WO2011047421A1 - Composition antifongique et procédé de traitement de la dermatite - Google Patents

Composition antifongique et procédé de traitement de la dermatite Download PDF

Info

Publication number
WO2011047421A1
WO2011047421A1 PCT/AU2010/001387 AU2010001387W WO2011047421A1 WO 2011047421 A1 WO2011047421 A1 WO 2011047421A1 AU 2010001387 W AU2010001387 W AU 2010001387W WO 2011047421 A1 WO2011047421 A1 WO 2011047421A1
Authority
WO
WIPO (PCT)
Prior art keywords
propenal
polymer
poly
hair
treatment
Prior art date
Application number
PCT/AU2010/001387
Other languages
English (en)
Inventor
Robert William Dunlop
Original Assignee
Chemeq Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from AU2010100972A external-priority patent/AU2010100972A4/en
Application filed by Chemeq Ltd filed Critical Chemeq Ltd
Publication of WO2011047421A1 publication Critical patent/WO2011047421A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A61K31/765—Polymers containing oxygen
    • A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
    • 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
    • A61P17/08—Antiseborrheics

Definitions

  • the invention relates to an antifungal composition for topical use in treatment of dermatitis and method of treatment of dermatitis and in particular dermatitis infections caused or exacerbated by fungal infections such as dandruff, seborrhoeic dermatitis and dermaphytoses.
  • the invention also related to the use of the compositions in manufacture of topical medicaments for treatment of dermatitis.
  • Dermaphytoses are ichthyoses caused by fungal infections. The hyphae and spores are confined to nonviable portions of tissue and thus proliferate in the hyperkeratinized tissues of skin, hair, and nails. Examples of typical dermaphytoses include tinea capitis (cradle cap), tinea pedis (athlete's foot), and tinea unguium. These disorders are treated with anti-fungal agents, and topically with keratolytic agents to remove the cornified and infected layer.
  • Dermaphytoses include tinea pedis (athlete's foot) which affects the feet, tinea unguium which affects the fingernails and toenails, tinea corporis which affects the arms, legs, and trunk with ringworm, tinea cruris (jock itch) which affects the groin area, tinea manuum which affects the hands and palm area, tinea capitis affects the scalp, tinea barbae affects facial hair, tinea faciei (face fungus) which affects the face, tinea versicolor caused by Malassezia furfur and tinea nigra caused by Hortaea wasneckii.
  • Dandruff is understood to be caused by Malassezia yeasts such as Malassezia furfur. Malassezia yeasts are regarded as a precondition to developing dandruff but not all people with such yeast infections go on to develop dandruff.
  • the commonly used medications for treatment of dandruff are zinc pyrithione, octopyrox and ketoconazole which are often delivered by shampoo to the scalp. There is, however, a significant delay in effectiveness which is often 2 to 4 weeks during which sufferers have significant scalp itch and visible skin flakes.
  • Zinc pyrithione is relatively insoluble making it difficulty to formulate in some types of compositions and it is commonly used as a dispersion potentially reducing its effectiveness. Formulations are frequently very viscous requiring substantial rubbing to achieve penetration into the effected area, an act in itself which causes discomfort and sometimes irritation. If the viscous formulations are not vigorously applied, the active antifungal agent does not necessarily reach the site requiring treatment being the epidermis of the skin. Non-viscous creams and lotions are wont to flow off the effected site before penetration is achieved.
  • One final disadvantage is that cream and lotion bases in themselves can add to site irritation depending on their content.
  • Seborrhoea is a chronic skin disease that is considered to be a defect in keratinization with increased scale formulation. Dandruff is a mild form. Seborrhoea is divided into three clinical forms. Seborrhoea sicca, which is characterised by dry scaling of the skin. Seborrhoea oleosa is characterised by local to diffuse scaling associated with excessive sebum. Seborrhoeic dermatitis is characterised by scaling and greasiness with gross evidence of local or diffuse inflammation.
  • Chlorhexidine is a phenol-related biguanide antiseptic, it is a broad spectrum antimicrobial. It has been used as a topical wash, rinse and in a shampoo in veterinary and human medicine for over 30 years. Despite being widely used, it has not gained a reputation for value in seborrhoeic dermatitis.
  • an antifungal composition for treatment of dermatitis associated with fungal infections comprising a polymer of 2-propenal and a dermatologically acceptable carrier.
  • a method of treatment of dermatitis associated with a fungal infection comprising applying to at least a portion of the affected area of skin a topical composition comprising a polymer of 2-propenal.
  • the antifungal composition is typically for treatment of a dermatitis selected from the group consisting of dandruff, seborrhoeic dermatitis and dermaphytoses
  • Polymers of 2-propenal may be formed by radical or anionic polymerization and generally speaking have different structures and physical properties.
  • the polymer of 2- propenal is preferably a formed by anionic polymerization.
  • Such polymers typically comprise monomeric units linked through oxygen-carbon polymerization as well as carbon-carbon polymerization.
  • the anionic polymerization results in both polymerization through the vinyl group of 2-propenal as well as the aldehyde and hence, both monomer forms are present in the polymer.
  • the polymers of 2-propenal may be homopolymers or copolymers. Examples of copolymers include copolymers formed with alcohols such as C 2 to C 1 0 alkane diols, polyethylene glycol, hydroxy carboxylic acids, such as tartaric acid, ascorbic acid and mixtures thereof.
  • the polymer of 2-propenal topical antifungal typically comprises polymer repeating unit comprising at least one unit type selected from:
  • R is H or Ci -4 alkyl, and the hydrated, hemiacetal and acetal forms of the repeating unit.
  • R is hydrogen.
  • the polymer of 2-propenal may be a homopolymer or copolymer and in a particularly preferred embodiment the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).
  • Poly(2-propenal, 2-propenoic acid) is preferably formed by oxidation of a poly(2- propenal), preferably formed by anionic polymerization, so as to introduce carboxyl groups.
  • the poly(2-propenal, 2-propenoic acid) may comprise, for example, from 0.1 to
  • the topical composition in one embodiment comprises from 0.01 to 10% and preferably from 0.05 to 5% by weight of the polymer of 2-propenal and a dermatologically acceptable carrier.
