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WO1999066886A1 - Composition antimicrobienne de traitement capillaire - Google Patents

Composition antimicrobienne de traitement capillaire Download PDF

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Publication number
WO1999066886A1
WO1999066886A1 PCT/EP1999/004154 EP9904154W WO9966886A1 WO 1999066886 A1 WO1999066886 A1 WO 1999066886A1 EP 9904154 W EP9904154 W EP 9904154W WO 9966886 A1 WO9966886 A1 WO 9966886A1
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WO
WIPO (PCT)
Prior art keywords
particles
composition
microns
hair treatment
metal pyrithione
Prior art date
Application number
PCT/EP1999/004154
Other languages
English (en)
Inventor
Peter Gallagher
Peter Christopher Konidaris
Tipawan Kreu-Nopakun
Edwin John Staples
Original Assignee
Unilever Plc
Unilever N.V.
Hindustan Lever Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever Plc, Unilever N.V., Hindustan Lever Limited filed Critical Unilever Plc
Priority to AU47726/99A priority Critical patent/AU4772699A/en
Publication of WO1999066886A1 publication Critical patent/WO1999066886A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic

Definitions

  • This invention relates to antimicrobial hair treatment compositions for topical application to human hair and scalp for the treatment of, for example, dandruff.
  • the invention relates to a hair treatment composition comprising a surfactant, water- insoluble antimicrobial particles and a cationic polymer which serves to enhance the deposition and retention of the particles on the hair and/or the scalp from the composition.
  • Insoluble particulate metal pyrithiones are acknowledged as antimicrobial agents which can be incorporated into antimicrobial compositions, such as antidandruff hair shampoos and conditioners.
  • the zinc salt hereinafter referred to as ZnPTO
  • ZnPTO zinc salt
  • dispersed particles of the ZnPTO are suspended in the composition, which is then applied to the hair to deposit the ZnPTO on the hair and scalp.
  • a problem encountered with such compositions is that it is difficult to obtain a stable dispersion containing ZnPTO, since its specific gravity and insolubility leads to precipitation and separation during storage. Steps taken to prevent precipitation and separation of the ZnPTO particles have hitherto included restriction of the formulational base to highly viscous emulsions or gels, e.g., by incorporation of thickeners or bulking agents to give structural viscosity to the system and prevent ZnPTO settlement . Such an approach is frequently impractical for shampoo compositions and can give cloudy, aesthetically- inferior products.
  • the anti -dandruff benefits attainable from particles of ZNPTO incorporated in hair treatment compositions are frequently limited, owing to a poor level of deposition on the intended site; namely the hair and/or the scalp, but particularly the scalp.
  • a further problem encountered with such compositions is that acceptable aesthetic properties, such as pearlescence, of the compositions are often difficult to achieve.
  • the general approach taken to improve the pearlescence is to incorporate pearlescent materials such as ethylene glycol distrearate in the compositions.
  • pearlescent materials such as ethylene glycol distrearate
  • Such an approach alone is frequently dissatisfactory owing to the presence of metal pyrithione particles interfering with the ability of the pearlescent materials to deliver acceptable pearlescence.
  • ZnPTO crystals having a flat plate-like morphology interfere less with pearlescers in such compositions.
  • EP 34385 describes an aesthetically improved anti-dandruff hair care composition comprising flat, platelet shaped ZnPTO crystals.
  • JP 8283242A describes a "mica like" shaped l-hydroxy-2- pyridinethione heavy metal salt for use in hair care compositions. The mica shaped crystals are said not to impede pearlescence.
  • antimicrobial hair treatment compositions which have good mechanical stability, good optical properties and excellent anti-dandruff ability can be obtained by utilising needle-shaped particles of insoluble particulate metal pyrithione in combination with a deposition aid.
  • an antimicrobial hair treatment composition comprising:
  • the invention also provides a method of treating dandruff comprising applying to the hair a composition according to the first aspect of the present invention.
