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WO1997039096A1 - Composition antimicrobienne pour traitement capillaire - Google Patents

Composition antimicrobienne pour traitement capillaire Download PDF

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Publication number
WO1997039096A1
WO1997039096A1 PCT/US1997/006232 US9706232W WO9739096A1 WO 1997039096 A1 WO1997039096 A1 WO 1997039096A1 US 9706232 W US9706232 W US 9706232W WO 9739096 A1 WO9739096 A1 WO 9739096A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
hair treatment
antimicrobial
treatment composition
compound
Prior art date
Application number
PCT/US1997/006232
Other languages
English (en)
Inventor
Peter C. Konidaris
Jonathan D. Hague
Original Assignee
Olin Corporation
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 Olin Corporation filed Critical Olin Corporation
Priority to AU24601/97A priority Critical patent/AU2460197A/en
Publication of WO1997039096A1 publication Critical patent/WO1997039096A1/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
    • A61K8/18—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
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • This invention relates to a hair treatment composition, and particularly to a hair treatment composition containing an antimicrobial agent and which is transparent.
  • Hair treatment compositions are often desired to be transparent, i.e. optically clear or substantially clear. This is not only of benefit as regards visual product appeal to the consumer, but also conveys a perception of "lightness", which is particularly important for people whose hair is naturally greasy, for whom overconditioning associated with conventional opaque formulations can lead to dullness and a heavy, coated feel.
  • Insoluble particulate metal pyrithiones are the predominant antimicrobial agents encountered in antimicrobial compositions, such as antidandruff hair shampoos and conditioners.
  • the zinc salt hereinafter referred to as ZnPTO
  • ZnPTO zinc salt
  • a problem is that the insolubility of ZnPTO renders it unsuitable for transparent formulations.
  • dispersed particles of the ZnPTO are suspended in the composition.
  • thickeners or bulking agents, such as clays and pearlescers frequently have to be added to give structural viscosity to the system and prevent ZnPTO separation and settlement during storage. Such additives cloud the product further and lead to aesthetic unacceptability.
  • a particular problem with ZnPTO containing formulations is chalkiness.
  • W095/11233 describes a specific class of 1- hydroxy-6-substituted pyridine-2-ones and 2-thiones, a process for their preparation and their use as antimicrobials in industrial and cosmetic applications generally ranging from soaps and shampoos to sealants and other polymer compositions, most especially paints.
  • the compounds are stated to be soluble in water and organic solvents.
  • the present invention provides an antimicrobial hair treatment composition comprising the following components: [a) an antimicrobial compound of the formula:
  • X is an oxygen or sulphur moiety and R is a substituted or unsubstituted hydrocarbon radical having between l and 20 carbon atoms, with the proviso that R is other than chlorobenzyl, and R 1 is hydrogen or a cation selected from the group consisting of alkali metals, alkaline earth metals, ammonium ion and organic ammonium ions, or a compound of the formula:
  • Y is an oxygen, sulphur, or NR 11 moiety wherein N is nitrogen and R and R 11 are independently each a substituted or unsubstituted hydrocarbon radical having between 1 and 20 carbon atoms, or a compound of the formula:
  • R 111 and R IV are independently either hydrogen or a substituted or unsubstituted hydrocarbon radical having between 1 and 20 carbon atoms, with the proviso that either R or R" is a hydrocarbon radical;
  • Preferred hydrocarbon radicals for the R group in the above formulae (I) , (II) , and (III) are aliphatic hydrocarbons having between 3 and 15 carbons, more preferably a straight chain hydrocarbon having between 5 and 10 carbons.
  • substituted hydrocarbon is intended to include substituents such as halogen, chloro, iodo, fluoro or bromo, alkoxy such as methoxy, ethoxy, propoxy or butoxy, nitro, thio, amino combinations thereof, and the like.
  • Illustrative hydrocarbon groups include an-octyl, 2,4,4-trimethylpentyl, 3,5,5-trimethylhexyl, combinations thereof, and the like.
  • R 1 examples include sodium, lithium, potassium, calcium, magnesium, ammonium, and mono-, di-, or tri-ethanolamine.
  • the amount of antimicrobial compound 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 antimicrobial compound is from about 0.001 to about 5% by weight of the total composition, more preferably from about 0.1 to about 3% by weight.
  • the composition according to the invention 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 one to 10 ethylene oxide or propylene oxide units per molecule, and preferably contain 2 to 3 etheylene oxide units per molecule.
  • suitable 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 1EO, 2EO and 3EO.
  • Nonionic surfactants suitable for use in composition of the invention may include condensation products of aliphatic (C 8 -C 18 ) primary or secondary linear or branched chain alcohols or phenols with alkylene oxides, usually ethylene oxide and generally having from 6 to 30 ethylene oxide group.
  • Other suitable nonionics include mono- or di-alkyl alkanolamides. Examples include coco mono- or di-ethanolamide and coco monoisopropanolamide.
  • Amphoteric and zwitterionic surfactants suitable for use in compositions of the invention may include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl ⁇ ulphobetaines (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, 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.
  • the use of 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
  • 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, as are well known in the art.
  • the conditioning agents may include silicones, protein hydrolyzates, 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 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. Particularly preferred are silicone microemulsions, in view of their transparency.
  • a silicone with a viscosity in the range of 1-20 million cst is used.
  • the silicone is preferably emulsion-polymerised, since this enables silicones of very high viscosity to be more easily processed.
  • the silicone can be cross-linked.
  • Suitable protein hydrolysates include lauryl dimonium hydroxy propylamino hydrolysed animal protein, available commercially under the trade name LAMEQUAT L, and hydrolysed keratin containing sulphur-bearing amino acids, available commercially under the trade name CROQUAT WKP.
  • the hair treatment composition may also contain a polymeric water-soluble deposition aid for the antimicrobial compound.
  • deposition aid is meant an agent which enhances deposition of the antimicrobial compound 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 0.5 to 1%, more preferably from about 0.08% to about 0.5% by weight.
