WO2011047421A1 - Antifungal composition and method of treatment of dermatitis - Google Patents

Abstract

An antifungal composition for topical treatment of dermatitis associated with fungal infections comprising a polymer of 2-propenal and a dermatologically acceptable carrier.

Description

Antifungal Composition and

Method of Treatment of Dermatitis

Field

[0001] 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.

Background

[0002] 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.

[0003] Specific examples of 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 werneckii.

[0004] 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.

[0005] 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.

[0006] While zinc pyrithione biocides have proven useful for a wide range of applications, the utility of these compounds is limited to the control of select species and strains of fungi and bacteria. Further, while higher concentrations of pyrithione salts have been observed to control the growth of a wider range of organisms, the useful amount of polyvalent metal salts of pyrithione that can be added to a commercial product is limited by efficacy and economic considerations, and environmental concerns.

[0007] Many antifungals such as sulfur based antifungals also have an unpleasant odour or stench.

[0008] The number of patients not responding to particular medicated shampoo can be quite high (ketoconazole up to 30%; selenium sulfide up to 40%).

[0009] 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. In addition to human infections, many animals such as certain dog species are more succeptible to seborrheoa such as Cocker Spaniels, Springer Spaniels, Basset Hounds and, in particular, the most difficult form occurs in West Highland White Terriers. Certain dogs also have persistent ear fungal infections.

[0010] 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.

[0011] Although sulfur has been used extensively in cosmetic products, its use has not been entirely satisfactory. One major problem associated with its use in shampoos has been the generation of sulfide off odors during the shampooing process and, often, of residual sulfide off odors for days afterwards. Selenium sulfide also suffers from this sulfide off odor problem.

[0012] There is a need for a safe and effective antifungal for topical use in treatment of dermatitis.

Summary

[0013] There is provided the use of a polymer of 2-propenal in preparation of a topical medicament for treatment of dermatitis.

[0014] In accordance with a further embodiment there is provided an antifungal composition for treatment of dermatitis associated with fungal infections comprising a polymer of 2-propenal and a dermatologically acceptable carrier.

[0015] In accordance with one embodiment there is provided 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. [0016] The antifungal composition is typically for treatment of a dermatitis selected from the group consisting of dandruff, seborrhoeic dermatitis and dermaphytoses

[0017] 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. Thus, 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 C₂ to C₁0 alkane diols, polyethylene glycol, hydroxy carboxylic acids, such as tartaric acid, ascorbic acid and mixtures thereof.

[0018] The polymer of 2-propenal topical antifungal typically comprises polymer repeating unit comprising at least one unit type selected from:

wherein R is H or Ci_-4 alkyl, and the hydrated, hemiacetal and acetal forms of the repeating unit.

[0019] In some embodiments of the compositions of the invention, 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

5 moles of carboxyl groups per kilogram of polymer. [0020] 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.

[0021] An example of such a 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.

Detailed Description

[0022] 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.

[0023] If the composition may be a solution or lotion, 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. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids; ethers of alcohols of low C number (e.g.Ci to C₄ alkanols) , preferably 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. In some cases, mixtures of the abovementioned solvents are used. In the case of alcoholic solvents, water can be a further constituent.

[0024] In one embodiment of the antifungal composition the carrier comprises a C-3-ιο alkanediol as part of the carrier. The C_3-io alkanediol may be a linear chain C-3-ιο alkanediol or a branched chain C_3-i₀ alkanediol. The C_3-i₀ alkanediol may be substituted or unsubstituted. As noted above, 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-octanediol, 1 ,9 nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol. In some cases, 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. In some cases, the 1 ,2-C_3-i₀alkanediol 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. In some cases 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.

[0025] We have found that the combination of the polymer of 2-propenal and the C_3-io alkanol provides a synergistic improvement in antifungal activity.

[0026] Various embodiments of the 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, β-carotene, lycopene) and their derivatives, lipoic acid and its derivatives (e.g. dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols

(e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and glyceryl esters) and their 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, homocysteine sulphoximine, buthionine sulphones, penta-, hexa- or heptathioninesulphoxime) in very low tolerable doses (e.g. pmol to pmol/kg), further (metal) chelators (e.g. a-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), o hydroxy acids (e.g. 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. γ-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) and 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, ZnS0₄), selenium and its derivatives (e.g. selenomethionine), stilbenes and their derivatives (e.g. stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these said active compounds. The stabilizing agent may be present at a concentration of from 0.2-3.0%.

[0027] The 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. In these polymers 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. Typically these polymers are ethers of C10-C30 straight or branched chain alcohols with hydroxyalkylcelluloses. Examples of 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.

[0028] Other thickening agents suitable for use with the 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.

[0029] 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.

[0030] Compositions of the invention contain a copolymer having the repeating units comprising at least one selected from the group consisting of;

wherein 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:

[0031] A typical example of a polymer segment is the segment of formula:

wherein X are remaining portions of the polymer.

[0032] It will, however, be appreciated that because of the option of oxygen-carbon or carbon-carbon polymerization 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. [0033] 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. In particular embodiments of the invention 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.

[0034] In some cases, copolymers suitable for use on the compositions of the invention can be prepared by radical copolymerization of 2-propenal with any appropriate comonomer. In some specific embodiments of the invention the copolymer is formed by the copolymerization of 2-propenal and 2-propenoic acid. In other cases the copolymer suitable for use with the invention may be prepared by reacting a suitable precursor polymer. For instance, 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.

[0035] The 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.

[0036] For use, the 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.

[0037] The 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.

[0038] Compositions according to the invention may further include preservatives. Suitable preservatives include, but are not limited to, Ci-C₄ 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.

