WO2014177314A1 - Composition de coloration capillaire - Google Patents

Composition de coloration capillaire Download PDF

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Publication number
WO2014177314A1
WO2014177314A1 PCT/EP2014/054844 EP2014054844W WO2014177314A1 WO 2014177314 A1 WO2014177314 A1 WO 2014177314A1 EP 2014054844 W EP2014054844 W EP 2014054844W WO 2014177314 A1 WO2014177314 A1 WO 2014177314A1
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WIPO (PCT)
Prior art keywords
composition
hair
polyphenol
cationic
iron
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PCT/EP2014/054844
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English (en)
Inventor
Nicholas John Ainger
Stephen Norman Batchelor
Charlene Anne-Caroline FOURNIER
Anne-Sophie PELLETIER
Aurore Anabelle POLIDANO
Original Assignee
Unilever Plc
Unilever N.V.
Conopco, Inc., D/B/A Unilever
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Application filed by Unilever Plc, Unilever N.V., Conopco, Inc., D/B/A Unilever filed Critical Unilever Plc
Publication of WO2014177314A1 publication Critical patent/WO2014177314A1/fr

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    • 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
    • A61Q5/10—Preparations for permanently dyeing the hair
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/418—Amines containing nitro groups

Definitions

  • the present invention relates to kits and methods for colouring hair.
  • JP 04/164,017 discloses a system for colouring hair consisting of shampoo containing a surfactant and gallic acid, tannic acid, salicylic acid, derivatives thereof, pyrogallol, catechol or haematin as a first agent. This is used in conjunction with a second agent containing a polyvalent metal salt and a cationic surfactant.
  • WO2013/007606 discloses a kit comprising a first composition comprising a metal ion in the form of a salt and/or complex in which the metal ion is Fe(ll) Fe(lll), Cu(ll) or mixtures thereof and a second composition comprising an aminophenol compound.
  • the present system relates to ways of effectively introducing red tones into hair from the metal/polyphenol based colouring systems.
  • kits for colouring hair comprising: i) a first composition comprising an anionic surfactant and a polyphenol. ii) a second composition comprising a transition metal salt and/or complex, a cationic surfactant, and 4-hydroxypropylamino-3-nitrophenol.
  • 4-hydroxypropylamino-3-nitrophenol has a cas-No 92952-81 -3 and a Colipa number of B100.
  • the invention further relates to a method of colouring hair comprising the steps of sequentially applying to the hair the above mentioned composition
  • the first composition of the kit comprises a polyphenol.
  • the polyphenol of the invention comprises at least one benzene ring substituted with a first OH group and a second OH or OCH 3 group, preferably OH.
  • the first OH is ortho to the second OH group.
  • the OH containing ring may be fused to aromatic or non-aromatic rings.
  • Polyphenols may be found in the classes of phenolic acid, anthocyanin, anthocyanidin, flavanols, flavanones and gallates.
  • anthocyanin anthocyanidin
  • flavanols flavanones
  • gallates for example flavan-3-ols, flavan-4-ols, flavan-3,4-ols.
  • the polyphenol is not an anthraquinone, thus the polyphenol is not derived or based on henna.
  • a preferred polyphenol contains a benzene ring substituted in the: 1 position by an X group, wherein X is a carbon containing organic group, preferably selected from an ester group, COOH, chromenes and 3,4 dihydro-chromenes. 3 position by a H, OH or OCH 3 group, preferably an OH group. 4 position by an OH group. 5 position by an OH or OCH 3 group, preferably an OH group.
  • the polyphenol is an ortho-dihydroxybenzene derivative.
  • the polyphenol has a molecular weight of less than 1 ,000, more preferably less than 500.
  • the polyphenol of the invention is preferably selected from gallic acid, methyl gallate, ethyl gallate, propyl gallate or mixtures thereof, most preferably propyl gallate.
  • Methyl gallate, ethyl gallate, propyl gallate are obtainable by esterification of gallic acid.
  • the gallic acid is extracted from a natural source, preferably from hydrolysable tannins, preferably extracted from tara plants or gallnuts.
  • the polyphenols do not contain any active oxidase enzymes and have been heat treated to destroy any enzyme activity.
  • the polyphenol containing composition is preferably an aqueous polyphenol solution.
