WO2012139948A2 - Hair care composition - Google Patents

Hair care composition Download PDF

Info

Publication number
WO2012139948A2
WO2012139948A2 PCT/EP2012/056161 EP2012056161W WO2012139948A2 WO 2012139948 A2 WO2012139948 A2 WO 2012139948A2 EP 2012056161 W EP2012056161 W EP 2012056161W WO 2012139948 A2 WO2012139948 A2 WO 2012139948A2
Authority
WO
Grant status
Application
Patent type
Prior art keywords
composition
preferably
iron
hair
polyphenol
Prior art date
Application number
PCT/EP2012/056161
Other languages
French (fr)
Other versions
WO2012139948A3 (en )
Inventor
Nicholas John Ainger
Stephen Norman Batchelor
Neil Stephen Burnham
Robert George Riley
Original Assignee
Unilever Plc
Unilever N.V.
Hindustan Unilever 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

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/19Cosmetics or similar toilet preparations characterised by the composition containing inorganic ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365Hydroxycarboxylic acids; Ketocarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/58Metal complex; Coordination compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88Two- or multipart kits
    • A61K2800/884Sequential application

Abstract

A kit for colouring hair, comprising: (i) a first aqueous composition comprising iron, where the iron is present as a complex of gluconate and/or lactate; (ii) a second aqueous second composition, which comprises of a polyphenol selected from methyl gallate, ethyl gallate, propyl gallate or mixtures thereof.

Description

Hair Care Composition

The present invention relates to kits and methods for colouring hair. Background

Polyphenol compound mordanted with metal ions have been known to dye human hair for many years. EP0327345 (Beecham) discloses a hair colouring shampoo containing an Fe(ll) salt and a second component is applied which contains a metal ligand including ortho substituted phenols.

Two part colouring systems in which in one part comprises a metal salt are disclosed in WO2010/135237 (Advance Cosmetic Technologies);

WO/2007/130777, WO 2000/29036 (Henkel).

However, there remains the need for a colourant that delivers an effective level of colouring to hair.

Description of the Invention

Accordingly the present invention provides a kit for colouring hair, comprising:

(i) a first aqueous composition comprising iron, where the iron is present as a complex of gluconate and/or lactate ;

(ii) a second aqueous second composition, which comprises of a polyphenol selected from methyl gallate, ethyl gallate , propyl gallate or mixtures thereof. Also described is a method of colouring hair comprising the steps of applying to hair sequentially in any order:

(i) a first aqueous composition comprising iron, where the iron is present as a complex of gluconate and/or lactate;

(ii) an aqueous composition comprising a polyphenol selected from gallic acid, methyl gallate, ethyl gallate, propyl gallate or mixtures therof.

Detailed Description of the Invention Iron Complex

Iron containing compositions of the invention preferably comprise from 0.01wt% to 10 wt% of the total of iron composition of iron, more preferably from 0.1 wt% to 5wt% of the total composition, more preferably from 0.2 to 3 wt%.

The level of metal ion in the formulation may be determined by quantitative elemental analysis.

For the avoidance of doubt, if the formulation contains 2wt% of the complex

Figure imgf000003_0001

With molecular weight of 446.14, then it will contain 55.84/446.14*2 = 0.25wt% of Fe(ll) (2 decimal places).

The metal ion is selected from Fe(ll), Fe(lll), most preferably Fe(ll).

The metal ion is present as a complex with a ligand. The ligand is 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, FeC and sodium lactate. Preferably, 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.

Preferably, the metal ion is in the form of a complex that is soluble in aqueous solution at the pH of the formulation. Most preferably the metal 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, Mn+, may be defined by its pM"4 value, wherein

Figure imgf000004_0001
and the ligand concentration is 10"5 mol/L and the total metal ion concentration is 10"6 mol/L and [Mn+]free is the molar concentration of uncomplexed metal ions. Preferably the ligand used has a lower pMn+, than gallic acid. Preferably the pM"+are greater than 8 more preferably greater than 10. pMn+ 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 /30th of the main ligand, preferably they are absent from the shampoo. 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. Diethylene triamine pentaacetic acid is a polyamino carboxylic acid.

Ethylenediamine-/V,/V'-disuccinic acid is a polyamino carboxylic acid. Particularly preferred are iron (II) gluconate and iron(ll) lactate, most preferably iron (II) gluconate.

Preferably, the iron is in a composition which further comprises a cleansing surfactant, such as a shampoo composition.