[0039] The 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. Examples of 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. More specifically, 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 ether carboxylates, acyl lactylates, anionic fluorosurfactants, ethoxylated alkyl sulfates, alkyl glyceryl ether sulfonates, fatty acyl glycinates, alpha- sulfonated fatty acids, their salts and/or their esters, alkyl ethoxy carboxylates, and mixtures thereof.

[0040] Any counter cation can be used in the anionic surfactant. In some specific cases 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. [0041] 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.

[0042] 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.

[0043] Examples of 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.

[0044] 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.

[0045] Examples of 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.

[0046] Other skin or hair cleansing agents appropriate for use in the compositions of the invention would be readily known by one of ordinary skill in the art.

[0047] The 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.

[0048] 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.

[0049] 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. For the purpose of the present application 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. Typically a multiplicity of fragrances are used to achieve the desired effect. Those of skill in the art further recognize the terms "top note" (i.e. fragrances having a high vapor pressure), "middle note" (i.e. fragrance having a medium vapor pressure) and "base note" (i.e. fragrances having a low vapor pressure). Recognizing that 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. Descriptors used by those skilled in the art of 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.

[0050] 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.

[0051] 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 diethyl acetal; coumarin; ethylene brasslate.; eugenol; 1-mentlhol; vanillin; and mixtures thereof. It will of course be appreciated that other dermatologically acceptable synthetic fragrances suitable for use in the compositions of the invention would be readily known to one having ordinary skill in the art. [0052] Examples of natural fragrances that may be used in the compositions of the present invention 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.

[0053] 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%. As will be appreciated by one having skill in the art, dyes suitable for use with the compositions of the invention will be dermatologically acceptable dyes.

[0054] Examples of fat-soluble dyes include Soudan red, D & C Red 17, D & C Green 6, β-carotene, soybean oil, Soudan brown, D & C Yellow 1 1 , D & C Violet 2, D & C Orange 5, and quinoline yellow. Examples of water-soluble dyes include beet juice and methylene blue.

[0055] 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.

[0056] In some cases 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.

[0057] Compositions of the invention may be formulated as any type of formulation appropriate for application to the skin, hair or scalp. In some cases 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.

[0058] For the methods of the invention, the 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.

[0059] The 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.

[0060] In some instances the methods of the invention will be applied in association with other treatments or methods. For instance, when 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. In other cases, the methods of the invention might involve the application of compositions of the invention as a conditioner in association with an appropriate shampoo. In some cases 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.

[0061 ] The antifungal composition may comprise one or more additional antifungal agents which may provide synergy or complementary activity.

[0062] 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. Examples of 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.

[0063] 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.

[0064] In one embodiment 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.

[0065] In one embodiment 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. In a preferred embodiment, 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. Each of these forms is well understood by those of ordinary skill in the art, such that dosages may easily be prepared to incorporate the antidandruff composition.

[0066] 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. Such 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. In general, 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.

[0067] In one embodiment the antifungal composition is an aqueous alcohol composition optionally additionally comprising one or more of the components referred to above. In this embodiment 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. In one embodiment the composition contains a weight ratio of alkanol to alkanediol in the range of from 1 : 10 to 10:1 .

[0068] 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.

EXAMPLES

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. Then, 0.2M aqueous sodium hydroxide (21 .4 ml.) was added to bring the pH to 10.5 - 1 1 .0. Within a minute, 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.

[0086] 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.

[0087] Poly(2-propenal, 2-propenoic acid) produced by either oxidation method have identical physicochemical and antimicrobial properties.

[0088] The 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. Example 1 - Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- propanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Alcohol 50 50 50 50

Lactic Acid 0.5 0.5 0.5 0.5

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-propanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 48.25 46.3 47.45 45.5

Total 100 100 100 100

Example 2 - Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,3- butanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Alcohol 50 50 50 50

Lactic Acid 0.5 0.5 0.5 0.5

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,3-butanediol 0.2 0.2 1 .0 1.0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 48.25 46.3 47.45 45.5

Total 100 100 100 100 Example 3 - Hair Lotion Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- pentanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Alcohol 50 50 50 50

Lactic Acid 0.5 0.5 0.5 0.5

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-pentanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 48.25 46.3 47.45 45.5

Total 100 100 100 100

Example 4 - Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- hexanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Alcohol 50 50 50 50

Lactic Acid 0.5 0.5 0.5 0.5

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-hexanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 48.25 46.3 47.45 45.5

Total 100 100 100 100

Example 5 - Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- heptanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Alcohol 50 50 50 50

Lactic Acid 0.5 0.5 0.5 0.5

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-heptanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 48.25 46.3 47.45 45.5

Total 100 100 100 100

Example 6 - Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- octanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Alcohol 50 50 50 50

Lactic Acid 0.5 0.5 0.5 0.5

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-octanediol 0.2 0.2 1 .0 1.0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 48.25 46.3 47.45 45.5

Total 100 100 100 100 Example 7 - Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- nonanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Alcohol 50 50 50 50

Lactic Acid 0.5 0.5 0.5 0.5

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-nonanediol 0.2 0.2 1 .0 1.0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 48.25 46.3 47.45 45.5

Total 100 100 100 100

Example 8 - Hair Lotion Formulation: !-propenal, 2-propenoic acid) and 1 ,2- decanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Alcohol 50 50 50 50

Lactic Acid 0.5 0.5 0.5 0.5

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-decanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 48.25 46.3 47.45 45.5

Total 100 100 100 100 Example 9 - Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-propanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Hydroxypropyl- 0.5 0.5 0.5 0.5 methylcellulose

Glycerol 6.5 6.5 6.5 6.5

Cetearyl alcohol 3.5 3.5 3.5 3.5

Glyceryl stearate 3.0 3.0 3.0 3.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-propanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 83.25 81 .3 82.45 80.5

Total 100 100 100 100

Example 10 - Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3-butanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Hydroxypropyl- 0.5 0.5 0.5 0.5 methylcellulose

