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WO2016097248A1 - Procédé de coloration de fibres de kératine à l'aide de henné pré-hydrolysé et décontaminé - Google Patents

Procédé de coloration de fibres de kératine à l'aide de henné pré-hydrolysé et décontaminé Download PDF

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Publication number
WO2016097248A1
WO2016097248A1 PCT/EP2015/080403 EP2015080403W WO2016097248A1 WO 2016097248 A1 WO2016097248 A1 WO 2016097248A1 EP 2015080403 W EP2015080403 W EP 2015080403W WO 2016097248 A1 WO2016097248 A1 WO 2016097248A1
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WIPO (PCT)
Prior art keywords
oil
henna
composition
mixture
minutes
Prior art date
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Ceased
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PCT/EP2015/080403
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English (en)
Inventor
Patrick Choisy
Emilie GUENAULT
Marion GABANT
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LOreal SA
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LOreal SA
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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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—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]
    • A61K8/9789—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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/81—Preparation or application process involves irradiation

Definitions

  • the subject of the invention is i) a process for preparing an aqueous composition comprising pre-hydrolysed and decontaminated henna, ii) the aqueous composition prepared according to the process, iii) a process for dyeing keratin fibres, in particular human keratin fibres, such as the hair, which uses the composition comprising pre-hydrolysed and decontaminated henna optionally extemporaneously with indigo, iv) the use of the composition comprising the prehydrolysed and decontaminated henna and optionally indigo prepared extemporaneously, for dyeing keratin fibres in a single action.
  • the first known as oxidation dyeing or permanent dyeing, consists in using one or more oxidation dye precursors, more particularly one or more oxidation bases optionally combined with one or more couplers.
  • Oxidation bases are usually chosen from ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds. These oxidation bases are colourless or weakly coloured compounds, which, when combined with oxidizing products, can give rise via a process of oxidative condensation to coloured species, which remain trapped within the fibre.
  • the shades obtained with these oxidation bases are often varied by combining them with one or more couplers, these couplers being chosen in particular from aromatic meta- diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds, such as indole compounds.
  • the second dyeing method comprises the application of direct dyes, which are coloured and colouring molecules that have affinity for fibres. Given the nature of the molecules used, they tend rather to remain on the surface of the fibre and penetrate relatively little into the fibre, when compared with the small molecules of oxidation dye precursors.
  • the main advantages of this type of dyeing are that it does not require any oxidizing agent, which limits the degradation of the fibres, and that it does not use any dyes that have particular reactivity, resulting in limitation of the intolerance risks.
  • the first hair dyes were semi-permanent.
  • One of the most well known natural dyes is that derived from the henna plant. Henna continues to be used in feminine beauty enhancement for colouring the hair or the nails, or for dyeing leather, silk and wool, etc. It is also used traditionally for various important events, celebrations and beliefs.
  • Red henna is constituted of leaves of shrubs of the genus Lawsonia from the family
  • Lythraceae which is based on the principle of dyeing with the active agent lawsone: 2- hydroxy-1 ,4-naphthoquinone. Lawsone [83-72-7] (CI Natural Orange 6 ; CI 75420), also known as isojuglone, may be found in henna shrubs (Lawsonia alba, Lawsonia inermis) ("Dyes, Natural", Kirk-Othmer Encyclopedia of Chemical Technology, "Henna” Encyclopedia Britannica).
  • This dye affords an orange-red colouration on grey hair, and a "warm” i.e. coppery to red colour on chestnut-brown hair.
  • the dyeing process using henna is difficult to perform.
  • a kind of "paste” (often referred to as a "poultice") is first made from ground or powdered henna leaves, which is then diluted at the time of use with warm water, and said paste is then applied to the keratin fibres.
  • henna powder generally contains between 10 5 and 10 6 bacteria per gram of leaves. In point of fact, it is preferable to have a henna powder quality with a very low bacterial content.
  • indigo Another very well-known natural dye is indigo (see Ullmann's Encyclopedia of Industrial Chemistry, Hair preparation, point 5.2.3, 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim; 10.1002/14356007.a12 571 .pub2).
  • Indigo continues to be used for feminine beauty enhancement by dyeing the hair or the nails, or for dyeing fabrics (jeans), leather, silk, wool, etc.
  • Indigo [482-89-3] is a natural dye, originating in particular from the indigo plant, and having the empirical formula: Ci 6 H 10 N 2 O2; and having the structure:
  • Indigo is derived from indican and may be prepared from various plants known as indigo-producing plants such as Indigofera tinctoria, Indigo suffruticosa, Isatis tinctoria, etc. (see Kirk-Othmer Encyclopedia of Chemical Technology, updated on 17/04/2009, DOI: 10.1002/0471238961.0425051903150618.a01.pub2).
  • the indigo-producing plants are generally chopped and soaked in hot water, heated, fermented and oxidized in the open air to liberate the purple-blue coloured indigo (see Chem. Rev. 201 1 , 111 , 2537-2561 , p. 2537- 2561 ).
  • Indigo is the result of the fermentation, in the presence of ⁇ -glucosidases, and then oxidization of indican (glycosyl precursor).
  • the indigo molecule is insoluble in water.
  • the current colourations with henna and derived from indigo-producing plant(s) are applied in the form of a poultice for a long leave-on time on the hair and are then rinsed out, and the hair is dried, generally in the open air without final shampooing, so as to allow the colouration to become oxidized in the course of the following hours or even days.
  • the oxidation time is more or less long, but is never instantaneous.
  • the result also varies as a function of the fibres to be dyed and of the indigo or henna raw material used.
  • a dyeing process in at least two steps; the first consists in dyeing the hair with henna, then removing the henna poultice, rinsing and optionally shampooing, rinsing again and drying, and then in dyeing the hair with indigo, removing the henna poultice and rinsing, and optionally shampooing, rinsing again, and drying.
  • This type of process is not therefore easy to carry out since it comprises several steps to be controlled, and the dyeing results obtained are not always satisfactory, in particular in terms of reproducibility of fundamental colours, strengths, and/or colour uniformity.
  • Another subject of the invention relates to an aqueous composition
  • an aqueous composition comprising pre- hydrolysed and decontaminated henna, said composition being prepared according to the preparation process as defined previously, preferably packaged under vacuum and/or under argon.
  • the composition is packaged in a sealed multilayer pouch, more particularly said pouch is constituted of polyethylene terephthalate (PET), polypropylene terephthalate (PPT) and/or polyamide imide (Al).
  • PET polyethylene terephthalate
  • PPT polypropylene terephthalate
  • Al polyamide imide
  • Another subject of the invention relates to a process for dyeing keratin fibres, in particular human keratin fibres, such as the hair, comprising:
  • said composition is left on said fibres for a period of between 15 minutes and 6 hours, preferably between 30 minutes and 2 hours, particularly at a temperature of between 20°C and 30°C, preferably for 1 hour at 27°C, followed by
  • composition according to the invention which comprises pre-hydrolysed and decontaminated henna, prepared according to the process of the invention, has the advantage of having very satisfactory colouring properties even though the henna has been decontaminated.
  • the same is true for the dyeing process using the composition according to the invention which makes it possible to obtain very effective colouring properties, despite the use of decontaminated henna and indigo.
  • the composition of the invention and the process for dyeing keratin fibres, in particular human keratin fibres, using this composition have the advantage of dyeing said fibres, with powerful, chromatic dyeing results that are resistant to washing, perspiration, sebum and light, and that are moreover long-lasting, without modifying said fibres.
