WO2013050241A1

WO2013050241A1 - Anti-dandruff composition comprising an azole active

Info

Publication number: WO2013050241A1
Application number: PCT/EP2012/068350
Authority: WO
Inventors: Arash Mohajer MOGHADAM
Original assignee: Unilever N.V.; Unilever Plc; Hindustan Unilever Limited; Conopco, Inc., D/B/A Unilever
Priority date: 2011-10-03
Filing date: 2012-09-18
Publication date: 2013-04-11
Also published as: AR088099A1

Abstract

Anti-dandruff composition comprising an azole anti-dandruff active and a copolymer comprising acrylamidopropyltrimonium chloride.

Description

ANTI -DANDRUFF COMPOSITION COMPRISING AN AZOLE ACTIVE

The present invention relates to an improved antidandruff composition comprising an azole antidandruff active.

Despite the prior art there remains a need for improved antidandruff compositions.

Accordingly, the present invention provides an anti-dandruff composition comprising an azole antidandruff active and a copolymer comprising

acrylamidopropyltrimonium chloride. Preferably, the copolymer also comprises acrylamide. More preferably the copolymer has the INCI Name: Acrylamidopropyl Trimonium Chloride/Acrylamide Copolymer. A suitable copolymer is commercially available from Ashland as N-Hance SP-100®. Acrylamidopropyltrimonium chloride / acrylamide copolymer has been described for use in delivering actives such as silicone, emollients and antimicrobial agents such as zinc and selenium onto hair and skin by forming coacervates with anionic surfactants. However, we have surprisingly found that it can improve the delivery of azole antidandruff actives which do not associate with the coacervates between the copolymer and anionic surfactants.

The present invention also provides a method for controlling dandruff comprising the step of topically applying the composition of the present invention to at least a portion of the scalp and/or hair of an individual. The present invention still provides a use of a composition comprising an azole anti-dandruff active and a copolymer comprising acrylamidopropyltrimonium chloride, for preparation of a medicament for controlling dandruff. Preferably, the azole antidandruff active is present at from 0.01 to 5% wt. of the composition, more preferably from 0.1 to 1 .0% wt. and most preferably at from 0.4 to 0.7% wt. of the composition. Preferably, the copolymer is present at from 0.01 to 2% wt. of the composition, more preferably from 0.05 to 1 .0% wt. and most preferably at from 0.04 to 0.5% wt. of the composition.

Preferably, the weight ratio of the amount of the copolymer to the amount of the azole antidandruff active is in the range of from 1 :50 to 2:1 , more preferably from 1 :20 to 1 :2, even more preferably from 1 :10 to 1 :3.

Preferably, the azole antidandruff active is selected from imidazole, triazole, and thiazole antifungals.

Azole antidandruff actives inhibit the enzyme lanosterol 14 a-demethylase; the enzyme necessary to convert lanosterol to ergosterol. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.

Imidazoles include miconazole, ketoconazole, climbazole, clotrimazole, econazole, omoconazole, bifonazole, butoconazole, fenticonazole, isoconazole, oxiconazole, sertaconazole, sulconazole, tioconazole. Triazoles include fluconazole, itraconazole, isavuconazole, ravuconazole, posaconazole, voriconazole, terconazole, albaconazole.

Thiazoles include abafungin. The most preferred azole antidandruff active is climbazole. Preferably, the composition also comprises a cationic deposition polymer.

Preferably, the cationic deposition polymer is guar or cassia derived

polygalactomannan modified with hydroxypropyl trimonium chloride.

It is highly preferred that compositions according to the invention should contain from 0.04% to 2% wt. of the composition cationic deposition polymer, more preferably from 0.05 to 0.5% wt. and most preferably from 0.08 to 0.25% by weight of the composition.

Additionally or alternatively the weight ratio of the amount of the cationic deposition polymer to the amount of the copolymer is preferably in the range from 10:1 to 1 :10, more preferably from 5:1 to 1 :5, most preferably 2:1 to 1 :2.

The composition according to the invention may be in any common product form used to treat hair. However, preferably, it is shampoo composition.

The composition according to the invention may comprise any of the ingredients commonly found in hair treatment compositions depending on the product form.