Glycerol 6.5 6.5 6.5 6.5

Cetearyl alcohol 3.5 3.5 3.5 3.5

Glyceryl stearate 3.0 3.0 3.0 3.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,3-butanediol 0.2 0.2 1 .0 1.0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 83.25 81 .3 82.45 80.5

Total 100 100 100 100 Example 11 - Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-pentanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Hydroxypropyl- 0.5 0.5 0.5 0.5 methylcellulose

Glycerol 6.5 6.5 6.5 6.5

Cetearyl alcohol 3.5 3.5 3.5 3.5

Glyceryl stearate 3.0 3.0 3.0 3.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-pentanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 83.25 81 .3 82.45 80.5

Total 100 100 100 100

Example 12 - Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-hexanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Hydroxypropyl- 0.5 0.5 0.5 0.5 methylcellulose

Glycerol 6.5 6.5 6.5 6.5

Cetearyl alcohol 3.5 3.5 3.5 3.5

Glyceryl stearate 3.0 3.0 3.0 3.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-hexanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 83.25 81 .3 82.45 80.5

Total 100 100 100 100 Example 13 - Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-heptanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Hydroxypropyl- 0.5 0.5 0.5 0.5 methylcellulose

Glycerol 6.5 6.5 6.5 6.5

Cetearyl alcohol 3.5 3.5 3.5 3.5

Glyceryl stearate 3.0 3.0 3.0 3.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-heptanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 83.25 81 .3 82.45 80.5

Total 100 100 100 100

Example 14 - Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-octanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Hydroxypropyl- 0.5 0.5 0.5 0.5 methylcellulose

Glycerol 6.5 6.5 6.5 6.5

Cetearyl alcohol 3.5 3.5 3.5 3.5

Glyceryl stearate 3.0 3.0 3.0 3.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-octanediol 0.2 0.2 1 .0 1.0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 83.25 81 .3 82.45 80.5

Total 100 100 100 100 Example 15 - Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-nonanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Hydroxypropyl- 0.5 0.5 0.5 0.5 methylcellulose

Glycerol 6.5 6.5 6.5 6.5

Cetearyl alcohol 3.5 3.5 3.5 3.5

Glyceryl stearate 3.0 3.0 3.0 3.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-nonanediol 0.2 0.2 1 .0 1.0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 83.25 81 .3 82.45 80.5

Total 100 100 100 100

Example 16 - Hair Treatment Course Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2-decanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Hydroxypropyl- 0.5 0.5 0.5 0.5 methylcellulose

Glycerol 6.5 6.5 6.5 6.5

Cetearyl alcohol 3.5 3.5 3.5 3.5

Glyceryl stearate 3.0 3.0 3.0 3.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-decanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 83.25 81 .3 82.45 80.5

Total 100 100 100 100 Example 17 - Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- propanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Glycerol 5.0 5.0 5.0 5.0

Hydroxyethyl- 0.2 0.2 0.2 0.2 cellulose

Cetearyl alcohol 5.0 5.0 5.0 5.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-propanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 86.55 84.6 85.75 83.8

Total 100 100 100 100

Example 18 - Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3- butanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Glycerol 5.0 5.0 5.0 5.0

Hydroxyethyl- 0.2 0.2 0.2 0.2 cellulose

Cetearyl alcohol 5.0 5.0 5.0 5.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,3-butanediol 0.2 0.2 1 .0 1.0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 86.55 84.6 85.75 83.8

Total 100 100 100 100 Example 19 - Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- pentanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Glycerol 5.0 5.0 5.0 5.0

Hydroxyethyl- 0.2 0.2 0.2 0.2 cellulose

Cetearyl alcohol 5.0 5.0 5.0 5.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-pentanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 86.55 84.6 85.75 83.8

Total 100 100 100 100

Example 20 - Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- hexanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Glycerol 5.0 5.0 5.0 5.0

Hydroxyethyl- 0.2 0.2 0.2 0.2 cellulose

Cetearyl alcohol 5.0 5.0 5.0 5.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-hexanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 86.55 84.6 85.75 83.8

Total 100 100 100 100 Example 21 - Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- heptanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Glycerol 5.0 5.0 5.0 5.0

Hydroxyethyl- 0.2 0.2 0.2 0.2 cellulose

Cetearyl alcohol 5.0 5.0 5.0 5.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-heptanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 86.55 84.6 85.75 83.8

Total 100 100 100 100

Example 22 - Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- octanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Glycerol 5.0 5.0 5.0 5.0

Hydroxyethyl- 0.2 0.2 0.2 0.2 cellulose

Cetearyl alcohol 5.0 5.0 5.0 5.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-octanediol 0.2 0.2 1 .0 1.0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 86.55 84.6 85.75 83.8

Total 100 100 100 100 Example 23 - Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- nonanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Glycerol 5.0 5.0 5.0 5.0

Hydroxyethyl-

0.2 0.2 0.2 0.2 cellulose

Cetearyl alcohol 5.0 5.0 5.0 5.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2-

0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-nonanediol 0.2 0.2 1 .0 1.0

Preservatives,

1.0 1 .0 1 .0 1.0 fragrance, dye

Water 86.55 84.6 85.75 83.8

Total 100 100 100 100

Example 24 - Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- decanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Glycerol 5.0 5.0 5.0 5.0

Hydroxyethyl- 0.2 0.2 0.2 0.2 cellulose

Cetearyl alcohol 5.0 5.0 5.0 5.0

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-decanediol 0.2 0.2 1 .0 1 .0

Preservatives, 1 .0 1 .0 1 .0 1.0 fragrance, dye

Water 86.55 84.6 85.75 83.8

Total 100 100 100 100 Example 25 - Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- propanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Sodium Laureth- 12.0 12.0 12.0 12.0

