr) 2003-05-09 2016-10-12 Applied Biosystems, LLC Materiaux polymeriques fluorescents contenant des colorants de rhodamine liposolubles
US7491830B2 (en) 2003-05-09 2009-02-17 Applied Biosystems Inc. Phenyl xanthene dyes
DE102004002601A1 (de) * 2004-01-15 2005-08-04 Beiersdorf Ag Visualisierung von Sonnenschutzmitteln auf der Haut
FR2889060B1 (fr) * 2005-08-01 2009-05-15 Oreal Composition de teinture des fibres keratiniques comprenant un colorant direct amidoxanthenique et procede de teinture l a mettant en oeuvre
FR2889059B1 (fr) * 2005-08-01 2007-10-26 Oreal Composition de teinture des fibres keratiniques comprenant un colorant direct amidoxanthenique et procede de teinture la mettant en oeuvre
FR2889064B1 (fr) * 2005-08-01 2007-10-26 Oreal Composition de teinture des fibres keratiniques comprenant un colorant direct amidoxanthenique et procede de teinture la mettant en oeuvre
FR3067601B1 (fr) * 2017-06-16 2020-01-10 L'oreal Procede de coloration des matieres keratiniques mettant en œuvre au moins un colorant auto-oxydable ou colorant d’oxydation bleu, violet ou vert et au moins un colorant fluorescent

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1377695A (en) * 1972-02-21 1974-12-18 Ici Ltd Reactive dyestuffs
US4425132A (en) * 1978-04-06 1984-01-10 L'oreal Two-stage process for dyeing keratin fibres
US5094662A (en) * 1990-11-13 1992-03-10 Shiseido Co. Ltd. Product for improved permanent waving of hair and simultaneously coloring and permanently waving hair and method therefor
US5188639A (en) * 1990-11-13 1993-02-23 Shiseido Co., Ltd. Product for improved permanent waving of hair and simultaneously coloring and permanently waving hair and method therefor
GB2259717A (en) * 1991-09-20 1993-03-24 Kao Corp Hair dye composition
US5356438A (en) * 1992-10-16 1994-10-18 Pacific Corporation Hair color rinse composition containing haloginated fluorescein dyes
JPH08174940A (ja) * 1994-12-27 1996-07-09 Mita Ind Co Ltd 画像記録装置
EP0806198A2 (fr) * 1996-05-09 1997-11-12 Wella Aktiengesellschaft Composition de teinture

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1377695A (en) * 1972-02-21 1974-12-18 Ici Ltd Reactive dyestuffs
US4425132A (en) * 1978-04-06 1984-01-10 L'oreal Two-stage process for dyeing keratin fibres
US5094662A (en) * 1990-11-13 1992-03-10 Shiseido Co. Ltd. Product for improved permanent waving of hair and simultaneously coloring and permanently waving hair and method therefor
US5188639A (en) * 1990-11-13 1993-02-23 Shiseido Co., Ltd. Product for improved permanent waving of hair and simultaneously coloring and permanently waving hair and method therefor
GB2259717A (en) * 1991-09-20 1993-03-24 Kao Corp Hair dye composition
US5356438A (en) * 1992-10-16 1994-10-18 Pacific Corporation Hair color rinse composition containing haloginated fluorescein dyes
JPH08174940A (ja) * 1994-12-27 1996-07-09 Mita Ind Co Ltd 画像記録装置
EP0806198A2 (fr) * 1996-05-09 1997-11-12 Wella Aktiengesellschaft Composition de teinture
DE19618595A1 (de) * 1996-05-09 1997-11-13 Wella Ag Färbemittel

