WO1999015137A1 - Compositions de mousse enzymatiques utilisees dans la coloration de fibres de keratine - Google Patents

Compositions de mousse enzymatiques utilisees dans la coloration de fibres de keratine Download PDF

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Publication number
WO1999015137A1
WO1999015137A1 PCT/DK1998/000406 DK9800406W WO9915137A1 WO 1999015137 A1 WO1999015137 A1 WO 1999015137A1 DK 9800406 W DK9800406 W DK 9800406W WO 9915137 A1 WO9915137 A1 WO 9915137A1
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WO
WIPO (PCT)
Prior art keywords
composition
dyeing
hair
strain
laccase
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PCT/DK1998/000406
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English (en)
Inventor
Niels Henrik SØRENSEN
Original Assignee
Novo Nordisk A/S
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 Novo Nordisk A/S filed Critical Novo Nordisk A/S
Priority to AU91539/98A priority Critical patent/AU737597B2/en
Priority to CA002303125A priority patent/CA2303125A1/fr
Priority to EP98943723A priority patent/EP1014921A1/fr
Priority to JP2000512513A priority patent/JP2001517608A/ja
Publication of WO1999015137A1 publication Critical patent/WO1999015137A1/fr

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/32—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using oxidation dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/66—Enzymes
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/0004—General aspects of dyeing
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
    • D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/32—Material containing basic nitrogen containing amide groups leather skins
    • D06P3/3253—Material containing basic nitrogen containing amide groups leather skins using oxidation dyes

