Personal care compositions comprising a piroctone complex

Abstract

The present invention relates to a personal care composition comprising a surfactant-insoluble piroctone complex and a surfactant.

Description

Technical Field

[0001] The present invention relates to personal care compositions, particularly hair care compositions, comprising a piroctone complex. Background Art

[0002] Dandruff is a problem that affects many people worldwide. This condition manifests itself as clumps of dead skin cells that slough off from the scalp. These clumps of cells are white and have an unsightly appearance. The cause of dandruff is certain members of the Malassezia yeast genus. To combat this problem, hair treatment compositions have been developed over the years that include various active ingredients with anti-dandruff properties. Piroctone compounds, such as piroctone olamine, are one such active ingredient.

[0003] A common problem with piroctone compounds is the poor deposition of the active substance onto the desired surface during washing. The desired surface is typically the scalp and / or hair. For example, piroctone compounds such as piroctone olamine are generally soluble in the surfactants of the cleansing phase included in hair treatment compositions. During excessive rinsing, a large portion of the piroctone may be washed away along with the surfactant. Poor deposition is associated with low anti-dandruff activity, thus providing little relief for the adverse effects of dandruff. To date, attempts have been made to remedy this shortcoming by increasing the piroctone olamine content in hair treatment compositions. This approach raises various issues, such as increased cost, potential instability of the formulation, and potential adverse effects on hair sensory perception. Therefore, it is not an industrially advantageous approach.

[0004] There is still a need to improve the deposition of piroctone compounds, especially piroctone acid or piroctone olamine, on the scalp and / or hair surface during washing. There is also a need to improve the UV stability of compositions containing anti-dandruff agents based on piroctone or piroctone olamine.

[0005] The present invention relates to personal care compositions, in particular hair treatment compositions having good UV stability and deposition of octopirox compounds. Summary of the Invention

[0006] According to the present invention, there is provided a personal care composition comprising a surfactant and a metal piroctone complex having a solubility of 2 wt % or less in a 5 wt % SLES 1EO surfactant aqueous solution at 20°C.

[0007] The present invention also relates to the use of surfactant-insoluble piroctone complexes in hair treatment compositions for protecting piroctone compounds from UV degradation.

[0008] Another aspect of the present invention relates to a non-therapeutic method for treating the hair or scalp comprising applying a personal care composition as described above. DETAILED DESCRIPTION

[0009] Except in the examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material or reaction conditions, physical properties of materials and / or usage may optionally be understood as modified by the word "about".

[0010] All amounts are by weight of the composition unless otherwise indicated.

[0011] It should be noted that in specifying any range of values, any higher value can be associated with any particular lower value.

[0012] Where a feature is disclosed with respect to a particular aspect of the invention (eg, the composition of the invention), such disclosure is also considered applicable, mutatis mutandis, to any other aspect of the invention (eg, the method of the invention).

[0013] Any natural or naturally derived ingredients mentioned in this application are of European origin.

[0014] The composition of the present invention comprises a personal care composition comprising a surfactant-insoluble piroctone complex and a surfactant. In the context of this application, a surfactant-insoluble piroctone complex is a complex having a solubility of 2 wt% or less in a 5 wt% aqueous solution of SLES1EO surfactant at 20°C.

[0015] Piroctone complex

[0016] The surfactant-insoluble piroctone complex is preferably an insoluble metal piroctone complex, more preferably a manganese piroctone complex or a copper piroctone complex, particularly copper dipyrone and / or manganese dipyrone and / or manganese tripyrone. Particularly interesting is copper dipyrone and / or manganese tripyrone, wherein copper dipyrone is the most preferred.

[0017] Preferably, the surfactant-insoluble piroctone complex is prepared by reacting octopirox (piroctone olamine) with a metal salt, more preferably by the following steps:

[0018] Octiprazone (piroctone olamine) is dissolved in a suitable solvent, the metal salt is dissolved in a suitable solvent, and the two solutions are combined in such a way that the metal piroctone complex is formed.

[0019] Preferably, the metal salt used to form the insoluble metal piroctone complex is a metal chloride.

[0020] The piroctone complex may be formed prior to its addition to the remainder of the composition or may be formed in situ within the composition.

[0021] Preferably, the piroctone complex is present in an amount of 0.01 to 2 wt% of the total composition, more preferably 0.05 to 1 wt% and most preferably 0.1 to 0.8 wt% of the composition.

[0022] Surfactant system

[0023] The composition may be in the form of any common personal product, in particular for use as a hair care product. Preferably, it is a rinse-off composition, and most preferably, it is an anti-dandruff shampoo composition.

[0024] Depending on the product form, the composition may comprise any ingredients typically found in personal care products, especially hair care products.

[0025] For example, when the composition is a shampoo, it will comprise a surfactant system including at least one cleansing surfactant suitable for use in shampoos. When it is a composition intended to provide conditioning benefits, it will comprise a conditioning active. Suitable conditioning actives include fatty alcohols, silicones and cationic surfactants.