  • the colourations obtained using the composition and the process for dyeing keratin fibres give uniform colours from the root to the end of a fibre (little colouration selectivity). Furthermore, the application of the composition of the invention, in particular the composition A as defined hereinafter, does not give off any raw-material dust (it is "dust- free”). In addition, the composition and the pre-hydrolysed henna active agent remain stable with respect to storage, in particular the composition A as defined hereinafter.
  • the keratin fibres treated have a very pleasant cosmetic aspect, and the integrity thereof is respected after treatment with the composition of the invention, and the dyeing process according to the invention.
  • the time devoted to dyeing using a natural product according to the process of the invention is shorter and the process is easier, without the need to keep a composition such as a poultice on the head for a long time (for several hours or even overnight) or to leave the composition (for example the poultice) to stand before application for a long time (several hours or several days), this being the case even though the henna used and optionally the indigo had been decontaminated. pre-hydrolysed henna
  • the dyeing process of the invention uses i) henna in powder form, particularly in fine particles.
  • the henna powder is different from an extract.
  • an extract is a product of maceration in aqueous or organic solvents
  • the powder according to the invention is a pure natural product originating from henna plants, reduced by grinding or other mechanical means, into fine particles.
  • the henna used in the process is in a composition in an amount of at least
  • the henna used in the invention is preferably red henna (Lawsonia inermis, alba).
  • the henna powder may be screened to obtain particles with upper limit sizes corresponding to the orifices or mesh sizes of the screen particularly between 35 and 80 mesh (US).
  • the size of the henna powder particles is fine. According to the invention, a particle size of less than or equal to 500 ⁇ is more particularly intended.
  • the powder is constituted of fine particles with sizes inclusively between 50 and 300 ⁇ and more particularly between 10 and 200 ⁇ . It is understood that said henna particles preferentially have a moisture content of between 0 and 10% by weight, relative to the total weight of the powders.
  • said henna particles are derived from henna leaves.
  • the henna of the invention is pre-hydrolysed.
  • pre-hydrolysed henna is intended to mean that the henna powder or the henna leaves have been hydrolysed beforehand according to conventional hydrolysis methods known to those skilled in the art.
  • the process for preparing the aqueous composition comprising pre-hydrolysed henna consists, according to the invention, in 1 ) the first step, in mixing i) henna powder with ii) an aqueous medium.
  • the pre-hydrolysed henna is prepared by leaving the henna powder i) in an aqueous medium ii) comprising predominantly water; preferably, the water used is demineralized or distilled.
  • the water included in the mixture with the henna is in an amount of between 30% and 95%, more preferentially between 50% and 90%, better still between 60% and 80% by weight relative to the total weight of the mixture.
  • the henna is in an acidic medium at a pH of between 3.5 and
  • Organic or inorganic acids may be added thereto. According to one preferred embodiment, no acid is added to the henna.
  • the henna i) is in the aqueous medium ii) as defined previously in an amount of between 1 % and 50%, more particularly of between 10% and 40%, preferably between 20% and 30% by weight relative to the total weight of the mixture.
  • the mixture of step 1 ) also contains one or more fatty substances as defined hereinafter.
  • the mixture of step 1 ) also comprises one or more adjuvants as defined hereinafter, preferably chosen from polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, hexylene glycol, and glycerol, more particularly glycerol, preferably in an amount of between 0.01 % and 20%, preferably between 0.05% and 15%, better still between 2% and 10% by weight relative to the total weight of the mixture of henna and aqueous medium.
  • adjuvants as defined hereinafter, preferably chosen from polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, hexylene glycol, and glycerol, more particularly glycerol, preferably
  • the mixture of step 1 does not comprise indigo.
  • the mixture of henna i) and aqueous medium ii) of step 1 ) is left:
  • the mixture of henna i) and aqueous medium ii) of step 1 ) is left stirring at a rotational speed of between 1 and 400 revolutions / minute, preferably between 50 and 200 revolutions / minute and more particularly between 70 and 150 revolutions / minute, such as 100 revolutions / minute.
  • the stirring is carried out in a mixer-grinder.
  • the mixture of henna i) and aqueous medium ii) of step 1 ) is left in a deflocculating mixer at a rotational speed of between 200 and 1500 revolutions / minute, particularly between 300 and 1000 revolutions / minute, more particularly between 500 and 950 revolutions / minute, preferentially between 700 and 900 revolutions / minute.
  • the deflocculation is carried out in a mixer-grinder.
  • the mixture of henna and aqueous medium as described previously can subsequently be placed under vacuum, and/or vacuum-packaged, and 2) can undergo decontamination as defined hereinafter in order to produce a composition A comprising henna.
  • the placing under vacuum and/or the vacuum-packaging can be carried out in particular at a pressure of between 5 and 400 mb, more particularly between 10 and 300 mb, preferentially between 20 and 200 mb, for a period of time of particularly between 5 seconds and 5 minutes, more particularly between 30 seconds and 3 minutes, preferentially between 45 seconds and 1 minute.
  • the packaging is preferably carried out in sealed multilayer pouches under vacuum; in particular, the pouches are constituted of polyethylene terephthalate (PET), polypropylene terephthalate (PPT) and/or polyamide imide (Al).
  • the preparation process of the invention which comprises pre-hydrolysed and decontaminated henna consists:
  • the mixture is left under vacuum and/or under an inert atmosphere such as nitrogen or argon for between 1 hour and 48 hours, in particular between 2 hours and 24 hours, at a temperature of between 4°C and 45°C, preferentially 2 to 6 hours at a temperature between 20 and 40°C, even more preferentially 6 hours at ambient temperature.
  • an inert atmosphere such as nitrogen or argon
  • the pre-hydrolysed henna in particular the composition A as defined previously and 2) as defined hereinafter, can be stored at ambient temperature (25°C) or in the cold, in particular at a temperature between 4 and 10°C.
  • composition A as defined previously is not packaged with indigo.
  • Decontamination method :
  • the second step which follows the hydrolysis of the henna is 2) the decontamination step.
  • This decontamination can also be applied to the indigo.
  • decontamination is intended to mean any process known to those skilled in the art which makes it possible to reduce the number of microbes, i.e. by a factor of 10 2 to
  • microbes is intended to mean microorganisms and in particular fungi, moulds, spores and bacteria.
  • the number of microorganisms is on average between 10 5 and 10 7 microorganisms per gram of powder or of leaves.
  • the decontamination is carried out a) by pasteurization or heat-controlled debacterialization.
  • pasteurization is intended to mean the method known to those skilled in the art, developed by Louis Pasteur, see for example http://fr.wikipedia.org/wiki/Pasteurisation.
  • the process of the invention uses a pasteurization termed
  • the mixture of pre-hydrolysed henna and aqueous medium is subjected to a temperature of between 70°C and 75°C, more particularly at 72°C, for a short period of time, preferably of between 10 seconds and 30 seconds, such as 15 seconds
  • the process of the invention uses a pasteurization termed "low”, i.e. at a temperature which is between 62°C and 67°C, more particularly at 65°C.
  • the mixture of pre-hydrolysed henna and aqueous medium is subjected to a temperature of between 62°C and 67°C, more particularly at 65°C, for a period of between 2 minutes and 5 minutes, preferably 3 minutes, and then is left to cool to ambient temperature.
  • the decontamination is carried out b) by sterilization, i.e. by applying to the mixture of pre-hydrolysed henna and aqueous medium, a temperature greater than or equal to 100°C, preferably by applying steam at a temperature in particular of between 100°C and 180°C, more particularly between 100°C and 125°C.
  • the decontamination process is carried out by c) the method known to those skilled in the art termed "appertization".
  • the mixture of pre-hydrolysed henna and aqueous medium of the process of the invention is packaged in a hermetically closed container which is subjected to a temperature of between 100 and 150°C, more particularly between 1 10 and 120°C.
  • the mixture of pre-hydrolysed henna and aqueous medium remains at this temperature particularly for between 1 minute and 2 hours, more particularly between 5 minutes and 1 hour, preferentially between 6 minutes and 30 minutes, and then is left to cool to ambient temperature.
  • the decontamination process is carried out by d) the method known to those skilled in the art termed "tyndallization".
  • the mixture of pre-hydrolysed henna and aqueous medium of the process of the invention is heated batchwise at low temperature. More particularly, the mixture is heated at a temperature between 40 and 70°C, preferentially at a temperature of between 45 and 60°C, for a period of between 15 minutes and 1 hour, preferably for 30 minutes, and then the mixture is left to cool to ambient temperature. This cycle is repeated every 24 hours.
  • the number of heating cycles applied to the mixture of pre-hydrolysed henna and aqueous medium is included inclusively between 1 and 20, preferably between 2 and 10, in particular 5 cycles.
  • the mixture of pre-hydrolysed henna and aqueous medium is subjected to e-i) steam at a temperature greater than 100°C.
  • This method can be carried out under a pressure higher than atmospheric pressure, in which case an autoclave and e) the method termed "autoclaving" will be used.
  • autoclave is intended to mean a container or receptacle, which has thick walls and which can be hermetically closed, designed to perform vapour sterilization under pressure (of a few bar), in which case the sterilizing agent is saturated steam under pressure or superheated water.
  • the value D or "decimal reduction time” is a thermal characteristic of the microorganism. It represents the time required, at a given temperature, for 90% reduction of the population of said microorganisms (or for reduction by 1 logarithm). For example, for G. stearothermophilus, the reduction time D at 121 °C is 1 .5 minutes.
  • the value Z or "heat inactivation value” is the change in temperature required to reduce the value of D by one logarithm.
  • the heat inactivation value Z is 10°C.
  • the value F 0 or "sterilizing value” is the number of minutes required to kill a given number of microorganisms of which the value Z is 10°C at a temperature of 121.1 °C.
  • the value F is the number of minutes required to kill a given number of microorganisms with a value Z at a certain temperature.
  • microorganisms For example, mention may be made of the following microorganisms:
  • the Sterility Assurance Level probability of survival of a microorganism after the sterilization process, this degree generally being fixed between 10 "5 and 10 "6 , which means a probability of less than one microorganism in 1000 or in 1 million after decontamination.
  • the "Overkill Approach” is required; when choosing a heat-resistant bacterial strain or spores at a load of 10 "6 , the value D of which at 121.1 °C is between 2 and 2.5 minutes, the reduction required is then 30 minutes. At 121 .1 °C, 30 minutes will be required in order to sterilize a load of 10 6 microorganisms with a probability of one microorganism in one million after the sterilization cycle.
  • the sterilizing value F 0 applied to the henna or indigo according to the invention is between 1 minute and 30 minutes, at 121 .1 °C, more particularly between 2 minutes and 20 minutes, at 121.1 °C, preferentially between 5 minutes and 10 minutes at 121.1 °C, better still F 0 is 6 minutes at 121 °C, which is equivalent to 20 minutes at 1 10°C.
  • the sterilization process is carried out in one or more cycles of 4 steps:
  • the pressure and temperature sterilization values are defined according to the Regnault table.
  • the number of cycles is included inclusively between 1 and 20, preferably between 2 and 10, in particular 3 cycles.
  • step i) is preceded by a step which consists of a succession of vacuum-applying operations and of steam injections in order to increase effectiveness of the sterilization stationary phase by removing the air contained in the sterilization chamber and in the load to be sterilized.
  • the mixture of pre-hydrolysed henna and aqueous medium of the process of the invention is i) heated at a temperature of between 120 and 150°C, more particularly at 134°C, at a pressure of between 2 and 4 bar, more particularly at a pressure of 2.2 bar, ii) for a period of between 5 minutes and 1 hour, more particularly between 10 minutes and 25 minutes, such as for 18 min, this being over the entire area to be sterilized, iii) followed by cooling to ambient temperature and iv) decreasing the pressure to atmospheric pressure.
  • the number of cycles is included inclusively between 1 and 10, preferably between 2 and 5, in particular 3 cycles.
  • the mixture of pre-hydrolysed henna and aqueous medium is decontaminated by f) the method known to those skilled in the art termed "pascalization". More particularly, the mixture of pre-hydrolysed henna and aqueous medium of the process undergoes a treatment at very high pressure or "ultrapressure" preferentially of between 1000 and 8000 bar, more preferentially between 2000 and 6000 bar, better still between 3000 and 5000 bar, such as 4000 bar. According to one particular embodiment , the duration of the pascalization cycle is between 5 minutes and 1 hour.
  • the mixture of pre-hydrolysed henna and aqueous medium is decontaminated by g) "ionizing radiation".
  • Ionizing radiation is also known under the following terms: “gamma-radiation”, “cold pasteurization” or “radioconversion” of the products to be decontaminated.
  • the mixture of pre-hydrolysed henna and aqueous medium must be irradiated for a period of time sufficiently long for the microorganisms (bacteria and moulds) targeted to be inactivated.
  • the mixture of pre-hydrolysed henna and aqueous medium is irradiated by the "radappertization" method known to those skilled in the art.
  • the irradiation is carried out on the mixture of pre-hydrolysed henna and aqueous medium at a dose of inclusively between 10 and 50 kilo Gray (KGy), preferentially between 12 and 30 KGy.
  • the mixture of pre-hydrolysed henna and aqueous medium is irradiated by the "radicidation" method known to those skilled in the art.
  • the irradiation is carried out on the mixture of pre-hydrolysed henna and aqueous medium at a dose of inclusively between 1 .8 and 18 KGy, preferentially between 2 and 15, better still between 5 and 8 KGy.
  • the mixture of pre-hydrolysed henna and aqueous medium is irradiated by the "radurization" method known to those skilled in the art.
  • the irradiation is carried out on the mixture of pre-hydrolysed henna and aqueous medium at a dose of less than or equal to 1 , preferably of between 0.4 and 1 KGy.
  • the decontamination 2) is carried out according to the pasteurization, sterilization, gamma-irradiation, or pascalization techniques.
  • the decontamination 2) is carried out under steam at a temperature of greater than 100°C, particularly at a temperature of greater than 1 10°C, preferably at a temperature of between 1 15°C and 150°C.
  • the sterilization is carried out 2) for a period of between 1 minute and 1 hour, more particularly between 10 minutes and 40 minutes, preferentially between 15 minutes and 30 minutes.
  • the decontamination of the mixture of pre- hydrolysed henna and aqueous medium is carried out by gamma-irradiation at a dose of between 5 and 15 KGy, preferably around 12 KGy.
  • composition comprising the pre-hydrolysed henna and ready-to-use composition comprising pre-hydrolysed henna and indigo:
  • a subject of the invention is also a composition
  • a composition comprising pre-hydrolysed henna, resulting from the preparation process as defined previously, preferably the composition A as defined previously, optionally comprising one or more fatty substances, which are preferably liquid at ambient temperature, and optionally one or more adjuvants chosen from polyols.
  • the composition contains between 1 % and 40% by weight of pre- hydrolysed and decontaminated henna, between 0 and 15% by weight of fatty substance, which is in particular liquid at ambient temperature and at atmospheric pressure, such as copra oil, between 0 and 10% by weight of polyols, and qs % by weight of demineralized or distilled water per 100 grams of composition.