  • the polyphenol composition preferably comprises from 0.01 wt% to
  • 10.0 wt% of the first composition more preferably from 0.2 wt% to 4.0 wt %, most preferably 0.5 wt% to 2.5 wt% of polyphenol.
  • the composition is stored in an airtight container, preferably a bottle closed with an air tight cap.
  • the aqueous polyphenol solution contains water, preferably as the dominant ingredient.
  • Auxiliary ingredients may be present for example to increase the viscosity, perfume and help solubilise the polyphenol.
  • Solubilising ingredients include organic solvents and surfactants.
  • the water used to formulate all compositions has a French hardness of from 0 to 36 degrees, more preferably 0 to 24 degrees, most preferably from 0 to 2 degrees.
  • the water used to formulate all compositions contains less than 1 ppm of chlorine based bleaching agents such as chlorine dioxide or hypochlorite. Most preferably less than 50ppb.
  • compositions comprising the polyphenol are a shampoo composition.
  • Compositions of the invention are generally aqueous, i.e. they have water or an aqueous solution or a lyotropic liquid crystalline phase as their major component.
  • the composition will comprise from 50 % to 98%, preferably from 60 % to 90% water by weight based on the total weight of the composition.
  • the first composition according to the invention will comprise one or more anionic cleansing surfactants which are cosmetically acceptable and suitable for topical application to the hair.
  • anionic cleansing surfactants are the alkyi sulphates, alkyi ether sulphates, alkaryl sulphonates, alkanoyl isethionates, alkyi succinates, alkyi
  • alkyi and acyl groups generally contain from 8 to 18, preferably from 10 to 16 carbon atoms and may be unsaturated.
  • the alkyi ether sulphates, alkyi ether sulphosuccinates, alkyi ether phosphates and alkyi ether carboxylic acids and salts thereof may contain from 1 to 20 ethylene oxide or propylene oxide units per molecule.
  • Typical anionic cleansing surfactants for use in shampoo compositions of the invention include sodium oleyl succinate, ammonium lauryl sulphosuccinate, sodium lauryl sulphate, sodium lauryl ether sulphate, sodium lauryl ether sulphosuccinate, ammonium lauryl sulphate, ammonium lauryl ether sulphate, sodium dodecylbenzene sulphonate, triethanolamine dodecylbenzene sulphonate, sodium cocoyi isethionate, sodium lauryl isethionate, lauryl ether carboxylic acid and sodium N-lauryl sarcosinate.
  • Preferred anionic cleansing surfactants are sodium lauryl sulphate, sodium lauryl ether sulphate(n)EO, (where n is from 1 to 3), sodium lauryl ether sulphosuccinate(n)EO, (where n is from 1 to 3), ammonium lauryl sulphate, ammonium lauryl ether
  • sulphate(n)EO (where n is from 1 to 3), sodium cocoyi isethionate and lauryl ether carboxylic acid (n) EO (where n is from 10 to 20).
  • n is from 10 to 20.
  • Mixtures of any of the foregoing anionic cleansing surfactants may also be suitable.
  • the total amount of anionic cleansing surfactant in shampoo compositions of the invention generally ranges from 0.5 % to 45%, preferably from 1 .5 % to 35%, more preferably from 5 % to 20 % by total weight anionic cleansing surfactant based on the total weight of the composition.
  • a shampoo composition of the invention may contain further ingredients as described below to enhance performance and/or consumer acceptability.
  • the composition can include co-surfactants, to help impart aesthetic, physical or cleansing properties to the composition.
  • a co-surfactant is a nonionic surfactant, which can be included in an amount ranging from 0.5 % to 8%, preferably from 2 % to 5% by weight based on the total weight of the composition.
  • Other representative nonionic surfactants include mono- or di-alkyl alkanolamides.
  • Examples include coco mono- or di-ethanolamide and coco mono-isopropanolamide.
  • APG alkyl polyglycosides
  • APG is one which comprises an alkyl group connected (optionally via a bridging group) to a block of
  • APGs are defined by the following formula: wherein R is a branched or straight chain alkyl group which may be saturated or unsaturated and G is a saccharide group.
  • R may represent a mean alkyl chain length of from about C 5 to about C 2 o-
  • R represents a mean alkyl chain length of from about C 8 to about Ci 2 .
  • the value of R lies between about 9.5 and about 10.5.
  • G may be selected from C 5 or C 6 monosaccharide residues, and is preferably a glucoside.