Definitions

  • the present invention relates to enzymatic foam compositions for bleaching or dyeing keratinous fibres such as hair, fur, hide and wool, a method for dyeing such fibres, and the use of a composition containing an oxidation enzyme and a foaming agent for dyeing hair and other keratinous fibres.
  • Hair is often dyed to cover grey hair that appears with age. Further, during the last few decades, hair dyeing has become more and more popular in the western world for purely cosmetic purposes, i.e. the hair is dyed a different colour than its natural colour in order to obtain a desired "look" .
  • hair dyeing compositions on the market today can be divided into three main groups:
  • the temporary hair dyes are only intended to change the natural hair colour for a short period of time and usually function by depositing dyes on the surface of the hair. Such hair dyes are easy to remove with normal shampooing.
  • the dyed colour can survive for five or more shampooings. This is achieved by using dyes having a high affinity for hair keratin and which are able to penetrate into the interior of the hair shaft. Permanent hair dyes are very resistant to sunlight, shampooing and other hair treatments and need only be refreshed about once a month as new hair grows out. With these dyeing systems, the dyes are created directly in and on the hair. Small aromatic dye precursors (e.g. p-phenylene-diamine and o-aminophenol) penetrate deep into the hair, where they are oxidised by an oxidising agent to coloured polymeric compounds. These coloured compounds are larger than the dye precursors and cannot be washed out of the hair.
  • aromatic dye precursors e.g. p-phenylene-diamine and o-aminophenol
  • H 2 0 2 hydrogen peroxide
  • colour builder oxidising agent
  • Dyeing compositions comprising H 2 0 2 are often referred to as "lightening dyes" due to the bleaching effect of H 2 0 2 .
  • H 2 0 2 damages the hair. Further, oxidative dyeing often demands high pH (normally around pH 9-10), which also inflicts damage on the hair and irritation to the scalp. Consequently, it is not recommendable to dye the hair too often with dye compositions comprising H 2 0 2 .
  • EP patent No. 0504005 (Perma S.A.) concerns compositions for dyeing hair which do not require the presence of H 2 0 2 .
  • the compositions comprise an enzyme capable of catalyzing the formation of polymeric dyes and also dye precursors, such as bases and couplers, in a buffer solution wherein the pH of the composition is between 6.5 and 8, the enzyme having an optimal activity in this pH range.
  • Rhizoctonia praticola laccase and Rhus vernicifera laccase have a pH-optimum between 6.5 and 8 and can be used to form the polymeric dyes according to this patent.
  • the object of the present invention is to provide improved enzyme-based compositions for bleaching or dyeing of hair and other keratinous fibres, in particular compositions which provide the advantages made possible by use of oxidative enzymes, e.g. reduced damage to hair, but which at the same time result in an improved uniformity of the hair dyeing effect.
  • hair dyeing compositions comprising an oxidation enzyme and a foaming agent result in improved uniformity of the dyeing effect, in particular an improved dyeing of the parts of the hair removed from the air interface.
  • foam compositions of the invention serve to provide oxygen for the enzymatic oxidation process to parts of the hair that would otherwise rapidly suffer from an insufficient supply of oxygen, thereby ensuring that oxidation can proceed more uniformly throughout the hair.
  • a more uniform hair dyeing is obtained, with reduced variation in hair colour intensity between different areas of the hair.
  • the invention thus relates to an enzymatic foam composition adapted for dyeing of keratinous fibres, comprising 1 ) at least one oxidation enzyme, 2) at least one foaming agent, 3) at least one dye precursor and optionally 4) at least one modifier.
  • Another aspect of the invention relates to a method for dyeing keratinous fibres, comprising contacting the fibres with the enzymatic foam composition for a period of time and under conditions sufficient to permit oxidation of the dye precursor to a coloured compound
  • a further aspect of the invention relates to the use of the enzymatic foam composition for oxidative dyeing of keratinous fibres, in particular hair, fur, hide or wool.
  • Figure 1 shows the effect on colour uniformity by dyeing with a foam formulation of the invention (See Example 1 )
