Anti-dandruff composition

Abstract

An anti-dandruff composition is disclosed that includes a small amount of piroctone olamine, which synergistically interacts with benzoic acid or its salt and itaconic acid or its ester. The composition may be used for personal cleansing, and is particularly preferably delivered as a shampoo or hair conditioner.

Description

Technical Field

[0001] The present invention relates to an anti-dandruff composition. More particularly, the present invention relates to personal care or cleansing compositions, such as those that provide benefits to hair and scalp, including active substances that interact synergistically for an anti-dandruff effect.

Background Art

[0002] The present invention relates to anti-dandruff compositions that are particularly useful for personal care and cleansing of hair and scalp. Hair care compositions generally provide a cleansing effect, a conditioning effect, or a combination of the two. Such compositions typically contain one or more cleansing surfactants that generally assist in the cleaning of hair and / or scalp, free of undesirable dirt, particles, and fatty substances.

[0003] Furthermore, hair care compositions also provide an anti-dandruff effect. Dandruff is a problem that affects many people around the world. This condition appears when clumps of dead skin cells fall off the scalp. These are white and result in an aesthetically unpleasant appearance. One factor contributing to dandruff is a specific member of the Malassezia yeast (a form of fungus). To combat these, anti-dandruff products have been developed in the form of hair cleansing shampoos. Examples of known anti-dandruff shampoos include sodium lauryl ether sulfate (an ethoxylated anionic surfactant) in combination with an anti-dandruff agent. Typical anti-dandruff agents used in hair care are zinc pyrithione (e.g., ZPTO), octopirox (piroctone olamine), azole antimicrobials (e.g., climbazole), selenium sulfide, and combinations thereof. One problem with octopirox was its high cost and the limitation of its effect at low concentrations.

[0004] The present inventors have attempted to solve the above problems regarding the utilization of the effect of octopirox while ensuring that the cost of the product for consumers is kept low by enhancing the effect at a low concentration. The present inventors have achieved this by combining itaconic acid or its ester, which has been found to synergistically combine with a very low concentration of octopirox due to its excellent antifungal effect, with benzoic acid or its salt.

[0005] To the best of the present inventors' knowledge, the antimicrobial composition containing the combination claimed herein has not been known or published heretofore.

Summary of the Invention

Problems to be Solved by the Invention

[0006] Therefore, an object of the present invention is to provide an even higher dandruff-preventing effect from a very low concentration of octopirox.

Means for Solving the Problems

[0007] According to a first aspect, there is disclosed an antimicrobial composition comprising itaconic acid or its ester; benzoic acid or its salt; and piroctone olamine.

[0008] Another aspect of the present invention relates to a method for inhibiting the growth of M. furfur, which comprises applying the composition of the first aspect to a desired skin surface.

[0009] Yet another aspect of the present invention relates to the use of a composition comprising itaconic acid or its ester, benzoic acid or its salt; and piroctone olamine in preventing dandruff.

Modes for Carrying Out the Invention

[0010] These and other aspects, features and advantages will become apparent to those skilled in the art upon reading the following detailed description and the appended claims. To avoid doubt, any feature of one aspect of the invention may be utilized in any other aspect of the invention. The term "comprising" is intended to mean "including" but does not necessarily mean "consisting of" or "composed of". In other words, the recited steps or options need not be exhaustive. It should be noted that the examples shown in the following description are intended to clarify the invention and are not intended to limit the invention to those examples themselves. Similarly, all percentages are weight / weight % unless otherwise indicated. All numbers in this specification and the claims, which indicate amounts of materials or reaction conditions, physical properties of materials and / or uses, are to be understood as being modified by the term "about", except in the case of operating and comparative examples, or where otherwise explicitly stated. A numerical range expressed in the form "x to y" is to be understood as including x and y. It is understood that all ranges combining different endpoints are contemplated when multiple preferred ranges for a particular feature are recited in the form "x to y". In other words, in any specification of a numerical range, any particular upper limit can be associated with any particular lower limit.

[0011] Notwithstanding the fact that the claims may be found to be multiply dependent or non-redundant, the disclosure of the invention found herein is multiply dependent upon one another and should be considered to encompass all embodiments as found in the claims.