  • an antimicrobial hair treatment composition of particles of an insoluble particulate metal pyrithione in which at least 50% by number of the particles are needle shaped particles having a length of between 1 and 50 microns.
  • particles of an insoluble particulate metal pyrithione in which at least 50% by number of the particles are needle shaped particles having a length of between 1 and 50 microns for improving pearlescence of an antimicrobial hair treatment composition.
  • the insoluble particulate metal pyrithione may be represented by the following general formula:
  • M is a polyvalent metal ion and n corresponds to the valency of M.
  • M include magnesium, barium, strontium, zinc, cadmium, tin and zirconium. Especially preferred is zinc.
  • needle-shaped particle used herein is used to describe a generally elongate three dimensional particle of any transverse cross-sectional shape, the particle having one dimension, the length, substantially greater than the other two. By “substantially” is meant greater by a factor of at least two, preferably at least 3 and most preferably at least 5. Although the cross-sectional shape of the particle is not particularly critical it is typically polygonal .
  • the needle-shaped particles of metal pyrithione have a size distribution in which at least about 50% of the particles, by number of the particles, have a length of between 1 and 50 microns.
  • the size distribution is such that at least about 50% of the particles, by number of the particles, have a length of between 2 and 40 microns; most preferably between 4 and 30 microns and even more preferably between 5 and 15 microns; the most preferred length being between 10 and 15 microns.
  • the size distribution is such that at least about 70% of the particles, by number of the particles, have a length of between 2 and 40 microns; most preferably between 4 and 30 microns and even more preferably between 5 and 15 microns; the most preferred length is between 10 and 15 microns.
  • the size distribution is such that at least about 80% of the particles, by number of the particles, have a length of between 2 and 40 microns; most preferably between 4 and 30 microns and even more preferably between 5 and 15 microns; the most preferred length being between 10 and 15 microns.
  • the dimensions of the needle shaped particles can be determined most conveniently visually using an electron microscope .
  • the amount of metal pyrithione incorporated into the compositions of the invention may depend on the type of composition and the exact nature of the material used.
  • a preferred amount of metal pyrithione is from about 0.001 to about 5% by weight of the total composition, more preferably from about 0.05 to about 3% by weight, most preferably between 0.1 and 1%.
  • the needle-shaped particles of a metal pyrithione may be prepared by mixing a water-soluble salt of pyrithione (such as sodium pyrithione) and a dispersant (such as DARVAN 1, a dispersant which is the sodium salt of polymerized alkyl naphthalene sulphonic acid) while maintaining stirring of this mixture at a temperature of between 20 and 60 degrees Celsius.
  • a dispersant such as DARVAN 1, a dispersant which is the sodium salt of polymerized alkyl naphthalene sulphonic acid
  • the stirring is suitably effected using a paddle mixer having a paddle speed of from 50 to 150 rpm.
  • the amount of dispersant added should be sufficient to provide from about 0.05 to about 10% by weight of dispersant, based on the total weight of the final reaction mixture.
  • aqueous solution of a polyvalent metal salt for example a zinc salt such as zinc sulphate monohydrate
  • a polyvalent metal salt for example a zinc salt such as zinc sulphate monohydrate
  • the amount of polyvalent metal salt is used in a slight (such as 5%) stoichiometric excess, relative to the amount of water-soluble pyrithione salt employed.
  • the temperature of the reaction mixture should be maintained at between 20 and 60 degree Celsius, and stirring of the reaction mixture continued until all of the polyvalent metal salt solution has been added and a precipitate forms.
  • the resulting rods and needles of insoluble zinc pyrithione salt are collected by vacuum filtration and washed in cold water.
  • the rods and needles of ZnPTO produced by this method are generally about 0.1 to 1.0 microns width and 1 to 50 microns in length.
  • the composition according to the invention also comprises at least one surfactant, preferably chosen from anionic, cationic, nonionic, amphoteric and zwitterionic surfactants, and mixtures thereof .
  • a particularly preferred hair treatment composition in accordance with the invention is a shampoo composition in which at least one surfactant provides a deterging benefit.