[0026] Examples of suitable anionic cleansing surfactants are alkyl sulfates, alkyl ether sulfates, alkylaryl sulfonates, alkanoyl isethionates, alkyl succinates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, N-alkyl sarcosinates, alkyl phosphates, alkyl ether phosphates and alkyl ether carboxylic acids and their salts, in particular the sodium, magnesium, ammonium and monoethanol, diethanol and triethanolamine salts thereof. The alkyl and acyl groups generally contain 8 to 18, preferably 10 to 16, carbon atoms and may be unsaturated. The alkyl ether sulfates, alkyl ether sulfosuccinates, alkyl ether phosphates and alkyl ether carboxylic acids and their salts may contain 1 to 20 ethylene oxide or propylene oxide units per molecule.

[0027] Typical anionic cleansing surfactants for use in the compositions of the present invention include sodium oleyl succinate, ammonium lauryl sulfosuccinate, sodium lauryl sulfate, sodium lauryl ether sulfate, sodium lauryl ether sulfosuccinate, ammonium lauryl sulfate, ammonium lauryl ether sulfate, sodium dodecylbenzenesulfonate, triethanolamine dodecylbenzenesulfonate, sodium cocoyl isethionate, sodium lauryl isethionate, lauryl ether carboxylic acid, and sodium N-lauryl sarcosinate.

[0028] Preferred anionic surfactants are alkyl sulfates and alkyl ether sulfates. These materials have the respective formulas ROSO3M and RO(C2H4O) xSO3M, wherein R is an alkyl or alkenyl group of 8 to 18 carbon atoms, x is an integer having a value of about 1 to about 10, and M is a cation (e.g., ammonium), an alkanolamine (e.g., triethanolamine), a monovalent metal (e.g., sodium and potassium), and a multivalent metal cation (e.g., magnesium and calcium). Most preferably, R has 12 to 14 carbon atoms in a straight chain rather than a branched chain.

[0029] Preferred anionic cleansing surfactants are selected from sodium lauryl sulfate and sodium lauryl ether sulfate (n)EO, (wherein n is 1 to 3); more preferably sodium lauryl ether sulfate (n)EO, (wherein n is 1 to 3); most preferably sodium lauryl ether sulfate 1EO.

[0030] Preferably, the alkyl ether sulphate is present in an amount of from 0.5 to 25 wt% of the total composition, more preferably from 3 to 18 wt% and most preferably from 6 to 15 wt% of the total composition.

[0031] The total amount of anionic cleansing surfactant in the compositions of the present invention is typically from 0.5% to 45% by weight, more preferably from 1.5% to 20% by weight.

[0032] The composition of the present invention may contain a nonionic surfactant. Most preferably, the nonionic surfactant is present in the range of 0 to 5% by weight.

[0033] Nonionic surfactants that may be included in the compositions of the present invention include aliphatic (C8-C 18 ) condensation products of primary or secondary straight or branched chain alcohols or phenols with an alkylene oxide, typically ethylene oxide, and typically having from 6 to 30 ethylene oxide groups. Alkyl ethoxylates are particularly preferred. Most preferred are those having the formula R-(OCH2CH2) n Alkyl ethoxylates of OH, where R is C 12-15 alkyl chain and n is 5 to 9.

[0034] Other suitable nonionic surfactants include mono- or di-alkyl alkanolamides. Examples include coconut mono- or di-ethanolamide and coconut monoisopropanolamide.

[0035] Other nonionic surfactants that may be included in the shampoo compositions of the present invention are alkyl polyglycosides (APGs). Typically, an APG is one that comprises an alkyl group linked (optionally via a bridging group) to a block of one or more sugar groups. Preferred APGs are defined by the formula:

[0036] RO—(G) n

[0037] 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 an average length of about C5 to about C 20Most preferably, R represents an alkyl chain having an average length of about C 9.5 to about C 10.5 G may be selected from C5 or C6 monosaccharide residues, and is preferably a glucoside. G may be selected from glucose, xylose, lactose, fructose, mannose and derivatives thereof. Preferably, G is glucose.

[0038] The degree of polymerization, n, may have a value of from about 1 to about 10 or more. Preferably, n has a value of from about 1.1 to about 2. Most preferably, n has a value of from about 1.3 to about 1.5.

[0039] Suitable alkyl polyglycosides for use in the present invention are commercially available and include, for example, those materials identified as: Oramix NS10c ex Seppi; Plantaren 1200 and Plantaren 2000 ex BASF (DeWolf).

[0040] Other sugar-derived nonionic surfactants that may be included in the compositions for use in the present invention include C 10 -C 18 N-alkyl (C1-C6) polyhydroxy fatty acid amides such as C 12 -C 18 N-methylglucamides, such as those described in WO 9206154 and US Pat. No. 5,194,639, and N-alkoxy polyhydroxy fatty acid amides (such as C 10 -C 18 N-(3-methoxypropyl)glucamide).