Product form

To avoid oxidation of the metal by air it is preferred that the composition is stored in an air tight container such as a bottle closed with an air tight cap.

Polyphenol containing composition

The second composition of the kit comprises a polyphenol selected from gallic acid, methyl gallate, ethyl gallate , propyl gallate or mixtures thereof.

Methyl gallate, ethyl gallate, propyl gallate are obtainable by esterification of gallic acid. Preferably the gallic acid is extracted from a natural source, preferably from hydrolysable tannins. Preferably, the polyphenols do not contain any active oxidase enzymes and have been heat treated to destroy any enzyme activity.

The polyphenol is preferably selected from methyl gallate, ethyl gallate and propyl gallate, most preferably propyl gallate. The polyphenol containing composition is preferably an aqueous polyphenol solution. The polyphenol composition preferably comprises from preferably comprises from 0.05 wt% to 10.0 wt% of the total polyphenol composition, more preferably from 0.1 wt% to 5.0 wt %, most preferably 0.2 wt% to 3.0 wt% of polyphenol. Wherein the aqueous polyphenol solution preferably has a pH of 2 to 7 measured using a calibrated pH meter more preferably from 3 to 6.

To avoid oxidation of the polyphenols by air it is preferred that 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.

It is preferable if the polyphenol containing composition is a conditioning composition, more preferably a rinse off conditioning composition. Particularly preferred is a composition that is applied after shampooing.

If present in a conditioner composition comprising a protonating organic acid, the polyphenol is preferably present at a higher molar concentration than the protonating organic acid. In this case the protonating organic acid does not include a polyphenol.

Preferably, 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. Preferably, 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. Product Form

Compositions of the invention are typically "rinse-off" compositions to be applied to the hair and then rinsed away.

Shampoo Composition

Shampoo 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. Suitably, the composition will comprise from 50 % to 98%, preferably from 60 % to 90% water by weight based on the total weight of the composition.

Anionic Cleansing Surfactant Shampoo compositions according to the invention will generally comprise one or more anionic cleansing surfactants which are cosmetically acceptable and suitable for topical application to the hair.

Examples of suitable anionic cleansing surfactants are the alkyl sulphates, alkyl ether sulphates, alkaryl sulphonates, alkanoyl isethionates, alkyl succinates, alkyl sulphosuccinates, alkyl ether sulphosuccinates, N-alkyl sarcosinates, alkyl phosphates, alkyl ether phosphates, and alkyl ether carboxylic acids and salts thereof, especially sodium, magnesium, ammonium and mono- di- and

triethanolamine salts. The alkyl and acyl groups generally contain from 8 to 18, preferably from 10 to 16 carbon atoms and may be unsaturated. The alkyl ether sulphates, alkyl ether sulphosuccinates, alkyl ether phosphates and alkyl 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). 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.

Further Ingredients Optionally, a shampoo composition of the invention may contain further ingredients as described below to enhance performance and/or consumer acceptability. Co-surfactant

The composition can include co-surfactants, to help impart aesthetic, physical or cleansing properties to the composition.

An example of 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. For example, representative nonionic surfactants that can be included in shampoo compositions of the invention include condensation products of aliphatic (Cs - C-is) 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 groups.

Other representative nonionic surfactants include mono- or di-alkyl alkanolamides. Examples include coco mono- or di-ethanolamide and coco mono- isopropanolamide. Further nonionic surfactants which can be included in shampoo compositions of the invention are the alkyl polyglycosides (APGs). Typically, APG is one which comprises an alkyl group connected (optionally via a bridging group) to a block of one or more glycosyl groups. Preferred APGs are defined by the following formula: RO - (G)n 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 C5 to about C2o- Preferably R represents a mean alkyl chain length of from about Cs to about C12. Most preferably the value of R lies between about 9.5 and about 10.5. G may be selected from C5 or Ce monosaccharide residues, and is preferably a glucoside. G may be selected from the group comprising glucose, xylose, lactose, fructose, mannose and derivatives thereof. Preferably G is glucose.

The degree of polymerisation, n, may have a value of from about 1 to about 10 or more. Preferably, the value of n lies from about 1.1 to about 2. Most preferably 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.

Other sugar-derived nonionic surfactants which can be included in compositions of the invention include the C10-C18 N-alkyl (0ι-0β) 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.