  • the first and second columns shows the Coefficient of Variance (CV) (determined as ⁇ L* and ⁇ E*) for a dyeing composition comprising foam SDS-Betaine-pPD-Laccase;
  • the third and fourth columns show the CV of a dyeing composition comprising foam SDS-pPDP-Laccase;
  • the fifth and sixth columns show the CV of a dyeing composition comprising pPD-laccase-water.
  • CV Coefficient of Variance
  • Figure 2 shows the effect on colour uniformity by dyeing with a foam formulation of the invention (see Example 1 ).
  • the first column shows the Coefficient of Variance (CV) (determined as ⁇ L* and ⁇ E*) for a dyeing composition comprising foam SDS- Betaine-oAP-Laccase;
  • the second column shows the CV of a dyeing composition comprises foam SDS-OAP-Laccase;
  • the third column shows the CV of a dyeing composition comprising oAP-laccase-water.
  • Figure 3 shows the effect of hair dyeing using tyrosinase as the oxidation enzyme.
  • composition of the invention comprising 1 ) at least one oxidation enzyme and 2) at least one foaming agent is in particular a composition adapted for dyeing keratinous fibres, e.g. hair, fur, hide or wool.
  • the composition of the invention further comprises 3) at least one dye precursor and optionally 4) at least one modifier.
  • a preferred use of the composition is as a permanent dye for the dyeing of human hair.
  • the oxidation enzyme is an oxidoreductase, i.e. an enzyme classified under the Enzyme Classification number E.C. 1 (Oxidoreductases) in accordance with the
  • oxidoreductases are preferred which catalyse the oxidation of a substrate (an electron or hydrogen donor) by acting on oxygen (0 2 ) and/or a peroxide as the acceptor.
  • Such enzymes include enzymes classified within the enzyme classes comprising oxidases, including E.C. 1 .1 .3. E.C. 1 .2.3, E.C. 1 .3.3, E.C. 1 .4.3, E.C. 1 .5.3, E.C. 1 .7.3, E.C. 1 .8.3 and E.C. 1 .9.3, laccases and related enzymes in E.C. 1 .10.3, and peroxidases in E.C. 1 .1 1.
  • oxidoreductases are specifically contemplated: a) Laccases or related enzymes, which act on molecular oxygen and yield water (H 2 0) without any need for peroxide (e.g. H 2 0 2 ), b) Oxidases, which act on molecular oxygen (0 2 ) and yield peroxide (H 2 0 2 ), and c) Peroxidases, which act on peroxide (e.g. H 2 0 2 ) and yield water (H 2 0). Also, enzyme systems which comprise a combination of more than one enzyme from a single group or from different groups among the three types of enzymes are contemplated.
  • laccases and related enzymes are laccases and related enzymes, the term "laccases and related enzymes" including enzymes comprised by the enzyme classification E.C. 1 .10.3.2 (laccases) and catechol oxidase enzymes comprised by E.C. 1 .10.3.1 , bilirubin oxidase enzymes comprised by the enzyme classification E.C. 1 .3.3.5 and mono-phenol mono-oxygenase enzymes comprised by the enzyme classification E.C. 1 .14.99.1 . Laccases are multi-copper containing enzymes that catalyze the oxidation of phenols and aromatic amines.
  • Laccase-mediated oxidations result in the production of aryioxy-radical intermediates from suitable phenolic substrates; the ultimate coupling of the intermediates so produced provides a combination of dimeric, oligomeric, and polymeric reaction products.
  • Certain reaction products can be used to form dyes suitable for dyeing hair.
  • the laccase may be derived from a microorganism, e.g. a fungus or a bacteria, or a plant.
  • the laccase employed is derived from a fungus. More preferably, it is derived from a strain of Polyporus sp., in particular a strain of P. pinsitus or P. versicolor, a strain of Myceliophthora sp., e.g. M.
  • thermophila a strain of Rhizoctonia sp., in particular a strain of Rh. praticola or Rh. solani, a strain of Pyricularia sp, in particular P. oryzae, or a strain of Scytalidium, such as S. thermophiHum.
  • the laccase may also be from a plant such as Rhus sp., e.g. Rhus vernicifera,
  • the oxidoreductase is a laccase such as a Polyporus sp. laccase, especially the Polyporus pinisitus laccase (also called Trametes villosa laccase) described in WO 96/00290 (from Novo Nordisk Biotec Inc.) or a Myceliophthora sp. laccase, especially the Myceliophthora thermophila laccase described in WO 95/33836 (from Novo Nordisk Biotech Inc.).
  • a laccase such as a Polyporus sp. laccase, especially the Polyporus pinisitus laccase (also called Trametes villosa laccase) described in WO 96/00290 (from Novo Nordisk Biotec Inc.) or a Myceliophthora sp. laccase, especially the Myceliophthora thermophila laccase described in WO 95/33836 (from Novo Nordisk Biotech Inc.).
