Classifications

• • 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
• • 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
  • A61K8/416—Quaternary ammonium compounds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
  • A61K2800/88—Two- or multipart kits

Definitions

• This invention relates to high aqueous-content hair coloring compositions with good thickening and conditioning properties without detrimental effects on the hair dyeing properties of the composition.
• oxidation dyes of the type comprising primary intermediates and couplers are used in the dyeing of human hair
• the procedure usually involves the use of a two part system.
• One part is the lotion formulation which contains a variety of ingredients, including the oxidation dye precursors, and forms a gel immediately prior to application to the human hair, when mixed with the second part which is the developer formulation containing a suitable oxidizing agent.
• the developer usually contains an oxidizing agent, such as hydrogen peroxide and as a consequence some of the natural melanin pigment of the hair may be initially destroyed.
• the precursors in the lotion penetrate into the hair and are oxidized to produce the desired color.
• Such systems will generally contain 50% or more of organic solvents and surfactants, and require relatively high levels of dye precursors to produce the desired color.
• compositions formed by mixing the lotion and developer must have Theological properties whereby application, either by use of a brush or with the fingers, can readily distribute the dye throughout the hair mass and yet in the absence of stress, dripping or running from the hair during the color development period can be substantially avoided.
• the dye mixture as applied to the hair, should allow rapid diffusion of the dye precursors from the dye mixture into the hair fiber.
• the mixture should preferably contain conditioning agents that leave the hair in a condition such that it is easy to detangle while wet and also feel smooth and be readily managed when dry.
• the lotion and developer should preferably, but not necessarily, have comparable viscosities in order to facilitate mixing.
• the dyeing effect should be rapid, with a dyeing time preferably under thirty minutes.
• the rheological properties have generally been attained by the use of a dye lotion containing a high level of surfactants and organic solvents to provide a thin lotion, which, on mixture with a highly aqueous developer solution of the oxidizing agent, forms a dye mixture with the desired gel-like consistency.
• the disadvantage of this approach is that the dye mixture still contains a high level of surfactants that tend to retard the diffusion of the dye precursors into the hair.
• the preferred surfactants in commercial products have been nonionic or anionic materials that do not provide any conditioning.
• the preferred conditioners for human hair are cationic surfactants that provide excellent conditioning but are incompatible with anionic surfactants.
• U.S. Pat. Nos. 3,303,213; 3,331,781; 3,436,167 and 3,891,385 describe the use, in hair treating compositions, of specific amphoteric surfactants such as the sodium salt of N-(N 1 ,N 1 -dimethyl-aminopropyl)-N 2 -alkyl (fatty) asparagine wherein the “fatty” moiety is derived from the fatty acids of tallow.
• the amphoteric surfactant can be employed with organic solvents and any of a variety of cationic, anionic or non-ionic surface active agents. There is no indication of the use of quaternary ammonium salts in the compositions.
• U.S. Pat. No. 4,402,700 describes hair dyeing compositions containing quaternary ammonium compounds and also cites the possible uses of amphoteric surfactants in the compositions. These compositions, however, require the uses of organic solvents and nonionic surfactants, and the amount of water in the compositions is less than 50%.
• U.S. Pat. No. 4,532,127 describes hair coloring compositions containing oxidative dyes together with an oxidizing agent.
• the compositions require the presence of quaternary amine compounds containing two long chain alkyl radicals each having about 10 to 26 carbon atoms.
• Any of a variety of surfactants may be present in the composition that, although they have a high water content may contain organic solvents.
• the lotions of the patent contain di-long chain alkyl quaternary ammonium compounds in the presence of relatively large amounts of non-ionic surfactants. They are said to be superior to a comparison lotion containing a mono-long chain alkyl quaternary ammonium compound in combination with an amphoteric surfactant.
• the lotions of this patent suffer from the disadvantage of having high levels of surfactant thus inhibiting rapid diffusion of the dye precursors into the hair. Furthermore, di-long chain alkyl quaternary ammonium compounds are poorly biodegradable, particularly as compared to the mono-long chain alkyl quaternary ammonium compounds.
• the compositions disclosed are free of anionic surfactants and anionic polymers.
• U.S. Pat. No. 4,663,158 describes hair conditioning compositions containing an amphoteric surfactant together with at least one quaternary cationic polymer such as poly(methacrylamidopropyl)trimethyl ammonium chloride.
• the compositions are acidic.
• U.S. Pat. No. 4,563,188 discloses hair dyeing compositions containing specific para-phenylenediamine derivatives, which may contain any of several types of surfactants as well as organic solvents.
• U.S. Pat. No. 5,137,538 describes oxidative hair dyeing compositions containing specific para phenylenediamines and N,N 1 -diphenylalkylenediamines.
• the compositions may be acidic or alkaline. They may contain organic solvents and anionic, cationic, non-ionic or amphoteric surfactants.
