WO2013189965A2 - Composition de coloration capillaire - Google Patents

Composition de coloration capillaire Download PDF

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Publication number
WO2013189965A2
WO2013189965A2 PCT/EP2013/062700 EP2013062700W WO2013189965A2 WO 2013189965 A2 WO2013189965 A2 WO 2013189965A2 EP 2013062700 W EP2013062700 W EP 2013062700W WO 2013189965 A2 WO2013189965 A2 WO 2013189965A2
Authority
WO
WIPO (PCT)
Prior art keywords
oxidase
hair colour
colour composition
hair
hydrogen peroxide
Prior art date
Application number
PCT/EP2013/062700
Other languages
English (en)
Other versions
WO2013189965A3 (fr
Inventor
Ranjit Kaur Bhogal
John Casey
Shovan Ganguli
Karl John Hunter
Jean Hypolites Koek
Sally Pamela Redfern
Original Assignee
Unilever Plc
Unilever N.V.
Conopco, Inc., D/B/A Unilever
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 Unilever Plc, Unilever N.V., Conopco, Inc., D/B/A Unilever filed Critical Unilever Plc
Publication of WO2013189965A2 publication Critical patent/WO2013189965A2/fr
Publication of WO2013189965A3 publication Critical patent/WO2013189965A3/fr

Links

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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9706—Algae
    • A61K8/9722—Chlorophycota or Chlorophyta [green algae], e.g. Chlorella
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9728—Fungi, e.g. yeasts
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9794—Liliopsida [monocotyledons]
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A61K2800/4322—Direct dyes in preparations for temporarily coloring the hair further containing an oxidizing agent
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A61K2800/4324—Direct dyes in preparations for permanently dyeing the hair