  • the deterging surfactant is preferably selected from anionic, nonionic, amphoteric and zwitterionic surfactants, and mixtures thereof .
  • Suitable anionic surfactants include the alkyl sulphates, alkyl ether sulphates, alkaryl sulphonates, alkanoyl isethionates, alkyl succinates, alkyl sulphosuccinates, N- alkoyl sarcosinates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, and alpha-olefin sulphonates, especially their sodium, magnesium ammonium and mono-, di- and triethanolamine salts.
  • the alkyl and acyl groups generally contain from 8 to 18 carbon atoms and may be unsaturated.
  • alkyl ether sulphates, alkyl ether phosphates and alkyl ether carboxylates may contain from oneto 10 ethylene oxide or propylene oxide units per molecule, and preferably contain 2 to 3 ethylene oxide units per molecule.
  • anionic surfactants include sodium oleyl succinate, ammonium lauryl sulphosuccinate, ammonium lauryl sulphate, sodium dodecylbenzene sulphonate, triethanolamine dodecylbenzene sulphonate, sodium cocoyl isethionate, sodium lauroyl isethionate and sodium N-lauryl sarcosinate.
  • the most preferred anionic surfactants are sodium lauryl sulphate, triethanolamine lauryl sulphate, triethanolamine monolauryl phosphate, sodium lauryl ether sulphate 1E0, 2E0 and 3E0, ammonium lauryl sulphate and ammonium lauryl ether sulphate 1E0, 2E0 and 3E0.
  • Nonionic surfactants suitable for use in compositions of the invention may include condensation products of aliphatic
  • alkylene oxides usually ethylene oxide and generally having from 6 to 30 ethylene oxide groups.
  • suitable nonionics include mono- or di-alkyl alkanolamides .
  • Example include coco mono- or di- ethanolamide and coco mono-isopropanolamide .
  • Amphoteric and zwitterionic surfactants suitable for use in compositions of the invention may include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulphobetaines (sultaines) , alkyl glycinates, alkyl carboxyglycinates, alkyl amphopropionates, alkylamphoglycinates alkyl amidopropyl hydroxysultaines, acyl taurates and acyl glutamates, wherein the alkyl and acyl groups have from 8 to 19 carbon atoms.
  • Examples include lauryl amine oxide, cocodimethyl sulphopropyl betaine and preferably lauryl betaine, cocamidopropyl betaine and sodium cocamphopropionate .
  • the surfactants are present in shampoo compositions of the invention in an amount of from 0.1 to 50% by weight of the composition, preferably from 0.5 to 30% by weight.
  • Hair treatment compositions in accordance with the invention may also take the form of hair conditioning compositions, which preferably comprise one or more cationic surfactants.
  • hair conditioning compositions which preferably comprise one or more cationic surfactants.
  • cationic surfactants is especially preferred, because these ingredients are capable of providing conditioning benefits to hair.
  • cationic surfactants include:
  • quaternary ammonium hydroxides e.g., tetramethylammonium hydroxide, alkyltrimethylammonium hydroxides wherein the alkyl group has from about 8 to 22 carbon atoms, for example octyltrimethylammonium hydroxide, dodecyltrimethy- ammonium hydroxide, hexadecyltrimethylammonium hydroxide, cetyltrimethylammonium hydroxide , octyldimethylbenzylammonium hydroxide, decyldimethyl- benzylammonium hydroxide, stearyldi-methylbenzylammonium hydroxide, didodecyldimethylammonium hydroxide, dioctadecyldimethylammonium hydroxide, tallow trimethylammonium hydroxide, cocotrimethylammonium hydroxide, and the corresponding salts thereof, e.g., chlorides Cetylpyr
  • the level of cationic surfactant is preferably from 0.01 to 10%, more preferably 0.05 to 5%, most preferably 0.1 to 2% by weight of the composition.
  • Hair treatment compositions of the invention may also contain one or more conditioning agents, preferably selected from silicones, protein hydrolyzates and quaternised protein hydrolysates and other materials which are known in the art as having desirable hair conditioning properties.
