WO2003009822A2 - Compositions pour coloration capillaire et leur utilisation - Google Patents

Compositions pour coloration capillaire et leur utilisation Download PDF

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Publication number
WO2003009822A2
WO2003009822A2 PCT/US2002/023196 US0223196W WO03009822A2 WO 2003009822 A2 WO2003009822 A2 WO 2003009822A2 US 0223196 W US0223196 W US 0223196W WO 03009822 A2 WO03009822 A2 WO 03009822A2
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WO
WIPO (PCT)
Prior art keywords
hair
developer
coupler
oxidised
electrophilic attack
Prior art date
Application number
PCT/US2002/023196
Other languages
English (en)
Other versions
WO2003009822A3 (fr
Inventor
James Charles Dunbar
Delyth Angharad James
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP2003515215A priority Critical patent/JP2004537560A/ja
Priority to MXPA04000470A priority patent/MXPA04000470A/es
Priority to EP02756569A priority patent/EP1408918A2/fr
Publication of WO2003009822A2 publication Critical patent/WO2003009822A2/fr
Publication of WO2003009822A3 publication Critical patent/WO2003009822A3/fr
Priority to US10/764,191 priority patent/US7066967B2/en

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Classifications

    • 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
    • A61K8/30—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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A61K8/415—Aminophenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil

Definitions

  • This invention relates to new compositons for colouring hair and to methods of using the compositions in hair colouring processes. In particular it relates to new combinations of developer components and their use for achieving particular effects.
  • Hair colouring compositions generally comprise various aromatic compounds, commonly known as developers (also known as precursors or primary intermediates) , together with various other compounds, commonly known as couplers. These are referred to as oxidative hair colouring agents because they require an oxidising agent for formation of colour.
  • developers also known as precursors or primary intermediates
  • couplers These are referred to as oxidative hair colouring agents because they require an oxidising agent for formation of colour.
  • the compounds described as developers are those which react with oxidising agent to form a reactive oxidised intermediate. This intermediate then reacts with the coupler or couplers to give a coloured molecule.
  • Some developers are capable of reacting with another molecule of the same type, ie self-coupling. Couplers do not generally react with oxidising agent but instead react with the reactive oxidised intermediate formed by reaction between the developer and the oxidising agent.
  • EP-A-079, 540 which discloses 2 , 6-dichloro-para- aminophenol as developer in combination with various couplers, but no further developers
  • EP-A-951, 900 which includes 2, 6-dichloro-para-aminophenol as an essential component and exemplifies it together with various couplers and other single electrophilic attack developers.
  • compositions containing single electrophilic attack developers give benefits in terms of accuracy of prediction of final colour, they can exhibit problems with evenness of colouration.
  • the condition of the root hair is often different from the condition of the hair at the tip.
  • At least one developer selected from amino aromatic systems capable of being oxidised and thereafter undergoing at least two electrophilic attack reactions, and (iii) at least one coupler.
  • the invention also provides the use of a composition comprising (i) single electrophilic attack developer and (ii) multiple electrophilic attack developer and (iii) coupler to improve the root-to-tip evenness of colour applied to hair.
  • a hair colouring composition comprising single electrophilic attack developer and coupler.
  • the compositions of the invention may be used in a method of colouring hair.
  • the invention also provides a kit comprising a separately packaged colouring component containing single electrophilic attack developer and multiple electrophilic attack developer and coupler and a separately packaged oxidising component, which may be used to provide compositions for colouring hair.
  • Developers are those components of the composition which react with the oxidising agent to form a reactive intermediate which then goes on to react with the couplers.
  • the first developer is capable of being oxidised and thereafter undergoing only a single electrophilic attack.
  • the substituents is selected from para- and ortho- disubstituted benzene compounds, wherein one of the substituents is a primary amine group and the other substituent is a different group, preferably selected from nitro, hydroxyl or disubstituted amine.
  • it is selected from substituted and unsubstituted paraaminophenols .
  • Paraaminophenol itself may be used, as may be dihaloparaaminophenols, where halo can be chloro or bromo. In particular especially good results are given by 2 , 6-dichloroparaaminophenol .
  • the composition also contains a multiple electrophilic attack developer.
  • This may be selected from para- and ortho-disubsituted benzene compounds, disubstituted pyridine compounds, disubstituted pyrimidines and diamino substituted pyrazoles .
  • Diamino benzenes and diaminopyrazoles for example 1- (2 hydroxyethyl) -4 , S-diaminopyrazole are preferred. We observe particularly good improvements in root-to- tip evenness with paraphenylenediamine.
  • Suitable amounts of total developer are from 0.01 to 5 or 7 wt.% based on total composition applied to the hair. Preferred amounts are from 0.3 to 2 or 4%, preferably 0.4 to 1.5 or 3%.
  • the ratio of single electrophilic attack developer to multiple electrophilic attack developer can be for instance from 5:95 to 95:5, in particular 20:80 to 80:20, preferably 60:40 to 40:60.
  • the composition also comprises a coupler.
  • a coupler reacts with the reactive intermediate formed by oxidation of the developer. Generally it does not itself react with the oxidising agent under the conditions used in the hair colouring process.
  • the couplers may be of the types discussed in W098/52522.
  • couplers which give a cyan colour reaction with the developers may be selected from compounds of the formula I :
  • Z is H or another active leaving group.
  • Z is H.
  • R 1 , R 2 , R 3 and R 4 are, independently, H, OH, -CH 2 H, - C0 2 R, F, Cl, Br, -CN, -N0 2 -, CF 3 , cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl, aralkyl, -NH2, -NHR, -NHCOR, - NR 2 , -NHCOR, -R'NHCOR, -CONHR, R'CONHR, -R'OH, -S0 2 R, S0 2 NHR, -R'S0 2 R, -R'S0 2 R, -R'S0 2 NHR, -S0 3 H, -OR, -R'OR or -COR, in any of which R is H, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl or aralkyl, and
