WO1991003231A1 - Procede de teinture des cheveux au moyen de colorants directs - Google Patents

Procede de teinture des cheveux au moyen de colorants directs Download PDF

Info

Publication number
WO1991003231A1
WO1991003231A1 PCT/EP1990/001420 EP9001420W WO9103231A1 WO 1991003231 A1 WO1991003231 A1 WO 1991003231A1 EP 9001420 W EP9001420 W EP 9001420W WO 9103231 A1 WO9103231 A1 WO 9103231A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
group
hydrogen
carbon atoms
heterocyclic ring
Prior art date
Application number
PCT/EP1990/001420
Other languages
German (de)
English (en)
Inventor
Iduna Matzik
Horst Höffkes
Hinrich Möller
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 KR1019920700440A priority Critical patent/KR927002998A/ko
Publication of WO1991003231A1 publication Critical patent/WO1991003231A1/fr
Priority to NO92920336A priority patent/NO920336L/no
Priority to FI920897A priority patent/FI920897A0/fi

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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/418—Amines containing nitro groups
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil

Definitions

  • the invention relates to a process for dyeing hair using direct hair dyes, a preparation which contains a leveling aid to increase the uniformity of the dye application being applied to the hair either before or simultaneously with the application of a direct hair dye.
  • Direct hair dyes In addition to the oxidation dyes which are formed from oxidation dye precursors by oxidative coupling, the direct hair dyes play an important role in dyeing hair. Direct hair dyes have the advantage that they are used without the addition of oxidizing agents.
  • the main direct dyes are nitrobenzene derivatives, e.g. B. nitrophenylenediamines and nitroaminophenols, antrachinone dyes, azo compounds and indophenols in question. Because of the lower fastness properties, direct dyes are mostly only used for temporary or semi-permanent hair dyeing.
  • this goal can be achieved by a process for dyeing the hair, which is characterized in that a preparation is applied to the hair prior to or simultaneously with the application of a direct hair dye, which is used as an aid for increasing the uniformity of the color application contains a 5- or 6-membered heterocyclic ring compound which has a grouping of the formulas I - VI in the ring,
  • ethylene 1,2-propylene, trimethylene, vinylene, propenylene, 1-ethanyl-2-ylidene, 1-propanyl-3-ylidene and 1-propenyl-3 -ylidene groups are understood.
  • the preparation containing the leveling aid to be used according to the invention before the application of the direct hair dye this can preferably be done in the form of an aqueous preparation, e.g. B. a shampoo or conditioner, which the heterocyclic ring compound, possibly together with formulation aids and contains hair cosmetic active ingredients.
  • the leveling aid is preferably contained in such a preparation in an amount of 0.1-5% by weight.
  • further formulation auxiliaries include, in particular, water-soluble surface-active substances in an amount of 0.1-10% by weight, water-soluble, polymeric thickeners in an amount of 0.1
  • hair cosmetic active ingredients such.
  • leveling aid to be used according to the invention is to be applied to the hair at the same time as the substantive hair dye, a suitable heterocyclic ring compound is incorporated directly into the hair dye.
  • the 5- or 6-membered heterocycles which are suitable according to the invention as leveling aids are predominantly known from the literature, and derivatives which may not be known from the literature can be easily synthesized by customary processes for the preparation of such ring systems.
  • heterocyclic ring compounds from the group urazole, hexahydropyrimidin-2-one, 1,3-bis (2-hydroxyethyl) imidazolidin-2-one, imidazol-2-one, hydantoin, parabanic acid, barbituric acid , Pyrrolidin-2-one, imidazole, 2-aminoimidazole, 1,2,4-triazole, 2-aminopyrimidine, 2-aminothiazoline and 1,2,3-triazole are used as leveling agents.
  • Particularly preferred among the 5- or 6-membered heterocyclic ring compounds mentioned are those which contain a group of the formula -NR 1 -CO-NR 1 - in the ring, in which R 1 is hydrogen, an alkyl group with 1-4 C- Atoms or a hydroxyalkyl group with 2-4 C atoms.
  • the leveling aid is preferably contained in the preparation in an amount of 0.1-5% by weight.
  • Suitable direct hair dyes are all dyes suitable for dyeing hair under physiologically acceptable conditions, ie in particular those dyes which attract hair keratin at temperatures below + 40 ° C. These are especially nitrobenzene dyes, e.g. B. nitrophenylenediamines, nitroaminophenols, antrachinone dyes, naphthoquinones and azo compounds.
  • Suitable direct dyes for hair dyeing can be found in relevant manuals, e.g. B. from "The Chemistry of Synthetic Dyes” (edited by K. Venkataraman, Academic Press 1971 New York and London), Vol. V, Chapter VII (Hair Dyes), pages 507-529. Examples of suitable direct pulling hair dyes are e.g. B.