  • G may be selected from the group comprising glucose, xylose, lactose, fructose, mannose and derivatives thereof.
  • G is glucose.
  • the degree of polymerisation, n may have a value of from about 1 to about 10 or more.
  • the value of n lies from about 1.1 to about 2.
  • the value of n lies from about 1.3 to about 1 .5.
  • Suitable alkyl polyglycosides for use in the invention are commercially available and include for example those materials identified as: Oramix NS10 ex Seppic; Plantaren 1200 and Plantaren 2000 ex Henkel.
  • compositions of the invention include the Ci 0 -Ci 8 N-alkyl (C r C 6 ) polyhydroxy fatty acid amides, such as the C12-C18 N-methyl glucamides, as described for example in
  • WO 92 06154 and US 5 194 639 and the N-alkoxy polyhydroxy fatty acid amides, such as C10-C18 N-(3-methoxypropyl) glucamide.
  • a preferred example of a co-surfactant is an amphoteric or zwitterionic surfactant, which can be included in an amount ranging from 0.5% to about 8%, preferably from 1 % to 4% by weight based on the total weight of the composition.
  • amphoteric or zwitterionic surfactants include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulphobetaines (sultaines), alkyl glycinates, alkyl carboxyglycinates, alkyl amphoacetates, alkyl amphopropionates,
  • Typical amphoteric and zwitterionic surfactants for use in shampoos of the invention include lauryl amine oxide, cocodimethyl sulphopropyl betaine, lauryl betaine, cocamidopropyl betaine and sodium cocoamphoacetate.
  • a particularly preferred amphoteric or zwitterionic surfactant is cocoamidopropyl betaine.
  • Zwitterionic surfactants reduce staining of the composition onto textiles.
  • amphoteric or zwitterionic surfactants may also be suitable.
  • Preferred mixtures are those of cocoamidopropyl betaine with further amphoteric or zwitterionic surfactants as described above.
  • a preferred further amphoteric or zwitterionic surfactant is sodium cocoamphoacetate.
  • the total amount of surfactant (including any co-surfactant, and/or any emulsifier) in a shampoo composition of the invention is generally from 1 % to 50%, preferably from 2 % to 40%, more preferably from 10 % to 25% by total weight surfactant based on the total weight of the composition.
  • Cationic Polymers are preferred ingredients in a shampoo composition of the invention for enhancing conditioning performance.
  • the combination of the first and second composition can cause staining on textiles, cationic polymers reduce staining on textiles, e.g. clothing and towels.
  • Suitable cationic polymers may be homopolymers which are cationically substituted or may be formed from two or more types of monomers.
  • the weight average (M w ) molecular weight of the polymers will generally be between 100,000 and 2 million daltons.
  • the polymers will have cationic nitrogen containing groups such as quaternary
  • ammonium or protonated amino groups or a mixture thereof. If the molecular weight of the polymer is too low, then the conditioning effect is poor. If too high, then there may be problems of high extensional viscosity leading to stringiness of the composition when it is poured.
  • the cationic nitrogen-containing group will generally be present as a substituent on a fraction of the total monomer units of the cationic polymer. 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, 3 rd edition.
  • the ratio of the cationic to non-cationic monomer units is selected to give polymers having a cationic charge density in the required range, which is generally from 0.2 to 3.0 meq/gm.
  • the cationic charge density of the polymer is suitably determined via the Kjeldahl method as described in the US Pharmacopoeia under chemical tests for nitrogen determination.
  • Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as (meth)acrylamide, alkyi and dialkyl (meth)acrylamides, alkyi
  • (meth)acrylate, vinyl caprolactone and vinyl pyrrolidine preferably have C1 -C7 alkyi groups, more preferably C1 -3 alkyi groups.
  • 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 quaternization.
  • the cationic polymers can comprise mixtures of monomer units derived from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers.
  • Suitable cationic polymers include, for example: cationic diallyl quaternary ammonium-containing polymers including, for example, dimethyldiallylammonium chloride homopolymer and copolymers of acrylamide and dimethyldiallylammonium chloride, referred to in the industry (CTFA) as
  • cationic polymers that can be used include cationic polysaccharide polymers, such as cationic cellulose derivatives, cationic starch derivatives, and cationic guar gum derivatives.
  • Cationic polysaccharide polymers suitable for use in compositions of the invention include monomers of the formula:
  • R is an alkylene, oxyalkylene, polyoxyalkylene, or
  • R 1 , R 2 and R 3 independently represent alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each group containing up to about 18 carbon atoms.