For example, where the composition is a shampoo it will comprise at least one cleansing surfactant such as is commonly employed in shampoos. Where it is a composition which aims to provide conditioning benefit, whether as part of a shampoo composition or a dedicated conditioning composition it will comprise a conditioning active. Suitable conditioning actives include fatty alcohols, silicones and cationic surfactants.

Examples of suitable anionic cleansing surfactants are the alkyi sulphates, alkyi ether sulphates, alkaryl sulphonates, alkanoyi isethionates, alkyi succinates, alkyi sulphosuccinates, alkyi ether sulphosuccinates, N-alkyl sarcosinates, alkyi phosphates, alkyi ether phosphates, and alkyi ether carboxylic acids and salts thereof, especially their sodium, magnesium, ammonium and mono-, di- and triethanolamine salts. The alkyi and acyl groups generally contain from 8 to 18, preferably from 10 to 16 carbon atoms and may be unsaturated. The alkyi ether sulphates, alkyi ether sulphosuccinates, alkyi ether phosphates and alkyi ether carboxylic acids and salts thereof may contain from 1 to 20 ethylene oxide or propylene oxide units per molecule.

Typical anionic cleansing surfactants for use in compositions of the invention include sodium oleyl succinate, ammonium lauryl sulphosuccinate, sodium lauryl sulphate, sodium lauryl ether sulphate, sodium lauryl ether sulphosuccinate, ammonium lauryl sulphate, ammonium lauryl ether sulphate, sodium

dodecylbenzene sulphonate, triethanolamine dodecylbenzene sulphonate, sodium cocoyl isethionate, sodium lauryl isethionate, lauryl ether carboxylic acid and sodium N-lauryl sarcosinate.

Preferred anionic surfactants are the alkyi sulfates and alkyi ether sulfates. These materials have the respective formulae R2OSO3M and R1O (C2H O) _XSO3M, wherein R₂ is alkyi or alkenyl of from 8 to 18 carbon atoms, x is an integer having a value of from about 1 to about 10, and M is a cation such as ammonium, alkanolamines, such as triethanolamine, monovalent metals, such as sodium and potassium, and polyvalent metal cations, such as magnesium, and calcium. Most preferably R2 has 12 to 14 carbon atoms, in a linear rather than branched chain.

Preferred anionic cleansing surfactants are selected from sodium lauryl sulphate and sodium lauryl ether sulphate(n)EO, (where n is from 1 to 3); more preferably sodium lauryl ether sulphate(n)EO, (where n is from 1 to 3); most preferably sodium lauryl ether sulphate(n)EO where n=1 . Preferably the level of alkyl ether sulphate is from 0.5 wt% to 25 wt% of the total composition, more preferably from 3 wt% to 18 wt%, most preferably from 6 wt% to 15 wt% of the total composition. The total amount of anionic cleansing surfactant in compositions of the invention generally ranges from 0.5 wt% to 45 wt%, more preferably from 1 .5 wt% to 20 wt%.

Compositions of the invention may contain non-ionic surfactant. Most preferably non-ionic surfactants are present in the range 0 to 5wt%.

Nonionic surfactants that can be included in compositions of the invention include condensation products of aliphatic (Cs - Cis) primary or secondary linear or branched chain alcohols or phenols with alkylene oxides, usually ethylene oxide and generally having from 6 to 30 ethylene oxide groups. Alkyl ethoxylates are particularly preferred. Most preferred are alkyl ethoxylates having the formula R- (OCH₂CH₂)_nOH, where R is an alkyl chain of C12 to C15, and n is 5 to 9.

Other suitable nonionic surfactants include mono- or di-alkyl

alkanolamides. Examples include coco mono- or di-ethanolamide and coco mono-isopropanolamide.

Further nonionic surfactants which can be included in shampoo compositions of the invention are the alkyl polyglycosides (APGs). Typically, APG is one which comprises an alkyl group connected (optionally via a bridging group) to a block of one or more glycosyl groups. Preferred APGs are defined by the following formula:

RO - (G)n wherein R is a branched or straight chain alkyl group which may be saturated or unsaturated and G is a saccharide group.