  • conditioning agents preferably selected from silicones, protein hydrolyzates and quaternised protein hydrolysates and other materials which are known in the art as having desirable hair conditioning properties.
  • Silicones are the most preferred conditioning agents.
  • Suitable silicones include volatile and non-volatile silicones, such as for example polyalkylsiloxanes, polyalkylaryl siloxanes, siloxane gums and resins, cyclomethicones, aminofunctional silicones, quaternary silicones and mixtures thereof.
  • Silicone oil is a particularly preferred conditioning agent for hair.
  • the silicone may be in the form of a low viscosity oil which may contain a high viscosity oil or gum in solution.
  • the high viscosity material may be in the form of an emulsion in water.
  • the emulsion may be of high viscosity oil or of a solution of gum in a lower viscosity oil.
  • the particle size of the oil phase may be anywhere in the range from 30 nanometres to up to 20 microns average size .
  • the silicone oil may suitably be a polydimethylsiloxane with an average particle size of less than 20 microns and preferably less than 2 microns. Small particle size enables a more uniform distribution of silicone conditioning agent for the same concentration of silicone in the composition.
  • a silicone with a viscosity in the range 1- 20 million cst is used.
  • the silicone can be cross-linked.
  • Suitable protein hydrolysates include lauryl dimonium hydroxy propylamino hydrolysed animal protein, available commercially under the trade name AMEQUAT L, and hydrolysed keratin containing sulphur-bearing amino acids, available commercially under the trade name CROQUAT WKP .
  • the hair treatment composition also comprises a polymeric water-soluble cationic polymer as a deposition aid for the needle-shaped particles.
  • deposition aid is defined herein as an agent which enhances deposition of the needle-shaped particles of metal pyrithione on the intended site, i.e., the hair and/or the scalp.
  • the deposition aid will generally be present at levels of from 0.01 to 5%, preferably from about 0.05 to 1%, more preferably from about 0.08% to about 0.5% by weight.
  • the cationic charge density which is defined as the reciprocal of the molecular weight of a monomeric unit of the polymer containing 1 charge is at least 0.1 meq/g, preferably above 0.8 or higher.
  • the cationic charge density should not exceed 4 meq/g, it is preferably less than 3 and more preferably less than 2 meq/g.
  • the charge density can be measured using conductimetric analysis and should be within the above limits at the desired pH of use, which will in general be from about 3 to 9 and preferably between 4 and
  • Preferred deposition aids are cationic derivatives of guar gum and cationic polyacrylamides .
  • Suitable cationic derivatives of guar gum are JAGUAR C13S, which has a low degree of substitution of the cationic groups and high viscosity.
  • JAGUAR C15 having a moderate degree of substitution and a low viscosity
  • JAGUAR C17 high degree of substitution, high viscosity
  • JAGUAR C16 which is a hydroxypropylated cationic guar derivative containing a low level of substituent groups
  • JAGUAR 162 which is a high transparency, medium viscosity guar having a low degree of substitution.
  • Particularly preferred deposition aids are Jaguar C13S with a cationic charge density of 0.8 meq/g.
  • Suitable cationic polyacrylamides are described in WO 95/22311 whose contents are incorporated herein by reference .
  • the composition may further comprise from 0.1 to 5 % of a suspending agent.
  • a suspending agent examples are polyacrylic acids, cross linked polymers of acrylic acid, copolymers of acrylic acid with a hydrophobic monomer, copolymers of carboxylic acid- containing monomers and acrylic esters, cross-linked copolymers of acrylic acid and acrylate esters, heteropolysaccharide gums and crystalline long chain acyl derivatives.
  • the long chain acyl derivative is desirably selected from ethylene glycol stearates, alkanolamides of fatty acids having from 16 to 22 carbon atoms and mixtures thereof.
  • Polyacrylic acid is available commercially as Carbopol 420, Carbopol 488 or Carbopol 493.