  • the laccase may be a Scytalidium sp. laccase such as the S. thermophiHum laccase described in WO 95/33837 and WO 97/19998 (from Novo Nordisk Biotech Inc.), the contents of which is incorporated herein by reference, or a Pyricularia sp. laccase, such as the Pyricularia oryzae laccase which can be purchased from SIGMA under the trade name SIGMA No. L5510, or a Coprinus sp. laccase, such as a C. cinereus laccase, especially a C. cinereus IFO 301 1 6 laccase, or a Rhizoctonia sp. laccase, such as a Rh. solani laccase, especially the neutral Rh.
  • a Scytalidium sp. laccase such as the S. thermophiHum laccase described in WO 95/33837 and WO 97/19998 (from Novo Nordisk Biotech Inc.), the contents of which is incorporated herein by reference,
  • solani laccase described in WO 95/07988 (from Novo Nordisk A/S) having a pH optimum in the range of from 6.0 to 8.5.
  • the laccase may also be derived from a fungus such as Collybia, Fomes, Lentinus, P/eurotus, Aspergillus, Neurospora, Podospora, Phlebia, e.g. P. radiata (WO 92/01046), Coriolus sp., e.g. C. hirsitus (JP 2-238885), or Botrytis.
  • Bilirubin oxidase may preferably be derived from a strain of Myrothecium sp., such as M. verrucaria.
  • Oxidases yielding peroxide are typically used in combination with a peroxidase to remove or at least reduce the peroxide produced.
  • Suitable oxidases include glucose oxidase (E.C. 1 .1 .3.4), hexose oxidase (E.C. 1 .1 .3.5), L-amino-acid oxidase (E.C. 1 .4.3.2), xylitol oxidase, galactose oxidase (E.C. 1 .1 .3.9), pyranose oxidase (E.C. 1 .1 .3.10) and alcohol oxidase (E.C. 1 .1 .3.13).
  • an L-amino acid oxidase may be derived from a Trichoderma sp. such as Trichoderma harzianum, such as the L-amino acid oxidase described in WO 94/25574 (from Novo Nordisk A/S), or Trichoderma viride.
  • a suitable glucose oxidase may originate from Aspergillus sp., such as a strain of Aspergillus niger, or from a strain of Cladosporium sp. in particular Cladosporium oxysporum.
  • Hexose oxidases from the red sea-weed Chondrus crispus commonly known as Irish mossKSullivan and Ikawa, (1 973), Biochim. Biophys. Acts, 309, p. 1 1 -22; Ikawa, (1982), Meth. in Enzymol.
  • oxidise a broad spectrum of carbohydrates, such as D-glucose, D-galactose, maltose, cellobiose, lactose, D-glucose 6-phosphate, D-mannose, 2-deoxy-D-glucose, 2-deoxy-D-galactose, D-fructose, D-glucuronic acid, and D-xylose.
  • carbohydrates such as D-glucose, D-galactose, maltose, cellobiose, lactose, D-glucose 6-phosphate, D-mannose, 2-deoxy-D-glucose, 2-deoxy-D-galactose, D-fructose, D-glucuronic acid, and D-xylose.
  • the foaming agent may be present in the form of a single agent or a combination of two or more agents.
  • the foaming agent is typically selected from soaps and ani- onic, cationic, non-ionic, amphoteric, sugar surfactants and/or zwitterionic surfactants and mixtures thereof.
  • the foaming agent(s) may be present at levels of from 0.1 % to 1 5%, preferably from 0.2 to 1 3%, more preferably from 0.25 to 10% , e.g. from 0.5 to 8% by weight of the final composition.
  • anionic surfactants suitable for use as the foaming agent are soaps, e.g.
  • isopropanol 2-methyl-2-amino-1 ,3-propandiol salts of fatty acids such as laurate, myristate, palmitate, stearate, isostearate, behenate, oleate, linoleate, etc.; fatty alcohol ether sulfates such as sodium lauryl ether sulfate; fatty alcohol sulfates such as sodium lauryl sulfate (SLS and SDS); sulfo succinates, e.g.
  • non-ionic surfactants suitable for use as the foaming agent are especially the nonionic fatty acids and fatty amines that often are used as foam stabilisers, thickeners and boosters, e.g. fatty acid alkanol amides and dialkanol amides and fatty acid alkanol amide polyglycol ethers and fatty amine oxides.
  • amphoteric surfactants suitable for use in combination with anionic surfactants as the foaming agent are alkyl betaines, alkyl imidazolinium betaines, alkyl sulfo betaines, amidoalkyl betaines, N-alkyl- ⁇ -amino propionates, etc.
  • foaming agents in the form of sugar surfactants include (a) alkyl- and/or alkenyloligoglycosides and/or (b) fatty acid-N-alkylpolyhydroxyalkylamides.
  • the alkyl- and/or alkenyloligoglycoside (a) may have the formula (I):
  • alkyl and alkenyl oligogiycosides of the formula and b) alkali and/or alkali metal salts of C- 12 . 22 secondary 2,3-alkyl sulphates, where
  • R1 C- 4 . 22 alkyl and/or alkenyl
  • G a sugar residue with 5 or 6 carbon atoms
  • p 1 -10.
  • the weight ratio (l):(ll) is preferably 1 :99-99: 1 .
  • fatty acid-N-alkyl polyhydroxyalkyl amides and sugar surfactants of: saccharose esters, sorbitan esters and/or polysorbates.