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 118, no. 18, 3 May 1993, Columbus, Ohio, US; abstract no. 170816t, KEVIN LEY ET AL: "The use of scanning photometer microscopy to investigate dyeing of ortho and para cortical cells" page 88; XP002150894 *
KONSTANTINOVA T ET AL: "The Synthesis, Properties and Application of Some 9-Phenylxanthene Dyes", DYES AND PIGMENTS,GB,ELSEVIER APPLIED SCIENCE PUBLISHERS. BARKING, vol. 38, no. 1-3, 15 July 1998 (1998-07-15), pages 11 - 18, XP004121021, ISSN: 0143-7208 *
PATENT ABSTRACTS OF JAPAN vol. 1996, no. 11 29 November 1996 (1996-11-29) *
PROC. INT. WOOL TEXT.RES. CONF., 8TH, vol. 1, 1990, pages 225 - 234 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7467094B2 (en) 1999-06-23 2008-12-16 Visicu, Inc. System and method for accounting and billing patients in a hospital environment
EP1972327A1 (fr) * 2007-03-20 2008-09-24 L'Oreal Utilisation pour la coloration des fibres kératiniques d'une composition comprenant un composé halochromique et / ou le colorant correspondant à ce composé
FR2913882A1 (fr) * 2007-03-20 2008-09-26 Oreal Utilisation pour la coloration des fibres keratiniques d'une composition comprenant un compose halochromique et/ou le colorant correspondant a ce compose
US7641703B2 (en) 2007-03-20 2010-01-05 L'oreal S.A. Composition for the coloring of keratinous fibers comprising a halochromic compound and/or the dye corresponding to this compound, and method of use thereof
EP2428230A1 (fr) * 2008-12-25 2012-03-14 Canon Kabushiki Kaisha Sonde pour cellules auditives ciliées.
US8460639B2 (en) 2008-12-25 2013-06-11 Canon Kabushiki Kaisha Probe for a hair cell, and labelling method for a hair cell using the probe for a hair cell
CN102276735A (zh) * 2011-05-05 2011-12-14 淮海工学院 纤维素基多功能螯合材料及其制备方法和应用
CN104672198A (zh) * 2013-11-26 2015-06-03 住友化学株式会社 化合物及着色固化性树脂组合物
CN104672198B (zh) * 2013-11-26 2018-11-16 东友精细化工有限公司 化合物及着色固化性树脂组合物

Also Published As

Publication number Publication date
AU5810600A (en) 2001-01-02
DE19926377A1 (de) 2000-12-14

Similar Documents

Publication Publication Date Title
WO2000038636A1 (fr) Agent permettant de colorer les fibres de keratine
WO2001003651A2 (fr) Substance destinee a la teinture de fibres keratiniques
EP0977546A1 (fr) Utilisation d'aldehydes insatures pour colorer des fibres a base de keratine
WO2000076466A1 (fr) Derives de xanthene pour teindre des fibres contenant de la keratine
WO2000038632A1 (fr) Procede permettant de colorer les fibres de keratine au moyen de derives de l'acide 2-oxocarboxylique associes a des nucleophiles
WO2000015184A1 (fr) Procede de coloration de fibres contenant de la keratine a l'aide de sels de diazonium stables
EP1028694A1 (fr) Utilisation d'indanones pour colorer des fibres a base de keratine
WO2001089460A2 (fr) Agent de coloration pour fibres contenant de la keratine
WO1998047472A1 (fr) Utilisation d'isatines 1-substituees pour la coloration de fibres keratiniques
EP1139988B1 (fr) Agents permettant de colorer les fibres de keratine
DE19845481A1 (de) Verwendung von Ninhydrinderivaten zum Färben von keratinhaltigen Fasern
WO1999018917A2 (fr) Agent de coloration pour fibres a base de keratine, a teneur en acide dehydroascorbique
EP1139990B1 (fr) Agent permettant de colorer les fibres de keratine
WO1999019558A2 (fr) Utilisation de derives de malonaldehyde pour colorer des fibres contenant de la keratine
EP1194116B1 (fr) Agent de coloration de fibres contenant de la keratine
WO2000038634A1 (fr) Agents permettant de colorer les fibres de keratine
WO2001005359A2 (fr) Substance destinee a teindre des fibres contenant de la keratine
WO2000015183A1 (fr) Produit de coloration de fibres contenant de la keratine
WO2001003661A1 (fr) Agent de coloration de fibres contenant de la keratine et comprenant au moins un compose aromatique nitroso
WO2001030312A1 (fr) Agent pour colorer des fibres a base de keratine
WO2001010840A1 (fr) Azafluorenones quaternarises et leur utilisation dans des agents pour colorer des fibres a base de keratine
EP0998256A1 (fr) Utilisation de di- et d'oligoacylaromatiques pour colorer des fibres a base de keratine
WO2001089587A2 (fr) Agent pour la coloration de fibres keratiniques

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

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

AL Designated countries for regional patents

Kind code of ref document: A1

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

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)
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP