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WO2001085104A1 - Utilisation de melanines dans des compositions permettant de se demaquiller et/ou de nettoyer la peau et les membranes muqueuses - Google Patents
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WO2001085104A1 - Utilisation de melanines dans des compositions permettant de se demaquiller et/ou de nettoyer la peau et les membranes muqueuses - Google Patents

Utilisation de melanines dans des compositions permettant de se demaquiller et/ou de nettoyer la peau et les membranes muqueuses Download PDF

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WO2001085104A1
WO2001085104A1 PCT/IB2000/001615 IB0001615W WO0185104A1 WO 2001085104 A1 WO2001085104 A1 WO 2001085104A1 IB 0001615 W IB0001615 W IB 0001615W WO 0185104 A1 WO0185104 A1 WO 0185104A1
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use according
melanin
cleansing
skin
sodium
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Carlo Ghisalberti
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    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
    • A61K8/987—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of species other than mammals or birds
    • 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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/492—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 having condensed rings, e.g. indol
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the present invention relates to the use of melanins in compositions which are useful for removing make-up and or cleansing the skin and mucous membranes.
  • the present invention relates to the use of melanins and surfactants for the preparation of a composition for cleansing the skin and mucous membranes and/or for removing make-up, exerting a protective activity.
  • melanins and surfactants are complex three-dimensional biopolymers with several biological functions including: photoreceptor shielding, thermoregulation, photoprotection, camouflage, metal chelation and free radical scavenging.
  • melanins refers to a variety of highly irregular heteropolymers containing several structural moieties, such as free carboxy, amino, hydroxy, carbonyl, methoxy, biphenolic, indolic, quinoic groups and so on.
  • Melanins found increasing acceptance as ingredient in skin care compositions due to their photoprotective, anti-ageing, radical scavenging, chelating and tanning properties.
  • melanins So far, the use of melanins was limited to cream, lotion and other cosmetic composition which are applied to the skin with no subsequent wash out.
  • the only experience in toiletry products comprising melanins are shampoos, which are applied to the scalp and then rinsed with water to complete the cleansing of the hair.
  • compositions comprising chemically synthesized or biosynthetic water- soluble melanin and cationic surfactant for temporary haircolor are disclosed in US5,454,841.
  • melanins for trichologic applications, but the advantages of their use are limited to the keratinous fiber and the scalp.
  • the present invention relates to the use of melanins in compositions for cleansing the skin and mucous membranes and/or for removing make-up.
  • the present invention relates to the use of at least one melanin and at least one surfactant for the preparation of a composition for cleansing the skin and mucous membranes and/or for removing make-up.
  • compositions may either contains natural and/or synthetic melanins.
  • the former are extracted from natural sources such as animal tissues as in the case of “eumelanins”, “pheomelanins”, “seppiomelanins”, and the like or plant material containing melanins, as in the case of “phytomelanins", “micomelanins” and the like; the latter are obtained by synthesis by known enzymatic or chemical routes.
  • Example of suitable animal melanins are the eumelanins, brown-black nitrogenous pigments produced by the rearrangement and oxidation of L-dopa and its metabolites.
  • Further subtype of eumelanins includes the "oxymelanins” comprising tetrahydroxy indoles units within their polymeric structure; the "neuromelanin” from dopamine (which is produced L-dopa carboxylase) and its metabolite, 3.4-dihydroxycarboxylic acid, as well as by neural catecholamines and tetrahydroxyisoquinolines, e.g. occurring in the brain substantia nigra.
  • suitable animal melanins are the pheomelanins, yellow-reddish pigments containing both nitrogen and sulfur atoms, thus arising from the rearrangement and polymerization of cysteinyl-dopa, the condensation product of L-dopa and glutathione with further enzymatic hydrolysis
  • Suitable eumelanins and pheomelanins for the purpose of the present invention may be either extracted from animal tissues, such as octpus and squid inks; or synthesized from the typical eumelanin precursors by the treatment with the monomers with a known procedure, such as the alkaline oxidative polymerization for example in alkaline solution with injected air; the chemical oxidation, for examples with persulfates or hydrogen peroxydes; or the enzymatic synthesis with a polyphenoloxidase enzymes, such as tyrosinase oi ⁇ laccase.
  • a known procedure such as the alkaline oxidative polymerization for example in alkaline solution with injected air; the chemical oxidation, for examples with persulfates or hydrogen peroxydes; or the enzymatic synthesis with a polyphenoloxidase enzymes, such as tyrosinase oi ⁇ laccase.
  • Typical eumelanin precursors include L-dopa and its metabolites: dopa- semiquinone, dopaquinone, leucodopachrome, 5,6-dihydroxyindole-2-carboxylic acid (DFflCA), dopachrome, 5,6-dihydroxyindole (DHI), and indole-5,6-quinone, as well as 3,4-dihydroxyphenylethylamine (dopamine), 3,4-dihydroxyphenyl acetic acid (DHPA),
  • vegetal melanins examples include the “phytomelanins” resulting from the polymerization of plant polyphenols, and the “micomelanins", i.e. the broad photoabsorbing biopolymers containing naphthoic groups and typically found in fungi.
  • Suitable phytomelanins for the purpose of the present invention may be either extracted from plant material, as disclosed in WO00/09616, or more conveniently obtained by synthesis from vegetal monomers alone, in combination or in conjunction with eumelanin precursors, as disclosed in our copending application PCT/D300/01276.
  • Typical phytomelanin precursors include flavonoids such as quercetin, fisetin, fustin, luteolin, OPC, catechin, epicatechin, gallocatechin (GC), gallocatechin gallate (GCG), epigallocatechin (EGC), epigallocatechin gallate (EGCG), myricetin, dihydroquercetin, cyanidin, delphinidin; and phytoalexins such as hydroxytyrosol, protocathechuic acid, protocathechuic aldehyde, gallic acid, tanriic acid, pyrocatechin and pyrogallol.
  • flavonoids such as quercetin, fisetin, fustin, luteolin, OPC, catechin, epicatechin, gallocatechin (GC), gallocatechin gallate (GCG), epigallocatechin (EGC), epigallocatechin gallate (EGCG), myricetin, dihydroquercetin, cyanidin, delphin
  • Suitable micomelanins for the purpose of the present invention may be either extracted from fungi, or more conveniently obtained by chemical or enzymatic synthesis from dihydroxynaftols alone, in combination or in conjunction with eumelanin or phytomelanin precursors, as disclosed in our pending application MI2000A1513.
  • micomelanin precursors include dihydroxynaphthols (DHN), such as 1,8-DHN, 1,5-DHN, 1,6-DHN, 2,7-DHN, 2,3-DHN, 1,4-DHN and the corresponding naphthoquinones as disclosed in our pending application MI2000A1513.
  • the autoxidative polymerization synthesis of melanins is generally carried out by bubbling air or oxygen through an alkaline aqueous solution of the monomers at pH 10 or above.
  • the alkaline aqueous solution may comprise catalytic amounts of pro-oxidant metals, such as C ⁇ X, Fe ⁇ , Ni ++ , or Co ++ solutions, for example at 5 to 20 mM concentration.
  • the chemical polymerization of the monomers is generally carried out in aqueous solution in presence of at least one equivalent of one or more chemical oxidizing agents, such as hydrogen peroxide, hydrogen iodide, ammonium persulfate, potassium permanganate, or magnesium perchlorate.
  • chemical oxidizing agents such as hydrogen peroxide, hydrogen iodide, ammonium persulfate, potassium permanganate, or magnesium perchlorate.
  • the enzymatic synthesis of the monomers of melanins is generally carried out in a buffered solution at pH 4-9, preferably pH 6.5-8, in presence of one or more melanin-forming enzymes, such as tyrosinases, polyphenoloxidases (catechol oxidases), phenolases (phenoloxidases), peroxidases, laccases or lypoxygenases.
  • melanin-forming enzymes such as tyrosinases, polyphenoloxidases (catechol oxidases), phenolases (phenoloxidases), peroxidases, laccases or lypoxygenases.
  • Suitable enzymes for the synthesis of synthetic vegetal melanins of the present invention may be obtained from several melanin-producing biological cells or tissues, such as: (1) extracts of animal skins, e.g. horses, cattle, sheep, pigs, or any other such mammalian source; extracts of skins offish, amphibia, reptiles, birds;
  • culture media of any organisms or cells which secrete enzymes for producing soluble melanins -such organisms or cells may or may not express cloned genes for the enzymes.
  • the melanins which are suitable for the purposes of the present invention may therefore have polyindolic, polyphenolic or polynaphthoic structures, regardeless if obtained by extraction or synthetic methods.
  • surfactants designates in the present invention compounds acting on the lipid-water-lipid interface by lowering the surface tension, each said compound having its own hydrophilic-lipophilic balance (HLB), also known as surface-active agents.
  • HLB hydrophilic-lipophilic balance
  • Suitable surfactants to be used in the compositions according to our invention may be cationic, anionic, amphoteric (zwitterionic), polar nonionic, nonionic substance and mixture thereof.
  • cationic surfactants to the compositions as the melanins generally comprise anionic moieties within their structure, therefore, surfactants containing a positive charge within the molecular structure, either as cationic, amphoteric or partially polarized dative bound may able to compensate the anionic moyeties present in the melanin polymeric structure.
  • anionic and nonionic surfactants stabilize melanin in the compositions useful for skin and mucosae membrane cleansing, which may happens either due to the formation of electrostatic bounds between the molecular dipoles or to the formation of ion pairs with the nitrogen atom, as occurs for example in the case of the polyindolic melanins.