Sulfate

Cocamidopropyl- 3.0 3.0 3.0 3.0 betaine

Disodium Laureth- 1 .50 1 .50 1.50 1 .50 sulfosuccinate

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-propanediol 0.2 0.2 1 .0 1 .0

Pearlescent agent 4.0 4.0 4.0 4.0

Preservatives,

fragrance, dye, 1 .0 1 .0 1 .0 1.0 thickeners

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100

Example 26 - Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3- butanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Sodium Laureth- 12.0 12.0 12.0 12.0

Sulfate

Cocamidopropyl- 3.0 3.0 3.0 3.0 betaine

Disodium Laureth- 1 .50 1 .50 1.50 1 .50 sulfosuccinate

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,3-butanediol 0.2 0.2 1 .0 1.0

Pearlescent agent 4.0 4.0 4.0 4.0

Preservatives,

fragrance, dye, 1 .0 1 .0 1 .0 1.0 thickeners

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100 Example 27 - Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- pentanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Sodium Laureth- 12.0 12.0 12.0 12.0

Sulfate

Cocamidopropyl- 3.0 3.0 3.0 3.0 betaine

Disodium Laureth- 1 .50 1 .50 1.50 1 .50 sulfosuccinate

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-pentanediol 0.2 0.2 1 .0 1 .0

Pearlescent agent 4.0 4.0 4.0 4.0

Preservatives,

fragrance, dye, 1 .0 1 .0 1 .0 1.0 thickeners

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100

Example 28 - Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- hexanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Sodium Laureth- 12.0 12.0 12.0 12.0

Sulfate

Cocamidopropyl- 3.0 3.0 3.0 3.0 betaine

Disodium Laureth- 1 .50 1 .50 1.50 1 .50 sulfosuccinate

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-hexanediol 0.2 0.2 1 .0 1 .0

Pearlescent agent 4.0 4.0 4.0 4.0

Preservatives,

fragrance, dye, 1 .0 1 .0 1 .0 1.0 thickeners

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100 Example 29 - Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- heptanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Sodium Laureth- 12.0 12.0 12.0 12.0

Sulfate

Cocamidopropyl- 3.0 3.0 3.0 3.0 betaine

Disodium Laureth- 1 .50 1 .50 1.50 1 .50 sulfosuccinate

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-heptanediol 0.2 0.2 1 .0 1 .0

Pearlescent agent 4.0 4.0 4.0 4.0

Preservatives,

fragrance, dye, 1 .0 1 .0 1 .0 1.0 thickeners

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100

Example 30 - Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- octanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Sodium Laureth- 12.0 12.0 12.0 12.0

Sulfate

Cocamidopropyl- 3.0 3.0 3.0 3.0 betaine

Disodium Laureth- 1 .50 1 .50 1.50 1 .50 sulfosuccinate

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-octanediol 0.2 0.2 1 .0 1.0

Pearlescent agent 4.0 4.0 4.0 4.0

Preservatives,

fragrance, dye, 1 .0 1 .0 1 .0 1.0 thickeners

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100 Example 31 - Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- nonanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Sodium Laureth- 12.0 12.0 12.0 12.0

Sulfate

Cocamidopropyl- 3.0 3.0 3.0 3.0 betaine

Disodium Laureth- 1 .50 1 .50 1.50 1 .50 sulfosuccinate

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-nonanediol 0.2 0.2 1 .0 1.0

Pearlescent agent 4.0 4.0 4.0 4.0

Preservatives,

fragrance, dye, 1 .0 1 .0 1 .0 1.0 thickeners

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100

Example 32 - Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,2- decanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Sodium Laureth- 12.0 12.0 12.0 12.0

Sulfate

Cocamidopropyl- 3.0 3.0 3.0 3.0 betaine

Disodium Laureth- 1 .50 1 .50 1.50 1 .50 sulfosuccinate

Lactic Acid 2.0 2.0 2.0 2.0

Poly(2-propenal, 2- 0.05 2.0 0.05 2.0 propenoic acid)

1 ,2-decanediol 0.2 0.2 1 .0 1 .0

Pearlescent agent 4.0 4.0 4.0 4.0

Preservatives,

fragrance, dye, 1 .0 1 .0 1 .0 1.0 thickeners

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100 Example 33 - Antimicrobial Activity of Compositions of the Invention

[0070] 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)

[0071] 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.

Table 2: Minimum Inhibitory Concentration Results for Examples 1-9

[0072] It is evident that the minimum inhibitory concentration determined in the presence of a C3-ioalkanediol is substantially lower than that determined with the poly(2-propenal, 2-propenoic acid). Moreover, there is a substantial improvement relative to the minimum inhibitory concentration of 1 ,2-hexanediol and 1 ,2-octanediol against E.coli (These have previously been reported to be 10,000 ppm and 6,300 ppm, respectively). The improved MIC is also observed throughout the series of C3-ioalkanediols, rather than being more evident with C6-ioalkanediols. These results indicate the synergistic antimicrobial activity of compositions according to the invention.

EXAMPLES 34 - 36

Placebo controlled Study

Trial with active at 500 ppm, 1000 ppm and 2000 ppm

[0073] 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.

Sample Description

[0074] A control placebo was prepared by combining the following components in the amounts by weight specified.

Component Weight %

Propylene glycol 10%

Ethanol 40%

Water to 100%

[0075] Corresponding 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.

Example No Concentration of PPPA

Control 0 ppm

Example 34 500 ppm

Example 35 1000 ppm

Example 36 2000 ppm

Test Material Evaluation Prerequisite

[0076] Prior to induction of a human test panel, toxicology, microbiology or in-vitro performance spectra may be required to assess the feasibility of commencement as dictated by an Institutional Review Board (IRB) described in Section 4.4. Test Material Handling

[0077] Upon arrival at the testing laboratory, the 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.

