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WO2004045567A1 - Utilisation de derives d'acide ascorbique dans des produits de soin capillaire - Google Patents

Utilisation de derives d'acide ascorbique dans des produits de soin capillaire Download PDF

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Publication number
WO2004045567A1
WO2004045567A1 PCT/EP2003/010472 EP0310472W WO2004045567A1 WO 2004045567 A1 WO2004045567 A1 WO 2004045567A1 EP 0310472 W EP0310472 W EP 0310472W WO 2004045567 A1 WO2004045567 A1 WO 2004045567A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
ascorbic acid
hair care
acid derivative
care product
Prior art date
Application number
PCT/EP2003/010472
Other languages
English (en)
Inventor
Philippe Emmanuel Maillan
Horst Westenfelder
Michael Weller
Original Assignee
Dsm Ip Assets B.V.
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 Dsm Ip Assets B.V. filed Critical Dsm Ip Assets B.V.
Priority to AU2003270228A priority Critical patent/AU2003270228A1/en
Publication of WO2004045567A1 publication Critical patent/WO2004045567A1/fr

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Classifications

    • 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
    • A61Q5/004—Preparations used to protect coloured hair
    • 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
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to a novel use of ascorbic acid derivatives in hair care products.
  • the treatment of artificially coloured hair with hair care products containing an ascorbic acid derivative results in protection and stabilisation of the colour of the hair.
  • the present invention in one aspect, relates to the use of ascorbic acid derivatives in the manufacture of hair care products for protecting and stabilizing artificially coloured hair, particularly against the impact of actinic radiation.
  • the invention in another aspect, relates to a method of protecting and stabilizing the colour of artificially coloured hair, particularly against the impact of actinic radiation, by treatment of such hair with a hair care product containing an ascorbic acid derivative.
  • artificially coloured hair denotes hair that has been coloured by any method of dyeing hair, e.g.by oxidative dyeing or by semi-permanent dyeing.
  • hair care product denotes any conventional hair care product, such as shampoos, conditioners, tonics, styling gels, mousses, hair sprays, pomades, setting lotions, colouring and permanent waving compositions.
  • shampoos, tonics and conditioners Of particular interest for the purpose of the present invention are shampoos, tonics and conditioners.
  • ascorbic acid derivative as used in accordance with the present invention may by any non-toxic, non skin-irritating water-soluble or oil-soluble ascorbic acid derivative.
  • oil soluble derivatives are ascorbic acid esters of long-chain fatty acids such as ascorbyl palmitate, ascorbyl tetraisopalmitate, ascorbyl linoleate, ascorbyl octanoate,
  • water soluble ascorbyl derivatives such as sodium ascorbyl phosphate, magnesium ascorbyl phosphate and ascorbyl glycoside. Most preferred is sodium ascorbyl phosphate.
  • the amount of ascorbic acid derivative in the hair care product for use in accordance with the present invention is suitably in the range from about 0.0001 wt.-% to about 10 wt.-%, preferably from about 0.01 wt.-% to about 5 wt.-%, and most preferably from about 0.1 wt.-% to about 3 wt.-%.
  • the ascorbic acid derivative may be incorporated in hair care products by adding it to the final formulation or at any appropriate intermediate step in the manufacture of said products.
  • the ascorbyl phosphate is used in combination with one or more agents selected from UV screening agents, vitamin A or derivatives thereof, vitamin E or derivatives thereof, a vitamin from the B complex, panthenol, phytantriol or derivatives thereof.