  • Suitable cationic surfactants include those compounds containing an organic hydrophobic group generally containing 8 to 26 carbon atoms and preferably 10 to 18 carbon atoms in their molecular structure, and at least one cationic water- solubilizing group, e.g. non-quaternary nitrogen, quaternary ammonium or quaternary phosphonium group.
  • Suitable synthetic cationic surfactants are C12-C22 alkyl primary amines; C12-22 alkyl diamines, e.g. N-2-aminoethyl stearyl amine and N-2- aminoethyl myristyl amine; amide-linked amines such as those with C8-20 alkylamido-ethylediamine, e.g.
  • the alkyl group may contain intermediate amido bonds not substantially affecting the hydrophobic character of the group, e.g., stearyl amido propyl quaternary ammonium chloride, e.g.
  • ethyldimethyl- stearyl ammonium chloride benzyl-dimethyl-stearyl ammonium chloride, trimethyl-stearyl ammonium chloride, trimethyl-cetyl ammonium bromide, dimethyl-ethyl-lauryl ammonium chloride, dimethyl-propyl-myristyl ammonium chloride, or methansulfate or acetates thereof.
  • cationic surfactants are represented by ricinoleamidopropyl ethyldimo ium ethosulfate; quatemium 75, isostearamidopropyl ethyldimonium ethosulfate and linoleamidopropyl PG-dimonium chloride phosphate.
  • Suitable anionic surfactants include those compounds containing an organic hydrophobic group containing generally. 8 to 26 carbon atoms and preferably 10 to 18 carbon atoms in their molecular structure, and at least one water-solubilizing group selected from the group consisting of sulfonate, sulfate, carboxylate, phosphonate and phosphate.
  • the compounds formed by including one to about 40 moles of ethylene oxide in the foregoing esters are also satisfactory.
  • anionic surfactants are water-soluble alkyl or alkyl aryl sulfates or sulfonates having from about 8 to about 22 carbons, preferably from about 12 to about 18 carbons in the alkyl radical, which may be a linear or branched chain.
  • Said surfactants also include such classes of compounds which are ethoxylated with from 1 to 5 moles, preferably 1 to 3 moles, of ethylene oxide (EO) per molecule.
  • the sulfate or sulfonate group is typically base-neutralized to provide an alkali metal salt, especially a sodium, potassium, ammonium, or mono-, di- or triethanolamine.
  • Illustrative anionic surfactants of the above-named classes include, but are not limited to: sodium cetyl sulfate; sodium myristyl sulfate; sodium lauryl sulfate; sodium tallow sulfate; sodium decyl sulfate; sodium decylbenzene sulfonate; sodium tridecylbenzene sulfonate; sodium C14-C16 olefin sulfonate; sodium C12-C15 alcohol sulfate; sodium lauryl ether sulfate; sodium myristyl ether sulfate; sodium polyoxyethylene (5 moles EO) lauryl ether sulfate; sodium polyoxyethylene (12 moles EO) lauryl ether sulfate; sodium nonylphenyl ether sulfate; sodium polyoxyethylene (1 to 4 moles EO); C12-C15 alkyl ether sulfate and sodium lauryl
  • Suitable anionic surfactants include sulfosuccinates, e.g., sodium dioctyl sulfosuccinate; disodium lauryl sulfosuccinate and the disodium polyoxyethylene (1 to 4 moles EO) lauryl alcohol half ester of sulfosuccinic acid; sulfated monoglycerides, e.g., sodium cocomonoglyceride sulfate; sarcosinates, e.g., sodium cocoyl sarcosinate and sodium lauroyl sarcosinate; esters of isethionic acid, e.g., sodium cocoyl isethionate and sodium lauroyl isethionate; taurates, e.g., sodium N-methyl-N-cocoyl taurate and sodium N-methyl-N-oleoyl taurate.
  • sulfosuccinates e.g., sodium dioct
  • anionic surfactants which fall within the definition of the anionic surfactants include the water-soluble soaps, i.e. the sodium, ammonium, and alkanolammonium salts, of higher fatty acids or resin salts containing about 8 to 20 carbon atoms, preferably 10 to 18 carbon atoms.
  • Suitable fatty acid salts can be obtained from oils and waxes of animal or vegetable origin, e.g. tallow, grease, coconut oil, tall oil and mixtures thereof. Particularly useful are the sodium and potassium salts of the fatty acid mixtures derived from coconut oil and tallow, e g , sodium coconut soap and potassium tallow soap.
  • Suitable anionic surfactants also include C8-C18 acyl sarcosinates (e.g. sodium lauroyl sarcosinate), sodium and potassium salts of the reaction product of higher fatty acids containing 8-18 carbon atoms esterified with isethionic acid, and sodium and potassium salts of the C8 -C18 acyl N-methyl taurides, e. g., sodium cocoyl methyl taurate and potassium stearoyl methyl taurate.
  • C8-C18 acyl sarcosinates e.g. sodium lauroyl sarcosinate
  • sodium and potassium salts of the reaction product of higher fatty acids containing 8-18 carbon atoms esterified with isethionic acid e.g., sodium cocoyl methyl taurate and potassium stearoyl methyl taurate.
  • Fatty alkyl sulfosuccinates can be employed where the fatty alkyl group contains from 8 to 22 carbons atoms.
  • surfactants are those of the following formula (A) to (D):
  • A R 2 -OCH 2 -(CH 2 )a-CO-CH(SO 3 X)CH 2 -COORl ;
  • B R 1 -CONH(CH 2 )b-OOCCH(SO 3 X)CH 2 -COOX;
  • C R ⁇ NH-CO-C ⁇ SO ⁇ CHsCOOX (D) wherein R 1 is an alkyl group having from 8 to 22 carbon atoms, R 2 is an alkyl group having from 4 to 16 carbon atoms;
  • X is an anion such as an alkali metal, such as sodium or potassium, sulfate, methylsulfate, ethylsulfate, ammonium; an amine of from 1 to about 9 carbon atoms, such as methylamine, ethylamine, diethylamine and tri(n- propyl)amine;