• U.S. Pat. No. 4,362,528 refers to compositions said to be useful for hair coloring. These compositions comprise oxidative dyes together with any of a variety of cationic polymers. The hair is first treated with such composition and subsequently rinsed with a shampoo composition containing an anionic detergent.
• U.S. Pat. No. 4,240,450 describes hair treating mixtures such as shampoos and hair coloring compositions, which may be oxidative.
• the compositions include cationic and anionic polymers that may be chosen from hundreds of such polymers, which are generically and specifically described.
• U.S. Pat. No. 3,986,825 refers to a variety of hair coloring composition which may be employed with either oxidizing agents or reducing agents and which employ any of a wide variety of surfactant water soluble polymer additives together with anionic, cationic, nonionic or amphoteric surfactants.
• U.S. Pat. No. Re. 33786 teaches that rapid dyeing with highly aqueous compositions can be achieved through the use of a certain acrylate copolymer viz an acrylate/steareth-20 methacrylate copolymer in the developer.
• a similar system employing a certain anionic copolymer of acrylic acid or methacrylic acid with their lower alkyl esters is disclosed in U.S. Pat. No. 5,393,305.
• U.S. Pat. No. 5,376,146 the use of a combination of anionic acrylic polymers, such as the copolymers of both RE 33786 and U.S. Pat. No. 5,393, 305, is disclosed.
• a further object of this invention is to produce such composition employing lowered levels of surfactant in the dyeing composition.
• a further object of this invention is to provide a hair coloring composition, which provides excellent wet feel and wet combing characteristics immediately after the dyeing mixture is washed from the hair.
• the invention comprises a hair dyeing composition containing hydroxypropyl bisisosteramidopropyidimonium chloride (Schercoquat 21AP) as the primary conditioning material in a two-part aqueous hair dyeing composition.
• the invention also comprises a two-part hair aqueous dyeing composition comprising a lotion formulation containing oxidizable dye precursors and at least about 50% by weight water., and a conditioning effective amount of the Schercoquat 21AP conditioning agent.
• This invention comprises a two-part system comprising aqueous, oxidative, hair coloring compositions (lotions and developers) for mixture with each other shortly before use to form a gel.
• the lotion comprises an aqueous alkaline composition having a pH of from about 7 to 11 and a water content of at least about 50% by weight, a tinctorily effective amount of oxidative dye precursors, and a hair conditioning effective amount of Schercoquat 21AP conditioning agent.
• the second part, i.e. the developer is an aqueous composition with a pH of from about 2 to about 6, preferably 2 to 3, containing a peroxide oxidizing agent.
• the invention also comprises a kit or package of the developer and lotion formulations.
• a further aspect of this invention is the use of such two-part system for the oxidative coloration of hair.
• One aspect of this invention comprises a high aqueous-content dye lotion formulation for use in a two-part composition for oxidative dyeing of hair, the dye lotion formulation comprising:
• a conditioning effective amount of hydroxypropyl bisisosteramidopropyldimonium chloride conditioner is a conditioning effective amount of hydroxypropyl bisisosteramidopropyldimonium chloride conditioner.
• a further aspect of this invention comprises a two-part aqueous composition for coloring and providing conditioning to human hair and which forms a gel on mixing of the two parts, the two-part aqueous composition comprising:
• an aqueous lotion first part comprising: a tinctorially effective amount of at least one primary dye intermediate and at least one coupler for the formation of oxidation dyes, a conditioning effective amount of hydroxypropyl bisisosteramidopropyldimonium chloride conditioner, and at least 50% by weight water; and
• an aqueous developer second part comprising: an oxidizing effective amount of a peroxide oxidizer, at least about 70% by weight water.
• a still further aspect of this invention comprises a kit containing a two-part 15 aqueous composition, which forms a gel on mixing of the two parts for coloring human hair comprising separate first and second containers:
• the first container containing an aqueous lotion first part comprising: a tinctorially effective amount of at least one primary dye intermediate and at least one coupler for the formation of oxidation dyes, a conditioning effective amount of hydroxypropyl bisisosteramidopropyldimonium chloride conditioner, and at least 50% by weight water; and
• the second container containing an aqueous developer second part comprising: an oxidizing effective amount of a peroxide oxidizer, at least about 70% by weight water.
• Yet another aspect of this invention comprises a method of coloring human hair which comprises contacting the hair with a mixture of a two-part aqueous composition which forms a gel on mixing of the two parts, wherein the two part aqueous composition comprises:
• an aqueous lotion first part comprising: a tinctorially effective amount of at least one primary dye intermediate and at least one coupler for the formation of oxidation dyes, a conditioning effective amount of hydroxypropyl bisisosteramidopropyidimonium chloride conditioner, and at least 50% by weight water; and
• an aqueous developer second part comprising: an oxidizing effective amount of a peroxide oxidizer, at least about 70% by weight water;
• An even still further aspect of the invention comprises a method for oxidative coloring of hair with a two-part dyeing composition comprising a first dye base lotion formulation and a second developer formulation, wherein the improvement comprises using as the dye base lotion formulation a formulation comprising:
• a conditioning effective amount of hydroxypropyl bisisosteramidopropyldimonium chloride conditioner is a conditioning effective amount of hydroxypropyl bisisosteramidopropyldimonium chloride conditioner.