  • poly(2-propenal, 2-propenoic acid) comprising from 0.1 to 5 moles of carboxyl groups per kilogram of polymer is described in US 6723336 (Example 1 b) in relation to the treatment of gastrointestinal disease and particularly colibacillosis (caused by E. Coli bacteria) in pigs.
  • the term "dermatologically-acceptable,” as used herein, means that the components so described are suitable for use in contact with human skin without undue toxicity, incompatibility, instability, allergic response, and the like.
  • Remington's Pharmaceutical Sciences Ed. by Gennaro, Mack Publishing, Easton, Pa., 1995 discloses various carriers used in formulating pharmaceutical compositions and known techniques for the preparation of such dosage forms.
  • the dermatologically-acceptable carriers used can be water or aqueous solutions; alcohols; diols; polyalkyleneglycols such as polyethyleneglycol (preferably of molecular weight of from 200 to 2000); oils, such as olive oil, peanut oil, sesame oil, sunflower oil, safflower oil, arachis oil, coconut oil, liquid paraffin, triglycerides of capric or of caprylic acid, or castor oil; fats, waxes and other natural and synthetic fatty materials, preferably esters of fatty acids with alcohols of low C number, e.g.
  • ethers of alcohols of low C number e.g.Ci to C 4 alkanols
  • ethers of alcohols of low C number e.g.Ci to C 4 alkanols
  • ethanol isopropanol, glycerol, ethylene glycol, propylene glycol, butylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products.
  • mixtures of the abovementioned solvents are used.
  • water can be a further constituent.
  • the carrier comprises a C-3- ⁇ alkanediol as part of the carrier.
  • the C 3- io alkanediol may be a linear chain C-3- ⁇ alkanediol or a branched chain C 3- i 0 alkanediol.
  • the C 3- i 0 alkanediol may be substituted or unsubstituted.
  • the C 3- io alkanediol in the composition may be selected from the group consisting of 1 ,2-ethanediol, 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-
  • C3-10 alkanediol is a 1 ,2-C 3- ioalkanediol.
  • the 1 ,2-C 3- io alkanediol may be a linear chain 1 ,2-C 3- 10 alkanediol or a branched chain 1 ,2-C 3- io alkanediol.
  • the 1 ,2-C 3- io alkanediol may be substituted or unsubstituted.
  • the 1 ,2-C 3- i 0 alkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-pentanediol, 1 ,2- hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2-nonanediol and 1 ,2-decanediol.
  • the C3-10 alkanediol is a 1 ,2-C 3- ioalkanediol selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • compositions of the invention may include a stabilizing agent.
  • the stabilizing agent may be an antioxidant selected from the group consisting of amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D,L- carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. a-carotene, ⁇ -carotene, lycopene) and their derivatives, lipoic acid and its derivatives (e.g. dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols
  • amino acids e.g. glycine, histidine, tyrosine, tryptophan
  • imidazoles e.g. urocanic acid
  • thioredoxin glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters
  • salts dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulphoximine compounds (e.g.
  • buthionine sulphoximines e.g. a-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), o hydroxy acids (e.g.
  • citric acid citric acid, lactic acid, malic acid
  • humic acid bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives
  • unsaturated fatty acids and their derivatives e.g. ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and its derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C and derivatives e.g. ascorbyl palmitate, Mg-ascorbyl phosphate, ascorbyl acetate
  • tocopherols and derivatives e.g.
  • vitamin E acetate
  • vitamin A and derivatives vitamin A palmitate
  • coniferyl benzoate from benzoin, rutic acid and its derivatives, ferulic acid and its derivatives, butylhydroxytoluene, butylhydroxyanisole, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (e.g. ZnO, ZnS0 4 ), selenium and its derivatives (e.g. selenomethionine), stilbenes and their derivatives (e.g.
  • stilbene oxide trans-stilbene oxide
  • derivatives suitable according to the invention salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
  • the stabilizing agent may be present at a concentration of from 0.2-3.0%.
  • compositions of the present invention can also include a thickening agent.
  • suitable thickening agents include cellulose and derivatives thereof such as carboxymethylcellulose hydroxyethylcellulose, cellulose acetate propionate carboxylate, hydroxyethylcellulose, hydroxyethylmethylcellulose, hydroxypropylcellulose, hydroxypropyl methylcellulose, methyl hydroxyethylcellulose, microcrystalline cellulose, sodium cellulose sulfate, and mixtures thereof.
  • Further suitable thickening agents include alkyl substituted celluloses.
  • hydroxyalkylated cellulose a proportion of the hydroxy groups of the cellulose polymer are hydroyxalkylated (preferably hydroxyethylated or hydroxypropylated) to form a hydroxyalkylated cellulose which is then further modified with a C10-C30 straight chain or branched chain alkyl group through an ether linkage.
  • these polymers are ethers of C10-C30 straight or branched chain alcohols with hydroxyalkylcelluloses.
  • alkyl groups useful for modifying the hydroxyalkyl cellulose include those selected from the group consisting of stearyl, isostearyl, lauryl, myristyl, cetyl, isocetyl, cocoyl (i.e. alkyl groups derived from the alcohols of coconut oil), palmityl, oleyl, linoleyl, linolenyl, ricinoleyl, behenyl, and mixtures thereof.
  • compositions of the invention include acacia, agar, algin, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, guar hydroxypropyltnmonium chloride, hectorite, hyaluronic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboxymethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof.
  • compositions according to the invention may further include preservatives.
  • Suitable preservatives include, but are not limited to, C C alkyl parabens and phenoxyethanol, calcium propionate, sodium nitrate, sodium nitrite, sulfites (sulfur dioxide, sodium bisulfite, potassium hydrogen sulfite, etc.) and disodium EDTA.
  • Preservatives are typically present in an amount ranging from about 0.5% to about 2.0% by weight percent, based on the total composition.
  • compositions of the invention contain a copolymer having the repeating units comprising at least one selected from the group consisting of;
  • R is H or Ci -4 alkyl and the hydrated, hemiacetal and acetal form of the repeating unit.
  • Such structures result from the anionic polymerization of 2-propenal.