[0041] Amphoteric or zwitterionic surfactants may be present in amounts of 0.5% to about 8%, preferably 1% to 4%, by weight of the total shampoo composition.

[0042] Examples of amphoteric or zwitterionic surfactants include alkylamine oxides, alkyl betaines, alkylamidopropyl betaines, alkyl sulfobetaines (sulfobetaines), alkyl glycinates, alkyl carboxyglycinates, alkyl amphoacetates, alkyl amphopropionates, alkyl amphoglycinates, alkylamidopropyl hydroxysulfobetaines, acyl taurates, and acyl glutamates, wherein the alkyl and acyl groups have from 8 to 19 carbon atoms. Typical amphoteric and zwitterionic surfactants for use in shampoos of the present invention include laurylamine oxide, cocodimethyl sulfopropyl betaine, lauryl betaine, cocamidopropyl betaine, and sodium cocoamphoacetate.

[0043] A particularly preferred amphoteric or zwitterionic surfactant is cocamidopropyl betaine.

[0044] Mixtures of any of the aforementioned amphoteric or zwitterionic surfactants may also be suitable. Preferred mixtures are mixtures of cocamidopropyl betaine with other amphoteric or zwitterionic surfactants as described above. Further preferred amphoteric or zwitterionic surfactant is sodium cocoamphoacetate.

[0045] Particularly preferred compositions comprise a surfactant system comprising: sodium lauryl sulfate or sodium (n)EO lauryl ether sulfate, (wherein n is 1 to 3) at 10 to 20% by weight of the composition; cocamidopropyl betaine at 0.5 to 5% by weight of the composition; and sodium cocoamphoacetate or sodium lauryl cocoamphoacetate at 0.5 to 5% by weight of the composition.

[0046] Other ingredients

[0047] The compositions may also contain one or more of the following optional ingredients:

[0048] pH adjusters

[0049] The pH of the composition is preferably in the range of 5 to 8, more preferably in the range of 6 to 7, for example 6.5. The pH of the composition can be adjusted using alkaline agents (such as sodium hydroxide) or acidic agents (such as citric acid) known in the art.

[0050] Cationic polymers

[0051] Cationic polymers are preferred ingredients in the hair care compositions of the present invention for enhancing the performance of said compositions.

[0052] The cationic polymer may be a homopolymer or formed from two or more types of monomers. The molecular weight of the polymer is typically from 5,000 to 10,000,000, usually at least 10,000, preferably from 100,000 to about 2,000,000. The polymer has cationic nitrogen-containing groups, such as quaternary ammonium or protonated amino groups, or mixtures thereof.

[0053] Cationic nitrogen-containing groups are typically present as substituents on a fraction of the total monomer units of a cationic polymer. Thus, when the polymer is not a homopolymer, it may include intervening non-cationic monomer units. Such polymers are described in the CTFA Cosmetic Ingredient Directory, 3rd Edition. The ratio of cationic to non-cationic monomer units is selected to yield a polymer having a cationic charge density within the desired range.

[0054] Suitable cationic conditioning polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionality with water-soluble spacer monomers such as (meth)acrylamide, alkyl and dialkyl (meth)acrylamides, alkyl (meth)acrylates, vinyl caprolactone, and vinyl pyrrolidine. Alkyl and dialkyl substituted monomers preferably have C1 to C7 alkyl groups, more preferably C1 to C3 alkyl groups. Other suitable spacers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol, and ethylene glycol.

[0055] The cationic amines can be primary, secondary or tertiary amines, depending on the specific species and the pH of the composition. Generally, secondary and tertiary amines are preferred, especially tertiary amines.

[0056] Amine-substituted vinyl monomers and amines can be polymerized in the amine form and subsequently converted to ammonium by quaternization.

[0057] The cationic conditioning polymer may comprise a mixture of monomer units derived from amine-substituted and / or quaternary ammonium-substituted monomers and / or compatible spacer monomers.

[0058] Suitable cationic conditioning polymers include, for example:

[0059] a) Copolymers of 1-vinyl-2-pyrrolidine and 1-vinyl-3-methyl-imidazolium salts (e.g., chloride salts), known in the industry as Polyquaternium-16 by the Cosmetic, Toiletry, and Fragrance Association (CTFA). This material is commercially available from BASF Wyandotte Corp. (Parsippany, NJ, USA) under the LUVIQUAT tradename (e.g., LUVIQUAT FC 370);

[0060] b) a copolymer of 1-vinyl-2-pyrrolidine and dimethylaminoethyl methacrylate, known in the industry (CTFA) as polyquaternium-11. This material is commercially available from Gaf Corporation (Wayne, NJ, USA) under the GAFQUAT trade name (e.g., GAFQUAT 755N);

[0061] c) cationic diallyl quaternary ammonium-containing polymers, including, for example, dimethyldiallylammonium chloride homopolymer and copolymers of acrylamide and dimethyldiallylammonium chloride, known in the industry (CTFA) as Polyquaternium 6 and Polyquaternium 7, respectively;

[0062] d) inorganic acid salts of aminoalkyl esters of homopolymers and copolymers of unsaturated carboxylic acids having 3 to 5 carbon atoms (as described in U.S. Pat. No. 4,009,256);

[0063] e) Cationic polyacrylamides (as described in WO 95 / 22311).