• the components in the aqueous first part of the compositions of this invention include water, the oxidizable dye precursors, a conditioning effective amount of Shercoquat 21AP conditioning agent and, optionally an anionic, nonionic, amphoteric or cationic surfactant or mixtures thereof, and particularly a monomeric quaternary compound.
• the water content of the composition is at least about 50% by weight and may be as high as 90% or higher and is preferably at least about 65% to about 85%.
• the conditioning effective amount of the Schercoquat 21AP conditioning agent employed will generally be from about 0.1% to about 5% by weight, preferably about 1% to about 3%, and more preferably about 2%.
• Suitable optional anionic surfactants include, for example, the following: the alkali metal, ammonium, or amine salts of alkyl sulfates, alkyl ether sulfates, linear alpha-olefin sulfonates, dialkyl sulfosuccinates, alkylamidosulfosuccinates, and alkyl taurates each having from about C 12 to C 18 alkyl or alkenyl groups.
• Particularly preferred are the salts of lauryl sulfates and lauryl ether sulfates the latter having an average level of ethoxylation of 1-3.
• Amphoteric surfactants belong to the category of surface active chemicals that possess a positive and a negative charge in the same molecule and behave as a cation or an anion depending on the pH of the medium. In general, the positive charge is located on a nitrogen atom while the negative charge is carried by a carboxyl or sulfonate group.
• amphoteric surfactants that are suitable for use in this invention. They include, for example, the asparagine derivatives identified in the first three patents mentioned above as well as a variety of well-known betaines, sultaines, glycinates and propionates that may be represented by the following structural formulas:
• R is an alkyl or alkylamido group containing from about 10 to about 20 carbon atoms
• R, R 1 , R 2 and R 3 are alkyl or hydroxyalkyl groups, which may be the same or different, and contain up to about five carbon atoms and n is a positive integer up to about five.
• Typical amphoteric surfactants that are suitable for use in this invention include: lauryl betaine, lauroamphoglycinate, lauroamphopropylsulfonate, lauroamphopropionate, lauroampho-carboxyglycinate, lauryl sultane, myristamidopropyl betaine, myristyl betaine, myristoamphoglycinate, myristyl propionate, stearoamphoglycinate, stearoamphopropionate, stearoamphopropylsulfonate, stearyl betaine, cocamidoethyl betaine, cocamidopropyl betaine, cocamidopropyl hydroxysultane, cocamidopropyl dimethylamine propionate, cocoamphoglycinate, cocoamphocarboxypropionate, cocoamphocarboxyglycinate, coco-betaine, cocoamphopropionate, coco
• the anionic and amphoteric surfactants and mixtures of these surfactants for use in this invention may be selected from any of a number of known surfactants.
• the amount of such surfactants in the compositions is normally from about 0.5% to 15% by weight, preferably 2% to 8% by weight.
• amphoteric surfactants presently preferred for use in this invention are: cocamidopropyl betaine, coco-betaine, stearyl betaine, cocoampho-carboxyglycinate, cocoamphodipropionate, and stearoamphoglycinate.
• the pH of the lotions of this invention will generally be from about 6.5 to about 11. It is preferred, however, that this pH be in the range of 8.5 to 10.5.
• any of a wide variety of alkaline agents can be used to adjust the pH of the hair coloring compositions.
• Ammonium hydroxide because of its freedom from toxicity over a wide concentration range and its economy, is an acceptable alkalizing agent.
• any other compatible ammonia derivative as an alkalizing agent such as an alkylamine, for example ethylamine, or triethylamine; or alkanolamines, for example ethanolamine, diethanolamine, aminomethyl propanol, aminomethyl propanediol and trishydiroxymethyl aminomethane.
• any other of the organic or inorganic alkalizing agents may be used, such as sodium or potassium hydroxide, sodium or potassium carbonate, sodium phosphate, sodium hydrogen phosphate, sodium silicate, guanidine hydroxide and the like.
• the preferred alkaline reagents are ammonium hydroxide, sodium carbonate and ethanolamine.
• the selected pH will generally be achieved if the lotion contains from about 0. 1% to 10% by weight of alkaline agent.
• the oxidative dye precursors employed in the practice of this invention comprise one or more primary intermediates together with one or more couplers.
• the selection of specific intermediates or couplers determines the ultimate color of the treated hair. Such selection is not a critical aspect of the practice of the invention.
