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WO2013167350A2 - Procédé de coloration de fibres kératineuses - Google Patents

Procédé de coloration de fibres kératineuses Download PDF

Info

Publication number
WO2013167350A2
WO2013167350A2 PCT/EP2013/057770 EP2013057770W WO2013167350A2 WO 2013167350 A2 WO2013167350 A2 WO 2013167350A2 EP 2013057770 W EP2013057770 W EP 2013057770W WO 2013167350 A2 WO2013167350 A2 WO 2013167350A2
Authority
WO
WIPO (PCT)
Prior art keywords
gallic acid
iron
hair
composition
keratinous fibers
Prior art date
Application number
PCT/EP2013/057770
Other languages
English (en)
Other versions
WO2013167350A3 (fr
Inventor
Lalitha Balakrishnan
Indu Mani
Original Assignee
Unilever N.V.
Unilever Plc
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 N.V., Unilever Plc, Conopco, Inc., D/B/A Unilever filed Critical Unilever N.V.
Publication of WO2013167350A2 publication Critical patent/WO2013167350A2/fr
Publication of WO2013167350A3 publication Critical patent/WO2013167350A3/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
    • 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
    • A61K8/20—Halogens; Compounds thereof
    • 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
    • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/67—Vitamins
    • 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
    • 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

Definitions

  • the invention relates to a method and a kit for providing brown colour to
  • the invention more particularly relates to a method and a kit for providing brown colour to hair and reducing the blueness generally obtained with such types of colouring methods.
  • a method of colouring hair comprising contacting hair with an iron salt followed by contacting with gallic acid or an ester thereof, is known. Such a method gives a bluish tinge to the hair which is not liked by some consumers. Consumers generally prefer a more brownish tinge which they believe gives one a natural look. The present inventors have found that giving a high pH treatment to the well known two step process of colouring hair provides the much needed brownish tinge.
  • EP2399567 discloses a mordant for hair dyeing comprising an effective amount of ferrous salt, antioxidant and water and a hair dyeing product comprising three parts: a softening agent, a dyeing agent and the mordant.
  • EP2446876 discloses a combination of the hair dyeing agent and a softener for dyeing hair where the hair dyeing agent comprises a dye active, a mordant active, a stabilizer, water and a carrier and/ or an excipient.
  • the metal-polyphenol complex are applied on the hair at a pH of 3-6 which may be followed by rinsing with water or washing with shampoos where the pH is in the range of 3.5 to 8. It is heretofore not known that giving a high pH of 9 to 12 treatment to the hair after it has been treated with a specific metal-polyphenol complex ensures better brown tinge to the hair which is the invention claimed in the present application.
  • Keratinous fibres as used herein, is meant to include fibers which contain keratin of mammals including humans e.g. hair on the body and head.
  • colouring is meant changing the colour generally from grey which a state where the keratin content is low to a colour which may include black or brown.
  • Preferred colour to be achieved as per the present invention is brown with a minimal blue tint.
  • a composition to achieve this may be generally classified as leave-on or rinse off, preferably rinse off. This may be achieved by including the actives in well known hair care products like shampoo, conditioner and combinations of these.
  • the first aspect of the invention provides for a method of colouring keratinous fibers comprising the steps of (a) contacting the keratinous fibers with a complex of an iron salt with gallic acid or an alkyl ester of gallic acid or a mixture thereof at a pH in the range of 3 to 6; followed by (b) contacting the keratinous fibers with a composition at a pH in the range of 9 to 12.
  • Step (a) in the method above may be carried out by contacting the hair using a complex that has been pre-prepared as a composition.
  • the complex is pre- prepared, it is preferred that the composition is prepared not more than 60 minutes, preferably not more than 20 minutes, further more preferably not more than 5 minutes before contacting the keratinous fibres.
  • An alternate way of achieving this is to include the iron salt in a first composition and the gallic acid or the alkyl ester thereof in a second composition.
  • the complex may be prepared insitu on the keratinous fibers by contacting the fibers first with the composition comprising the gallic acid or alkyl ester thereof followed by contacting the fibres with the iron salt.
  • the fibers are first contacted with the iron containing composition followed by contacting the fibers with the gallic acid or alkyl ester thereof.
  • the sub-steps are preferably carried out not more than 30 minutes, preferably not more than 10 minutes apart.
  • the step of contacting the fibres with the pre-prepared complex is preferred over the sequential sub-steps described above.
  • the iron salt is preferably selected from iron chloride (II), iron chloride (III), iron gluconate (II), iron sulphate, iron ascorbate, or iron tartrate, more preferably from iron chloride (II), or iron gluconate (II).
  • the iron salt is preferably used as an aqueous composition at 0.1 to 10 wt%, preferably 0.5 to 5 wt% by weight of said aqueous composition.
  • Gallic acid and its esters have the structure:
  • the alkyl ester of gallic acid preferably has the alkyl chain length of 1 to 4 carbon atoms of which ethyl, methyl or propyl gallate is preferred. Of these, methyl or propyl gallate are further more preferred.
  • the gallic acid or the alkyl ester thereof is preferably used as an aqueous composition at 0.1 to 10 wt%, preferably 0.2 to 2 wt% by weight of said aqueous composition.
  • the gallic acid is present as an extract of a plant species of the Terminalia genus, or an extract of Embelica officinalis, or Mucuna pruriens.
  • the extract of the Terminalia or Embelica species is preferred.
  • the extract is preferably of the leaf, stem, seed, flower or fruit of the above plant.
  • a suitable method of preparing an extract of the plants comprises the steps of
  • the complex is formed ex-situ or insitu by reaction of an iron salt with gallic acid or alkyl ester of gallic acid.
  • the preferred iron salts are iron chloride (II), iron chloride (III), iron gluconate, iron sulphate, iron ascorbate, or iron tartrate. Of these iron salts iron chloride (II), iron chloride (III), or iron gluconate are more preferred.
  • the iron salt is preferably present in aqueous solution at a pH in the range of 2 to 6, more preferably 3 to 5.
  • the aqueous solution of the iron salt is preferably at a concentration of 0.5 to 5 %. Once the iron salt - gallate complex is formed the pH is in the range of 3 to 6.
  • step (b) which comprises contacting the keratinous fibers with a composition having a pH of 9 to 12.
  • a composition having a pH of 9 to 12 In conventional methods the hair is rinsed with water or with a conditioner composition which generally has a pH in the range of 3.5 to 8. The dramatic increase in the browness of the hair and reduction in the blueness is achieved by carrying out this step of contacting the hair with a high pH composition.
  • This high pH composition may be prepared by included alkaline substances e.g. sodium hydroxide, potassium hydroxide, or cationic polymers like polyethylene imine in this composition.
  • step (b) is carried out after step (a) and the order of this sequence is important.
  • the present inventors have carried out experiments where step (b) is carried out first followed by step (a) and this order does not provide the benefits afforded by the present invention.