Examples of amphoteric or zwitterionic surfactants include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulphobetaines (sultaines), alkyl glycinates, alkyl carboxyglycinates, alkyl amphoacetates, alkyl amphopropionates, alkylamphoglycinates, alkyl amidopropyl hydroxysultaines, acyl taurates and acyl glutamates, wherein the alkyl and acyl groups have from 8 to 19 carbon atoms. Typical amphoteric and zwitterionic surfactants for use in shampoos of the 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.

Mixtures of any of the foregoing 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 Cationic polymers are preferred ingredients in a shampoo composition of the invention for enhancing conditioning performance.

Suitable cationic polymers may be homopolymers which are cationically substituted or may be formed from two or more types of monomers. The weight average (Mw) 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, 3rd 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 dialkyi (meth)acrylamides, alkyi (meth)acrylate, vinyl caprolactone and vinyl pyrrolidine. The alkyi and dialkyi substituted monomers preferably have C1 -C7 alkyi groups, more preferably C1 -3 alkyi 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 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 Polyquaternium 6 and Polyquaternium 7, respectively;

- 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 U.S. Patent 4,009,256); - cationic polyacrylamides (as described in WO95/2231 1 ).

Other 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:

A-O-[R-N+(R1)(R2)(R3)X"], wherein: A is an anhydroglucose residual group, such as a starch or cellulose anhydroglucose residual. R is an alkylene, oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or combination thereof. R1, R2 and R3 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 R1, R2 and R3) is preferably about 20 or less, and X is an anionic counterion.

Another type of 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. Other 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 as 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.

Suspending Agent Preferably, 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 heteropolysacchande 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.

Conditioner Compositions

One part of the kit may be a conditioner for the treatment of hair (typically after shampooing) and subsequent rinsing. Such conditioner compositions preferably comprise the polyphenol. Such conditioner compositions will typically comprise 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. Preferably, the cationic surfactants have the formula N+R1 R2R3R4 wherein R1 , R2, R3 and R4 are independently (Ci to C30) alkyl or benzyl. Preferably, one, two or three of R1 , R2, R3 and R4 are independently (C4 to C30) alkyl and the other R1 , R2, R3 and R4 group or groups are (Ο-ι-Οβ) alkyl or benzyl. More preferably, one or two of R1 , R2, R3 and R4 are independently (Ce to C30) alkyl and the other R1 , R2, R3 and R4 groups are (Ο-ι-Οβ) alkyl or benzyl groups. Optionally, the alkyl groups may comprise one or more ester (-OCO- or - COO-) and/or ether (-O-) 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, behenyltrimethylammonium 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. Further 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. Another example of a class of suitable cationic surfactants for use in the invention, either alone or together with one or more other cationic surfactants, is a

combination of (i) and (ii) below:

(i) an amidoamine corresponding to the general formula (I):

Figure imgf000017_0001

R CO H(CH2)mN .

R3 in which R1 is a hydrocarbyl chain having 10 or more carbon atoms,

R2 and R3 are independently selected from hydrocarbyl chains of from 1 to 10 carbon atoms, and

m is an integer from 1 to about 10; and

(ii) an acid.

As used herein, the term hydrocarbyl chain means an alkyl or alkenyl chain.

Preferred amidoamine compounds are those corresponding to formula (I) in which R1 is a hydrocarbyl residue having from about 1 1 to about 24 carbon atoms, R2 and R3 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. Preferably, R2 and R3 are methyl or ethyl groups.

Preferably, 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.

Particularly preferred amidoamines useful herein are

stearamidopropyldimethylamine, stearamidoethyldiethylamine, and mixtures thereof.

Commercially available 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.

Preferably, 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. The TAS in effect is a non-permanent quaternary ammonium or pseudo-quaternary ammonium cationic surfactant.

Suitably, the acid is included in a sufficient amount to protonate more than 95 mole% (293 K) of the amidoamine present.

In conditioners of the invention, 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. The combined use of 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. Examples of 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.

Further Conditioning Agents

Compositions of the invention may comprise further conditioning agents to optimise wet and dry conditioning benefits.

The 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 500,000 est, ideally at least 1 ,000,000 est. Preferably the viscosity does not exceed 109 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 μηι , ideally from 0.01 to 1 μπΊ . Silicone emulsions having an average silicone droplet size of < 0.15 μηι 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. Preferably, the average silicone droplet is greater than 0.5 μηι , more preferably greater than 1 μηι, ideally from 2 to 8 μηι.