  • R 1 and R 2 may together form a substituted or unsubstituted cycloalkyl, cycloalkenyl or aryl group.
  • Substituting groups include OH, -OR, Cl, Br, F, -C0 2 H, -C0 2 R, -NH 2 and -COR.
  • the active leaving group Z is any group which can be removed under the conditions prevailing during a hair colouring process so that the reactive oxidised intermediate formed by oxidation of the developer reacts at that position in the coupler molecule. A bond between the coupler and developer molecule is thus formed at the site of the active leaving group.
  • active leaving groups are H, PhO, Cl, Br, alkoxy (RO) such as phenoxy PhO, and RS- in which R is alkyl or aryl, but any leaving group which leaves during the reaction so as to allow coupling between the reactive intermediate formed from the developer and the coupler is suitable.
  • a preferred compound is l-acetoxy-2- methylnaphthalene .
  • the cyan couplers may be used in relatively low amounts, for instance 0.001 to 1%, preferably 0.004 or 0.00 to 0.5%, for instance not more than 0.05%, all percentages being by weight based on total weight of composition applied to the hair.
  • the couplers may alternatively be selected from 1,3- diketones of the formula II:
  • X and Y are non-leaving substituents and Z is an active leaving group, such that in the presence of an oxidising agent the or each developer reacts with the or each coupler substantially only at the position having the active leaving group Z .
  • These are of the same general type as disclosed in W098/52522 as yellow couplers. These couplers produce a yellow colour on reacting with a developer molecule.
  • Each of X and Y may be independently H, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl aralkyl, - R'NHCOR, -R'CONHR, -ROH, -R'C0 2 R, -R'C0 2 NHR, -NHCOR, -NR 2 , - NHR, -NH 2 , -R'OR and -RO.
  • R can be H, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl or aralkyl and R' can be alkylene, cycloalkylene, alkenylene, cycloalkenylene, arylene, alkarylene or aralkylene. Substituted versions of any of these can be used. Suitable substituents include OH, -OR, Cl, Br, S-C0 2 H, -C0 2 R, -NH 2 and -COR.
  • X and Y are each preferably methyl or ethyl and preferred couplers of the formula II are dimethyl acetoaetamide and diethyl acetoacetamide.
  • the active leaving group Z may be any of the active leaving groups discussed above for the cyan type couplers of the formula I .
  • Yellow couplers may also be selected from compounds of the formula III: in which R 1 , R 2 and R 3 are, independently, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl, aralkyl, -R' NHCOR, - CONHR, -R'CONHR, -R'OH, -R'C0 2 R, -R'S0 2 NHR, -R'OR or
  • R is H, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl or aralkyl and R 1 is alkylene, alkenylene, cycloalkylene, cycloalkenylene, arylene, alkarylene or aralkylene or substituted versions of any of these.
  • Preferred yellow couplers are of the formula II.
  • the amount of yellow coupler is often from 0.05 to 4 wt.%, eg 0.05 to 3 wt.%, but in some cases is up to 5 or 6%. For instance it may from 0.2 to 3 wt.%, eg 0.2 to 2 wt.% based on weight of composition applied to the hair.
  • the couplers may also be selected from compounds of the formula IV:
  • X is a non-leaving substituent
  • Z is an active leaving group
  • Y is an active leaving group or a non- leaving substituent, such that in the presence of an oxidising agent the or each developer reacts with the or each coupler substantially only at the position having the active leaving group Z and, if Y is an active leaving group, Y.
  • Y is a non-leaving substituent.
  • the active leaving groups may be the same as those discussed above for formula I .
  • X can be H, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, alkaryl, aralkyl, -R'NHCOR, -R'CONHR, -R'OH, -R'S0 2 R, -R'S0 2 NHR or -R'OR.
  • Y can be H, -OH, C0 2 H, -C0 2 R, F, Cl, Br, -CN, -N0 2 , CF 3 , alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl, aralkyl, -NH 2 , -NHR, NR2 , -NHCOR, -R'NHCOR, - CONHR, -R'CONHR, NHCONHR, -R'OH, -S0 2 R, -S0 2 NHR, -R'S0 2 R, - R'S0 2 NHR, -SO3H, -OR, -R'OR or -COR.
  • R can be H, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl or aralkyl
  • R' can be alkylene, cycloalkylene, alkenylene, cycloalkenylene, arylene, alkarylene or aralkylene (or substituted versions of any of these) .
  • Suitable substituting groups include -OH, -OR, Cl, Br, F, - C0 2 H, -C0 2 R, -NH 2 and -COR.
  • couplers are of the same general type as disclosed in W098/52522 and give a magenta colour on reaction with the reactive oxidised intermediate formed by reaction of developer molecule and oxidising agent.
  • Y is selected from phenyl and -NHCOR in which R is alkyl . More preferably Y is selected from phenyl and N-acetyl .
  • X is methyl and Y is phenyl; X is phenyl and X is NHCOR, preferably N-acetyl; X is methyl and Y is NHCOR, preferably N-acetyl; X is methyl or phenyl and X is NHCOPhNH 2; X is phenyl and Y is phenyl.
  • Couplers of this type can be used in amounts of from for instance 0.01 to 4%, preferably 0.01 to 2%, more preferably 0.03 to 3, eg 0.03 to 2%, and in some compositions not more than 1 or 0.5%.
  • the couplers may be selected from conventional coupler compounds, in particular disubstituted benzene compounds, especially meta-disubstituted benzene compounds.