  • the total number of carbon atoms for each cationic moiety i.e., the sum of carbon atoms in R 1 , R 2 and R 3
  • X is an anionic counterion.
  • cationic cellulose includes the polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide, referred to in the industry (CTFA) as Polyquaternium 24. These materials are available from the Amerchol Corporation, for instance under the tradename Polymer LM-200.
  • Suitable cationic polysaccharide polymers include quaternary nitrogen-containing cellulose ethers (e.g. as described in U.S. Patent 3,962,418), and copolymers of etherified cellulose and starch (e.g. as described in U.S. Patent 3,958,581 ).
  • a particularly suitable type of cationic polysaccharide polymer that can be used is a cationic guar gum derivative, such a guar hydroxypropyltrimethylammonium chloride (commercially available from Rhodia in their JAGUAR trademark series). Examples of such materials are JAGUAR C13S, JAGUAR C14, JAGUAR C15, JAGUAR C17 and JAGUAR C16 Jaguar CHT and JAGUAR C162.
  • Mixtures of any of the above cationic polymers may be used.
  • Cationic polymer will generally be present in a shampoo composition of the invention at levels of from 0.01 % to 5%, preferably from 0.05 % to 1 %, more preferably from 0.08 % to 0.5% by total weight of cationic polymer based on the total weight of the composition.
  • an aqueous shampoo composition of the invention further comprises a suspending agent.
  • Suitable suspending agents are selected from 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 stearate, alkanolamides of fatty acids having from 16 to 22 carbon atoms and mixtures thereof.
  • Ethylene glycol distearate and polyethylene glycol 3 distearate are preferred long chain acyl derivatives, since these impart pearlescence to the composition.
  • 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 941 and Carbopol 980.
  • An example of a suitable copolymer of a carboxylic acid containing monomer and acrylic acid esters is Carbopol 1342. All Carbopol (trademark) materials are available from Lubrizol.
  • 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. Mixtures of any of the above suspending agents may be used.
  • Preferred is a mixture of cross-linked polymer of acrylic acid and crystalline long chain acyl derivative.
  • Suspending agent will generally be present in a shampoo composition of the invention at levels of from 0.1 % to 10%, preferably from 0.5 % to 6%, more preferably from 0.9 % to 4% by total weight of suspending agent based on the total weight of the composition.
  • the combination of the first and second composition can cause staining on textiles, the suspended agent can reduce staining on textiles, e.g. clothing and towels.
  • the pH of the composition comprising the polyphenol is in the range 3 to 8, most preferably 4 to 5.5.
  • the second composition of the kit comprises a transition metal.
  • the transition metal ion is selected from Cu(ll), Fe(ll) and Fe(lll), more preferably Fe(ll) and Fe(lll), most preferably Fe(ll).
  • the metal ion may be present in the form of a salt or a complex.
  • Iron and copper containing compositions of the invention preferably comprise from 0.01wt% to 5 wt% of metal;, more preferably 0.05 to 4 wt% more preferably from 0.4 to 1 wt%.
  • the level of metal ion in the formulation may be determined by quantitative elemental analysis.
  • the iron ion is preferably present as a complex with a ligand.
  • the ligand is preferably gluconate and/or lactate.
  • the ligand-metal complex may be pre-formed before addition to the shampoo for example iron (II) gluconate.
  • the ligand metal complex may be formed in the composition by the addition of an iron salt and the ligand for example, FeCI 2 and sodium lactate or tartrate.
  • the mole ratio of iron ion to ligand is from 1 :1 to 1 :4, more preferably from 1 :1.5 to 1 :2.5.
  • the iron ion is in the form of a complex that is soluble in aqueous solution at the pH of the formulation.
  • the iron ion in the form of a salt and/or complex has a solubility in demineralised water at the pH of the formulation of greater than 0.1 g/L.
  • the ability of a ligand to complex with a metal ion, M n+ may be defined by its pM" + value, wherein and the ligand concentration is 10 "5 mol/L and the total metal ion concentration is 10 "6 mol/L and [M" + ] free is the molar concentration of uncomplexed metal ions.
  • the ligand used has a lower pM" + , than gallic acid.
  • the pM" + are greater than 8 more preferably greater than 10.