[0012] Where features are disclosed with respect to particular aspects of the invention (e.g., a composition of the invention), such disclosure should be considered to apply, with the necessary modifications, to any other aspect of the invention (e.g., a method of the invention).

[0013] As used herein, "anti-dandruff composition" means a composition for topical application to the skin, hair and / or scalp of a mammal, particularly a human, to eliminate or minimize the population of fungal microorganisms thereon. Such compositions include any product applied to the human body to also improve appearance, cleansing, odor control or general aesthetics. The compositions of the present invention can be in the form of a liquid, lotion, cream, foam, scrub, gel or bar. Non-limiting examples of such compositions include a wash-off shampoo, a shampoo-conditioner, a shower gel, a hair care liquid or gel or bar. The composition of the present invention is most preferably a conventional lotion or semi-liquid form of shampoo or hair conditioner.

[0014] The present invention relates to an anti-dandruff composition comprising piroctone olamine; itaconic acid or its ester; and benzoic acid or its salt.

[0015] Piroctone olamine or 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-(1H)pyridinone, 2-aminoethanol salt or octopirox is a heterocyclic compound and ethanolamine salt of the hydroxamic acid derivative piroctone. This is often used in anti-dandruff shampoos as an alternative to the commonly used compound zinc pyrithione. It is a white or slightly yellow crystalline powder. It is soluble in a 10% aqueous ethanol solution, an aqueous solution containing a surfactant, or soluble in 1% - 10% ethanol. Piroctone olamine is an anti-dandruff active ingredient that soothes the inflamed scalp and reduces flaking. Piroctone olamine has special functions such as thickening, preservation, and body odor removal.

[0016] Piroctone olamine has the following structure:

Chemical formula

[0017] The composition preferably contains 0.0001 to 1%, more preferably 0.0001 to 0.01%, still more preferably 0.0001 to 0.0006%, and even more preferably 0.0001 to 0.0003% of piroctone olamine, based on the weight of the composition.

[0018] Itaconic acid is an organic unsaturated dicarboxylic acid. Itaconic acid is methacrylic acid in which one of the methyl hydrogens is replaced by a carboxylic acid group. Another name for itaconic acid is 2 - methylene succinic acid or methylene butanedioic acid. The molecular weight of itaconic acid is 130.1 g / mol. Itaconic acid is available as a dry white powder. Its solubility in water is 1 g / 12 ml. Itaconic acid is naturally produced by various fungi such as Aspergillus terreus, Ustilago zeae, and Ustilago maydis, as well as by yeast Candida species. Aspergillus terreus is used in the industrial production of itaconic acid. Polymers of itaconic acid are widely used in cleaning and hygiene, energy and industry, surface coatings, and agriculture. Polymers of itaconic acid are widely used in hair conditioning gels and odor control products.

[0019] Itaconic acid has the following structure:

Chemical formula

[0020] Itaconic acid esters can also be used in the composition of the present invention. Suitable itaconic acid esters are dimethyl itaconate or dibutyl itaconate, preferably dimethyl itaconate.

[0021] The composition of the present invention contains benzoic acid or its salt. A suitable salt of benzoic acid that can be included is sodium benzoate.

[0022] Benzoic acid is a compound containing a benzene ring core with a carboxylic acid substituent. Benzoic acid has a role as an antimicrobial food preservative. Benzoic acid appears as a white crystalline solid. Benzoic acid is sparingly soluble in water. Most commercially available benzoic acid is produced by the reaction of toluene with oxygen in the liquid phase at a temperature of about 200 °C in the presence of cobalt salts and manganese salts as catalysts. Acidic foods and beverages such as fruit juices (citric acid), carbonated beverages (carbon dioxide), soft drinks (phosphoric acid), pickles (vinegar), etc. are preserved using benzoic acid. The structure of benzoic acid is as follows: [Chemical formula]

[0023] The weight ratio of itaconic acid or its ester to benzoic acid or its salt is preferably in the range of 1:9 to 9:1.

