Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/494—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
  • A61K8/4966—Triazines or their condensed derivatives
• • 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
• • 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
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances

Definitions

• This invention relates to a packaged hair colouring composition
• a packaged hair colouring composition comprising a reactive
• dye compound comprising a chromophore and a nitrogen-containing heterocycle comprising at least one thio-substituent.
• the hair at the ends of the hair shaft will generally
• washing also known as wash fastness
• perspiration
• the hair and skin of the user such as brittle hair, or, irritation of the skin, or, staining
• dyeing include, oxidative dyes, direct action dyes, natural dyes, metallic dyes and reactive dyes.
• GB-A-0,951,021 (Turner-Hall Corporation) relates to methods and compositions for
• the method comprises reducing some of the disulfide linkages of the cystine in the fibers to sulfhydryl groups while breaking hydrogen
• bonds by applying to the fibers in alkaline aqueous solution a reducing agent for
• dichlorotriazine dye to the sulfhydryl groups by applying an aqueous solution of the
• Thioglycolic acid is disclosed as a reducing agent
• US-A-3,415,606 discloses a method for dyeing human hair comprising the steps of
• Reactive dye hair coloring agents can be used to deliver a variety of hair colors to the
• present invention comprising a nitrogen-containing heterocycle selected from
• coloring compositions need to be used soon after admixing due to degradation of the resulting coloring composition.
• the singly packaged coloring compositions of the present invention are suitable for use in a multi-application
• compositions herein are stable over time, and can be stored as such.
• packaged hair colouring composition comprising a stable aqueous hair colouring composition
• D is a chromophore
• X and Y are independently selected from halogen and -SR', provided that at
• X and Y are -SR', wherein R' is selected from H, C 1 -C4 alkyl,
• n is an integer in the range of 1 to 4 wherein within the same molecule n is not necessarily the same integer; and M is a cation of alkaline earth metal, alkali
• L is a linking moiety
• Z is selected from pyrimidine or triazine
• R" is C1-C4 alkyl
• the packaged hair colouring compositions of the present invention provide improved
• the packaged hair colouring composition of the present invention comprises a hair
• colouring composition comprising a reactive dye compound and a package for said
• suitable packaging include bottle, pump-
• the hair colouring composition comprises a reactive dye which comprises a nitrogen-
• a chromophore moiety a linking group to link the nitrogen- containing heterocycle to the chromophore.
• the reactive dye compounds used herein have the formula (I) 11
• D is a chromophore
• X and Y are independently selected from halogen and -SR', provided that at
• X and Y are -SR', wherein R' is selected from H, C 1 -C4 alkyl,
• n is an integer in the range of 1 to 4 wherein within the same molecule n is not
• M is a cation of alkaline earth metal, alkali
• L is a linking moiety
• Z is selected from pyrmidine or triazine
• R" is C1-C4 alkyl
• chromophore moieties suitable for use for dying substrates can be used in the
• chromophore as used herein means any photoactive
• any coloured or non-coloured light absorbing species eg. fluorescent brighteners, UV absorbers, IR absorbing dyes.
• Suitable chromophore moieties for use in the dye compounds herein include the
• anthraquinone phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthene, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye.
• Suitable chromophore moieties for use in the dye compounds herein include those
• organic dyes such as sulphonate substituents which enhance the water-soluble properties of the dye compound.
• chromophore D groups for use herein are polysulphonated azo
• chromophores such as those present in Levafix (RTM) dyes commercially available
• the nitrogen containing heterocycle herein is selected from pyrimidine or triazine, preferably triazine.
• the nitrogen containing heterocycle has at least one thio substituent SR' wherein R'
• n is an integer in the range of 1 to 4 wherein within the same molecule n is not
• M is a cation of alkaline earth metal, alkali
• R' groups for use herein are CH2COOH, CH2CH2OH and (COOH) CH2CH2(COOH), preferably CH2COOH.
• the nitrogen-containing heterocycle may be substituted by two SR' groups or by one
• SR' group and one halogen group, preferably by two SR' groups.