  • pM n+ values are most preferably measured at pH 4 in de-mineralised water, with the chloride salt of the metal ion, most preferably ferric chloride.
  • Polyamino carboxylic acids are preferably present at weight % levels of less than 1/30 t of the main ligand, preferably they are absent from the iron or copper containing formulation.
  • a polyamino carboxylic acid is a compound containing two or more amines connected through carbon atoms to two or more carboxylic acid groups.
  • 2,2',2",2""-(Ethane-1 ,2- diyldinitrilo)tetraacetic acid is a polyamino carboxylic acid.
  • pentaacetic acid is a polyamino carboxylic acid.
  • Ethylenediamine-/V,/V-disuccinic acid is a polyamino carboxylic acid.
  • iron (III) gluconate iron (II) gluconate and iron(lll) lactate, iron(ll) lactate, most preferably iron (II) lactate.
  • the iron is in a composition which further comprises a cationic surfactant, such as a conditioner composition.
  • pH of the second composition comprising the transition metal is in the range from 3 to 9, more preferably 5.5 to 7.
  • the metal containing composition is a conditioner composition 4-Hvdroxypropylamino-3-nitrophenol
  • the kit preferably comprises from 0.01 wt% to 2.0 wt% of the total second composition of 4-hydroxypropylamino-3-nitrophenol, more preferably from 0.1 wt% to 1 .0 wt %, most preferably 0.1 wt% to 0.5 wt%.
  • the weight ratio of propyl gallate (100 g of the first composition)! to 4- Hydroxypropylamino-3-nitrophenol (1 OOg of the second composition) is greater than 1 , more preferably from 20 to 2, most preferably from 8 to 3.
  • a composition of the kit further comprises from 0.0 to 2.0 wt% of the total composition of 2-amino-6-chloro-4-nitrophenol (Colipa No B99), more preferably 0.01 to 1wt%, most preferably 0.1 to 0.5wt%.
  • 2-amino-6-chloro-4-nitrophenol is present in the second composition at the above levels. This adds warm brown tones.
  • the ratio of amino-6-chloro-4-nitrophenol to hydroxypropylamino-3-nitrophenol is from 0:1 to 2:1 .
  • the second composition is a conditioner for the treatment of hair (typically after shampooing) and subsequent rinsing.
  • it contains a cationic surfactant.
  • the second composition comprises one or more conditioning surfactants which are cosmetically acceptable and suitable for topical application to the hair.
  • Suitable conditioning surfactants include those selected from cationic surfactants, used singly or in admixture.
  • the cationic surfactants have the formula N + R 1 R 2 R 3 R 4 wherein R 1 , R 2 , R 3 and R 4 are independently (Ci to C 30 ) alkyl or benzyl.
  • R 1 , R 2 , R 3 and R 4 are independently (C 4 to C 30 ) alkyl and the other R 1 , R 2 , R 3 and R 4 group or groups are (Ci-C 6 ) alkyl or benzyl.
  • R 1 , R 2 , R 3 and R 4 are independently (C 6 to C 30 ) alkyl and the other R 1 , R 2 , R 3 and R 4 groups are (Ci-C 6 ) alkyl or benzyl groups.
  • the alkyl groups may comprise one or more ester (-OCO- or -COO-) and/or ether (-0-) linkages within the alkyl chain.
  • Alkyl groups may optionally be substituted with one or more hydroxyl groups.
  • Alkyl groups may be straight chain or branched and, for alkyl groups having 3 or more carbon atoms, cyclic.
  • the alkyl groups may be saturated or may contain one or more carbon-carbon double bonds (eg, oleyl).
  • Alkyl groups are optionally ethoxylated on the alkyl chain with one or more ethyleneoxy groups.
  • Suitable cationic surfactants for use in conditioner compositions according to the invention include cetyltrimethylammonium chloride, behenyltnmethylammonium chloride, cetylpyridinium chloride, tetramethylammonium chloride, tetraethylammonium chloride, octyltrimethylammonium chloride, dodecyltrimethylammonium chloride,
  • hexadecyltrimethylammonium chloride octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, didodecyldimethylammonium chloride, dioctadecyldimethylammonium chloride, tallowtrimethylammonium chloride, dihydrogenated tallow dimethyl ammonium chloride (eg, Arquad 2HT/75 from Akzo Nobel), cocotrimethylammonium chloride, PEG-2- oleammonium chloride and the corresponding hydroxides thereof.