  • the deposition aid may be a homopolymer or be formed from two or more types of monomers.
  • the molecular weight of the polymer will generally beween 5 000 and 20 000 000, typically at least 10 000 and preferably in the range 100 000 to about 10 000 000.
  • the polymers will have cationic nitrogen containing groups such as quaternary ammonium or protonated amino groups, or a mixture thereof.
  • the cationic charge density of the deposition aid which is defined as the reciprocal of the molecular weight of a monomeric unit of the polymer containing 1 charge, has been found to need to be 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 be at least 7 and preferably between .5 and 9.5.
  • the cationic nitrogen-containing group will generally be present as a substituent on a fraction of the total monomer units of the deposition aid. Thus when 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 the cationic to non-cationic monomer units is selected to give a polymer having a cationic charge density in the required range.
  • Suitable cationic deposition aids include, for example, copolymers "of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as (meth)acrylamide, alkyl and dialkyl
  • (meth)acrylamides alkyl (meth)acrylate, vinyl caprolactone and vinyl pyrrolidine.
  • the alkyl and dialkyl substituted monomers preferably have C1-C7 alkyl groups, more preferably Cl-3 alkyl groups.
  • Other suitable spacers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol and ethylene glycol.
  • the cationic amines can be primary, secondary or tertiary amines, depending upon the particular species and the pH of the composition. In general secondary and tertiary amines, especially tertiary, are preferred.
  • Amine substituted vinyl monomers and amines can be polymerized in the amine form and then converted to ammonium by quatemization.
  • Suitable cationic amino and quaternary ammonium monomers include, for example, vinyl compounds substituted with dialkyl aminoalkyl acrylate, dialkylamino alkylmethacrylate, monoalkylaminoalkyl acrylate, monoalkylaminoalkyl methacrylate, trialkyl methacryloxyalkyl ammonium salt, trialkyl acryloxyalkyl ammonium salt, diallyl quaternary ammonium salts, and vinyl quaternary ammonium monomers having cyclic cationic nitrogen- containing rings such as pyridinium, imidazolium, and quaternized pyrrolidine, e.g., alkyl vinyl imidazolium, alkyl vinyl pyridinium, and alkyl vinyl pyrrolidine salts.
  • the alkyl portions of these monomers are preferably lower alkyls such as the C ⁇ alkyls, more preferably C x and C 2 alkyls.
  • Suitable amine-substituted vinyl monomers for use herein include dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, dialkylaminoalkyl acrylamide, and dialkylaminoalkyl methacrylamide, wherein the alkyl groups are preferably Ci-C, hydrocarbyls, more preferably Ci-Cj, alkyls.
  • the deposition aid can comprise mixtures of monomer units derived from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers.
  • Suitable deposition aids include, for example: cationic copolymers of l-vinyl-2-pyrrolidine and 1- vinyl-3-methyl-imidazolium salt (e.g., Chloride salt) (referred to in the industry by the Cosmetic, Toiletry, and Fragrance Association, "CTFA", as Polyquaternium-16) ; copolymers of 1-vinyl-2- pyrrolidine and dimethylaminoethyl methacrylate (referred to in the industry by CTFA as Polyquaternium-11) ,- cationic diallyl quaternary ammonium-containing polymers including, for example, dimethyldiallylammonium chloride homopolymer (referred to in the industry (CTFA) as Polyquatenium 6) ; mineral acid salts of amino-alkyl esters of homo-and co-polymers of unsaturated carboxylic acids having from 3 to 5 carbon atoms, as described in
  • cationic deposition aids that can be used include cationic guar gum derivatives, such as guar hydroxypropyltrimonium chloride (Commerically available from Celanese Corp. in their Jaguar trademark series) .
  • Examples 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 as well as cationic quaternary ammonium groups, and JAGUAR 162 which is a high transparency, medium viscosity guar having a low degree of substitution.
  • the deposition aid is selected from the group comprising cationic polyacrylamides, and cationic guar derivatives. Particularly preferred deposition aids are Jaguar C13S with a cationic charge density of 0.8 meq/g. Other particularly suitable materials include Jaguar C15, Jaguar C17 and Jaguar C16 and Jaguar C162.
  • 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 are a particularly preferred product form for compositions of the invention.
  • additional ingredients conventionally incorporated into hair treatment formulations may be included in the compositions of the invention.
  • additional ingredients include polymer lattices, additional antimicrobial agents such as ZnPTO and Octopirox, foam boosters, perfumes, colouring agents, preservatives, viscosity modifiers, proteins, polymers, buffering or pH adjusting agents, moisturizing agents, herb or other plant extracts and other natural ingredients.
  • a method of preparing an antimicrobial hair treatment composition which method comprises mixing together the components (a) , (b) and (c) as are defined above, and adjusting the pH of the resultant composition to at least 7, so that the antimicrobial compound of component (a) is soluble in the final hair treatment composition.
  • Formulations of the present invention have the advantage that thickeners of suspending agents, which can adversely affect optical clarity, are not required for the antimicrobial compound. In this way optical clarity of the final formulation may be preserved, without comprising product stability.
  • An antimicrobial shampoo composition was made up from the following ingredients:
  • the pH of the composition was adjusted to 8.0 so that the HP101 was present in soluble form.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention se rapporte à une composition antimicrobienne pour traitement capillaire qui est une composition de shampooing. Cette composition comporte un composé antimicrobien sélectionné parmi certains composés pyridine-2-one et 2-thione à substitution 1-hydroxy-6 ainsi qu'un agent tensioactif de shampooing, le pH de ladite composition pour traitement capillaire étant ajusté à une valeur au moins égale à 7. De cette manière, il est possible de maintenir la solubilité de l'agent actif antimicrobien et donc la limpidité optique de la formulation finale, ce qui rend possible la fabrication de formulations transparentes.
PCT/US1997/006232 1996-04-12 1997-04-10 Composition antimicrobienne pour traitement capillaire WO1997039096A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU24601/97A AU2460197A (en) 1996-04-12 1997-04-10 Antimicrobial hair treatment composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9607569 1996-04-12
GB9607569A GB2311995B (en) 1996-04-12 1996-04-12 Antimicrobial hair treatment composition

