EP1732508A1 - Agent de coloration capillaire à base de colorants de cuve - Google Patents

Agent de coloration capillaire à base de colorants de cuve

Info

Publication number
EP1732508A1
EP1732508A1 EP04803242A EP04803242A EP1732508A1 EP 1732508 A1 EP1732508 A1 EP 1732508A1 EP 04803242 A EP04803242 A EP 04803242A EP 04803242 A EP04803242 A EP 04803242A EP 1732508 A1 EP1732508 A1 EP 1732508A1
Authority
EP
European Patent Office
Prior art keywords
vat
polyquaternium
amino
yellow
blue
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Withdrawn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
EP04803242A
Other languages
German (de)
English (en)
Inventor
Manuela Javet
Catherine MÜLLER
Anita Roulin
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 EP1732508A1 publication Critical patent/EP1732508A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • the present invention relates to an agent and method for dyeing hair, in particular human hair, with so-called vat dyes.
  • Vat dyes are widely used in the dyeing of cellulosic fiber materials; on the other hand, they are only used very rarely for animal fibers, such as wool or hair, since these do not survive the required very high pH of around 13 without drastic damage.
  • very aggressive reducing agents such as sodium dithionite (hydrosulfite) or sodium bisulfite, are usually used. For these reasons, vat dyeing has practically not been successful even with animal fibers.
  • vat dyes such as, for example, indanthrene dyes
  • indanthrene dyes can also be carried out under physiologically acceptable conditions if the pH is adjusted accordingly before the dyeing. In this way you get even hair colors with the greatest possible protection of the hair.
  • lightening is possible, with partial or complete decolorization of the natural hair pigment melanin during the final oxidation step.
  • the present application relates to an agent for dyeing hair, which is characterized in that it contains at least one vat dye which is reduced with a compound which forms an endiol in an alkaline medium and has a pH of 4 to 11.
  • Vat dyes for the purposes of the invention are understood to mean anthraquinone dyes and, if appropriate, non-pre-reduced sulfur dyes.
  • Examples of preferred dyes are Cl Vat Yellow 1 (Cl 70600), Cl Vat Yellow 2, Cl Vat Yellow 3, Cl Vat Yellow 4 (Cl 59100), Cl Vat Yellow 12 (Cl 65405), Cl Vat Yellow 13, Cl Vat Yellow 17 (Cl 65415), Cl Vat Yellow 20 (Cl 68420), Cl Vat Yellow 26, Cl Vat Yellow 28 (Cl 69000), Cl Vat Yellow 33,
  • Vat dyes can be found, among others, in the Color Index (C.l.), third parties
  • vat / sulfur dyes Sections of vat and sulfur dyes
  • vat dyes are used in a total amount of 0.01 to 10 percent by weight, preferably 0.1 to 2 percent by weight.
  • Compounds forming endiols are used as reducing agents in the alkaline medium, such as, for example, monohydroxyacetone, dihydroxyacetone, acetoin, glutaroin, adipoin, glycol aldehyde, benzoin, 2,3-dihydroxyacrylaldehyde and cycopentadiolone, with acetoin, monohydroxyacetone and dihydroxyacetone being particularly preferred.
  • Alkalizing agents for the reduction step are sodium or potassium hydroxide, or alkali salts of aromatic mono-hydroxy or polyhydroxy compounds, such as sodium or potassium phenolate or sodium or potassium cresolate.
  • the pH value for the reduction step is generally 10 to 13.
  • the reducing agents are used either in an equimolar amount or in an up to 50-fold molar excess, based on the vat dye, and a 3-to ⁇ -fold molar excess is particularly preferred.
  • organic solvents can be used in the reduction in a concentration of 0.1 to 80 percent by weight, preferably between 5 and 50 percent by weight.
  • the organic solvents should form a homogeneous phase with water.
  • organic solvents such as ethanol, n-propanol, isopropanol, n-butanol, glycols, such as, for example, ethylene glycol, propylene glycol, lactones, lactams, acid amides of lower carboxylic acids, ureas and sulfones are suitable and sulfoxides in question. Mixtures of these solvents can also be used.