• p-phenylenediamine derivatives such as: benzene-1,4-diamine, 2-methyl-benzene-1,4-diamine, 2-chloro-benzene-1,4-diamine, N-phenyl-benzene-1,4-diamine, N-(2-ethoxyethyl)benzene-1,4-diamine, 2-[(4-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol, (2,5-diamino-phenyl)-methanol, 1-(2,5-diamino-phenyl)-ethanol, 2-(2,5-diamino-phenyl)-ethanol, N-(4-aminophenyl)benzene-1,4-diamine, 2,6-dimethyl-benzene-1,4-diamine, 2-isopropyl-benzene-1,4-diamine, 1-[(4-aminophenyl
• p-aminophenol derivatives such as: 4-amino-phenol, 4-methylamino-phenol, 4-amino-3-methyl-phenol, 4-amino-2-hydroxymethyl-phenol, 4-amino-2-methyl-phenol, 4-amino-2-[(2-hydroxy-ethylamino)-methyl]-phenol, 4-amino-2-methoxymethyl-phenol, 5-amino-2-hydroxy-benzoic acid, 1-(5-amino-2-hydroxy-phenyl)-ethane-1,2-diol, 4-amino-2-(2-hydroxy-ethyl)-phenol, 4-amino-3-(hydroxymethyl)phenol, 4-amino-3-fluoro-phenol, 4-amino-2-(aminomethyl)phenol, and 4-amino-2-fluoro-phenol;
• o-aminophenol derivatives such as: 2-amino-phenol, 2,4-diaminophenol, 2-amino-5-methyl-phenol, 2-amino-6-methyl-phenol, N-(4-amino-3-hydroxy-phenyl)-acetamide, and 2-amino-4-methyl-phenol; and
• heterocyclic derivatives such as: pyrimidine-2,4,5,6-tetramine, 1-methyl -1H-pyrazole-4,5-diamine, 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol, N 2 ,N 2 -dimethyl-pyridine -2,5-diamine, 2-[(3-amino-6-methoxypyridin-2-yl)amino]ethanol, 6-methoxy-N2-methyl-pyridine-2,3-diamine, 2,5,6-triaminopyrimidin-4(1H)-one, pyridine-2,5-diamine, 1-isopropyl-1H-pyrazole-4,5-diamine, 1-(4-methylbenzyl)-1H-pyrazole-4,5-diamine, and 1-(4-chlorobenzyl)-1H-pyrazole-4, 5-diamine.
• 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 couplers include, for example, phenols, resorcinol and naphthol derivatives such as: naphthalene-1,7-diol, benzene-1,3-diol, 4-chlorobenzene-1,3-diol, naphthalen-1-ol, 2-methyl-naphthalen-1-ol, naphthalene-1,5-diol, naphthalene-2,7-diol, benzene-1,4-diol, 2-methyl-benzene-1,3-diol, 7-amino-4-hydroxy-naphthalene-2-sulforic acid, 2-isopropyl-5-methylphenol, 1,2,3,4-tetrahydro-naphthalene-1,5-diol, 2-chloro-benzene-1,3-diol, 4-hydroxy-naphthalene-1-sulfonic acid, benzene-1,
• m-phenylenediamines such as: 2,4-diaminophenol, benzene-1,3-diamine, 2-(2,4-diamino-phenoxy)-ethanol, 2-[(3-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol, 2-mehyl-benzene-1,3-diamine, 2-[[2-(2,4-diamino-phenoxy)-ethyl]-(2-hydroxy-ethyl)-amino]-ethanol, 4- ⁇ 3-[(2,4-diaminophenyl)oxy]propoxy ⁇ benzene-1,3-diamine, 2-(2,4-diamino-phenyl)-ethanol, 2-(3-amino-4-methoxy-phenylamino)-ethanol, 4-(2-amino-ethoxy)-benzene-1,3-diamine, (2,4-diamino-phenoxy)
• m-aminophenols such as: 3-amino-phenol, 2-(3-hydroxy-4-methyl-phenylamino)-acetamide, 2-(3-hydroxy-phenylamino)-acetamide, 5-amino-2-methyl-phenol, 5-(2-hydroxy-ethylamino)-2-methyl-phenol, 5-amino-2,4-dichloro-phenol, 3-amino-2-methyl-phenol, 3-amino-2-chloro-6-methyl-phenol, 5-amino-2-(2-hydroxy-ethoxy)-phenol, 2-chloro-5-(2,2,2-trifluoro-ethylamino)-phenol, 5-amino-4-chloro-2-methyl-phenol, 3-cyclopentylamino-phenol, 5-[(2-hydroxyethyl)amino]-4-methoxy-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 3-(dimethylamino)phenol, 3-(diethylamino)phenol,
• heterocyclic derivatives such as: 3,4-dihydro-2H-1,4-benzoxazin-6-ol, 4-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 6-methoxyquinolin-8-amine, 4-methylpyridine-2,6-diol, 2,3-dihydro-1,4-benzodioxin-5-ol, 1,3-benzodioxol-5-ol, 2-(1,3-benzodioxol-5-ylamino)ethanol, 3,4-dimethylpyridine-2,6-diol, 5-chloropyridine-2,3-diol, 2,6-dimethoxypyridine-3,5-diamine, 1,3-benzodioxol-5-amine, 2,6-bis(2-hydroxyethoxy) -3,5-diaminopyridine, 1H-indol-4-ol, 5-amino-2,6-dimeth
• Preferred primary intermediates include:
• p-phenylenediamine derivatives such as: 2-methyl-benzene-1,4-diamine, benzene-1,4-diamine, 1-(2,5-diamino-phenyl)-ethanol, 2-(2,5-diamino-phenyl)-ethanol, N-(2-methoxyethyl)benzene-1,4-diamine, 2-[(4-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol, and 1-(2,5-diaminophenyl)ethane-1,2-diol;
• p-aminophenol derivatives such as 4-amino-phenol, 4-methylamino-phenol, 4-amino-3-methyl-phenol, 4-amino-2-methoxymethyl-phenol, and 1-(5-amino-2-hydroxy-phenyl)-ethane-1 ,2-diol;
• o-aminophenol derivatives such as: 2-amino-phenol, 2-amino-5-methyl-phenol, 2-amino-6-methyl-phenol, N-(4-amino-3-hydroxy-phenyl)-acetamide, and 2-amino-4-methyl-phenol;
• heterocyclic derivatives such as: pyrimidine-2,4,5,6-tetramine, 1-methyl -1H-pyrazole-4,5-diamine, 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol, and N 2N2-dimethyl-pyridine -2,5-diamine.