[0064] Preferred cationic conditioning polymers that may be used include cationic polysaccharide polymers such as cationic cellulose derivatives, cationic starch derivatives and cationic guar gum derivatives. Suitably, such cationic polysaccharide polymers have a charge density of from 0.1 to 4 meq / g.

[0065] Cationic polysaccharide polymers suitable for use in the compositions of the present invention include those of the formula:

[0066] AO-[RN + (R 1 )(R 2 )(R 3 )X - ],

[0067] Wherein: A is an anhydroglucose residue, such as an anhydroglucose residue of starch or cellulose. R is an alkylene, oxyalkylene, polyoxyalkylene or hydroxyalkylene group, or a combination thereof. 1 、R 2 and R 3 independently represents an alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl group, each containing up to about 18 carbon atoms. The total number of carbon atoms in each cationic moiety (i.e., R 1 、R 2 and R 3 The total number of carbon atoms in (a) is preferably about 20 or less, and X is an anionic counterion.

[0068] Cationic cellulose is available from Amerchol Corp. (Edison, NJ, USA) as the Polymer JR (trade name) and LR (trade name) series of polymers, which are salts of hydroxyethyl cellulose reacted with trimethylammonium-substituted epoxides, known in the industry (CTFA) as Polyquaternium 10. Another type of cationic cellulose includes polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryldimethylammonium-substituted epoxides, known in the industry (CTFA) as Polyquaternium 24. These materials are available from Amerchol Corp. (Edison, NJ, USA) under the trade name Polymer LM-200.

[0069] Other suitable cationic polysaccharide polymers include quaternary nitrogen-containing cellulose ethers (eg, as described in US Pat. No. 3,962,418), and copolymers of etherified cellulose and starch (eg, as described in US Pat. No. 3,958,581).

[0070] A particularly suitable type of cationic polysaccharide polymer that can be used is a cationic guar gum derivative, such as guar hydroxypropyltrimonium chloride (commercially available from Rhone-Poulenc in their JAGUAR trademark series).

[0071] Examples are JAGUAR C13S, which has a low degree of substitution with cationic groups and a high viscosity, JAGUAR C15, which has a medium degree of substitution and a low viscosity, JAGUAR C17 (high degree of substitution, high viscosity), JAGUAR C16, which is a hydroxypropylated cationic guar gum derivative containing a low level of substitution and cationic quaternary ammonium groups, and JAGUAR 162, which is a high clarity, medium viscosity guar gum with a low degree of substitution.

[0072] Preferably, the cationic conditioning polymer is selected from cationic cellulose and cationic guar gum derivatives. Particularly preferred cationic polymers are JAGUAR C13S, JAGUAR C15, JAGUAR C17, JAGUAR C16 and JAGUAR C162. Particularly preferred is guar hydroxypropyltrimonium chloride.

[0073] Cationic conditioning polymers are typically present in the compositions of the present invention at levels of from 0.01 to 5%, preferably from 0.05 to 1%, more preferably from 0.08 to 0.5% by weight of the composition.

[0074] When cationic conditioning polymers are present in the hair care compositions of the present invention, it is preferred that the copolymers have an average diameter (D 3,2 The presence of emulsion particles of 2 microns or less, as measured by light scattering using a Malvern particle sizer.

[0075] The hair care compositions of the present invention are preferably aqueous, i.e. they have water or an aqueous solution or a lyotropic liquid crystal phase as their major component. Suitably, the composition comprises 50 to 98 wt%, preferably 60 to 90 wt% water, based on the total weight of the composition.

[0076] Siloxane

[0077] The anti-dandruff hair composition may additionally comprise from 0.1 to 10 wt. %, preferably from 0.1 to about 8 wt. %, more preferably from about 0.3 to about 5 wt. % of silicone.

[0078] Preferred suitable silicones may include polyalkyl silicones, polyaryl silicones, polyalkylaryl silicones, polyether silicone copolymers, amino silicones, and mixtures thereof.

[0079] Silicones may be present as free silicone oils or in the form of silicone emulsions.

[0080] Preferably the silicone is present in the form of a silicone emulsion, more preferably an aqueous surfactant-stabilized emulsion of silicone particles having a number average particle size ranging from 10 to 1,000 nm, most preferably from about 100 to about 500 nm.