  • the step (a) may comprise a composition that is left on hair for a pre-specified period of time from a leave-on composition. Alternately it may be included as a wash-off composition e.g. a shampoo composition. Step (b) may also be a leave-on or wash-off composition. When compositions of step (a) and step (b) are leave-on
  • step (a) comprises contacting hair with a wash off shampoo composition and step (b) comprises contacting hair with a wash off conditioner composition.
  • Step (a) of the method of the invention may be achieved by including the iron- gallate complex in a shampoo composition.
  • the iron salt and the gallic acid / alkyl ester of gallic acid may be kept in separate compartments of a two compartment container and are mixed some time prior to use, to prepare the desired complex.
  • the contents of the two-compartment container may be mixed to prepare a desired shampoo composition which may be used on hair to provide cleaning as well as colouring benefits.
  • the iron-gallate complex when in the form of a shampoo is generally in emulsion form.
  • Other suitable forms in which the complex may be delivered are the cream, or gel form.
  • compositions When the iron salt and the gallic acid / alkyl ester of gallic acids are included in separate compartments of a two compartment container, the individual compositions may be in the form of emulsion, gel, or cream form.
  • Composition at a pH in the range of 9 to 12 used for rinsing the hair after step (a) may be a conditioner composition with alkaline ingredients included to ensure a pH of 9 to 12. It is particularly preferred that the pH of the rinse composition has a pH in the range of 9 to 1 1 . More preferably the pH of the rinse composition is more than 9 but less than 1 1 .
  • kits for colouring keratinous fibers comprising
  • the instructions for use preferably includes the instruction to first apply the mixture of aqueous solution of the iron salt and the gallic acid or an alkyl ester of gallic acid followed by the instruction to apply the composition having a pH in the range of 9 to 12.
  • Comparative Examples A to C Methods outside the invention comprising rinsing with a low pH composition.
  • the white yak hair had the following L * a * b * value
  • Example A The white hair was treated with a solution containing 100 mM ( ⁇ 2 wt%) solution of ferrous chloride (FeCI 2 ) and 50 mM ( ⁇ 1 wt%) gallic acid by incubating for 30 minutes at 25 °C.
  • Example B The white hair was treated with a solution containing 100 mM ( ⁇ 1 .6 wt%) solution of ferric chloride (FeCI 3 ) and 50 mM ( ⁇ 1 wt%) gallic acid by incubating for 30 minutes at 25 °C.
  • Example C The white hair was treated with a solution containing 100 mM (-4.8 wt%) solution of ferrous gluconate and 50 mM ( ⁇ 1 wt%) gallic acid by incubating for 30 minutes at 25 °C.
  • Example D An experiment was carried out similar to Example A
  • Example E An experiment was carried out similar to Example A except that methyl gallate was used instead of gallic acid.
  • the data on the change in colour is summarized in Table - 2.
  • Table - 2 The data on the change in colour is summarized in Table - 2.
  • Example F Process comprising a different sequence of contact
  • the procedure involved first treating the white hair switches with a buffer solution at high pH (of 12) for 5 minutes.
  • the buffer solution contained 50 mM Tris buffer adjusted to the desired pH with 1 N NaOH.
  • the hair switches were then contacted with a solution containing 100 mM ( ⁇ 2 wt%) solution of ferrous chloride (FeCI 2 ) and 50 mM ( ⁇ 1 wt%) of gallic acid by incubating for 30 minutes at 25 °C. The hairs were then washed well under running water.
  • Example 4 The colour intensity of the switches as per Example F and that for Example 4 which was repeated were measured using a chromameter (CR10).
  • CR10 chromameter
  • the invention thus provides for a method of colouring keratinous fibers where the desired level of blackness is obtained while minimising blueness and enhancing browness.

