EP1317242A1 - Utilisation de derives de 4-nitro-2,1,3-benzoxadiazol comme matiere colorante dans des colorants pour fibres keratiniques - Google Patents

Utilisation de derives de 4-nitro-2,1,3-benzoxadiazol comme matiere colorante dans des colorants pour fibres keratiniques

Info

Publication number
EP1317242A1
EP1317242A1 EP01947431A EP01947431A EP1317242A1 EP 1317242 A1 EP1317242 A1 EP 1317242A1 EP 01947431 A EP01947431 A EP 01947431A EP 01947431 A EP01947431 A EP 01947431A EP 1317242 A1 EP1317242 A1 EP 1317242A1
Authority
EP
European Patent Office
Prior art keywords
nitro
benzoxadiazole
amino
benzoxadiazol
alkyl group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01947431A
Other languages
German (de)
English (en)
Inventor
Cécile Pasquier
Véronique CHARRIERE
Hans-Jürgen BRAUN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Deutschland GmbH
Original Assignee
Wella GmbH
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 Wella GmbH filed Critical Wella GmbH
Publication of EP1317242A1 publication Critical patent/EP1317242A1/fr
Withdrawn legal-status Critical Current

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
    • 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

Definitions

  • the present invention relates to coloring agents for keratin fibers, in particular human hair, which contain 4-nitro-2,1, 3-benzoxadiazole derivatives as a dye.
  • Two dyeing processes are generally used for the color-changing treatment of keratin-containing fibers, for example human hair, wool or furs.
  • the coloring is produced with so-called oxidative or permanent coloring agents, using a mixture of different developer substances and coupler substances and an oxidizing agent.
  • so-called direct dyes can be added to round off the coloring result or to create special color effects.
  • the second method uses only direct dyes, which are applied to the fibers in a suitable carrier. This procedure is easy to use, extremely mild and is characterized by little damage to the keratin fiber. A large number of requirements are imposed on the direct dyes used here.
  • the present invention relates to the use of 4-nitro-2,1,3-benzoxadiazole derivatives of the general formula (I) as a dye in colorants for keratin fibers, such as wool, silk, furs or hair, and in particular human hair,
  • X is oxygen, sulfur or NR a , with R a is hydrogen, a (C1-C4) alkyl group, a monohydroxy (C1-C4) alkyl group, a polyhydroxy (C2-C4) alkyl group, a mono ( C1 -C4) alkoxy- (C1 -C4) alkyl group;
  • R1 and R2 can be the same or different and independently of one another represent hydrogen, a halogen atom (F, Cl, Br, J), a (C1-C4) alkyl group, a (C1-C4) alkyl group substituted by a halogen atom, represents a (C1-C4) alkoxy group, a nitro group or an NR b R c group, where the radicals R b and R c can be the same or different and independently of one another are hydrogen, a (C 1 -C 4 alkyl group, an optionally substituted aromatic carbocycle or represent a (CC 4 ) alkanecarbonyl group, or R b and R c together with the nitrogen atom form a heterocyclic (C 3 -C 6 ) radical (for example an imidazolidino, piperidino, pyrrolidino, pyrazolidino, piperazino or morpholino) Form a group;
  • Q is hydrogen, an aliphatic residue, an aromatic isocyclic residue or an aromatic heterocyclic residue, preferably an aromatic monocyclic to tetracyclic residue, in particular an aromatic monocyclic or bicyclic residue.
  • X is oxygen or NR a , with R a is hydrogen, a (C1-C4) alkyl group, a monohydroxy (C1-C4) alkyl group, a polyhydroxy (C2-C4) alkyl group or a mono- (C1 -C4) alkoxy- (C1 - C4) alkyl group;
  • Q is the same as methyl, ethyl, phenyl, biphenyl, C 6 H 4 R3, C 6 H 3 R3R4 or C 6 H 2 R3R4R5, where R3, R4 and R5 may be the same or different and, independently of one another, are F, Cl, Br, I, CN, NO 2, CF 3, (C, -.
  • the 4-nitro-2,1,3-benzoxadiazole derivatives of the formula (I) are generally used in the form of a customary colorant, the
  • the amount of the compound of the formula (I) used is preferably about 0.01 to 10 percent by weight, in particular about 0.1 to 8 percent by weight.
  • the colorant may optionally contain, in addition to the dyes of the formula (I), further known direct-dyeing dyes from the group of anionic or cationic dyes, nitro dyes, azo dyes, anthraquinone dyes, triphenylmethane dyes or disperse dyes, where these dyes can be used individually or in a mixture with one another.
  • further known direct-dyeing dyes from the group of anionic or cationic dyes, nitro dyes, azo dyes, anthraquinone dyes, triphenylmethane dyes or disperse dyes, where these dyes can be used individually or in a mixture with one another.
  • the abovementioned direct dyes can be present in a total amount of about 0.01 to 4 percent by weight, the total content of dyes in the colorant according to the invention preferably being about 0.01 to 10 percent by weight, in particular 0.1 to 5 percent by weight.
  • the colorant can furthermore all known and customary additives for such preparations, for example perfume oils, complexing agents, waxes, preservatives, thickeners, alginates, guar gum, hair-care substances, such as, for example, cationic polymers or lanolin derivatives, or anionic, nonionic, amphoteric or cationic surface-active substances contain.
  • perfume oils for example perfume oils, complexing agents, waxes, preservatives, thickeners, alginates, guar gum, hair-care substances, such as, for example, cationic polymers or lanolin derivatives, or anionic, nonionic, amphoteric or cationic surface-active substances contain.
  • Amphoteric or non-ionic surface-active substances for example betaine surfactants, propionates and glycinates, such as, for example, cocoamphoglycinates or cocoamphodiglycinates, are preferably ethoxylated surfactants with 1 to 1000 ethylene oxide units, preferably with 1 to 300 ethylene oxide units, such as, for example, glyceride alkoxylates, for example castor oil which is ethoxylated with 25 ethylene oxide units, polyglycolamides, ethoxylated alcohols and ethoxylated fatty alcohols (fatty alcohol alkoxylates) and ethoxylated fatty acid sugar esters, in particular ethoxylated sorbitan fatty acid esters.
  • the abovementioned constituents are used in the amounts customary for such purposes, for example the surface-active substances in a concentration of 0.1 to 30 percent by weight, and the care substances in an amount of 0.1 to 5 percent by weight.
