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WO1996022077A1 - Arylcetones pour colorer des fibres contenant de la keratine - Google Patents

Arylcetones pour colorer des fibres contenant de la keratine Download PDF

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Publication number
WO1996022077A1
WO1996022077A1 PCT/EP1996/000062 EP9600062W WO9622077A1 WO 1996022077 A1 WO1996022077 A1 WO 1996022077A1 EP 9600062 W EP9600062 W EP 9600062W WO 9622077 A1 WO9622077 A1 WO 9622077A1
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WO
WIPO (PCT)
Prior art keywords
groups
amino
formula
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.)
Ceased
Application number
PCT/EP1996/000062
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German (de)
English (en)
Inventor
Hinrich Möller
Horst Höffkes
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1996022077A1 publication Critical patent/WO1996022077A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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 invention relates to the use of certain aryl ketones for dyeing keratin-containing fibers, in particular human hair.
  • keratin fibers e.g. B. hair, wool or furs
  • direct dyes or oxidation dyes which are formed by oxidative coupling of one or more developer components with each other or with one or more coupler components
  • oxidation dyes intensive dyeings with good fastness properties can be achieved, but the development of the color takes place under the influence of oxidizing agents such as. B. H2Ü2, which often results in damage to the fiber.
  • Direct dyes are applied under gentler conditions, but their disadvantage is that the dyeings often have inadequate fastness properties.
  • keratin fibers e.g. Wool, furs, skins and human hair are considered.
  • the aryl ketones described below can also be used to dye other natural fibers, e.g. Cotton, jute, sisal, linen or silk, modified natural fibers, e.g. Regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as e.g. Polyamide, polyacrylonitrile, polyurethane and polyester fibers can be used.
  • the invention relates to the use of aryl ketones of the formula I
  • R represents a C 1 -C 4 -alkyl group or an aryl group and R * also a C 1 -C 4 -alkylene group which is connected to the aromatic radical of the formula I or an N, S or O-containing isoelectronic group , optionally benzo-fused
  • R ⁇ , R and R 4 independently of one another for hydrogen, halogen atoms, hydroxy groups, -C-C _ ⁇ - alkoxy groups, -C-C4-alkyl groups, C2 ⁇ C4-hydroxyalkyl groups, amino (-C-C4) alkyl groups, -C-C4-alkoxy- (C ⁇ -C.4) - alkyl groups, nitro, carboxy or sulfo groups or groups NR5R6, where R5 and R & C ⁇ -C4 ⁇ alkyl groups or C2 ⁇ C4- Hydroxyalkyl groups mean and together with the N atom can also represent a 5-, 6- or 7-membere
  • aryl ketones or their ketals to be used according to the invention are: acetophenone, propiophenone, 2-, 3-, 4-hydroxyacetophenone, -propiophenone, -butyrophenone, 2,4-, 2,5-, 2,6-dihydroxyacetophenone , 2,3,4-, 3,4,5-, 2,4,5-trihydroxy, 2,4,6-, 3,4,5-trimethoxy-acetophenone, 3,4,5-trimethoxy-acetophenone diethyl ketal, 4-hydroxy-3-methoxy, 3,5-dimethoxy-4-hydroxy, 4-amino, 4-dimethylamino, 4-morpholino, 4-piperidino, 4-imidazolino, 2-hydroxy-5-bromo, 4-hydroxy-3-nitroacetophenone, acetophenone-2-, -4-carboxylic acid, benzophenone, 4-hydroxy, 2-amino, 4,4'-, 2,4-dihy - Hydroxy-, 2,4,4'--hydroxy
  • Acetophenone, 2-hydroxyacetophenone, 4-hydroxyacetophenone, 2,4-dihydroxyacetophenone, 2,5-dihydroxyacetophenone, 2,6-dihydroxyacetophenone, 2,4,6-trihydroxyacetophenone, 2,3,4-trihydroxyacetophenone and quercetin are preferably used and (+) - usnic acid.
  • the aryl ketones of formula I alone only weakly stain keratin fibers. Brilliant colorations in the orange, brown, red-brown, blue-black and black range with good fastness properties (fastness to light, fastness to washing, fastness to rubbing) are achieved if the aryl ketones of the formula I together with compounds having a primary or secondary amino group, for example aniline derivatives , with a nitrogen-containing heterocytic compound, eg primary heteroaro a- table amines, or an aromatic hydroxy compound can be used. On the one hand, these are compounds which also only weakly dye hair on their own and only give brilliant colorations together with the aryl ketones of the formula I.
  • Suitable compounds with a primary or secondary amino group are, for example, primary aromatic amines such as 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, o-, m-, p-phenylene diamine, 2,5-diaminotoluene, phenol, anisole, phenethole, 2-chloro-p-phenylene diamine, 4-methylamino, 3-, 4-dimethylamino , 3,4-methylene-dioxyaniline, 3-amino-2,4-dichloro, 4-methylamino, 2-methyl-5-amino, 3-methyl
  • Suitable nitrogen-containing heterocycles are e.g. 2-, 3-, 4-amino, 2-amino-3-hydroxy, 2,6-diamino, 2,5-diamino, 2,3-diamino, 2-dimethylamino-5-amino -, 3-amino-2-methylamino-6-methoxy-, 2,3-diamino-6-methoxy-, 3,5-diamino-2,5-dimethoxy-, 2,4,5-triamino-, 2,6-di-hydroxy-3,4-dimethylpyridine, 4,5,6-triamino-, 4-hydroxy-2,5,6-tri-amino-, 2,4,5,6-tetraamino-, 2nd -Methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-amino-4-methoxy-6-methyl-pyrimidine, 3,5-diamino-pyrazole, -1.2
  • Suitable aromatic hydroxy compounds are, for example, 2-, 4-, 5-methylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2-, 3-, 4-methoxy-, 3-dimethylamino-, 2 - (2-hydroxyethyl) -, 3,4-methylenedioxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, -phenylacetic acid, gallic acid, 2,4,6-trihydroxybenzoic acid, -acetophenone, 2-, 4-methyl-, 2-, 4-chlororesorcinol, 1-, 2-naphthol, 1 , 5-, 2,3-, 2,7-dihydroxynaphthalene, 6-dimethylamino-4-hydroxy-2-naphthalenesulfonic acid, 3,6-dihydroxy-2,7-naphthalenesulfonic acid.