  • the substantive hair dyes are usually contained in the preparations for hair coloring according to the invention in amounts of 0.05-5.0% by weight.
  • the hair colorants according to the invention can also contain oxidation dye precursors for shading and producing natural shades.
  • an oxidizing agent e.g. B. of hydrogen peroxide to initiate the oxidative development of the oxidation dye.
  • the direct hair dye compositions according to the invention can also contain further auxiliaries. Among these, special mention should be made
  • - Hair cosmetic active ingredients e.g. B. water-soluble, cationic polymers, glucose, D-panthenol, water-soluble proteins, protein degradation products or protein derivatives, cholesterol, vitamins, plant extracts, saponins or antiseborrheic agents and
  • pH adjusting agents and buffer substances e.g. B. Triethanolamine, sodium citrate
  • the direct dyes, the leveling aid and the other dyeing aids are incorporated into a suitable cosmetic carrier.
  • the preparations according to the invention are aqueous solutions of the direct dyes, the leveling aid and possibly other auxiliaries.
  • Gels, cream emulsions, shampoos, foam aerosols can also be used as carriers.
  • Preferred carriers for direct dyes are setting agents, rinses and foaming aerosol preparations. The usual components of such carriers are water
  • Emulsifier in amounts of 1 - 20% by weight
  • - Solution brokers e.g. B. ethanol, isopropanol, 1,2-propylene glycol, glycerin, diethylene glycol monomethyl ether, butyl diglycol, polyethylene glycols in amounts of 1 - 10 wt .-%.
  • Thickeners in particular water-soluble polymers in amounts of 0.1-2% by weight
  • Preservatives e.g. B. p-hydroxybenzoic acid ester.
  • the direct dyes are better absorbed on the undamaged hair areas, in particular in the area of the hairline, while the excessive coloring of severely damaged hair sections, in particular the hair tips, is markedly reduced.
  • the following examples are intended to make this effect clear and to explain the subject matter of the invention in more detail without restricting it thereto.
  • Hair dyes according to the invention were produced in the form of aqueous solutions, each containing 1% by weight of the direct dye and 1% by weight of the leveling heterocyclic ring compounds, dissolved in water (Examples 1 and 3). For comparison, hair colorants were produced without the addition of the leveling agent (Examples 2 and 4). Finally, an aqueous solution of 1% by weight of a leveling agent (Example 5) and, separately, a 1% solution of a direct dye was prepared (Example 6).
  • the upper half of the strand of hair (the area of the hair tip) was treated with the aqueous solution of a cold waving agent based on ammonium thioglycolate for 30 minutes. After fixation (10 minutes, potassium bromate solution), the same half of the hair strand was ultrablonded with an aqueous solution of hydrogen peroxide and ammonium peroxide disulfate. Then treatment with the cold waving agent, fixation and ultrablonding was carried out again. The lower half of the hair strand (root area) was only ultrablonded once. In this way, two halves of hair strained to different degrees were obtained. The coloring solutions were left on the strands of hair at 27 ° C. for about 30 minutes, then washed out with a customary shampoo. After rinsing with water, the tresses were then dried.
  • Each strand of hair was measured at eight points (4 in the area of the hairline and 4 in the area of the hair tip) using a color measurement system from Datacolor.
  • the sample to be measured was fixed in a clamping device on the spectrophotometer and the reflectance values were measured over the range of visible light from 390 - 700 nm at a distance of 10 nm and processed by a computer (HP 2113 E mini computer).
  • the computer program determined the standard color values according to the CIE system (Commission Internationale de l'Eclairage) according to DIN 5033 and converted them into color difference numbers according to DIN 6174.
  • Example 5 The leveling agent solution of Example 5 was applied to a strand of hair of the type described above and pretreated in the same way, and after stripping off loosely attached solutions and drying the hair, the dyeing solution of Example 6 was applied (Examples 5 + 6). For comparison, a strand of hair without pretreatment with the leveling agent solution was only treated with the coloring solution of Example 6 (Example 6). The further tests were carried out as in Examples 1-4. 5. Results
  • AT's leveling agent heterocyclic ring compound
  • F1 1-hydroxy-2-amino-4,6-dinitrobenzene (picramic acid).
  • the dyeings obtained with dyeing solutions 1 and 3 according to the invention and by the two-stage process (5 + 6) according to the invention show significantly smaller color differences between damaged and undamaged hair areas than the dyeings obtained without the use of leveling agents (examples 2, 4 and 6) and no perceptible color differences .