  • the colorant can also contain organic solvents, for example aliphatic or aromatic alcohols, such as, for example, ethanol, isopropanol, 1,2-propanediol, 1-methoxypropan-2-ol, 1-ethoxypropan-2-ol, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, benzyl alcohol, benzyloxyethanol, phenylethyl alcohol, phenoxyethanol, cinnamon alcohol and glycol ether, in particular ethanol, isopropanol or benzyl alcohol, the water content generally being about 25 to 95 percent by weight, preferably about 30 to 85 percent by weight while the content of the organic solvent or solvent mixture is about 5 to 30 percent by weight.
  • organic solvents for example aliphatic or aromatic alcohols, such as, for example, ethanol, isopropanol, 1,2-propanediol, 1-meth
  • the colorant particularly if it is a hair colorant, can be in the form of an aqueous or aqueous-alcoholic solution, a cream, a gel, an emulsion or an aerosol foam, the hair colorant being both in the form of a one-component preparation and in the form of a multicomponent preparation, for example in the form of a two-component preparation in which the dye derivative of Formula (I) is packaged separately from the other constituents and the ready-to-use hair dye is only prepared immediately before use by mixing the two components.
  • the colorant has a pH of about 3 to 10, preferably about 4 to 10. Both organic and inorganic acids or bases are suitable for adjusting the pH.
  • Suitable acids are in particular the following acids: ⁇ -hydroxycarboxylic acids, such as glycolic acid, lactic acid, tartaric acid, citric acid or malic acid; ascorbic acid; gluconolactone; Acetic acid; Hydrochloric acid or phosphoric acid, as well as mixtures of these acids.
  • Suitable bases are in particular sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, sodium phosphate, borax (Na 2 B 4 O 7 ⁇ 10H 2 O), disodium hydrogen phosphate, alkanolamines, for example monoethanolamine or triethanolamine, ammonia, aminomethylpropanol and sodium hydroxide.
  • the colorant is generally applied by applying an amount sufficient for hair coloring, depending on the length of the hair, about 30 to 120 grams, of the hair dye to the hair, the hair dye at about 15 to 45 degrees Celsius for about 1 to 60 minutes, preferably 5 for up to 30 minutes, then rinse the hair thoroughly with water, wash with a shampoo if necessary and then dry.
  • the colorant described above can furthermore contain natural or synthetic polymers or modified polymers of natural origin which are customary for cosmetic products, as a result of which hair is set at the same time as the coloring. Such agents are generally referred to as tinting or color strengthening agents.
  • polyvinylpyrrolidone polyvinyl acetate
  • polyvinyl alcohol or polyacrylic compounds such as polyacrylic acid or polymethacrylic acid
  • basic polymers of esters of polyacrylic acid polymethylacrylic acid and amino alcohols, for example their salts or quaternization products
  • polyacrylonitrile copolymers of vinyl acetate and polyvinyl acetate such as polyvinyl pyrrolidone vinyl acetate
  • natural polymers or modified natural polymers for example chitosan (deacety- lated chitin) or chitosan derivatives, can be used.
  • the aforementioned polymers can be contained in the colorant in the amounts customary for such agents, in particular in an amount of about 1 to 5 percent by weight.
  • the pH value of the tinting or color fixing agent according to the invention is preferably about 6 to 9.
  • the dye with additional setting is used in a known and customary manner by moistening the hair with the setting agent, setting (inserting) the hair for the hairstyle and subsequent drying.
  • the colorants containing the 4-nitro-2,1,3-benzoxadiazole derivatives of the general formula (I) enable an excellent, uniform, intensive and extremely durable dyeing against shampooing, light and sweat of keratin fibers (especially human hair) under gentle and skin-friendly conditions.
  • the 4-nitro-2,1,3-benzoxadiazole derivatives of the general formula (I) can also be used in oxidation coloring agents based on oxidation dye precursors. It is also possible to use the 4-nitro-2,1,3-benzoxadiazole derivatives of the general formula (I) in so-called lightening tints, in which - for the purpose of lightening the hair to be dyed or to improve gloss - the direct dyes can be used in combination with an oxidizing agent.
  • the 4-nitro-2,1,3-benzoxadiazole derivatives of the general formula (I) can be obtained by substitution of 4-nitro-2,1,3-benzoxadiazoles of the formula (II) (where Y is halogen or OCH 3 or OCH 2 is CH 3 and R1 and R2 have the same meaning as in formula (I)) with amines, alcohols, phenols, thioalcohols or thiophenols.
  • the yield is 94% of theory.
  • reaction mixture is made up to 300 ml
  • the yield is 82% of theory.
  • the coloring solution is adjusted to a pH of 10 (Examples 7 to 10) or 7.5 (Examples 11 to 12) by adding ammonia or citric acid.
  • the hair is colored by applying a sufficient amount of the dye to the bleached hair. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with lukewarm water and dried.
  • the dyeing results are summarized in Table 1 below.
  • the cetylstearyl alcohol is melted at 80 ° C. Then the lauryl ether sulfate heated to 95 ° C. together with 95% of the water is added and the mass is stirred until a cream is formed. The dye is added together with the ethanol and the remaining water at room temperature and the pH is adjusted to 9.5 by adding ammonia.
  • the hair is colored by applying a sufficient amount of hair dye cream to bleached hair. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with lukewarm water, washed with a shampoo, rinsed again with lukewarm water and then dried.
  • the L * a * b * color measurement values determined in the present examples were determined using a color measuring device from Minolta, type Chromameter II.
  • the L-value stands for the brightness (i.e. the lower the L-value, the greater the color intensity)
  • the a-value is a measure of the red component (i.e. the larger the a-value, the greater the red component is larger).
  • the b-value is a measure of the blue component of the color, the more negative the b-value, the greater the blue component.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Coloring (AREA)