  • Another subject of the invention is a ready-to-use composition, i.e. a composition prepared just before application to the keratin fibres, preferably between 1 second and 20 minutes, such as 5 minutes, before application to the keratin fibres, from the mixing of a composition comprising pre-hydrolysed henna, resulting from the preparation process as defined previously, preferably using the composition A as defined previously, and of a composition B comprising indigo which is non-decontaminated or which has been decontaminated according to any one of the techniques a) to f) as defined previously.
  • the process for dyeing keratin fibres of the invention also uses a composition B which comprises indigo, in particular indigo- producing plant powder, preferably in fine particles.
  • the indigo-producing plant powder is different from an extract.
  • an extract is a product of maceration in solvents, generally organic solvents
  • the powder according to the invention is a pure natural product originating from indigo-producing plants, reduced by grinding or other mechanical means, into fine particles.
  • the composition B comprises at least 10% by weight of indigo-producing plants powder relative to the total weight of the composition.
  • Indigofera such as Indigofera tinctoria, Indigo suffruticosa, Indigofera articulata,
  • Isatis such as Isatis tinctoria
  • Persicaria such as Polygonum tinctorium (Persicaria tinctoria);
  • Calanthe such as Calanthe veratrifolia
  • Baphicacanthus such as Baphicacanthus cusia.
  • the indigo-producing plant is of the genus Indigofera and more particularly is Indigofera tinctoria.
  • Use may be made of all or part (in particular the leaves in particular for Indigofera tinctoria) of the indigo-producing plant.
  • the indigo-producing plant powder may be screened to obtain particles with upper limit sizes corresponding to the orifices or mesh sizes of the screen particularly between 35 and 80 mesh (US).
  • the size of the indigo-producing plant powder particles is fine. According to the invention, a particle size of less than or equal to 500 ⁇ is more particularly intended. Preferentially, the powder is constituted of fine particles with sizes inclusively between 50 and 300 ⁇ and more particularly between 10 and 200 m.
  • said indigo-producing plant particles preferentially have a moisture content of between 0 and 10% by weight relative to the total weight of the powders.
  • composition B according to the invention comprises indigo-producing plant powder in an amount particularly inclusively between 10% and 90% by weight, more particularly between 15% and 70%, or even between 20% and 60% by weight and more particularly between 25% and 50% by weight, relative to the total weight of said composition.
  • Another subject of the invention is a process for dyeing keratin fibres, in particular human keratin fibres, such as the hair, comprising:
  • the composition is left on the keratin fibres for a period of between 15 minutes and 3 hours, preferably between 30 minutes and 2 hours, preferably for 1 hour.
  • the step of applying the composition of the invention is carried out at a temperature between 20°C and 30°C, such as 27°C.
  • the time during which the composition of the invention is left on the keratin fibres is 1 hour at 27°C.
  • a first variant of the process of dyeing keratin fibres of the invention consists in applying, to the keratin fibres, a composition comprising pre-hydrolysed and decontaminated henna, in particular A as defined previously.
  • a second variant of the process for dyeing keratin fibres of the invention consists in applying, to the keratin fibres, the ready-to-use composition as defined previously, which results from mixing between a composition comprising pre-hydrolysed and decontaminated henna, and in particular the composition A, and a composition B comprising indigo as defined previously, the indigo being non-decontaminated or decontaminated according to any one of the techniques a) to f) as defined previously; in particular, B is in the form of a poultice.
  • the ready-to-use composition comprises a mixture of henna powder and indigo-producing plant powder in an amount particularly inclusively between 15% and 100% by weight, more particularly between 20% and 80%, or even between 25% and 70% by weight and more particularly between 25% and 60% by weight, relative to the total weight of said ready-to-use composition.
  • the composition A as defined previously also comprises indigo-producing plant powder, preferably in fine particles, as defined previously, and in amounts as defined for the ready-to-use composition.
  • the composition A as defined previously is not packaged with indigo.
  • the process comprises:
  • composition comprising pre-hydrolysed and decontaminated henna as defined previously;
  • composition B comprising indigo-producing plant powder as defined hereinafter;
  • compositions are left on said fibres for a period of between 15 minutes and 3 hours, preferably between 30 minutes and 2 hours, particularly at a temperature of between 20°C and 30°C, preferably for 1 hour at 27°C, followed by
  • the amount of indigo-producing plant powder of the composition B is greater than 10% by weight, more particularly inclusively between 10% and 90% by weight, even more particularly between 15% and 70%, preferentially between 20% and 60% by weight, more preferentially between 25% and 50% by weight, relative to the total weight of the composition B.
  • the weight ratio of henna powder and of indigo-producing plant powder after mixing preferably ranges from 95% to 5% of henna powder per 5% to 95% of indigo-producing plant powder, particularly from 75% to 25% of henna powder per 25% to 75% of indigo-producing plant powder, and more particularly from 55% to 45% of henna powder per 45% to 55% of indigo-producing plant powder by weight relative to the total weight of the mixture, in particular of the mixture of the two compositions A and B.
  • a mixture of 50% henna powder and 50% indigo-producing plant powder is particularly appreciated.
  • a third variant of the process for dyeing keratin fibres of the invention consists in applying, to the keratin fibres, the composition A which also comprises indigo-producing plant powder as defined previously.
  • the composition i) comprising pre-hydrolysed and decontaminated henna as defined previously does not comprise indigo.
  • the dyeing process of the invention preferentially uses amounts of henna powder and of indigo which observe the henna powder / indigo-producing plant powder weight ratio inclusively between 80 / 20 and 75 / 25, particularly between 75 / 25 and 45 / 65, preferentially between 70 / 30 and 40 / 60.
  • the composition B is in the form of a poultice as defined previously.
  • the composition B is not decontaminated, it is used as it is with henna originating from an indigo-producing plant without it having been subjected to a decontamination step a) to f) as defined previously.
  • the composition B is decontaminated according to any one of the decontamination methods a) to f) as defined previously.
  • the decontamination of the composition B is carried out under steam at a temperature of greater than 100°C, particularly at a temperature of greater than 1 10°C, preferably at a temperature of between 1 15°C and 150°C, in particular by sterilization.
  • the time during which the indigo is subjected to steam is between 1 minute and 1 hour, more particularly between 10 minutes and 40 minutes, preferentially between 15 minutes and 30 minutes.
  • the decontamination of the composition B is carried out by g) ionizing radiation, i.e. particularly by the "radappertization" method, preferably the irradiation is carried out on the composition B at a dose inclusively between 20 and 50 KGy, more preferentially between 25 and 30 KGy.
  • the keratin fibres are, after the application of the decontaminated composition comprising the pre-hydrolysed henna, in particular the composition A, and/or after the application of the composition B as defined previously:
  • the application temperature of the decontaminated composition comprising the pre-hydrolysed henna, in particular the composition A and/or of the composition B ranges from ambient temperature (15 to 25°C) to 80°C and more particularly from 15 to 45°C.
  • the head of hair may advantageously be subjected to a heat treatment by heating to a temperature ranging from 30 to 60°C.
  • this operation may be performed using a styling hood, a hairdryer, an infrared ray dispenser or other standard heating appliances.
  • the dyeing process uses the following steps:
  • a basic composition preferably comprising sodium bicarbonate or potassium bicarbonate, a thickener such as hydroxyethylcellulose, and deionized or demineralized or distilled water, said composition being left on for a period of between 10 and 40 minutes, preferably between 15 and 30 minutes, followed by rinsing with water and optionally by maintaining the head of hair under a plastic film;
  • the proportions of the pre-hydrolysed henna/indigo mixture, calculated in terms of solids, are 80/20 to 20/80, preferentially 75/25 to 45/65, more preferentially 70/30 to 40/60 (limits included).
