EP1879547A1 - Färbemittel mit einem farbstoff und einem propylenglykolderivat - Google Patents

Färbemittel mit einem farbstoff und einem propylenglykolderivat

Info

Publication number
EP1879547A1
EP1879547A1 EP06755457A EP06755457A EP1879547A1 EP 1879547 A1 EP1879547 A1 EP 1879547A1 EP 06755457 A EP06755457 A EP 06755457A EP 06755457 A EP06755457 A EP 06755457A EP 1879547 A1 EP1879547 A1 EP 1879547A1
Authority
EP
European Patent Office
Prior art keywords
composition
composition according
propylene glycol
amino
para
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Withdrawn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
EP06755457A
Other languages
English (en)
French (fr)
Inventor
Maxime De Boni
Alain Lagrange
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.)
LOreal SA
Original Assignee
LOreal SA
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 LOreal SA filed Critical LOreal SA
Publication of EP1879547A1 publication Critical patent/EP1879547A1/de
Withdrawn legal-status Critical Current

Links

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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • 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

Definitions

  • the subject of the invention is a dyeing composition
  • a dyeing composition comprising, in a medium suitable for dyeing keratinous fibers, at least one dyestuff and a propylene glycol derivative, and also the method for dyeing keratinous fibers, in particular keratinous fibers. from this composition.
  • dyeing compositions containing direct dyes.
  • the standard dyes which are used are in particular nitrobenzene, anthraquinone, nitropyridine, azo, azo, xanthene, acridine, azine, triarylmethane or natural dyes. These dyes may be nonionic, anionic, cationic or amphoteric.
  • These dyes which are colored and coloring molecules having an affinity for keratinous fibers, are applied for the time necessary to obtain the desired coloration, and then rinsed.
  • the colorations that result are particularly chromatic colorations that are however temporary or semi-permanent because the nature of the interactions that bind the direct dyes to the keratinous fiber, and their desorption of the surface and / or the core of the fiber are responsible for their low dyeing power and their poor resistance to washes or perspiration.
  • stain keratin fibers permanently by oxidation dyeing. This staining technique consists in applying to the keratinous fibers a composition containing dye precursors such as oxidation bases and couplers. These precursors under the action of an oxidizing agent will form in the hair one or more colored species.
  • a coloring composition comprising, in a suitable medium, at least one dyestuff chosen from direct dyes and dye precursors, the appropriate medium containing water and at least one a propylene glycol derivative of formula (I) below R 1 (OC 3 He) n OR 2 in which R 1 represents hydrogen, a C 1 -C 6 alkyl radical or C 2 -C 6 acyl radical, R 2 represents a C 2 -C 6 alkyl or C 6 -C 30 aryl radical and n varying from 1 to 6, the OC 3 H 6 unit possibly being linear or branched.
  • a second subject of the present invention relates to a process for dyeing keratinous fibers, in particular human keratin fibers from the composition of the invention.
  • a final subject of the invention is a dyeing kit comprising on the one hand a composition comprising a dyestuff as defined above and a propylene glycol derivative of formula (I) and, on the other hand, a composition containing an oxidizing agent.
  • the direct dyes useful in the composition of the invention are dyes soluble in water or in a solvent medium.
  • direct dyestuff mention may be made of neutral, acidic or cationic nitro-benzene direct dyes, acid or cationic neutral azo direct dyes, quinone and, in particular, neutral, acidic or cationic neutral quinone dyes, azine direct dyes, dyes direct triarylmethanics, direct indoamine dyes and natural direct dyes.
  • EP-714954 FR 2822696, FR 2825702, FR 2825625, FR 2822698, FR 2822693, FR
  • quinone direct dyes mention may be made of the following dyes: - Disperse Red 15, -Solvent Violet 13, -Acid Violet 43, Disperse Violet 1, Disperse
  • azine dyes mention may be made of the following compounds: Basic Blue 17, Basic Red 2.
  • triarylmethane dyes mention may be made of the following compounds:
  • direct dyes mention may also be made of natural direct dyes such as lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogalline, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidine. It is also possible to use the extracts or decoctions containing these natural dyes, and in particular poultices or extracts made from henna.
  • natural direct dyes such as lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogalline, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidine.
  • extracts or decoctions containing these natural dyes and in particular poultices or extracts made from henna.
  • the direct dye (s) present in the composition of the invention may be present in an amount generally comprised between 0.001 and 20% by weight of the total weight of the composition and preferably from 0.001 to 5% by weight approximately.
  • the dye precursors useful in the present invention are, for example, the oxidation bases and the couplers conventionally used for oxidation dyeing.
  • the oxidation bases may be chosen from para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, bis-para-aminophenols, ortho-aminophenols, heterocyclic bases and their salts. addition.
