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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/415—Aminophenols
• • 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
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/16—Emollients or protectives, e.g. against radiation
• • 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

• This invention relates to hair coloring compositions for dyeing hair a yellow color, which dyed hair is characterized by improved wear properties. More particularly, the invention relates to hair coloring compositions for dyeing hair a yellow or blonde color in which the dyed hair retains the dyed color intensity, color brightness and color vibrancy, even on exposure to light or shampooing.
• Coloration of hair is a procedure practiced from antiquity employing a variety of means.
• the most extensively used method employed to color hair is to color hair by an oxidative dyeing process employing hair coloring systems utilizing one or more oxidative hair coloring agents in combination with one or more oxidizing agents. .
• a peroxy oxidizing agent is used in combination with one or more oxidative hair coloring agents, generally small molecules capable of diffusing into hair and comprising one or more primary intermediates and one or more couplers.
• a peroxide material such as hydrogen peroxide, is employed to activate the small molecules of primary intermediates so that they react with couplers to form larger sized complexes in the hair shaft to color the hair in a variety of shades and colors.
• Oxidative hair color products sometimes employ o-aminophenol compounds, such as 6-amino-m-cresol or o-aminophenol for this purpose.
• the resulting yellow color has poor stability to light. This is noticeable for the consumer in a loss of vibrancy and drabbing of the color with time.
• yellow direct dye additives are used in oxidative hair color products as a source of yellow hair color.
• drawback of utilizing such a coloration process for dyeing of hair is the relative fast and large loss of the yellow coloration experienced after repeated shampooing. Again, the consumer will notice undesirable color changes and loss of vibrancy.
• the present invention is directed to a human hair dyeing composition for the oxidative dyeing of human hair comprising, in a suitable carrier or vehicle, a compound of the formula
• R and R 2 are (independently) H; C 1-4 alkyl, optionally substituted with one or more hydroxy- or amino group;
• Ri and R 2 may form a 5- or 6-membered heterocyclic ring optionally containing one additional N- or O- heteroatom in the ring
• Ri and R 2 are independently H; C ⁇ -4 alkyl or hydroxy-alkyl
• the present invention is also directed to a process for dyeing of human hair a yellow color which comprises applying to the hair a hair-dyeing effective amount of a composition containing, in a suitable carrier or vehicle, a compound of the formula
• Ri and R 2 are (independently) H; C ⁇ -4 alkyl, optionally substituted with one or more hydroxy- or amino group; Ri and R 2 may form a 5- or 6-membered heterocyclic ring optionally containing one additional N- or O- heteroatom in the ring
• Ri and R 2 are independently H; C- ⁇ -4 alkyl or hydroxy-alkyl
• the rate of loss of hair coloration due to loss of the direct or known oxidative yellow dye will essentially match the increase in yellow coloration imparted by the oxidatively colored hair obtained by the hair coloring process and composition of this invention.
• oxidative dyeing of hair to a natural blonde or yellow coloration with exceptional wearing properties can be obtained by the use of the present composition and process.
• the composition and process utilize 2,4,5,6-tetraaminopyrimidine as a primary intermediate, 2,6- dihydroxypyridine as a coupler and at least one oxidizing agent.
• the colored hair retains its intensity of coloration and turns gradually brighter and more vibrant over a period of several days.
• the resulting bright yellow coloration has good wearing properties, especially with regard to exposure to light.
• the rate of loss of hair coloration due to loss of the direct or known oxidative yellow dye will essentially match the increase in yellow coloration imparted by the oxidatively colored hair obtained by the hair coloring process and composition of this invention.
• the improved yellow hair coloring composition and method of this invention employs a pyrimidine compound of the formula
• Ri and R 2 are independently H; C 1-4 alkyl, optionally substituted with one or more hydroxy- or amino group; Ri and R 2 may form a 5- or 6-membered heterocyclic ring (such as piperidine or pyrrolidine), optionally containing one additional N- or O- heteroatom in the ring (such as piperazine or morpholine)
• Ri and R 2 are independently H; C- ⁇ -4 alkyl or hydroxy-alkyl
• At least one oxidizing agent preferably a peroxide providing agent, and most preferably hydrogen peroxide (H 2 0 2 ) or precursors therefor.
• the oxidative hair coloring compositions will generally comprise from about 0.01 to about 3.5 weight percent of 2,4,5,6-tetraaminopyrimidine and from about 0.01 to about 2.5 weight percent of 2,6-dihydroxypyridine.