  • the keratin fibres after the dyeing step are not shampooed for 24 hours.
  • the dyeing process uses the following steps:
  • a basic composition preferably comprising sodium bicarbonate or potassium bicarbonate, a thickener such as hydroxyethylcellulose, and deionized or demineralized or distilled water, said composition being left on for a period of between 10 and 40 minutes, preferably between 15 and 30 minutes, followed by rinsing with water and optionally by maintaining the head of hair under a plastic film;
  • the proportions of the pre-hydrolysed henna/indigo mixture, calculated in terms of solids, are 80/20 to 20/80, preferentially 75/25 to 45/65, more preferentially 70/30 to 40/60 (limits included).
  • the dyeing process uses the following steps:
  • a basic composition preferably comprising sodium bicarbonate or potassium bicarbonate, a thickener such as hydroxyethylcellulose, and deionized or demineralized or distilled water, said composition being left on for a period of between 10 and 40 minutes, preferably between 15 and 30 minutes, followed by rinsing with water and optionally by maintaining the head of hair under a plastic film;
  • the proportions of the pre-hydrolysed henna/indigo mixture, calculated in terms of solids, are 80/20 to 20/80, preferentially 75/25 to 45/65, more preferentially 70/30 to 40/60 (limits included).
  • the keratin fibres after the dyeing step are not shampooed for 24 hours.
  • Use may be made, both as means for heating and straightening the head of hair, of a heating iron at a temperature ranging from 60°C to 220°C and preferably from 120°C to 200°C.
  • compositions comprising the pre-hydrolysed henna and the indigo in particular the compositions A and/or B, as defined previously, or a mixture thereof, also comprise the ingredient a) one or more fatty substances, which may be identical or different.
  • fatty substance is intended to mean an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1 % and even more preferentially less than 0.1 %). They bear in their structure at least one hydrocarbon-based chain comprising at least 6 carbon atoms or a sequence of at least two siloxane groups.
  • the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF), liquid petroleum jelly or decamethylcyclopentasiloxane.
  • compositions comprising the pre-hydrolysed henna and the indigo in particular the compositions A and/or B, as defined previously, or a mixture thereof, comprise a) one or more oils, which may be identical or different.
  • o/T is intended to mean a "fatty substance" as defined previously that is liquid at ambient temperature (25°C) and at atmospheric pressure (760 mmHg); the viscosity at 25°C is preferably less than 1200 cps and better still less than 500 cps (defined, for example, from the Newtonian plateau determined using an ARG2 rheometer from TA Instruments equipped with a spindle with cone-plate geometry 60 mm in diameter and with an angle of 2 degrees over a shear stress range of from 0.1 Pa to 100 Pa).
  • non-silicone o/T is intended to mean an oil not containing any silicon atoms (Si) and the term “silicone o/T is intended to mean an oil containing at least one silicon atom.
  • the oils are chosen from non-silicone oils and in particular C 6 -Ci 6 hydrocarbons or hydrocarbons containing more than 16 carbon atoms and in particular alkanes; oils of animal origin; triglyceride oils of plant origin; essential oils; fluoro oils or glycerides of synthetic origin, fatty alcohols; fatty acid and/or fatty alcohol esters other than triglycerides, fatty acid amides and silicone oils.
  • the oils are not oxyalkylenated or glycerolated ethers.
  • the oils do not comprise any C 2 -C 3 oxyalkylene units or any glycerolated units.
  • the oils are not fatty acids which, in salified form, give water-soluble soaps.
  • the oils that can be used in the compositions comprising the pre-hydrolysed henna and the indigo, in particular the compositions A and/or B, as defined previously, or a mixture thereof, may be silicones.
  • the silicones may be volatile or non-volatile, cyclic, linear or branched silicones, which are unmodified or modified with organic groups, having a viscosity from 5x10 "6 to 2.5 m 2 /s at
  • the silicone is chosen from polydialkylsiloxanes, in particular polydimethylsiloxanes (PDMSs), and organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • PDMSs polydimethylsiloxanes
  • organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • Organopolysiloxanes are defined in greater detail in Walter Noll's "Chemistry and
  • the silicones are more particularly chosen from those having a boiling point of between 60°C and 260°C, and even more particularly from:
  • cyclic polydialkylsiloxanes including from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes including from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone ® 7207 by Union Carbide or Silbione ® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone ® 7158 by Union Carbide, and Silbione ® 70045 V5 by Rhodia, and mixtures thereof.
  • linear volatile polydialkylsiloxanes containing 2 to 9 silicon atoms and having a viscosity of less than or equal to 5x10 "6 m 2 /s at 25°C.
  • An example is decamethyltetrasiloxane sold in particular under the name SH 200 by the company Toray Silicone. Silicones belonging to this category are also described in the article published in Cosmetics and Toiletries, Vol. 91 , Jan. 76, P. 27-32 - Todd & Byers "Volatile Silicone fluids for cosmetics”.
  • Use is preferably made of non-volatile polydialkylsiloxanes, polydialkylsiloxane gums and resins, polyorganosiloxanes modified with the organofunctional groups above, and mixtures thereof.
  • silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes bearing trimethylsilyl end groups.
  • the viscosity of the silicones is measured at 25°C according to Standard ASTM 445 Appendix C.
  • oils of the 200 series from the company Dow Corning such as DC200 with a viscosity of 60 000 mm 2 /s;
  • CTFA dimethiconol
  • the fatty alcohols, fatty acid amides and fatty acid esters that can be used as fatty substances a) in the compositions comprising the pre-hydrolysed henna and the indigo, in particular the compositions A and/or B as defined previously, or a mixture thereof, are in the form of oils.
  • fatty alcohols, esters and acids more particularly have at least one linear or branched, saturated or unsaturated hydrocarbon-based group comprising 6 to 30 carbon atoms, which is optionally substituted, in particular with one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • ingredient b) may represent an ester of a C1-C10 alcohol and of a C 6 - C 30 fatty acid such as R-C(0)-0-R' with R representing a linear or branched C 6 -C 30 alkyl or a linear or branched C 6 -C 30 alkenyl group, comprising one or two unsaturations, and R representing a linear or branched C1-C10 alkyl group.
  • R represents a linear C10-C20 alkyl group and R' represents a Ci-C 6 alkyl group that is preferably branched, such as isopropyl myristate.
  • the ingredient ii) represents one or more amides of a C 6 -C 3 o fatty acid and of a primary or secondary, preferably primary, C1-C10 amine, such as those of formula R"-C(0)-N(R a )-R"' with R" representing a linear or branched C 6 -C 3 o alkyl or a linear or branched C 6 -C 30 alkenyl group, comprising one or two unsaturations, which may be substituted with one or more hydroxyl groups, or (di)(Cr C 6 )(alkyl)amino, and R'" representing a linear or branched C1-C10 alkyl group, R a representing a hydrogen atom or an alkyl group as defined for R'".
  • a primary or secondary, preferably primary, C1-C10 amine such as those of formula R"-C(0)-N(R a )-R"' with R" representing a linear or branched C 6 -
  • R" represents a C14-C20 alkenyl group
  • R a represents a hydrogen atom
  • R'" represents a Ci-C 6 alkyl group optionally substituted with (di)(Ci-C 4 )(alkyl)amino such as oleylamidopropyldimethylamine.
  • C 6 -Ci 6 alkanes they are linear or branched, and possibly cyclic. Examples that may be mentioned include hexane, dodecane and isoparaffins such as isohexadecane and isodecane.