  • sulfosuccinates of formula (A) are disodium lauryl sulfosuccinate, disodium laureth-3 sulfosuccinate, disodium isodecyl sulfosuccinate, disodium deceth-6 sulfosuccinate, disodium stearyl sulfosuccinate, disodium cetearyl sulfosuccinate, disodium laureth-5 sulfosuccinate, and disodium laureth sulfosuccinate and dipotassium laureth sulfosuccinate wherein the average number of ethoxy groups present is between 1 and 4.
  • Disodium laureth-3 sulfosuccinate and disodium laueth-5 sulfosuccinate are particularly preferred.
  • Examples of compounds of formula (B) are dioctyl sodium sulfosuccinate, dipalmityl sodium sulfosuccinate, and dilauryl potassium sulfosuccinate. Dioctyl sodium sulfosuccinate is particularly preferred.
  • Examples of compounds of formula (C) are disodium lauramido MEA sulfosuccinate; disodium cocamido MTPA-sulfosuccinate, disodium lauramido MEA- sulfosuccinate, disodium myristamido MEA-sulfosuccinate, disodium oleamido MEA-sulfosuccinate, disodium oleamido MIPA- sulfosuccinate, disodium stearamido MEA-sulfosuccinate, disodium undecylenamido MEA- sulfosuccinate, and dipotassium cocamido M PA- sulfosuccinate.
  • Examples of compounds of formula (D) are disodium lauryl sulfosuccinamate, disodium oleyl sulfosuccinamate and tetrasodium dicarboxyethyl stearyl sulfosuccinamate.
  • N-acyl amino acid salts more preferably of aspartic acid or glutamic acid, or salts of N-acyl derivatives of hydrolyzed proteins having average weight of about 2.500 daltons, wherein the acyl portion is derived from a carboxylic acid having from 8 to 22 carbon atoms per molecule, can be used.
  • Examples of such salts are sodium lauroyl glutamate, monotriethanolamine
  • N-cocoyl-L-glutamate sodium N-myristoyl-L-glutamate, potassium decoyl glutamate, sodium cocoyl glutamate, sodium stearoyl glutamate, potassium lauroyl aspartate, sodium stearoyl aspartate, sodium lauroyl aspartate, TEA-lauroyl glutamate, lauroyl-L-lysine, 2- octyldodecyl diester of N-lauroyl-L-glutamic acid, and potassium capryloyl aspartate.
  • Anionic phosphate surfactants in which the anionic solubilizing group is an oxyacid of phosphorous are also useful in the present compositions.
  • phosphates are sodium ceteareth-2 phosphate, DEA-oleth-1 phosphate, DEA-oleth-3 phosphate, sodium laureth-8 phosphate, sodium di(oleth-2) phosphate, sodium laureth-4 phosphate, potassium lauryl phosphate and sodium deceth-2 phosphate.
  • Suitable amphoteric surfactants include those compounds containing an organic hydrophobic group containing generally 8 to 26 carbon atoms and preferably 10 to 18 carbon atoms in their molecular structure, and at least one water-solubilizing group comprising a positively charged (cationic) and a negatively charged (anionic) moieties.
  • Suitable synthetic amphoteric surfactants include i.a. betaines and sulfobetaines.
  • betaines that are useful herein include the high alkyl betaines, such as cocodimethyl carboxymethyl betaine, lauryl dimethyl carboxymethyl betaine, lauryl dimethyl alpha-carboxyethyl betaine, cetyl dimethyl carboxymethyl betaine, lauryl bis-(2-hydroxyethyl)carboxymethyl betaine, stearyl bis-(2- hydroxypropyl)carboxymethyl betaine, oleyl dimethyl gamma carboxypropyl betaine, lauryl bis-(2-hydroxypropyl)alpha-carboxyethyl betaine, and the like.
  • sulfobetaines are cocodimethylsulfopropyl betaine, stearyl dimethylsulfopropyl betaine, lauryl dimethylsulfoethyl betaine, lauryl bis-(2- hydroxyethyl)sulfopropyl betaine, and the like.
  • Amido betaines and amidosulfobetaines, especially those wherein the R 1 -CONH(CHa) 3 radical is attached to the nitrogen atom of the betaine, are useful in the present invention, for example, cocamidopropyl betaine, wherein R 1 is as previously defined.
  • amphoteric surfactants thus containing at least one cationic group, e.g. non-quaternary nitrogen, quaternary ammonium or quaternary phosphonium group, at least one alkyl group of 8-18 carbon atoms and may be linear chain or branched and the specific cationic atom may be part of an heterocyclic ring.
  • at least one cationic group e.g. non-quaternary nitrogen, quaternary ammonium or quaternary phosphonium group
  • alkyl group of 8-18 carbon atoms may be linear chain or branched and the specific cationic atom may be part of an heterocyclic ring.
  • Example of a natural mixture of amphoteric and anionic surfactants are lecithins, i.e. natural low-irritating and physiological substance with a surface-active behaviour which can be obtained from both animal and vegetable tissues as well as from egg yolks.
  • These natural or fractionated phospholipids may include variable proportion of phosphatides, for example phosphatidylcholine, phosphatidic acid, phosphatidylethanolamine, phosphatydylserine, phosphatidylinositol, phosphatidyl glycerol, and the corresponding lysophosphatides, as well as sphingomyelins, cardiolipins, plasmalogens and cerebrosides.
  • Suitable polar nonionic surfactants include those compounds containing an organic hydrophobic group generally containing 8 to 26 carbon atoms and preferably 10 to 18 carbon atoms in their molecular structure, and at least one water-solubilizing group containing a semi-polar bond directly between two atoms, for example, N ⁇ O, P->O, and S- ⁇ O where no charge separation is actually displayed within the molecule.