[0081] Aminosilicones are commonly formulated in hair compositions. Aminosilicones are silicones that contain at least one primary, secondary, tertiary, or quaternary ammonium group. High molecular weight silicone gums can also be used. Another useful type is crosslinked silicone elastomers, such as dimethicone / vinyl / dimethicone crosspolymers (e.g., Dow Corning 9040 and 9041).

[0082] Examples of suitable preformed silicone emulsions include emulsions DC2-1766, DC2-1784, DC-1785, DC-1786, DC-1788 and microemulsions DC2-1865 and DC2-1870, all available from Dow Corning. These are emulsions or microemulsions of dimethiconol. Also suitable are amodimethicone emulsions such as DC939 (from Dow Corning) and SME253 (from GE Silicones).

[0083] Suspension Concentrate

[0084] Preferably, the hair care composition of the present invention also contains a suspending agent. Suitable suspending agents are selected from polyacrylic acid, crosslinked polymers of acrylic acid, copolymers of acrylic acid and hydrophobic monomers, copolymers of carboxylic acid-containing monomers and acrylates, crosslinked copolymers of acrylic acid and acrylates, heteropolysaccharide gums, and crystalline long-chain acyl derivatives. The long-chain acyl derivative is ideally selected from ethylene glycol stearate, alkanolamides of fatty acids having 16 to 22 carbon atoms, and mixtures thereof. Ethylene glycol distearate and polyethylene glycol 3 distearate are preferred long-chain acyl derivatives because they impart pearlescence to the composition. Polyacrylic acid is commercially available as Carbopol 420, Carbopol 488, or Carbopol 493. Polymers of acrylic acid crosslinked with polyfunctional agents can also be used; they are commercially available as Carbopol 910, Carbopol 934, Carbopol 941, and Carbopol 980. An example of a suitable copolymer of a carboxylic acid-containing monomer and an acrylate is Carbopol 1342. All Carbopol (trademark) materials were purchased from Goodrich.

[0085] Suitable cross-linked polymers of acrylic acid and acrylic acid esters are Pemulen TR1 or Pemulen TR2.A suitable heteropolysaccharide gum is xanthan gum, for example available as Kelzan gum.

[0086] Mixtures of any of the above suspending agents may be used. Preferred are mixtures of cross-linked polymers of acrylic acid and crystalline long chain acyl derivatives.

[0087] If included, the suspending agent is typically present in the hair care compositions of the present invention in an amount of from 0.1 to 10 wt%, preferably from 0.5 to 6 wt%, more preferably from 0.9 to 4 wt% based on the total weight of the composition.

[0088] Non-silicone oily conditioning ingredients

[0089] The compositions according to the present invention may also contain a dispersed, non-volatile, water-insoluble oily conditioning agent.

[0090] This component will be dispersed in the composition in the form of droplets which form a separate discontinuous phase from the aqueous continuous phase of the composition. In other words, the oily conditioning agent will be present in the shampoo composition in the form of an oil-in-water emulsion.

[0091] By "insoluble" is meant that the material is insoluble in water (distilled or equivalent) at a concentration of 0.1% (w / w) at 25°C. Suitably, the oily conditioning component has a D[3,2] average droplet size of at least 0.4 microns, preferably at least 0.8 microns, and more preferably at least 1 micron. Additionally, the oily conditioning component preferably has a D[3,2] average droplet size of no greater than 10 μm, more preferably no greater than 8 μm, more preferably no greater than 5 μm, still more preferably no greater than 4 μm, and most preferably no greater than 3.5 μm.

[0092] The oily conditioning agent may suitably be selected from oily or fatty materials and mixtures thereof.

[0093] Oily or fatty materials are preferred conditioning agents in shampoo compositions of the present invention for increasing the shine of the hair and enhancing dry combing and dry hair feel.

[0094] Preferred oily and fatty materials will typically have a viscosity of less than 5 Pa.s, more preferably less than 1 Pa.s, and most preferably less than 0.5 Pa.s, for example 0.1 Pa.s, and as measured at 25 degrees Celsius with a Brookfield viscometer (e.g. Brookfield RV) using spindle 3 running at 100 rpm.

[0095] Oily and fatty materials with relatively high viscosities can be used. For example, materials with viscosities up to 65 Pa.s can be used. The viscosity of these materials (i.e., materials with viscosities of 5 Pa.s or greater) can be measured using a glass capillary viscometer, as further specified in Dow Corning Corporate Test Method CTM004, dated July 20, 1970.

[0096] Suitable oily or fatty materials are selected from hydrocarbon oils, fatty esters and mixtures thereof.