[0024] The concentration of itaconic acid or its ester enabling the anti-dandruff effect is preferably in the range of 0.01 to 2%, more preferably 0.1 to 2% of the weight of the composition.

[0025] Benzoic acid or its salt is preferably contained in the composition in the range of 0.01 to 2%, preferably 0.1 to 2% of the weight of the composition. Preferably, the total amount of itaconic acid or its ester and benzoic acid or its salt is contained in the composition in the range of 0.15 to 3%, preferably 0.2 to 2% of the weight of the composition.

[0026] The weight ratio of piroctone olamine to itaconic acid or its ester is preferably in the range of 1:10 to 1:250.

[0027] The weight ratio of piroctone olamine to benzoic acid or its salt is preferably in the range of 1:10 to 1:250.

[0028] The composition of the present invention preferably further comprises a cosmetically acceptable carrier. The carrier is preferably selected such that the composition of the present invention can be delivered for use as a personal cleansing composition. According to one aspect, the cosmetically acceptable carrier is water or an aqueous solution. According to another preferred aspect, the carrier further comprises a surfactant. The cosmetically acceptable vehicle is such that the composition can be formulated as a shampoo, conditioner, body wash, hand wash or facial wash product, cream, lotion, gel, powder, ointment or soap bar.

[0029] According to a further preferred aspect of the present invention, the composition is any one of a shampoo, hair conditioner or body wash product, most preferably a shampoo or hair conditioner composition. When formulated as such, the composition further comprises a cosmetically acceptable carrier selected from anionic surfactants, cationic surfactants or amphoteric surfactants or zwitterionic surfactants.

[0030] According to a particularly preferred aspect of the present invention, the composition is a shampoo. The composition of the present invention, particularly the shampoo, is formulated with anionic surfactants such as alkyl sulfates and / or ethoxylated alkyl sulfate surfactants. These anionic surfactants are preferably present at a level of 1 to 20%, preferably 2 to 16%, more preferably 3 to 16% by weight of the composition. Preferred alkyl sulfates are preferably C8-18 alkyl sulfates in the form of salts with solubilizing cations such as sodium, potassium, ammonium or substituted ammonium, more preferably C12-18 alkyl sulfates.

[0031] Preferred alkyl ether sulfates have the formula: RO(CH2CH2O) n SO -3 M; In the formula, R is an alkyl or alkenyl having 8 to 18 (preferably 12 to 18) carbon atoms, n is a number having an average value greater than at least 0.5, preferably 1 to 3, more preferably 2 to 3, and M is a solubilizing cation such as sodium, potassium, ammonium or substituted ammonium. An example is sodium lauryl ether sulfate (SLES). SLES having an average ethoxylation degree of 0.5 to 3, preferably 1 to 3 is particularly preferred.

[0032] The shampoo composition according to the present invention is cosmetically acceptable and may contain one or more additional anionic cleansing surfactants suitable for topical application to the hair.

[0033] The composition of the present invention preferably further contains an amphoteric surfactant, preferably a betaine surfactant, preferably an alkylamidopropyl betaine surfactant, such as cocoamidopropyl betaine. In a preferred embodiment, the composition contains 0.1 to 10% by weight, preferably 0.5 to 8% by weight, more preferably 1 to 5% by weight of the betaine surfactant.

[0034] In order to enhance the deposition of the active substance from the composition of the present invention, particularly from the shampoo, a cationic polymer is generally included. In the present invention, it is also preferred that the composition further contains 0.01 to 2.0% of the cationic polymer. The cationic polymer is preferably guar hydroxypropyltrimonium chloride. The guar polymer mainly contains galactomannan polymer chains. This polymer is available with various molecular weights and degrees of cationic substitution depending on the degree of hydrolysis and cationization of the guar. The cationic polymer is preferably present at 0.04 to 0.5%, more preferably 0.08 to 0.25% of the weight of the composition.

[0035] The pH of the composition is preferably 4.0 or higher, more preferably in the range of 5.0 to 10.0.