  • polar nonionic surfactants include trisubstituted aliphatic amine oxides (R3N- O), pyridine, amide, and so on, with one C8-22 alkyl N-bonded group and two Cl-3 alkyl N-bonded groups, including alkyl groups bearing inert substituents, such as phenyl groups, an alkyl, alkenyl, or monohydroxyalkyl radical having about 10 to 16 carbon atoms.
  • surfactant with aliphatic amine oxides are cocamine oxide, lauramine oxide, myristamine oxide, stearamine oxide, laur(diethyl)amine oxide and behen(dimethyl)amine oxide, coco-morpholine oxide, N-lauryl-morpholine oxide, N- stearyl-morpholine oxide, cocamidopropylamine oxide, lauramidopropylamine oxide, caprylamidopropyl(diethyl) amine oxide, capramidoethyl(dimethyl)amine oxide, lauramidopropyl(diethyl)amine oxide, stearamidopropylamine oxide, and behenylamidopropyl(dimethyl)amine oxide.
  • polar nonionic surfactants are the open-chain aliphatic phosphine oxides (R3P- O) wherein the alkyl groups are similar to those defined in the case of the amine oxides.
  • Suitable nonionic surfactants include those compounds produced by the condensation of hydrophilic alkylene oxide groups with an organic hydrophobic compound having a carboxy, hydroxy, amido, or amino group with a free hydrogen.
  • the most common polyalkylenes are the ethylene oxide (EO) or propylene oxide (PO) condensation products, homopolymers, as well as random or block co- polymers, whose chain lenght is adjustable to afford the required balance between the hydrophobic and hydrophilic characteristic.
  • the nonionic surfactants may have a poly-EO chain with about 5 to 30 EO moles condensate to one linear or branched C6-12 alkyl phenol, e.g., nonyl phenol-9- EO moles, dodecyl phenol-15-EO and dinonyl phenol-15-EO. Condensation products of the corresponding alkyl thiophenols with 5 to 30 EO moles are also suitable.
  • nonionics surfactants are the condensation products of a linear or branched C8-18 higher alcohol with about 5 to 30 EO moles, e.g., lauryl-myristyl alcohol- 16-EO.
  • nonionics surfactants may be those derived by the condensation of EO with the product resulting from the reaction of PO and ethylene diamine.
  • the molecular weight ranges from 500 to 4. 500 or more.
  • nonionics surfactants that are especially contemplated are the highly eudermic saccharide-type surfactants, thus having a linear or branched C8-18 alkyl, alkenyl or alkylphenyl group linked to a poly-EO or poly-PO with 1 to 10 alkoxy units which finally linked to a C5-6 reduced sugar.
  • nonionic amphiphilic compounds can be those from the class of alkyl polyglycerides such as polyglyceryl-6 distearate, polyglyceryl-3 hydroxy lauryl ether and polyglyceryl-2 lanolin ether.
  • Suitable nonionics surfactants include the poly-EO octyl and nonyl phenyl ethers with about 6 EO moles, preferably about 6 to 15 EO moles, block copolymers of EO and PO, and polyEO sorbitan monolaurates and monostearates, generally designated as Tween surfactants. It is understood that the above mentioned classes of surfactants are exemplary only and should not be regarded as limiting.
  • melanins are formulated in rinseable (also called “rinse-off") compositions, advantageously in combination with a surfactant.
  • Said compositions are usually prepared according to the well known techniques.
  • the solubilization of melanin is accomplished very simply by adding melanins, in solution or in solid form, to one or more of the above surfactants to with agitation.
  • the compositions may be stirred for a period of minutes to hours after the addition is complete.
  • the stabilization of the synthetic melanin obtained by alkaline polymerization generally occur very rapidly, whilst for less soluble melanins such as the natural and enzymatic melanin in solid form, a stabilized suspension is obtained by a high stirring with a concentrated solution of the surfactant for an extended period of time.
  • the stabilized melanin suspension may be used as such, as skin cleansing composition, if a sufficient amount of the above surfactants are present to impart cleansing properties to the composition.
  • melanins are used in amounts ranging from about 0.0001% to 5% by weight for based on the total weight of the composition, preferably from 0.001% to 0.5%.
  • melanins are used in amounts from about 0.001% to 0.5% for transparent solid or liquid compositions and from 0,01 to 1% for opaque solid or liquid/fluid compositions.
  • Surfactants are present in sufficient quantity to obtain the purpose of skin cleansing. Suitable surfactants for use in the compositions according to the present invention are those usually incorporated into skin cleansing products.
  • the cleansing compositions comprising melanins may be prepared in a variety of solid, semi-fluid and liquid formulations including solid and fluid soaps, syndeth, detergent lotions, bath gels, cleaning emulsions, bath and shower creams or gels, pumps, sprays, aerosols, mousses/foams, solutions and the like.
  • Aqueous compositions may contain surfactants in amounts ranging from about 5% to 90%.
  • surfactants are contained from about 50% to 90%, by weight, whilst for fluid and liquid detergents the surfactants are contained from about 5% to 50%, by weight based upon the total weight of the cleansing composition.
  • compositions according to the present invention may also contain additive ingredients which improve, for example, the quality and elegance of the final products, as set forth below. These additional components are present at levels which are effective to provide their intended functions.