R may represent a mean alkyl chain length of from about C₅ to about

C20- Preferably R represents a mean alkyl chain length of from about Cs to about Ci2. Most preferably the value of R lies between about 9.5 and about 10.5. G may be selected from C₅ or Ce monosaccharide residues, and is preferably a glucoside. G may be selected from the group comprising glucose, xylose, lactose, fructose, mannose and derivatives thereof. Preferably G is glucose.

The degree of polymerisation, n, may have a value of from about 1 to about 10 or more. Preferably, the value of n lies from about 1 .1 to about 2. Most preferably the value of n lies from about 1 .3 to about 1 .5. Suitable alkyl polyglycosides for use in the invention are commercially available and include for example those materials identified as: Oramix NS10 ex Seppic; Plantaren 1200 and Plantaren 2000 ex Henkel.

Other sugar-derived nonionic surfactants which can be included in compositions of the invention include the C10-C18 N-alkyl (Ci-Ce) polyhydroxy fatty acid amides, such as the C12-C18 N-methyl glucamides, as described for example in

WO 92 06154 and US 5 194 639, and the N-alkoxy polyhydroxy fatty acid amides, such as C10-C18 N-(3-methoxypropyl) glucamide. Amphoteric or zwitterionic surfactant can be included in an amount ranging from 0.5 wt% to about 8 wt%, preferably from 1 wt% to 4 wt% of the total shampoo composition.

Examples of amphoteric or zwitterionic surfactants include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulphobetaines (sultaines), alkyl glycinates, alkyi carboxyglycinates, alkyi amphoacetates, alkyi amphopropionates, alkylamphoglycinates, alkyi amidopropyl hydroxysultaines, acyl taurates and acyl glutamates, wherein the alkyi and acyl groups have from 8 to 19 carbon

atoms. Typical amphoteric and zwitterionic surfactants for use in shampoos of the invention include lauryl amine oxide, cocodimethyl sulphopropyl betaine, lauryl betaine, cocamidopropyl betaine and sodium cocoamphoacetate.

A particularly preferred amphoteric or zwitterionic surfactant is cocamidopropyl betaine.

Mixtures of any of the foregoing amphoteric or zwitterionic surfactants may also be suitable. Preferred mixtures are those of cocamidopropyl betaine with further amphoteric or zwitterionic surfactants as described above. A preferred further amphoteric or zwitterionic surfactant is sodium cocoamphoacetate.

The invention will now be described with reference to the following non-limiting examples.

EXAMPLE 1

The following formulation is an embodiment of the invention and is made by standard processes.

Ingredient % wt.

Sodium Laureth Sulphate 14

Cocoamidopropyl betaine 1 .6 acrylamidopropyltrimonium chloride / acrylamide copolymer^* 0.1

Zinc Pyrithione 1 .0

Climbazole 0.5

Zinc sulphate 0.1 Dimethicone 2.0

Perfume 0.7

Sodium chloride 0.5

Propylene Glocol 1 .0

Acrylic Acid polymer (Carbomer) 0.6

Polypropylene Glycol 0.1

Preservative 0.22

Preservative 0.09

Water To 100

^* N-Hance SP-100 ex. Ashland. EXAMPLE 2

The control shampoo is a shampoo with 1 % Zinc Pyrithione and 0.5% Climbazole (16/1 .6% SLES/CAPB surfactant base with 0.2% cationic modified

polygalactomannan extracted from guar). The SP100 shampoo is the standard shampoo + 0.1 % SP100.

Measurement of Climbazole Deposition

Climbazole deposition in vitro was determined by ethanol extraction of the compound from an artificial skin model (Vitro-Skin™; representative of scalp skin), followed by HPLC measurement. Quantitation was made by reference to a standard curve.

Pre-cut artificial skin was sandwiched in a plastic ring support, with its rough topography facing up. Water (1 .5ml) was added to the plastic ring, followed by 0.5ml of testing composition. The mixture was then stirred with a teflon stirring rod, ensuring contact with the artificial skin surface, so as to mimic the massaging of the scalp by a consumer during hair washing. The solutions were removed from the plastic ring with a dropper, ensuring that no liquor remained, and the artificial skin rinsed with 2ml of distilled water, including 30s of stirring as before. The rinsing water was then removed. Climbazole extraction was performed with ethanol (100%, 3ml) with 60s stirring. The resulting supernatant was filtered through a 0.45μηη PTFE filter into a standard HPLC vial. HPLC detection of climbazole was performed by Agilent 1 100. Climbazole concentration (ppm) was measured from the generated standard calibration curves.