• the molar ratio of primary intermediate to coupler will generally range from about 5:1 to about 1 :5 and be employed in any suitable carrier or vehicle, generally an aqueous or hydroalcoholic solution, preferably an aqueous solution.
• the carrier or vehicle will generally comprise up to about 40 weight percent of the composition.
• the hair coloring system and compositions of this invention may also utilize a yellow direct dye or a known oxidative yellow dye.
• Any suitable yellow direct or known oxidative yellow dye may be employed and will preferably be selected to provide the yellow coloration desired.
• the rate of loss of hair coloration due to loss of the direct or known oxidative yellow dye will essentially match the increase in yellow coloration imparted by the oxidatively colored hair obtained by the hair coloring process and composition of this invention.
• suitable yellow direct dyes that may be employed are N,0-bis(2-hydroxyethyl)-5-nitro-o-aminophenol, 2-amino-4- nitro-6-chlorophenol, 2-amino-5-nitrophenol, and 5-nitro-8-hydroxyquinoline.
• the preferred known oxidative yellow dyes that may be employed are selected from the group consisting of 6-amino-m-cresol, o-amino-phenol, and 2-amino-m-cresol.
• one or more other primary intermediates and one or more other couplers may be employed in the hair coloring systems and compositions in addition to the 2,4,5,6- tetraaminopyrimidine and 2,6-dihydroxypyridine.
• Suitable optional primary intermediates include, for example,
• p-phenylenediamine derivatives such as: 2-methyl-p- phenylenediamine, p-phenylenediamine, 2-chloro-p-phenylenediamine, N- phenyl-p-phenylenediamine, N-(2-methoxyethyl)-p-phenylenediamine, N,N- bis(2-hydroxyethyl)-p-phenylenediamine, 2-hydroxymethyl-p- phenylenediamine, 2-(1-hydroxyethyl)-p-phenylenediamine, 2-(2- hydroxyethyl)-p-phenylenediamine, 4,4'diamino-diphenylamine, 2,6-dimethyl- p-phenylenediamine, 2-isopropyl-p-phenylenediamine, N-(2-hydroxypropyI)-p- phenylene-diamine, 2-propyl-p-phenylenediamine, 1 ,3-
• p-aminophenol derivatives such as: p-aminophenol, p- methylaminophenol, 3-methyl-4-aminophenol, 2-hydroxymethyI-4- aminophenol, 2-methyl-4-aminophenol, 2-(2'-hydroxyethylaminomethyl)-4- aminophenol, 2-methoxymethyl-4-aminophenol, 5-aminosalicylic acid and 1- (5-amino-2-hydroxyphenyl)-ethane-1 ,2-diol;
• o-aminophenol derivatives such as: o-aminophenol, 2,4- diaminophenol, 5-methyl-2-aminophenol, 6-methyl-2-aminophenol, 2- ethylamino-p-cresol and 2-amino-5-acetaminophenol and 4-methyl-2- aminophenol; and
• heterocyclic derivatives such as: 4,5-diamino-1-methylpyrazole, 2- dimethylamino-5-aminopyridine, 1 -(2-hydroxyethyl)-4,5-diaminopyrazole, 4- hydroxy-2,5,6-triaminopyrimidine, 2-(2-hydroxyethylamino)-6-methoxy-3- aminopyridine and 3-amino-2-methylamino-6-methoxypyhdine.
• the primary intermediates can be employed in the form of a free base or in the form of an acid additive salt thereof, such as, for example, as a hydrochloride, a hydrobromide, a sulfate or the like.