  • para-phenylenediamines mention may be made of para-phenylenediamine, para-toluenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-dimethylphenylenediamine and diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N, N-dimethyl-para-phenylenediamine, N, N-diethyl-para-phenylenediamine, N, N-dipropyl-para-phenylenediamine, 4-amino-N- 1- N diethyl 3-methylaniline, N, N-bis- ( ⁇ -hydroxyethyl) para-phenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino-2-methylaniline, 4 N, N bis ( ⁇ hydroxyeth
  • para-phenylenediamine para-toluenediamine, 2-isopropyl para-phenylenediamine, 2- ⁇ -hydroxyethyl para-phenylenediamine, 2 ⁇ -hydroxyethyloxy para-phenylenediamine, 2,6 dimethyl para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N, N bis- ( ⁇ -hydroxyethyl) para-phenylenediamine, 2-chloro-para-phenylenediamine, 2-acetylaminoethyloxy para-phenylenediamine, and their addition salts with an acid are particularly preferred.
  • N 1 N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) 1,3 diamino propanol, N may be mentioned by way of example, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylenediamine, N 1 N 'bis (4-aminophenyl) tetramethylenediamine, N 1 N' bis ( ⁇ hydroxyethyl) N , N'-bis- (4- aminophenyl) tetramethylenediamine, N 1 N 1 bis- (4-methyl-aminophenyl) tetramethylenediamine, N, N'-bis- (ethyl) N 1 N 1 bis (4'-amino-3'-methylphenyl) ethylenediamine, 1 , 8-bis- (2,5-diamino phenoxy) -3
  • para-aminophenol para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluoro-phenol, 4-amino-3-hydroxymethylphenol, 4-amino-2- are exemplified.
  • methyl phenol 4-amino-2-hydroxymethyl-phenol, 4-amino-2-methoxymethyl-phenol, 4-amino-2-aminomethyl-phenol, 4-amino-2- ( ⁇ -hydroxyethylaminomethyl) phenol, 4-amino-2-fluoro phenol, and their addition salts with an acid.
  • ortho-aminophenols mention may be made, for example, of 2-amino phenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-amino-phenol, and their salts. addition with an acid.
  • heterocyclic bases that may be mentioned by way of example are pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives mention may be made of the compounds described for example in patents GB 1 026 978 and GB 1 153 196, such as 2,5 diamino pyridine, 2- (4-methoxyphenyl) amino 3 amino pyridine, 2, 3 diamino 6-methoxy pyridine, 2- ( ⁇ -methoxyethyl) amino-3-amino-6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid.
  • pyridinic oxidation bases useful in the present invention are the 3-amino pyrazolo [1, 5a] -pyridines oxidation bases or their addition salts described, for example, in patent application FR 2801308.
  • pyrimidine derivatives mention may be made of the compounds described, for example, in DE 2359399; JP 88 169571; JP 05-63124; EP 0770375 or patent application WO 96/15765 such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2,4 dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR A 2750048 and among which mention may be made of pyrazolo [1,5-a] -pyrimidine -3,7-diamine; 2,5-dimethyl pyrazolo [1,5a] -pyrimidine-3,7-diamine; pyrazolo [1,5-a] pyrimidine-3,5-diamine; 2,7-dimethyl pyrazolo [1,
  • pyrazole derivatives mention may be made of the compounds described in DE 3843892, DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 as the 4.5 diamino 1-methyl pyrazole, 4,5-diamino 1- ( ⁇ -hydroxyethyl) pyrazole, 3,4 diamino pyrazole, 4,5-diamino 1 (4 'chlorobenzyl) pyrazole, 4,5-diamino 1, 3-dimethyl pyrazole, 4,5-diamino-3-methyl-1-phenyl pyrazole, 4,5-diamino-1-methyl-3-phenyl pyrazole, 4-amino-1,3-dimethyl-5-hydrazino pyrazole, 1-benzyl-4 5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl
  • the oxidation base (s) present in the composition of the invention are in general each present in an amount of between 0.001 to 10% by weight approximately of the total weight of the dyeing composition, preferably between 0.005 and 6%.
  • the couplers useful in the composition of the invention are, for example, meta-phenylenediamine couplers, meta-aminophenol couplers, meta-diphenol couplers, naphthalenic couplers, heterocyclic couplers and their addition salts.
  • the coupler or couplers are each generally present in an amount of between 0.001 and 10% by weight of the total weight of the dye composition, preferably between 0.005 and 6%.
  • composition of the invention can of course comprise in combination direct dyes, oxidation bases and couplers.
  • alkyl radical is intended to mean linear or branched radicals such as the methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, pentyl and hexyl radicals. .
  • aryl radical there may be mentioned phenyl radicals, benzyl.
  • the pattern OC 3 H 6 represents e.g. OCH 2 CH 2 CH 2, OCH 2 CH (CH 3) or OCH (CH 3) CH 2.
  • propylene glycol derivatives of formula (I) mention may be made of the following propylene glycols:
  • the propylene glycol derivative of formula (I) is such that n is between 2 and 4 inclusive and R 2 represents an ethyl, propyl, butyl, linear or branched radical.
  • composition of the invention generally comprises a quantity of propylene glycol derivative of formula I comprised between 0.1 and 80%, preferably between 0.5 and 50% and even more preferably between 1 and 30% of the total weight of the composition.
  • the amount of water is at least 40% based on the total weight of the coloring composition. Even more preferentially, this amount of water is at least 70%.
  • the medium suitable for dyeing keratinous fibers comprises at least 70% water by weight relative to the total weight of the composition. It may for example consist solely of water or a mixture of water and at least one organic solvent other than the propylene glycol derivative of formula (I).