  • cationic compounds preferably cationic polymers, such as, for example, polyquaternium-2, polyquaternium-4, polyquaternium-5, polyquatemiur ⁇ -6, polyquaternium-7, polyquaternium-10, Polyquaternium-11, polyquaternium-15, polyquaternium-16, polyquaternium-17, polyquaternium-18, polyquaternium-19, polyquaternium-20, polyquaternium-22, polyquaternium-24, polyquaternium-27, polyquaternium-28, polyquaternium-29, polyquaternium 31, polyquaternium-35, polyquaternium-36, polyquaternium-37, polyquaternium-39, polyquaternium-44, polyquaternium-46, polyquaternium-47, polyquaternium-51, polyquaternium-55, polyquatemium-57, quaternium-80, hydroxypropylguar hydroxypropyltrimethylammonium Guar hydroxypropyl
  • Polyquaternium-4 (hydroxyethylcellulose-dimethyldiallylammonium chloride copolymer), polyquaternium-7 (dimethyldiallylammonium chloride-acrylamide copolymer) and polyquaternium-22 (acrylic acid-diallyldimethylammonium chloride copolymer) are particularly preferred.
  • the cationic compounds are used in a total amount of 0.001 to 5 percent by weight, in particular 0.1 to 1 percent by weight.
  • ammonium ions for example in the form of aqueous ammonia or ammonium salts.
  • amines such as glucamines, aminomethyl propanol, monoethanolamine or triethanolamine
  • inorganic bases for example ammonium carbonate, ammonium hydrogen carbonate or ammonium carbonate, can be added.
  • the strongly alkaline pH of the color composition is adjusted to a physiologically tolerable value of 4 to 11, preferably 6 to 10.
  • Buffer systems or inorganic or organic acids for example lactic acid, citric acid, tartaric acid, glycolic acid, acetic acid, phosphoric acid, ammonium sulfate, ammonium chloride or cetyl lactate, can be used, for example, to set the desired pH.
  • oxidation dye precursors can also be added to the colorant according to the invention after the reduction step.
  • suitable oxidation dye precursors are the following developer substances and coupler substances and self-coupling compounds: (i) Developer substances: 1,4-diamino-benzene (p-phenylenediamine), 1,4-diamino-2-methyl-benzene (p -Toluenediamine), 1,4-diamino-2,6-dimethyl-benzene, 1,4-diamino-3,5-diethyl-benzene, 1,4-diamino-2,5-dimethyl-benzene, 1,4- Diamino-2,3-dimethyl-benzene, 2-chloro-1,4-diaminobenzene, 1,4-diamino-2- (thiophene-2-yl) benzene, 1,4-diamino-2- (thiophene-3- yl) benzene, 1,4-d
  • Coupler substances N- (3-dimethylaminophenyl) urea, 2,6-diamino-pyridine, 2-amino-4 - [(2-hydroxyethyl) amino] anisole, 2,4-diamino-1- fluoro-5-methyl-benzene, 2,4-diamino-1-methoxy-5-methyl-benzene, 2,4-diamino-1-ethoxy-5-methyl-benzene, 2,4-diamino-1- (2nd -hydroxy-ethoxy) -5-methyl-benzene, 2,4-di [(2-hydroxyethyl) amino] -1, 5-dimethoxy-benzene, 2,3-diamino-6-methoxy-pyridine, 3-amino- 6-methoxy-2- (methylamino) pyridine, 2,6-diamino-3,5-dimethoxy-pyridine, 3,5-diamino-2,6-dimethoxy-pyr
  • the total amount of the oxidation dye precursors contained in the agent according to the invention can be about 0.01 to 12 percent by weight, in particular about 0.2 to 6 percent by weight.
  • conventional natural and / or synthetic direct dyes for example so-called plant dyes such as henna, t ⁇ phenyl methane dyes, aromatic nitro dyes, azo dyes, quinone dyes, cationic or anionic dyes, can also be present in the colorant.
  • plant dyes such as henna, t ⁇ phenyl methane dyes, aromatic nitro dyes, azo dyes, quinone dyes, cationic or anionic dyes
  • Suitable synthetic dyes are: 1,4-bis [(2-hydroxyethyl) amino] -2-nitrobenzene, 1- (2-hydroxyethyl) amino-2-nitro-4- [di (2-hydroxyethyl) -amino] -benzene (HC Blue No. 2), 1 -amino-3-methyl-4 - [(2-hydroxyethyl) -amino] -6-nitrobenzene (HC Violet No. 1), 4- [ethyl- ( 2-hydroxyethyl) amino] -1 - [(2-hydroxyethyl) amino] -2-nitrobenzene hydrochloride (HC Blue No.
  • the total amount of direct dyes in the agent according to the invention can be about 0.01 to 7 percent by weight, preferably about 0.2 to 4 percent by weight.