• Preferred couplers include:
• phenols, resorcinol and naphthol derivatives such as: naphthalene-1,7-diol, benzene-1,3-diol, 4-chlorobenzene-1,3-diol, naphthalen-1-ol, 2-methyl-naphthalen -1-ol, naphthalene-1,5-diol, naphthalene-2,7-diol, benzene-1,4-diol, 2-methyl-benzene-1 ,3-diol, and 2-isopropyl-5-methylphenol;
• m-phenylenediamines such as: benzene-1 ,3-diamine, 2-(2,4-diamino-phenoxy)-ethanol, 4- ⁇ 3-[(2,4-diaminophenyl)oxy]propoxy ⁇ benzene-1,3-diamine 2-(3-amino-4-methoxy-phenylamino)-ethanol, 2-[2,4-diamino-5-(2-hydroxy-ethoxy)-phenoxy]-ethanol, and 3-(2,4-diamino-phenoxy)-propan-1-ol;
• m-aminophenols such as: 3-amino-phenol, 5-amino-2-methyl-phenol, 5-(2-hydroxy-ethylamino)-2-methyl-phenol, and 3-amino-2-methyl-phenol; and
• heterocyclic derivatives such as: 3,4-dihydro-2H-1,4-benzoxazin-6-ol, 4-methyl-2-phenyl-2 ,4-dihydro-3H-pyrazol-3-one, 1,3-benzodioxol-5-ol, 1,3-benzodioxol -5-amine, 1H-indol-4-ol, 1H-indole-5,6-diol, 1H-indol-7-ol, 1H-indol-5-ol, 1H-indol-6-ol, 1H-indole-2,3-dione, pyridine-2,6-diamine, and 2-aminopyridin-3-ol.
• Most preferred primary intermediates include:
• p-phenylenediamine derivatives such as: 2-methyl-benzene-1,4-diamine, benzene-1,4-diamine, 2-(2,5-diamino-phenyl)-ethanol, 1-(2,5-diamino-phenyl)-ethanol, and 2-[(4-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol;
• p-aminophenol derivatives such as: 4-amino-phenol, 4-methylamino-phenol, 4-amino-3-methyl-phenol, and 1-(5-amino-2-hydroxy-phenyl)-ethane-1,2-diol;
• o-aminophenols such as: 2-amino-phenol, 2-amino-5-methyl-phenol, 2-amino-6-methyl-phenol, and N-(4-amino-3-hydroxy-phenyl)-acetamide; and
• heterocyclic derivatives such as: pyrimidine-2,4,5,6-tetramine and 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol.
• Most preferred couplers include:
• phenols, resorcinol and naphthol derivatives such as: benzene-1,3-diol, 4-chlorobenzene-1,3-diol, naphthalen-1-ol, 2-methyl-naphthalen-1-ol, and 2-methyl-benzene -1,3-diol;
• m-phenylenediamine such as: 2-(2,4-diamino-phenoxy)-ethanol, 2-(3-amino-4-methoxy-phenylamino)-ethanol, 2-[2 ,4-diamino-5-(2-hydroxy-ethoxy)-phenoxy]-ethanol, and 3-(2,4-diamino-phenoxy)-propan-1-ol;
• m-aminophenols such as: 3-amino-phenol, 5-amino-2-methyl-phenol, 5-(2-hydroxy-ethylamino)-2-methyl-phenol, and 3-amino-2-methyl-phenol; and
• heterocyclic derivatives such as: 3,4-dihydro-2H-1,4-benzoxazin-6-ol, 4-methyl -2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and 1H-indol-6-ol, and 2-aminopyridin -3-ol.