  • UV screening agent means a compound or composition that absorbs UV radiation in the range of about 320 nm to about 400 nm (UV-A) or in the range of about 280 nm to about 320 nm (UV-B).
  • UV filters include, for example, dibenzoylmethane derivatives such as butyl methoxydibenzoylmethane (PARSOL 1789), benzylidene- cyanoacetates such as 4-methoxy-benzylidene-cyanoacetic acid n-hexyl ester, triazine derivatives such as 4,4'-(6-(bis(2-ethyl-hexyl)-amino)-s-triazine-2,4-diyl)-diresorcinol, anilinomethylene derivatives such as 2-(4-ethoxy-anilinomethylene)-propanedioic acid diethyl ester, camphor derivatives sich as 4-methyl benzylidene
  • the UV-A filter is selected from the group consisting of PARSOL 1789, 4,4'-(6-(bis(2-ethyl-hexyl)-amino)-s- triazine-2,4-diyl)-diresorcinol (Triazin), 2-(4-ethoxy-anilinomethylene)-propanedioic acid diethyl ester, and mixtures thereof, PARSOL MCX or PARSOL SLX.
  • UV filters for use in the present invention are :
  • a 0, 1 or 2
  • R 1 is hydrogen, a saturated or unsaturated CrC 30 hydrocarbon group or a trimethylsilyloxy group
  • Z is an amino substituted hydroxybenzophenone of the formula
  • R and R independently are hydrogen, Cr nalkyl, C -C 2 oalkenyl, C 3 -C ⁇ ocycloalkyl or Cs- ocycloalkenyl or R and R , together with the nitrogen atom they are bound to, form a 5 to 6 membered ring;
  • X is -O- or -NR 5 - wherein R 5 is hydrogen, C 1 -C 20 alkyl, C 2 -C 2 oalkenyl, C 3 -C ⁇ ocycloalkyl or C 3 -C ⁇ ocycloalkenyl; and
  • Y is a divalent C 3 -C 12 alkylene or alkenylene chain
  • b 0, 1, 2, 3;
  • R is hydrogen, a saturated or unsaturated -C 3 ohydrocarbon group or a trimethylsilyloxy group
  • R and R are identical or different electron-withdrawing groups, or one of R and R is hydrogen and the other of R 1 and R 2 is an electron-withdrawing group;
  • R 3 , R 4 , R 5 , are R 6 are, independently, hydrogen, alkyl or aryl;
  • R 3 and R 5 and/ or R 4 , and R 6 taken together with the carbon atoms to which they are attached, may form a 5 or 6 membered ring which optionally is substituted with one to four alkyl or alkoxy groups;
  • X is a moiety R 7 , when m is 1; and is alkylene or poly(oxyalkylene) when m is 2; and
  • R 7 is hydrogen, alkyl, alkoxyalkyl or aryl; and
  • R 1 and R 2 are, independently from each other, hydrogen; halogen; hydroxy; ( - o)- alkyl; (C 2 -C 2 o)-alkenyl; or (C ⁇ -C 2 o)-alkoxy;
  • X is oxygen or an imino group, optionally substituted with R 1 ;
  • R 3 and R 4 are, independently from each other, cyano; -COOR 5 ; -COR 6 ; -CONH 2 ; -CONHR 7 ; or -CONR 8 R 9 ;
  • R 5 , R 6 , R 7 , R 8 and R 9 are, independently from each other, hydrogen; (C 1 -C 2 o)-alkyl, wherein one or more methylene groups are optionally replaced by one or more oxygens;
  • Prefered UV filters are PARSOL SLX and PARSOL 1789.
  • the sunscreens agents may be present in the hair care products in an amount from about 0.01 wt.-% to about 5.0 wt.-%.
  • a vitamin A derivative for use in the present invention is, e.g. a fatty acid ester such as vitamin A acetate or palmitate which may be present in the hair care products in an amount from about 0.01 wt.-% to about 1.00 wt.-%.
  • a vitamin E derivative for use in the present invention is, e.g. tocopheryl acetate. Tocopheryl acetate may be present in the hair care products in an amount from about 0.05 wt.-% to about 5 wt.-%.
  • vitamins from the B complex for use in the present invention are vitamin B 2 , B 6 and biotin. Vitamin B 2 may be present in the hair care products in an amount from about 0.01 wt.-% to about 1.00 wt.-%.
  • Vitamin B 6 may be present in the hair care products in an amount from about 0.01 wt-% to about 1.00 wt.-%.
  • Biotin may be present in the hair care products in an amount from about 0.001wt.-% to about 0.5 wt.-%.
  • Panthenol may be present in the hair care products in an amount from about 0.05 wt.-% to about 5.00 wt- %.
  • Phytantriol may be present in the hair care products in an amount from about 0.01 wt- % to about 2.5 wt.-%.