Silicone particle size may be measured by means of a laser light scattering technique, for example using a 2600D Particle Sizer from Malvern Instruments. Examples of suitable pre-formed emulsions include Xiameter MEM 1785 and microemulsion DC2-1865 available from Dow Corning. These are emulsions /microemulsions of dimethiconol. 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. By "amino functional silicone" is meant a silicone containing at least one primary, secondary or tertiary amine group, or a quaternary ammonium group. Examples of suitable amino functional silicones include: polysiloxanes having the CTFA designation "amodimethicone", Specific examples of 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. Also suitable are emulsions of amino functional silicone oils with non ionic and/or cationic surfactant.

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).

With some shampoos it is preferred to use a combination of amino and non amino functional silicones

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.

Other Optional Ingredients

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.

Method of use

The method of colouring hair comprising the steps of applying to hair sequentially in any order:

(i) a shampoo composition comprising at least one metal salt and/or complex in which the metal is selected from iron, copper, zinc or manganese and a surfactant mix comprising from 1 .5 wt% to 50 wt% of the total shampoo composition of a nonionic in which the nonionic surfactant is the major component by weight of the surfactant mix and

(ii) a second composition, which comprises from 0.05 wt% to 10 wt% of the total second composition of a polyphenol.

Preferably, the compositions of the invention are applied to wet hair, necessitating the step of wetting the hair before application of the compositions of the invention.

A method preferably comprises the step of rinsing hair between application of the shampoo composition (i)and the second composition (ii). It is highly preferred if the hair is rinsed after application of both compositions of the invention.

Further conditioning and/or styling products may be applied as part of the colouring process.

The level of each composition applied to the head of hair is preferably from 5g to 100g.

Preferably, each composition remains on the hair for 5 to 600 seconds, more preferably 10 to 300 seconds.

Preferably, 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.

Preferably, 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 The invention will now be illustrated by the following non-limiting examples. Examples of the invention are illustrated by a number comparative examples are illustrated by a letter Examples

Reference Example A

The following reference formulations of WO2010/135237 was made Natural Black 1 N activator

Figure imgf000024_0001

2g of the Natural Black 1 N activator was rubbed into a 0.7g bleached blonde human switch and left for 10 minutes. 2g of the Natural Black 1 N colour was then rubbed into the hair and left for a further 20 minutes. The switch was then rinsed for 1 minutes in running demineralised water, dried and the colour measured using a reflectometer and expressed as the CIE L*a*b* values. ΔΕ value were calculated with respected to an untreated control. Larger ΔΕ values indicate a greater colouration of the hair.

The experiment was repeated with the exclusion of Indigo from the Natural Black 1 N colour The results are given in the table below

Figure imgf000025_0001

The total weight of polyphenol (logwood extract) applied to the hair is 0.4g.

The total weight of iron applied to the hair is 0.030g

Example 1

0.7 g of a bleached blonde hair switch was bathed in 3g of a formulation containing 0.5wt% FeS04 and 2wt% of sodium gluconate for 5 minutes. The switch was rinsed and then bathed in 3ml of a formulation contain 0.5wt% of a polyphenol for 5 minutes. The switch was rinsed, dried the colour measured using a reflectometer and expressed as the CIE L*a*b* values. ΔΕ value were calculated with respected to an untreated control. The results are given in the table below

Figure imgf000026_0001

The total weight of polyphenol applied to the hair is 0.01

The total weight of iron applied to the hair is 0.0055g.

This is much less than the reference example.

The compounds provide a great colour change in the hair than the reference formulation of example A.

Example 2

3, 0.7g white human hair switches were soaked in 45 ml of distilled water containing 2wt% of iron gluconate for 5 minutes. The switches were removed and rinsed with distilled water for 30 seconds before being soaked in a 45 ml solution containing 0.2wt% of tannic acid for 5 minutes (Example B). . The switches were removed and rinsed with distilled water for 30 seconds, then dried in air. The experiment was repeated, except the tannic acid was replaced by propyl gallate (Example 2).

Once dried the colour of the switches was measured using a reflectometer and expressed as the CIE L*a*b* values. The results are summarised in the table below L*

Control (no treatment) 71 .2

Tannic acid (reference)Example B 56.8

Propyl Gallate Example 2 34.9

The propyl gallate provides the greatest colouration to the hair, as indicated by the lowest L* value.

