Personal care compositions containing metal piroctone complexes

Abstract

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, containing piroctone complexes. [Background technology]

[0002] Dandruff is a problem affecting many worldwide. The condition manifests itself when clumps of dead skin cells slough off the scalp. These are white and result in an aesthetically unpleasing appearance. The contributing factors to dandruff are certain members of the Malassezia yeast. To combat these, hair treatment compositions containing various actives for anti-dandruff effects have been developed. Piroctone compounds, such as piroctone olamine, are one such active.

[0003] A common problem with piroctone compounds is minimal deposition of the active on the desired surface during the cleansing process. These surfaces are typically the scalp and / or hair. For example, piroctone compounds, such as piroctone olamine, are typically soluble in the cleansing phase surfactants found in hair treatment compositions. During excessive rinsing, most of the piroctone is easily washed away along with the surfactant. Poor deposition correlates with poor anti-dandruff activity and therefore provides little relief from the adverse effects of dandruff. To date, attempts to offset this drawback by increasing the amount of piroctone olamine in hair treatment compositions have resulted in various issues, including increased cost, potential formulation instability, and potentially adverse effects on hair feel. Therefore, it is not a preferred approach in the industry.

[0004] There remains a need to improve the deposition of piroctone compounds, particularly piroctonic acid or piroctone olamine, onto the scalp and / or hair surface during the cleansing process. There also remains a need to improve the UV stability of piroctone-containing compositions of piroctone olamine-based antidandruff agents.

[0005] The present invention relates to personal care compositions, particularly 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, wherein the metal piroctone complex has a solubility of 2 wt % or less in a 5 wt % aqueous solution of SLES1EO surfactant at 20°C.

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

[0008] A further aspect of the present invention relates to non-therapeutic methods for treating hair or scalp, including the personal care applications described above. DETAILED DESCRIPTION OF THE INVENTION

[0009] Except in the examples, or where otherwise expressly indicated, all numbers herein indicating quantities of ingredients or reaction conditions, physical properties of ingredients, and / or uses may be understood to be modified by the word "about."

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

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

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

[0013] Any ingredient mentioned in this application that is natural or naturally derived is sourced from Europe.

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

[0015] Piroctone Complex The detergent-insoluble piroctone complex is preferably an insoluble metal piroctone complex, more preferably a manganese piroctone complex or a copper piroctone complex, in particular a copper bispiroctone and / or manganese bispiroctone and / or manganese trispiroctone. Of particular interest are copper bispiroctone and / or manganese trispiroctone, with copper bispiroctone being most preferred.

[0016] Preferably, the detergent-insoluble piroctone complex is prepared by the reaction of octopirox (piroctone olamine) with a metal salt, more preferably by the following steps:

[0017] Dissolving octopirox (piroctone olamine) in a suitable solvent and dissolving a metal salt in a suitable solvent and then combining the two solutions is such that a metal piroctone complex is formed.

[0018] Preferably, the metal salt used to form the insoluble metal piroctone complex is a metal chloride.

[0019] The piroctone complex may be formed prior to addition to the remainder of the composition or in situ within the composition.

[0020] Preferably, the piroctone complex is present at 0.01 to 2% by weight of the total composition, more preferably 0.05 to 1% by weight of the composition, most preferably 0.1 to 0.8% by weight.

[0021] surfactant system The composition may be in any common personal product form used, particularly as a hair care product, preferably a rinse-off composition, most preferably an anti-dandruff shampoo composition.

[0022] The composition may include any of the ingredients commonly found in personal care products, particularly hair care products depending on the product form.

[0023] For example, when composition is shampoo, composition comprises surfactant system, which comprises at least one cleansing surfactant suitable for use in shampoo.When composition is intended to provide conditioning benefits, it comprises conditioning active material.Suitable conditioning active material includes fatty alcohol, silicone and cationic surfactant.

[0024] Examples of suitable anionic detersive surfactants include alkyl sulfates, alkyl ether sulfates, alkaryl 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, particularly their sodium, magnesium, ammonium, and mono-, di-, and triethanolamine salts. 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.

[0025] 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.

[0026] Preferred anionic surfactants are the alkyl sulfates and alkyl ether sulfates. These materials have the formula ROSO3M and RO(C2H4O), respectively. x The cations have the formula SO3M, where R is alkyl or alkenyl of 8 to 18 carbon atoms, x is an integer having a value of 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, R has 12 to 14 carbon atoms in a straight, rather than branched, chain.