[0036] Preferably, the composition of the present invention further contains a suspending agent. Suitable suspending agents are selected from polyacrylic acid, cross-linked polymers of acrylic acid, copolymers of acrylic acid and hydrophobic monomers, copolymers of carboxylic acid-containing monomers and acrylic esters, cross-linked copolymers of acrylic acid and acrylate esters, heteropolysaccharide gums, and crystalline long-chain acyl derivatives.

[0037] When included, the suspending agent is present in the shampoo composition of the present invention at a level of 0.1 to 10%, preferably 0.5 to 6%, more preferably 0.5 to 4% by the total weight of the suspending agent based on the total weight of the composition.

[0038] The composition of the present invention may contain other components for enhancing performance and / or consumer acceptability. Such components include fragrances, dyes and pigments, pH adjusters, pearlescent or opacifying agents, viscosity adjusters, preservatives, and natural hair nutrients such as plant components, fruit extracts, sugar derivatives, and amino acids.

[0039] The composition of the present invention is preferably aqueous. The composition of the present invention preferably contains a large amount of water, 70 to 95% of the weight of the composition.

[0040] When a conditioning effect is brought about via the composition of the present invention, the composition is called a hair conditioner. Typically, the most common conditioning agents used in hair care compositions are water-insoluble oily materials such as mineral oil, and naturally occurring oils such as triglycerides and silicone polymers. The conditioning effect is achieved by the oily material depositing on the hair to form a film, which makes the hair easier to comb when wet and easier to handle when dry. Particularly useful conditioning agents are silicone compounds, preferably non-volatile silicone compounds. Advantageously, the compositions herein may contain one or more silicones. Silicones are conditioning agents found in dispersed particulate form or suspended particulate form. They are intended to deposit on the hair and remain after rinsing the hair with water. Suitable silicone oils may include polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, polyether silicone copolymer and mixtures thereof. Amino silicones are often formulated with shampoo compositions. Amino silicones are silicones containing at least one primary amine group, secondary amine group, tertiary amine group or quaternary ammonium group. High molecular weight silicone gums can also be utilized. Another useful type is cross-linked silicone elastomers such as dimethicone / vinyl / dimethicone copolymers (e.g., Dow Corning 9040 and 9041).

[0041] When present, the amount of silicone in the composition can range from about 0.1 to about 10% by weight, preferably from about 0.1 to about 8% by weight, more preferably from about 0.3 to about 5% by weight of the hair care composition.

[0042] The pH of the composition is preferably 4.0 or higher, more preferably in the range of 5.0 to 7.0.

[0043] Hair conditioning compositions typically contain a conditioning surfactant selected from cationic surfactants used alone or in combination. Suitable cationic surfactants for use in the conditioner compositions according to the present invention include cetyltrimethylammonium chloride, behenyltrimethylammonium chloride, cetylpyridinium chloride, tetramethylammonium chloride, tetraethylammonium chloride, octyltrimethylammonium chloride, dodecyltrimethylammonium chloride, hexadecyltrimethylammonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, didodecyldimethylammonium chloride, dioctadecyldimethylammonium chloride, tallowtrimethylammonium chloride, dihydrogenated tallowdimethylammonium chloride (e.g., Arquad 2HT / 75 from Akzo Nobel), coco trimethylammonium chloride, PEG-2-oleammonium chloride and their corresponding hydroxides.

[0044] The most preferred cationic surfactants for use in the compositions are stearamidopropyldimethylamine, behentrimonium chloride or stearyltrimethylammonium chloride. In the conditioners of the present invention, the level of cationic surfactant generally ranges from 0.1% to 5%, preferably 0.5 to 2.5% by weight of the composition.

[0045] The hair conditioning compositions of the present invention may also preferably further contain a fatty alcohol. The combined use of a fatty alcohol and a cationic surfactant in the conditioning composition is considered particularly advantageous because it results in the formation of a lamellar phase in which the cationic surfactant is dispersed.

[0046] The level of fatty alcohol in the conditioner of the present invention is generally in the range of 0.5 to 10%, preferably 0.1% to 8%, more preferably 0.2% to 7%, and most preferably 0.3% to 6% by weight of the composition. The weight ratio of the cationic surfactant to the fatty alcohol is preferably 1:1 to 1:10, more preferably 1:1.5 to 1:8, and optimally 1:2 to 1:5.