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

Abstract

L'invention concerne un procédé et un kit pour conférer une couleur brune à des fibres kératineuses tout en réduisant la coloration bleue généralement obtenue avec de tels types de procédés de coloration. L'invention concerne l'application d'un traitement à pH élevé de 9 à 12 aux cheveux après les avoir traités avec un complexe métal-polyphénol spécifique.
PCT/EP2013/057770 2012-05-08 2013-04-15 Procédé de coloration de fibres kératineuses WO2013167350A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN1412/MUM/2012 2012-05-08
IN1412MU2012 2012-05-08
EP12173204 2012-06-22
EP12173204.4 2012-06-22

Publications (2)

Publication Number Publication Date
WO2013167350A2 true WO2013167350A2 (fr) 2013-11-14
WO2013167350A3 WO2013167350A3 (fr) 2014-06-26

Family

ID=48190479

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/057770 WO2013167350A2 (fr) 2012-05-08 2013-04-15 Procédé de coloration de fibres kératineuses

Country Status (1)

Country Link
WO (1) WO2013167350A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016216457A (ja) * 2015-05-18 2016-12-22 フロムファーイースト株式会社 毛髪化粧料組成物、毛髪化粧料及び染毛方法
US20180345048A1 (en) * 2017-06-05 2018-12-06 Momentive Performance Materials Inc. Composition and method for strengthening hair fiber
WO2020064269A1 (fr) * 2018-09-25 2020-04-02 Henkel Ag & Co. Kgaa Endommagement réduit des cheveux pendant la décoloration au moyen d'un agent complexant biodégradable
EP3856133A1 (fr) * 2018-09-24 2021-08-04 Henkel AG & Co. KGaA Endommagement réduit des cheveux pendant la décoloration au moyen d'un agent complexant biodégradable

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0327345A2 (fr) 1988-02-04 1989-08-09 Wella Aktiengesellschaft Composition pour rendre plus foncé les cheveux
EP0394930A1 (fr) 1989-04-24 1990-10-31 Kao Corporation Composition pour le traitement des cheveux, composition pour décolorer les cheveux et composition pour modifier la teinte des cheveux
JPH04208214A (ja) 1990-11-30 1992-07-29 Seiho Kikaku Kk 頭髪用染毛剤及びその製造方法並びにその染毛方法
EP2399567A1 (fr) 2009-02-20 2011-12-28 Natural Medicine Institute Of Zhejiang Yangshengtang Co., Ltd. Mordant et composition de coloration des cheveux comprenant ledit mordant
EP2446876A1 (fr) 2009-06-24 2012-05-02 Natural Medicine Institute Of Zhejiang Yangshengtang Co., Ltd. Colorant capillaire, association formant un produit capillaire colorant et son procédé d'utilisation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7749286B2 (en) * 2006-05-01 2010-07-06 Advanced Cosmetic Technologies, Llc Composition for dyeing keratin fibers and a method of dyeing hair using same
JP5586939B2 (ja) * 2009-12-21 2014-09-10 富士フイルム株式会社 染毛剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0327345A2 (fr) 1988-02-04 1989-08-09 Wella Aktiengesellschaft Composition pour rendre plus foncé les cheveux
EP0394930A1 (fr) 1989-04-24 1990-10-31 Kao Corporation Composition pour le traitement des cheveux, composition pour décolorer les cheveux et composition pour modifier la teinte des cheveux
JPH04208214A (ja) 1990-11-30 1992-07-29 Seiho Kikaku Kk 頭髪用染毛剤及びその製造方法並びにその染毛方法
EP2399567A1 (fr) 2009-02-20 2011-12-28 Natural Medicine Institute Of Zhejiang Yangshengtang Co., Ltd. Mordant et composition de coloration des cheveux comprenant ledit mordant
EP2446876A1 (fr) 2009-06-24 2012-05-02 Natural Medicine Institute Of Zhejiang Yangshengtang Co., Ltd. Colorant capillaire, association formant un produit capillaire colorant et son procédé d'utilisation

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016216457A (ja) * 2015-05-18 2016-12-22 フロムファーイースト株式会社 毛髪化粧料組成物、毛髪化粧料及び染毛方法
US20180345048A1 (en) * 2017-06-05 2018-12-06 Momentive Performance Materials Inc. Composition and method for strengthening hair fiber
US10556133B2 (en) * 2017-06-05 2020-02-11 Momentive Performance Materials Inc. Composition and method for strengthening hair fiber
EP3856133A1 (fr) * 2018-09-24 2021-08-04 Henkel AG & Co. KGaA Endommagement réduit des cheveux pendant la décoloration au moyen d'un agent complexant biodégradable
WO2020064269A1 (fr) * 2018-09-25 2020-04-02 Henkel Ag & Co. Kgaa Endommagement réduit des cheveux pendant la décoloration au moyen d'un agent complexant biodégradable
US11426335B2 (en) 2018-09-25 2022-08-30 Henkel Ag & Co. Kgaa Reduced hair damage during blonding through use of a biodegradable complex former

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Publication number Publication date
WO2013167350A3 (fr) 2014-06-26

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