  • R 3 C- 6 . 22 alkyl or alkenyl
  • M an alkali or alkaline earth metal, or an ammonium or alkanolammonium ion, preferably Na or Mg
  • n 1 -20, preferably 2-7.
  • R 2 and R 3 are independently a C- 12 . 14 alkyl.
  • a sugar surfactant is a polyglycerin fatty acid ester polyoxyalkylene ether
  • R, R 1 , R 2 C-,- 24 alkyl or C- 8 . 24 alkenyl
  • R 3 C- 1-18 alkylene
  • X a monovalent organic or inorganic anion
  • Y OH or H.
  • Sugar surfactants can also be selected from alkyl oligoglycosides of formula (I) and carboxylic acid N-polyhydroxyalkyiamides of formula (II): R 1 -0(G) (I)
  • foaming agents examples include SDS (sodium dodecyl sulfate), sodium dodecyl ether sulfate and soaps.
  • additives that function as stabilisers, boosters and thickeners, for example one or more compounds selected from fatty acid alkanol amides, dialkanol amides or fatty alkanol amides, polyglycol ethers such as ethoxylated lauric acid monoethanol amide, or fatty amine oxides such as alkyl dimethyl amine oxide.
  • Compositions of the invention may furthermore include, as a stabiliser, a water- soluble polymer capable of stabilising the foam, e.g. one or more of a cellulose derivative such as cationized cellulose, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropylmethyl cellulose, an amphoteric resin, vinylethylether maleate polymer, polyvinyl pyrrolidone and acrylic resin alkanol amine.
  • a stabiliser e.g. one or more of a cellulose derivative such as cationized cellulose, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropylmethyl cellulose, an amphoteric resin, vinylethylether maleate polymer, polyvinyl pyrrolidone and acrylic resin alkanol amine.
  • the dyeing composition of the invention also comprises at least one dye precursor which is converted into a coloured compound (i.e. a dye) by the oxidation enzyme.
  • the dye precursor may be an aromatic compound belonging to one of three major chemical families: the aromatic diamines, aminophenols (or aminonaphthols) and the phenols. Examples of isatin derivative dye precursors can be found in DE 4,314,317- A1 . Further, a number of indole or indoline derivative dye precursors are disclosed in WO 94/00100. The dye precursors mentioned in these documents are hereby incorporated herein by reference.
  • Suitable dye precursors include compounds from the group comprising p-phenylene-diamine (pPD), p-toluylene-diamine, chloro-p-phenylenediamine, p- aminophenol, o-aminophenol, 3,4-diaminotoluene, 2,5-diaminotoluene, 2-methyl-1 ,4- diaminobenzene, 4-methyl-o-phenylenediamine, 2-methoxy-p-phenylenediamine, 2- chloro-1 ,4-diamino-benzene, 4-amino diphenylamine, 1 -amino-4- ⁇ -methoxyethylamino- benzene, 1 -amino-4-bis-( ⁇ -hydroxyethyl)-aminobenzene, 1 -3-diamino-benzene, 2- methyl-1 ,3-diamino-benzene, 2,4-diaminotolu
  • R is an amino, a mono - or disubstituted amino or OR', where R' is H, alkyl, alkenyl, alkynyl, halogenalkyl, nitro, benzyl, phenyl or substituted phenyl, X, Y and Z may each independently be hydrogen, alkyl, alkenyl, alkynyl, halogenalkyl, nitro, benzyl, phenyl, substituted phenyl, amino, hydroxy or mercapto with the proviso that at least one of the groups X, Y and Z is an amino group or a salt thereof.
  • R' is a methyl, ethyl or isopropyl ester are preferred.
  • the oxidoreductase is used with the dye precursor directly to oxidise it into a coloured compound.
  • the dye precursor may be used alone or in combination with other dye precursors.
  • the dyeing composition of the invention (especially hair dyeing compositions) also comprises a modifier (coupler) by means of which a number of colour tints can be obtained.
  • a modifier by means of which a number of colour tints can be obtained.
  • Modifiers are normally used in hair dyeing compositions, as the colours resulting from hair dyeing compositions without a modifier are usually unacceptable for most people.
  • Modifiers are typically m-aromatic diamines, m-aminophenols, polyphenols, amino naphthalines or naphthols.
  • the modifier reacts with the dye precur- sor in the presence of the oxidative enzyme, converting it into a coloured compound.
  • modifiers include m-phenylene-diamine, 2,4-diaminoanisole, 1 - hydroxynaphthalene( ⁇ -naphthol), 1 ,4-dihydroxybenzene(hydroquinone), 1 ,5- dihydroxynapthalene, 1 ,2-dihydroxybenzene(pyrocatechol), 1 ,3-dihydroxybenzene (re- sorcinol), 1 ,3-dihydroxy-2-methylbenzene, 1 ,3-dihydroxy-4-chlorobenzene(4- chlororesorcinol), 1 ,2,3-trihydroxybenzene, 1 ,2,4-trihydroxybenzene, 1 ,2,4-trihydroxy- 5-methylbenzene, and 1 ,2,4-trihydroxytoluene.