[0097] Hydrocarbon oils include cyclic hydrocarbons, straight-chain aliphatic hydrocarbons (saturated or unsaturated) and branched-chain aliphatic hydrocarbons (saturated or unsaturated). Straight-chain hydrocarbon oils preferably contain about 12 to about 30 carbon atoms. Branched-chain hydrocarbon oils can and usually can contain a higher number of carbon atoms. Polymerized hydrocarbons of olefinic monomers such as C2-C6 olefinic monomers are also suitable. These polymers can be straight or branched polymers. The length of straight-chain polymers is usually relatively short, generally having the total carbon atoms as described above for straight-chain hydrocarbons. Branched polymers can have significantly higher chain lengths. The number-average molecular weight of such materials can vary widely, but is usually at most about 2000, preferably about 200 to about 1000, more preferably about 300 to about 600.

[0098] The specific examples of suitable hydrocarbon oils include paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane and mixtures thereof. The branched isomers of these compounds and the hydrocarbons of higher chain lengths can also be used. Exemplary branched isomers are highly branched saturated or unsaturated alkanes, such as the isomers substituted with permethyl, such as the isomers substituted with permethyl of hexadecane and eicosane, such as 2,2,4,4,6,6,8,8-dimethyl-10-methylundecane and 2,2,4,4,6,6-dimethyl-8-methylnonane, sold by Permethyl Corporation. Another example of hydrocarbon polymers is polybutene, such as the copolymer of isobutylene and butene. The commercially available material of this type is the L-14 polybutene from Amoco Chemical Co. (Chicago, 111., USA).

[0099] Particularly preferred hydrocarbon oils are various grades of mineral oil. Mineral oil is a transparent, oily liquid obtained from petroleum, from which wax has been removed and the more volatile fractions have been removed by distillation. The fraction distilled between 250 degrees Celsius and 300 degrees Celsius is called mineral oil, and it consists of a mixture of hydrocarbons within the C16H34 to C21H14 range. Suitable commercially available materials of this type include Sirius M85 and Sirius M125, both available from Silkolene.

[0100] Suitable fatty esters are characterized by having at least 10 carbon atoms and include esters having a hydrocarbyl chain derived from fatty acids or alcohols, such as monocarboxylic acid esters, polyol esters, and dicarboxylic acid esters and tricarboxylic acid esters. The hydrocarbyl groups of the fatty esters herein may also include or have other compatible functional groups covalently bonded thereto, such as amides and alkoxy moieties (e.g., ethoxy or ether linkages). Monocarboxylic acid esters include esters of alcohols and / or acids of the formula R'COOR, wherein R' and R independently represent an alkyl or alkenyl group, and the sum of the carbon atoms in R' and R is at least 10, preferably at least 20.

[0101] Specific examples include, for example, alkyl and alkenyl esters of fatty acids having aliphatic chains of from about 10 to about 22 carbon atoms, and alkyl and / or alkenyl fatty alcohol carboxylates having aliphatic chains derived from alkyl and / or alkenyl alcohols having from about 10 to about 22 carbon atoms, benzoic acid esters of fatty alcohols having from about 12 to 20 carbon atoms.

[0102] Monocarboxylic acid ester need not contain at least one chain with at least 10 carbon atoms, as long as the sum of aliphatic chain carbon atoms is at least 10.Example comprises isopropyl isostearate, hexyl laurate, isohexyl laurate, isohexyl palmitate, isopropyl palmitate, decyl oleate, isodecyl oleate, hexadecyl stearate, decyl stearate, isopropyl isostearate, dihexyl decyl adipate, lauryl lactate, myristyl lactate, cetyl lactate, oleyl stearate, oleyl oleate, oleyl myristate, lauryl acetate, cetyl propionate and oleyl adipate.Also can use carboxylic acid two-and three-alkyl and alkenyl ester.These comprise for example C4-C8 dicarboxylic ester, as succinic acid, glutaric acid, adipic acid, caproic acid, enanthic acid and sad C7-C22 ester (preferred C1-C9). Examples include diisopropyl adipate, diisohexyl adipate, and diisopropyl sebacate. Other specific examples include isohexadecyl stearoyl stearate and tristearoyl citrate.

[0103] Polyol esters include alkylene glycol esters such as ethylene glycol mono- and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol mono- and di-fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol monooleate, polypropylene glycol monostearate, ethoxylated propylene glycol monostearate, polyglycerol poly-fatty acid esters, ethoxylated glycerol monostearate, 1,3-butylene glycol monostearate, 1,3-butylene glycol distearate, polyoxyethylene polyol fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, and mono-, di-, and triglycerides.

[0104] Particularly preferred fatty esters are mono-, di- and triglycerides, more specifically mono-, di- and triesters of glycerol and long-chain carboxylic acids (e.g., C7 to C22 carboxylic acids). A variety of these types of materials can be obtained from plant and animal fats and oils (e.g., coconut oil, castor oil, safflower oil, sunflower oil, cottonseed oil, corn oil, olive oil, cod liver oil, almond oil, avocado oil, palm oil, sesame oil, peanut oil, lanolin and soybean oil). Synthetic oils include triolein dilaurate and tristearin dilaurate.