Population Demographics

Number of subjected enrolled in each arm of the study 6

Number of subjects completing study 6

Age Range 32 - 71

Sex Male 4

Female 2

Race Caucasian 6

[0078] Subjects with a history of any form of skin cancer, melanoma, lupus, connective tissue disease, diabetes or any disease that would increase risk associated with study participation.

[0079] Individuals diagnosed with chronic skin allergies or with history of hypersensitivity to cosmetics in general.

Methodology

[0080] Six healthy subjects (males and females) between the ages of 32 and 71 were inducted into this study. The subjects were pre-qualified for participation based on restrictions described in the inclusion/exclusion criteria in Section 4.1 and 4.2. In order to pre-condition the test sites and keep all treatments consistent during the study, the panelists were required to use only a baby shampoo product for a period of 7 days prior to study commencement and to use only the assigned test material throughout the study period.

Study Design:

Day 1 : Scalp debris collection (Baseline) Day 1-7: 7 day use with Placebo

Day 8: Scalp debris collection post Placebo

Day 8-15: 7 day use with active

Day 16: Scalp debris collection post active

[0081] All participants were instructed to apply test materials according to the following sponsor supplied directions:

Shampoo your hair using normal (not anti-dandruff) shampoo. Towel dry and then apply sufficient amount of the test product (about 5-7ml) to the scalp and massage in well. Use as a leave-on product once a day.

[0082] Participants were provided with a daily log and instructed to record the time of each application together with any subjective comments regarding product usage. Scalp debris collection via D-Squame surface sampling (described below) at fixed anatomical locations was employed prior to the initial application, after 8 days of the first application of control Placebo and again after 8 days of the first application of Example composition.

[0083] In addition, participants were asked to fill out a self-assessment questionnaire prior to the initial application of Placebo + Active and again after 7 days of treatment.

D-SQUAME Skin Sampling Discs

[0084] 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.

[0085] 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 .

Statistical Source Data

[0086] 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.

[0087] 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:

where:

x = Baseline (Day 1 ) - D-Squame Skin Sampling Discs test mean results

y = Post Treatment - Placebo (Day 8) D-Squame Skin Sampling Discs test mean results z = 1 - minimum D-Squame Skin Sampling Discs value (100% reduction)

or

x = Post Treatment - Placebo (Day 8) D-Squame Skin Sampling Discs test mean results y = Post Treatment - Active (Day 16) D-Squame Skin Sampling Discs test mean results z = 1 - minimum D-Squame Skin Sampling Discs value (100% reduction)

Results

[0088] The results are shown in the following tables and the attached drawings:

Example 34 Table 3 & 4 Fig. 1

Example 35 Table 5 & 6 Fig. 2

Example 36 Table 7 & 8 Fig. 3 In the drawings:

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.

Observations

[0089] No adverse effects or unexpected reactions of any kind were observed on any of the subjects.

Conclusions:

[0090] Within the limits imposed by the conduct and population size of the study described herein, the anti-dandruff test treatment with poly(2-propenal, 2-propenoic acid) demonstrated dramatic reduction in mean flakiness of scalp after 7 days use (Day 16). Observed differences in surface scaling of the site of the head treated with the test regimen are considered statistically significant with a maximum reduction observed on Day 16 of the study.

[0091] Subjective questionnaire responses corroborated the skin surface sampling data. Throughout the test period, the majority of test panelists perceived the test product to be an effective anti-dandruff product and that it reduced the conditions associated with dandruff. Table 3

*Statistically Significant

The flake reduction via D-Squame score (mean score) of the Example 34 composition - (500ppm) compared with the placebo, is shown as a column chart in Figure 1 .

[0092] Intensity of perceived dandruff related condition was ranked in the following scale:

0 None

1 Barely

2 - 3 Slightly

4 - 5 Definitely

6 - 7 Moderately

8 - 9 Dramatically

10 The Most Intense Imaginable

Table 4

DRY SCALP

PRE TREATMENT POST TREATMENT DAY 16

Mean 6.3 3.5

% Improvement 44.74%

Visual Dandruff Grading Summary via D-Squame Score

Table 5

*Statistically Significant

The flake reduction via D-Squame score (mean score) of the Example 35 composition - (l OOOppm) compared with the placebo, is shown as a column chart in Figure 2. Test Product Questionnaire Summary

[0093] Intensity of perceived dandruff related condition was assessed in the following scale:

0 None

1 Barely

2 - 3 Slightly

4 - 5 Definitely

6 - 7 Moderately

8 - 9 Dramatically

10 The Most Intense Imaginable

Table 6

Visual Dandruff Grading Summary via D-Squame Score

Table 7

^*Statistically Significant

The flake reduction via D-Squame score (mean score) of the Example 36 composition - (2000ppm) compared with the placebo, is shown as a column chart in Figure 3.

Test Product Questionnaire Summary

[0094] Intensity of perceived dandruff related condition was assessed in the following scale:

0 None

1 Barely

2 - 3 Slightly

4 - 5 Definitely

6 - 7 Moderately

8 - 9 Dramatically

10 The Most Intense Imaginable

Table 8

FURTHER FORUMLATIONS

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

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100

Example 39 - Skin Cleansing Formulations

% % % % % % % % %

Component % (w/w)

(w/w) (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) (w/w)