• the compounds herein further comprise a linking moiety to link each nitrogen-
• heterocycle is quinoxaline or
• R is H or CH 3 , especially H.
• dyes having the formula (I) can be prepared by reacting suitable
• dye compounds of the invention having a formula (1) wherein Z is a
• triazine heterocycle can be prepared by reacting one mole of dichlorotriazine dye,
• Dye compounds of the invention having a formula (I) wherein Z is a pyrimidine
• heterocycle can be prepared by reacting a difluoromonochloro pyrimidine dye such as
• Drimalan F those commercially available from Clariant under the tradenames Drimalan F (RTM)
• Drimarene R or K (RTM), or a trichloropyrimidine dye such as those 21
• Drimarene X commercially available from Clariant under the tradename Drimarene X, with a suitable reactant containing an SR' group
• the reactions of the starting dye compounds with the reactant containing an SR' group are generally carried out at a pH of from about 7 to about 10, and at a temperature of about 0-5 C
• the dye compounds herein can be incorporated into dye compositions together with
• suitable carrier materials which are selected depending on what type of substrate is
• compositions of the present invention comprise from about 0 01% to about 10%
• a preferred ingredient in the hair dye compositions herein is a reducing agent
• Suitable reducing agents include thioglycolic acid, thiolactic acid, dihydrolipoate, thioglycerol,
• Another preferred ingredient herein is a hydrogen bond breaker. Any hydrogen bond
• breaker suitable for use in a hair dye composition can be used herein. Suitable
• examples include lithium bromide, urea, resorcinol, catechol, dihydroxyacetone,
• urea is urea
• the coloring compositions of the present invention have a pH in the range of from
• compositions may contain one or more optional buffering agents.
• alkaline buffering agents examples include ammonium hydroxide, ethylamine,
• dipropylamine triethylamine and alkanediamines such as 1,3-diaminopropane
• anhydrous alkaline alkanolamines such as, mono or di- ethanolamine, preferably those
• amine group such as dimethylaminoethanol, polyalkylene polyamines such as diethylenetriamine or a heterocyclic amine such as
• hydroxide hydroxides of alkali earth metals, such as magnesium and calcium
• hydroxide basic amino acids such as L-argenine, lysine, alanine, leucine, iso-leucine,
• oxylysine and histidine and alkanolamines such as dimethylaminoethanol and
• aminoalkylpropanediol and mixtures thereof. Also suitable for use herein are 23
• 'ion forming compounds' compounds that form HCO 3 " by dissociation in water
• suitable ion forming compounds are Na2CO 3 ,
• Preferred buffering agents for use herein are ammonium hydroxide, and sodium hydroxide.
• the coloring compositions of the present invention may additionally include a
• thickener at a level of from about 0.05% to about 20%, preferably from about 0 1%
• agents suitable for use in the compositions herein are selected from oleic acid, cetyl
• thickeners such as Carbopol, Aculyn and Acrosyl and mixtures thereof Preferred
• thickeners for use herein are Aculyn 22 (RTM), steareth-20 methacrylate copolymer,
• thickening agents suitable for use herein include sodium alginate or gum arabic, or
• cellulose derivatives such as methyl cellulose or the sodium salt of carboxymethylcellulose or acrylic polymers
• Water is the preferred diluent for the compositions according to the present
• compositions according to the present invention may not be identical to the compositions according to the present invention.
• compositions according to the present invention may not be identical to the compositions according to the present invention.