[0105] Specific examples of preferred materials include cocoa butter, palm stearin, sunflower oil, soybean oil and coconut oil. Suitably the oily or fatty material is present in an amount of 0.05 to 10 wt%, preferably 0.2 to 5 wt%, more preferably about 0.5 to 3 wt%.

[0106] The compositions of the present invention preferably comprise no more than 3 wt% styling polymers, more preferably less than 1 wt% styling polymers, preferably less than 0.1 wt% styling polymers, and most preferably are free of styling polymers.

[0107] In hair treatment compositions containing a conditioning agent, a cationic polymer is preferably also present.

[0108] adjuvants

[0109] The compositions of the present invention may also contain adjuvants suitable for hair care. Typically, such ingredients are included individually at a level of up to 2% by weight, preferably up to 1% by weight, of the total composition.

[0110] Suitable hair care adjuncts include:

[0111] (i) Natural hair root nutrients, such as amino acids and sugars. Examples of suitable amino acids include arginine, cysteine, glutamine, glutamic acid, isoleucine, leucine, methionine, serine and valine, and / or their precursors and derivatives. Amino acids can be added alone, in mixtures or in the form of peptides (e.g., dipeptides and tripeptides). Amino acids can also be added in the form of protein hydrolysates (e.g., keratin or collagen hydrolysates). Suitable sugars are glucose, dextrose and fructose. These can be added alone or in the form of, for example, fruit extracts. A particularly preferred combination of natural hair root nutrients for inclusion in the compositions of the present invention is isoleucine and glucose. A particularly preferred amino acid nutrient is arginine.

[0112] (ii) Hair fiber benefit agents. Examples include ceramides, which moisturize the fiber and maintain cuticle integrity. Ceramides can be obtained by extraction from natural sources or as synthetic ceramides and pseudoceramides. A preferred ceramide is Ceramide II from Quest. Mixtures of ceramides may also be suitable, such as Ceramides LS from Laboratoires Serobiologiques.

[0113] Minor ingredients

[0114] The composition may also include other ingredients to enhance performance and / or consumer acceptance. Such ingredients include fragrances (encapsulated or free, or both), colorants, dyes and pigments, pearlescent agents or opacifiers, viscosity modifiers, stabilizers, and preservatives. Suitable preservative systems include sodium benzoate and sodium salicylate, with sodium hydroxide and citric acid (HO) used to adjust the pH. Alternative preservative systems containing formaldehyde include MIT and DMDM ​​hydantoin.

[0115] Product form

[0116] The composition is preferably a personal care composition, more preferably a shampoo, conditioner, hair spray, mousse, gel, wax or lotion. Particularly preferred product forms are shampoos, after-wash conditioners (leave-in and rinse-off), and hair treatment products such as hair serums. Rinse-off products are preferred, and shampoos are particularly preferred.

[0117] The composition is preferably formulated for treating the hair and subsequently rinsing.

[0118] Particularly preferred hair care compositions are shampoo compositions. The total amount of surfactant (including any co-surfactant and / or any emulsifier) ​​in the shampoo compositions of the present invention is typically from 5 to 30% by weight, preferably from 10 to 25% by weight, more preferably from 15 to 20% by weight of the composition.

[0119] How to use

[0120] The compositions of the present invention may be used in medical or non-medical products.

[0121] The preferred method of use is application to the hair and scalp, preferably followed by rinsing the product from the hair with water. The product is preferably left on the hair for a period of about 2 minutes to about 10 minutes.

[0122] The present invention will now be further described with reference to the following non-limiting examples. The examples of the present invention are illustrated by numbers and the comparative examples are illustrated by letters.

[0123] Example

[0124] Preparation of Metal-Piroctone Complex

[0125] Example 1 Copper Piroctone

[0126] - Under stirring, 0.03 mol of CuCl2·4H2O dissolved in water was added dropwise.

[0127] - Add demineralized water to the precipitation of sticky solids.

[0128] - The suspension was stirred at room temperature for 2-4 hours.

[0129] The isolated white solid was washed and dried over P2O5 under vacuum at 50°C for 24 hours.

[0130] Example 2 Manganese Piroctone

[0131] -0.04 mol of octopirox is dissolved in ethanol.

[0132] - Under stirring, 0.03 mol of MnCl2·4H2O dissolved in water was added dropwise thereto.

[0133] - Add demineralized water to the precipitation of sticky solids.

[0134] - The suspension was stirred at room temperature for 2-4 hours.

[0135] The isolated white solid was washed and dried over P2O5 under vacuum at 50°C for 24 hours.

[0136] Example A Zinc Piroctone

[0137] -0.04 mol of octopirox is dissolved in ethanol.

[0138] - 0.03 mol of ZnCl2 dissolved in water was added dropwise thereto while stirring.

[0139] - Add demineralized water to the precipitation of sticky solids.

[0140] - The suspension was stirred at room temperature for 2-4 hours.