  • Amino acids or oligopeptides composed of 2 to 9 amino acids are also suitable. All naturally occurring and synthetic amino acids are suitable as amino acids, e.g. which 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. Suitable 01igopeptides are all oligopeptides made up of naturally occurring and synthetic amino acids.
  • 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 are e.g. Glutathione or the oligopeptides contained in the hydrolyzates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein.
  • aryl ketones of the formula I can also be used together in all colorants; Likewise, several different components from the groups of compounds having a primary or secondary amino group, nitrogen-containing heterocycles, aromatic hydroxy compounds or amino acids can also be used together.
  • the colorants produce intensive colorations even at physiologically tolerable temperatures of below 45 ° C. They are therefore particularly suitable for dyeing human hair.
  • the colorants can be incorporated into a water-containing cosmetic carrier. Suitable water-containing cosmetic carriers are, for example, creams, emulsions, gels or also surfactant-containing foaming solutions such as shampoos or other preparations which are suitable for use on the hair.
  • the water-containing cosmetic carrier usually contains wetting and emulsifying agents such as anionic, nonionic or apholytic surfactants, for example fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products with fatty alcohols, with fatty acids, with sorbitan fatty acids, with sorbitan fatty acids, with alkyl phenols Fatty acid partial glycerides and fatty acid alkanolamides; Thickeners, e.g. B.
  • anionic, nonionic or apholytic surfactants for example fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products with fatty alcohols, with fatty acids, with
  • fatty alcohols fatty acids, paraffin oils, fatty acid esters and other fat components in emulsified form; water-soluble polymeric thickeners such as natural gums, e.g. B. gum arabic, karaya gum, guar gum, locust bean gum, linseed gums and pectin, biosynthetic gums, such as xanthan gum and Dextra ⁇ e, synthetic gums, z.
  • bentonite or fully synthetic hydrocolloids such as polyvinyl alcohol or polyvinylpyrrolidone
  • hair care additives such as water-soluble cationic polymers, anionic polymers, nonionic polymers, amphoteric or zwitterionic polymers, pantothenic acid, vitamins, plant extracts or cholesterol, pH adjusting agents, complexing agents and perfume oil Reducing agents to stabilize the ingredients, e.g. B. ascorbic acid, finally can also contain dyes for coloring the cosmetic preparations.
  • solubilizers such as ethylene, 1,3-propylene, 1,2-propylene, 1,2-butylene glycol, glycerol, ethanol, tert. Butanol, 2-propanol or phenethol in amounts of 2-50% may be useful.
  • water-free carriers are also suitable if the substrate to be colored is moistened with water.
  • Suitable water-free carriers are e.g. Oils combined with anhydrous emulsifiers such as paraffin oils or silicone oils of low to medium viscosity.
  • the aryl ketones of the formula I and the compounds having a primary or secondary amino group, the amino acids or oligopeptides composed of 2 to 9 amino acids, the nitrogen-containing heterocycles or the aromatic hydroxy compounds are in each case in an amount of 0.3 to 65, preferably 6 to 20 mmol, based in each case on 100 g of the total colorant.
  • Suitable metal salts are, for example, the formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of potassium, sodium, lithium, magnesium, calcium , Strontiums, bariums, manganese, iron, cobalt, copper, zinc; sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate are preferred, which in the given case are present in an amount of 0.3 to 65, preferably 6 to 20 mmol, based on 100 g of the total colorant, are contained.
  • the pH of the ready-to-use coloring preparations is between 2 and 11, preferably
  • the colorants are applied to the hair in the form of the water-containing, or else the water-free, cosmetic carrier in an amount of 50-100 g, left there for about 30 minutes and then rinsed out or washed out with a commercially available hair shampoo.
  • the two reactive components can either be applied to the hair at the same time or else one after the other, regardless of which of the two components is applied first; the ammonium or metal salts can be added to the first or second component. There may be a time interval of up to 30 minutes between the application of the first and the second component. Pretreatment of the hair with the saline solution is also possible.
  • the two reactive components can be stored together and separately either without water or already in the finished formulation. When stored separately, the reactive components are only intimately mixed with one another immediately before use.
  • the water-free storage can take place either in powder form or in water-free gels or dispersions. When stored as a powder, a defined amount of 50-80 ° C warm water is added to the mixture and a homogeneous mixture is produced. If an anhydrous gel is used, it can be mixed with water or applied directly to damp hair.
  • a slurry of 10 mmoles of an aryl ketone of formula I and 10 mmoles of a reactant, 10 mmoles of sodium acetate and a drop of a 20% fatty alkyl ether sulfate solution in 100 ml of water was prepared.
  • the slurry was etched to boiling temperature and filtered after cooling, the pH was then adjusted to 6.
  • the color depth was rated on the following scale:

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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)
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Abstract

L'invention concerne l'utilisation d'arylcétones de la formule (I) ainsi que de leurs cétals pour colorer des fibres contenant de la kératine, notamment des cheveux naturels. Dans ladite formule (I), R1 désigne un groupe alkyle C¿1?-C4 ou un groupe aryle et R?1¿ peut également désigner un groupe alkylène C¿1?-C4 lié au reste aromatique de la formule (I) ou un groupe isoélectronique contenant N, S ou O, éventuellement annelé en benzène, et R?2, R3 et R4¿ désignent, indépendamment les uns des autres, des hydrogènes, des atomes d'halogène, des groupes hydroxy, des groupes alcoxy C¿1?-C4, des groupes alkyle C1-C4, des groupes hydroxyalkyle C2-C4, des groupes amino-alkyle (C1-C4), des groupes alcoxy C1-C4-alkyle (C1-C4), des groupes nitro, des groupes carboxy ou des groupes sulfonés ou des groupes NR?5R6, R5 et R6¿ étant des groupes alkyle C¿1?-C4 ou des groupes hydroxyalkyle C2-C4, et peuvent également représenter un composé cyclique à 5, 6 ou 7 chaînons, conjointement avec l'atome de N, ou le système aromatique représente un reste acide usnique.
PCT/EP1996/000062 1995-01-18 1996-01-09 Arylcetones pour colorer des fibres contenant de la keratine Ceased WO1996022077A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19501303.4 1995-01-18
DE1995101303 DE19501303A1 (de) 1995-01-18 1995-01-18 Arylketone zum Färben keratinhaltiger Fasern

Publications (1)

Publication Number Publication Date
WO1996022077A1 true WO1996022077A1 (fr) 1996-07-25

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DE (1) DE19501303A1 (fr)
WO (1) WO1996022077A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000015183A1 (fr) * 1998-09-15 2000-03-23 Henkel Kommanditgesellschaft Auf Aktien Produit de coloration de fibres contenant de la keratine
US7179912B2 (en) 2000-09-01 2007-02-20 Icos Corporation Materials and methods to potentiate cancer treatment
US8404681B2 (en) 2003-03-24 2013-03-26 Luitpold Pharmaceuticals, Inc. Xanthones, thioxanthones and acridinones as DNA-PK inhibitors