  • Polymers of acrylic acid cross-linked with a polyfunctional agent may also be used, they are available commercially as Carbopol 910, Carbopol 934, Carbopol 940, Carbopol 941 and Carbopol 980.
  • An example of a suitable copolymer of a carboxylic acid containing a monomer and acrylic acid esters is
  • Carbopol 1342 All Carbopol materials are available from Goodrich and Carbopol is a trade mark.
  • a further suitable suspending agent is dihydrogenated tallow phthalic acid amide (available from Stepan under the trademark Stepan TAB- 2) .
  • 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.
  • a fatty alcohol material Another ingredient that may advantageously be incorporated into hair treatment compositions of the invention is a fatty alcohol material.
  • the use of these materials is especially preferred in conditioning compositions of the invention, in particular conditioning compositions which comprise one or more cationic surfactant materials.
  • conditioning compositions which comprise one or more cationic surfactant materials.
  • the combined use of fatty alcohol materials and cationic surfactants in conditioning compositions is believed to be especially advantageous, because this leads to the formation of a lamellar phase, wherein the cationic surfactant is dispersed.
  • Preferred fatty alcohols comprise from 8 to 22 carbon atoms, more preferably 16 to 20.
  • Examples of preferred fatty alcohols are cetyl alcohol and stearyl alcohol. The use of these materials is also advantageous in that they contribute to the overall conditioning properties of compositions of the invention.
  • the level of fatty alcohol materials is conveniently from 0.01 to 10%, preferably from 0.1 to 5% by weight of the composition.
  • the weight ratio of cationic surfactant to fatty alcohol is preferably from 10:1 to 1:10, more preferably from 4:1 to 1:8, most preferably from 1:1 to 1:4.
  • a further ingredient that may be desirably included in the hair treatment composition is a pearlescent material.
  • Suitable pearlescent materials include ethylene glycol distearate, ethylene glycol monostearate, guanine and titanium dioxide coated micas, bismith oxychloride, and stearic monoethanol amide.
  • the level of pearlescent material present in the composition is generally 0.1% to 5%, preferably from 0.3% to 3% by weight of the composition.
  • the hair treatment compositions of the invention are preferably aqueous based.
  • the compositions suitably comprise water in amount of from about 20 to about 99% by weight of the total composition.
  • compositions of the invention are preferably rinse-off compositions, i.e., suitable for applying to the hair and/or scalp, left thereon for an appropriate period of time and then rinsed off with water.
  • shampoos and conditioners are a particularly preferred product form for compositions of the invention.
  • one or more additional ingredients conventionally incorporated into hair treatment formulations may be included in the compositions of the invention.
  • additional ingredients additional antimicrobial agents, foam boosters, perfumes, colouring agents, preservatives, thickeners, viscosity modifiers, proteins, polymers, buffering or pH adjusting agents, moisturising agents, herb or other plant extracts and other natural ingredients.
  • Example 1 The invention is further illustrated by way of the following non-limitative examples, in which all percentages are by weight based on total weight of the composition, unless otherwise specified.
  • Example 1 The invention is further illustrated by way of the following non-limitative examples, in which all percentages are by weight based on total weight of the composition, unless otherwise specified.
  • a sample of ZnPTO particles prepared as described hereinbefore was shaken thoroughly and 10 microlitres was removed by pipette and diluted with 18 mililitres of water. A small amount of the diluted sample was placed onto an aluminium stub and left to air dry for two hours afterwhich the stub plus diluted sample was placed under vacuum for 48 hours. The samples were then coated with gold Ca 5nm to aid conductivity before imaging at lOkv. Ten photographic images of the sample were taken. Total number (T) of whole needles in each photograph were counted and measured. Those particles having a length of between 1 and 50 microns, which dimension was substantially greater than its other two, represented "needle-shaped particles" (N) as defined hereinbefore. The percentage by number of the particles in the sample that were needle-shaped particles having a length of between 1 and 50 microns was accordingly determined by the calculation (N/T)X 100.