  • compositions according to the invention may in addition contain additives and excipients commonly used in hair-dyeing compositions and other cosmetic products, e.g. humectants, oils, thickening agents, antioxidants, buffers, preservatives, fragrances, colours, etc.
  • the invention relates to a method for dyeing keratinous fibres, in particular hair, fur, hide and wool, using a composition as described above.
  • the dyeing method can be conducted with one or more dye precursors and optionally in combination with one or more modifiers.
  • the amount of dye precursor(s) and other ingredients used in the composition of the invention for this purpose are in accordance with usual commercial amounts.
  • Hair dyeing is typically carried out at or near room temperature, preferably around the optimum temperature of the enzyme being used, and at a pH in the range of from 3.0 to 9.0, preferably 4.0 to 8.5, especially 6.0 to 8.0.
  • Suitable dye precursors and optional modifiers are described above.
  • the method of the invention typically will be performed using a single pre-mixed composition applied to the hair or other fibres as a foam comprising the oxidation enzyme, the foaming agent, the dye precursor and the optional modifier in order to obtain the most uniform result
  • the method may alternatively be performed by mixing two or more separate compositions and/or ingredients in order to result in the desired foam composition containing all of the necessary ingredients.
  • Laccase from Myceliophtora termophilia described in WO 95/33837 (available from Novo Nordisk Biotech, Inc.) Dosed as 0.1 mg enzyme per ml of reaction liquid.
  • Dye precursors The dye precursors used were selected from the following: p-phenylene-diamine (pPD) o-aminophenol (oAP)
  • Buffer 0.1 M borate buffer, pH 7.0 with 60 ppm Ca + +
  • Foams are made using foam dispensers or a blender, the foam compositions being gently blended by stirring during production to avoid foam formation at that stage.
  • the following formulations were used:
  • the enzyme is added to the formulation as 0.1 mg enzyme protein per ml dye solution.
  • the enzyme is added to the formulation as 0.1 mg enzyme protein per ml dye solution
  • the enzyme is added to the formulation as 0.1 mg enzyme protein per ml dye solution.
  • a total of 5 ml of reference dye solution is added to the hair (Still water).
  • ⁇ E* sq.root( ⁇ L* 2 + ⁇ a * 2 + ⁇ b * 2 ) and is an expression for the total quantitative colour change.
  • Hair dyeing composition comprising laccase formulated as a foam 1 gram hair wisps were dyed with foam formulations (prepared as described above) while hanging on a sloped metal plate.
  • the foamed dye solutions were massaged into the hair wisps, whereas the reference solution was poured onto the wisps in a 150 ml glass beaker.
  • 1 -2 g of dye formulation was administered on each hair wisp.
  • the dyeing was performed for 30 minutes at a temperature of 30°C, two wisps being used for each formulation.
  • the wisps were hung on the mount and placed in a heating cabinet during the dyeing period.
  • the reference was left untouched. After dyeing, the wisps were rinsed and washed once and then dried.
  • Figure 1 shows the effect on colour uniformity by dyeing with a foam formulation containing the precursor pPD.
  • the two above-mentioned foam formulations are each tested on two hair wisps, the dye uniformity being expressed as the "CV" (coefficient of variance) of ⁇ E* and ⁇ L* after measuring each hair wisp 1 2 times from tip to root.
  • Figure 1 clearly shows that the colour uniformity is better for the hair wisps dyed with the foam formulations. Their CV is significantly lower than for the hair wisps dyed in the "still water” reference solution.
  • Hair dyeing composition comprising tyrosinase formulated as a foam
  • Dye precursor p-phenylene-diamine (PPD) or p-toluene-diamine (PTD)
  • Foam formulation 0.02 g MiniRiskTM shampoo per ml formulation
  • MiniRiskTM contains 1 5% SDS
  • the presursor is then added to the formulation and mixed gently.
  • the formulation foam is made using a foam dispenser.
  • the foam is applied in a maximum amount of about 2.5 g per g of hair by massaging it into the hair wisps.
  • ⁇ E value for PPD is somewhat higher than for PTD, it is still at an acceptable level, in particular in light of the fact that tyrosinase is generally not regarded as an enzyme that is suitable for hair colouring purposes. This example thus shows that when used according to the present invention, acceptable hair dyeing may be obtained with tyrosinase.

