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WO1999051194A1 - Composition de coloration de cheveux sous forme d'emballage - Google Patents

Composition de coloration de cheveux sous forme d'emballage Download PDF

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Publication number
WO1999051194A1
WO1999051194A1 PCT/US1998/006582 US9806582W WO9951194A1 WO 1999051194 A1 WO1999051194 A1 WO 1999051194A1 US 9806582 W US9806582 W US 9806582W WO 9951194 A1 WO9951194 A1 WO 9951194A1
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WO
WIPO (PCT)
Prior art keywords
cooh
dye
hair colouring
hair
alkyl
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1998/006582
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English (en)
Inventor
Earl David Brock
Heather Holden Harper
Taher Iqbal Yousaf
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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 Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to PCT/US1998/006582 priority Critical patent/WO1999051194A1/fr
Priority to AU69483/98A priority patent/AU6948398A/en
Priority to JP2000541967A priority patent/JP2004500310A/ja
Priority to PCT/US1999/007285 priority patent/WO1999051195A1/fr
Priority to EP99916311A priority patent/EP1067900A1/fr
Priority to CN99806878.0A priority patent/CN1200681C/zh
Priority to AU34659/99A priority patent/AU3465999A/en
Priority to BR9909364-2A priority patent/BR9909364A/pt
Priority to US09/647,577 priority patent/US6398822B1/en
Publication of WO1999051194A1 publication Critical patent/WO1999051194A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—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 condition and structure of human hair is not regular along the length of the hair shaft.
  • Human hair is subject to various chemical and mechanical treatments such as combing, brushing, shampooing, heating, perming as well as exposure to the sun.
  • combing combing
  • brushing brushing
  • shampooing heating
  • perming perming as well as exposure to the sun.
  • the hair at the ends of the hair shaft will generally exhibit greater signs of damage relative to the new growth close to the scalp. This damage can lead to inconsistent coloration when the hair is dyed due to irregular uptake of the hair coloring agents along the length of the hair shaft.
  • the color is resistant to fading, as occasioned by the actions of washing (also known as wash fastness), perspiration, hair spray and other exterior factors such as the action of the sun, and further that the color be retained in a consistent manner for a predictable period of time. Additionally damage to the hair that can lead to irregular dye uptake as discussed above, can lead to increased fading of the damaged portions of the hair and consequently, irregular levels of color fade over time.
  • An additional difficulty commonly associated with the dyeing of human hair is the need for dye systems which avoid any adverse effect on the hair and skin of the user, such as brittle hair, or, irritation of the skin, or, staining (coloring) of the skin.
  • a hair coloring composition which exhibits reduced fade, provides improved resistance to wash out during a regular cleansing regimen, can deliver substantially consistent hair color results throughout the hair, which has reduced irritant effect on the skin , which has reduced staining on the skin, which has reduced adverse effects on the hair of the user and also to develop a convenient and easy-to-use method for the delivery of such a hair coloring composition to the hair.
  • GB-A-0,951,021 (Turner-Hall Corporation) relates to methods and compositions for dyeing keratinous fibres by attaching a dyestuff molecule to a particular site thereof through true covalent bonds.
  • 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 breaking disulfide linkages of keratinous fibres and a hydrogen bond breaker for keratinous fibres and bonding a water-soluble fibre reactive dye compound such as a dichlorotriazine dye to the sulfhydryl groups by applying an aqueous solution of the fibre reactive dye.
  • Thioglycolic acid is disclosed as a reducing agent.
  • US-A-3,415,606 discloses a method for dyeing human hair comprising the steps of treating said hair with an effective amount of mercaptan and then treating the hair with a dichlorotriazine fibre reactive dye.
  • a reducing-H bond breaking solution containing thioglycolate, alkali, lithium bromide and urea
  • Reactive dye hair coloring agents can be used to deliver a variety of hair colors to the hair. However substantial improvement is needed in the areas of color saturation, color development, precise initial color consistency, improved wash fastness, improved hair condition and levels of hair damage.
  • the packaged hair colouring compositions of the present invention comprising a nitrogen-containing heterocycle selected from pyrimidine or triazine, substituted with at least one thio- derivative, provides improvements in colour saturation, colour development, colour consistence, wash fastness, hair condition, and reduction in hair damage and skin irritation.
  • conventional, reactive dye hair coloring compositions typically comprise at least two separately packaged components, which are generally, reducing agent and reactive dye hair coloring agents. These separately packaged components are admixed just prior to application to the hair. Such an admixing step can be messy and inconvenient to the user. Typically, such coloring compositions need to be used soon after admixing due to degradation of the resulting coloring composition. As such, excess admixed coloring composition is disposed of after application of the required amount to the hair.
  • the reactive dyes of the present invention can be incorporated in a singly packaged mixture with improved stability versus conventional reactive dye systems.
  • the singly packaged coloring compositions of the present invention are suitable for use in a multi- application format (i.e. the consumer can use a single package for several color applications over a period of time). It has also been found that the reactive dye compounds and compositions herein are stable over time, and can be stored as such.