  • Suitable cationic surfactants include those materials having the CTFA designations Quaternium-5, Quaternium-31 and Quaternium-18. Mixtures of any of the foregoing materials may also be suitable.
  • a particularly useful cationic surfactant for use in conditioners according to the invention is cetyltrimethylammonium chloride, available commercially, for example as GENAMIN CTAC, ex Hoechst Celanese.
  • Another particularly useful cationic surfactant for use in conditioners according to the invention is behenyltrimethylammonium chloride, available commercially, for example as GENAMIN KDMP, ex Clariant.
  • Suitable cationic surfactants for use in the invention is a combination of (i) and (ii) below:
  • R 1 is a hydrocarbyl chain having 10 or more carbon atoms
  • R 2 and R 3 are independently selected from hydrocarbyl chains of from 1 to 10 carbon atoms, and
  • n 1 to about 10; and an acid.
  • hydrocarbyl chain means an alkyl or alkenyl chain.
  • Preferred amidoamine compounds are those corresponding to formula (I) in which R 1 is a hydrocarbyl residue having from about 1 1 to about 24 carbon atoms,
  • R 2 and R 3 are each independently hydrocarbyl residues, preferably alkyl groups, having from 1 to about 4 carbon atoms, and m is an integer from 1 to about 4.
  • R 2 and R 3 are methyl or ethyl groups.
  • m is 2 or 3, i.e. an ethylene or propylene group.
  • Preferred amidoamines useful herein include stearamido-propyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine,
  • stearamidoethyldimethylamine palmitamidopropyldimethylamine, palmitamidopropyl- diethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethyl-amine, behenamidopropyldiethylmine,
  • behenamidoethyldiethyl-amine behenamidoethyldimethylamine, arachidamidopropyl- dimethylamine, arachidamidopropyldiethylamine, arachid-amidoethyldiethylamine, arachidamidoethyldimethylamine, and mixtures thereof.
  • amidoamines useful herein are stearamidopropyldimethylamine, stearamidoethyldiethylamine, and mixtures thereof.
  • amidoamines useful herein include:
  • stearamidopropyldimethylamine with tradenames LEXAMINE S-13 available from Inolex (Philadelphia Pennsylvania, USA) and AMIDOAMINE MSP available from Nikko (Tokyo, Japan), stearamidoethyldiethylamine with a tradename AMIDOAMINE S available from Nikko, behenamidopropyldimethylamine with a tradename INCROMINE BB available from Croda (North Humberside, England), and various amidoamines with tradenames SCHERCODINE series available from Scher (Clifton New Jersey, USA).
  • a protonating acid may be present.
  • Acid may be any organic or mineral acid which is capable of protonating the amidoamine in the conditioner composition.
  • Suitable acids useful herein include hydrochloric acid, acetic acid, tartaric acid, fumaric acid, lactic acid, malic acid, succinic acid, and mixtures thereof.
  • the acid is selected from the group consisting of acetic acid, tartaric acid, hydrochloric acid, fumaric acid, lactic acid and mixtures thereof.
  • the primary role of the acid is to protonate the amidoamine in the hair treatment composition thus forming a tertiary amine salt (TAS) in situ in the hair treatment composition.
  • TAS tertiary amine salt
  • the TAS in effect is a non-permanent quaternary ammonium or pseudo- quaternary ammonium cationic surfactant.
  • the acid is included in a sufficient amount to protonate more than
  • the level of cationic surfactant will generally range from 0.01 % to 10%, more preferably 0.05 % to 7.5%, most preferably 0.1 % to 5% by weight of the composition.
  • Conditioners of the invention will typically also incorporate a fatty alcohol.
  • fatty alcohols and cationic surfactants in conditioning compositions is believed to be especially advantageous, because this leads to the formation of a lamellar phase, in which the cationic surfactant is dispersed.
  • Representative fatty alcohols comprise from 8 to 22 carbon atoms, more preferably 16 to 22.
  • Fatty alcohols are typically compounds containing straight chain alkyl groups.
  • Suitable fatty alcohols include cetyl alcohol, stearyl alcohol and mixtures thereof.
  • 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 in conditioners of the invention will generally range from 0.01 % to 10%, preferably from 0.1 % to 8%, more preferably from 0.2 % to 7%, most preferably from 0.3% to 6% by weight of the composition.