  • the hair care products comprising an ascorbic acid derivative may be, otherwise, of conventional composition such as disclosed in general terms in Ullmann's Encyclopedia of Industrial Chemistry (1989), Vol A 12, Hair Preparations, and more specifically, e.g., in International Patent Application No. WO 00/06094, WO 00/07550 and WO 01/06994, the contents of which are incorporated herein for reference.
  • a hair shampoo is any composition that contains at least one surfactant suitable for cleaning hair, such as for example, the shampoo compositions set forth in the examples below.
  • the base ingredient of a shampoo composition is a water/anionic surfactant system that emulsifies the accumulated surface oils and removes them during the rinsing process.
  • Suitable anionic surfactants are Cio- 18 -alkyl ether sulfates, C 10 - ⁇ 8 -alkyl sulfates, sulfuric acid fatty alcohol esters and salts thereof like e.g. ammonium, sodium, potassium or mono-, di-or triethanolamine salts.
  • o-is -alkyl ether sulfates are sodium lauryl ether sulfate, potassium lauryl ether sulfate, ammonium lauryl ether sulfate.
  • examples of o-is -alkyl sulfates are sodium lauryl sulfate (Sodium Laureth Sulfate), potassium lauryl sulfate and ammonium lauryl sulfate.
  • Sodium Laureth Sulfate is available from Henkel under the tradenames TEXAPON N25 and TEXAPON N28.
  • anionic surfactants include ⁇ -olefin sulfonates, alkyl monoglyceride sulfonates, alkyl benzene sulfonates, alkyl sarcosinates, alkyl monoglyceride sulfates, monoalkylether sulfosuccinates, alkyl ether carboxylates and the like.
  • the anionic surfactant can be employed at concentrations within the range from about 5 to about 40 wt%, preferably about 15 wt%.
  • a "hair conditioner” is any composition that is used to restore the original condition of hair.
  • Such conditioners include, for example, silicones, cationic surfactants and quaternary ammonium compounds, and synthetic cationic polymers.
  • Other components for use in hair care compositions in accordance with the present invention include moisturizing agents, thickeners or viscosity modifying agents for enhancing hand application, lathering agents for increasing foaming, foam stabilizers, and pearlizing agents.
  • Examples of yet other components which are commonly included in hair care compositions are perfumes, pH control agents, colorants, preservatives, and antimicrobials.
  • the ascorbic acid derivative is used in combination with a cationic conditioning agents, e.g.
  • Polyquaternium those disclosed in International Patent Application WO 00/07550, particularly those referred to collectively as Polyquaternium, see Pharm Ind. 44, Nr. 6, 576-580 (1982) and Cosmetic, Toiletry, and Fragrance Association, CTFA, as well as International Patent Application WO 00/06094, WO 01/06994 e.g Polyquaternium 6, Polyquaternium 7, Polyquaternium 10, Polyquaternium 11, and Polyquaternium 16.
  • the Polyquaternium compounds maybe used, in addition to the ascorbic acid derivative, in amounts of about 0.01 to about 5.0 wt%.
  • hair swatches were submitted to a standard shampooing.
  • Group 1 of hair swatches was treated with a placebo hair tonic (formulation without Sodium Ascorbyl Phosphate) and group 2 of hair swatches was treated with a hair tonic containing 0.50%
  • Sodium Ascorbyl Phosphate STAY-C 50TM, Roche Vitamins AG, Basel. All six hair swatches were kept under standard climatic conditions for 1 week. The colour of the hair tresses was measured and specified according to the CIELAB system. The swatches were irradiated with artificial light with the help of a Weather- O meter 12 hours on each side. After totalizing 24h of irradiation, the swatches were removed from the irradiation chamber and the colour of the swatches was measured with the help of a colorimeter.
  • SAP Sodium Ascorbyl Phosphate
  • the initial depth of shade of the hair tress was: 4/0.