  • packaged hair colouring composition comprising a stable aqueous hair colouring composition comprising a compound of formula (I):
  • D is a chromophore
  • X and Y are independently selected from halogen and -SR', provided that at least one of X and Y is -SR', wherein R' is selected from H, C1-C4 alkyl, (CH2) n COOH, (CH2) n CONH2, (CH2) n S0 3 H, (CH )nCOOM, (CH ) n P0 3 H, (CH ) n OH, (CH 2 ) n SS ⁇ 3 " , (CH2) n NR"2, (CH2) n N + R"3, PI1SSO3 " , PhS0 3 H, PhP0 3 H, PhNR"2, PhN + R"3, -CN, SO3 " , (CH2)2CH(SH)R M (CH2)3COOH, - CH2CHOHCH2SH, and N + H,
  • 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 metal, NH4 + or NR"3 + ;
  • L is a linking moiety
  • Z is selected from pyrmidine or triazine
  • R" is C1-C4 alkyl
  • the packaged hair colouring compositions of the present invention provide improved wash fastness of dye on hair, less colour fade over time, improved consumer acceptance in terms of providing a single packaged hair dye composition and improved product stability.
  • the packaged hair colouring composition of the present invention comprises a hair colouring composition comprising a reactive dye compound and a package for said hair colouring composition.
  • suitable packaging for delivering the reactive dye compounds and compositions described herein can be used.
  • suitable packaging include bottle, pump-foamer, and the like.
  • the hair colouring composition comprises a reactive dye which comprises a nitrogen-containing heterocycle, 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):
  • D is a chromophore
  • X and Y are independently selected from halogen and -SR', provided that at least one of X and Y is -SR', wherein R' is selected from H, C1-C4 alkyl, (CH2) n COOH, (CH2) n CONH2, (CH2) n S0 3 H, (CH )nCOOM, (CH 2 ) n P0 3 H, (CH 2 ) n OH, (CH 2 )nSS03 _ , (CH2) n NR * '2, (CH2) n N + R"3, PhSS ⁇ 3 " , PhS0 3 H, PhP0 3 H, PhNR"2, PhN + R"3, -CN, SO3 " , (CH2)2CH(SH)R M (CH2)3COOH, - CH2CHOHCH2SH, and
  • 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 metal, NH4 + or NR"3 + ;
  • 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 present invention.
  • chromophore as used herein means any photoactive compound and includes any coloured or non-coloured light 11
  • absorbing species eg. fluorescent brighteners, UV absorbers, IR absorbing dyes.
  • Suitable chromophore moieties for use in the dye compounds herein include the radicals of monoazo, disazo or polyazo dyes or of heavy metal complex azo dye derived therefrom or of an 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 disclosed in EP-A-0,735,107 (Ciba-Geigy), incorporated herein by reference, including the radicals described therein which contain substituents customary for 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 from Dystar.
  • 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' is selected from H, C1-C4 alkyl, (CH2) n COOH, (CH2)nCONH 2 , (CH 2 ) n S0 3 H, (CH 2 ) n COOM, (CH 2 ) n P0 3 H, (CH 2 ) n OH, (CH2) n SS ⁇ 3 " , (CH2) n NR"2, (CH2) n N + R"3, PI1SSO3 " , PhS0 3 H, PhP0 3 H, PhNR"2, PhN + R"3, -CN, SO3 " , (CH2)2CH(SH)R"(CH2)3COOH, - CH2CHOHCH2SH, and
  • 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 metal, NH4 + or NR"3 + .
  • R' groups for use herein are CH2COOH, CH2CH20H 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-containing heterocycle to each chromophore moiety.
  • Any linking moieties suitable for use in dyeing substrates can be used in the present invention.
  • dyes having the formula (I) can be prepared by reacting suitable precursors of the dye of formula (I) with one another, at least one of which contains a group D-L-Z, wherein D, L and Z are as defined above, at least one of which contains an SR' group (wherein R' is as defined above).
  • dye compounds of the invention having a formula (I) wherein Z is a triazine heterocycle can be prepared by reacting one mole of dichlorotriazine dye, such as those commercially available from BASF 15
  • RTM Procion
  • 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 those commercially available from Clariant under the tradenames Drimalan F (RTM) and Drimarene R or K (RTM), or a trichloropyrimidine dye such as those commercially available from Clariant under the tradename Drimarene X, with a suitable reactant containing an SR' group.
  • a difluoromonochloro pyrimidine dye such as those commercially available from Clariant under the tradenames Drimalan F (RTM) and Drimarene R or K (RTM)
  • a trichloropyrimidine dye such as those commercially available from Clariant under the tradename Drimarene X
  • 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 being dyed.
  • suitable carrier materials will be well known to those skilled in the art.
  • Any carrier materials suitable for use in hair dye compositions can be used herein.
  • compositions of the present invention comprise from about 0.01% to about 10%, preferably from about 0.1% to about 5%, especially from about 0.1% to about 3% by weight of one or more reactive dye compounds having the formula (I).
  • the types and levels of dyes used in each composition will depend upon the desired hair shade.