Definitions

  • a hair colour composition comprising the flavanonol taxifolin, and either a combination of a peroxidase with either a hydrogen peroxide generator or hydrogen peroxide, or a laccase, wherein the composition has a pH of 4.5 to 7.0, preferably less than or equal to 6.0.
  • the hair colour composition includes metal ions, for example iron or copper, which are able to generate a range of colours for dyeing hair through coordination chemistry with taxifolin, or reaction products thereof with the enzyme.
  • Hair colourant formulations fall into three main categories designated permanent, semi-permanent and temporary. They vary in their degree of wash-fastness where permanent hair colourant formulations last 30-40 shampoo cycles (4-6 weeks) and temporary systems are rinsed out during the first wash.
  • Permanent hair colourant formulations are oxidative dye systems and generally contain paraphenylene diamine (PPD) and resorcinol, both of which have been shown to cause sensitisation and mutagenicity.
  • PPD paraphenylene diamine
  • resorcinol both of which have been shown to cause sensitisation and mutagenicity.
  • severe oxidising conditions required hydroogen peroxide concentrations of 3 % or more and a pH of 8.5 or higher for time periods of 20 minutes or more
  • in themselves can cause skin irritation and sensitization for some individuals as well as hair fibre damage.
  • permanent hair colourant formulations also contain ammonia, used to swell the hair and lift the cuticle scales to allow penetration of dye precursors, which gives off a strong and unpleasant odour.
  • Takada et al. discloses a hair colouring composition comprising laccase and the flavan-3-ol catechin at pH 5.
  • WO 99/16893 (Instituut voor Agrotechno strig Onderzoek (ATO-DLO)) discloses an enzymatic method for the synthesis of organic dyes, comprising bringing together an oxidative enzyme, a hydrogen acceptor and a hydrogen donor wherein at least the hydrogen acceptor or donor is a substrate.
  • Example 3 discloses reactions between peroxidase, hydrogen peroxide and the flavonols myricetin or quercetin.
  • the invention addresses the aforementioned disadvantages by providing a hair colouring compositions which avoids the issues of safety and toxicity associated with the known synthetic oxidative systems, causes less damage by avoiding the use high levels of hydrogen peroxide, whilst maintaining colour fastness.
  • a hair colour composition comprising:
  • composition has a pH of 4.5 to 7.0, preferably less than or equal to 6.0.
  • a method of colouring hair fibres comprising the step of applying the hair colour composition of the first aspect of the invention to hair fibres.
  • the hair colour composition may be applied more frequently, for example daily, in the form of, for example, a shampoo or conditioner thereby addressing the problem of grey hair or natural hair colour re-growth observed during the intervals between hair dyeing treatments. Furthermore by multiple consecutive applications of the hair colour composition, the consumer can also control the degree of colour desired.
  • the hair colour composition may comprise 0.001 - 10, preferably 0.1 - 5 % w/w (+)- taxifolin.
  • Taxifolin The peroxidase is selected from those which are suited to neutral or slightly acid pH, that is to say a pH of 4.5 to 7.0, preferably a pH of less than or equal to 6.0.
  • a pH of 4.5 to 7.0 preferably a pH of less than or equal to 6.0.
  • the advantage of this is that this more closely conforms to the pH of the skin thereby leading to lower levels of skin irritation.
  • the peroxidase is preferably a non-animal haem peroxidase from class II (fungi) or class III (plants and algae), most preferably obtained from the group consisting of Arabidopsis thaliana, horse radish, barley, peanut soybean, tobacco, and turnip (plants), Chlorophyta spirogyra (green algae), Arthromyces ramosus and Corprinus cinereus (fungi).
  • the hair colour composition may comprise 0.0001 - 5, preferably 0.0001 - 1 % w/w peroxidase.
  • a hydrogen peroxide generator When using a peroxidase, a hydrogen peroxide generator is preferred because it reduces the aforementioned problems associated with the use of large amounts of hydrogen peroxide whilst providing a constant supply of hydrogen peroxide.
  • the hydrogen peroxide generator comprises a hydrogen peroxide generating oxidase, a substrate and oxygen.
  • a chemical system can be used to generate hydrogen peroxide such as one based on ascorbate and a transition metal ion, or anthraquinone monosulphate and glucose (T. Vuorinen, Carbohydrate Research, 127, 2, 319-325 (15 April 1984)).
  • the hydrogen peroxide generating oxidase may be selected from the group consisting of (S)-2-hydroxy acid oxidase, D-galactose oxidase, glucose oxidase, coniferyl alcohol oxidase, glycolate oxidase, hexose oxidase, oxalate oxidase, amino acid oxidase and L-galactonolactone oxidase and the respective substrate is selected from the group consisting of (S)-2-hydroxy acid, D-galactose, glucose, coniferyl alcohol, a-hydroxy acids, D-glucose, oxalic acid, amino acid and L- galactono-1 ,4-lactone.
  • the hydrogen peroxide generator is selected from the group consisting of (S)-2-hydroxy acid with (S)-2-hydroxy acid oxidase, D-galactose with D- galactose oxidase, glucose with glucose oxidase, coniferyl alcohol with coniferyl alcohol oxidase, a-hydroxy acids with glycolate oxidase, D-glucose with hexose oxidase, oxalic acid with oxalate oxidase, amino acid oxidase with amino acid and L- galactono-1 ,4-lactone with L-galactonolactone oxidase, all in the presence of oxygen.
  • the hair colour composition may comprise 0.0001 - 3 preferably 0.001 - 1 , most preferably 0.01 - 1 % w/w hydrogen peroxide.
  • the hair colour composition may comprise 0.0001 - 5, preferably 0.001 - 1 % w/w hydrogen peroxide generating oxidase, and 0.01 - 10, preferably 0.1 - 5 % w/w substrate.
  • the hair colour composition of the first aspect may additionally comprise a metal ion suitable for coordinating to taxifolin, or the product of the reaction of taxifolin in the presence of either the peroxidase and hydrogen peroxide, or laccase.
  • the metal ion may be selected from the group consisting of iron (II), iron (III), copper (I), copper (II), and aluminium (III).
  • the hair colour composition may comprise 0.0001 - 2, preferably 0.001 - 0.1 % w/w metal ion.
  • Myceliphthora thermophila laccase (51003) was obtained from Novozymes A/S (Denmark)
  • Soy bean peroxidase was obtained from Bio-Research Products Incorporated (SBP#510)
  • (+)-Catechin hydrate (C1251 ) was obtained from Sigma-Aldrich (UK)
  • Myricetin (M6760) was obtained from Sigma-Aldrich (UK)
  • Taxifolin (78666) was obtained from Sigma-Aldrich (UK)
  • Taxifolin (1 mM); myricetin (2 mM); catechin, quercetin (both 5 mM)
  • switches were rinsed in running tap water until the water ran clear.
  • the hair switch was then dried with a hair dryer and L*a*b* colour measurements taken (6 measurements per switch). This process was repeated up to 4 times. Afterwards the hair switches were washed with 50 ⁇ of shampoo, rinsed in water and dried. This was repeated 4 times.
  • Shampooing was accomplished by fully wetting the switches in tap water and then applying 50 ⁇ _ of shampoo was to each switch, lathering for 2 minutes before rinsing and drying. L*a*b* colour measurements were then taken to assess the amount of colour loss after each shampoo treatment.
  • Taxifolin 1 1.83 ⁇ 1.07 -8.24 ⁇ 1.12 4.90 ⁇ 0.43 6.82 ⁇ 1.31
  • this combination provides a red hue intermediate between that of quercetin/peroxidase/hydrogen peroxide and myricetin/ peroxidase/hydrogen peroxide combinations. Colour fastness after shampoo treatment was observed in all cases.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Botany (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