Abstract

L'invention concerne l'utilisation de dérivés de 4-nitro-benzo-2,1,3-oxadiazol de formule générale (I) comme matière colorante dans des colorants pour fibres kératiniques, par exemple la laine, la soie, les fourrures ou les cheveux, notamment les cheveux humains. Dans la formule (I), X représente hydrogène, soufre ou NR<a>, R<a> représentant hydrogène, un groupe (C1-C4), un groupe monohydroxyalkyle (C1-C4), un groupe polyhydroxyalkyle (C2-C4), un groupe mono-alcoxy(C1-C4) alkyle (C1-C4) ; R1 et R2 peuvent être identiques ou différents et représentent indépendamment l'un de l'autre hydrogène, un atome d'halogène, un groupe alkyle (C1-C4), un groupe alkyle (C1-C4) substitué par un atome d'halogène, un groupe alcoxy (C1-C4), un groupe nitro ou un groupe NR<b>R<c>, dans lequel les groupes R<b> et R<c> peuvent être identiques ou différents et représentent indépendamment l'un de l'autre hydrogène, un groupe alkyle (C1-C4), un carbocycle aromatique éventuellement substitué ou un groupe alcane-carbonyle (C1-C4), ou R<b> et R<c> forment conjointement un groupe hétérocyclique (C3-C6) avec l'atome d'azote ; Q représente hydrogène, un groupe aliphatique, un groupe isocyclique aromatique ou un groupe hétérocyclique aromatique.
EP01947431A 2000-09-15 2001-06-29 Utilisation de derives de 4-nitro-2,1,3-benzoxadiazol comme matiere colorante dans des colorants pour fibres keratiniques Withdrawn EP1317242A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10045599A DE10045599B4 (de) 2000-09-15 2000-09-15 Haarfärbemittel auf der Basis von 4-Nitro-2,1,3-benzoxadiazol-Derivaten und dessen Verwendung als Farbstoff zum Färben von Haaren
DE10045599 2000-09-15
PCT/EP2001/007497 WO2002022094A1 (fr) 2000-09-15 2001-06-29 Utilisation de derives de 4-nitro-2,1,3-benzoxadiazol comme matiere colorante dans des colorants pour fibres keratiniques