  • Foam builders or foam stabilizers i.e. materials which increase the quality, volume and stability of the lather can also be used. They also enhance viscosity Preferred foam builders are fatty acid alkanolamides, such as lauroyl diethanolamide, lauroyl monoethanolamide and coconut monoethanolamide.
  • Other foam builders are "super" amides, e.g. super amide B-5, fatty alcohols, sarcosinates, phosphates and dodecylbenzene sulfonates.
  • the foam builders are typically present in an amount of from about 0.1% to 10%, preferably, from about 0.5% to about 5%.
  • Opacifying agents can be used, for example, in cream compositions. Suitable opacifying agents are the higher alcohols, such as stearyl and cetyl alcohol, and the higher acids, such as behenic acid. The glycol mono- and di-stearates are also effective opacifiers. Alkaline earth metal fatty acid soaps, such as calcium stearate and magnesium stearate, are also suitable. Magnesium silicates are also useful for this purpose. Opacifying agents are typically present in an amount of from about 0.1% to about 10%), preferably, from about 0.5% to about 5%. Viscosity-control agents are often useful to stably regulate the viscosity of the ingredients of a fluid composition.
  • Suitable viscosity-control agents are lower alcohols, e.g., isopropyl glycol and butyl alcohol; and lower glycols, e.g., di ethylene glycol, terpineol and diethyl carbitol. These agents are typically present in an amount of from about 0.1% to about 5%, preferably, from about 0.5% to about 2.5%. Sequestering agents are useful to prevent the formation of a lime soap film when cleansed skin is rinsed with hard water. Suitable materials are ethylenediaminetetraacetic acid (EDTA), citric acid, sodium xylene sulfonate and sodium naphthalene sulfonate. Sequestering agents are typically present in an amount of from about 0.01% to about 5%, preferably, from about 0.1% to about 1%. Thickening agents also increase the viscosity of a fluid toiletry product.
  • EDTA ethylenediaminetetraacetic acid
  • Sequestering agents are typically present in an amount of
  • Suitable materials are natural gums such as tragacanth, xanthan, acacia and locus bean; and synthetic gums such as hydroxypropylcellulose and methyl cellulose.
  • Polyvinyl alcohols can also be used.
  • Alkanolamides e. g., cocamide MEA and lauramide DEA
  • "super" amides and the glycol or glycerol stearates may also be used.
  • Thickening agents are present in a sufficient amount to provide the desired viscosity, typically from about 0.1% to about 10%, preferably, from about 0.1% to about 10%.
  • Preservatives are typically present to prevent degradation from bacterial and mold action.
  • 2-phenoxyethanol and mixtures thereof are particularly preferred. They are preferably present in the compositions an amount of from about 0.01 to about 1%.
  • antioxidants such as sodium sulfite
  • propellants such as peppermint, styrene
  • suspending agents such as peppermint, styrene
  • fragrances and herbals such as peppermint, styrene
  • coloring agents such as styrene, styrene, styrene, styrene, styrene, styrene, sulfate, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sulfate, stylitol, stylitol, stylitol, stylitol, stylitol, stylitol, stylitol, stylitol, stylitol, stylitol, sulfate, stylitol,
  • compositions include fillers, clays, lipophilic lower alkoxypolypropylene glycols having a molecular wight in the range of 1.000 to 2.500 such as butoxy polyoxypropylene glycols having a molecular weight of about 1.700; hydrophobic mixed polyethylene polyalkylene (C3 - C4)glycol condensates of butanol having a molecular weight of about 400 to 4000 and containing from 35 to 65 percent by weight of polyethylene glycol; polyhydric alcohols containing 2 to 3 carbon atoms such as glycerol and propylene glycol; and gums, such as gum tragacanth.
  • fillers clays, lipophilic lower alkoxypolypropylene glycols having a molecular wight in the range of 1.000 to 2.500 such as butoxy polyoxypropylene glycols having a molecular weight of about 1.700; hydrophobic mixed polyethylene polyalkylene (C3 - C4)glycol condensates of
  • Water is present in the compositions at about 30% to about 99%, preferably, about 50%) to about 95%o, advantageouly about 70% to about 90%, by weight, based on the total weight of the composition. It is understood that, unless otherwise specified, all reagents and components of the compositions of the present invention are present in % by weight, based on the total weight of the composition. Also, anhydrous compositions such as those based on glycerin or glycerides can be used, as well as fish-liver oils, optionally diluted with vegetable oil.
  • the addition of melanin to produce the compositions of the present invention may be performed at any moment during the manufacturing of the detergents, preferably after the addition of surfactants, or along with lime in the particular case of the soaps obtained by direct hydrolysis of triglicerides.
  • the present invention relates to the. use of a composition comprising melanins and optionally one or more surfactants for the cleansing of the skin and mucous membranes and/or the removing make-up.
  • the present invention relates to a method for' the cleansing of the skin and mucous membranes and/or the removing make-up which comprises applying a rinse-off composition comprising at least one melanin and optionally one or more surfactants.