Claims

1 . A kit for colouring hair, comprising:
(i) a first aqueous composition comprising iron, where the iron is present as a complex of gluconate and/or lactate ;
(ii) a second aqueous second composition, which comprises of a polyphenol selected from methyl gallate, ethyl gallate , propyl gallate or mixtures thereof.
2. A kit according to claim 1 in which the iron is Fe(ll).
3. A kit as claimed in any preceding claim in which iron is present as iron (II) gluconate.
4. A kit according to any preceding claim in which the level of polyphenol is from 0.1 wt% to 5.0wt% of the total second composition
5. A kit according to claim 4 in which the level of polyphenol is from 0.2 wt% to 3.0wt% of the total second composition,
6. A kit according to any preceding claim in which the level of iron is from
0.01 wt% to 5.0wt% of the total first composition.
7. A kit for colouring hair according to any preceding claim in which the iron containing composition further comprises a cleansing surfactant.
8. A kit for colouring hair according to any preceding claim in which the
polyphenol is present in a conditioning composition.
9. A kit for colouring hair according to claim 8 in which the polyphenol comprising composition further comprises a cationic surfactant
10. A method of colouring hair comprising the steps of applying to hair
sequentially in any order:
(i) an aqueous composition comprising iron, where the iron is present as a complex of gluconate and/or lactate ;
(ii) an aqueous composition comprising a polyphenol selected from gallic acid, methyl gallate, ethyl gallate , propyl gallate or mixtures therof.
1 1 . A method according to claim 10 which further comprises the step of rinsing the hair between application of the compositions.
PCT/EP2012/056161 2011-04-13 2012-04-04 Hair care composition WO2012139948A3 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP11162205 2011-04-13
EP11162205.6 2011-04-13

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN 201280017908 CN103458860A (en) 2011-04-13 2012-04-04 Hair care composition
EP20120711674 EP2696840A2 (en) 2011-04-13 2012-04-04 Hair care composition

Publications (2)

Publication Number Publication Date
WO2012139948A2 true true WO2012139948A2 (en) 2012-10-18
WO2012139948A3 true WO2012139948A3 (en) 2013-07-11

Family

ID=44583534

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/056161 WO2012139948A3 (en) 2011-04-13 2012-04-04 Hair care composition

Country Status (3)

Country Link
EP (1) EP2696840A2 (en)
CN (1) CN103458860A (en)
WO (1) WO2012139948A3 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2799115A1 (en) * 2013-05-03 2014-11-05 Unilever PLC Hair care composition
WO2014177315A1 (en) * 2013-04-29 2014-11-06 Unilever Plc Hair colouring composition
WO2014177314A1 (en) * 2013-04-29 2014-11-06 Unilever Plc Hair colouring composition

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3958581A (en) 1972-05-17 1976-05-25 L'oreal Cosmetic composition containing a cationic polymer and divalent metal salt for strengthening the hair
US3962418A (en) 1972-12-11 1976-06-08 The Procter & Gamble Company Mild thickened shampoo compositions with conditioning properties
US4009256A (en) 1973-11-19 1977-02-22 National Starch And Chemical Corporation Novel shampoo composition containing a water-soluble cationic polymer
EP0327345A2 (en) 1988-02-04 1989-08-09 Wella Aktiengesellschaft Hair darkening compositions
WO1992006154A1 (en) 1990-09-28 1992-04-16 The Procter & Gamble Company Polyhydroxy fatty acid amide surfactants to enhance enzyme performance
EP0530974A1 (en) 1991-08-05 1993-03-10 Unilever Plc Hair care composition
US5194639A (en) 1990-09-28 1993-03-16 The Procter & Gamble Company Preparation of polyhydroxy fatty acid amides in the presence of solvents
WO1995022311A1 (en) 1994-02-18 1995-08-24 Unilever Plc Personal washing compositions
WO1996031188A1 (en) 1995-04-06 1996-10-10 Unilever Plc Hair treatment compositions
WO2000029036A2 (en) 1998-11-17 2000-05-25 Henkel Kommanditgesellschaft Auf Aktien Colorants with transition metal complexes
WO2007130777A2 (en) 2006-05-01 2007-11-15 Advanced Cosmetic Technologies Llc Composition for dyeing keratin fibers and a method of dyeing hair using same
WO2010135237A1 (en) 2009-05-18 2010-11-25 Advanced Cosmetic Technologies, Llc Composition for dyeing keratin fibers and a method of dyeing hair using same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5196029A (en) * 1989-04-24 1993-03-23 Kao Corporation Hair-treatment composition, bleaching composition and hair color tone modifier composition
JP2006348011A (en) * 2005-06-17 2006-12-28 Estate Chemical Kk Hair dye
JP5548382B2 (en) * 2009-04-14 2014-07-16 資生ケミカル株式会社 Hair dyeing method
CN101926739A (en) * 2009-06-24 2010-12-29 浙江养生堂天然药物研究所有限公司 Hair dye, hair dying product unit and use method thereof