  • antioxidants such as, for example, ascorbic acid, thioglycolic acid or sodium sulfite, and complexing agents for heavy metals, for example ethylenediaminetetraacetate or nitriloacetic acid, can be present in the agent according to the invention in an amount of up to about 0.5 percent by weight.
  • Perfume oils can be contained in the color carrier composition according to the invention in an amount of up to about 1 percent by weight.
  • the hair colorant described above can optionally further additives customary for hair colorants, such as thickeners, for example homopolymers of acrylic acid, vegetable gums, cellulose and starch derivatives, algal polyasaccharides, amphiphilic associative thickeners, and further preservatives;
  • Antioxidants for example sodium sulfite, thioglycolic acid or ascorbic acid; complexing; Solvents such as water, or, as already described, lower aliphatic alcohols, for example aliphatic alcohols having 1 to 4 carbon atoms such as ethanol, propanol and isopropanol, or glycols such as glycerol and 1,2-propylene glycol, or also sorbitol and wetting agents or emulsifiers, from the classes of anionic, cationic, amphoteric or nonionic surface-active substances and also plasticizers; Vaseline; Contain silicone oils, paraffin oil, polysorbates and fatty acids as well as care substances
  • the agent according to the invention is preferably packaged in the form of an aqueous or aqueous-alcoholic preparation, for example as a thickened solution, as an emulsion, as a cream, as an aerosol foam or as a gel.
  • the reduced colorant preparation should be stabilized in the reduced form as far as possible and protected against atmospheric oxygen. This can be achieved by suitable packaging, protective gas and the addition of protective and / or stabilizing substances or esterification (so-called leuco vat dye esters made with chlorosulfuric acid).
  • Protective or stabilizing compounds are, for example, cationic compounds, for example polymers, surfactants or metal ions such as zinc.
  • the coloring After an exposure time of about 1 to 60 minutes, preferably 5 to 30 minutes, at about 15 to 60 ° C., preferably 20 to 45 ° C., the coloring is “developed” oxidatively.
  • oxidizing agents for developing the coloring in particular hydrogen peroxide or its addition compounds to urea, melamine or sodium borate in the form of a 1 to 12 percent, preferably a 1.5 to 10 percent, aqueous solution into consideration.
  • the mixing ratio of colorant to oxidizing agent is dependent on the concentration of the oxidizing agent and is in Rule about 5: 1 to 1: 2, preferably 1: 1, the content of oxidizing agent in the resulting mixture of colorant and oxidizing agent preferably being about 0.5 to 8 percent by weight, in particular 1 to 4 percent by weight act until the dye is back in its insoluble pigment form (in R leeches about 2 to 5 minutes) and is wash-stable on the hair.
  • the exposure time of the oxidizing agent can be extended depending on the desired degree of lightening. If brightening of the natural pigment by more than two stages is desired, persulfates or mixtures of persulfates and hydrogen peroxide or their addition compounds can also be used. In this case, alkaline persulfate / peroxide preparations are preferably used.
  • the hair is rinsed with water and dried. If necessary, the hair can additionally with a Washed shampoo and, if necessary, rinsed with an acidic conditioner. The hair is then dried.
  • the above substances are mixed and left at 40 ° C for 20 minutes.
  • the pH is then adjusted to 9.9 with 2.5 g of lactic acid (90% aqueous solution).
  • 10 g of the mixture thus obtained are then applied to bleached natural hair.
  • the hair is then covered with a plastic hood or plastic wrap.
  • an additional 10 g of a 6% aqueous hydrogen peroxide emulsion are massaged in and left to act for 5 minutes.
  • the hair is then rinsed out with water, then rinsed with an acid conditioner and then dried.
  • the hair gets a uniform light yellow color.
  • the above substances are mixed and left at 40 ° C for 20 minutes.
  • the pH is then adjusted to 10.0 with 2.5 g of lactic acid (90% aqueous solution).
  • 10 g of the mixture thus obtained are then applied to bleached natural hair.