[0027] Preferred anionic cleansing surfactants are selected from sodium lauryl sulfate and sodium lauryl ether sulfate (n)EO (n is 1 to 3), more preferably sodium lauryl ether sulfate (n)EO (n is 1 to 3), most preferably sodium lauryl ether sulfate 1EO.

[0028] Preferably, the amount of alkyl ether sulfate is from 0.5% to 25% by weight of the total composition, more preferably from 3% to 18% by weight of the total composition, most preferably from 6% to 15% by weight.

[0029] The total amount of anionic cleansing surfactant in the composition of the present invention will generally range from 0.5% to 45% by weight, more preferably from 1.5% to 20% by weight.

[0030] The compositions of the present invention may contain a non-ionic surfactant, most preferably present in the range of 0 to 5% by weight.

[0031] Nonionic surfactants that can 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 alkylene oxides, usually ethylene oxide, generally having 6 to 30 ethylene oxide groups. Alkyl ethoxylates are particularly preferred. Most preferred are alkyl ethoxylates of the formula R-(OCH2CH2) n OH, where R is C 12-15 It is an alkyl chain, and n is 5 to 9.

[0032] Other suitable nonionic surfactants include mono- or di-alkyl alkanolamides. Examples include coco mono- or di-ethanolamide and coco mono-isopropanolamide.

[0033] Further nonionic surfactants that may be included in the shampoo compositions of the present invention are the alkyl polyglycosides (APGs). Typically, APGs comprise an alkyl group attached (possibly via a bridging group) to a block of one or more glycosyl groups. Preferred APGs are defined by the formula: RO-(G) n In the formula, R is a branched or straight chain alkyl group which may be saturated or unsaturated, and G is a sugar group. R is a C5 to C 20 Most preferably, R represents an alkyl chain having an average length of about C 9.5 ~About C 10.5 G represents an alkyl chain having an average length of 0.05 to 0.05. G may be selected from C5 or C6 monosaccharide residues, preferably a glucoside. G may be selected from the group consisting of glucose, xylose, lactose, fructose, mannose, and derivatives thereof. Preferably, G is glucose.

[0034] The degree of polymerization n may have a value of about 1 to about 10 or more. Preferably, the value of n is about 1.1 to about 2. Most preferably, the value of n is about 1.3 to about 1.5.

[0035] Alkyl polyglycosides suitable for use in the present invention are commercially available and include, for example, materials identified as Oramix NS10 from Seppic, Plantaren 1200 and Plantaren 2000 from BASF (DeWolf).

[0036] Other sugar-derived nonionic surfactants that can be included in the compositions of the present invention include C 10 -C 18 N-alkyl (C1-C6) polyhydroxy fatty acid amides, such as those described in WO 9206154 and U.S. Pat. No. 5,194,639 12 -C 18 N-methyl glucamide, as well as N-alkoxy polyhydroxy fatty acid amides such as C10-C18 N-(3-methoxypropyl) glucamide.

[0037] The amphoteric or zwitterionic surfactant may be present in an amount ranging from 0.5% to about 8%, preferably from 1% to 4% by weight of the total shampoo composition.

[0038] Examples of amphoteric or zwitterionic surfactants include alkylamine oxides, alkylbetaines, alkylamidopropylbetaines, alkylsulfobetaines (sultaines), alkylglycinates, alkylcarboxyglycinates, alkylamphoacetates, alkylamphopropionates, alkylamphoglycinates, alkylamidopropylhydroxysultaines, acyltaurates, and acylglutamates, wherein the alkyl and acyl groups have from 8 to 19 carbon atoms. Exemplary amphoteric and zwitterionic surfactants for use in shampoos of the present invention include laurylamine oxide, cocodimethylsulfopropylbetaine, laurylbetaine, cocamidopropylbetaine, and sodium cocoamphoacetate.

[0039] A particularly preferred amphoteric or zwitterionic surfactant is cocamidopropyl betaine.

[0040] Mixtures of any of the aforementioned amphoteric or zwitterionic surfactants may also be suitable. A preferred mixture is a mixture of cocamidopropyl betaine with the aforementioned additional amphoteric or zwitterionic surfactant. A preferred additional amphoteric or zwitterionic surfactant is sodium cocoamphoacetate.