[0047] The composition of the present invention can be used for skin care, such as for washing the body, hands or face. The antimicrobial composition may further contain a surfactant. Preferred surfactants are nonionic surfactants, for example, when the product is in liquid form, containing 1 to 8 ethylene oxide groups, C8 - C 22 , preferably C8 - C 16 fatty alcohol ethoxylates. The surfactant is preferably selected from primary alkyl sulfates, secondary alkyl sulfonates, alkyl benzene sulfonates or ethoxylated alkyl sulfates. The composition may further contain an anionic surfactant, for example, an alkyl ether sulfate, preferably having 1 to 3 ethylene oxide groups derived from either a natural source or a synthetic source, and / or a sulfonic acid. Sodium lauryl ether sulfate is particularly preferred. Alkyl polyglucosides, preferably those having a carbon chain length of C6 - C16, may also be present in the composition.

[0048] Thus, in a highly preferred embodiment, the antimicrobial composition contains a surfactant selected from the group consisting of anionic surfactants, fatty acid amides, alkyl sulfates, linear alkyl benzene sulfonates and combinations thereof.

[0049] When a surfactant is present, the antimicrobial composition preferably contains 1 to 90% by weight of the surfactant in the composition.

[0050] When a surfactant is used, a particularly preferred surfactant is soap. Soap is a surfactant suitable for personal washing applications of the antimicrobial composition of the present invention. Soap is preferably C8 - C24 Soap, more preferably C 10 ~C 20 Soap, most preferably C 12 ~C 18 is soap. The cation of the soap can be an alkali metal, an alkaline earth metal or ammonium. Preferably, the cation of the soap is selected from sodium, potassium or ammonium. More preferably, the cation of the soap is sodium or potassium.

[0051] A typical fatty acid blend consisted of 5 - 30% coconut fatty acid and 70 - 95% fatty acids by weight of the soap. For example, fatty acids derived from other suitable oils / fats such as peanut, soybean, tallow, palm, palm kernel, etc. can also be used in other desired proportions.

[0052] The soap of the present invention, when present, is preferably present in an amount of 1 - 90%, preferably 10 - 85%, more preferably 25 - 75% by weight of the composition.

[0053] Preferred compositions can contain other known ingredients such as fragrances, pigments, preservatives, softeners, sunscreens, emulsifiers, gelling agents and thickening agents. The selection of these ingredients depends largely on the form of the composition.

[0054] Water is a preferred carrier. Water, when present, is preferably present in at least 1%, more preferably at least 2%, even more preferably at least 5% by weight of the composition. When water is the carrier, a preferred liquid composition contains 10 - 99.8% by weight of water.

[0055] According to the present invention, non - therapeutic uses of the composition for providing an anti - dandruff effect are also disclosed. The following non - limiting examples further illustrate preferred embodiments of the present invention. In the examples, and throughout this specification, all percentages are based on total weight unless otherwise indicated. [Examples]

[0056] [Examples 1 - 15] Antifungal effect of the composition according to the present invention: As described below, the samples shown in Table 1 were subjected to an antifungal effect against M. furfur.