  • test shampoos were made from a common base, namely 14 % sodium lauryl ether sulphate (2EO) , 2% cocamidopropylbetaine, 0.1 % JAGUAR C13S (guar hydroxypropyltrimonium chloride, ex Rhodia) , 6% pearlising agent Mirasheen CP 820, ex Rhodia and suspending, colouring and preserving agents.
  • the following ZNPTO particles were additionally added to the test shampoos A to E.
  • Shampoos B and E contain ZnPTO particles in which at least 50% by number thereof are ZnPTO needles according to the present invention.
  • Shampoos A, C,and D contain standard size ZnPTO particles ex Olin and thus serve as comparative examples outside the present invention.
  • composition B containing needle-shaped ZnPTO is better than composition A, identical to B except for containing prior art ZnPTO particles.
  • composition E containing needle-shaped ZnPTO particles is better than compositions C and D, identical to E except for containing prior art ZnPTO particles.
  • Hair shampoo compositions in accordance with the present invention comprising needle-shaped particulate metal pyrithione and a deposition polymer were prepared using techniques well known in the art.
  • the ZnPTO particles were prepared as described herein.
  • the composition had the following formulation. INGREDIENT % BY WEIGHT
  • Vitamin E acetate 0.05

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Abstract

Cette composition antimicrobienne de traitement capillaire comprend: a) au moins un tensioactif, b) des particules d'un pyrithione métallique, particulaire, insoluble, dans lequel au moins 50 % environ du nombre des particules correspondent à des particules en forme d'aiguilles possédant une longueur comprise entre 1 et 50 microns, et c) un polymère cationique hydrosoluble, lequel constitue un agent de dépôt des particules de pyrithione métallique. Ces compositions de traitement capillaire combinent les propriétés recherchées d'efficacité contre les pellicules, de stabilité et d'attrait esthétique.
PCT/EP1999/004154 1998-06-24 1999-06-16 Composition antimicrobienne de traitement capillaire WO1999066886A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU47726/99A AU4772699A (en) 1998-06-24 1999-06-16 Antimicrobial hair treatment composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9813640.1 1998-06-24
GBGB9813640.1A GB9813640D0 (en) 1998-06-24 1998-06-24 Antimicrobial hair treatment composition

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WO1999066886A1 true WO1999066886A1 (fr) 1999-12-29

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AR (1) AR019705A1 (fr)
AU (1) AU4772699A (fr)
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WO (1) WO1999066886A1 (fr)

Cited By (28)

* Cited by examiner, † Cited by third party
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WO2000066072A1 (fr) * 1999-05-03 2000-11-09 The Procter & Gamble Company Shampooing offrant une combinaison a efficacite superieure de type antipelliculaire et conditionneur
US6242007B1 (en) * 1997-04-28 2001-06-05 Arch Chemicals, Inc. Non-spherical and non-platelet forms of pyrithione salts and methods of making same
WO2002000178A1 (fr) * 2000-06-27 2002-01-03 Unilever Plc Compositions contenant une pyrithione metallique
US6451300B1 (en) 1999-05-03 2002-09-17 The Procter & Gamble Company Anti-dandruff and conditioning shampoos containing polyalkylene glycols and cationic polymers
WO2003028682A1 (fr) * 2001-10-03 2003-04-10 The Procter & Gamble Company Shampooing contenant des particules et un agent facilitant le depot
US6649155B1 (en) 1999-05-03 2003-11-18 The Procter & Gamble Company Anti-dandruff and conditioning shampoos containing certain cationic polymers