  • the linear or branched hydrocarbons containing more than 16 carbon atoms may be chosen from liquid paraffins, petroleum jelly, liquid petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam ® .
  • perhydrosqualene perhydrosqualene.
  • liquid fatty acid triglycerides containing from 6 to 30 carbon atoms for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol ® 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil.
  • liquid fatty acid triglycerides containing from 6 to 30 carbon atoms for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame oil, hazelnut oil,
  • fluoro oils mention may be made of perfluoromethylcyclopentane and perfluoro-1 ,3-dimethylcyclohexane, sold under the names Flutec ® PC1 and Flutec ® PC3 by the company BNFL Fluorochemicals; perfluoro-1 ,2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF 5050 ® and PF 5060 ® by the company 3M, or bromoperfluorooctyl sold under the name Foralkyl ® by the company Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-(trifluoromethyl)perfluoromorpholine sold under the name PF 5052 ® by the company 3M.
  • Flutec ® PC1 and Flutec ® PC3 by
  • the fatty substance(s) a) is (are) different from essential oils.
  • the oil(s) of the invention are non-silicone oils.
  • non-silicone o/V is intended to mean an oil not containing any silicon atoms (Si) and the term “silicone o/V is intended to mean an oil containing at least one silicon atom.
  • the oil(s) are chosen from C 6 -Ci 6 alkanes, polydecenes, liquid esters of a fatty acid and/or of a fatty alcohol, and liquid fatty alcohols, or mixtures thereof.
  • oils are chosen from liquid petroleum jelly, C 6 -Ci 6 alkanes and polydecenes.
  • the oil(s) are chosen from mineral oils such as liquid petroleum jelly.
  • the oils are chosen from oils of natural origin, more particularly oils of plant origin, preferentially chosen from jojoba oil, babassu oil, sunflower oil, olive oil, coconut oil, Brazil nut oil, marula oil, corn oil, argan oil, soybean oil, marrow oil, grapeseed oil, linseed oil, sesame oil, hazelnut oil, apricot oil, macadamia oil, arara oil, coriander oil, almond oil, castor oil, avocado oil, shea butter oil and also rapeseed oil, borage oil, evening primrose oil, pomegranate oil, mango oil, palm oil, cottonseed oil and copra oil.
  • oils of natural origin more particularly oils of plant origin, preferentially chosen from jojoba oil, babassu oil, sunflower oil, olive oil, coconut oil, Brazil nut oil, marula oil, corn oil, argan oil, soybean oil, marrow oil, grapeseed oil, linseed oil, sesame oil, hazelnut oil, a
  • oils of plant origin are chosen from avocado oil, olive oil, coconut oil, copra oil, argan oil and sunflower oil; preferentially, the oil(s), ingredient a) of the invention, is (are) chosen from copra oils.
  • the composition comprising the pre-hydrolysed henna, and in particular the composition A as defined previously comprises one or more oils in an amount inclusively between 1 % and 80% by weight, relative to the total weight of the composition, more particularly between 2% and 50% by weight, preferentially between 3% and 30% by weight and more preferentially between 5% and 15% by weight, relative to the total weight of said composition.
  • Composition B used in the process of the invention preferably comprises one or more oils in an amount particularly inclusively between 1 % and 80% by weight, more particularly between 2% and 50% by weight, preferentially between 3% and 40% by weight and more preferentially between 5% and 25% by weight, relative to the total weight of said composition.
  • compositions comprising the pre-hydrolysed henna and the indigo, in particular the composition A or B, as defined previously, or a mixture thereof, comprise a) one or more butters, which may be identical or different.
  • the term “butter” (also known as a “pasty fatty substance”) is intended to mean a lipophilic fatty compound with a reversible solid/liquid change of state, comprising at a temperature of 25°C and at atmospheric pressure (760 mmHg), a liquid fraction and a solid fraction.
  • the starting melting point of the pasty compound can be less than 25°C.
  • the liquid fraction of the pasty compound measured at 25°C can represent 9% to 97% by weight of the compound. This liquid fraction at 25°C preferably represents between 15% and 85% and more preferably between 40% and 85% by weight.
  • the butter(s) have an end melting point of less than 60°C.
  • the butter(s) have a hardness of less than or equal to 6 MPa.
  • the butters or pasty fatty substances have, in the solid state, an anisotropic crystal organization, which is visible by X-ray observation.
  • the melting point corresponds to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in the standard ISO 1 1357-3; 1999.
  • the melting point of a pasty substance or of a wax may be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name DSC Q2000 by the company TA Instruments.
  • DSC differential scanning calorimeter
  • sample preparation and measurement protocols are as follows:
  • the measurements are performed on the abovementioned calorimeter.
  • the oven is flushed with nitrogen. Cooling is performed by an RCS 90 heat exchanger.
  • the sample is then subjected to the following protocol: it is first placed at a temperature of 20°C, and then subjected to a first temperature rise passing from 20°C to 80°C, at a heating rate of 5°C/minute, then is cooled from 80°C to -80°C at a cooling rate of 5°C/minute and finally subjected to a second temperature rise passing from -80°C to 80°C at a heating rate of 5°C/minute.
  • the variation of the difference in power absorbed by the empty crucible and by the crucible containing the sample of butter is measured as a function of the temperature.
  • the melting point of the compound is the value of the temperature corresponding to the top of the peak of the curve representing the variation in the difference in power absorbed as a function of the temperature.
  • the end melting point corresponds to the temperature at which 95% of the sample has melted.
  • the liquid fraction by weight of the butter at 25°C is equal to the ratio of the heat of fusion consumed at 25°C to the heat of fusion of the butter.
  • the heat of fusion of the pasty compound is the heat consumed by the compound in order to change from the solid state to the liquid state.
  • the butter is said to be in the solid state when all of its mass is in crystalline solid form.
  • the butter is said to be in the liquid state when all of its mass is in liquid form.
  • the heat of fusion of the butter is equal to the integral of the entire melting curve obtained using the abovementioned calorimeter, with a temperature rise of 5 or 10°C/rminute, according to Standard ISO 1 1357-3:1999.
  • the heat of fusion of the butter is the amount of energy required to make the compound change from the solid state to the liquid state. It is expressed in J/g.
  • the heat of fusion consumed at 25°C is the amount of energy absorbed by the sample to change from the solid state to the state that it has at 25°C, composed of a liquid fraction and a solid fraction.
  • the liquid fraction of the butter measured at 32°C preferably represents from 30% to
  • the temperature of the end of the melting range of the pasty compound is less than or equal to 32°C.
  • the liquid fraction of the butter measured at 32°C is equal to the ratio of the heat of fusion consumed at 32°C to the heat of fusion of the pasty compound.
  • the heat of fusion consumed at 32°C is calculated in the same way as the heat of fusion consumed at 23°C.
  • sample preparation and measurement protocols are as follows:
  • the compositions A and B as defined previously, or a mixture thereof according to the invention, or the butter are placed in a mould 75 mm in diameter which is filled to approximately 75% of its height.
  • the mould is placed in a Votsch VC 0018 programmable oven, where it is first placed at a temperature of 80°C for 60 minutes, then cooled from 80°C to 0°C at a cooling rate of 5°C/minute, and then left at the stabilized temperature of 0°C for 60 minutes, and then subjected to a temperature rise ranging from 0°C to 20°C, at a heating rate of 5°C/minute, and then left at the stabilized temperature of 20°C for 180 minutes.
  • the compression force measurement is taken using a TA TX2i texturometer from Swantech.
  • the spindle used is chosen according to the texture:
  • the measurement comprises three steps:
  • the hardness value measured during the first step corresponds to the maximum compression force measured in newtons divided by the area of the texturometer cylinder expressed in mm 2 in contact with the butter or the composition according to the invention.