[0041] Particularly preferred compositions include a surfactant system comprising: 10-20% by weight of the composition of sodium lauryl sulfate or sodium lauryl ether sulfate (n)EO (n ranges from 1 to 3), 0.5-5% by weight of the composition of cocamidopropyl betaine, and 0.5-5% by weight of the composition of sodium cocoamphoacetate or sodium lauryl cocoamphoacetate.

[0042] Other ingredients The composition may also include one or more of the following non-essential ingredients:

[0043] pH adjuster 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 an alkaline agent (e.g., sodium hydroxide, etc.) or an acidic agent (e.g., citric acid, etc.) as is well known in the art.

[0044] cationic polymer Cationic polymers are preferred ingredients in hair care compositions according to the present invention to enhance the performance of the composition.

[0045] The cationic polymer may be a homopolymer or may be formed from two or more types of monomers. The molecular weight of the polymer is generally in the range of 5,000 to 10,000,000, typically at least 10,000, and preferably in the range of 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.

[0046] The cationic nitrogen-containing group is generally present as a substituent on a portion of all the monomer units of the cationic polymer. Therefore, if the polymer is not a homopolymer, it can contain spacer 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 obtain a polymer with a cationic charge density in the desired range.

[0047] Suitable cationic conditioning polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functional groups with water-soluble spacer monomers, such as (meth)acrylamide, alkyl and dialkyl (meth)acrylamides, alkyl (meth)acrylates, vinyl caprolactone, and vinyl pyrrolidine. The alkyl and dialkyl-substituted monomers preferably have C1-C7 alkyl groups, more preferably C1-3 alkyl groups. Other suitable spacers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol, and ethylene glycol.

[0048] The cationic amines may be primary, secondary, or tertiary amines, depending on the particular species and the pH of the composition. Generally, secondary and tertiary amines, especially tertiary amines, are preferred.

[0049] Amine-substituted vinyl monomers and amines can be polymerized in the amine form and then converted to ammonium by quaternization.

[0050] The cationic conditioning polymer can comprise a mixture of monomer units derived from amine- and / or quaternary ammonium-substituted monomers and / or compatible spacer monomers.

[0051] Suitable cationic conditioning polymers include, for example: 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, New Jersey, USA) under the LUVIQUAT trade name (e.g., LUVIQUAT FC 370); b) 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 trade name GAFQUAT (e.g., GAFQUAT 755N); c) cationic diallyl quaternary ammonium-containing polymers, including, for example, dimethyldiallylammonium chloride homopolymer and copolymer of acrylamide and dimethyldiallylammonium chloride, known in the industry (CTFA) as Polyquaternium 6 and Polyquaternium 7, respectively; d) mineral acid salts of amino-alkyl 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); e) Cationic polyacrylamides (described in WO 95 / 22311). Preferred cationic conditioning polymers that can 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 in the range of 0.1 to 4 meq / g.

[0052] Cationic polysaccharide polymers suitable for use in the compositions of the present invention include those of the formula: AO-[RN + (R 1 )(R 2 )(R 3 )X - ], where A is an anhydroglucose residue, such as a starch or cellulose anhydroglucose residue, and R is an alkylene, oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or a combination thereof. 1 ,R 2 and R 3independently represent an alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl group, each group 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 (total carbon atoms) is preferably about 20 or less, and X is an anionic counterion.

[0053] Cationic celluloses are available from Amerchol Corp. (Edison, NJ, USA) in their Polymer JR™ and LR™ series of polymers as salts of hydroxyethyl cellulose reacted with trimethylammonium-substituted epoxides, known in the industry (CTFA) as Polyquaternium 10. Another type of cationic cellulose is a polymeric quaternary ammonium salt of hydroxyethyl cellulose reacted with lauryldimethylammonium-substituted epoxide, 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.

[0054] Other suitable cationic polysaccharide polymers include quaternary nitrogen-containing cellulose ethers (e.g., as described in U.S. Pat. No. 3,962,418) and copolymers of etherified cellulose and starch (e.g., as described in U.S. Pat. No. 3,958,581).

[0055] 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 under the JAGUAR trademark series).