Sodium Laureth

6.80 6.30 8.00 8.50 5.40 1.80 Sulfate

Sodium Myreth

7.10 4.80 3.20 2.70

Sulfate

Cocoamidopropyl

5.20 4.70 3.00 2.80 5.10 4.80 6.40 3.70

Betaine

Sodium

3.50

Cocoamphoacetate

Decyl Glucoside 2.30 1.80 2.00 2.80 2.10 0.30

Lauryl Glucoside 0.60

Sodium Methyl

0.48 Cocoyl Ta urate

Disodium Cocoyl

0.50

Glutamate

Acrylates

2.40 2.20

Copolymer

PEG-200

Hydrogenated 0.40 2.70 0.40 0.40 1.00 0.50

Glyceryl Palmate

PEG-90 Glyceryl

0.14 0.30 0.70

Isostearate

PEG-120 Methyl

0.10

Glucose Dioleate

Laureth-2 0.01 0.03 0.07

Laureth-4 0.30

PEG-40

Hydrogenated 0.40 0.80 0.30 0.40 0.50 1.00 0.40 0.50 0.50

Castor Oil

PEG-7 Glyceryl

2.00 1.75 0.30 0.18 0.20 1.00 0.50 Cocoate

Glycol Distearate 0.60 0.60 0.30

Styrene/Acrylate

0.40

Copolymer

Glycerol 0.30 8.60 0.30 1.70

Sorbitol 17.50

Polyquaternium-7 0.30

Polyquaternium-10 0.20 0.10 0.10

Sodium Chloride 0.15 0.40 0.80 0.60

Acrylates/CI O-30

Alkyl Acrylate 0.90

Crosspolymer

Xanthan Gum 0.25

Carbomer 1.20

Menthol 0.10 Polyethylene 0.40

Poly(2-propenal, 2-

0.01 0.03 0.10 0.25 0.50 0.01 0.03 2.00 0.75 1.00 propenoic acid)

Natrium Benzoate 0.45 0.45 0.40 0.40

Natrium Salicylate 0.40 0.20

Methyl Parabene 0.35 0.30

Propyl Parabene 0.35 0.20

1 ,2-Pentadiol 0.20

Piroctone Olamine 0.10

1 ,2-Hexandiol 0.20

Phenoxyethanol 0.90

Trisodium EDTA 0.20 0.20 0.10

Potassium Sorbate 0.10

Perfume 0-1 0-1 0-1 0-1 0-1 0-1 0-1 0-1 0-1 0-1 ad ad ad ad ad

Water ad 100 ad 100 ad 100 ad 100 ad 100

100 100 100 100 100

Example 40: Hair Care Cleansing Formulations

Example 41 : Hair Care Conditioner Formulations

Example 42: Hair Conditioner Formulations

Perfume 0.6 0.7 0.7 0.7 0.2 0.7 0.7 0.7

Polyquaternium-89 1.5 1 1.2 1 .5 1 2 1.5 1

Example 43: Water in Oil Emulsion Formulations

Example 44: Water in Silicon Emulsion Formulations

Glycerol 3 5 10 15 1.5

Citric Acid 0.2 0.1 0.2 0.3 1

Sodium citrate 1 0.1 0.4 0.9 2.5

Perfume q,s, q,s, q,s, q,s, q,s,

Poly(2-propenal, 2-propenoic acid) 0.1 0.25 0.1 0.05 0.5

N-Lauryl-L-Arginine Thyl Ester

0.5

Monochloride

Benzethoniumchloride 0.5

DMDM Hydantoin 0.1

Diazolidinyl Urea 0.25

Microcrystalline Cellulose 1 0.1 0.5 0.25 0.1

Silicon Elastomer Gel 20 10

Benzylalcohol 0.05 0.1

Modified starch 2.5 0.15

Water ad 100 ad 100 ad 100 ad 100 ad 100

Example 45: Hydrodispersion Formulations

Water ad 100 ad 100 ad 100 ad 100 ad 100

Example 46: Silicon in Water Emulsion Formulations

Example 47: Oil in Water Formulations

% % % % % % % %

Component

(w/w) (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) (w/w)

Glycerylsteratcitrate 1 0.5 0.1 0.5 0.3 0.2 0.7 0.3

Polyethylenglycol(20)cetearyleth

10 1 5 4

er

Triglycerinmethylglucosedistearat 2.5 2.5

Pigments 5 15

Cyclomethicone 1 5 20

Dimethicone 0.5 3 0.75 1.5 0.2 5 1.5 3

Behenyl alcohol 1 2 1 0.2 2 0.2

Dicaprylylcarbonat 3 5 10 15 5 10 5

Stearyl alcohol 1 0.2 2 0.5

Cetylstearyl alcohol 1 1 0.2 1 1 0.2

Tocopherol 0.5 0.25

Example 48: Styling Gel Formulations

Methylcellulose

Cetearyl Alcohol +

0.2

Behentrimonium Chloride

Stearyl Alcohol 4 7.3152 7.776 7.776 7.776

Cetrimonium Chloride 4 0.4

Dicaprylyl Ether 1

Distearoylethyl

Hydroxyethylmonium

2 2 2.86

Methosulfate + Cetearyl

Alcohol

Oryzanol 0.05 0.05 0.05 0.05

DMDM Hydantoin 0.4

Poly(2-propenal, 2-

0.1 0.2 0.15 0.2 0.3 0.1 0.05 0.1 0.5 propenoic acid)

1 ,2-Pentadiol 0.20

Piroctone Olamine 0.10

1 ,2-Hexandiol 0.20

Phenoxyethanol 0.90

Ethanol 5.00

Trisodium EDTA 0.20 0.40

Potassium Sorbate 0.10

Silicone Quaternium-16 +

Undeceth-1 1 + Butyloctanol 2

+ Undeceth-5

Cyclomethicone 2

Palmitamidopropyltrimonium

3 1.66

Chloride + Propylene Glycol

Coco Betaine 0.85 3.22 3.22 3.22

Polyquaternium-68 +

Phenoxyethanol and 7.5 3.75 1.875 1.875 Parabenes

Stearamidopropyl

2.2 2.2 2.2 2.2 Dimethylamine

Parfum 0.6 0.7 0.7 0.7 0.2 0.7 0.7 0.7 0.7

Polyquaternium-89 1.5 1 1.2 1.5 1 20 10 5 5

Example 49: Hairspray Aerosol Formulations

% % % % % % % % %

Component

(w/w) (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) (w/w) (w/w)