  • the hair is then covered with a plastic hood or plastic wrap.
  • an additional 10 g of a 6% aqueous hydrogen peroxide solution are massaged in and left to act for 5 minutes.
  • the hair is then rinsed out with water, then rinsed with an acid conditioner and then dried.
  • the above substances are mixed and left at 40 ° C for 20 minutes.
  • the pH is then adjusted to 10.0 with 2.5 g of lactic acid (90% aqueous solution).
  • 10 g of the mixture thus obtained are then applied to bleached natural hair.
  • the hair is then covered with a plastic hood or plastic wrap.
  • an additional 10 g of a 6% aqueous hydrogen peroxide solution are massaged in and left to act for 52 minutes.
  • the hair is then rinsed out with water, then rinsed with an acid conditioner and then dried.
  • the above substances are mixed and left at 40 ° C for 35 minutes.
  • the pH is then adjusted to 10.0 with 2.5 g of lactic acid (90% aqueous solution).
  • 10 g of the mixture thus obtained are then applied to bleached natural hair.
  • the hair is then covered with a plastic hood or plastic wrap.
  • an additional 10 g of a 6% aqueous hydrogen peroxide solution are massaged in and left to act for 5 minutes.
  • the hair is then rinsed out with water, then rinsed with an acid conditioner and then dried.
  • the hair gets an even green color.
  • the above substances are mixed and left at 40 ° C for 35 minutes.
  • the pH is then adjusted to 10.0 with 2.5 g of lactic acid (90% aqueous solution).
  • 10 g of the mixture thus obtained are then applied to bleached natural hair.
  • the hair is then covered with a plastic hood or plastic wrap.
  • an additional 10 g of a 6% aqueous hydrogen peroxide solution are massaged in and left to act for 5 minutes.
  • the hair is then rinsed out with water, then rinsed with an acid conditioner and then dried.
  • the above substances are mixed and left at 40 ° C for 20 minutes.
  • the pH is then adjusted to 9.8 with 2.5 g of ammonium sulfate in 10 g of water.
  • 10 g of the mixture thus obtained are then applied to bleached natural hair.
  • the hair is then covered with a plastic hood or plastic wrap.
  • an additional 10 g of a 6% aqueous hydrogen peroxide solution are massaged in and left to act for 2 minutes.
  • the hair is then rinsed out with water, then rinsed with an acid conditioner and then dried.
  • the above substances are mixed and left at 40 ° C for 20 minutes.
  • the pH is then adjusted to 9.8 with 2.5 g of lactic acid (90% aqueous solution).
  • 10 g of the mixture thus obtained are then applied to bleached natural hair.
  • the hair is then covered with a plastic hood or plastic wrap.
  • an additional 10 g of a 6% aqueous hydrogen peroxide solution are massaged in and left to act for 2 minutes.
  • the hair is then rinsed out with water, then rinsed with an acid conditioner and then dried.
  • the aforementioned substances are mixed and left to stand at 40 ° C. for 1.5 hours.
  • the pH is then adjusted to 9.8 with 2.5 g of 90% lactic acid.
  • 10 g of the mixture thus obtained are then applied to bleached natural hair.
  • the hair is then covered with a plastic hood or plastic wrap.
  • an additional 10 g of a 6% aqueous hydrogen peroxide solution are massaged in and left to act for 2 minutes.
  • the hair is then rinsed out with water, then rinsed with an acid conditioner and then dried.
  • the hair gets an even green color.
  • the above substances are mixed and left at 40 ° C for 20 minutes.
  • the pH is then adjusted to 10.0 with 2.5 g of lactic acid (90% aqueous solution).
  • 10 g of the mixture thus obtained are then applied to medium blonde natural hair.
  • the hair is then covered with a plastic hood or plastic wrap.
  • an additional 10 g of a 1: 2 mixture of a persulfate-containing bleaching powder and a 9% aqueous hydrogen peroxide solution are massaged in and left to act for 30 minutes.
  • the hair is then rinsed out with water, shampooed and then rinsed with an acid conditioner and then dried.
  • the hair gets an even, bright golden yellow color.