Landscapes

  • 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)

Abstract

Un nouveau procédé de teinture des cheveux consiste à appliquer sur les cheveux, avant ou en même temps qu'on applique un colorant montant directement sur lesdits cheveux, une préparation contenant comme agent auxiliaire destiné à accroître l'uniformité de la montée du colorant, un composé à noyau hétérocyclique pentagonal ou hexagonal présentant dans le noyau un groupement des formules I-VI. Cet auxiliaire égalisant est utilisé avantageusement dans la préparation pour teinture de cheveux, en une quantité comprise entre 0,1 et 5 % en poids, conjointement avec 0,05 à 5 % en poids de colorant montant directement sur les cheveux et, éventuellement, avec des auxiliaires habituels.
PCT/EP1990/001420 1989-09-02 1990-08-24 Procede de teinture des cheveux au moyen de colorants directs WO1991003231A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1019920700440A KR927002998A (ko) 1989-09-02 1990-08-24 직접염료에 의한 모발 염색 방법
NO92920336A NO920336L (no) 1989-09-02 1992-01-24 Fremgangsmaate for haarfarving med direktfarvestoffer
FI920897A FI920897A0 (fi) 1989-09-02 1992-02-28 Foerfarande foer haorfaergning med direkthaorfaerger.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3929173A DE3929173A1 (de) 1989-09-02 1989-09-02 Verfahren zur haarfaerbung mit direktfarbstoffen
DEP3929173.1 1989-09-02

Publications (1)

Publication Number Publication Date
WO1991003231A1 true WO1991003231A1 (fr) 1991-03-21

Family

ID=6388496

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1990/001420 WO1991003231A1 (fr) 1989-09-02 1990-08-24 Procede de teinture des cheveux au moyen de colorants directs

Country Status (8)

Country Link
EP (1) EP0489775A1 (fr)
JP (1) JPH05500048A (fr)
KR (1) KR927002998A (fr)
CA (1) CA2066446A1 (fr)
DD (1) DD297324A5 (fr)
DE (1) DE3929173A1 (fr)
FI (1) FI920897A0 (fr)
WO (1) WO1991003231A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2855406B1 (fr) * 2003-06-02 2006-08-04 Oreal Nouveaux composes imidazoles et utilisation de ces composes pour la teinture de fibres keratiniques
US7238212B2 (en) 2003-06-02 2007-07-03 L'oreal, S.A. Imidazole compounds and use of these compounds for dyeing keratinous fibers
DE102006034533A1 (de) * 2006-07-24 2008-01-31 Beiersdorf Ag Kosmetische Zubereitungen zur Restrukturierung von Haaren mit besonderen Harnstoffderivaten
DE102006061555A1 (de) 2006-12-27 2008-07-03 Henkel Kgaa Synergistische Kombination von Seidenproteinen und ausgewählten Metallen
DE102007030099A1 (de) 2007-06-28 2009-01-02 Henkel Ag & Co. Kgaa Kosmetische Zusammensetzung enthaltend einen Champagner-Extrakt
DE102007031202A1 (de) 2007-07-04 2009-03-19 Henkel Ag & Co. Kgaa Hydrolysat aus Vikunja-Wolle und dessen Verwendung in kosmetischen Zubereitungen
DE102007033184A1 (de) 2007-07-13 2009-07-02 Henkel Ag & Co. Kgaa Haarpflegemittel enthaltend pulverisierte Edelsteine
DE102008034386A1 (de) 2007-11-23 2009-07-30 Henkel Ag & Co. Kgaa Proteinhydrolysate und deren Derivate sowie Mittel, enthaltend diese
DE102009009004A1 (de) 2008-02-18 2009-09-17 Seaquist Perfect Dispensing Gmbh Abgabevorrichtung mit einem kosmetischen Fluid
DE102008037633A1 (de) 2008-08-14 2010-02-18 Henkel Ag & Co. Kgaa Kosmetische Zusammensetzung enthaltend Öl aus den Früchten der Sumachgewächse
DE102008046178A1 (de) 2008-09-06 2010-03-11 Henkel Ag & Co. Kgaa Kosmetische Zusammensetzung enthaltend ein Öl aus den Früchten, insbesondere den Kernen von Pflanzen der Ordnung Rosales