• solvents 24 include one or more solvents as additional diluent materials Generally, solvents 24
• Solvents suitable for use as additional diluents herein include C]-C20 mono- or polyhydric alcohols and their ethers, glycerine, with monohydric and dihydric alcohols and their ethers preferred. In these compounds, alcoholic residues containing 2 to 10 carbon atoms are
• a preferred group includes ethanol, isopropanol, n-propanol,
• Water is the preferred principal diluent in the compositions according to the present
• Principal diluent means, that the level of water present is higher than the total level of any other diluents
• the diluent is present at a level preferably of from about 5% to about 99.98%,
• compositions of the present invention can additionally contain a surfactant
• compositions of the invention Suitable surfactants for inclusion in the compositions of the invention
• anionic, cationic, nonionic, amphoteric, zwitterionic surfactants can be selected from anionic, cationic, nonionic, amphoteric, zwitterionic surfactants
• Anionic surfactants suitable for inclusion in the compositions of the invention include alkyl sulphates, ethoxylated alkyl sulphates, alkyl glyceryl ether sulfonates, methyl
• acyl taurates fatty acyl glycinates, N-acyl glutamates, acyl isethionates, alkyl sulfosuccinates, alkyl ethoxysulphosuccinates, alpha-sulfonated fatty acids, their salts and/or their esters, alkyl ethoxy carboxylates, alkyl phosphate esters, ethoxylated
• alkyl phosphate esters alkyl sulphates, acyl sarcosinates and fatty acid/protein
• surfactants are C12-C22, preferably C ⁇ -Cj g more preferably C 12 14
• compositions of the invention can also comprise water-soluble nonionic
• surfactant(s) include C 12 14 fatty acid mono-and
• surfactants according to the above formula are those in which Rg is C5-C 3 ]
• hydrocarbyl preferably C ⁇ -CjQ hydrocarbyl, including straight-chain and branched
• R9 is typically hydrogen, C j -Cg alkyl
• R 2 is Cj-Cg straight-chain, branched-chain
• hydrocarbyl including aryl and oxyhydrocarbyl, and is preferably C 1-C4
• Z2 is a polyhydroxyhydrocarbyl moiety having a linear hydrocarbyl chain with at least 2 (in the case of glyceraldehyde) or at least 3
• Z2 is a glycityl moiety.
• Suitable reducing sugars include glucose,
• fructose maltose, lactose, galactose, mannose, and xylose, as well as glyceraldehyde.
• high dextrose corn syrup As raw materials, high dextrose corn syrup, high fructose corn syrup, and high
• maltose corn syrup can be utilised as well as the individual sugars listed above. These corn syrups may yield a mix of sugar components for Z2. It should be understood that it is by no means intended to exclude other suitable raw materials. Z2 preferably
• glycityls wherein n is 4, particularly -CH 2 -(CHOH) 4 -CH 2 OH.
• the most preferred polyhydroxy fatty acid amide has the formula
• Rg-CO-N ⁇ can be, for 27
• Suitable oil derived nonionic surfactants for use herein include water soluble
• oil-derived nonionic surfactants for use herein have the general formula below
• n is from about 5 to about 200, preferably from about 20 to about 100, more
• R comprises an aliphatic radical
• Suitable ethoxylated oils and fats of this class include polyethyleneglycol derivatives of glyceryl cocoate, glyceryl caproate, glyceryl caprylate, glyceryl tallowate, glyceryl
• glyceryl fatty esters derived from triglycerides, such as palm oil, almond oil, and corn
• Preferred for use herein are polyethyleneglycol based polyethoxylated Co-C 15 fatty acids
• alcohol nonionic surfactants containing an average of from about 5 to about 50 ethyleneoxy moieties per mole of surfactant.
• Pareth-6 Cg-Cj 1 Pareth-7, C9-C1 1 Pareth-8, C 1 1 -C 15 Pareth-3, C j J -C J S Pareth-4,
• glyceryl cocoate and PEG 20 glyceryl laurate are commercially available from Henkel
• C9-C11 Pareth-8 is commercially available from Shell Ltd under the tradename Dobanol (RTM) 91-8.
• Particulary preferred for use herein are polyethylene glycol
• ceteryl alcohol such as Ceteareth 25 which is available from BASF under
• nonionic surfactants derived from composite
• Cocoa and Illipe butter may be used in compositions according to the invention.
• a certain proportion may remain as non-ethoxylated vegetable oil or fat.
