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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
• • 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 composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, comprising as oxidation base a 1- (4-aminophenyl) pyrrolidine substituted at least in positions 2 and 4.
• oxidation dye precursors in particular ortho or para-phenylenediamines, ortho or para-aminophenols.
• heterocyclic compounds such as diaminopyrazole derivatives, pyrazolo [1,5-a] pyrimidine derivatives, pyrimidine derivatives, pyridine derivatives, 5,6-dihydroxyindole derivatives, 5,6-dihydroxyindoline derivatives generally called oxidation bases.
• the precursors of oxidation dyes, or oxidation bases are colorless or weakly colored compounds which, associated with oxidizing products, can give rise, through an oxidative condensation process, to colored and coloring compounds.
• the shades obtained with these oxidation bases can be varied by associating them with couplers or color modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta- hydroxyphenols and certain heterocyclic compounds such as for example derivatives of pyrazolo [1, 5-b] -1, 2,4, -triazoles, derivatives of pyrazolo [3,2-c] -1, 2,4, -triazoles ,. pyrazolo derivatives [1,5-a] pyrimidines, pyridine derivatives, pyrazol-5-one derivatives, indoline derivatives and indole derivatives.
• couplers or color modifiers the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta- hydroxyphenols and certain heterocyclic compounds such as for example derivatives of pyrazolo [1, 5-b] -1, 2,4, -triazoles, derivatives of pyrazolo [3,2-c] -1, 2,4,
• the so-called "permanent" coloration obtained thanks to these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must be without drawbacks from the toxicological point of view, it must make it possible to obtain nuances in the desired intensity, to have good resistance to external agents (light, bad weather, washing, permanent waving, perspiration, friction).
• the dyes must also make it possible to cover white hair, and finally be the least selective possible, that is to say allow to obtain the smallest possible color differences throughout the same keratin fiber, which can be in differently sensitized effect (ie damaged) between its tip and its root. They must also have good chemical stability in the formulations. They must have a good toxicological profile.
• N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine and 2- ( ⁇ -hydroxyethyl) paraphenylenediamine have the disadvantage of leading to a less wide variety of shades and of conferring less color intensity, less d uniformity in hair as para-phenylenediamine and 4-amino-2-methylaniline. It is the same for 2- (hydroxyalkoxy) -paraphenylene diamine which give the hair colors which evolve and change over time.
• the oxidation bases which are too oxidizable and which react with couplers according to accelerated reaction rates, generally lead to the formation of dyes outside the keratin fiber.
• the intensities, tenacity and uniformity of the colorings thus obtained on the hair are generally insufficient.
• US Patent 5,851,237 proposes the use of 1- (4-aminophenyl) pyrrolidine derivatives optionally substituted on the benzene nucleus in order to replace paraphenylenediamine.
• the same patent very preferably proposes the use of 1- (4-aminophenyl) pyrrolidine as a substitute for paraphenylenediamine.
• Patent application JP 11158048 proposes hair coloring compositions offering good spreading properties, ease of application and resistance to shampoo. These compositions contain at least one compound chosen from 4-aminoaniline derivatives optionally substituted on the benzene ring and one of the nitrogen atoms of which is included in a 5- to 7-membered carbon ring, or at least one compound chosen from 4-aminoaniline derivatives optionally substituted on the benzene ring and one of the nitrogen atoms of which is substituted by a radical Zi and a radical Z 2 , Zi being an alkyl, aryl or heterocycle group, and Z 2 being a radical - (CH 2 - CH 2 -O) -Z 3 where Z 3 represents a hydrogen atom, an alkyl, aryl or heterocycle group.
• this patent application demonstrates that the preferred derivatives N- (3-isopropyloxy-4-aminophenyl) -2.5- dimethylpyrrolidine, 1- (3-methyl 4-Amino-phenyl) 2,5- dihydroxyethyl-pyrrolidine, N- (3-methyl-4-aminophenyl) -3- (2-hydroxyethyloxy) pyrrolidine, and N- (3-methyl -4-aminophenyl) -2-methyl-4-hydroxypyrrolidine behave like oxidation bases equivalent to paraphenylenediamine derivatives whose nitrogen atom is included in a functionalized piperidine 6-membered ring.
• compositions containing derivatives of paraphenylenediamine having a nitrogen atom included in a functionalized pyrrolidine cycle as described in patent application JP 11158048 do not make it possible to confer on the hair dyeing results equivalent to those obtained with para -phenylenediamine or paratoluenediamine.