  • a preferred ingredient in the hair dye compositions herein is a reducing agent.
  • Any reducing agents suitable for use in hair dye compositions may be used herein. Some typical reducing agents for use herein are listed in GB-A-951,021 and GB-A-589,956, incorporated herein by reference.
  • suitable reducing agents include thioglycolic acid, thiolactic acid, dihydrolipoate, thioglycerol, mercaptopropionic acid, sodium bisulfite, ammonium bisulfide, zinc formaldehyde sulfoxylate, sodium formaldehyde sulfoxylate, sodium metabisulfite, potassium borohydride and hydroquinone.
  • Particularly suitable for use herein is thioglycolic acid. 16
  • a hydrogen bond breaker 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, formamide, potassium chloride and magnesium chloride. Particularly preferred for use herein is urea.
  • the coloring compositions of the present invention have a pH in the range of from about 7 to about 11 , preferably from about 9 to about 10.5. In order to maintain such a pH the compositions may contain one or more optional buffering agents.
  • alkaline buffering agents are ammonium hydroxide, ethylamine, dipropylamine, triethylamine and alkanediamines such as 1,3- diaminopropane, anhydrous alkaline alkanolamines such as, mono or di- ethanolamine, preferably those which are completely substituted on the amine group such as dimethylaminoethanol, poly alky lene poly amines such as diethylenetriamine or a heterocyclic amine such as morpholine as well as the hydroxides of alkali metals, such as sodium and potassium hydroxide, hydroxides of alkali earth metals, such as magnesium and calcium hydroxide, basic amino acids such as L-argenine, lysine, alanine, leucine, iso-leucine, oxy lysine and histidine and alkanolamines such as dimethylaminoethanol and aminoalkylpropanediol and mixtures thereof.
  • ion forming compounds compounds that form HCO3 " by dissociation in water
  • suitable ion forming compounds are Na2C ⁇ 3, NaHC ⁇ 3, K2CO3, (NH4)2C03, NH4HCO3, CaC ⁇ 3 and Ca(HC ⁇ 3) and mixtures thereof.
  • 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 % to about 10% , more preferably from about 0.5% to about 5% by weight.
  • Thickening agents suitable for use in the compositions herein are selected from oleic acid, cetyl alcohol, oleyl alcohol, sodium chloride, cetearyl alcohol, stearyl alcohol, synthetic 17
  • thickeners such as Carbopol, Aculyn and Acrosyl and mixtures thereof.
  • Preferred thickeners for use herein are Aculyn 22 (RTM), steareth-20 methacrylate copolymer; Aculyn 44 (RTM) ,polyurethane resin and Acusol 830 (RTM), acrylates copolymer which are available from Rohm and Haas, Philadelphia, PA, USA.
  • Additional 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 invention.
  • the compositions according to the present invention may include one or more solvents as additional diluent materials.
  • solvents suitable for use in the coloring compositions of the present invention are selected to be miscible with water and innocuous to the skin.
  • 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 preferred.
  • a preferred group includes ethanol, isopropanol, n- propanol, butanol, propylene gly col, ethylene gly col monoethyl ether, and mixtures thereof.
  • Water is the preferred principal diluent in the compositions according to the present invention. Principal diluent, as defined herein, 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%, preferably from about 15% to about 99.5%, more preferably at least from about 30% to about 99%, and especially from about 50% to about 98% by weight of the compositions herein.
  • compositions of the present invention can additionally contain a surfactant system.
  • Suitable surfactants for inclusion in the compositions of the invention generally have a lipophilic chain length of from about 8 to about 22 carbon atoms and can be selected from anionic, cationic, nonionic, amphoteric, zwitterionic surfactants and mixtures thereof. 18
  • 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 condensates, and mixtures thereof.
  • Alkyl and/or acyl chain lengths for these surfactants are Ci 2-C22 > preferably Ci2-Cl8 more preferably Cj2-Cl
  • compositions of the invention can also comprise water-soluble nonionic surfactant(s).
  • surfactants of this class include C12-C14 fatty acid mono-and diethanolamides, sucrose polyester surfactants and polyhydroxy fatty acid amide surfactants having the general formula below.
  • N-alkyl, N-alkoxy or N-aryloxy, polyhydroxy fatty acid amide surfactants according to the above formula are those in which Rg is C5-C31 hydrocarbyl, preferably C ⁇ -Cio. hydrocarbyl, including straight- chain and branched chain alkyl and alkenyl, or mixtures thereof and R9 is typically hydrogen, Cj-Cs alkyl or hydroxyalkyl, preferably methyl, or a group of formula -R1-0-R2 wherein Rl is C2-C8 hydrocarbyl including straight-chain, branched-chain and cyclic (including aryl), and is preferably C2-C4 alkylene, R ⁇ is Ci-Cs straight-chain, branched-chain and cyclic hydrocarbyl including aryl and oxyhydrocarbyl, and is preferably C1-C4 alkyl, especially methyl, or phenyl.