Les formulations de colorants capillaires sont rangées en trois catégories principales appelées permanente, semi-permanente et temporaire. Les formulations de colorants capillaires permanents sont des systèmes de teinture oxydative et contiennent généralement de la paraphénylènediamine (PPD) et du résorcinol qui sont reconnus comme induisant une sensibilisation et une mutagénicité. En outre, des conditions d'oxydation sévères sont nécessaires, qui provoquent une irritation et une sensibilisation de la peau et qui abîment les fibres capillaires. La composition de l'invention résout les inconvénients susmentionnés sous la forme d'une composition de colorant capillaire comprenant : (a) de la taxifoline ; et soit (b) une combinaison d'une peroxydase avec un générateur de peroxyde d'hydrogène ou de peroxyde d'hydrogène ; la composition présentant un pH de 4,5 à 7,0, de préférence inférieur ou égale à 6,0.
PCT/EP2013/062700 2012-06-21 2013-06-19 Composition de coloration capillaire WO2013189965A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN1776/MUM/2012 2012-06-21
IN1776MU2012 2012-06-21
EP12180571.7 2012-08-15
EP12180571 2012-08-15

Publications (2)

Publication Number Publication Date
WO2013189965A2 true WO2013189965A2 (fr) 2013-12-27
WO2013189965A3 WO2013189965A3 (fr) 2014-05-30

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Application Number Title Priority Date Filing Date
PCT/EP2013/062700 WO2013189965A2 (fr) 2012-06-21 2013-06-19 Composition de coloration capillaire

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210378934A1 (en) * 2018-10-29 2021-12-09 Givaudan Sa Hair care active agent

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999016893A2 (fr) 1997-09-29 1999-04-08 Instituut Voor Agrotechnologisch Onderzoek (Ato-Dlo) Modification enzymatique

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19847276A1 (de) * 1998-10-14 2000-04-20 Henkel Kgaa Färbemittel mit Enzymen
WO2000037031A1 (fr) * 1998-12-22 2000-06-29 Lion Corporation Compositions de coloration capillaire
FR2881953A1 (fr) * 2005-02-11 2006-08-18 Greenpharma Sa Sa Utilisation de derives de la taxifoline comme agents pigmentants et protecteurs de la peau ou des cheveux
JP4995441B2 (ja) * 2005-07-04 2012-08-08 ホーユー株式会社 酸化染毛剤組成物
DE102009044974A1 (de) * 2009-07-23 2011-01-27 Henkel Ag & Co. Kgaa Verwendung von Dihydroquercetin und mindestens einer Aminosäure zur positiven Beeinflussung des natürlichen Pigmentierungsprozesses

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999016893A2 (fr) 1997-09-29 1999-04-08 Instituut Voor Agrotechnologisch Onderzoek (Ato-Dlo) Modification enzymatique

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
T. VUORINEN, CARBOHYDRATE RESEARCH, vol. 127, no. 2, 15 April 1984 (1984-04-15), pages 319 - 325
TAKADA ET AL., JOURNAL OF OLEO SCIENCE, vol. 52, no. 10, 2003, pages 557 - 563

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210378934A1 (en) * 2018-10-29 2021-12-09 Givaudan Sa Hair care active agent

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Publication number Publication date
WO2013189965A3 (fr) 2014-05-30

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