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3009833A1 (de) * 1980-03-14 1981-10-01 Henkel Kgaa Verbessertes haarfaerbeverfahren mittels azo-entwicklungsfarbstoffen
GB2160900A (en) * 1984-06-20 1986-01-02 Oreal Dyeing composition for keratinous fibres containing at least one co-solubilised n-substituted 2-nitro-paraphenylenediamine and corresponding processes for dyeing keratinous fibres
EP0226860A1 (fr) * 1985-12-09 1987-07-01 Wella Aktiengesellschaft Procédé de mise en forme et de coloration simultanées de cheveux

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3009833A1 (de) * 1980-03-14 1981-10-01 Henkel Kgaa Verbessertes haarfaerbeverfahren mittels azo-entwicklungsfarbstoffen
GB2160900A (en) * 1984-06-20 1986-01-02 Oreal Dyeing composition for keratinous fibres containing at least one co-solubilised n-substituted 2-nitro-paraphenylenediamine and corresponding processes for dyeing keratinous fibres
EP0226860A1 (fr) * 1985-12-09 1987-07-01 Wella Aktiengesellschaft Procédé de mise en forme et de coloration simultanées de cheveux

Also Published As

Publication number Publication date
DE3929173A1 (de) 1991-03-07
CA2066446A1 (fr) 1991-03-03
EP0489775A1 (fr) 1992-06-17
KR927002998A (ko) 1992-12-17
DD297324A5 (de) 1992-01-09
FI920897A0 (fi) 1992-02-28
JPH05500048A (ja) 1993-01-14

Similar Documents

Publication Publication Date Title
EP0277996B1 (fr) Agent de teinture par oxydation des cheveux, son procede de fabrication et son utilisation
EP1062940B1 (fr) Composition d'agent pour permanente ayant un effet colorant et son procede de coloration des cheveux
EP0007537B1 (fr) Composition de teinture des cheveux
EP0226860B1 (fr) Procédé de mise en forme et de coloration simultanées de cheveux
DE3628398C2 (de) Mittel zum oxidativen Färben von Haaren, Verfahren zu seiner Herstellung und Verwendung des Mittels
EP0530229B1 (fr) Colorants d'oxydation pour fibres de keratine
DE29624635U1 (de) Aufhellende Zusammensetzung zum Färben von Keratinfasern, die einen speziellen Direktfarbstoff enthält
EP0655905B1 (fr) Glycosides d'alkyle dans des colorants
DE2617739C3 (de) Haarfärbemittel
DE69417204T3 (de) Oxydative Haarfärbungszusammensetzung von einem Paraphenylendiamin und einem Meta-aminophenol, und Verfahren zur Anwendung
WO1991003231A1 (fr) Procede de teinture des cheveux au moyen de colorants directs
CH658384A5 (de) Haarfaerbezusammensetzungen.
EP0491003B1 (fr) Colorant d'oxydation pour teinture de cheveux a effet egalisant
EP0727203A1 (fr) Colorant d'oxydation pour cheveux
WO1980000417A1 (fr) Preparation permettant la coloration des cheveux
EP0460127B1 (fr) Colorant capillaire sous forme de mousse
DE3545245A1 (de) Haarfaerbemittel mit direktziehenden azomethinfarbstoffen
EP0012965B1 (fr) Produit et procédé pour la teinture des cheveux
EP0881894B1 (fr) Agent de coloration de fibres keratiniques
EP0107834B1 (fr) Composition pour la teinture des cheveux
WO1998019660A1 (fr) Colorant s'utilisant dans la coloration de fibres keratiniques
DE1617713A1 (de) Verfahren zur Behandlung von lebenden menschlichen Haaren und Mittel zur Durchfuehrung desselben
DE3246747A1 (de) Haarfaerbemittel
DE3638227A1 (de) Haarfaerbemittel
DE3825163A1 (de) Verwendung von 2,6-dinitro-phenol-derivaten in haarfaerbemitteln

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA FI JP KR NO US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB IT LU NL SE

WWE Wipo information: entry into national phase

Ref document number: 1990912646

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 920897

Country of ref document: FI

WWE Wipo information: entry into national phase

Ref document number: 2066446

Country of ref document: CA

WWP Wipo information: published in national office

Ref document number: 1990912646

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1990912646

Country of ref document: EP