[0056] Examples are JAGUAR C13S, which has a low degree of cationic group substitution and high viscosity, JAGUAR C15, which has a medium degree of substitution and low viscosity, JAGUAR C17, which has a high degree of substitution and high viscosity, JAGUAR C16, a hydroxypropylated cationic guar derivative containing low levels of substitution and cationic quaternary ammonium groups, and JAGUAR 162, a high clarity, medium viscosity guar with a low degree of substitution.

[0057] Preferably, the cationic conditioning polymer is selected from cationic cellulose and cationic guar derivatives. Particularly preferred cationic polymers are JAGUAR C13S, JAGUAR C15, JAGUAR C17, JAGUAR C16 and JAGUAR C162. Particularly preferred is guar hydroxypropyltrimonium chloride.

[0058] The cationic conditioning polymer is generally present in the compositions of the invention in an amount 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.

[0059] When a cationic conditioning polymer is present in the hair care composition according to the present invention, the copolymer has an average diameter (D 3、2 Preferably, the emulsion particles have a particle size (measured by light scattering using a Malvern particle sizer).

[0060] The hair care compositions of the present invention are preferably aqueous, i.e., they have water or an aqueous solution or a lyotropic liquid crystalline phase as the main component. Suitably, the composition comprises 50 to 98 wt. %, preferably 60 to 90 wt. %, of water, based on the total weight of the composition.

[0061] silicone The anti-dandruff hair composition may further comprise 0.1 to 10% by weight, preferably 0.1 to about 8% by weight, more preferably about 0.3 to about 5% by weight of silicone.

[0062] Preferred suitable silicones may include polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, polyethersiloxane copolymers, aminosilicones and mixtures thereof.

[0063] The silicone may be present as free silicone oil or in the form of a silicone emulsion.

[0064] 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 in the range of 10 to 1,000 nm, most preferably from about 100 to about 500 nm.

[0065] Aminosilicones are often incorporated into hair compositions. Aminosilicones are silicones containing at least one primary amine, secondary amine, tertiary amine, or quaternary ammonium group. High molecular weight silicone gums are also available. Another useful type is crosslinked silicone elastomers such as dimethicone / vinyl / dimethicone crosspolymers (e.g., Dow Corning 9040 and 9041).

[0066] 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 all dimethiconol emulsions or microemulsions. Amodimethicone emulsions such as DC939 (manufactured by Dow Corning) and SME253 (manufactured by GE Silicones) are also suitable.

[0067] suspending agent Preferably, the hair care composition of the present invention further comprises 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 acrylic acid esters, crosslinked copolymers of acrylic acid and acrylate esters, heteropolysaccharide gums, and crystalline long-chain acyl derivatives. The long-chain acyl derivative is preferably 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 a pearlescent appearance to the composition. Polyacrylic acid is commercially available as Carbopol 420, Carbopol 488, or Carbopol 493. Polymers of acrylic acid crosslinked with polyfunctional agents may also be used. These 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 acrylic acid ester is Carbopol 1342. All Carbopol™ materials are available from Goodrich.

[0068] Suitable cross-linked polymers of acrylic acid and acrylate esters are Pemulen TR1 or Pemulen TR2.A suitable heteropolysaccharide gum is xanthan gum, for example that available as Kelzan mu.

[0069] Mixtures of any of the above suspending agents may be used. Mixtures of crosslinked polymers of acrylic acid and crystalline long chain acyl derivatives are preferred.

[0070] When included, the suspending agent will generally be present in the hair care composition of the present invention in an amount of from 0.1 to 10% by weight, preferably from 0.5 to 6% by weight, more preferably from 0.9 to 4% by weight, based on the total weight of the composition.

[0071] Non-silicone oily conditioning ingredients Compositions according to the present invention may also include dispersed non-volatile water-insoluble oily conditioning agents.

[0072] This ingredient is dispersed in the composition in the form of droplets that form a discontinuous phase separate from the aqueous continuous phase of the composition. In other words, the oily conditioning agent is present in the shampoo composition in the form of an oil-in-water emulsion.

[0073] By "insoluble" is meant that the material is not soluble in water (distilled or equivalent) at a concentration of 0.1% (w / w) at 25°C. Suitably, the D[3,2] average droplet size of the oily conditioning ingredient is at least 0.4, preferably at least 0.8, more preferably at least 1 μm. Furthermore, the D[3,2] average droplet size of the oily conditioning ingredient is preferably 10 or less, more preferably 8 or less, more preferably 5 or less, even more preferably 4 or less, and most preferably 3.5 μm or less.