• the primary intermediate(s) and coupler(s) in the aqueous lotion of the invention will normally be employed in equimolar quantities, each at a concentration of about 0.0005% to about 5% by weight, preferably 0.005% to 2.5% by weight.
• non-oxidative or direct dyes as a part of the hair color formulation to achieve different color effects.
• direct or non-oxidative dye include, but are not limited to
• Yellow/Orange dyes Acid Orange 3, Disperse Orange 3, Disperse Black 9, HC Orange 1, HC Orange 2, HC Orange 3, HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 7, HC Yellow 9, HC Yellow 10, HC Yellow 11, HC Yellow 12, HC Yellow 13, HC Yellow 14, HC Yellow 15, 4-nitro-o-phenylenediamine, 2-nitro-5-glyceryl methylaniline, 4-nitrophenyl aminoethylurea, hydroxyethyl-2-nitro-p-toluidine, 3-methylamino-4-nitrophenoxyethanol, 2-amino-6-chloro-4-nitrophenol, 2-chloro-6-ethylamino-4-nitrophenol, Basic Yellow 57, Solvent Orange 45, 4-nitro-m-phenylenediamine, Natural Orange 6, 2-hydroxyethylamino-5-nitroanisole, 2-amino-3-nitrophenol, 6-nitro-o-toluidine, N-ethyl-3-nitro PABA, N-hydroxy
• Red-Orange/Red dyes HC Red 1, HC Red 3, HC Red 7, HC Red 10, HC Red 11, HC Red 13, HC Red 14, 2-nitro-p-phenylenediamine, 3-nitro-p-hydroxyethylaminophenol, 4-hydroxypropylamino-3-nitrophenol, 4-amino-3-nitrophenol, picramic acid, N-(2-hyroxyethyl)picramic acid, Basic Red 76, Disperse Red 17, N-methyl-3-nitro-p-phenylenediamine, 2-chloro-5-nitro-N-hydroxyethyl-p-phenylenediamine, 4-amino-2-nitrodiphenylamine-2′-carboxylic acid, and 4-amino-4′-dimethylamino-2-nitrodiphenylamine-2′-carboxylic acid;
• Violet dyes Disperse Violet 1, Disperse Violet 4, HC Blue 2, HC Blue 6, HC Blue 9, HC Blue 10, HC Blue 11, HC Blue 12, HC Violet 1, HC Violet 2, N,N′-bis(2-hydroxyethyl)-2-nitro-p-phenylenediamine, 2-nitro-4-[bis(2-hydroxyethyl)amino]diphenylamine, and Basic Violet 14;
• Blue dyes Disperse Blue 1, Disperse Blue 3, Basic Blue 7, Basic Blue 9, Basic Blue 26, Basic Blue 17, Basic Blue 99; and
• Brown/Black dyes Basic Brown 16, Basic Brown 17, and Acid Black 1.
• the presently preferred cationic polymers are quaternary polymers of diallyldialkylammonium salts in which the alkyl groups are the same or different and contain from 1 to 5 carbon atoms such as Merquat 100 (Calgon) or copolymers of the above with acrylic acid sold under the names Merquat 280 and Merquat 295, such as those described in U.S. Pat. No. 4,772,462.
• Merquat 100 Calgon
• copolymers of diallyldialkylammonium salts with acrylamide such as that sold under the name Merquat 550, are unsuitable for this purpose.
• Onamer M a polydimethylbutenyl chloride end-capped with hydroxyalykl groups of the formula:
• R 3 is a hydroxyalkyl group having 1-5 carbon atoms, preferably 2.
• the surfactants are generally employed in an amount of from about 0.1% to about 5% by weight.
• the viscosity of the completely formulated lotion of the invention when it is ready to mix with the developer, is from about 1 cps to about 5000 cps, preferably 1 cps to 500 cps.
• the lotion may contain organic solvents to assist in dissolving the dye precursors.
• the organic solvent content should be kept at a minimum. More solvent than is necessary to dissolve the precursors may have the effect of retarding diffusion of the precursors into the hair for reaction. Accordingly, the organic solvent content of the lotion may be from 0% by weight to about 5% by weight.
• useful solvents include alcohols containing up to three carbon atoms such as ethanol and isopropanol, polyhydroxy alcohols such as propylene or hexylene glycol and lower alkyl ethers thereof such as ethoxy ethers.
• compositions may be employed in the lotion or in the developer. These include, for example, fragrances, coloring agents and chelating agents. Antioxidants such as sodium sulfite, erythorbic acid, and ascorbic acid may also be included to inhibit premature oxidation.
• the oxidizing composition or developer employed in the invention is an acidic aqueous composition, which comprises the selected oxidizing agent together with one or more anionic polymers, which are insoluble in water.
• the preferred oxidizing agent for use in the developer of the invention is hydrogen peroxide although other peroxides may be employed. These include, for example, urea peroxide, melamine peroxide, perborates and percarbonates such as sodium perborate or percarbonate.