  • Z2 is a polyhydroxyhydrocarbyl moiety having a linear hydrocarbyl chain with at least 2 (in the case of glyceraldehyde) or at least 3 hydroxyls (in the case of other reducing sugars) directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) thereof.
  • Z2 preferably will be derived from a reducing sugar in a reductive amination reaction, most preferably Z2 is a 19
  • Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose, mannose, and xylose, as well as glyceraldehyde.
  • high dextrose com symp, high fructose com symp, and high maltose com symp can be utilised as well as the individual sugars listed above.
  • These com 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 will be selected from the group consisting of -CH 2 -(CHOH) n -CH OH, -CH(CH 2 OH)-(CHOH) n _ ⁇ -CH2H, CH2(CHOH)2(CHOR')CHOH)-CH2 ⁇ H, where n is an integer from 1 to 5, inclusive, and R' is H or a cyclic mono- or polysaccharide, and alkoxylated derivatives thereof. As noted, most preferred are glycityls wherein n is 4, particularly -CH2-(CHOH)4-CH2 ⁇ H.
  • the most preferred polyhydroxy fatty acid amide has the formula Rg(CO)N(CH3)CH2(CHOH)4CH2 ⁇ H wherein Rg is a C6-C19 straight chain alkyl or alkenyl group.
  • Rg-CO- N ⁇ can be, for example, cocoamide, stearamide, oleamide, lauramide, myristamide, capricamide, palmiamide, tallowamide, etc.
  • Suitable oil derived nonionic surfactants for use herein include water soluble vegetable and animal-derived emollients such as triglycerides with a polyethyleneglycol chain inserted; ethoxylated mono and di-glycerides, polyethoxylated lanolins and ethoxylated butter derivatives.
  • water soluble vegetable and animal-derived emollients such as triglycerides with a polyethyleneglycol chain inserted
  • ethoxylated mono and di-glycerides ethoxylated mono and di-glycerides
  • polyethoxylated lanolins polyethoxylated lanolins
  • ethoxylated butter derivatives ethoxylated butter derivatives.
  • One preferred class of 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 preferably from about 30 to about 85, and wherein R comprises an aliphatic radical having on average from about 5 to 20 carbon atoms, preferably from about 7 to 18 carbon atoms.
  • Suitable ethoxylated oils and fats of this class include polyethyleneglycol derivatives of glyceryl cocoate, glyceryl caproate, glyceryl caprylate, 20
  • glyceryl tallowate glyceryl palmate, glyceryl stearate, glyceryl laurate, glyceryl oleate, glyceryl ricinoleate, and glyceryl fatty esters derived from triglycerides, such as palm oil, almond oil, and corn oil, preferably glyceryl tallowate and glyceryl cocoate.
  • Preferred for use herein are polyethyleneglycol based polyethoxylated C9- C15 fatty alcohol nonionic surfactants containing an average of from about 5 to about 50 ethyleneoxy moieties per mole of surfactant.
  • Suitable polyethylene glycol based polyethoxylated C9-C15 fatty alcohols suitable for use herein include C9-C11 Pareth-3, C9-C11 Pareth-4, C9-C11 Pareth-5, C9-C11 Pareth-6, C9-C11 Pareth-7, C9-C11 Pareth-8, C11-C15 Pareth-3, C11-C15 Pareth-4, C1 1-C15 Pareth-5, C11-C15 Pareth-6, Cn- C15 Pareth-7, C11-C15 Pareth-8, C11-C15 Pareth-9, C1 1-C15 Pareth-10, C11-C15 Pareth-11, C11-C15 Pareth-12, C11-C15 Pareth-13 and C11-C15 Pareth-14.
  • PEG 40 hydrogenated castor oil is commercially available under the tradename Cremophor (RTM) from BASF.
  • RTM Cremophor
  • PEG 7 glyceryl cocoate and PEG 20 glyceryl laurate are commercially available from Henkel under the tradenames Cetiol (RTM) HE and Lamacit (RTM) GML 20 respectively.
  • 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 ethers of ceteryl alcohol such as Ceteareth 25 which is available from BASF under the trade name Cremaphor A25.
  • nonionic surfactants derived from composite vegetable fats extracted from the fruit of the Shea Tree (Butyrospermum Karkii Kotschy) and derivatives thereof.
  • ethoxylated derivatives of Mango, Cocoa and Illipe butter may be used in compositions according to the invention. Although these are classified as ethoxylated nonionic surfactants it is understood that a certain proportion may remain as non- ethoxylated vegetable oil or fat.
  • suitable 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 oil, peach pit oil, poppyseed oil, pine oil, 21
  • castor oil soybean oil, avocado oil, safflower oil, coconut oil, hazelnut oil, olive oil, grapeseed oil, and sunflower seed oil.
  • 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 ammonium derivatives of formula (VIII)
  • R ⁇ , R2 and Z are as defined above;
  • n, m, p, and q are numbers from 1 to 4, and R ⁇ and M are independently selected from the groups specified above;
  • Suitable amphoteric surfactants of type (a) are marketed under the trade name Miranol and Empigen and are understood to comprise a complex mixture of species.