  • organic solvent there may be mentioned for example lower alkanols C 1 -C 4 , such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, diethylene glycol monoethyl ether and monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the staining medium is a suitable cosmetic medium.
  • the total amount of solvent including the propylene glycol derivative (s) of formula (I) can vary between approximately 0.1 and 80% by weight relative to the total weight of the composition, and more preferably between 0.5 and 50% by weight approximately and even more preferably between 1 and 30% of the total weight of the composition.
  • the dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, or mixtures thereof, anionic polymers, cationic, nonionic, amphoteric, zwitterionic or their mixtures, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, volatile or non-volatile silicones, modified or non-modified, film-forming agents and in particular nonionic, cationic, anionic, amphoteric fixing polymers, ceramides, preservatives, opacifying agents.
  • adjuvants conventionally used in compositions for dyeing hair such as anionic, cationic, nonionic, amphoteric or z
  • the adjuvants above are generally present in an amount for each of them between 0.01 and 20% by weight relative to the weight of the composition.
  • the pH of the dyeing composition according to the invention is generally between 2 and 12 approximately.
  • the pH is preferably between 8 and 12.
  • acidifying agents mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids.
  • mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids.
  • alkalinizing agents there may be mentioned, for example, ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, the hydroxides of sodium or potassium and the compounds of formula (III) below:
  • W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 4 alkyl radical;
  • the dye composition according to the invention may be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratinous fibers, and especially human hair.
  • the subject of the invention is also a method for dyeing keratin fibers which comprises applying the composition of the invention as defined above to the keratinous fibers for a time sufficient to obtain the desired coloration.
  • the keratinous fibers are then rinsed.
  • the exposure time is generally between about 1 to 60 minutes, preferably about 5 to 60 minutes.
  • composition of the invention may further comprise an oxidizing agent.
  • an oxidizing agent When the composition of the invention contains only direct dyes, this oxidizing agent makes it possible to obtain a lightening coloration, that is to say a simultaneous discoloration and coloration of the hair.
  • the dye composition comprises an oxidation base and / or a coupler
  • an oxidizing agent may then contain an oxidizing agent.
  • the oxidizing agents conventionally used for the oxidation dyeing of keratinous fibers are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and oxidase enzymes. among which there may be mentioned peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred.
  • the oxidizing agent can be added to the composition of the invention just at the time of use or it can be implemented from an oxidizing composition containing it, this composition being applied simultaneously or sequentially to the composition of the composition. 'invention.
  • the oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing hair and as defined above.
  • the pH of the oxidizing composition containing the oxidizing agent is such that, after mixing with the dyeing composition, the pH of the resulting composition applied to the keratinous fibers preferably varies between 3 and 12 approximately, and even more preferably between 5 and 11. It can be adjusted to the desired value by means of acidifying or basifying agents usually used for dyeing keratinous fibers and as defined above.
  • composition which is finally applied to the keratin fibers may be in various forms, such as in the form of liquids, creams, gels or in any other form suitable for dyeing keratinous fibers, and especially human hair.
  • the coloring process can be carried out at room temperature or at higher temperatures for example by using a hair dryer, a drying helmet, a straightening iron, etc.
  • This composition is mixed weight for weight at the time of use with oxygenated water containing 20 volumes then the mixture is applied to a lock of natural hair containing 90% of white hair and a lock of permanent hair containing 90 % of white hair.
  • the locks are then shampooed, rinsed and dried.
  • the locks thus treated have a strong and homogeneous copper color and are soft to the touch.
  • a direct coloring composition is obtained from the 0.5% Acid Orange 7 dye in a mixture consisting of 4% tripropylene glycol n-propyl ether and 96% water acidified with citric acid (qsp pH 2.7). .
  • This composition is then applied for 20 minutes on a lock of natural hair containing 90% of white hair and on a lock of permanent hair containing 90% of white hair. After rinsing and drying, the locks are colored orange in a powerful and aesthetic way.
  • Example 3 A direct dyeing composition is obtained from the dye 1 (beta- hydroxyethylamino) -2-nitro-4-aminobenzene at 0.6% in a mixture consisting of 4% tripropylene glycol n-propyl ether and 96% water .
  • the composition is then applied for 20 minutes on a lock of natural hair containing 90% of white hair and on a lock of permanent hair containing 90% of white hair. After rinsing and drying, the locks are colored in intensely and aesthetically intense red.