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6291442B1 (en) 1998-02-03 2001-09-18 The General Hospital Corporation Pharmacological modulators of voltage-gated potassium ion channels
EP2072083B1 (fr) 2007-12-19 2012-02-15 Symrise AG Utilisation de 2,4'-diméthyl-propiophénone en tant que parfum

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1492196A1 (de) * 1964-09-02 1969-12-04 Therachemie Chem Therapeut Verfahren und Mittel zur Erleichterung des Anfaerbens von Haaren mit kationaktiven direktziehenden Farbstoffen
DE1492195A1 (de) * 1964-09-02 1969-12-04 Therachemie Chem Therapeut Verfahren und Mittel zur Erleichterung des Anfaerbens von Haaren mit anionaktiven direktziehenden Farbstoffen
DE2717041A1 (de) * 1977-04-18 1978-10-26 Henkel Kgaa Haarfaerbemittel
FR2400359A1 (fr) * 1977-08-19 1979-03-16 Oreal Compositions tinctoriales a base de colorants directs contenant un acide (2,5-dihydroxyphenyl) carboxylique ou l'un de ses sels
FR2543434A1 (fr) * 1983-04-01 1984-10-05 Muller International Sarl Alba Composition et procede pour la teinture du systeme pileux.
EP0335403A2 (fr) * 1988-03-30 1989-10-04 Sansho Seiyaku Co., Ltd. Composition pour la teinture des cheveux
JPH02138114A (ja) * 1988-11-18 1990-05-28 Kashiwa Kagaku Kogyo:Kk 染毛剤
EP0498707A1 (fr) * 1991-02-04 1992-08-12 L'oreal Procédé de teinture des fibres kératiniques avec un mono- ou dihydroxyindole et un dérivé carbonylé aromatique non-oxydant et agent de teinture
WO1993009758A1 (fr) * 1991-11-18 1993-05-27 Henkel Kommanditgesellschaft Auf Aktien Agents de coloration des cheveux

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1492196A1 (de) * 1964-09-02 1969-12-04 Therachemie Chem Therapeut Verfahren und Mittel zur Erleichterung des Anfaerbens von Haaren mit kationaktiven direktziehenden Farbstoffen
DE1492195A1 (de) * 1964-09-02 1969-12-04 Therachemie Chem Therapeut Verfahren und Mittel zur Erleichterung des Anfaerbens von Haaren mit anionaktiven direktziehenden Farbstoffen
DE2717041A1 (de) * 1977-04-18 1978-10-26 Henkel Kgaa Haarfaerbemittel
FR2400359A1 (fr) * 1977-08-19 1979-03-16 Oreal Compositions tinctoriales a base de colorants directs contenant un acide (2,5-dihydroxyphenyl) carboxylique ou l'un de ses sels
FR2543434A1 (fr) * 1983-04-01 1984-10-05 Muller International Sarl Alba Composition et procede pour la teinture du systeme pileux.
EP0335403A2 (fr) * 1988-03-30 1989-10-04 Sansho Seiyaku Co., Ltd. Composition pour la teinture des cheveux
JPH02138114A (ja) * 1988-11-18 1990-05-28 Kashiwa Kagaku Kogyo:Kk 染毛剤
EP0498707A1 (fr) * 1991-02-04 1992-08-12 L'oreal Procédé de teinture des fibres kératiniques avec un mono- ou dihydroxyindole et un dérivé carbonylé aromatique non-oxydant et agent de teinture
WO1993009758A1 (fr) * 1991-11-18 1993-05-27 Henkel Kommanditgesellschaft Auf Aktien Agents de coloration des cheveux

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 9027, Derwent World Patents Index; AN 90-206310, XP002003555 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000015183A1 (fr) * 1998-09-15 2000-03-23 Henkel Kommanditgesellschaft Auf Aktien Produit de coloration de fibres contenant de la keratine
US7179912B2 (en) 2000-09-01 2007-02-20 Icos Corporation Materials and methods to potentiate cancer treatment
US8242115B2 (en) 2000-09-01 2012-08-14 Luitpold Pharmaceuticals, Inc. Materials and methods to potentiate cancer treatment
US8404681B2 (en) 2003-03-24 2013-03-26 Luitpold Pharmaceuticals, Inc. Xanthones, thioxanthones and acridinones as DNA-PK inhibitors

Also Published As

Publication number Publication date
DE19501303A1 (de) 1996-07-25

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