• oil-derived nonionic surfactants include ethoxylated derivatives of almond oil, peanut oil, rice bran oil, wheat germ oil, linseed oil, jojoba oil, oil of apricot pits, walnuts, palm nuts, pistachio nuts, sesame seeds, rapeseed, cade oil, corn
• peach pit oil poppyseed oil, pine oil, castor oil, soybean oil, avocado oil,
• safflower oil coconut oil, hazelnut oil, olive oil, grapeseed oil, and sunflower seed
• Amphoteric surfactants suitable for use in the compositions of the invention include
• R] is C7-C22 alkyl or alkenyl
• R2 is hydrogen or CH2Z
• each Z is independently CO2M or CH2CO2M
• M is H, alkali metal
• alkaline earth metal ammonium or alkanolammonium, and/or
• n, m, p, and q are numbers from l to 4, and R] and M are
• Suitable amphoteric surfactants of type (a) are marketed under the trade name
• amphoteric surfactants of type (a) include compounds of formula XII and/or XIII in which K ⁇ is CgHj (especially iso-capryl), C9H19 and
• materials suitable for use in the present invention include
• cocoamphocarboxypropionate cocoamphocarboxy propionic acid, and especially
• cocoamphoacetate and cocoamphodiacetate alsowise referred to as
• cocoamphocarboxyglycinate Specific commercial products include those sold under the trade names of Ampholak 7TX (sodium carboxy methyl tallow polypropyl
• amphoteric surfactants suitable for use herein include Octoxynol-1 (RTM), polyoxethylene (1) octylphenyl ether; Nonoxynol-4 (RTM), polyoxyethylene
• hydroxide counterions for example, hydroxide counterions or with anionic sulfate or sulfonate surfactants,
• Ci g acyl glyceride types Note also that the concentrations and weight ratios of the
• amphoteric surfactants are based herein on the uncomplexed forms of the surfactants
• any anionic surfactant counterions being considered as part of the overall anionic surfactant
• amphoteric surfactants of type (b) include N-alkyl
• Water-soluble auxiliary zwitterionic surfactants suitable for inclusion in the compositions of the present invention include alkyl betaines of the formula R5R0R7N " (CH2) n CO2M and amido betaines of the formula (XII) below
• R5 is C] 1-C22 al yl or alkenyl
• Rg and R7 are independently C
• M is H, alkali metal, alkaline earth metal, ammonium or alkanolammonium
• Preferred betaines include cocoamidopropyldimethylcarboxymethyl betaine,
• alkyl sultaines of the formula (XIII) below
• Rj is C7 to C22 alkyl or alkenyl
• R2 and R are independently C ⁇ to C alkyl
• M is H, alkali metal, alkaline earth metal, ammonium or alkanolammonium and
• n and n are numbers from 1 to 4 Preferred for use herein is coco amido
• compositions of the present invention include alkyl amine oxide R5R6R7NO and
• R5 is C ⁇ to C22 alkyl or alkenyl
• Rg and R7 are independently Cj to C 3
• alkyl is H, alkali metal, alkaline earth metal, ammonium or alkanolammonium and
• m is a number from 1 to 4
• Preferred amine oxides include cocoamidopropylamine
• the hair coloring compositions of the present invention may, in addition to the
• essential reactive hair coloring agents optionally include other dye materials
• Suitable optional dyes for use herein include oxidative dyes Any oxidative dye suitable for use in dyeing hair can be used in the compositions herein, for example those mentioned in WO98/27945, incorporated herein by reference in its entirety
• Non-oxidative dyes as defined herein include the so-called 'direct action dyes',
• compositions include proteins and polypeptides and derivatives
• water-soluble or solubilizable preservatives such as DMDM Hydantoin, Germall 115, methyl, ethyl, propyl and butyl esters of hydroxybenzoic acid, EDTA,
• antioxidants such as sodium sulphite, hydroquinone, sodium bisulphite, sodium metabisulphite,
• H2O2 stabilisers such as tin compounds such as sodium stannate, stannic hydroxide and stannous
• octoate acetanilide
• phenacetin colloidal silica such as magnesium silicate
• moisturising agents such as hyaluronic acid, chitin , and starch-
• grafted sodium polyacrylates such as Sanwet (RTM) IM- 1000, IM- 1500 and IM-
• Oxeco phenoxy isopropanol
• low temperature phase modifiers such as ammonium ion sources (e.g. NH4 Cl)
• viscosity control agents such as magnesium sulfate and
• hair conditioning agents such as silicones, higher alcohols, cationic polymers and the like,
• colouring agents Ti ⁇ 2 and Ti ⁇ 2-coated mica, perfumes and perfume solubilizers,
• zeolites such as Valfour BV400 and derivatives thereof and Ca 2+ /Mg 2+
• sequestrants such as polycarboxylates, amino polycarboxylates, polyphosphonates,
• the present invention is represented by the following non-limiting examples.