[0057] Antifungal activity: The test organism used in the assay is Malassezia furfur 14521. M. furfur was revived from a glycerol stock in a YPD agar plate (yeast extract peptone dextrose medium) containing 1% corn oil. The composition of YPD is: yeast extract: 10 g / liter, dextrose 20 g / liter, peptone 20 g / liter, and agarose 0.15%. The plates were incubated at 30 °C for 72 hours to form fungal colonies. Colonies obtained from the plates were used to prepare a suspension culture of M. furfur in YPD broth. Using a spectrophotometer, the optical density of the suspension culture was adjusted to 0.6. This suspension was diluted 1:10 using YPD broth, and 100 μl of this culture was added to each well of a 96-well test plate. For each of the concentrations tested, a 40-fold concentrated stock solution of piroctone olamine was prepared. For example, for a test concentration of 0.001% piroctone olamine, a 0.04% stock was prepared in DMSO (dimethyl sulfoxide). 5 μl of piroctone olamine was added to 100 μl of the M. furfur culture. For each of the concentrations tested, a 4-fold concentrated stock solution of itaconic acid or sodium benzoate was prepared. For example, for a test concentration of 0.001% itaconic acid or sodium benzoate, a 0.004% stock was prepared in YPD broth. 50 μl of itaconic acid or sodium benzoate was added to 100 μl of the M. furfur culture. In wells containing only one test component (either itaconic acid or sodium benzoate only), 50 μl of the test component was added to 100 μl of the fungal culture, and then the volume was made up to 200 μl using YPD broth. In wells containing only piroctone olamine, 5 μl of piroctone olamine was added to 100 μl of the fungal culture, and then the volume was made up to 200 μl using YPD broth. The plates were incubated at 30 °C for 72 hours. After incubation, 10 μl of 1% resazurin was added to each well and incubated at 30 °C for 18 hours. Resazurin (7-hydroxy-3H-phenoxazin-3-one 10-oxide) is a blue dye used as a redox indicator in cell viability assays.In living cells, dehydrogenase enzymes reduce resazurin (blue and non-fluorescent) to form the red fluorescent dye resorufin. Wells containing living cells appear pink, while wells containing dead cells appear blue / purple. The antifungal effect of a component, or combination of components, is calculated based on the color development.

[0058] Evaluation of synergistic effects using the fractional inhibitory concentration (ΣFIC). The ΣFIC method was used to evaluate the combination of test components with a synergistic antifungal effect. The ΣFIC of the combination was calculated using the following formula: ΣFIC of combination A + B + C = [concentration of A] / MIC of A + [concentration of B] / MIC of B + [concentration of C] / MIC of C, where MIC is the minimum inhibitory concentration (MIC) of the component. The MIC of the test component is the lowest concentration of the component required to inhibit the growth of the test organism.

[0059] As shown below, the MICs of the various active substances used were determined: Dimethyl itaconate: 0.5 wt% Sodium benzoate: 0.5 wt% Piroctone olamine: 0.002 wt%

[0060] The ΣFIC values for the various combinations are shown in Table 1 below:

[0061]

Table 1

[0062] The data in Table 1 above show that the combination of itaconic acid, sodium benzoate and very low concentrations of piroctone olamine results in a synergistic antifungal activity.

[0063] [Examples 16 - 25] Antifungal effect of the composition according to the invention using esters of itaconic acid: As described above in this specification, the samples shown in Table 1 were subjected to an antifungal effect against M. furfur.

[0064] The ΣFIC values for various combinations are shown in Table 2 below:

[0065]

Table 2

[0066] The data in Table 2 shows that similar data can be obtained by using dimethyl itaconate instead of itaconic acid.

Claims

1. An antimicrobial composition for preventing dandruff, comprising itaconic acid or its ester; benzoic acid or its salt; and piroctone olamine, wherein the concentration of piroctone olamine is 0.0001 to 1% by weight of the composition, and the weight ratio of piroctone olamine to itaconic acid or its ester is in the range of 1:10 to 1:250, and the weight ratio of piroctone olamine to benzoic acid or its salt is in the range of 1:10 to 1:

250.

2. The composition according to claim 1, wherein the ester of itaconic acid is dimethyl itaconate.

3. The composition according to claim 1 or 2, wherein the salt of benzoic acid is sodium benzoate.

4. The composition according to any one of claims 1 to 3, wherein the concentration of itaconic acid or its ester is in the range of 0.01 to 2% by weight of the composition.

5. The composition according to any one of claims 1 to 4, wherein the concentration of benzoic acid or its salt is in the range of 0.01 to 2% by weight of the composition.

6. The composition according to any one of claims 1 to 5, which is a shampoo or a hair conditioner.

7. The composition according to any one of claims 1 to 6, further comprising a cosmetically acceptable carrier selected from an anionic surfactant, a cationic surfactant, an amphoteric surfactant or a zwitterionic surfactant.

8. A method for inhibiting the growth of M. furfur, comprising applying the composition according to any one of claims 1 to 7 to a desired skin surface.

9. Use of the composition according to any one of claims 1 to 7 for preventing dandruff.

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