  • the hydrated, hemiacetal or acetal form of the repeating unit is taken to include those copolymers having groups having any one or more of the following structures:
  • a typical example of a polymer segment is the segment of formula:
  • the structure can vary significantly within the polymer.
  • the polymer typically has a molecular weight of at least 1000 such as in the range of from 1000 to 10,000.
  • the "R" group can be any one of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group or a tert-butyl group.
  • the R group is a hydrogen atom and the copolymers be considered as the copolymers of 2-propenal and the hydrated, hemiacetal or acetal form of the 2-propenal monomer unit.
  • copolymers suitable for use on the compositions of the invention can be prepared by radical copolymerization of 2-propenal with any appropriate comonomer.
  • the copolymer is formed by the copolymerization of 2-propenal and 2-propenoic acid.
  • the copolymer suitable for use with the invention may be prepared by reacting a suitable precursor polymer.
  • a polymer suitable for use with the invention may be synthesized by partial reduction of a precursor such as poly(2-propenoic acid) to form poly(2- propenal, 2-propenoic acid) or more preferably by partial oxidation of poly(2-propenal) preferably to introduce from 0.1 to 5 mole carboxyl groups per kilogram of polymer.
  • a precursor such as poly(2-propenoic acid) to form poly(2- propenal, 2-propenoic acid) or more preferably by partial oxidation of poly(2-propenal) preferably to introduce from 0.1 to 5 mole carboxyl groups per kilogram of polymer.
  • compositions according to the invention can be made up in the customary manner and used for the treatment of the skin and/or of the hair in the sense of a dermatological treatment or of a treatment in the sense of medicated cosmetics. However, they can also be employed in decorative cosmetics in make-up products.
  • compositions according to the invention are applied to the skin and/or the hair in adequate amount in the manner customary for cosmetics and dermatological agents.
  • compositions according to the invention can contain cosmetic auxiliaries such as are customarily used in such preparations, e.g. preservatives, bactericides, antioxidants, perfumes, agents for preventing foaming, colorants, pigments which have a colouring action, thickeners, surface-active substances, emulsifiers, emollient substances, moisturizing and/or moisture-retaining substances, fats, oils, waxes or other customary constituents of a cosmetic formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic auxiliaries such as are customarily used in such preparations, e.g. preservatives, bactericides, antioxidants, perfumes, agents for preventing foaming, colorants, pigments which have a colouring action, thickeners, surface-active substances, emulsifiers, emollient substances, moisturizing and/or moisture-retaining substances, fats, oils, waxes or other customary constituent
  • Compositions according to the invention may further include preservatives.
  • Suitable preservatives include, but are not limited to, Ci-C 4 alkyl parabens and phenoxyethanol, calcium propionate, sodium nitrate, sodium nitrite, sulfites (sulfur dioxide, sodium bisulfite, potassium hydrogen sulfite, etc.) and disodium EDTA.
  • Preservatives are typically present in an amount ranging from about 0.5% to about 2.0% by weight percent, based on the total composition.
  • compositions of the invention optionally include a skin or hair cleansing agent.
  • the skin or hair cleansing agent may take the form of a soap or surfactant.
  • anionic surfactants potentially useful in the compositions of the invention include, but are not limited to, soaps, sulfates, sulfonates and carboxylates such as alkyl carboxylate salts.
  • useful anionic surfactants include alkyl sulfates and sulfonates, alkyl ether sulfates and sulfonates, alkyl aryl sulfates and sulfonates, aryl sulfates and sulfonates, sulfated fatty acid esters, sulfonated fatty acids, sulfated monoglycerides, sulfonated olefins, primary or secondary alkane sulfonates, alkyl sulfosuccinates, acyl taurates, methyl acyl taurates, acyl isothionates, alkyl glyceryl ether sulfonate, sulfonated methyl esters, alkyl phosphates, acyl glutamates, acyl sarcosinates, alkyl sulfoacetates, acylated peptides, alkyl
  • any counter cation can be used in the anionic surfactant.
  • the counter cation is selected from the group consisting of sodium, potassium, and counter cations derived from diethanolamine, or triethanolamine. In some particular embodiments the counter cation is sodium or potassium.
  • One group of anionic surfactants which may be used in the compositions of the invention is the group consisting of disodiumdecyl(sulfoxy)benzene sulphonate, sodium lauryl sulfate and disodium oxybis(decylsulfophenoxy)benzene sulfonate.
  • composition when the composition is in the form of a skin cleaner the composition may include a soap.
  • a soap is a surfactant having neutral to alkaline pH typically derived by neutralization of fatty acids with alkaline compounds such as alkali metal hydroxide or alkanolamines.
  • non-ionic surfactants potentially suitable for use with the compositions of the invention include, but are not limited to, alkyl polyglycosides, alcohol ethoxylates such as fatty alcohol ethoxylates and/or propoxylates, alkyl phenolethoxylates, glycol ester surfactants, PEG(20) sorbitan monooleate, polyethylene glycol cocoate, propylene oxide/ethylene oxide block polymers, alkanolamines, and mixtures thereof.
  • alcohol ethoxylates such as fatty alcohol ethoxylates and/or propoxylates
  • alkyl phenolethoxylates alkyl phenolethoxylates
  • glycol ester surfactants PEG(20) sorbitan monooleate
  • polyethylene glycol cocoate propylene oxide/ethylene oxide block polymers
  • alkanolamines and mixtures thereof.
  • Some specific non-ionic surfactants suitable for use in the compositions of the invention include polyoxyalkylene glycol based surfactants.
  • These polyoxyalkylene based surfactants include hexitan esters such as polysorbates, polyethoxylated alkylphenols, poloxamers, polyethoxylated fatty alcohols, polyoxyethylene glycol monoethers, alkyl polyglucosides and ethoxylated polysiloxanes.
  • amphoteric surfactants useful in compositions of the invention include but are not limited to betaines, amine oxides, sultaines, and mixtures thereof. More specifically, examples of useful amphoteric surfactants include alkyl betaines (oleyl betaine and lauryl betaine), cocamidopropyldimethyl betaine, cocamido betaine, alkyl sultaines, alkyl amphoacetates (cocamphoacetate), alkyl amphodiacetates (cocamphodiacetate), alkyl amphopropionates, alkyl amphodipropionates (cocamphocarboxypropionate), cocamphocarboxy propionic acid, cocamidopropylhydroxysultaine, alkyldimethyl amine oxides, coconut monoethanolamine, cetydimethylamine oxide, stearamine oxide, oleamine oxide, cocamidopropylamine dimethyl oxide, and mixtures thereof.