• Suitable optional additional couplers include, for example,
• phenols, resorcinol and naphthol derivatives such as: 1 ,7- dihydroxynaphthalene, resorcinol, 4-chlororesorcinol, 1 -naphthol, 2-methyI-1- naphthol, 1-acetoxy-2-methylnaphthaIene, 1 ,5-dihydroxynaphthalene, 2,7- dihydroxynaphthalene, hydroquinone, 2-methylresorcinol, 1-hydroxy-6- aminonaphthalene-3-sulfonic acid, 2-isopropyl-5-methylphenol, 1 ,5-dihydroxy- 1 ,2,3,4-tetrahydronaphthalene, 2-chIoro-resorcinol, 2,3-dihydroxy-1 ,4- naphthoquinone and 1-naphthol-4-sulfonic acid, 1 ,2,3-trihydroxybenzene;
• m-phenylenediamines such as: m-phenylenediamine, 2,4-diamino- phenoxyethanol, N,N-bis(2-hydroxyethyl)-m-phenylenediamine, 2,6- diaminotoluene, 2-N,N-bis(hydroxyethyl)-2,4-diaminophenetole, 1 ,3-bis(2,4- diaminophenoxy)propane, 1 -hydroxyethyl-2,4-diaminobenzene, 2-amino-4-(2- hydroxyethylamino)anisole, 4-(2-aminoethoxy)-1 ,3-diaminobenzene, 2,4- diaminophenoxyacetic acid, 4,6-bis(2-hydroxyethoxy)-m-phenylenediamine, 2,4-diamino-5-methylphenetole, 2,4-diamino-5-hydroxyethoxy-toluen
• m-aminophenols such as: m-aminophenol, 2-hydroxy-4-(carbamoyl- methylamino)toluene, m-carbamoylmethylaminophenol, 6- hydroxybenzomorpholine, 2-hydroxy-4-aminotoluene, 2-hydroxy-4-(2- hydroxyethylamino)toluene, 4,6-dichloro-m-amino-phenol, 2-methyl-m- aminophenol, 2-chloro-6-methyl-m-aminophenol, 2-(2-hydroxyethoxy)-5- aminophenol, 2-chloro-5-trifluoroethylaminophenol, 4-chloro-6-methyl-m- aminophenol, N-cyclopentyl-3-aminophenol, N-hydroxyethyl-4-methoxy-6- methyl-m-aminophenol and 5-amino-4-methoxy-2-methyIphenol; and
• heterocyclic derivatives such as: 1-phenyl-3-methyl-5-pyrazolone, 6- methoxy-8-aminoquinoline, 2,6-dihydroxy-4-methylpyridine, 5-hydroxy-1 ,4- benzodioxane, 3,4-methylenedioxyphenol, 4-(2-hydroxyethylamino)-1 ,2- methylene-dioxybenzene, 2,6-dihydroxy-3,4-dimethylpyridine, 5-chloro-2,3- dihydroxypyridine, 3,5-diamino-2,6-dimethoxypyridine, 3,4-methylene- dioxyaniline, 2,6-bis(2-hydroxyethoxy)-3,5-diaminopyridine, 4-hydroxyindole, 3-amino-5-hydroxy-2,6-dimethoxypyridine, 5,6-dihydroxyindole, 7- hydroxyindole, 5-hydroxyindole, 2-bromo-4,5-methylenedioxyphenol, 6- hydroxyindole, 2-amin
• p-phenylenediamine derivatives such as: 2-methyl-p- phenylenediamine, p-phenylenediamine, N-(2-methoxyethyl)-p- phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, 2-(1 - hydroxyethyl)-p-phenyIenediamine, 2-(2-hydroxyethyl)-p-phenylenediamine, and 2-(1 ,2-dihydroxyethyl)-p-phenylenediamine;
• p-aminophenol derivatives such as: p-aminophenol, p- methylaminophenol, 3-methyl-4-aminophenol, 2-methoxymethyl-4- aminophenol and 1-(5-amino-2-hydroxy-phenyl)-ethane-1 ,2-diol;
• o-aminophenol derivatives such as: o-aminophenol, 2-ethylamino-p- cresol, 5-methyl-2-aminophenol, 6-methyl-2-aminophenol and 2-amino-5- acetamino-phenol, 4-methyl-2-aminophenol; and
• heterocyclic derivatives such as: 4,5-diamino-1-methylpyrazole, 1-(2- hydroxyethyl)-4,5-diaminopyrazole, and 2-dimethyl-amino-5-aminopyridine.
• Preferred optional additional couplers include:
• phenols, resorcinol and naphthol derivatives such as: 2-methyl-1- naphthol, 1-acetoxy-2-methylnaphthalene, 1 ,7-dihydroxynaphthalene, resorcinol, 4-chloro-resorcinol, 1 -naphthol, 1 ,5-dihydroxynaphthalene, 2,7- dihydroxynaphthalene, hydroquinone, 2-methylresorcinol and 2-isopropyl-5- methylphenol;
• m-phenylenediamines such as: m-phenylenediamine, 2,4-diamino- phenoxyethanol, 1 ,3-bis(2,4-diaminophenoxy)propane, 2-amino-4-(2- hydroxyethyl-amino)anisole and 4,6-bis(2-hydroxyethoxy)-m- phenylenediamine, 3-(2,4-diamino-phenoxy)-1 -propanol;
• m-aminophenols such as: m-aminophenol, 6-hydroxybenzomorpholine,
• heterocyclic derivatives such as: 1-phenyl-3-methyl-5-pyrazolone, 3,4- methylenedioxyphenol, 3,4-methylenedioxyaniline, 4-hydroxyindole, 5,6- dihydroxyindole, 7-hydroxyindole, 5-hydroxyindole, 6-hydroxyindole, isatin, 2,6-diamino-pyridine and 2-amino-3-hydroxypyridine.