[0141] The isolated white solid was washed and dried over P2O5 under vacuum at 50°C for 24 hours.

[0142] Example 5 Copper Piroctone Prepared During Shampoo Formulation

[0143] - Prepare an aqueous mixture of sodium laureth sulfate 1EO, cocamidopropyl betaine and guar hydroxypropyltrimonium chloride.

[0144] -Sodium salicylate dissolved in water is added to the mixture followed by phenoxyethanol.

[0145] - The pH was adjusted to pH 6 using citric acid (50 wt %).

[0146] - Use sodium chloride to adjust viscosity.

[0147] - Slowly add octopirox to the formulation, followed by an aqueous solution of copper chloride.

[0148] -Add water.

[0149] Solubility of metal piroctone complexes

[0150] The solubility of the metallopiroctone complexes in a 5 wt% aqueous solution of SLES 1EO (sodium lauryl ether sulfate) at 20° C. is listed in Table 1:

[0151] Table 1

[0152] sample % Solubility 1% OCT 100.2 1%Cu-PIR 1.3 1% Mn-PIR 1.0 1% Zn-PIR 111.8

[0153] Shampoo composition

[0154] The following shampoo compositions were prepared.

[0155] Table 2

[0156]

[0157] Solubility of Metallopiroctone Complexes in Shampoo

[0158] - Solubility, as determined visually.

[0159] Table 3

[0160] Example Preparations 3 4 5 B C Appearance opaque opaque opaque transparent transparent

[0161] In vitro deposition experiment on hair matrix

[0162] HPLC-UV method

[0163] Agilent 1100 HPLC system

[0164] ·Agilent Eclipse plus C18 100x4.6; 3.5um column

[0165] Column temperature 30°C, 1.5 ml / min, 302 nm 10 nm ref = 360 / 50 nm, pressure ~75 bar, isocratic mobile phase: acetonitrile / MeOH / water (KH2PO4 20 mM; EDTA (0.5 mM)) (65:13:22), adjusted to pH 4 with phosphoric acid.

[0166] Hair cluster washing program:

[0167] All hair switches were pre-treated by washing with a 14 wt% SLES solution to standardize them. The hair switches were then treated using a washing process under standard conditions using the relevant shampoo base containing octopirox or a metal-piroctone complex. For each composition, the regimen was applied to 3 hair switches.

[0168] Once dry, the hair switches are each treated with ethanol to extract the octopirox or complex.

[0169] The extracts were analyzed by HPLC-UV and the concentration of piroctone was calculated.

[0170] Piroctone complex deposition results

[0171] Table 4

[0172] Example Preparations 3(Cu) B(Zn) C(OCT) Piroctone concentration, ug / mL 41.38 1.44 2.74 Standard deviation of piroctone concentration, ug / mL 5.23 0.03 0.42

[0173] The results demonstrate that the Examples of the present invention have enhanced deposition of piroctone on hair.

[0174] Examples 5, 6 and D

[0175] The UV stability of ethanolic solutions (0.5 mM) of copper and manganese piroctone was measured and compared to a 1 mM solution of octopirox.

[0176] After 5 hours of UV irradiation (UVA 180 uW / cm2, UVB 210 uW / cm2), it was found that manganese piroctone degraded by 3.2%, copper piroctone degraded by 1.8%, and oxymetholone (piroctone) degraded by 46%.

[0177] These results demonstrate the improved UV stability of the metallopiroctone complexes.

Claims

1. A personal care composition comprising a sodium lauryl ether sulfate (1EO) surfactant and 0.1 to 0.8 wt % of an insoluble manganese and / or copper piroctone complex having a solubility of 2 wt % or less in a 5 wt % aqueous solution of the sodium lauryl ether sulfate (1EO) surfactant at 20°C.

2. The personal care composition according to claim 1, wherein the insoluble manganese and / or copper piroctone complex is copper dipyrone and / or manganese dipyrone.

3. The personal care composition according to claim 1 or 2, further comprising an amphoteric surfactant.

4. The personal care composition of claim 1 or 2, further comprising a cationic polymer.

5. The personal care composition of claim 4, wherein the cationic polymer is a cationic guar gum derivative.

6. The personal care composition of claim 1 or 2, further comprising a silicone.

7. The personal care composition according to claim 1 or 2, which is a shampoo.

8. A non-therapeutic method of treating the hair or scalp comprising applying to the hair or scalp a personal care composition according to any one of claims 1 to 7.

9. The non-therapeutic method of claim 8, wherein the composition is washed off after use.

10. Use of 0.1 to 0.8 wt% of an insoluble manganese and / or copper piroctone complex in a hair treatment composition comprising sodium lauryl ether sulfate (1EO) surfactant for protecting a piroctone compound from UV degradation, wherein the insoluble manganese and / or copper piroctone complex has a solubility of 2 wt% or less in a 5 wt% aqueous solution of sodium lauryl ether sulfate (1EO) surfactant at 20°C.

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