  • the Miranols have been described as having the general formula (VII), although the CTFA Cosmetic Ingredient Dictionary, 3rd Edition indicates the non-cyclic structure (VIII) while the 4th Edition indicates yet another stmctural isomer in which R2 is O-linked rather than N-linked.
  • CTFA Cosmetic Ingredient Dictionary, 3rd Edition indicates the non-cyclic structure (VIII) while the 4th Edition indicates yet another stmctural isomer in which R2 is O-linked rather than N-linked.
  • a complex mixture of cyclic and non- cyclic species is likely to exist and both definitions are given here for sake of completeness.
  • Preferred for use herein, however, are the non-cyclic species.
  • amphoteric surfactants of type (a) include compounds of formula XII and/or XIII in which R ⁇ is CgHi ⁇ (especially iso-capryl), C9H19 and C11H23 alkyl.
  • R ⁇ is CgHi ⁇ (especially iso-capryl), C9H19 and C11H23 alkyl.
  • R ⁇ is CgHi ⁇ (especially iso-capryl), C9H19 and C11H23 alkyl.
  • Ri is C9H19, Z is CO2M and R2 is H
  • Rl Ci 1H23, Z is CO2M and R2 is H.
  • materials suitable for use in the present invention include cocoamphocarboxypropionate, cocoamphocarboxy propionic acid, and especially cocoamphoacetate and cocoamphodiacetate (otherwise referred to as cocoamphocarboxyglycinate).
  • Specific commercial products include those sold under the trade names of Ampholak 7TX (sodium carboxy methyl tallow polypropyl amine), Empigen CDL60 and CDR 60 (Albright & Wilson), Miranol H2M Cone. Miranol C2M Cone. N.P., 23
  • amphoteric surfactants suitable for use herein include Octoxynol-1 (RTM), polyoxethylene (1) octylphenyl ether; Nonoxynol-4 (RTM), polyoxyethylene (4) nonylphenyl ether and Nonoxynol-9, polyoxyethylene (9) nonylphenyl ether.
  • amphoteric surfactants of this type are manufactured and sold in the form of electroneutral complexes with, for example, hydroxide counterions or with anionic sulfate or sulfonate surfactants, especially those of the sulfated Cg- Ci g alcohol, Cg-Cig ethoxylated alcohol or Cg-Cig acyl glyceride types.
  • 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 component content.
  • amphoteric surfactants of type (b) include N-alkyl polytrimethylene poly-, carboxymethylamines sold under the trade names Ampholak X07 and Ampholak 7CX by Berol Nobel and also salts, especially the triethanolammonium salts and salts of N-lauryl-beta-amino propionic acid and N-lauryl-imino-dipropionic acid.
  • Such materials are sold under the trade name Deriphat by Henkel and Mirataine by Rh ⁇ ne-Poulenc.
  • Water-soluble auxiliary zwitterionic surfactants suitable for inclusion in the compositions of the present invention include alkyl betaines of the formula R5R6R7N " (CH2) n C02M and amido betaines of the formula (XII) below:
  • R5 is C ⁇ 1-C22 alkyl or alkenyl
  • Rg and R ⁇ are independently C ⁇ - C3 alkyl
  • M is H, alkali metal, alkaline earth metal, ammonium or alkanolammonium
  • n, m are each numbers from 1 to 4.
  • Preferred betaines include cocoamidopropyldimethylcarboxymethyl betaine, laurylamidopropyldimethylcarboxymethyl betaine and Tego betaine (RTM).
  • auxiliary sultaine surfactants suitable for inclusion in the compositions of the present invention include alkyl sultaines of the formula (XIII) below:
  • R ⁇ is C7 to C22 alkyl or alkenyl
  • R2 and R3 are independently Ci to C3 alkyl
  • M is H, alkali metal, alkaline earth metal, ammonium or alkanolammonium
  • m and n are numbers from 1 to 4.
  • Preferred for use herein is coco amido propylhydroxy sultaine.
  • Water-soluble auxiliary amine oxide surfactants suitable for inclusion in the compositions of the present invention include alkyl amine oxide R5R6R7NO and amido amine oxides of the formula (XIV) below:
  • R5 is C1 1 to C22 alkyl or alkenyl
  • R and R7 are independently C ⁇ to C3 alkyl
  • M is H, alkali metal, alkaline earth metal, ammonium or 25
  • alkanolammonium and m is a number from 1 to 4.
  • Preferred amine oxides include cocoamidopropylamine oxide, lauryl dimethyl amine oxide and myristyl dimethyl amine oxide.
  • the hair coloring compositions of the present invention may, in addition to the essential oxidative hair coloring agents, optionally include non- oxidative and other dye materials.
  • Optional non-oxidative and other dyes suitable for use in the hair coloring compositions and processes according to the present invention include both semi-permanent, temporary and other dyes.
  • Non-oxidative dyes as defined herein include the so-called 'direct action dyes' , metallic dyes, metal chelate dyes, fibre reactive dyes and other synthetic and natural dyes.