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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)
EP06755457A 2005-04-27 2006-04-27 Färbemittel mit einem farbstoff und einem propylenglykolderivat Withdrawn EP1879547A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0551084A FR2885042B1 (fr) 2005-04-27 2005-04-27 Composition de coloration comprenant une matiere colorante et un derive du propylene glycol
US67820505P 2005-05-06 2005-05-06
PCT/FR2006/000953 WO2006114529A1 (fr) 2005-04-27 2006-04-27 Composition de coloration comprenant une matiere colorante et un derive du propylene glycol

Publications (1)

Publication Number Publication Date
EP1879547A1 true EP1879547A1 (de) 2008-01-23

Family

ID=35335778

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06755457A Withdrawn EP1879547A1 (de) 2005-04-27 2006-04-27 Färbemittel mit einem farbstoff und einem propylenglykolderivat

Country Status (8)

Country Link
US (1) US7976584B2 (de)
EP (1) EP1879547A1 (de)
JP (1) JP2008539212A (de)
CN (1) CN101208072A (de)
BR (1) BRPI0612960A2 (de)
FR (1) FR2885042B1 (de)
MX (1) MX2007013328A (de)
WO (1) WO2006114529A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2901125B1 (fr) * 2006-05-22 2009-02-13 Oreal Preparation d'une formulation a partir d'un fluide sous pression, d'un agent cosmetique et d'un hydrotrope hydroxyle, procede de traitement la mettant en oeuvre

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3328971A1 (de) * 1983-08-11 1985-02-21 Blendax-Werke R. Schneider Gmbh & Co, 6500 Mainz Schaumaerosol-zubereitung
LU86833A1 (fr) * 1987-04-02 1988-12-13 Oreal Procede de teinture des fibres keratiniques avec le 5,6-dihydroxyindole associe a un iodure et une composition de peroxyde d'hydrogene a ph alcalin
JPH0699285B2 (ja) * 1989-07-07 1994-12-07 花王株式会社 毛髪化粧料
JP2523419B2 (ja) * 1991-08-30 1996-08-07 花王株式会社 ケラチン質繊維処理剤組成物
FR2692573B1 (fr) * 1992-06-19 2001-08-31 Oreal Nouvelles 2-nitro p-phénylènediamines hydroxyéthylées et leur utilisation en teinture des fibres kératiniques.
FR2741530B1 (fr) * 1995-11-23 1998-01-02 Oreal Utilisation pour la coloration temporaire des cheveux ou poils d'animaux d'une composition a base d'une dispersion de polymere filmogene et d'un pigment non-melanique
FR2812810B1 (fr) * 2000-08-11 2002-10-11 Oreal Composition pour la teinture d'oxydation des fibres keratiniques comprenant un polymere amphiphile cationique, un alcool gras oxyalkylene ou polyglycerole et un solvant hydroxyle
DE60300043T3 (de) * 2002-05-28 2007-08-30 Kpss-Kao Professional Salon Services Gmbh Haarpflegezusammensetzung zur Reduzierung des Ausblutens von sauren Farben aus farblich verändertem Humanhaar

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006114529A1 *

Also Published As

Publication number Publication date
BRPI0612960A2 (pt) 2010-12-07
WO2006114529A1 (fr) 2006-11-02
CN101208072A (zh) 2008-06-25
FR2885042B1 (fr) 2009-10-30
MX2007013328A (es) 2008-01-11
JP2008539212A (ja) 2008-11-13
FR2885042A1 (fr) 2006-11-03
US7976584B2 (en) 2011-07-12
US20090165222A1 (en) 2009-07-02

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