  • Total levels of developer and coupler generally vary according to the shade required. For blonde shades amounts of from 0.001 to 4 wt.% are preferred. For red shades amounts of 0.001 to 4 wt.% are preferred. For brown shades amounts of 0.01 to 4% are preferred. For black shades amounts of 0.1 to 4 wt.% are preferred.
  • the compositions may be used in methods of colouring hair. In these methods it is generally necessary to include an oxidising agent in the composition just before it is applied to the hair. Normally the composition of the invention will be supplied in at least two individual packages such as bottles, the oxidising agent being included in one package and the developers being included in another.
  • a preferred oxidising agent is hydrogen peroxide.
  • oxidising agents which may be used include other inorganic peroxygen oxidising agents, preformed organic peroxyacid oxidising agents and other organic peroxides such as urea peroxide, melamine peroxide, and mixtures of any of these.
  • Suitable oxidising agents are preferably water-soluble, that is they have a solubility of at least about 5g in 1,000 ml of deionised water at 25°C ('Chemistry' C.E. Mortimer, 5th Edition, page 277) .
  • the colouring compositions of the invention have pH above 7, in particular above pH 8 or 9. A pH of from 9 to 12 is often suitable.
  • the systems of the invention can also be incorporated into low pH (eg pH 1 to 6) hair colouring systems.
  • the composition of the first aspect of the invention may be supplied to the consumer as a single package containing developer and coupler in a single unit such as a bottle. It is also possible to supply the composition so that the developers are individually packaged and the couplers are individually packaged. Couplers may be supplied as a preformed mixture selected to give a particular colour. Alternatively they can be supplied separately for mixing by the consumer to give a variety of different hair colours.
  • the essential components are mixed to form the composition of the invention before application to the hair.
  • oxidising agent is individually packaged separately from any of the colouring components. It is often mixed with these to form a component of the hair colouring composition before application to the hair. Alternatively it can be applied to the hair separately either before or after the hair colouring composition.
  • the developers, couplers and oxidising agent, and any other materials to be applied to the hair as components of the composition of the invention may be provided in any suitable physical form.
  • a preferred physical form is liquid.
  • the liquid may be of low viscosity, for instance it may be water thin, or it may be of higher viscosity.
  • the material may be suspended in a gel network. The gel may be solid or of low viscosity.
  • the materials for colouring the hair are often formulated so that when they are mixed to form the composition of the invention for application to the hair they form a product of cream-like consistency, which is convenient for application to the hair.
  • the final composition which is applied to the hair is often in the form of an emulsion.
  • Each individual material may be supplied in a form such that the composition containing it has a pH of above or below 7. For instance it may be from pH 1 to 11.
  • the carrier may have a pH of above 6.1 or 6.5 or even above 7 , for instance from pH 8 or 9 to pH 10 or 11.
  • a pH as supplied of from 1 to 6 can assist in improving stability of the components.
  • the materials may be provided such that the pH of the final composition when mixed for application to the hair has a pH below 7 even though one of the components used to form it has a pH of above 7.
  • Alcohols such as ethanol in amounts of from for instance 5 to 10 or 25% may be included to aid solubility of the developers and, particularly, the couplers in a water-based carrier.
  • compositions may contain other optional ingredients.
  • These can include other oxidative and non- oxidative colouring agents, buffering agents, hair swelling agents, catalysts for the oxidising agent, thickeners, diluents, enzymes, surfactants (especially anionic amphoteric, non-ionic or zwitterionic surfactants) , proteins and polypeptides and derivatives thereof; water-soluble or solubilizable preservatives; dye removers; H0 2 stabilisers; moisturising agents; solvents; anti-bacterial agents; low temperature phase modifiers; viscosity control agents; hair conditioning agents; enzyme stabilisers; Ti0 and Ti0 2 - coated mica; perfumes and perfume solubilizers; chelating agents.
  • Other optional materials include anti-dandruff actives such as ZPT. Details of suitable optional ingredients can be found in W098/52522.
  • the equipment used to measure both the initial colour and colour change of substrates (hair/skin) dyed with colouring compositions of the present invention is a Hunter Colourquest spectrophotometer .
  • the value used to express the degree of colour change on any particular substrate is Delta E ( ⁇ E) .
  • a is a measure of the red and green quotients (colour hues) such that positive equates to red and negative to green
  • b is a measure of the yellow and blue quotients (colour hues) such that positive equates to yellow and negative equates to blue.