• the concentration of peroxide in the developer may be from about 0.5% to about 40% by weight, preferably 0.5% to 30% by weight. If the preferred hydrogen peroxide is employed, the concentration will be from about 0.5% to about 15% by weight, preferably 3% to 13% by weight.
• An anionic polymer may be used in the developer. It should be stable to the peroxide oxidant, insoluble in the developer and, when the developer is mixed with the lotion, assist in the formation of a gel in which the anionic polymer is soluble.
• the anionic polymer preferably employed in the developer solution is an acrylate/beheneth-25 methacrylate copolymer commercially available from Rohm and Haas, Philadelphia, Pa. under the name Aculyn® 28.
• Aculyn® 28 can be employed as the sole anionic copolymer in the developer solution of this invention, other additional anionic polymers, such as for example a copolymer of acrylic or methacrylic acid with their lower alkyl esters (Aculyn® 33) or nonionic thickeners, can also be added to the developer solution as long as their addition does not adversely effect the advantages of the use of Aculyn® 28 polymer's performance.
• the concentration of anionic polymer in the developer is from about 0.1% by weight to about 6% by weight, preferably about 0.5% to 4% by weight, most preferably about 1% to 3%, generally about 1.5% by weight.
• the developer solution will generally contain at least 70% by weight of water, preferably about 75 to 95% or more water.
• the developer and/or the lotion may also contain from 0 to about 0.2% by weight of a stabilizer such as phenacetin or ethylene diamine tetracetic acid (EDTA); from about 0 to 0.10%, preferably about 0.001% to 0.01% by weight of an antifoam agent such as simethicone; from about 0 to about 2%, preferably about 0.1% to 0.5% by weight pH buffer, such as for example edidronic acid; and from 0 to about 5%, preferably about 1.5% to 3% of any suitable conditioners, emulsifiers and/or surfactants, particularly conditioners, emulsifiers and surfactants such as PEG-50 tallow amide conditioner, Oleth-2, Oleth-5, Oleth-10 and oleyl alcohol emulsifiers, and C 12 -C 15 Pareth-3.
• a stabilizer such as phenacetin or ethylene diamine tetracetic acid (EDTA)
• EDTA ethylene diamine
• the viscosity of the developer as prepared for mixture with the lotion is from about 1 cps to about 5000 cps by weight, preferably 1 cps to 500 cps by weight.
• the pH of the developer is from about 2 to about 6, preferably 2.5 to 4.5, most preferably 2 to 3. Any of a variety of non-toxic acids or buffers may be employed to maintain pH. Etidronic acid and phosphoric acid are the most preferred.
• the lotion solution of this invention can be prepared in the following manner. Water is heated to about 50° C. to about 60° C. and the buffering agent added. Combine in a premix the conditioner and all emulsifiers and surfactants, and heat the premix to about 78° C. to about 80° C. Slowly add the heated premix to the heated buffered water solution and mix for approximately 20 minutes until a substantially uniform solution is obtained. Cool the solution with DI water and add the primary intermediate(s) and coupler(s), to the solution at a temperature below about 40° C. Then individually add the thickeners and antifoam agents to the solution and mix the resulting solution until essentially uniform.
• the lotion and developer are mixed just before application to the hair. On the hair, they form a stable gel with enough consistency and body and a viscosity of about 6,000 to about 30,0000 cps to remain on the hair during the complete coloring period without dripping or running.
• the resulting mixture exhibits the ability to ‘sheer down” during mixing to allow the developer/polymer solution to intermingle easily with the dye base components in the lotion, during which time the polymer is neutralized with a portion of the alkali, already present in the lotion composition, and thickening occurs.
• the primary intermediate and coupler, i.e. the dye precursors diffuse rapidly into the hair together with the oxidizing agent.
• the dyes form within the hair fiber and, since they are large molecules, remain in the hair so that the color change is permanent.
• the term “permanent” means that the dye does not readily wash out of the hair with ordinary shampoos.
• the color achieved with the products of this invention is so stable that it may survive as many as 20 shampoos without noticeable change.
• the use of the Schercoquat 21AP conditioner results in improved color uptake compared to previously used conditioners and permits a reduction in the total amount of active ingredients employed in the compositions as demonstrated in the Examples appearing herein after.
• the use of Schercoquat 21AP conditioning agent in the lotion formulation of the two-part hair dyeing compositions of this invention provides excellent wet feel and wet combing characteristics immediately after the dyeing mixture is rinsed from the dyed hair.
• compositions of this invention produce a hair dye system that has excellent stay-put and application properties, and provide the opportunity to more efficiently deliver conditioning materials resulting in improved product performance.
• composition is washed from the hair with an ordinary water rinse followed by a shampoo.
• compositions of this invention may be separately provided in a kit or package form ready for mixing by the user, either professional or personal, to initiate the dyeing process. It is preferred to mix them in a mixing vessel for subsequent application to the hair as the gel forms.
• the kit provided in accordance with this invention comprises those containers.
• a solid oxidant is employed, it may be convenient to package the developer in separate containers one with the oxidizing agent the other with the anionic polymer in water.