• Most preferred optional primary intermediates include:
• p-phenylenediamine derivatives such as: 2-methyl-p- phenylenediamine, p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p- phenylenediamine, 2-(1-hydroxyethyl)-p-phenylenediamine and 2-(2- hydroxyethyl)-p-phenylenediamine;
• p-aminophenol derivatives such as: p-aminophenol, p- methylaminophenol, 3-methyl-4-aminophenol and 1-(5-amino-2- hydroxyphenyl)-ethane-1 ,2-diol;
• o-amino derivatives such as: o-aminophenol, 2-ethylamino-p-cresol, 5- methyl-2-aminophenol, 6-methyl-2-aminophenol and 2-amino-5- acetaminophenol; and
• heterocyclic derivatives such as: 1-(2-hydroxyethyl)-4,5- diaminopyrazole.
• Most preferred optional additional couplers include:
• phenols, resorcinol and naphthol derivatives such as: 2-methyl-1- naphthol, 1-acetoxy-2-methylnaphthalene, resorcinol, 4-chlororesorcinol, 1- naphthol and 2-methylresorcinol;
• m-phenylenediamines such as: 2,4-diaminophenoxyethanol, 2-amino- 4-(2-hydroxyethylamino)anisole and 4,6-bis(2-hydroxyethoxy)-m- phenylenediamine and 3-(2,4-diaminophenoxy)-1-propanol;
• m-aminophenols such as: m-aminophenol, 6-hydroxybenzomorpholine, 2-hydroxy-4-aminotoluene, 2-hydroxy-4-(2-hydroxyethylamino)toluene and 2- methyl-m-aminophenol; and
• heterocyclic derivatives such as: 1-phenyl-3-methyl-5-pyrazolone, 2- amino-3-hydroxypyridine and 6-hydroxyindole.
• the dye composition in this invention can be formulated in a lotion or in a cream or gel by including the appropriate types and amounts of surfactants, emulsifiers or polymers and alkalizing agents.
• the surfactants and emulsifiers can be anionic, cationic or nonionic, and they can be hydrophobic or hydrophilic. Examples of these surfactants and emulsifiers are: Sodium lauryl sulfate, ammonium lauryl sulfate, cetyl alcohol, cetearyl alcohol, oleic acid, dilinoeic acid, polyethylene glycols of various fatty alcohols, lauramide
• DEA lauramide MEA
• behenetrimonium chloride cetrimonium chloride
• cocamidopropyl betaine examples include monoethanolamine, ammonium hydroxide, sodium hydroxide and sodium carbonate.
• the composition is mixed with an oxidizing agent, such as hydrogen peroxide, prior to use on hair. At the end of the coloring period, which can range from 5 minutes to 40 minutes, the composition is washed from the hair with ordinary water rinse followed by a shampoo.
• Typical dye compositions are described in the following examples:
• the dyeing solution was mixed with an equal amount of 6% hydrogen peroxide.
• the resulting dyeing formulation was applied to the hair and permitted to remain in contact with the hair for 30 minutes.
• the dyed hair was then shampooed and rinsed with water and dried.
• coloration results were measured using a Minolta spectrophotometer Chroma Meter 3700d reflectometer.
• the Minolta Chroma Meter 3700d spectrophotometer uses reflected light from a surface and gives results in terms of the CIE (International Commission on Illumination) tristimulus values. These values are subsequently transformed mathematically into the L* a* b* color space, wherein the magnitude of changes in hue and intensity of color correspond closely with those perceived by the human eye.
• CIE International Commission on Illumination
• Metric chroma indicates the strength of a color response (i.e., the extent to which a color differs from its matching shade of gray).
• Metric hue angle quantifies hue in degrees, with larger values indicating more yellow hues and smaller values indicating more red (or less yellow) hues.
• the spectrophotometer readings in Table 1 demonstrate the poor yellow coloring and poor light stability of the oxidatively dyed yellow coloring of the prior art.
• the spectrophotometer readings in Table 2 demonstrate the increasing brightness of the yellow coloration of the composition of the invention over a period of ten days following dyeing, and the light stability of the coloration even after ten days and subsequent exposure to 24 hours of the fade-o-meter.

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• 2001
  • 2001-09-18 JP JP2002528192A patent/JP2004509140A/ja active Pending
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