[0074] The oily conditioning agent may be suitably selected from oily or fatty materials, and mixtures thereof.

[0075] Oily or fatty materials are preferred conditioning agents in shampoo compositions of the present invention because they add shine to the hair and also enhance dry combing and dry hair feel.

[0076] Preferred oily and fatty materials generally have a viscosity of less than 5 Pa.s, more preferably less than 1 Pa.s, most preferably less than 0.5 Pa.s, for example less than 0.1 Pa.s, measured at 25°C in a Brookfield viscometer (e.g., Brookfield RV) using spindle 3 operating at 100 rpm.

[0077] Oily and fatty materials having higher viscosities may also be used. For example, materials having viscosities as high as 65 Pa.s may be used. The viscosity of such materials (i.e., materials having a viscosity of 5 Pa.s or greater) may be measured by a glass capillary viscometer as further described in Dow Corning Corporate Test Method CTM004, dated July 20, 1970.

[0078] Suitable oily or fatty materials are selected from hydrocarbon oils, fatty esters and mixtures thereof.

[0079] 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 from about 12 to about 30 carbon atoms. Branched-chain hydrocarbon oils can contain, and typically contain, more carbon atoms. Polymeric hydrocarbons of alkenyl monomers, such as C2-C6 alkenyl monomers, are also suitable. These polymers can be straight-chain or branched-chain polymers. Linear-chain polymers are typically relatively short in length and generally have a total number of carbon atoms as described above for straight-chain hydrocarbons. Branched-chain polymers can have substantially longer chain lengths. The number average molecular weight of such materials can vary widely, but is typically up to about 2,000, preferably from about 200 to about 1,000, and more preferably from about 300 to about 600.

[0080] 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. Branched-chain isomers of these compounds, as well as branched-chain isomers of longer chain hydrocarbons, can also be used. Exemplary branched-chain isomers are highly branched saturated or unsaturated alkanes, such as permethyl-substituted isomers of hexadecane and eicosane sold by Permethyl Corporation, such as 2,2,4,4,6,6,8,8-dimethyl-10-methylundecane and 2,2,4,4,6,6-dimethyl-8-methylnonane. A further example of a hydrocarbon polymer is polybutene, such as a copolymer of isobutylene and butene. A commercially available material of this type is L-14 polybutene manufactured by Amoco Chemical Co. (Chicago, Illinois, USA).

[0081] Particularly preferred hydrocarbon oils are various grades of mineral oil. Mineral oils are clear, oily liquids obtained from petroleum oils after waxes have been removed and the more volatile fractions have been removed by distillation. The fraction between 250°C and 300°C is called mineral oil and consists of a mixture of hydrocarbons ranging from C16H34 to C21H4. Suitable commercial materials of this type include Sirius M85 and Sirius M125, both available from Silkolene.

[0082] Suitable fatty acid esters are characterized by having at least 10 carbon atoms and include esters with hydrocarbyl chains derived from fatty acids or alcohols, such as monocarboxylic acid esters, polyhydric alcohol esters, and di- and tricarboxylic acid esters. The hydrocarbyl groups of the fatty esters herein may also contain or be covalently bound to other compatible functional groups, such as amide and alkoxy moieties, such as ethoxy or ether linkages. Monocarboxylic acid esters include alcohol and / or acid esters of the formula R'COOR, where R' and R independently represent alkyl or alkenyl groups, and the total carbon atoms of R' and R is at least 10, preferably at least 20.

[0083] Specific examples include alkyl and alkenyl esters of fatty acids having an aliphatic chain with about 10 to about 22 carbon atoms, alkyl and / or alkenyl fatty alcohol carboxylic acid esters having an aliphatic chain derived from alkyl and / or alkenyl alcohols having about 10 to about 22 carbon atoms, and benzoate esters of fatty alcohols having about 12 to 20 carbon atoms.