• the ingredients in the aqueous composition of the first container will include the dye precursors and the Schercoquat 21AP conditioning agent.
• the method of the invention comprises applying the dyeing mixture containing the Schercoquat conditioning agent to the hair to be colored and allowing it to remain in contact with the hair until the desired hair color has been attained after which the composition is removed from the hair as described above.
• Dye base lotions this invention was prepared from the following ingredients.
• FORMULATION A Ingredient Wt. % D.I. water 58.8420 Hexylene glycol 15.6000 C11-15 Pareth-9 4.5300 Monoethanolamine 4.5000 Dilinoleic acid 3.6000 Soytrimonium chloride and propylene glycol 3.4000 Schercoquat 21AP 2.0000 Oleamide MIPA 1.5000 Fragrance 1.0000 p-Aminophenol 0.6870 Oleth-10 0.6800 Erythorbic acid 0.5000 Citric acid 0.5000 Resorcinol 0.4950 m-Aminophenol 0.3820 p-Phenylenediamine 0.2920 1-Naphthol 0.1820 EDTA 0.1000 Oleth-2 0.1000 Sodium sulfite 0.1000 Cyclomethicone I 0.0100
• a further base lotion formulation of this invention was similarly formulated from the same ingredients as follows.
• FORMULATION E Ingredient Wt. % D.I. water 56.4420 Hexylene glycol 15.6000 C11-15 Pareth-9 4.5300 Monoethanolamine 4.5000 Dilinoleic acid 3.6000 Soytrimonium chloride and propylene glycol 6.8000 Schercoquat 21AP 2.0000 Oleamide MIPA 1.5000 Fragrance 1.0000 p-Aminophenol 0.6870 Oleth-10 0.6800 Erythorbic acid 0.5000 Citric acid 0.5000 Resorcinol 0.4950 m-Aminophenol 0.3820 p-Phenylenediamine 0.2920 1-Naphthol 0.1820 EDTA 0.1000 Oleth-2 0.1000 Sodium sulfite 0.1000 Cyclomethicone I 0.0100
• FORMULATION F Ingredient Wt. % D.I. water 58.4420 Hexylene glycol 15.6000 C11-15 Pareth-9 4.5300 Monoethanolamine 4.5000 Dilinoleic acid 3.6000 Soytrimonium chloride and propylene glycol 6.8000 Oleamide MIPA 1.5000 Fragrance 1.0000 p-Aminophenol 0.6870 Oleth-10 0.6800 Erythorbic acid 0.5000 Citric acid 0.5000 Resorcinol 0.4950 m-Aminophenol 0.3820 p-Phenylenediamine 0.2920 1-Naphthol 0.1820 EDTA 0.1000 Oleth-2 0.1000 Sodium sulfite 0.1000 Cyclomethicone I 0.0100
• developer solutions G and H prepared from the following ingredients.
• Solution G Solution H Ingredient Wt % D.I. water 82.9740 82.9740 Disodium EDTA 0.0400 0.0400 Etidronic acid 0.0800 0.8000 PEG-50 tallow amine 1.0000 1.0000 Oleth-2 1.0000 1.0000 Oleth-5 1.0000 1.0000 Oleyl alcohol 0.3000 0.3000 Stereth-21 2.0000 2.0000 Hydrogen peroxide 5.6000 2.0000 Aculyn ®-28 6.0000 — Simethicone 0.6000 0.6000 0.6000
• Developer solution G was mixed with each of the three lotions Formulation A, E and F and each of the resulting mixtures were each applied to bleached hair, pasmont hair and gray hair and color uptake measurements taken on a calorimeter.
• the shade used was a medium neutral blonde (7N).
• the Minolta 3700d spectrophotometer employed for the measurements 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.
• ⁇ E ⁇ square root ⁇ square root over (( L* f ⁇ L* i ) 2 +( a* f ⁇ a* i ) 2 +( b* f ⁇ b* i ) 2 ) ⁇
• Shercoquat 21AP conditioner can provide improved conditions effects without inhibiting the dyeing effect and also indicates that the same or improved results can be obtained with less active ingredients.
• Formulation A is able to obtain improved results over Formulation F even though the amount of soytrimonium chloride has been reduced from 6.8% to 3.4% and the total amount of Schercoquat 21AP and soytrimonium chloride is only 5.4%.
• Formulation E compared to Formulation F shows that the use of Shercoquat 21AP along with the soytrimonium chloride synergistically improves the performance of a formulation containing the soytrimonium chloride conditioner.
• Illustrative of typical lotion formulations of this invention containing dye components and Shercoquat 21AP conditioner are those which may have the following exemplary components in the indicated amounts, although it will be recognized that this is merely an exemplary formulation and formulation with other components are within the scope and spirit of this invention.
• Each solution i.e., dyeing lotion formulation and developer solution formulation is packaged in a separate container for use as a dyeing kit.
• a n desired thickening occurs to provide a non-drip dyeing product with excellent conditioning properties.

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