Publications (1)

Publication Number Publication Date
WO1997039096A1 true WO1997039096A1 (fr) 1997-10-23

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PCT/US1997/006232 WO1997039096A1 (fr) 1996-04-12 1997-04-10 Composition antimicrobienne pour traitement capillaire

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AU (1) AU2460197A (fr)
GB (1) GB2311995B (fr)
WO (1) WO1997039096A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9813640D0 (en) * 1998-06-24 1998-08-26 Unilever Plc Antimicrobial hair treatment composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4185106A (en) * 1972-07-11 1980-01-22 Hoechst Aktiengesellschaft Pyridones as antidandruff agents
US4711775A (en) * 1972-07-11 1987-12-08 Hoechst Aktiengesellschaft Cosmetic compositions
US4916228A (en) * 1986-08-02 1990-04-10 Hoechst Aktiengesellschaft Process for the preparation of 1-hydroxy-2-pyridones
WO1995011233A1 (fr) * 1993-10-18 1995-04-27 Olin Corporation Pyridine-2-ones substituees et pyridine-2-thiones substituees utilisees en tant que biocides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4185106A (en) * 1972-07-11 1980-01-22 Hoechst Aktiengesellschaft Pyridones as antidandruff agents
US4711775A (en) * 1972-07-11 1987-12-08 Hoechst Aktiengesellschaft Cosmetic compositions
US4916228A (en) * 1986-08-02 1990-04-10 Hoechst Aktiengesellschaft Process for the preparation of 1-hydroxy-2-pyridones
WO1995011233A1 (fr) * 1993-10-18 1995-04-27 Olin Corporation Pyridine-2-ones substituees et pyridine-2-thiones substituees utilisees en tant que biocides

Also Published As

Publication number Publication date
GB2311995B (en) 1999-12-15
AU2460197A (en) 1997-11-07
GB9607569D0 (en) 1996-06-12
GB2311995A (en) 1997-10-15

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