  • the hair were bleached with BLONDOR CREAM SPECIAL which was mixed in a ratio of 1:2 with a commercially available hydrogen peroxide formulation (with 6 % hydrogen peroxide).
  • the bleaching was performed for 30 min at room temperature.
  • a standard hair washing with lauryl ether sulfate was performed.
  • the hair swatches were dried under a hair drier for 30 min. A depth of shade of 6/0 was achieved for the bleached hair swatches.
  • the hair swatches were dyed with KOLESTON PERFECT 1+1 (7/64) which was mixed according to the recommendations of the manufacturer in a ratio 1 : 1 with a commercially available hydrogen peroxide formulation (9 % H 2 0 2 ). The dyeing was performed for 30 min at room temperature. Afterwards, the hair swatches were subjected to a standard hair washing with lauryl ether sulfate. The hair swatches were dried under a hair drier for 30 min. Conditioning of hair swatches
  • the six dyed hair swatches were stored for 7 days in the dark at standard atmosphere (20 + 2 °C, 65 ⁇ 2 % r. h.).
  • the colour of the hair swatches was measured by means of a Datacolor colorimeter 3890 (Datacolor GmbH, Marl) using the 10° observer and illuminant D65.
  • a special sample holder was used for the colour measurement of the hair swatches .
  • the hair swatches were put on the sample holder after thorough parallelisation and combing. In each case six measurements were performed for each swatch, three measurements on each side of the swatch.
  • the colour values of the hair swatches were calculated with the Datacolor formula which are based on ' the CIELAB system. The colour value; were subjected to statistical evaluation (confidence coefficient: 95 %).
  • the colour of the hair swatches was measured before the irradiation and after 24h of irradiation (12 h on each side of the hair swatch).
  • the irradiation was performed by means of an Atlas Weather- Ometer ES25 (Atlas, Chicago/USA) which is equipped with a water-cooled high-pressure xenon burner using the filter system inner filter: borosilicate, outer filter: soda lime.
  • the hair swatches were put into a special sample holder for irradiation. They were turned after 12 h of irradiation in order to obtain an even irradiation of the hair swatches. After 24 h of irradiation, the hair swatches were taken out of the irradiation chamber, stored for 2h in the dark at standard atmosphere and the colour of the hair swatches was measured as described above.
  • the irradiance was kept constant at 0.30 W/m 2 /nm (recorded at 340 nm with the help of a light monitor system).
  • a mean black standard temperature of 59.6 °C and an average relative humidity of 58.5 % were recorded.
  • the hair swatches underwent discoloration during exposure to simulated sunlight. After the irradiation time, less pronounced colour changes were analysed for hair swatches treated with the Sodium Ascorbyl Phosphate containing formulation than for hair which was treated with the placebo formulation. Most pronounced are the differences in the ⁇ a and ⁇ b values after the irradiation for placebo- and SAP-treated hair swatches.
  • Figure 1 shows the mean Colour differences ( ⁇ E, CIE L*a*b system) of bleached and dyed hair swatches which were treated with a hair tonic with STAY-C 50 or with a placebo during irradiation (in each case the mean colour values of three hair swatches are given).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne l'utilisation de dérivés d'acide ascorbique pour préparer des produits de soin capillaire afin de stabiliser la couleur de cheveux colorés artificiellement, notamment en les protégeant des effets du rayonnement actinique.
PCT/EP2003/010472 2002-11-19 2003-09-19 Utilisation de derives d'acide ascorbique dans des produits de soin capillaire WO2004045567A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003270228A AU2003270228A1 (en) 2002-11-19 2003-09-19 Use of ascorbic acid derivatives in hair care products