Assessment of Bio-efficacy (Malassezia Inhibition)

The bio-efficacy was assessed using an in vitro substantivity assay which evaluates the effectiveness of actives in shampoo and conditioners using

Malassezia furfur CBS 1878 as the organism.

Malassezia furfurfor the inoculation of artificial skin were initially grown in

Pityrosporum Broth, and added to 0.85 wt.% of sodium chloride immediately prior to the inoculation of the Vitro-Skin™ at a final concentration of 2-6x10⁵ cells / ml. Vitro-Skin™ was sandwiched in a plastic ring support, with its rough topography facing up. 0.2 g of testing sample (or water) was added to the plastic ring, followed by 1 .8 ml of water. The mixture was then stirred with a teflon stirring rod, ensuring contact with the artificial skin surface. The solutions were removed from the plastic ring with a dropper, ensuring that no liquor remained, and the artificial skin rinsed with 4ml of distilled water, including 30s of stirring as before. The rinsing water was then removed. The water rinsing step was repeated once. The plastic ring and Vitro-Skin were dried naturally. Vitro-Skin™ was placed onto a Modified Dixon Agar Plate (1 skin per plate), and 0.2ml of inoculum was gently pipetted onto the rough surface of the skin, in a film 1 -2 mm deep. After the agar had gelled, the plates were placed in an incubator (32°C) for 24h. Following incubation, each piece of Vitro-Skin™ was carefully folded in half (inoculum on the inside) using sterile forceps, and placed a vial containing 10 ml of Butterfield' s phosphate buffer (pH 7.2), 0.1 % Triton X-100, 0.5% Tween and 0.08% lecithin. The vial was vortexed for 1 min (high setting) and then treated ultrasonically for 1 min. For 24h incubated samples, 20 μΙ of 10° - 10^"3 dilutions were plated onto Modified Dixon Agar Plates, and incubated at 32 °C for 3-4 days. The number of colonies on each plate were then counted, and final numbers determined by multiplying by the appropriate dilution. The microkill inhabitation data were calculated by the equation: Log reduction = LogioCFU(testing sample) - LogioCFU(water), wherein CFU refers to colony-forming units.

Deposition data

The data shows that SP-100 can significantly improve the deposition of climbazole and also the anti-fungal efficacy of the composition against Malassezia spp. the postulated dandruff causing micro-organism.

Claims

1 . Anti-dandruff composition comprising an azole anti-dandruff active and a copolymer comprising acrylamidopropyltrimonium chloride.

2. Composition according to claim 1 wherein the copolymer comprises

acrylamide.

Composition according to claim 1 or 2 wherein the azole is selected from imidazoles, thiazoles and triazoles.

Composition according to any preceding claim wherein the azole is selected from miconazole, ketoconazole, climbazole, clotrimazole, econazole, omoconazole, bifonazole, butoconazole, fenticonazole, isoconazole, oxiconazole, sertaconazole, sulconazole, tioconazole, fluconazole, itraconazole, isavuconazole, ravuconazole, posaconazole, voriconazole, terconazole, albaconazole and abafungin.

Composition according to any preceding claim wherein the copolymer is present at from 0.01 to 2% wt. of the composition.

Composition according to any preceding claim wherein the azole is present at from 0.01 to 5% wt. of the composition.

Composition according to any preceding claim wherein the weight ratio of the amount of the copolymer to the amount of the azole antidandruff active is in the range of from 1 :20 to 1 :2.

8. Composition according to any preceding claim comprising a cleansing

surfactant. A method for controlling dandruff comprising the step of topically applying the composition of any preceding claim to at least a portion of the scalp and/or hair of an individual.

Use of a copolymer comprising acrylamidopropyltrimonium chloride for improving the deposition of an azole anti-dandruff active.