  • Various types of non-oxidative dyes are detailed in: 'Chemical and Physical Behaviour of Human Hair' 3rd Ed. by Clarence Robbins (pp250-259); 'The Chemistry and Manufacture of Cosmetics' . Volume IV. 2nd Ed.
  • a number of additional optional materials can be added to the coloring compositions herein described each at a level of from about 0.001% to about 5%, preferably from about 0.01% to about 3%, more preferably from about 0.05% to about 2% by weight of composition.
  • Such materials include proteins and polypeptides and derivatives thereof; water-soluble or solubilizable preservatives such as DMDM Hydantoin, Germall 115, methyl, ethyl, propyl and butyl esters of hydroxybenzoic acid, EDTA, Euxyl (RTM) K400, natural preservatives such as benzyl alcohol, potassium sorbate and bisabalol, benzoic acid, sodium benzoate and 2-phenoxyethanol; antioxidants such as sodium sulphite, hydroquinone, sodium bisulphite, sodium metabisulphite, sodium dithionite, erythrobic acid and other mercaptans; dye removers such as oxalic acid, sulphated castor oil
  • sulphate sodium phosphate, and tetrasodium pyrophosphate; and p- hydroxybenzoates
  • moisturising agents such as hyaluronic acid, chitin , and starch-grafted sodium polyacrylates such as Sanwet (RTM) IM-1000, IM- 1500 and IM-2500 available from Celanese Superabsorbent Materials, Portsmith, VA, USA and described in US-A-4,076,663 as well as methyl cellulose, starch, higher fatty alcohols, paraffin oils, fatty acids and the like
  • solvents anti-bacterial agents such as Oxeco (phenoxy isopropanol); low temperature phase modifiers such as ammonium ion sources (e.g.
  • viscosity control agents such as magnesium sulfate and other electrolytes
  • viscosity control agents such as magnesium sulfate and other electrolytes
  • quaternary amine compounds such as distearyl-, dilauryl-, di-hydrogenated beef tallow-, dimethyl ammonium chloride, dicetyldiethyl ammoniumethylsulphate, ditallowdimethyl ammonium methylsulphate, disoya dimethyl ammonium chloride and dicoco dimethyl ammonium chloride
  • hair conditioning agents such as silicones, higher alcohols, cationic polymers and the like
  • enzyme stabilisers such as water soluble sources of calcium or borate species
  • colouring agents Ti ⁇ 2 and Ti ⁇ 2- coated mica
  • perfumes and perfume solubilizers and zeolites such as Valfour BV400 and derivatives thereof and Ca2+/Mg2+ sequestrants
  • polycarboxylates amino polycarboxylates, polyphosphonates, amino polyphospho
  • the present invention is represented by the following non-limiting examples.
  • all concentrations are on a 100% active basis and all percentages are by weight unless otherwise stated and the abbreviations have the following designations.
  • the monothioglycolato triazine dye is prepared using the synthesis route as illustrated in Diagram 1.
  • reaction scheme D is a chromophore and varies depending on which starting dye is used.
  • a variety of Procion (RTM) dyes commercially available from BASF are used as starting materials, in particular, Procion Red MX-8B, Procion Yellow MX-8G and Procion Blue MX-2G.
  • An aqueous dye solution (O.lmol/lOOml, pH 7.5) of a purified Procion (RTM) dichlorotriazine dye is prepared.
  • a 0.1 mol solution of Mercaptoacetic acid is added by slow dripping at a temperature of between 0 and 5°C.
  • the pH of the system is adjusted to 8 using sodium carbonate and HC1.
  • the reaction is then allowed to proceed, at 0 ⁇ 5°C and pH8, for 5-8 hours.
  • the required reaction time is different (7 ⁇ 8 hours for Procion Red MX-8B, ⁇ 6 hours for Procion Yellow MX-8G and ⁇ 5 hours for Procion Blue MX-2G).
  • the monothioethanol triazine dye is prepared using the synthesis route as illustrated in Diagram 2. 29
  • reaction scheme D is a chromophore and varies depending on which starting dye is used.
  • Procion (RTM) Red MX-8G is used as the starting material, but other suitable dichlorotriazine dye compounds can also be used as starting materials such as Procion Yellow MX-8G and Procion Blue MX-2G.
  • 0.1 mole of Procion Red MX-8G dye is dissolved in 150 ml of distilled water and added to a flask. The flask is placed in an ice-water bath. 0.1 moles of thioethanol is then added drop-wise, to the reaction mixture under stirring. The total addition time is one hour.
  • the pH of the reaction scheme is maintained at pH 7-7.5 and the temperature of the reaction system 0-5°C during addition of thioethanol.
  • the reaction is then allowed to proceed at 0- 5°C and pH 7.5-8 (which is corrected using sodium carbonate and HC1) for 5 hours. The endpoint of the reaction is indicated by the pH remaining constant for more than 5 minutes. At this point, the 30
  • the monothiosuccinate triazine dye is prepared using the synthesis route as illustrated in Diagram 3.
  • reaction scheme D is a chromophore and varies depending on which starting dye is used.