  • the cleansing of the skin and mucous membranes and/or the removing makeup according to the present invention allow to protect the skin and mucosae defending dermis against environmental oxidative stress; more particularly, the use of melanins according to the invention allows to decrease the detrimental effect of the normal skin and mucosae cleansing compositions.
  • the perlescent amber creams contain the following ingredients (% by weight):
  • Disodium Laureth Sulfosuccinate (sol 37%) 6.0 6.0 6.0
  • Phase B Cocamidopropyl Betaine (35%) 8.0 8.0 8.0 Acqua, Sodium Laureth Sulphate, Glycerol
  • the ingredients of phase A and phase B are added according the aforementioned list in descending order.
  • the composition have pH 6.0-7.0; with viscosity of about 4.000 mPa.s. for Example 1. of 6.000 mPa.s. for Example 2. and of 8.000 mPa.s. for Example 3.
  • the creamy and perlescent brown creams contain the following ingredients (% by weight):
  • Phase A Xanthan gum 1.0 1.0 1.0 Disodium Laureth Sulfosuccinate (sol 37%) 10.0 10.0 10.0
  • Disodium Cocoamphodiacetate (sol 30%) 12.0 12.0 12.0 Sodium Laureth Sulphate (27%) 15.0 15.0 15.0
  • phase A and phase B are then added under stirring.
  • the composition of Examples 4-6 have pH 6.0-7.0 and viscosity from 6.000 to 8.000 mPa.s. Examples 7-9 - Bath showers
  • the amber compositions contain the following ingredients (% by weight): INCI Name Ex. 7 Ex.8 Ex. 9
  • Glyceryl Laurate 1.0 - - Glyceryl Oleate - 1.0 - Glyceryl Linoleate - - 1.0 Polyquaternarium-39 (10%) 1.0 1.0 1.0 1.0 Phytomelaninl0% solution, synthetic (1) 0.07 0.07 0.07
  • Aqua 42.93 42.93 42.93 c Obtained by air injection onto a solution of grape seed Proanthocyanosides 5% and L-dopa 5% w/v in NaOH IN for 24h.
  • Phase A and phase B are directly blended in a mixer, apart glyceryl laurate which is previously melted at 45-50° C before mixing, whils there is no need of heating for glyceryl oleate and linoleate.
  • the compositions have pH 5.5-6.5 and viscosity of 4.500-5.500 mPa.s.
  • a bath-shower with fast rinsing is obtained in Example 7; with more pronounced emoUience in Example 8; and with a superfatty effect in Example 9.
  • Examples 10-12 - Bath oils The oily compositions contain the following ingredients (%> by weight):
  • the products are obtained by direct mixing the ingredients.
  • the compositions have pH 6.0-7.0 and viscosity of 350-500 mPa.s..
  • the bath oil have a different color tones in the Examples 10-12 according to the selected phytomelanin.
  • Fluid soaps for mucous membranes e.g. for personal care
  • the fluid soaps contain the following ingredients (% by weight):
  • Phase A Disodium Laureth Sulfosuccinate (37%) 25.0 25.0 25.0 Sodium Cocoamphoacetate (30%) 15.0 15.0 15.0
  • the product are prepared by mixing the ingredients.
  • the compositions have pH 5.0-6.0; with viscosity of about 2.000 mPa.s. for Example 13, of about 3.500 for Example 14; and of about 4.500 mPa.s. for Example 15.
  • the transparent ambered fluid compositions contain the following ingredients (% by weight):
  • Disodium Laureth Sulfosuccinate (37%) 15.0 15.0 15.0
  • Phase A and phase B are mixed untill a homogenous blend is obtained.
  • the compositions have pH 6.0-7.0 and viscosity comprised between 800 and 1.000 mPa.s. Examples 19-21 - Deep conditioning bath
  • the cellulose is dispersed in water under stirring untill full swelling, then phase A is added.
  • the glucamate is melted at 50°C and additioned to the mixture, thereby heated at the same temperature, then phase B is added.
  • the compositions have pH 6-7 and viscosity comprised between 1.000 and 5.000 mPa.s.
  • Examples 22-24 - Handcleansing gels These soft gels contain the following ingredients (% by weight):
  • Phase A is heated at 50°C mixed and then with phase B.
  • the compositions have pH 6-7 and viscosity comprised between 8.000 e 10.000 mPa.s. Examples 25-27 - Face cleansing
  • These opaque fluid detergents contain the following ingredients (% by weight): ⁇
  • the acrylic polymer is dispersed in water, heated to 35-40 °C, then isopropyl palmitate is added thereby under turbomixing. Phase B are then added and stirred untill an emulsioned homogeneous mass is obtained.
  • the compositions have pH 6.0- 7.0 and viscosity comprised between 3.000 and 4.500 mPa.s, with darker color tones moving from Examples 25 to 27. Examples 28-30 - Natural soaps
  • phase A The components of phase A are blended under moderate heating untile a melted mass is obtained, then the premixed phase B is added while keeping the mixture under slow stirring at 35-45° C for about 3 hours. Finally the product is traced at room temperature for 2-3 weeks.
  • phase A The components of phase A are blended under moderate heating untile a melted mass is obtained, then the premixed phase B is added while keeping the mixture under slow stirring at 35-45° C for about 3 hours. Finally the product is traced at room temperature for 2-3 weeks.
  • the saponification is carried out as in Examples 28-30 except that the temperature is 50-55° C, then the components of phase C are added in the following sequence: sucrose solubilized in water, ethanol and then glycerin.
  • the mixture is heaten to 70° C untill the mixture strart solidifying.
  • the mass is then cooled at -20°C for about 3 hours and then the soap is let trace at room temperature for about 2 weeks.