[0084] The monocarboxylic acid ester need not contain more than one chain having at least 10 carbon atoms, as long as the total number of carbon atoms in the aliphatic chain is at least 10. Examples include isopropyl isostearate, hexyl laurate, isohexyl laurate, isohexyl palmitate, isopropyl palmitate, decyl oleate, isodecyl oleate, hexadecyl stearate, decyl stearate, isopropyl isostearate, dihexyldecyl adipate, lauryl lactate, myristyl lactate, cetyl lactate, oleyl stearate, oleyl oleate, oleyl myristate, lauryl acetate, cetyl propionate, and oleyl adipate. Di- and tri-alkyl esters and alkenyl esters of carboxylic acids can also be used. These include, for example, esters of C4-C8 dicarboxylic acids such as C7-C22 esters (preferably C1-C9) of succinic acid, glutaric acid, adipic acid, hexanoic acid, heptanoic acid, and octanoic acid. Examples include diisopropyl adipate, diisohexyl adipate, and diisopropyl sebacate. Other specific examples include isocetyl stearoyl stearate and tristearyl citrate.

[0085] Polyhydric alcohol 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 polyfatty acid esters, ethoxylated glyceryl 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.

[0086] Particularly preferred fatty acid esters are mono-, di-, and triglycerides, more specifically, mono-, di-, and tri-esters of glycerol with long-chain carboxylic acids, such as C7 to C22 carboxylic acids. A variety of these types of materials can be derived from vegetable and animal fats and oils, such as 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 and tristearin glyceryl dilaurate.

[0087] Specific examples of preferred materials include cocoa butter, palm stearin, sunflower oil, soybean oil, coconut oil, etc. The oily or fatty material is suitably present in an amount of 0.05 to 10, preferably 0.2 to 5, more preferably about 0.5 to 3% by weight.

[0088] Compositions of the present invention preferably contain no more than 3% by weight of styling polymer, more preferably less than 1%, preferably less than 0.1% by weight of styling polymer, and optimally no styling polymer.

[0089] In hair treatment compositions containing conditioning agents, it is preferred that a cationic polymer is also present.

[0090] Adjuvants The compositions of the present invention may also contain adjuvants suitable for hair care. Generally, such ingredients are included individually in an amount of up to 2% by weight of the total composition, preferably up to 1% by weight.

[0091] Suitable hair care adjuvants include: (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, such as dipeptides and tripeptides. Amino acids can also be added in the form of protein hydrolysates, such as 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 composition of the present invention is isoleucine and glucose. A particularly preferred amino acid nutrient is arginine. (ii) Hair fiber benefit agents. Examples are ceramides to moisturize the fiber and maintain cuticle integrity. Ceramides are available 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.

[0092] minor ingredients The compositions may also contain other ingredients to enhance performance and / or consumer acceptance. Such ingredients include fragrances (encapsulated or free, or both), colorants, dyes and pigments, pearlescent or opacifying agents, viscosity modifiers, stabilizers, and preservatives. Suitable preservative systems include sodium benzoate and sodium salicylate, pH adjusted using sodium hydroxide and citric acid H2O. Alternative preservative systems containing formaldehyde include MIT and DMDM ​​hydantoin.

[0093] Product form The composition is preferably a personal care composition, more preferably a shampoo, conditioner, spray, mousse, gel, wax or lotion.Particularly preferred product forms are shampoo, after-wash conditioner (leave-in and rinse-out) and hair treatment products, such as hair essence.Rinse-off products are preferred, and shampoos are particularly preferred.

[0094] The composition is preferably formulated as a composition for treating hair and subsequent rinsing.

[0095] Particularly preferred hair care compositions are shampoo compositions. The total amount of surfactant (including any co-surfactant and / or any emulsifier) ​​in shampoo compositions of the present invention is generally from 5 to 30% by weight of the composition, preferably from 10 to 25% by weight, more preferably from 15 to 20% by weight.

[0096] How to use The compositions of the present invention can be used in medical or non-medical products.

[0097] The preferred method of use is to apply 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 about 2 to about 10 minutes.

[0098] The invention will now be further described with reference to the following non-limiting examples, in which examples according to the invention are designated by numbers and comparative examples by letters.

[0099] [Example] Preparation of metal-piroctone complexes

[0100] [Example 1] Copper Piroctone -While stirring, add dropwise 0.03 mol of CuCl2·4H2O dissolved in water. - Demineralized water is added to precipitate the viscous solid. The suspension is stirred at room temperature for 2-4 hours. - The separated white solid is washed and dried over P2O5 at a temperature of 50°C under vacuum for 24 hours.