  • alkyl betaines oleyl be
  • compositions of the invention may also include a skin softening agent.
  • the skin softening agents suitable for use with the compositions of the invention are, when incorporated into the composition and applied to the skin, essentially clear, colorless, and non-malodorous. They are dermatologically safe and are compatible with the active agents of the compositions as well as any other composition ingredients.
  • the skin softening agents can be used singly or in combination in a concentration ranging from approximately 0.01 to 10.0% w/v. In some embodiments they are included in the range of from approximately 0.05 to 5.0%.
  • Skin softening agents suitable for use in the present invention include, but are not limited to, glycerin, caprylic/capric triglyceride, pantothenol and its derivatives and related moieties, and hyaluronic acid and related moieties.
  • Other appropriate skin softening agents suitable for use in the compositions of the invention would be readily known to one having ordinary skill in the art.
  • the antifungal composition may additionally comprise a polymeric carrier such as an acrylate, methacrylate, polyvinylpyrrolidone, stable aqueous carboxy vinyl polymer gels, silicones or other suitable polymer.
  • a polymeric carrier such as an acrylate, methacrylate, polyvinylpyrrolidone, stable aqueous carboxy vinyl polymer gels, silicones or other suitable polymer.
  • the compositions according to the invention may also include a fragrance.
  • the fragrance may be present at between about 0.0001 % (v/v) and about 2.0%) (v/v) of the final composition. In some cases the fragrance is present between about 0.001 % (v/v) and 1 .0% (v/v). In still other cases the fragrance is present between 0.01 % (v/v) and 5% (v/v) of the final composition.
  • the term "fragrance” is meant to encompass any component reacting with the human olfactory sites and imparting a pleasurable odor, essence or scent. Fragrances that may be used in accordance with the present invention include any synthetic as well as natural fragrance and mixtures thereof.
  • top note i.e. fragrances having a high vapor pressure
  • middle note i.e. fragrance having a medium vapor pressure
  • base note i.e. fragrances having a low vapor pressure
  • categorization within these classes may depend to some extent on the fragrance formulator, the compositions of the present invention may include any top note, middle note and base note fragrance.
  • a further way of classifying fragrances is in accordance with generally recognized scents they produce.
  • fragrances are inter alia "rose”, “floral”, “green”, “citrus”, “spicy”, “honey”, “musk”, “herbal, “jasmine”, “lilac”, lily of the valley”, “orange”, “peach”, “oriental”, “watermelon” “chypre” and “lemon”, “woody”, “fruity” all of which fragrances thus classified may be formulated with the compositions of the present invention.
  • Fragrances that may be used in accordance with the present invention include linear and cyclic alkenes (e.g. terpenes); primary, secondary and tertiary alcohols; ethers; esters; ketones; nitrites; and saturated and unsaturated aldehydes; or mixtures thereof.
  • Examples of synthetic fragrances that may be used in the compositions of the present invention include acetanisole; acetophenone; acetyl cedrene; methyl nonyl acetaldehyde; musk anbrette; heliotropin; citronellol; sandella; methoxycitranellal; hydroxycitranella); phenyl ethyl acetate; phenyletlhylisobutarate; gamma methyl ionone; geraniol; anetlhole; benzaldehyde; benzyl acetate; benzyl salicate; linalool; ciitiamic alcohol; phenyl acetaldehyde; amyl cinnamic aldehyde; caphore; p-tertiairy butyl cyclohexyl acetate; citral; cinnamyl acetate; citral
  • fragrances suitable for use in the compositions of the invention would be readily known to one having ordinary skill in the art.
  • natural fragrances include without limitation lavandin; heliotropin; sandlewood oil; oak moss; patchouly; ambergris tincture; ambrette seed absolute; angelic root oil; bergamont oil; benzoin Siam resin; buchu leaf oil; cassia oil; cedarwood oil; cassia oil; castorcum; civet absolute; chamomile oil; geranium oil; lemon oil; lavender oil; Ylang Ylang oil; and mixtures thereof. It will of course be appreciated that other dermatologically acceptable natural fragrances suitable for use in the compositions of the invention would be readily known to one having ordinary skill in the art.
  • compositions of the invention may also include a dye.
  • Dyes suitable for use with the compositions of the invention include fat-soluble dyes and water-soluble dyes.
  • the dye if present, may be present in an amount generally ranging from 0.001 % to 2.0% by weight relative to the total weight of the composition. In some cases the dye is present in an amount from 0.005% to 1 .0%. In other cases the dye is present in an amount form from 0.01 % to 0.5%.
  • dyes suitable for use with the compositions of the invention will be dermatologically acceptable dyes.
  • fat-soluble dyes include Soudan red, D & C Red 17, D & C Green 6, ⁇ -carotene, soybean oil, Soudan brown, D & C Yellow 1 1 , D & C Violet 2, D & C Orange 5, and quinoline yellow.
  • water-soluble dyes include beet juice and methylene blue.
  • Compositions of the invention may also include a pigment.
  • the pigment can be white or colored, inorganic and/or organic, coated or uncoated.
  • Suitable such inorganic pigments include titanium dioxide, optionally treated on its surface, or zirconium oxide or cerium oxide, as well as iron oxide or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • Suitable organic pigments include carbon black, and lakes based on cochineal carmine or on barium, strontium, calcium or aluminum.
  • the pigments may be pearlescent.
  • the pearlescent pigments can be selected from white pearlescent pigments such as mica covered with titanium oxide or with bismuth oxychloride, colored pearlescent pigments such as titanium oxide-coated mica coated with iron oxides, titanium oxide-coated mica coated with, in particular, ferric blue or chromium oxide, or titanium oxide-coated mica coated with an organic pigment of the above-mentioned type, as well as pearlescent pigments based on bismuth oxychloride.
  • compositions of the invention may be formulated as any type of formulation appropriate for application to the skin, hair or scalp.