  • the weight ratio of cationic surfactant to fatty alcohol is suitably from 1 :1 to 1 :10, preferably from 1 :1.5 to 1 :8, optimally from 1 :2 to 1 :5. If the weight ratio of cationic surfactant to fatty alcohol is too high, this can lead to eye irritancy from the composition. If it is too low, it can make the hair feel squeaky for some consumers.
  • the iron complex composition contains a non-ionic surfactant, most preferably an alcohol ethoxylate.
  • the alcohol ethoxylate with formula R 4 (OCH 2 CH2)pOI-l: where R 4 is an alkyl group that may be primary or secondary and contains C10-C22 carbon atoms. Most preferably R 4 is a C12-C18 primary alkyl chain, p is from 2 to 9, preferably from 2 to 5.
  • the non-ionic surfactant is present at 0.1 to 0.5wt%.
  • the pH of conditioner is in the range from 5.5 to 8, more preferably 6 to 7 at 20°C.
  • compositions of the invention may comprise further conditioning agents to optimise wet and dry conditioning benefits.
  • compositions of the invention can contain, emulsified droplets of a silicone conditioning agent, for enhancing conditioning performance.
  • Silicone conditioning agents may be present in the shampoo or conditioner.
  • Suitable silicones include polydiorganosiloxanes, in particular polydimethylsiloxanes which have the CTFA designation dimethicone. Also suitable for use compositions of the invention (particularly shampoos and conditioners) are polydimethyl siloxanes having hydroxyl end groups, which have the CTFA designation dimethiconol. Also suitable for use in compositions of the invention are silicone gums having a slight degree of cross- linking, as are described for example in WO 96/31 188.
  • the viscosity of the emulsified silicone itself (not the emulsion or the final hair conditioning composition) is typically at least 10,000 est at 25 °C the viscosity of the silicone itself is preferably at least 60,000 est, most preferably at least
  • the viscosity does not exceed 10 9 est for ease of formulation.
  • Emulsified silicones for use in the shampoo compositions of the invention will typically have an average silicone droplet size in the composition of less than 30, preferably less than 20, more preferably less than 10 ⁇ , ideally from 0.01 to 1 ⁇ . Silicone emulsions having an average silicone droplet size of ⁇ 0.15 ⁇ are generally termed microemulsions.
  • Emulsified silicones for use in the conditioner compositions of the invention will typically have a size in the composition of less than 30, preferably less than 20, more preferably less than 15.
  • the average silicone droplet is greater than 0.5 ⁇ , more preferably greater than 1 ⁇ , ideally from 2 to 8 ⁇ .
  • Silicone particle size may be measured by means of a laser light scattering technique, for example using a 2600D Particle Sizer from Malvern Instruments.
  • Suitable pre-formed emulsions include Xiameter MEM 1785 and
  • microemulsion DC2-1865 available from Dow Corning. These are emulsions
  • Cross-linked silicone gums are also available in a pre- emulsified form, which is advantageous for ease of formulation.
  • a further preferred class of silicones for inclusion in shampoos and conditioners of the invention are amino functional silicones.
  • amino functional silicone is meant a silicone containing at least one primary, secondary or tertiary amine group, or a quaternary ammonium group.
  • suitable amino functional silicones include: polysiloxanes having the CTFA designation "amodimethicone”.
  • amino functional silicones suitable for use in the invention are the aminosilicone oils DC2-8220, DC2-8166 and DC2-8566 (all ex Dow Corning).
  • Suitable quaternary silicone polymers are described in EP-A-0 530 974.
  • a preferred quaternary silicone polymer is K3474, ex Goldschmidt.
  • emulsions of amino functional silicone oils with non ionic and/or cationic surfactant are also suitable.
  • Pre-formed emulsions of amino functional silicone are also available from suppliers of silicone oils such as Dow Corning and General Electric. Specific examples include
  • DC939 Cationic Emulsion and the non-ionic emulsions DC2-7224, DC2-8467, DC2-8177 and DC2-8154 all ex Dow Corning.
  • DC2-7224, DC2-8467, DC2-8177 and DC2-8154 all ex Dow Corning.
  • the total amount of silicone is preferably from 0.01 wt% to 10 %wt of the total
  • composition more preferably from 0.1 wt% to 5 wt%, most preferably 0.5 wt% to
  • 3 wt% is a suitable level, especially for a shampoo composition.