  • the machine is set to: mode - 0/45; port size - 1 inch; view size - 1 inch; light - D65; field of view -10 ; UV lamp/filter - none.
  • the hair is placed in a sample holder designed to hold the hair in uniform orientation during measurement. Equivalent colorimeters can be used, but it must be ensured that the hair does not move during measurement . The hair must be spread to cover the 1 inch port during colour measurement . Dots are placed on the switch holder to guide the positioning of the holder at the port. The dots are lined up with a mark on the port and readings are taken at each spot .
  • a 4 gramme switch of about 8 inch long hair (or a 2 gramme switch of 4 inch long hair) is hung over a suitable container.
  • the test colouring product is then prepared (ie, where applicable the separate bottle components are mixed together) and about 2 grammes of product per gramme hair is applied directly to the test hair switch.
  • the colourant is massaged through the hair switch for up to about 1 minute and then left on the hair switch for up to about 30 minutes.
  • the coloured hair switch is then cleansed (according to the shampoo protocol IV below) and dried. Drying can be effected either naturally (without heat assistance) or using a drier.
  • the colour development (initial colour) of the coloured, cleansed, dried test hair switch can then be assessed using the Hunter Colourquest spectrophotometer.
  • a 4 gramme, 8 inch test switch (or a 2 gramme, 4 inch test switch) of coloured hair is clamped over a suitable container and rinsed thoroughly for about 10 seconds using warm water (at about 100°F at about 1.5 gallons/minute pressure).
  • Shampoo about 0.1 ml non-conditioning shampoo per gramme hair
  • the shampoo and lathering process is then repeated with a final 60 second rinse. Excess water can be removed (squeezed) from the test switch using the fingers.
  • the test switch is then dried either naturally, or using a pre-heated dryer box at about 140°F (for about 30 minutes) .
  • Switches of virgin yak hair are bleached using the commercially available bleach Clairol 'Born Blond (with camomile'). This is mixed according to the instructions and 10 grams of the material is applied to each switch and massaged in thoroughly. Each switch is wrapped loosely in clingfilm and left for 30 minutes. It is subsequently rinsed for 2 minutes in tap water at 37°C. It is then shampooed once .
  • the emulsion base formulation was as follows:
  • Emulsion Base making method is given below. 1. Add water to vessel. Heat to above the melt temperature of the fatty alcohols with agitation. 2. Add Fatty Alcohols and Ethoxylated Fatty Alcohols, ie Ceteareth-25, Cetyl alcohol, Stearyl alcohol and Steareth-2, and allow to melt. Increase agitation. 3. Add other surfactants, ie Dihydroxyethyl Soyamine
  • Dioleate (Lowenol S216) and di-PEG-2 soyamine IPDI. 4. Continue mixing with shear.
  • the example composition contained (amounts are percentages in the composition finally applied to the hair switches) 0.4% 2, 6-dichloro-para-aminophenol (DCP) as the single electrophilic attack developer, 0.4% paraphenylene diamine (PPD) as the multiple electrophilic attack developer and 1.2% 3-acetamido phenol (3AP) as a cyan coupler.
  • DCP 2, 6-dichloro-para-aminophenol
  • PPD paraphenylene diamine
  • 3AP 3-acetamido phenol
  • An emulsion base having the composition given above was mixed with the colouring components, which had been formed into a colour premix by pre-dissolving in water (with warming to aid dissolution if necessary) with 0.1% EDTA as chelant, 0.1% ascorbic acid and 0.1% sodium sulfite as antioxidants, and 1.23% ammonium acetate as buffer, all amounts being based on the composition finally applied to the hair.
  • the amount of emulsion base in the composition applied to the hair was 49%.
  • Ammonium hydroxide was added to give a final pH of 10 (the amount was 1.8% based on the composition finally applied to the hair) .
  • composition 1 (DCP plus 3AP) 6.70
  • Composition 2 (PPD plus 3AP) 5.00
  • Composition 3 (DCP plus PPD plus 3AP) 2.65.
  • composition 3 were beneficial .
  • the colour from composition 1 had a green colour on the hair.
  • Composition 2 gave a very dark blue/black colouration, with the blue hue tending to be drowned out.
  • Compositon 3 gave a satisfactory vibrant blue/black colour.
  • Example 2 In this example the same single electrophilic attack developer and multiple electrophilic attack developer were used as in example 1.
  • the coupler was a magenta coupler, 3-
  • NAPP N-acetyl amino-1-phenol-2-pyrazolin-5-one
  • compositions having the same components in the same amounts as Example 1 except that the magenta coupler replaces the cyan coupler of Example 1 were applied to hair. Root to tip evenness values were as follows : Composition 4: (DCP plus NAPP) 13.47 Composition 5: (PPD plus NAPP) 2.44
  • Composition 6 (DCP plus PPD plus NAPP) 5.36.
  • composition 6 of the invention gives significantly improved eveness in comparison with composition 4.
  • composition 4 gave a very pink/magenta colour, which is not consumer preferred.
  • Composition 5 appeared very dark violet, again with the magenta hue drowned out.
  • Composition 6 gave a satisfactory vibrant violet/magenta colour.