• compositions for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair comprising, in a medium suitable for dyeing, - at least one base oxidation chosen from the compounds of formula (I) below, and / or their addition salts with an acid
• - R represents a halogen atom
• a carbon chain in C- ⁇ -C 7 saturated or which may contain one or more double bonds and / or one or more triple bonds, linear or branched, which may be in the form of a ring having 3 to 6 members, one or more atoms of carbon of the chain which can be replaced by an oxygen, nitrogen or sulfur atom, by an SO 2 group or by a halogen atom, the radical Ri not comprising a peroxide bond, nor of diazo, nitro radicals or nitroso;
• R 2 represents a carbon chain in CC 4 , saturated or unsaturated; an alkyl radical in CC substituted by an alkoxy radical in CrC 4 , acetoxy, amino carboxyl, carbamoyl, (mono or dialkyl) (C ⁇ -C 4 ) carbamoyl, alkoxy (CC 4 ) carbonyl, monohydroxyalkoxy in CC 6 or by a polyhydroxyalkoxy group C 2 -C 6 ; a CC 4 monohydroxyalkyl radical; a CC 6 polyhydroxyalkyl radical; a C- ⁇ -C 4 aminoalkyl radical in which the amine is mono or disubstituted by a CC 4 alkyl, acetyl, C 4 -C monohydroxyalkyl or C 2 -C 6 polyhydroxyalkyl radical; a C 2 -C 4 polyaminoalkyl radical; a C 2 -C alkyl radical substituted by at least one group amino and at least one hydroxy group;
• R 3 represents a hydroxy radical; an amino radical; a saturated or unsaturated C- ⁇ -C carbon chain; a radical -OR 4 in which R represents a C 1 -C 4 alkyl radical, saturated or unsaturated, which may be substituted by one or more radicals chosen from the group consisting of a halogen atom, a hydroxy radical, CC alkoxy 2 , amino or aminoalkyl CC 2 ; a radical -NR 5 R 6 in which R 5 and R 6 independently of one another represent a hydrogen atom, an alkyl radical in CC 4 , an alkyl radical in CC 4 substituted by one or more radicals chosen from the group consisting of a halogen atom, a hydroxy, CC 2 alkoxy, amino or CC 2 aminoalkyl radical.
• -n is between 0 and 2, it being understood that when n is equal to 2 then the radicals Ri can be identical or different, with the exception of the compound 1- (3-methyl 4-Amino-phenyl) 4-hydroxy 2 -methyl-pyrrolidine and of compound 1- (4-Amino-phenyl) 4-hydroxy 2-hydroxymethyl-pyrrolidine.
• the 1- (4-aminophenyl) - pyrrolidine derivatives of formula (I) substituted at least in positions 2 and 4 of the pyrrolidine ring can be used as oxidation dye precursors, and in addition make it possible to obtain dye compositions which lead to powerful coloring of keratin fibers and which exhibit good resistance to external agents (light, bad weather, washing, permanent waving, perspiration, friction). Finally, these compounds appear to be easily synthesizable and are chemically stable.
• radicals, groups, or carbon chains defined above in formula (I) may be linear or branched.
• radical Ri when it is indicated that one or more of the carbon atoms of the radical Ri may be replaced by an oxygen, nitrogen or sulfur atom or by an SO 2 group, and / or that said radical Ri may contain one or more double bonds and / or one or more triple bonds, this means that the following transformations can be made, for example: ⁇ - CH; - H can become -0-H
• the radical Ri is preferably chosen from a chlorine or bromine atom, a methyl, ethyl, isopropyl, vinyl, allyl, methoxymethyl, hydroxymethyl,, 1-carboxymethyl, 1 -aminomethyl, 2- radical. carboxyethyl, 2-hydroxyethyl, 3-hydroxypropyl, 1, 2-dihydroxyethyl, 1-hydroxy-2-aminoethyl, 1-amino-2-hydroxyethyl, 1, 2-diaminoethyl, methoxy, ethoxy, allyloxy, 2-hydroxyethyloxy.
• R-i is chosen from a methyl, hydroxymethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, methoxy, 2-hydroxyethoxy, and preferably a methyl, hydroxymethyl or 1,2-dihydroxyethyl radical.
• n is equal to 0 or 1.
• R is preferably in position 3 of the benzene ring.
• the radical R 2 of formula (I) is preferably chosen from the hydroxymethyl radical, the aminomethyl radical, the carboxyl radical, the carbamoyie radical, the 2-hydroxyethyloxymethyl radical, the 2-hydroxyethylaminomethyl radical, the methoxymethyl.
• the radical R 3 of formula (I) is preferably chosen from a hydroxy radical, an acetoxy radical, an amino radical, a methylamino radical, a dimethylamino radical, a hydroxyethylamino radical, a hydroxyethyloxy radical, an acetamido radical.