Octylacrylamide/

Acrylates/Butylamino-ethyl 3.5 2 2 1.75 1.75

Methacrylate Copolymer

PVP 7 7 5 5

Ethanol 50 50 30 50 50 50 50 50 50

Aminomethylpropanole 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6

Silicone 0.1 0.5 1 0.05 0.1 0.1 0.5 1 1

Vitamins 0.1 0.25 0.1 0.25 0.1 0.1 0.25 0.05 0.05

Perfume 0, 5 0, 4 0, 3 0, 2 0.1 0.2 0.3 0.4 0.4

Propan / Butan 35 35 35

Dimethylether 40 40 40 40 40 40 Poly(2-propenal, 2-propenoic acid) 0.1 0.2 0.15 0.2 0.3 0.1 0.75 0.5 1

1 ,2-Pentadiol 0.20

Piroctone Olamine 0.10

1 ,2-Hexandiol 0.20

Phenoxyethanol 0.90

1 ,2-Pentadiol 0.25

1 ,2-Hexandiol 0.50

Ethanol 5.00

Trisodium EDTA (aq) 0.20 0.40

Potassium Sorbate 0.10

ad ad ad ad ad ad ad ad ad

Aqua

100 100 100 100 100 100 100 100 100

Example 50: Styling Foam Formulations

Example 51 : Deo AT Formulations

Example 52: Oil in Water SPF 15 Formulations

N-Lauryl-L-Arginine

Thyl Ester

Monochloride

Benzethoniumchloride 0.6

1 ,2-Pentadiol 0.5

Glyceryl Stearate 2.4 1.2 1

Stearic Acid 2.5 3

PEG-40 Stearate 0.5

Polyglyceryl-3

Methylglucose 2 1.75 2.5

Distearate

Glyceryl Stearate

2 1.75 2.5 2.5 Citrate

Sodium Stearoyl

0.5 0.4 0.2 0.2

Glutamate

Sucrose Polystearate

+ Hydrogenated 3 2.5 1 1

Polyisobutene

ad ad ad ad ad ad ad ad ad ad ad ad ad ad

Water

100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cera icrocristallina

+ Paraffinum 1.5 2 1.5

Liquidum

Glycerol 6 4 8 4 6 10 4 6 10 1 8 6 2 12

Cetyl Alcohol 1.25 1 1 1.5 1 3 2 4 4

0.02

BHT

5

Dimethicone 2 1 2 3 4 4

Cyclomethicone 6 5 4 4 4

Hydrogenated Coco-

1 1 3 4 2 2 Glycerides

Simmondsia

1.5 4

Chinensis Oil

C12-15 Alkyl

1.5 1 8 3

Benzoate

Dicaprylyl Carbonate 3 2 2 5 5 3 6 6

Caprylic/Capric

2, 8 2 2.7 2.5 3 3 Triglyceride

Cyclomethicone +

4 3 5 5

Dimethiconol

Octyldodecanol 0.5 1

Dicaprylyl Ether 1

Ethylhexyl Cocoate 5 4 6 6

Tridecyl Stearate +

Tridecyl Trimellitate +

Dipentaerythrityl 2 2 1.5 1.5 Hexacaprylate/Hexac

a prate

Butyrospermum Parkii

4 2 2.5 2.5 Butter

Lanolin Alcohol

0.1 0.2 0.1 0.1 (Eucerit®)

Stearyl Alcohol 1.25 1 3 4 3.5 3.5

0.07

Carbomer 0.3 0.1 0.1 0.25 0.15 0.15 0.2 0.2 0.4 0.35 0.45 0.45

5

Acrylates/C10-30

Alkyl Aery late 0.4 0.3 0.2 0.2

Cross polymer

Chondrus Crispus 0.5 0.4 0.7 0.7

Sodium Hydroxide aq q.s. q.s. q.s. q.s. q.s. q.s. q.s. q.s. q.s. q.s. q.s. q.s. q.s. q.s. 45%

Ethyl hexylglycerol 0.5 0.25 0.5 0.25 1 1

Talc 3 4

Ammonium

Acryloyldimethyltaurat 1 0.75 1.5 1.5

e/VP Copolymer

Tetrasodium

0.2

Iminodisuccinate

EDTA 0.2 0.2 0.2 0.1 0.2 0.2 0.2

Macadamia Ternifolia 1 0.75 1.3 1.3

Sodium Polystyrene

0.3 0.25 0.4

Sulfonate

Ethylhexyl

Methoxycinnamate + 5 3 4 9 9

BHT

Ethylhexyl Salicylate 2 4.5 4 3

Butyl

Methoxydibenzoylmet 2 2 2 1 2.5 1.5 5

hane

2-(4'-Diethylamino-2'- hydoxybenzoyl)-

3 1 4 5

benzoesaurehexylest

er

Phenylbenzimidazole

3 0.5 4

Sulfonic Acid

Diethylhexyl Butamido

4

Triazone

Titanium Dioxide +

Alumina + 0.45 4

Simethicone

Titanium Dioxide 2

Ethylhexyl Triazin 2 3 1

Polysilicon-15 3

Bis-

Ethylhexyloxyphenol 0.5 Methoxyphenyltriazin

Octocrylene 5 5

Example 53: SPF>15 Formulations

Component % (w/w) % (w/w) % (w/w) % (w/w) % (w/w) % (w/w)