Abstract

Cette invention porte sur des compositions de mousse enzymatiques conçues pour teinter des fibres de kératine telles que les cheveux, la fourrure, le cuir ou la laine. ces compositions comprennent: 1) au moins une enzyme d'oxydation, généralement une oxydoréductase sélectionnée à partir de laccases et d'enzymes connexes, d'oxydases et de peroxydases; 2) au moins un agent moussant sélectionné à partir de savons et des tensioactifs anioniques, non ioniques, amphotères et zwittérioniques; 3) au moins un précurseur de colorant sélectionné à partir de diamines, de m-aminophénols et de polyphénols. Cette invention porte également sur un procédé de coloration de fibres de kératine utilisant les compositions de mousse, ainsi que sur l'utilisation de ces compositions de mousse dans la coloration des fibres de kératine. Ces compositions de mousse permettent d'obtenir une meilleure uniformité de l'effet colorant.
PCT/DK1998/000406 1997-09-19 1998-09-18 Compositions de mousse enzymatiques utilisees dans la coloration de fibres de keratine WO1999015137A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU91539/98A AU737597B2 (en) 1997-09-19 1998-09-18 Enzymatic foam compositions for dyeing keratinous fibres
CA002303125A CA2303125A1 (fr) 1997-09-19 1998-09-18 Compositions de mousse enzymatiques utilisees dans la coloration de fibres de keratine
EP98943723A EP1014921A1 (fr) 1997-09-19 1998-09-18 Compositions de mousse enzymatiques utilisees dans la coloration de fibres de keratine
JP2000512513A JP2001517608A (ja) 1997-09-19 1998-09-18 ケラチン線維の染色に適する酵素含有泡沫組成物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DK1077/97 1997-09-19
DK107797 1997-09-19
DK16598 1998-02-05
DK0165/98 1998-02-05

Publications (1)

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WO1999015137A1 true WO1999015137A1 (fr) 1999-04-01

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JP (1) JP2001517608A (fr)
CN (1) CN1270506A (fr)
AU (1) AU737597B2 (fr)
CA (1) CA2303125A1 (fr)
WO (1) WO1999015137A1 (fr)

Cited By (9)

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EP0958806A1 (fr) * 1997-06-11 1999-11-24 Novo Nordisk A/S Composition de coloration capillaire
EP1057471A1 (fr) * 1999-06-04 2000-12-06 L'oreal Composition de teinture d'oxydation des fibres kératiniques et procédé de teinture mettant en oeuvre cette composition
WO2001047487A1 (fr) * 1999-12-24 2001-07-05 Henkel Lion Cosmetics Co., Ltd. Compositions de colorant capillaire d'oxydation moussant de type monocomposant
FR2805460A1 (fr) * 2000-02-25 2001-08-31 Oreal Compositions de teinture des fibres keratiniques contenant des derives d'indolizine cationiques et procede de teinture
JP2003055175A (ja) * 2001-08-07 2003-02-26 Kao Corp 毛髪化粧料
FR2865394A1 (fr) * 2004-01-28 2005-07-29 Oreal Composition de teinture des fibres keratiniques contenant une alcool oxydase et un agent tensio-actif anionique oxyalkylene, procede mettant en oeuvre cette composition
WO2012153318A1 (fr) 2011-05-12 2012-11-15 Centi - Centro De Nanotecnologia E Materiais Técnicos Funcionais E Inteligentes Procédé de coloration de matières avec des colorants naturels et articles correspondants
WO2013087644A3 (fr) * 2011-12-12 2013-11-14 Unilever Plc Procédé de renforcement de la résistance de fibres capillaires
WO2015074821A1 (fr) 2013-11-21 2015-05-28 Unilever Plc Composition de coloration capillaire

Families Citing this family (3)

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Publication number Priority date Publication date Assignee Title
JP5751740B2 (ja) * 2007-10-24 2015-07-22 花王株式会社 二剤式染毛剤
US8740994B2 (en) * 2011-05-11 2014-06-03 Amano Enzyme Inc. Dyeing agent and use for same
CN109354031B (zh) * 2018-10-23 2020-12-25 贺州市骏鑫矿产品有限责任公司 一种钾长石的生产方法

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EP0504005A1 (fr) * 1991-03-08 1992-09-16 PERMA Société Anonyme Composition pour la coloration enzymatique des fibres kératiniques, notamment des cheveux, et son application dans un procédé de coloration
EP0548620A1 (fr) * 1991-12-20 1993-06-30 GOLDWELL GmbH Composition et procédé de coloration oxidative des cheveux humains, utilisant une péroxidase dépourvue d'activité catalase
FR2694018A1 (fr) * 1992-07-23 1994-01-28 Oreal Utilisation de laccases d'origine végétale comme agents oxydants en cosmétique, compositions cosmétiques les contenant, procédé de traitement cosmétique les mettant en Óoeuvre et procédé d'obtention de ces enzymes.
EP0716846A1 (fr) * 1994-12-16 1996-06-19 Yamahatsu Sangyo Kaisha Ltd. Composition tinctoriale pour cheveux à base de colorants d'oxydation
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EP0795313A2 (fr) * 1996-03-16 1997-09-17 Wella Aktiengesellschaft Agent et procédé de coloration par oxydation des fibres kératiniques