  • the hardness value obtained is expressed in megapascals or MPa.
  • the particular butter(s) are of plant origin, such as those described in Ullmann's Encyclopedia of Industrial Chemistry ("Fats and Fatty Oils", A. Thomas, published on 15/06/2000, DOI: 10.1002/14356007.a10_173, point 13.2.2.2. Shea Butter, Borneo Tallow, and Related Fats (Vegetable Butters)).
  • ingredient a) is chosen from shea butter
  • Karite Nilotica butter (Butyrospermum parkii), galam butter, (Butyrospermum parkii), Borneo butter or fat or tengkawang tallow (Shorea stenoptera), shorea butter, ill ipe butter, madhuca butter or Bassia madhuca longifolia butter, mowrah butter (Madhuca latifolia), katiau butter (Madhuca mottleyana), phulwara butter (M.
  • the weight content of Ci 6 fatty acid triglycerides is less than 23%.
  • the butter(s) according to the invention are chosen from murumuru butter, ucuuba butter, shorea butter, illipe butter, shea butter and cupuacu butter, and even more preferentially from murumuru butter and ucuuba butter.
  • the weight content of Ci 6 fatty acid triglycerides expressed relative to the total amount of fatty acid triglycerides, ranges from 0 to 22%, better still from 0 to 15% and even better still from 2% to 12%.
  • Composition B used in the process of the invention may comprise one or more butters in an amount particularly inclusively between 1 % and 80% by weight, more particularly between 2% and 50% by weight, preferentially between 3% and 40% by weight and more preferentially between 5% and 25% by weight, relative to the total weight of said composition.
  • Composition A may comprise one or more butters in an amount particularly inclusively between 1 % and 80% by weight, relative to the total weight of the composition, more particularly between 5% and 60% by weight, preferentially between 10% and 40% by weight and more preferentially between 15% and 30% by weight, relative to the total weight of said composition.
  • composition A or B of the invention comprises as ingredient b) a mixture of one or more identical or different oils, as defined previously, and of one or more identical or different butters, as defined previously.
  • composition which comprises the pre-hydrolysed henna in particular the composition A, may comprise one or more oils and one or more butters in which the amount [oil(s) + butter(s)] is particularly inclusively between 0.5% and 80% by weight, relative to the total weight of the composition, more particularly between 1 % and 50% by weight, preferentially between 2% and 30% by weight and more preferentially between 3% and 15% by weight, relative to the total weight of said composition.
  • composition B of the invention comprises one or more oils and one or more butters in which the amount [oil(s) + butter(s)] is inclusively between 0.5% and 80% by weight, more particularly between 1 % and 50% by weight, preferentially between 2% and 40% by weight and more preferentially between 3% and 25% by weight, relative to the total weight of said composition.
  • compositions comprising the pre-hydrolysed henna and the indigo in particular the compositions A and/or B, as defined previously, or a mixture thereof, comprise one or more fatty substances a) different from the oils and from the butters as defined previously.
  • the composition also comprises one or more waxes, preferably of plant origin.
  • the waxes may be fatty alcohols or fatty esters that are solid at ambient temperature and at atmospheric pressure.
  • the composition comprises as third constituent one or more solid fatty alcohols, preferably of plant origin.
  • the fatty alcohols that are suitable for use in the invention are more particularly chosen from linear saturated alcohols comprising from 6 to 30 carbon atoms and preferably from 8 to 30 carbon atoms. Mention may be made, for example, of cetyl alcohol, stearyl alcohol and a mixture thereof (cetearyl alcohol). As regards the solid esters of fatty acids and/or of fatty alcohols, mention may preferably be made of esters of saturated linear fatty acids and of saturated linear fatty alcohols, such as cetyl palmitate, stearyl stearate and cetyl stearate.
  • the composition also comprises one or more waxes, other than the fatty alcohols and fatty esters mentioned above, preferably of plant origin.
  • non-silicone waxes are chosen in particular from carnauba wax, candelilla wax, esparto wax, paraffin wax, ozokerite, plant waxes, such as olive tree wax, rice wax, hydrogenated jojoba wax or absolute flower waxes, such as the blackcurrant blossom essential wax sold by the company Bertin (France), animal waxes, such as beeswaxes or modified beeswaxes (cerabellina); other waxes or waxy raw materials that can be used according to the invention are in particular marine waxes, such as that sold by the company Sophim under the reference M82, polyethylene waxes or polyolefin waxes in general.
  • compositions comprising the decontaminated pre-hydrolysed henna and the indigo in particular the compositions A and/or B, as defined previously, or a mixture thereof, comprise a) one or more silicone waxes, resins or gums.
  • the silicone gums that can be used in accordance with the invention are in particular polydialkylsiloxanes and preferably polydimethylsiloxanes having high number-average molecular weights of between 200 000 and 1 000 000, used alone or as a mixture in a solvent.
  • This solvent can be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane and tridecane, or mixtures thereof.
  • Products that may be used more particularly in accordance with the invention are mixtures such as:
  • CTFA hydroxy-terminated polydimethylsiloxane or dimethiconol
  • CFA cyclic polydimethylsiloxane
  • product Q2 1401 sold by the company Dow Corning
  • the product SF 1236 is a mixture of a gum SE 30 defined above, with a viscosity of 20 m 2 /s and of an oil SF 96 with a viscosity of 5x10 "6 m 2 /s.
  • This product preferably includes 15% of gum SE 30 and 85% of an oil SF 96.
  • organopolysiloxane resins that may be used in accordance with the invention are crosslinked siloxane systems containing the following units:
  • R represents an alkyl containing 1 to 16 carbon atoms.
  • R denotes a C C 4 lower alkyl group, more particularly methyl.
  • the fatty substance(s) do not comprise any C 2 -C 3 oxyalkylene units or any glycerolated units.
  • the fatty substance(s) used in the composition comprising the henna are liquid, such as the oils chosen from non-silicone oils, and in particular C 6 -Ci 6 hydrocarbons or hydrocarbons containing more than 16 carbon atoms and in particular alkanes; oils of animal origin; triglyceride oils of plant origin; essential oils; fluoro oils or glycerides of synthetic origin, fatty alcohols; fatty acid and/or fatty alcohol esters other than triglycerides, and silicone oils.
  • the fatty substance(s) are chosen from oils of plant origin such as jojoba oil, babassu oil, sunflower oil, olive oil, coconut oil, Brazil nut oil, marula oil, corn oil, argan oil, soybean oil, marrow oil, grapeseed oil, linseed oil, sesame oil, hazelnut oil, apricot oil, macadamia oil, arara oil, coriander oil, almond oil, castor oil, avocado oil, shea butter oil and also rapeseed oil, borage oil, evening primrose oil, pomegranate oil, mango oil, palm oil, cottonseed oil and copra oil; preferentially, the fatty substance(s) are chosen from avocado oil, olive oil, coconut oil, copra oil, argan oil and sunflower oil; more preferentially, the fatty substance(s) are chosen from copra oil.
  • oils of plant origin such as jojoba oil, babassu oil, sunflower oil, olive oil, coconut oil, Brazil nut oil, marula oil, corn oil
  • the mixture of the process for preparing the composition according to the invention of step 1 ) also comprises one or more fatty substances as defined previously, in an amount of between 0.05% and 30%, preferably between 1 % and 20%, better still between 5% and 15% by weight relative to the total weight of the mixture of henna and aqueous medium.