[0101] [Example 2] Manganese Piroctone -0.04 mol of octopirox is dissolved in ethanol. - Add dropwise 0.03 mol of MnCl2·4H2O dissolved in water while stirring. - Demineralized water is added to precipitate the viscous solid. The suspension is stirred at room temperature for 2-4 hours. - The separated white solid is washed and dried over P2O5 at a temperature of 50°C under vacuum for 24 hours.

[0102] [Example A] Zinc Piroctone -0.04 mol of octopirox is dissolved in ethanol. - Under stirring, 0.03 mol of ZnCl2 dissolved in water is added dropwise. - Demineralized water is added to precipitate the viscous solid. The suspension is stirred at room temperature for 2-4 hours. - The separated white solid is washed and dried over P2O5 at a temperature of 50°C under vacuum for 24 hours.

[0103] [Example 5] Copper piroctone prepared in shampoo formulations An aqueous mixture of sodium lauryl ether sulfate 1EO, cocamidopropyl betaine and guar hydroxypropyltrimonium chloride was prepared. - Sodium salicylate dissolved in water was added to this mixture, followed by the addition of phenoxyethanol. - The pH was adjusted to pH 6 using citric acid (50% by weight). -Sodium chloride was used to adjust the viscosity. -Octopirox is slowly added to the formulation, followed by the copper chloride solution in water. -Additional water was added.

[0104] Solubility of metal piroctone complexes. The solubilities of metal piroctone complexes in a 5 wt % aqueous solution of SLES 1EO (sodium lauryl ether sulfate) at 20° C. are listed in Table 1.

[0105] [Table 1]

[0106] Shampoo composition The following shampoo compositions were prepared:

[0107] [Table 2]

[0108] Solubility of metal piroctone complexes in shampoos -Visually determined solubility.

[0109] [Table 3]

[0110] In vitro deposition experiments on hair substrates HPLC-UV method Agilent 1100 HPLC system Agilent Eclipse plus C18 100×4.6; 3.5um column Column oven temperature 30 °C, 1.5 ml / min, 302 nm 10 nm ref = 360 / 50 nm pressure approx. 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

[0111] Hairpiece Cleaning Protocol: All hair switches were pre-treated by washing with a 14 wt% SLES solution to standardize. The switches were then treated using a wash process under standard conditions with the relevant octopirox or metal-piroctone complex-containing shampoo base. The protocol was applied to three hair switches for each composition.

[0112] Once dry, the switches were each treated with ethanol to extract the octopirox or complex.

[0113] The extract was analyzed by HPLC-UV and the concentration of piroctone was calculated.

[0114] Piroctone complex deposition results

[0115] [Table 4]

[0116] The results demonstrate that the inventive examples enhanced the deposition of piroctone on hair.

[0117] [Examples 5, 6 and D] The UV stability of ethanolic solutions of copper piroctone and manganese piroctone (0.5 mM) was measured and compared with that of a 1 mM solution of octopirox.

[0118] After 5 hours of UV irradiation (UVA 180uW / cm2, UVB 210uW / cm2), it was found that manganese piroctone, copper piroctone, and octopirox (piroctone) were degraded by 3.2%, 1.8%, and 46%, respectively.

[0119] These results demonstrate the improved UV stability of the metal piroctone complexes.

Claims

1. 1. A personal care composition comprising a SLES1EO surfactant and 0.1 to 0.8 wt. % of a manganese and / or copper piroctone complex, A personal care composition wherein the manganese and / or copper piroctone complex has a solubility of 2 wt % or less in a 5 wt % aqueous solution of SLES1EO surfactant at 20°C.

2. 10. The personal care composition of claim 1, wherein the manganese and / or copper piroctone complex is copper bispiroctone and / or manganese bispiroctone.

3. 10. The personal care composition of claim 1, further comprising an amphoteric surfactant.

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

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

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

7. 7. The personal care composition of claim 1 which is a shampoo.

8. 1. Use of 0.1 to 0.8 wt. % of a manganese and / or copper piroctone complex in a hair treatment composition to prevent UV degradation of a Pictron compound, comprising: the hair treatment composition comprises a SLES1EO surfactant; The manganese and / or copper piroctone complex has a solubility of 2% by weight or less in a 5% by weight aqueous solution of SLES1EO surfactant at 20°C.

Images