US8685908B2 (en) 2011-02-28 2014-04-01 The Procter & Gamble Company Bar soap comprising pyrithione sources
US8980239B2 (en) 2011-10-07 2015-03-17 The Procter & Gamble Company Personal care compositions and methods of making same
US8978666B2 (en) 2010-02-16 2015-03-17 The Procter & Gamble Company Method for providing maximum malodor and irritation control
WO2015134645A1 (fr) * 2014-03-07 2015-09-11 The Procter & Gamble Company Compositions de soins personnels comprenant un composé de zinc et/ou de la pyrithione
US9272164B2 (en) 2011-10-07 2016-03-01 The Procter & Gamble Company Method of achieving improved hair feel
US9333157B2 (en) 2013-03-14 2016-05-10 The Procter & Gamble Company Bar soap compositions containing zinc pyrithione and a metal-pyridine oxide complex
US9375389B2 (en) 2013-04-18 2016-06-28 The Procter & Gamble Company Personal care compositions containing zinc pyrithione and a metal-phosphonate complex
US9504638B2 (en) 2012-05-11 2016-11-29 The Procter & Gamble Company Personal cleansing compositions comprising zinc pyrithione
WO2017089108A1 (fr) 2015-11-27 2017-06-01 Unilever N.V. Composition de nettoyage antimicrobienne
US9901584B2 (en) 2015-05-06 2018-02-27 The Procter & Gamble Company Methods of cosmetically treating skin conditions with a cosmetic personal cleansing composition
WO2018041544A1 (fr) 2016-08-30 2018-03-08 Unilever N.V. Composition de soins personnels
WO2018077602A1 (fr) 2016-10-27 2018-05-03 Unilever N.V. Composition de soins personnels
WO2018077958A1 (fr) 2016-10-27 2018-05-03 Unilever N.V. Composition de soins personnels comprenant des curcuminoïdes
WO2018172121A1 (fr) 2017-03-23 2018-09-27 Unilever N.V. Composition de soin capillaire
WO2018197118A1 (fr) 2017-04-26 2018-11-01 Unilever N.V. Composition de soin capillaire antipelliculaire comprenant de la pyrithione
US10201481B2 (en) 2014-03-07 2019-02-12 The Procter & Gamble Company Personal care compositions and methods of making same
CN110074995A (zh) * 2019-05-21 2019-08-02 福建省轻工业研究所 一种含无患子提取液的祛屑组合物
US10532013B2 (en) 2013-05-22 2020-01-14 The Procter And Gamble Company Method of achieving improved product rheology, cosmetic consumer acceptance and deposition
WO2020229199A1 (fr) 2019-05-14 2020-11-19 Unilever N.V. 2(1h)-pyridinones et leur utilisation pour traiter des états inflammatoires
US11433015B2 (en) 2019-09-10 2022-09-06 The Procter & Gamble Company Personal care compositions comprising anti-dandruff agents
US11826453B2 (en) 2019-05-14 2023-11-28 Conopco, Inc. Hair care composition comprising piroctone olamine
US11833237B2 (en) 2021-03-09 2023-12-05 The Procter & Gamble Company Method for enhancing scalp active deposition

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WO1997029733A1 (fr) * 1996-02-16 1997-08-21 Janssen Pharmaceutica N.V. Compositions contenant un antifongique et un compose soufre
EP0800814A2 (fr) * 1996-04-12 1997-10-15 Unilever Plc Compositions antimicrobiennes pour le traitement de la chevelure
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US6242007B1 (en) * 1997-04-28 2001-06-05 Arch Chemicals, Inc. Non-spherical and non-platelet forms of pyrithione salts and methods of making same
US6974569B2 (en) 1999-05-03 2005-12-13 The Procter & Gamble Company Shampoos providing a superior combination anti-dandruff efficacy and condition
US6451300B1 (en) 1999-05-03 2002-09-17 The Procter & Gamble Company Anti-dandruff and conditioning shampoos containing polyalkylene glycols and cationic polymers
US6649155B1 (en) 1999-05-03 2003-11-18 The Procter & Gamble Company Anti-dandruff and conditioning shampoos containing certain cationic polymers