  • a composition of the invention may contain other ingredients for enhancing performance and/or consumer acceptability.
  • Such ingredients include fragrance, dyes and pigments, pH adjusting agents, pearlescers or opacifiers, viscosity modifiers, preservatives, and natural hair nutrients such as botanicals, fruit extracts, sugar derivatives and amino acids.
  • compositions are devoid of a peroxy bleaching agent, such a H 2 0 2 .
  • compositions within the kit of the invention are typically "rinse-off" compositions to be applied to the hair and then rinsed away.
  • compositions are stored in an air tight container such as a bottle closed with an air tight cap.
  • compositions of the invention are applied to wet hair, necessitating the step of wetting the hair before application of the compositions of the invention.
  • the polyphenol is applied before the metal/complex and 4- Hydroxypropylamino-3-nitrophenol
  • the polyphenol formulation is a shampoo and the metal/complex and 4-Hydroxypropylamino-3-nitrophenol is in a conditioner formulation.
  • a method preferably comprises the step of rinsing hair between application of the compositions of the invention.
  • the level of each composition applied to the head of hair is preferably from 5g to 100g.
  • the first and second composition are dosed onto the hair in approximately equal weight amounts.
  • each composition comprising polyphenol and 4-hydroxypropylamino-3- nitrophenol or iron complex/salt remains on the hair for 5 to 600 seconds, more preferably 10 to 300 seconds.
  • the water used to wet and rinse the hair has a French hardness of from 0 to 36 degrees, more preferably 0 to 24 degrees, most preferably from 0 to 2 degrees.
  • the water used to wet and rinse the hair contains less than 1 ppm of chlorine based bleaching agents such as chlorine dioxide or hypochlorite. Most preferably less than 50ppb
  • a control shampoo was also made that did not contain dye.
  • the dye was added at the beginning of the formulation before the addition of fatty alcohol.
  • the shampoo and conditioner formulation were used to treat white Chinese hair switches. The hair was wet with water. 0.43g Shampoo per g hair was applied to the white hair and massaged into the hair for 30 seconds, the hair left for 3 minutes, then rinsed for 30 seconds and the procedure repeated. 0.43g per g hair of the conditioner formulation was then applied and massaged into the hair for 30 seconds, the hair left for 3 minutes, then rinsed for 30 seconds. The hair was dried and the colour measured using a reflectomer and expressed as the CIE L * a * b * values. The results are given in the table below.
  • the a * value measures the colour on the green-red axis, the more positive the value the less green (more red) the sample.
  • the change in a * and b * were expressed as:
  • Aa a(formulation with dye) - a(formulation without dye)
  • a +ve Aa indicates a redening of the switch
  • a -ve Aa value a greening of the switch.
  • Basic Red 51 introduces strong red tones (large +ve Aa) but blues the hair (-ve change in Ab). 4-hydroxypropylamino-3-nitrophenol provides red tones to the hair(+ve Aa) and counteracts the blueing of the hair (-ve Ab). It is more effective than HC Red no 7.

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Abstract

L'invention concerne un nécessaire de coloration capillaire comprenant: i) une première composition comprenant un tensioactif anionique et un polyphénol, ii) une seconde composition comprenant un sel et/ou un complexe métallique de transition, un tensioactif cationique et du 4-hydroxypropylamino-3-nitrophénol.
PCT/EP2014/054844 2013-04-29 2014-03-12 Composition de coloration capillaire WO2014177314A1 (fr)

Applications Claiming Priority (2)

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EP13165711 2013-04-29
EP13165711.6 2013-04-29

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04164017A (ja) * 1990-10-29 1992-06-09 Lion Corp 染毛剤組成物
JP2005179191A (ja) * 2003-12-16 2005-07-07 Hoyu Co Ltd 半永久染毛剤組成物
WO2012139948A2 (fr) * 2011-04-13 2012-10-18 Unilever Plc Composition de soin des cheveux

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04164017A (ja) * 1990-10-29 1992-06-09 Lion Corp 染毛剤組成物
JP2005179191A (ja) * 2003-12-16 2005-07-07 Hoyu Co Ltd 半永久染毛剤組成物
WO2012139948A2 (fr) * 2011-04-13 2012-10-18 Unilever Plc Composition de soin des cheveux

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 200550, Derwent World Patents Index; AN 2005-491922, XP002715172 *

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