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FR2112549A1 (fr) * 1970-11-09 1972-06-16 Procter & Gamble
EP0310675A1 (fr) * 1987-03-31 1989-04-12 Kyowa Hakko Kogyo Kabushiki Kaisha Composition de soins capillaires
EP0504005A1 (fr) * 1991-03-08 1992-09-16 PERMA Société Anonyme Composition pour la coloration enzymatique des fibres kératiniques, notamment des cheveux, et son application dans un procédé de coloration
EP0548620A1 (fr) * 1991-12-20 1993-06-30 GOLDWELL GmbH Composition et procédé de coloration oxidative des cheveux humains, utilisant une péroxidase dépourvue d'activité catalase
FR2694018A1 (fr) * 1992-07-23 1994-01-28 Oreal Utilisation de laccases d'origine végétale comme agents oxydants en cosmétique, compositions cosmétiques les contenant, procédé de traitement cosmétique les mettant en Óoeuvre et procédé d'obtention de ces enzymes.
EP0716846A1 (fr) * 1994-12-16 1996-06-19 Yamahatsu Sangyo Kaisha Ltd. Composition tinctoriale pour cheveux à base de colorants d'oxydation
WO1997023685A1 (fr) * 1995-12-22 1997-07-03 Novo Nordisk Biochem North America, Inc. Procede enzymatique pour la teinture de textile
EP0795313A2 (fr) * 1996-03-16 1997-09-17 Wella Aktiengesellschaft Agent et procédé de coloration par oxydation des fibres kératiniques

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0958806A4 (fr) * 1997-06-11 2000-05-10 Novo Nordisk As Composition de coloration capillaire
EP0958806A1 (fr) * 1997-06-11 1999-11-24 Novo Nordisk A/S Composition de coloration capillaire
US6685750B1 (en) 1999-06-04 2004-02-03 L'oreal S.A. Composition for the oxidation dyeing of keratin fibers and dyeing process using this composition
EP1057471A1 (fr) * 1999-06-04 2000-12-06 L'oreal Composition de teinture d'oxydation des fibres kératiniques et procédé de teinture mettant en oeuvre cette composition
FR2794365A1 (fr) * 1999-06-04 2000-12-08 Oreal Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
US6740129B2 (en) 1999-12-24 2004-05-25 Henkel Lion Cosmetics Co. Ltd. One-pack type post-foamable oxidation hair-dye compositions
WO2001047487A1 (fr) * 1999-12-24 2001-07-05 Henkel Lion Cosmetics Co., Ltd. Compositions de colorant capillaire d'oxydation moussant de type monocomposant
US6579326B2 (en) 2000-02-25 2003-06-17 L'oreal S.A. Compositions for dyeing keratin fibers, containing cationic indolizine derivatives, and dyeing process
FR2805460A1 (fr) * 2000-02-25 2001-08-31 Oreal Compositions de teinture des fibres keratiniques contenant des derives d'indolizine cationiques et procede de teinture
JP2003055175A (ja) * 2001-08-07 2003-02-26 Kao Corp 毛髪化粧料
FR2865394A1 (fr) * 2004-01-28 2005-07-29 Oreal Composition de teinture des fibres keratiniques contenant une alcool oxydase et un agent tensio-actif anionique oxyalkylene, procede mettant en oeuvre cette composition
EP1561453A1 (fr) * 2004-01-28 2005-08-10 L'oreal Compositon de teinture des fibres kératiniques contenant une alcool oxydase et un agent tensio-actif anionique oxyalkyléné; procédé mettant en oeuvre cette composition.
WO2012153318A1 (fr) 2011-05-12 2012-11-15 Centi - Centro De Nanotecnologia E Materiais Técnicos Funcionais E Inteligentes Procédé de coloration de matières avec des colorants naturels et articles correspondants
WO2013087644A3 (fr) * 2011-12-12 2013-11-14 Unilever Plc Procédé de renforcement de la résistance de fibres capillaires
WO2015074821A1 (fr) 2013-11-21 2015-05-28 Unilever Plc Composition de coloration capillaire

Also Published As

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JP2001517608A (ja) 2001-10-09
AU737597B2 (en) 2001-08-23
CA2303125A1 (fr) 1999-04-01
CN1270506A (zh) 2000-10-18
EP1014921A1 (fr) 2000-07-05
AU9153998A (en) 1999-04-12

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