  • the compostions of the invention may be formulated as a hand lotion, a sunscreen, a face cream, a moisturizer, a barrier cream, a hand sanitizer, a hair lotion, a hair gel, a hair mousse, a shaving cream, a shaving gel, a deodorant, a night emollient cream, a hair treatment course, a hair rinse, a hair spray, a shampoo, a conditioner, a lipstick, a formulation for blow-drying, a formulation for hair setting, a formulation for colouring or bleaching, a styling or treatment lotion, a hair lacquer, or a permanent wave composition.
  • compositions according to the invention are applied to the skin and/or the hair in adequate amount in the manner customary for cosmetics and dermatological agents.
  • the precise amount applied will be dependent on the precise formulation adopted and on the severity of the complaint for which the composition is being applied.
  • compositions may be applied to skin or hair while wet or while dry. In some cases, the compositions will be rinsed from the skin or hair immediately after applying, as in a process of washing the hair or skin. In other cases the compositions may be applied and left in contact with the skin for a variable period of time, after which the composition is removed. In still other cases, the compositions may be rubbed onto or into the skin or hair and left, as in application a hand cream or certain leave-in hair conditioners.
  • the methods of the invention will be applied in association with other treatments or methods.
  • the methods of the invention involve the application of a composition formulated as a shampoo, this might be applied is association with an appropriate conditioner.
  • the methods of the invention might involve the application of compositions of the invention as a conditioner in association with an appropriate shampoo.
  • the compositions of the invention may be applied as formulations used while rinsing the hair before or after shampooing, before or after permanent wave treatment, or before or after colouring or bleaching the hair.
  • the antifungal composition may comprise one or more additional antifungal agents which may provide synergy or complementary activity.
  • the composition may comprise from about 0.1 % to about 10% by weight of one or more additional antifungal agents although such agents are not generally required in order to provide useful antifungal activity.
  • additional antifungal agents may be selected from the group consisting of elemental sulfur, selenium sulfide, zinc pyrithione, triclosan, trichlorocarbanilide, dipotassium glycyrrhizinate, monoammonium glycyrrhizinate, allantoin, isopropylmethylphenol, ketoconazole, climbazole and salicylic acid.
  • the complexes of copper such as is the copper complex of ethylenediaminetetraacetic acid may be present the compositions to mask the odor of additional antidandruff agents although the active poly(2-propenal) polymer generally has little or no odor.
  • the antifungal composition is in a form selected from the group consisting of shampoo, conditioner, aerosol spray, gel, paste, cream, lotion, sponge, emulsion, soap or ointment.
  • the antifungal is for treatment of dandruff and in the form of shampoo.
  • the shampoo may be prepared as rinse-off or leave-on after-shampoo products, as well as two stage treatment shampoos. Additionally, the composition may also be prepared as a stand-alone conditioner or pre- or post-shampoo conditioner.
  • the compositions are administered as a shampoo, then as a conditioner after the shampoo is rinsed away and optionally in a higher concentration form, such as a gel, subsequently thereto.
  • a higher concentration form such as a gel
  • the antifungal for use in the methods of the present invention suitable for topical administration may be presented as discrete units including aerosol sprays, each containing a predetermined amount of the active ingredient, as a powder, stick, or granules, as creams (e.g., a conditioner), pastes, gels, lotions (e.g., a sunscreen), ointments, on sponges or cotton applicators, or as a solution or a suspension in an aqueous liquid, a non-aqueous liquid, an oil-in-water emulsion, or a water-in-oil liquid emulsion.
  • aerosol sprays each containing a predetermined amount of the active ingredient, as a powder, stick, or granules, as creams (e.g., a conditioner), pastes, gels, lotions (e.g., a sunscreen), ointments, on sponges or cotton applicators, or as a solution or a suspension in an aqueous liquid, a
  • compositions may be prepared by any of the methods of pharmacy, but all methods include the step of bringing into association the carrier(s) with the active ingredient, which comprises the poly(2-propenal) polymer.
  • the compositions are prepared by uniformly and intimately admixing the active ingredient with liquid carriers or finely divided solid carriers or both, and then, if necessary, shaping the product into the desired presentation.
  • the antifungal composition is an aqueous alcohol composition optionally additionally comprising one or more of the components referred to above.
  • the content of alcohols such as one or more selected from lower alkanols (Ci to C alkanol), alkane diols, polyalkylene diol may be in the range of from 1 to 99.9% and preferably from 10 to 60% by weight.
  • the composition contains a weight ratio of alkanol to alkanediol in the range of from 1 : 10 to 10:1 .
  • the polymer of 2-propenal has been found to confer film forming properties on the composition and may provide an advantage in improving the contact between the affected areas of skin and the active components including the polymer of 2-propenal. Further the polymer of 2-propenal may confer an attractive skin feel making it more desirable for application to the skin and for leave-on antifungal compositions. [0069] Examples of materials and methods for use with the compositions and methods of the present invention will now be provided. In providing these examples, it is to be understood that the specific nature of the following description is not to limit the generality of the above description.
  • Poly(2-propenal, 2-propenoic acid) was used in powdered form obtained by the following method.
  • Water (720 ml. at ambient temperature, about 20°C) and 2-propenal (60g; freshly distilled) were placed in an open beaker, within a fume cupboard and vigorously stirred.
  • 0.2M aqueous sodium hydroxide (21 .4 ml.) was added to bring the pH to 10.5 - 1 1 .0.
  • the clear solution became milky and then precipitation of a white flocculant polymer began, and appeared complete within 30 minutes.
  • the precipitate was filtered and washed with water (250 ml_), dried at room temperature (2 days) to yield 25g of white polypropenal.
  • the polymer was spread on trays and heated in a temperature controlled oven at 40°C/8 hours. This heating was continued at the schedules : 50°C/15 hours; 65°C/4 hours/75°C/18 hours; 84°C/24 hours.