• R 3 is a hydroxy, amino, 2-hydroxyethylamino or 2-hydroxyethyloxy radical and R 2 is chosen from a carboxyl, carbamoyie, aminomethyl, 2-hydroxyethyloxymethyl, 2-hydroxyethylaminomethyl, methoxymethyl radical.
• the asymmetric carbons substituted by the radicals R 2 and R 3 may be independently of each other of configuration (R) and / or (S).
• R 2 and R 3 may be independently of each other of configuration (R) and / or (S).
• the addition salts with an acid of the compounds of formula (I) according to the invention are preferably chosen from inorganic or organic salts such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates , lactates and acetates.
• the hydrochlorides are particularly preferred.
• the compound (s) of formula (I) according to the invention preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight .
• the medium suitable for dyeing generally consists of water or a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water.
• organic solvent mention may, for example, be made of lower CrC alkanols, such as ethanol and isopropanol; polyols or polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, analogous products and mixtures thereof.
• the solvents may be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.
• the pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers.
• acidifying agents there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic 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, sulfonic acids.
• basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of formula (II) below:
• W is a propylene residue optionally substituted by a hydroxyl group or a CC 6 alkyl radical
• R 4 , R 5 , R 6 and R 7 which may be identical or different, represent a hydrogen atom, an alkyl radical in CC 6 or hydroxyalkyl in CrC 6 .
• the dye composition in accordance with the invention may also contain, in addition to the compound or compounds of formula (I) defined above, at least one additional oxidation base which can be chosen from the oxidation bases conventionally used in dyeing oxidation and among which there may be mentioned paraphenylenediamines different from the compounds of formula (I), bis-phenylalkylenediamines, paraaminophenols, ortho-aminophenols and heterocyclic bases.
• paraphenylenediamines mention may more particularly be made, for example, of paraphenylenediamine, paratoluylenediamine, 2-chloro paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine , 2,5-dimethyl paraphenylenediamine, N, N-dimethyl paraphenylenediamine, N, N-diethyl paraphenylenediamine, N, N-dipropyl paraphenylenediamine, 4-amino N, N-diethyl 3-methyl aniline, N, N-bis- ( ⁇ - hydroxyethyl) paraphenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-methyl aniline, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-chloro aniline , 2- ⁇ -hydroxyethyl
• para-phenylenediamines very particularly preferred are paraphenylenediamine, paratoluylenediamine, 2-isopropyl paraphenylenediamine, 2- ⁇ -hydroxyethyl paraphenylenediamine, 2- ⁇ -hydroxyethyloxy paraphenylenediamine, 2,6-dimethyl , 6-diethyl paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 2-chloro paraphenylenediamine, 2- ⁇ -acetylaminoethyloxy paraphenylenediamine, and their addition salts with a acid.
• para-aminophenol mention may more particularly be made, for example, of para-aminophenol, 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4-amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4-amino 2- ( ⁇ -hydroxyethyl aminomethyl) phenol, 4-amino 2-fluoro phenol, and their addition salts with an acid.
• para-aminophenol 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4-amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4-amino 2- ( ⁇ -hydroxyethyl aminomethyl) phenol, 4-amino 2-fluoro phenol, and their addition salts with an
• ortho-aminophenols mention may more particularly be made, by way of example, of 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methyl phenol, 5-acetamido 2-amino phenol, and their addition salts with an acid.
• heterocyclic bases that may be mentioned more particularly by way of example, pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
• pyridine derivatives mention may more particularly 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.
• pyrimidine derivatives mention may more particularly be made of the compounds described for example in patents DE 2,359,399; JP 88-169,571; JP 05 163 124; EP 0 770 375 or patent application WO 96/15765 such as 2,4,5,6-tetra-aminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2,4-dihydroxy 5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which may be mentioned pyrazolo - [1,5-a] -pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo- [1,5-a] - pyrimidine-3,7-diamine; pyrazolo- [1,5-a] -pyrimidine
• pyrazole derivatives mention may more particularly be made of the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 such as 4,5-diamino 1-methyl pyrazole, 4,5-diamino l- ( ⁇ -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-methyl pyrazole, 4,5-diamino
• these additional oxidation bases preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.
• the oxidation dye compositions in accordance with the invention may also contain at least one coupler and / or at least one direct dye, in particular for modifying the nuances or enriching them with reflections.
• the couplers which can be used in the oxidation dye compositions in accordance with the invention can be chosen from the couplers conventionally used in oxidation dyeing and among which mention may be made of metaphenylenediamines, meta-aminophenols, metadiphenols, naphthols and heterocyclic couplers such as, for example, indole derivatives, indolinic derivatives, pyridine derivatives, indazole derivatives, pyrazolo derivatives [1, 5-b] -1, 2,4 -triazole, pyrazolo [3,2-c] -1,2,4-triazole derivatives, benzimidazole derivatives, benzothiazole derivatives, benzoxazole derivatives, 1,3-benzodioxole derivatives and pyrazolones, and their addition salts with an acid.