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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)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L’invention concerne un agent de coloration capillaire, contenant au moins un colorant de cuve réduit avec un composé formant un endiol en milieu alcalin et présentant un pH compris entre 4 et 11. L’invention concerne également une méthode de coloration capillaire faisant appel audit agent, à un pH physiologiquement tolérable, avec réoxydation subséquente dudit colorant de cuve.
EP04803242A 2004-03-26 2004-11-24 Agent de coloration capillaire à base de colorants de cuve Withdrawn EP1732508A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004014764A DE102004014764A1 (de) 2004-03-26 2004-03-26 Haarfärbemittel mit Küpenfarbstoffen
PCT/EP2004/013305 WO2005094762A1 (fr) 2004-03-26 2004-11-24 Agent de coloration capillaire à base de colorants de cuve

Publications (1)

Publication Number Publication Date
EP1732508A1 true EP1732508A1 (fr) 2006-12-20

Family

ID=34959630

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04803242A Withdrawn EP1732508A1 (fr) 2004-03-26 2004-11-24 Agent de coloration capillaire à base de colorants de cuve

Country Status (6)

Country Link
US (1) US20070180630A1 (fr)
EP (1) EP1732508A1 (fr)
JP (1) JP2007530463A (fr)
BR (1) BRPI0418672A (fr)
DE (1) DE102004014764A1 (fr)
WO (1) WO2005094762A1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007042286A1 (de) 2007-09-06 2009-03-12 Henkel Ag & Co. Kgaa Färbemittel mit Naturfarbstoffen und 1,3-Dihydroxyaceton
FR2949335B1 (fr) * 2009-09-02 2014-08-08 Oreal Procede de coloration consistant a appliquer un sel metallique et une composition comprenant un colorant hydrophobe et un compose particulier
FR2949333B1 (fr) * 2009-09-02 2013-01-04 Oreal Composition comprenant un colorant hydrophobe, une base minerale et un compose particulier (i), et son utilisation en coloration
ES2791032T3 (es) * 2009-09-02 2020-10-30 Oreal Composición que comprende un colorante hidrófobo, un agente alcalino orgánico y/o mineral particular, un compuesto particular (I) y un compuesto orgánico particular (II), y su utilización en coloración
FR2949334B1 (fr) * 2009-09-02 2015-10-23 Oreal Composition comprenant un colorant hydrophobe, un compose organique particulier i et un compose particulier ii, et utilisation en coloration
FR2949339B1 (fr) * 2009-09-02 2013-04-19 Oreal Composition comprenant un colorant hydrophobe, un agent alcalin organique et un compose particulier (i), et son utilisation en coloration
CN101935467B (zh) * 2010-08-27 2013-04-24 江苏亚邦染料股份有限公司 一种工装用高耐氯漂高耐热压牢度的黑色还原染料
CN101935468B (zh) * 2010-08-27 2013-03-27 江苏亚邦染料股份有限公司 一种工装用高耐氯漂牢度的藏青色还原染料
CN101942221B (zh) * 2010-08-27 2013-04-24 江苏亚邦染料股份有限公司 一种工装用高耐热压牢度的浅灰色还原染料
CN101942222B (zh) * 2010-08-27 2013-04-24 江苏亚邦染料股份有限公司 一种工装用高耐氯漂牢度的灰色还原染料
CN101942219B (zh) * 2010-08-27 2013-04-24 江苏亚邦染料股份有限公司 一种工装用高耐氯漂高耐热压牢度的深蓝色还原染料
CN102660131A (zh) * 2012-04-19 2012-09-12 徐州开达精细化工有限公司 还原黄3rt的生产方法
CN104277486A (zh) * 2014-09-15 2015-01-14 萧县凯奇化工科技有限公司 还原黄3rr的合成方法
US11904042B2 (en) * 2018-07-06 2024-02-20 HFC Prestige International Holding Switzerland S.a.r.l. Hair coloring composition and methods for its application and removal
EP4196084A2 (fr) 2020-08-12 2023-06-21 Wella Germany GmbH Procédé et composition pour colorer un substrat kératinique à l'aide de colorants de cuve solubilisés
WO2023152322A1 (fr) 2022-02-10 2023-08-17 Wella Germany Gmbh Coloration capillaire mettant en œuvre des précurseurs de colorant oxydatif comprenant des couleurs primaires à base de pyrazole et des coupleurs, en combinaison avec des colorants de cuve solubilisés, pour améliorer la résistance des couleurs au lavage

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Also Published As

Publication number Publication date
JP2007530463A (ja) 2007-11-01
WO2005094762A1 (fr) 2005-10-13
BRPI0418672A (pt) 2007-06-05
DE102004014764A1 (de) 2005-10-06
US20070180630A1 (en) 2007-08-09

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