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Abstract

L'invention concerne une composition pour coloration capillaire comprenant (iv) au moins un développeur sélectionné parmi des systèmes aromatiques aminés pouvant être oxydés, puis ensuite soumis à une seule réaction d'attaque électrophile, (v) au moins un développeur sélectionné parmi des systèmes aromatiques aminés pouvant être oxydés, puis ensuite soumis à deux réactions d'attaque électrophile, et (vi) au moins un coupleur permettant d'obtenir une répartition des pointes aux racines et une couleur de cheveux améliorées.
PCT/US2002/023196 2001-07-24 2002-07-19 Compositions pour coloration capillaire et leur utilisation WO2003009822A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2003515215A JP2004537560A (ja) 2001-07-24 2002-07-19 毛髪着色組成物及びそれらの使用
MXPA04000470A MXPA04000470A (es) 2001-07-24 2002-07-19 Composiciones de coloracion para el cabello y uso de las mismas.
EP02756569A EP1408918A2 (fr) 2001-07-24 2002-07-19 Compositions pour coloration capillaire et leur utilisation
US10/764,191 US7066967B2 (en) 2001-07-24 2004-01-23 Hair coloring compositions and their use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0118030.6 2001-07-24
GB0118030A GB0118030D0 (en) 2001-07-24 2001-07-24 Hair colouring compositions and their use

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US10/764,191 Continuation US7066967B2 (en) 2001-07-24 2004-01-23 Hair coloring compositions and their use

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WO2003009822A2 true WO2003009822A2 (fr) 2003-02-06
WO2003009822A3 WO2003009822A3 (fr) 2003-10-30

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EP (1) EP1408918A2 (fr)
JP (1) JP2004537560A (fr)
CN (1) CN1258354C (fr)
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MX (1) MXPA04000470A (fr)
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WO2016037803A1 (fr) * 2014-09-09 2016-03-17 Henkel Ag & Co. Kgaa Unité de conditionnement (jeu de pièces) comprenant des polymères de silicone aminés spécifiques
WO2016037804A1 (fr) * 2014-09-09 2016-03-17 Henkel Ag & Co. Kgaa Composition d'éclaircissement oxydante comportant des polymères de silicone aminés spéciaux

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DE102016222190A1 (de) * 2016-11-11 2018-05-17 Henkel Ag & Co. Kgaa Verfahren und Einrichtung zum Ermitteln einer Farbhomogenität von Haaren
CN107184424B (zh) * 2017-06-08 2021-01-22 广州天赐高新材料股份有限公司 一种临时毛发染色组合物、永久毛发染色组合物及其制备方法

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EP0079540A2 (fr) * 1981-11-13 1983-05-25 Henkel Kommanditgesellschaft auf Aktien Compositions pour la teinture des cheveux
EP0951900A2 (fr) * 1998-03-03 1999-10-27 Bristol-Myers Squibb Company Compositions de teinture pour cheveux contenant des 2-chloro- et 2,6-dichloro-4-aminophenols et des phenylpyrazolones
WO2001041716A2 (fr) * 1999-12-09 2001-06-14 Henkel Kommanditgesellschaft Auf Aktien Nouvelle combinaison colorante

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EP0079540A2 (fr) * 1981-11-13 1983-05-25 Henkel Kommanditgesellschaft auf Aktien Compositions pour la teinture des cheveux
EP0951900A2 (fr) * 1998-03-03 1999-10-27 Bristol-Myers Squibb Company Compositions de teinture pour cheveux contenant des 2-chloro- et 2,6-dichloro-4-aminophenols et des phenylpyrazolones
WO2001041716A2 (fr) * 1999-12-09 2001-06-14 Henkel Kommanditgesellschaft Auf Aktien Nouvelle combinaison colorante

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016037803A1 (fr) * 2014-09-09 2016-03-17 Henkel Ag & Co. Kgaa Unité de conditionnement (jeu de pièces) comprenant des polymères de silicone aminés spécifiques
WO2016037804A1 (fr) * 2014-09-09 2016-03-17 Henkel Ag & Co. Kgaa Composition d'éclaircissement oxydante comportant des polymères de silicone aminés spéciaux
US10080716B2 (en) 2014-09-09 2018-09-25 Henkel Ag & Co. Kgaa Packaging unit having particular aminated silicone polymer
US10092502B2 (en) 2014-09-09 2018-10-09 Henkel Ag & Co. Kgaa Oxidative hair lighteners with special aminated silicone polymers

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GB0118030D0 (en) 2001-09-19
EP1408918A2 (fr) 2004-04-21
CN1258354C (zh) 2006-06-07
MXPA04000470A (es) 2004-03-18
CN1529581A (zh) 2004-09-15
JP2004537560A (ja) 2004-12-16

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