  • Poly(2-propenal, 2-propenoic acid) was also prepared by preparing polypropenal as above, but alternatively dissolving the polymer (10g) as a 10% solution in ethanol, adding 30% w/w hydrogen peroxide (4.5 ml_). The solution was heated at 75°C for 2 hours. The ethanol was evaporated and the product dried to give a white semi-crystalline product.
  • Poly(2-propenal, 2-propenoic acid) produced by either oxidation method have identical physicochemical and antimicrobial properties.
  • compositions of Examples 1 to 32 and 37 to 53 may be prepared by mixing the poly(2-propenal, 2-propenoic acid) with the alcohol portions with mild heating to no more than 70°C if necessary to dissolve the polymer. Once dissolved, the remaining components are mixed with the solution to provide a homogenous composition.
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 2 Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,3- butanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 4 Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- hexanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 5 Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- heptanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 6 Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- octanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 8 Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- decanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 10 Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3-butanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 12 Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-hexanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 14 Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-octanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 16 Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-decanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 18 Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3- butanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 20 Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- hexanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 22 Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- octanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • Example 24 Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- decanediol
  • Preservatives 1 .0 1 .0 1 .0 1.0 fragrance, dye
  • fragrance dye, 1 .0 1 .0 1 .0 1.0 thickeners
  • Example 26 Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3- butanediol
  • fragrance dye, 1 .0 1 .0 1 .0 1.0 thickeners
  • fragrance dye, 1 .0 1 .0 1 .0 1.0 thickeners
  • Example 28 Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- hexanediol
  • fragrance dye, 1 .0 1 .0 1 .0 1.0 thickeners
  • fragrance dye, 1 .0 1 .0 1 .0 1.0 thickeners
  • Example 30 Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- octanediol
  • fragrance dye, 1 .0 1 .0 1 .0 1.0 thickeners
  • fragrance dye, 1 .0 1 .0 1 .0 1.0 thickeners
  • Example 32 Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- decanediol
  • fragrance dye, 1 .0 1 .0 1 .0 1.0 thickeners
  • Samples were prepared by adding selected C3-ioalkanediols to a final concentration of either 2000 or 10000 ppm in an ethanolic solution of poly(2-propenal, 2- propenoic acid) (2000 ppm). Compositions studied are tabulated in Table 1 .
  • Table 1 Composition of 1 ,2-C 3- ioalkanediol / poly(2-propenal, 2-propenoic acid) Antimicrobial Compositions (Concentrations are ppm in ethanol)
  • the minimum inhibitory concentration (MIC) of poly(2-propenal, 2-propenoic acid) was thereafter determined against Escherichia coli (ATCC 8739 strain) after evaporation of the ethanol.
  • the MIC values determined are tabulated in Table 2.
  • the purpose of this placebo controlled study is to evaluate the efficacy of an anti- dandruff treatment when tested over a 16 days period. Efficacy was evaluated for each subject through analysis of debris collection via D-Squame surface sampling discs. In addition the efficacy and tolerance were evaluated using panelist self-assessment via questionnaire responses.
  • a control placebo was prepared by combining the following components in the amounts by weight specified.
  • compositions of Examples 34 to 36 which were used in the three arms of the study, were prepared by dissolving poly(2-propenal, 2-propenoic acid) ("PPPA”) in powdered form in the alcohol component and mixing the alcohol solution with water to provide a homogenous solution.
  • PPPA poly(2-propenal, 2-propenoic acid)
  • test materials were assigned unique laboratory code numbers and entered into a daily log identifying the lot number, sample description, sponsor, date received and tests requested.
  • Day 1 Scalp debris collection (Baseline)
  • Day 1-7 7 day use with Placebo
  • Adhesive discs take the trial and error out of sampling the cells of the superficial stratum corneum (top layer of skin). These crystal clear discs provide the required rigidity and adhesion to uniformly sample a fixed area of skin surface. The clear polymer discs provide optimum visibility of adhering skin cells and allow staining by many histological preparations.
  • D-Squame disc is applied to clean, dry skin surface. It is pressed firmly for a few seconds using thumb or fingertips, and then transferred to a black square on the storage card where is compared with reference patterns. Heavy amount of scaling represents pattern 5. Normal skin producing a few areas of small clumps of cells or a fine even single layer of cells represents pattern 1 .
  • the source data are collected Questionnaire responses and D-Squame Skin Sampling Discs employed prior to application (Baseline) and again after 8 (Post Treatment - Placebo) and 16 days following the applications of the Example materials.
  • the data used in the statistical analysis reflect changes from Baseline and Post Treatment - Placebo evaluation.
  • D-SQUAME Skin Sampling Discs method describes pattern representing 100% improvement in the condition (no scaliness) as 1 , therefore the following formula was used to calculate the reduction in scal flakiness:
  • Figure 1 is a column chart comparing the flake reduction via D-Squame score for the 500ppm composition of Example 34 sixteen days post treatment with a placebo.
  • Figure 2 is a column chart comparing the flake reduction via D-Squame score for l OOOppm composition of Example 35 sixteen days post treatment with a placebo.
  • Figure 3 is a column chart comparing the flake reduction via D-Squame score for the 2000ppm composition of Example 36 sixteen days post treatment with a placebo.
  • Example 37 Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3- butanediol
  • Example 38 Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3- butanediol
  • Microcrystalline Cellulose 1 0.1 0.5 0.25 0.1
  • Glycerylsteratcitrate 1 0.5 0.1 0.5 0.3 0.2 0.7 0.3