Publications (1)

Publication Number Publication Date
EP1317242A1 true EP1317242A1 (fr) 2003-06-11

Family

ID=7656266

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01947431A Withdrawn EP1317242A1 (fr) 2000-09-15 2001-06-29 Utilisation de derives de 4-nitro-2,1,3-benzoxadiazol comme matiere colorante dans des colorants pour fibres keratiniques

Country Status (7)

Country Link
US (1) US6749645B2 (fr)
EP (1) EP1317242A1 (fr)
JP (1) JP2004508390A (fr)
AU (1) AU2001269112A1 (fr)
BR (1) BR0107208A (fr)
DE (1) DE10045599B4 (fr)
WO (1) WO2002022094A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7511006B2 (en) * 2000-12-14 2009-03-31 The Clorox Company Low residue cleaning solution comprising a C8 to C10 alkylpolyglucoside and glycerol
ITRM20030194A1 (it) * 2003-04-24 2004-10-25 Univ Roma Uso di derivati del 7-nitro-2, 1, 3-benzossadiazolo per
US20050282818A1 (en) * 2004-06-22 2005-12-22 Rigel Pharmaceuticals, Inc. Ubiquitin ligase inhibitors
FR2910278A1 (fr) * 2006-12-26 2008-06-27 Oreal Compositions comprenant un colorant direct et un tensioactif, procede et utilisation pour la coloration notamment eclaircissante des matieres keratiniques
FR2910277A1 (fr) * 2006-12-26 2008-06-27 Oreal Compositions comprenant un colorant direct et un epaississant, procede et utilisation pour la coloration notamment eclaircissante des matieres keratiniques
ES2304112B1 (es) * 2007-02-23 2009-08-13 Universidad De Zaragoza Uso de compuestos como inhibidores de la flavodoxina de helicobacter.
ES2304221B1 (es) * 2007-03-02 2009-09-11 Universidad De Zaragoza Composicion para el tratamiento de enfermedades infecciosas causadas por helicobacter.
ES2304220B1 (es) * 2007-03-02 2009-09-11 Universidad De Zaragoza Composicion para el tratamiento de enfermedades infecciosas.
US10640513B2 (en) 2016-02-24 2020-05-05 Ewha University - Industry Collaboration Foundation Compound and composition for detecting phosgene and diethyl chlorophosphate
KR101829451B1 (ko) * 2016-02-24 2018-02-19 이화여자대학교 산학협력단 포스젠(phosgene) 및 DCP(diethyl chlorophosphate) 검출용 화합물 및 조성물

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD277678A1 (de) * 1988-12-02 1990-04-11 Akad Wissenschaften Ddr Verfahren zur herstellung von neuen 4-(n-aryl-amino)-5,7-dinitrobenzofurazanen

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE277678C (fr)
DE228900C (fr)
DE2939304A1 (de) 1979-09-28 1981-04-16 Wella Ag Mittel und verfahren zur oxidativen faerbung von haaren
DD228900A1 (de) * 1984-09-07 1985-10-23 Univ Halle Wittenberg Verfahren zur bestimmung langkettiger aliphatischer amine
US5055110A (en) 1989-11-22 1991-10-08 Clairol Incorporated Benzoxazine dyes
DE19962880A1 (de) 1999-12-24 2001-06-28 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD277678A1 (de) * 1988-12-02 1990-04-11 Akad Wissenschaften Ddr Verfahren zur herstellung von neuen 4-(n-aryl-amino)-5,7-dinitrobenzofurazanen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO0222094A1 *

Also Published As

Publication number Publication date
US6749645B2 (en) 2004-06-15
BR0107208A (pt) 2002-07-09
DE10045599A1 (de) 2002-04-04
DE10045599B4 (de) 2004-06-03
JP2004508390A (ja) 2004-03-18
US20020189032A1 (en) 2002-12-19
AU2001269112A1 (en) 2002-03-26
WO2002022094A1 (fr) 2002-03-21

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