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3958581A (en) 1972-05-17 1976-05-25 L'oreal Cosmetic composition containing a cationic polymer and divalent metal salt for strengthening the hair
US3962418A (en) 1972-12-11 1976-06-08 The Procter & Gamble Company Mild thickened shampoo compositions with conditioning properties
US4009256A (en) 1973-11-19 1977-02-22 National Starch And Chemical Corporation Novel shampoo composition containing a water-soluble cationic polymer
EP0327345A2 (en) 1988-02-04 1989-08-09 Wella Aktiengesellschaft Hair darkening compositions
WO1992006154A1 (en) 1990-09-28 1992-04-16 The Procter & Gamble Company Polyhydroxy fatty acid amide surfactants to enhance enzyme performance
US5194639A (en) 1990-09-28 1993-03-16 The Procter & Gamble Company Preparation of polyhydroxy fatty acid amides in the presence of solvents
EP0530974A1 (en) 1991-08-05 1993-03-10 Unilever Plc Hair care composition
WO1995022311A1 (en) 1994-02-18 1995-08-24 Unilever Plc Personal washing compositions
WO1996031188A1 (en) 1995-04-06 1996-10-10 Unilever Plc Hair treatment compositions
WO2000029036A2 (en) 1998-11-17 2000-05-25 Henkel Kommanditgesellschaft Auf Aktien Colorants with transition metal complexes
WO2007130777A2 (en) 2006-05-01 2007-11-15 Advanced Cosmetic Technologies Llc Composition for dyeing keratin fibers and a method of dyeing hair using same
WO2010135237A1 (en) 2009-05-18 2010-11-25 Advanced Cosmetic Technologies, Llc Composition for dyeing keratin fibers and a method of dyeing hair using same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014177315A1 (en) * 2013-04-29 2014-11-06 Unilever Plc Hair colouring composition
WO2014177314A1 (en) * 2013-04-29 2014-11-06 Unilever Plc Hair colouring composition
EP2799115A1 (en) * 2013-05-03 2014-11-05 Unilever PLC Hair care composition

Also Published As

Publication number Publication date Type
WO2012139948A3 (en) 2013-07-11 application
EP2696840A2 (en) 2014-02-19 application
CN103458860A (en) 2013-12-18 application

Similar Documents

Publication Publication Date Title
US6432420B2 (en) Hair treatment compositions
WO2004006876A1 (en) Hair and/or scalp treatment composition
WO2007068401A1 (en) Hair treatment compositions
WO2010052092A1 (en) Conditioning shampoo composition comprising an aqueous conditioning- gel
WO2001030310A1 (en) Hair treatment compositions comprising particulate substances
US6551361B1 (en) Method of hair treatment using organic amino compounds
US20050112074A1 (en) Hair treatment composition comprising composite particles of clay and charged organic molecule
US6440439B1 (en) Hair treatment compositions
WO2004054526A1 (en) Hair treatment compositions
WO1999029286A1 (en) Hair treatment composition
WO2002074266A2 (en) Method and composition for the gradual permanent coloring of hair
US20080317695A1 (en) Hair Care Compositions
US20120093757A1 (en) Composition
WO2002102334A2 (en) Hair treatment composition
WO2010052093A1 (en) Conditioning shampoo comprising an aqueous conditioning gel phase in the form of vesicles
US20020071819A1 (en) Shampoo compositions
US20080038215A1 (en) Hair Care Composition Comprising a Dendritic Macromolecule
EP1652555A1 (en) Hair care compositions
WO2011003554A2 (en) Method for levelling hair colour
US6509011B1 (en) Method of hair treatment using organic amino compounds
WO2006097193A1 (en) Hair and/or scalp care compositions incorporating amino-oxo-indole-ylidene compounds
EP1366754A1 (en) Composition for the dyeing of human hair
WO1999059530A1 (en) Hair treatment composition containing particles of macroporous, highly cross-linked polymer
EP2272493A1 (en) Composition and method for levelling hair colour
EP1504748A1 (en) Hair conditioning composition

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12711674

Country of ref document: EP

Kind code of ref document: A2

DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112013026131

Country of ref document: BR

ENP Entry into the national phase in:

Ref document number: 112013026131

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20131010