• metaphenylenediamines meta-aminophenols, metadiphenols, naphthols and heterocyclic couplers
• couplers are more particularly chosen from 2-methyl 5-amino phenol, 5-N- ( ⁇ -hydroxyethyl) amino 2-methyl phenol, 3-amino phenol, 1, 3-dihydroxy benzene, 1, 3 -dihydroxy 2-methyl benzene, 4-chloro 1, 3-dihydroxy benzene, 2,4-diamino l- ( ⁇ -hydroxyethyloxy) benzene, 2-amino 4- ( ⁇ -hydroxyethylamino) 1 -methoxy benzene, 1,3-diamino benzene, 1,3-bis- (2,4-diaminophenoxy) propane, sesamol, ⁇ -naphthol, 2-methyl-1-naphthol, 6-hydroxy indole, 4- hydroxy indole, 4-hydroxy N-methyl indole, 6-hydroxy indoline, 6-hydroxybenzomorpholine, 3,5 diamino 2,6dimethoxy pyridine, 1-N ⁇ hydroxyethy
• the coupler or couplers preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dye composition and even more preferably from 0.005 to 5% by weight approximately of this weight.
• the dye composition according to the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or their mixtures, anionic, cationic polymers , non-ionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as for example silicones, film-forming agents, preserving agents, opacifying agents.
• adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or their mixtures, anionic, cationic polymers , non-ionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning
• the dye composition according to the invention can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair.
• compositions of the invention for the oxidation dyeing of keratin fibers, and in particular human fibers such as the hair.
• the invention also relates to a process for dyeing keratin fibers and in particular human keratin fibers such as the hair, using the dye composition as defined above.
• At least one dye composition as defined above is applied to the fibers, the color being revealed at acidic, neutral or alkaline pH using an oxidizing agent which is added just at the time of use. the dye composition or which is applied separately, simultaneously or sequentially.
• the dye composition described above is preferably mixed, at the time of use, with an oxidizing composition containing, in a medium suitable for dyeing, at least one oxidizing agent present in an amount sufficient to develop coloring.
• the mixture obtained is then applied to the keratin fibers and left to stand for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which it is rinsed, washed with shampoo, rinsed again and dried.
• the oxidizing agent can be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratin fibers, and among which mention may be made of hydrogen peroxide, urea peroxide, alkali metal bramates, persalts such as as perborates and persulfates, and enzymes among which mention may be made of peroxidases, oxidoreductases with 2 electrons such as uricases and oxygenases with 4 electrons such as laccases. Hydrogen peroxide is particularly preferred.
• the pH of the oxidizing composition containing the oxidizing agent as defined above is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibers preferably varies between 3 and 12 approximately, and again more preferably between 5 and 11. It is adjusted to the desired value by means of agents acidifiers or basifying agents usually used in dyeing keratin fibers and as defined above.
• the oxidizing composition as defined above may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
• composition which is finally applied to the keratin fibers can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair. .
• Another object of the invention is a device with several compartments or "kit” for dyeing or any other packaging system with several compartments of which a first compartment contains the dye composition as defined above and a second compartment contains the composition. oxidant as defined above.
• These devices can be equipped with a means enabling the desired mixture to be delivered to the hair, by any means known to a person skilled in the art, for example the devices described in patent FR-2,586,913 in the name of the applicant.
• the subject of the invention is also the colored product resulting from the oxidation of at least one compound of formula (I) as defined above in the presence of at least one oxidizing agent, and optionally in the presence of at least one coupler and / or at least one additional oxidation base.
• colored products can also be in the form of pigments and be used as direct dyes for the direct dyeing of hair or even be incorporated in cosmetic products such as for example in makeup products.
• each dye composition is mixed with an equal amount of an oxidizing composition consisting of a solution of hydrogen peroxide at 20 volumes (6% by weight) and having a pH of approximately 3.
• Each mixture obtained has a pH of approximately 9.5 and is applied for 30 minutes to locks of natural gray hair containing 90% white hairs.
• the locks of hair are then rinsed, washed with a standard shampoo and then dried.
• the locks of hair were dyed in the shades shown in the table below:

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  • 2000-12-06 FR FR0015843A patent/FR2817473B1/fr not_active Expired - Fee Related
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  • 2001-11-14 AU AU2002218373A patent/AU2002218373A1/en not_active Abandoned
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