Landscapes

  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une composition antifongique pour le traitement topique de la dermatite associée à des infections fongiques comprenant un polymère de 2-propénal et un véhicule acceptable en dermatologie.
PCT/AU2010/001387 2009-10-19 2010-10-19 Composition antifongique et procédé de traitement de la dermatite WO2011047421A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US25287209P 2009-10-19 2009-10-19
US61/252,872 2009-10-19
AU2010100972 2010-09-06
AU2010100972A AU2010100972A4 (en) 2009-10-19 2010-09-06 Topical antimicrobial compositions

Publications (1)

Publication Number Publication Date
WO2011047421A1 true WO2011047421A1 (fr) 2011-04-28

Family

ID=43899720

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU2010/001387 WO2011047421A1 (fr) 2009-10-19 2010-10-19 Composition antifongique et procédé de traitement de la dermatite

Country Status (1)

Country Link
WO (1) WO2011047421A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2438903B1 (fr) 2010-10-07 2018-03-14 Beiersdorf AG Produit de protection solaire sans conservateur
EP2793831B1 (fr) 2011-12-20 2018-10-03 L'Oréal Composition cosmétique comprenant un tensioactif anionique, un alcool gras solide et un ester gras solide, et procédé de traitement cosmétique
WO2018226651A1 (fr) * 2017-06-05 2018-12-13 The Procter & Gamble Company Compositions de soins capillaires comprenant des matières qui modifient le sébum
WO2019115503A1 (fr) * 2017-12-13 2019-06-20 Dsm Ip Assets B.V. Mononitrate-monoacétate de propanediol
US20190365617A1 (en) * 2018-06-05 2019-12-05 The Procter & Gamble Company Rinse-off cleansing compositions comprising materials that modify sebum
JP2022510356A (ja) * 2018-12-04 2022-01-26 ザ プロクター アンド ギャンブル カンパニー 毛髪及び頭皮を洗浄及びリフレッシュするためのヘアケア組成物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000003723A1 (fr) * 1998-07-17 2000-01-27 Chemeq Limited Composes polymeres et leurs procedes de formulation
WO2002026211A1 (fr) * 2000-09-27 2002-04-04 Chemeq Ltd Emulsion antimicrobienne polymere topique
US20030195131A1 (en) * 2000-02-16 2003-10-16 Melrose Graham John Hamilton Antimicrobial polymeric compositions and method of treatment using them
WO2004013636A2 (fr) * 2002-08-01 2004-02-12 Syngenta Participations Ag Etiquetage differentiel pour l'analyse quantitative de melanges de proteines complexes
WO2009009828A1 (fr) * 2007-07-19 2009-01-22 Chemeq Ltd Composition de poly-acroléine biocide
WO2010071925A1 (fr) * 2008-12-22 2010-07-01 Chemeq Ltd Préparation d'un antimicrobien