  • Procion (RTM) Red MX-8G is used as the starting material, but other suitable dichlorotriazine dye compounds can also be used as starting materials, such as Procion (RTM) Yellow MX-8G and Procion (RTM) Blue MX-2G.
  • TSA denotes thiosuccinate.
  • 0.1 moles of pure Procion Red MX-8G dye and 150ml of distilled water are introduced into a 400ml flask.
  • the flask is placed in an ice-water bath.
  • 0.1 moles of thiosuccinic acid is then added dropwise with stirring.
  • the addition time is 1-1.5 hours.
  • the pH of the reaction system is maintained at pH7.5 and the temperature of the reaction system is 0-5°C throughout the addition of thiosuccinic acid.
  • the reaction is then allowed to proceed, at 0-5°C and pH7.5-8 (which is corrected using sodium carbonate and HCl) for 6 hours.
  • the endpoint of the reaction for this part of the synthesis is indicated by the pH of the reaction system remaining constant for more than 5 minutes.
  • the dye monochloromonothiosuccinate triazine dye is obtained.
  • KCl (35%) of the total solution) is then added to the reaction mixture in order to precipitate the dye. Filtration using Whatman paper follows. The precipitate is then washed with acetone for 4-5 times (50ml of acetone is used each time) to obtain the final dye product.
  • 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 substituted for any suitable difluoromonochloro pyrimidine dye such as those commercially available under the tradename Drimalan and Drimarene dyes, in particular, Drimalan Red FB, Drimalan Yellow F-R, Drimalan Blue F-G, Drimalan Blue F-B, Drimalan Yellow F- 3GL, Drimalan Black F-B, Drimarene Golden Yellow R-G2R, Drimarene Blue R-GL, Drimarene Brill Red R-8B, and Drimarene Brill Red K-4BL.
  • TGA denotes a thioglycolato moiety.
  • Drimalan Red F-B dye and distilled water are introduced into a flask. The flask is then placed in an ice-water bath. 0.1 moles of mercaptoacetic acid is then added dropwise to the reaction mixture with stirring. The total addition time is 1-1.5 hours.
  • the reaction is then allowed to proceed at 5°C and pH 9.8-10 (which is corrected using sodium carbonate and HCl) for 15 hours.
  • the end-of- reaction point for this part of the synthesis is indicated by the pH of the reaction system remaining constant for more than 5 minutes.
  • the mono-5-chloro-2-fluoro-mono-4-thioglycolato pyrimidine dye is obtained.
  • KCl ⁇ 35% of the total solution
  • Filtration using Whatman filter paper follows. The precipitate is then washed with acetone for 4-5 times (...50ml of acetone used each time) to obtain the mono-5- chloro-2-fluoro-mono-4-thioglycolato pyrimidine dye.
  • Dye solutions can be made up using compounds prepared according to Example 1 and packaged in a suitable bottle-type package.
  • 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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Abstract

L'invention concerne une composition de coloration de cheveux sous forme d'emballage comprenant une composition aqueuse et stable de coloration de cheveux qui renferme un composé de formule (I) dans laquelle D représente un chromophore; X et Y sont sélectionnés indépendamment dans l'halogène et -SR', à condition qu'au moins un des X et Y représente SR', où R' est sélectionné dans H, alkyle C1-C4, (CH2)nCOOH, (CH2)nCONH2, (CH2)nSO3H, (CH2)nCOOM, (CH2)nPO3H, (CH2)nOH, (CH2)nSSO3-, (CH2)nNR''2, (CH2)nN+R''3, PhSSO3-, PhSO¿3?H, PhPO3H, PhNR''2, PhN?+R''¿3, -CN, SO3-, (CH2)2CH(SH)R''(CH2)3COOH, -CH2CHOHCH2SH, et (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (12), -CH2CH2NH2. n représente un entier allant de 1 à 4 où, dans la même molécule, n ne représente pas forcément le même entier; et M représente un cation de métal alcalino-terreux, de métal alcalin, NH4+ ou NR''¿3?+. L représente une fraction de liaison; Z est sélectionné dans un groupe de pyrimidine ou triazine; R'' représente un alkyle C¿1?-C4 et un emballage pour ladite composition de coloration de cheveux. Les compositions de coloration de cheveux emballées présentent une résistance améliorée au lavage du colorant appliqué sur les cheveux et une décoloration réduite dans le temps, un bon accueil du consommateur en raison de l'emballage unique contenant la composition de coloration de cheveux et une stabilité du produit améliorée.