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Abstract

L'invention concerne l'utilisation de mélanines, de préférence associées à des tensioactifs, pour préparer une composition de nettoyage de la peau et des membranes muqueuses et/ou pour se démaquiller, tout en exerçant une activité protectrice.
PCT/IB2000/001615 2000-05-08 2000-11-07 Utilisation de melanines dans des compositions permettant de se demaquiller et/ou de nettoyer la peau et les membranes muqueuses Ceased WO2001085104A1 (fr)

Priority Applications (1)

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AU2001211673A AU2001211673A1 (en) 2000-05-08 2000-11-07 Use of melanins in compositions for removing make-up from and/or cleansing the skin and mucous membranes

Applications Claiming Priority (2)

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IT2000MI000994A IT1318501B1 (it) 2000-05-08 2000-05-08 Detergenti cutanei contenenti melanine.
ITMI2000A000994 2000-05-08

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1800649B2 (fr) † 2005-12-21 2012-10-10 L'Oréal Composition cosmétique à effet volumateur
WO2012136782A1 (fr) * 2011-04-08 2012-10-11 L'oreal Procédé de teinture ou de conditionnement de fibres kératiniques à l'aide d'un pigment résultant d'un dérivé de 1,8-dihydroxynaphtalène, composition contenant le pigment et pigment
FR2973688A1 (fr) * 2011-04-08 2012-10-12 Oreal Procede de maquillage de la peau, des levres ou des ongles comprenant une composition cosmetique comportant au moins un pigment susceptible d'etre obtenu par reaction chimique d'au moins un derive de 1,8-dihyroxynaphtalene et d'au moins un agent oxydant chimique
WO2017212500A1 (fr) * 2016-06-09 2017-12-14 Council Of Scientific & Industrial Research Procédé de préparation d'une solution homogène d'un polymère et de mélanine
US10220223B2 (en) 2005-12-21 2019-03-05 L'oreal Cosmetic composition with a volumizing effect
US12083196B2 (en) 2020-11-09 2024-09-10 Ecolab Usa Inc. Personal cleansing compositions with surfactants for increased foam performance

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3987202A (en) * 1974-05-30 1976-10-19 Okun Milton R Method of treating psoriasis
WO1999011223A2 (fr) * 1997-08-29 1999-03-11 Unilever Plc Compositions de traitement capillaire
US5925363A (en) * 1993-07-02 1999-07-20 L'oreal Cosmetic composition containing, in combination, a superoxide-dismutase and a melanin pigment

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3987202A (en) * 1974-05-30 1976-10-19 Okun Milton R Method of treating psoriasis
US5925363A (en) * 1993-07-02 1999-07-20 L'oreal Cosmetic composition containing, in combination, a superoxide-dismutase and a melanin pigment
WO1999011223A2 (fr) * 1997-08-29 1999-03-11 Unilever Plc Compositions de traitement capillaire

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1800649B2 (fr) † 2005-12-21 2012-10-10 L'Oréal Composition cosmétique à effet volumateur
US10220223B2 (en) 2005-12-21 2019-03-05 L'oreal Cosmetic composition with a volumizing effect
WO2012136782A1 (fr) * 2011-04-08 2012-10-11 L'oreal Procédé de teinture ou de conditionnement de fibres kératiniques à l'aide d'un pigment résultant d'un dérivé de 1,8-dihydroxynaphtalène, composition contenant le pigment et pigment
FR2973688A1 (fr) * 2011-04-08 2012-10-12 Oreal Procede de maquillage de la peau, des levres ou des ongles comprenant une composition cosmetique comportant au moins un pigment susceptible d'etre obtenu par reaction chimique d'au moins un derive de 1,8-dihyroxynaphtalene et d'au moins un agent oxydant chimique
FR2973689A1 (fr) * 2011-04-08 2012-10-12 Oreal Procede de coloration ou de maquillage des fibres keratiniques a partir de pigment issu de derive de 1,8-dihyroxynaphtalene, composition contenant le pigment et le pigment
WO2017212500A1 (fr) * 2016-06-09 2017-12-14 Council Of Scientific & Industrial Research Procédé de préparation d'une solution homogène d'un polymère et de mélanine
US11109589B2 (en) 2016-06-09 2021-09-07 Council Of Scientific And Industrial Research Process for preparing a homogeneous solution of a polymer and melanin
US12083196B2 (en) 2020-11-09 2024-09-10 Ecolab Usa Inc. Personal cleansing compositions with surfactants for increased foam performance

Also Published As

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ITMI20000994A1 (it) 2001-11-08
IT1318501B1 (it) 2003-08-25
ITMI20000994A0 (it) 2000-05-08
AU2001211673A1 (en) 2001-11-20

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