WO2000066072A1 (fr) * 1999-05-03 2000-11-09 The Procter & Gamble Company Shampooing offrant une combinaison a efficacite superieure de type antipelliculaire et conditionneur
WO2002000178A1 (fr) * 2000-06-27 2002-01-03 Unilever Plc Compositions contenant une pyrithione metallique
WO2003028682A1 (fr) * 2001-10-03 2003-04-10 The Procter & Gamble Company Shampooing contenant des particules et un agent facilitant le depot
US8978666B2 (en) 2010-02-16 2015-03-17 The Procter & Gamble Company Method for providing maximum malodor and irritation control
US8685908B2 (en) 2011-02-28 2014-04-01 The Procter & Gamble Company Bar soap comprising pyrithione sources
US8980239B2 (en) 2011-10-07 2015-03-17 The Procter & Gamble Company Personal care compositions and methods of making same
US9662291B2 (en) 2011-10-07 2017-05-30 The Procter & Gamble Company Method of achieving improved hair feel
US9272164B2 (en) 2011-10-07 2016-03-01 The Procter & Gamble Company Method of achieving improved hair feel
US9504638B2 (en) 2012-05-11 2016-11-29 The Procter & Gamble Company Personal cleansing compositions comprising zinc pyrithione
US9655831B2 (en) 2013-03-14 2017-05-23 The Procter & Gamble Company Bar soap compositions containing zinc pyrithione and a metal-pyridine oxide complex
US9333157B2 (en) 2013-03-14 2016-05-10 The Procter & Gamble Company Bar soap compositions containing zinc pyrithione and a metal-pyridine oxide complex
US9375389B2 (en) 2013-04-18 2016-06-28 The Procter & Gamble Company Personal care compositions containing zinc pyrithione and a metal-phosphonate complex
US10532013B2 (en) 2013-05-22 2020-01-14 The Procter And Gamble Company Method of achieving improved product rheology, cosmetic consumer acceptance and deposition
WO2015134646A1 (fr) * 2014-03-07 2015-09-11 The Procter & Gamble Company Procédé de production de compositions de soins personnels comprenant un composé de zinc et/ou de la pyrithione
WO2015134645A1 (fr) * 2014-03-07 2015-09-11 The Procter & Gamble Company Compositions de soins personnels comprenant un composé de zinc et/ou de la pyrithione
US10201481B2 (en) 2014-03-07 2019-02-12 The Procter & Gamble Company Personal care compositions and methods of making same
US9901584B2 (en) 2015-05-06 2018-02-27 The Procter & Gamble Company Methods of cosmetically treating skin conditions with a cosmetic personal cleansing composition
WO2017089108A1 (fr) 2015-11-27 2017-06-01 Unilever N.V. Composition de nettoyage antimicrobienne
WO2018041544A1 (fr) 2016-08-30 2018-03-08 Unilever N.V. Composition de soins personnels
WO2018077602A1 (fr) 2016-10-27 2018-05-03 Unilever N.V. Composition de soins personnels
WO2018077958A1 (fr) 2016-10-27 2018-05-03 Unilever N.V. Composition de soins personnels comprenant des curcuminoïdes
WO2018172121A1 (fr) 2017-03-23 2018-09-27 Unilever N.V. Composition de soin capillaire
WO2018197118A1 (fr) 2017-04-26 2018-11-01 Unilever N.V. Composition de soin capillaire antipelliculaire comprenant de la pyrithione
WO2020229199A1 (fr) 2019-05-14 2020-11-19 Unilever N.V. 2(1h)-pyridinones et leur utilisation pour traiter des états inflammatoires
US11826453B2 (en) 2019-05-14 2023-11-28 Conopco, Inc. Hair care composition comprising piroctone olamine
US12215084B2 (en) 2019-05-14 2025-02-04 Conopco, Inc. 2(1H)-pyridinones and their use to treat inflammatory conditions
CN110074995A (zh) * 2019-05-21 2019-08-02 福建省轻工业研究所 一种含无患子提取液的祛屑组合物
CN110074995B (zh) * 2019-05-21 2022-04-08 福建省轻工业研究所 一种含无患子提取液的祛屑组合物
US11433015B2 (en) 2019-09-10 2022-09-06 The Procter & Gamble Company Personal care compositions comprising anti-dandruff agents
US11833237B2 (en) 2021-03-09 2023-12-05 The Procter & Gamble Company Method for enhancing scalp active deposition

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