• all concentrations are on a 100% active basis and all percentages are by
• the monothioglycolato triazine dye is prepared using the synthesis route as illustrated
• reaction scheme D is a chromophore and varies depending on which starting
• dichlorotriazine dye is prepared. To this solution, a 0. Imol solution of
• Mercaptoacetic acid is added by slow dripping at a temperature of between 0 and 5° 39
• dye compounds are then obtained following precipitation and filtration.
• the monothioethanol triazine dye is prepared using the synthesis route as illustrated in Diagram 2.
• reaction scheme D is a chromophore and varies depending on which starting
• Procion Red MX-8G dye 0.1 mole of Procion Red MX-8G dye is dissolved in 150 ml of distilled water and
• reaction is then allowed to proceed at 0-5°C and pH 7.5-8 (which is corrected using sodium carbonate and HCl) for 5 hours.
• the endpoint of the reaction is indicated by
• the monothiosuccinate triazine dye is prepared using the synthesis route as illustrated
• reaction scheme D is a chromophore and varies depending on which starting
• dichlorotriazine dye compounds can also be used as starting materials, such as Procion (RTM) Yellow MX-8G and Procion (RTM) 43
• TSA denotes thiosuccinate attached to the ring via its sulphur atom.
• reaction system is 0-5°C throughout the addition of thiosuccinic acid.
• triazine dye is obtained. Using 6N HCl, the pH of the system is then reduced to
• the mono-5-chloromono4-thioglycolato pyrimidine dye is prepared using the synthesis route as illustrated in Diagram 4.
• Drimalan (RTM) Red FB dye commercially available from Clariant is used as starting material.
• Drimalan Red FB can be used as starting material.
• Drimalan Red FB Drimalan Yellow F-R
• Drimalan Blue F-G Drimalan
• Drimalan Red F-B dye 0.1 moles of Drimalan Red F-B dye and distilled water are introduced into a flask.
• the pH of the reaction mixture is maintained at pH 9.8-10 and at a
• thioglycolato pyrimidine dye is obtained. Using 6N HCl the pH of the system is then
• Dye solutions can be made up using compounds prepared according to Example 1
• the packaged hair colouring compositions of the examples provide improvements in terms of consumer acceptance since no admixing of ingredients is necessary before dyeing, and improved wash fastness.

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• Cosmetics (AREA)

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• 1998
  • 1998-04-02 AU AU69483/98A patent/AU6948398A/en not_active Abandoned
  • 1998-04-02 WO PCT/US1998/006582 patent/WO1999051194A1/en active Application Filing
• 1999
  • 1999-04-01 AU AU34659/99A patent/AU3465999A/en not_active Abandoned
  • 1999-04-01 CN CN99806878.0A patent/CN1200681C/zh not_active Expired - Fee Related
  • 1999-04-01 EP EP99916311A patent/EP1067900A1/en not_active Withdrawn
  • 1999-04-01 BR BR9909364-2A patent/BR9909364A/pt not_active Application Discontinuation
  • 1999-04-01 JP JP2000541967A patent/JP2004500310A/ja active Pending
  • 1999-04-01 WO PCT/US1999/007285 patent/WO1999051195A1/en not_active Application Discontinuation

Non-Patent Citations (1)

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