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000003723A1 (fr) * 1998-07-17 2000-01-27 Chemeq Limited Composes polymeres et leurs procedes de formulation
US20030195131A1 (en) * 2000-02-16 2003-10-16 Melrose Graham John Hamilton Antimicrobial polymeric compositions and method of treatment using them
WO2002026211A1 (fr) * 2000-09-27 2002-04-04 Chemeq Ltd Emulsion antimicrobienne polymere topique
WO2004013636A2 (fr) * 2002-08-01 2004-02-12 Syngenta Participations Ag Etiquetage differentiel pour l'analyse quantitative de melanges de proteines complexes
WO2009009828A1 (fr) * 2007-07-19 2009-01-22 Chemeq Ltd Composition de poly-acroléine biocide
WO2010071925A1 (fr) * 2008-12-22 2010-07-01 Chemeq Ltd Préparation d'un antimicrobien

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2438903B1 (fr) 2010-10-07 2018-03-14 Beiersdorf AG Produit de protection solaire sans conservateur
EP2793831B1 (fr) 2011-12-20 2018-10-03 L'Oréal Composition cosmétique comprenant un tensioactif anionique, un alcool gras solide et un ester gras solide, et procédé de traitement cosmétique
EP2793831B2 (fr) † 2011-12-20 2021-11-10 L'Oréal Procédé de traitement cosmétique avec une composition comprenant un tensioactif procédé anionique, un alcool gras solide et un ester gras solide
WO2018226651A1 (fr) * 2017-06-05 2018-12-13 The Procter & Gamble Company Compositions de soins capillaires comprenant des matières qui modifient le sébum
JP2020504083A (ja) * 2017-06-05 2020-02-06 ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ 皮脂を変性する物質を含むヘアケア組成物
WO2019115503A1 (fr) * 2017-12-13 2019-06-20 Dsm Ip Assets B.V. Mononitrate-monoacétate de propanediol
CN111491608A (zh) * 2017-12-13 2020-08-04 帝斯曼知识产权资产管理有限公司 丙二醇单乙酸酯单硝酸酯
US11306054B2 (en) 2017-12-13 2022-04-19 Dsm Ip Assets B.V. Propanediol monoacetate mononitrate
CN111491608B (zh) * 2017-12-13 2023-01-24 帝斯曼知识产权资产管理有限公司 丙二醇单乙酸酯单硝酸酯
US20190365617A1 (en) * 2018-06-05 2019-12-05 The Procter & Gamble Company Rinse-off cleansing compositions comprising materials that modify sebum
JP2022510356A (ja) * 2018-12-04 2022-01-26 ザ プロクター アンド ギャンブル カンパニー 毛髪及び頭皮を洗浄及びリフレッシュするためのヘアケア組成物
JP7227372B2 (ja) 2018-12-04 2023-02-21 ザ プロクター アンド ギャンブル カンパニー 毛髪及び頭皮を洗浄及びリフレッシュするためのヘアケア組成物

Similar Documents

Publication Publication Date Title
WO2011047420A1 (fr) Compositions cosmétiques
AU2010100972A4 (en) Topical antimicrobial compositions
EP1667640B1 (fr) Preparation de soin pour la peau et les cheveux, contenant des hydrolysats de proteines
AU2016354029B2 (en) Pet care cleansing composition
US9295618B2 (en) Personal care products containing rainwater
US11364208B2 (en) Topical compositions
WO2011047421A1 (fr) Composition antifongique et procédé de traitement de la dermatite
EP1889602A2 (fr) Préparations cosmétiques destinées à la reconstructions de cheveux, en particulier de dérivés d'urées
US20080194662A1 (en) Cleanser composition
FR2820030A1 (fr) Composition de traitement des matieres keratiniques comprenant un polymere poly(alkyl)vinyllactame cationique et un agent protecteur ou conditionneur
WO1997022624A2 (fr) Preparations cosmetiques renfermant des proteines de vertebres, a effet antibacterien, antimycosique et antiviral
US20220096347A1 (en) Active agents for skin and hair care with sensory modifying properties
EP1604640B1 (fr) Composition de traitement des cheveux et du cuir chevelu
JP4812304B2 (ja) 毛髪用組成物
JP2005194252A (ja) 脂肪蓄積抑制用組成物
DE102009045856A1 (de) Verwendung kationischer Polymere in Haut- und Haarreinigungsmitteln
DE19540464A1 (de) Antimycotische, insbesondere gegen Kopfschuppen wirksame, Zubereitungen mit einem wirksamen Gehalt an Arylverbindungen
EP1536756B1 (fr) Combinaison de substances actives comprenant du climbazole, du pirocton olamine et de l'undecylene amidopropyle betaine. son utilisation pour la lutte contre les pellicules
US11857661B2 (en) Anti-dandruff composition
DE102010015788A1 (de) Kosmetische Zubereitung mit einem Gehalt an Magnolienrindenextrakt zur Steigerung der Mikrozirkulation der haut sowie die Verwendung von Magolienrindenextrakt zur Herstellung topischer Zubereitungen zur Steigerung der Mikrozirkulation der Haut und/oder angiogenetisch wirksamer topischer Zubereitungen
US20230129036A1 (en) Avenanthramide compositions with improved solubility comprising 4-hydroxyphenone
WO2011047422A1 (fr) Composition anti-acné et utilisation de celle-ci
de Wit-Bos et al. Cosmetovigilance in The Netherlands: Overview of the period 2009-2014
EP1537848A1 (fr) Compositions pour le traitement des cheveux et/ou du cuir chevelu contenant licochalcone A
DE19521240A1 (de) Antimycotische Zubereitungen mit einem wirksamen Gehalt an Nitrilen und Arylverbindungen

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10824303

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10824303

Country of ref document: EP

Kind code of ref document: A1