PCT/US1998/006582 1998-04-02 1998-04-02 Composition de coloration de cheveux sous forme d'emballage Ceased WO1999051194A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
PCT/US1998/006582 WO1999051194A1 (fr) 1998-04-02 1998-04-02 Composition de coloration de cheveux sous forme d'emballage
AU69483/98A AU6948398A (en) 1998-04-02 1998-04-02 Packaged hair colouring composition
JP2000541967A JP2004500310A (ja) 1998-04-02 1999-04-01 容器入り毛髪着色組成物
PCT/US1999/007285 WO1999051195A1 (fr) 1998-04-02 1999-04-01 Composition de teinture de cheveux en emballage
EP99916311A EP1067900A1 (fr) 1998-04-02 1999-04-01 Composition de teinture de cheveux en emballage
CN99806878.0A CN1200681C (zh) 1998-04-02 1999-04-01 包装的染发组合物
AU34659/99A AU3465999A (en) 1998-04-02 1999-04-01 Packaged hair colouring composition
BR9909364-2A BR9909364A (pt) 1998-04-02 1999-04-01 Composição colorante capilar embalada
US09/647,577 US6398822B1 (en) 1998-04-02 1999-04-01 Packaged hair coloring composition

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PCT/US1998/006582 WO1999051194A1 (fr) 1998-04-02 1998-04-02 Composition de coloration de cheveux sous forme d'emballage

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007110535A2 (fr) 2006-03-24 2007-10-04 L'oréal Composition de teinture comprenant un colorant fluorescent thiol/disulfure a groupe ortho-pyridinium a chaine alkylene interrompue et a charge cationique interne, procede d'eclaircissement des matieres keratiniques a partir de ce colorant
FR2912142A1 (fr) * 2007-02-05 2008-08-08 Oreal Composition de teinture comprenant un colorant fluorescent naphtylimide, procede d'eclaircissement des matieres keratiniques a partir de ce colorant
US7717964B2 (en) 2007-09-21 2010-05-18 L'oreal S.A. Styryl thiol/disulfide compound with a hydroxy(cyclo)alkylamino unit, process for lightening keratin materials using same
US7727287B2 (en) 2007-09-21 2010-06-01 L'oreal S.A. Hemicyanin styryl thiol/disulfide dye, composition comprising hemicyanin styryl thoil/disulfide dye, and method for lightening keratin materials using hemicyanin styryl thiol/disulfide dye
US7744657B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Styrl tetrahydroquinolinium thiol/disulfide dye compound and method for lightening keratin materials using the same
US7744658B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Indole-derived styryl dye comprising an alkylene linker, a dye composition comprising this dye, and a process for lightening keratin materials using this dye
US7780743B2 (en) 2006-03-24 2010-08-24 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity, and method for lightening keratin materials using said at least one fluorescent entity
US8070830B2 (en) 2006-03-24 2011-12-06 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity comprising at least one heterocycle, with at least one internal cationic charge, and method for lightening keratin materials using said at least one fluorescent entity

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2009223950B2 (en) * 2008-03-10 2015-05-07 Perachem Limited Hair colouring composition and methods

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5548071A (en) * 1993-05-17 1996-08-20 Ciba-Geigy Corporation Fiber-reactive triazine dyes with one AZO chromophore having a vinylsulfonyl type reactive radical and a second chromophore

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5548071A (en) * 1993-05-17 1996-08-20 Ciba-Geigy Corporation Fiber-reactive triazine dyes with one AZO chromophore having a vinylsulfonyl type reactive radical and a second chromophore

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007110535A2 (fr) 2006-03-24 2007-10-04 L'oréal Composition de teinture comprenant un colorant fluorescent thiol/disulfure a groupe ortho-pyridinium a chaine alkylene interrompue et a charge cationique interne, procede d'eclaircissement des matieres keratiniques a partir de ce colorant
US7780743B2 (en) 2006-03-24 2010-08-24 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity, and method for lightening keratin materials using said at least one fluorescent entity
US8070830B2 (en) 2006-03-24 2011-12-06 L'oreal S.A. Fluorescent entity, dyeing composition containing at least one fluorescent entity comprising at least one heterocycle, with at least one internal cationic charge, and method for lightening keratin materials using said at least one fluorescent entity
FR2912142A1 (fr) * 2007-02-05 2008-08-08 Oreal Composition de teinture comprenant un colorant fluorescent naphtylimide, procede d'eclaircissement des matieres keratiniques a partir de ce colorant
US7717964B2 (en) 2007-09-21 2010-05-18 L'oreal S.A. Styryl thiol/disulfide compound with a hydroxy(cyclo)alkylamino unit, process for lightening keratin materials using same
US7727287B2 (en) 2007-09-21 2010-06-01 L'oreal S.A. Hemicyanin styryl thiol/disulfide dye, composition comprising hemicyanin styryl thoil/disulfide dye, and method for lightening keratin materials using hemicyanin styryl thiol/disulfide dye
US7744657B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Styrl tetrahydroquinolinium thiol/disulfide dye compound and method for lightening keratin materials using the same
US7744658B2 (en) 2007-09-21 2010-06-29 L'oreal S.A. Indole-derived styryl dye comprising an alkylene linker, a dye composition comprising this dye, and a process for lightening keratin materials using this dye

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CN1200681C (zh) 2005-05-11
BR9909364A (pt) 2001-01-16
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AU6948398A (en) 1999-10-25
JP2004500310A (ja) 2004-01-08
AU3465999A (en) 1999-10-25
WO1999051195A1 (fr) 1999-10-14

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