Tocopheryl Acetate 0.10 0.10 0.3 0.10 0.2 0.10

Stearyl Alcohol 0.50 0.50

Myristyl Myristate 1.00 1.20 1.50 1 .70

Hydrogenated Coco-Glycerides 1.00 1 .00

Dicaprylyl Carbonate 2.00 2.00

C12-15 Alkyl Benzoate 5.00 5.00 6.50 6.50

Butylene Glycol Dicaprylate/Dicaprate 9.00 9.00 8.50 8.50

C18-36 Acid Triglyceride 1 .00 1.00

Cetyl Alcohol 2.20 2.20

Octyldodecanol 5.50 5.50

Glyceryl Stearate Citrate 2.00 2.00

Ceteareth-20 1.00 1.00 Cetearyl Alcohol + PEG-40 Castor Oil +

2.00 2.00 Sodium Cetearyl Sulfate

Glyceryl Stearate SE 0.65 0.65

Tapioca Starch + Aqua 1.00 1.20

VP/Hexadecene Copolymer 0.50 0.40 0.60 0.50

Perfume 0.40 0.40 0.30 0.30 0.40 0.40

Glycerol 8.60 8.60 5.00 5.00 0.9 0.9

Citric Acid 0.09 0.09

Sodium Citrate 0.18 0.18

Aqua + Sodium Hydroxide 0.03 0.03 9.00 0.90 0.60 0.60

Methylparaben 0.05

Phenoxyethanol 0.60

Methylpropanediol 1 .00

Ethylhexylglycerol 0.50

N-Lauryl-L-Arginine Thyl Ester

1.80

Monochloride

Octopirox 0.05

Poly(2-propenal, 2-propenoic acid) 0.20 0.20 0.20 0.20 0.20 0.20

Acrylates/C 10-30 Alkyl Acrylate

0.05 0.05 0.40 0.40 0.40 0.40 Crosspolymer

Xanthan Gum 0.40 0.50 0.40 0.50

Aqua ad. 100 ad. 100 ad. 100 ad. 100 ad. 100 ad. 100

Alcohol Denat. 4.00 5.00 10.00 5.00 8.00 5.00

Aqua + Trisodium EDTA 1.00 1.00 1.00 1.00 1.00 1.00

Ethylhexyl Methoxycinnamate + BHT 0.50 0.50

Octocrylene 8.00 8.00 7.00 8.00 4.50 5.00

Bis-Ethylhexyloxyphenol Methoxyphenyl

1.50 1.50 2.50 3.00 2.30 2.50 Triazine

Butyl Methoxydibenzoylmethane 4.50 4.50 4.50 4.50 4.50 4.50

Diethylhexyl Butamido Triazone 1.00 1 .00

Titanium Dioxide +

3.00 5.00 2.00 3.00 Trimethoxycaprylylsilane

Ethylhexyl Salicylate 4.50 4.50

Phenylbenzimidazole Sulfonic Acid 1.50 1.50 2.00 2.50

Claims

CLAIMS:

1 . An antifungal composition for topical treatment of dermatitis associated with fungal infections comprising a polymer of 2-propenal and a dermatologically acceptable carrier.

2. The antifungal composition according to claim 1 for topical treatment of a dermatitis selected from the group consisting of dandruff, seborrhoeic dermatitis and dermaphytoses.

3. The antifungal composition according to claim 2 for topical treatment of dandruff.

4. The antifungal composition according to any one of the previous claims wherein the polymer of 2-propenal is formed by anionic polymerization.

5. The antifungal composition according to any one of the previous claims wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

6. The antifungal composition for topical treatment according to any one of the previous claims wherein the composition comprises from 0.01 to 10% and preferably from 0.05 to 5% by weight of the polymer of poly(2-propenal) based on the total weight of the composition.

7. The antifungal composition for topical treatment according to any one of the previous claims in a form selected from the group consisting of formulated as a lotion, cream, moisturizer, hair gel, hair mousse, shaving cream, 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.

8. The antifungal composition for topical treatment according to any one of the previous claims in a form selected from the group consisting of formulated as a lotion, cream, a hair rinse, a hair spray, a shampoo and a conditioner.

9. Use of a polymer of 2-propenal in manufacture of a topical medicament for treatment of dermatitis associated with a fungal infection.

10. Use of a polymer of 2-propenal according to claim 10 wherein the dermatitis associated with a fungal infection is selected from the group consisting of dandruff, seborrhoeic dermatitis and dermaphytoses.

1 1 . Use according to claim 9 or claim 10 wherein the dermatitis associated with a fungal infection is dandruff.

12. The use according to any one of claims 9 to 1 1 wherein the topical medicament comprises a dermatologically acceptable carrier.

13. The use according to any one of claims 9 to 12 wherein the polymer of 2-propenal is preferably a formed by anionic polymerization.

14. The use according to any one of claims 9 to 13 wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid), preferably formed by oxidation of a poly(2- propenal) so as to introduce carboxyl groups, more preferably comprising from 0.1 to 5 moles of carboxyl groups per kilogram of polymer.

15. The use according to any one of claims 9 to 14 wherein the polymer of 2-propenal is present in the topical medicament in an amount of from 0.01 to 10% by weight of the topical medicament and preferably from 0.05 to 5% by weight of the topical medicament polymer of poly(2-propenal).

16. A method of treatment of dermatitis associated with fungal infections comprising the topical application of an antifungal composition comprising a polymer of 2- propenal and a dermatologically acceptable carrier.

17. The method according to claim 1 for topical treatment of a dermatitis selected from the group consisting of dandruff, seborrhoeic dermatitis and dermaphytoses.

18. The method according to claim 17 for topical treatment of dandruff.

19. The method according to any one of claims 16 to 18 wherein the polymer of 2- propenal is formed by anionic polymerization.

20. The method according to any one of claims 16 to 19 wherein the polymer of 2- propenal is poly(2-propenal, 2-propenoic acid).