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP02025861.2 2002-11-19
EP02025861 2002-11-19

Publications (1)

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WO2004045567A1 true WO2004045567A1 (fr) 2004-06-03

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WO (1) WO2004045567A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1875890A3 (fr) * 2006-06-28 2008-06-04 Beiersdorf Aktiengesellschaft Shampoing capillaire soignant qui prolonge de manière mesurable la brillance et la fraîcheur de la couleur de fibres de kératine colorées
EP2018890A3 (fr) * 2007-07-17 2009-03-25 Johnson and Johnson Consumer Companies, Inc. Procédés de nettoyage de cheveux teints
WO2024206619A1 (fr) * 2023-03-31 2024-10-03 Colgate-Palmolive Company Compositions de soins personnels

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3337411A (en) * 1961-10-26 1967-08-22 Interpal S A Oxidation dyestuffs with ascorbic acid or salts thereof for dyeing living human hair
US5023235A (en) * 1987-02-09 1991-06-11 L'oreal Antioxidant system based on an ascorbyl ester in combination with a complexing agent and a thiol and to compositions containing the same
WO2001006997A1 (fr) * 1999-07-28 2001-02-01 The Boots Company Plc Composition pour soins capillaires
WO2001022924A1 (fr) * 1999-09-30 2001-04-05 The Boots Company Plc Composition de soin capillaire
WO2001030784A1 (fr) * 1999-10-26 2001-05-03 L'oreal Composes silicies derives de l'acide ascorbique
WO2002055041A2 (fr) * 2001-01-15 2002-07-18 Showa Denko K.K. Agent de traitement capillaire
WO2003017958A1 (fr) * 2001-08-27 2003-03-06 Mandom Corporation Colorant capillaire

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3337411A (en) * 1961-10-26 1967-08-22 Interpal S A Oxidation dyestuffs with ascorbic acid or salts thereof for dyeing living human hair
US5023235A (en) * 1987-02-09 1991-06-11 L'oreal Antioxidant system based on an ascorbyl ester in combination with a complexing agent and a thiol and to compositions containing the same
WO2001006997A1 (fr) * 1999-07-28 2001-02-01 The Boots Company Plc Composition pour soins capillaires
WO2001022924A1 (fr) * 1999-09-30 2001-04-05 The Boots Company Plc Composition de soin capillaire
WO2001030784A1 (fr) * 1999-10-26 2001-05-03 L'oreal Composes silicies derives de l'acide ascorbique
WO2002055041A2 (fr) * 2001-01-15 2002-07-18 Showa Denko K.K. Agent de traitement capillaire
WO2003017958A1 (fr) * 2001-08-27 2003-03-06 Mandom Corporation Colorant capillaire

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1875890A3 (fr) * 2006-06-28 2008-06-04 Beiersdorf Aktiengesellschaft Shampoing capillaire soignant qui prolonge de manière mesurable la brillance et la fraîcheur de la couleur de fibres de kératine colorées
EP2018890A3 (fr) * 2007-07-17 2009-03-25 Johnson and Johnson Consumer Companies, Inc. Procédés de nettoyage de cheveux teints
JP2009073812A (ja) * 2007-07-17 2009-04-09 Johnson & Johnson Consumer Co Inc 染色された毛髪を洗浄する方法
US7820608B2 (en) 2007-07-17 2010-10-26 Johnson & Johnson Consumer Companies, Inc. Methods of cleansing dyed hair
US8030262B2 (en) 2007-07-17 2011-10-04 Johnson & Johnson Consumer Companies, Inc. Methods of cleansing dyed hair
WO2024206619A1 (fr) * 2023-03-31 2024-10-03 Colgate-Palmolive Company Compositions de soins personnels

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