  • compositions comprising the pre-hydrolysed henna and the indigo in particular the compositions A and/or B as defined previously, or a mixture thereof, preferably comprise a content of fatty substances different from oil(s) and butter(s) as defined previously ranging from 0.5% to 50% by weight, better still from 1 % to 30% by weight and even better still from 1 % to 20% by weight relative to the total weight of said composition.
  • Basifying agent (s) s
  • the process for dyeing keratin fibres implements a step of post-treatment with one or more basifying agent(s).
  • the alkaline agents are preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates, alkanolamines such as monoethanolamine, diethanolamine and triethanolamine, and also derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds having the following formula:
  • formula W is a linear or branched (CrC 6 )alkylene group such as propylene, optionally substituted with a hydroxyl group or a Ci-C 4 alkyl radical;
  • R a , Rb, R c and R d which may be identical or different, represent a hydrogen atom or a C C 4 alkyl or d-C 4 hydroxyalkyl radical.
  • the alkaline agent(s) is (are) one or more
  • the process for dyeing keratin fibres of the invention uses an aqueous composition comprising one or more carbonates or bicarbonates, which may be identical or different.
  • bicarbonates also known as hydrogencarbonates, with the following formulae:
  • the (bi)carbonate(s) is (are) chosen from alkali metal or alkaline-earth metal bicarbonates, preferentially alkali metal bicarbonates.
  • These hydrogencarbonates can originate from a natural water, for example spring water from the Vichy basin or from La Roche-Posay, or Badoit water (cf. Patent, for example the document FR 2 814 943).
  • Mention may in particular be made of sodium carbonate [497-19-8] Na 2 C0 3
  • sodium hydrogencarbonate or sodium bicarbonate [144-55-8] NaHC0 3
  • sodium dihydrogencarbonate Na(HC0 3 )2-
  • the dyeing process implements, after the rinsing step 2), the application:
  • composition D comprising:
  • the (bi)carbonates are chosen from alkali metal or alkaline-earth metal and ammonium bicarbonates, preferentially alkali metal bicarbonates; and
  • composition D is left on said fibres for a period of between 5 minutes and 1 hour, preferably between 10 minutes and 40 minutes, particularly between 15 minutes and 30 minutes, at a temperature of between 20°C and 30°C, preferably at
  • said wet fibres are then subjected to a heat treatment at a temperature particularly of between 35°C and 80°C, preferably between 40 and 60°C, for a period of between 15 minutes and 3 hours, in particular between 30 minutes and two hours, preferably the heat treatment is carried out at 45°C for 1 hour, preferably the wet fibres are placed under plastic films for the heat treatment;
  • said fibres are then dried in the open air or with a hairdryer.
  • the (bi)carbonate agent(s) used preferably represent(s) from 0.001 % to 20% by weight of the total weight of the composition(s) containing the (bi)carbonate agent(s) and even more preferentially from 0.01 % to 10% by weight, better still from 1 % to 6%.
  • compositions comprising the decontaminated pre-hydrolysed henna and the indigo may be in non-compact clinical forms, such as a lotion, a mousse, a cream or a gel, or in any other form appropriate for dyeing keratin fibres.
  • the composition B is in compact form and in different forms as a function of the desired compacting, in particular in the form of pebbles, in the form of stones, in the form of soaps, in the form of pyramids, in the form of cartons or in the form of plates.
  • compositions comprising the decontaminated pre-hydrolysed henna and the indigo, in particular the compositions A and/or B as defined previously, or a mixture thereof, used in the process of the invention are cosmetic, i.e. they are cosmetically acceptable and therefore suitable for use for application to keratin fibres, in particular human keratin fibres such as the hair.
  • the process for dyeing keratin fibres uses one or more "mordants”, i.e. metal salts conventionally used in “mordanting” (see for example Ullmann's Encyclopedia of Industrial Chemistry ("Textile Dyeing", Herbert Leube et al., DOI: 10.1002/14356007.a26_351 , and in particular point 4.8.2, p. 72 ; ibid, "Metal- complex dyes", Klaus Gryschtol et al., DOI : 10.1002/14356007.a16_299).
  • the process of the invention does not use "mordants", in particular no composition of the invention comprises mordants.
  • compositions comprising the decontaminated pre-hydrolysed henna and the indigo, in particular the compositions A and/or B, as defined previously, or a mixture thereof, comprise water.
  • This water constitutes all or part of an aqueous phase C .
  • aqueous phase is intended to mean a phase which comprises essentially water, and also comprises other ingredients that are water-miscible or water-soluble at ambient temperature and at atmospheric pressure, different from polyols.
  • polar or polar protic organic solvents as defined below, different from polyols, salts of inorganic or organic acids or bases, or water-soluble cosmetic active agents.
  • Compositions A, B and/or C may comprise one or more organic solvents. Mention may be made, as organic solvent, for example, of lower Ci-C 4 alkanols, such as ethanol and isopropanol; and also aromatic alcohols, such as benzyl alcohol or phenoxyethanol.
  • organic solvent for example, of lower Ci-C 4 alkanols, such as ethanol and isopropanol; and also aromatic alcohols, such as benzyl alcohol or phenoxyethanol.
  • the organic solvents are present in proportions preferably of between 0.1 % and 20% by weight approximately and even more preferentially between 0.5% and 10% by weight approximately relative to the total weight of the composition under consideration.
  • the compositions comprising the decontaminated pre-hydrolysed henna and the indigo, in particular the compositions A and/or B as defined previously, or a mixture thereof, contain water, preferably in an amount ranging from 5% to 90%, better still from 20% to 8%, particularly from 40% to 75% by weight relative to the total weight of said composition.
  • the decontaminated composition which comprises the prehydrolysed henna in particular the composition A, as defined previously, comprises only ingredients of natural origin.
  • composition B comprises only ingredients of natural origin.
  • one or more clays which may be identical or different, as defined hereinafter, are, according to one preferred embodiment of the invention, added. Once the clay has been added to the pre-hydrolysed henna composition, it is understood that the composition is decontaminated according to any one of the decontamination methods a) to f) as defined previously.
  • the composition B comprises one or more clays, which may be identical or different, as defined hereinafter.
  • compositions comprising the decontaminated pre-hydrolysed henna, preferably A, the composition B and/or the composition C, as defined previously, of the invention may also contain various adjuvants conventionally used in hair dye compositions, such as anionic, cationic, non-ionic, amphoteric or zwitterionic polymers or mixtures thereof, anionic, cationic, non-ionic or zwitterionic surfactants, inorganic or organic thickeners, and in particular anionic, cationic, non-ionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents other than the butters or oils of the invention, for instance ceramides, film-forming agents, preserving agents, opacifiers and inorganic or organic thickeners such as clays.
  • adjuvants conventionally used in hair dye compositions, such as anionic, cationic, non-ionic, amphoteric or zwitterio
  • composition comprising the decontaminated pre-hydrolysed henna, in particular A, and/or B, as defined previously, is (are) in the form of an emulsion, in which case A, B and/or B contain surfactants.
  • the above adjuvants are generally present in an amount for each of them of between 0.01 % and 40% by weight relative to the weight of the composition, and preferably between 0.1 % and 20% by weight relative to the weight of the composition under consideration.
  • compositions comprising the decontaminated pre-hydrolysed henna, in particular A, B and/or C of the invention as defined previously may also contain one or more additional direct dyes other than the henna powder and/or indigo-producing plant powder.
  • direct dyes are chosen, for example, from those conventionally used in direct dyeing, and among which mention may be made of any commonly used aromatic and/or non-aromatic dyes such as neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, natural direct dyes, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes, azine, triarylmethane, indoamine, methine, styryl, porphyrin, metalloporphyrin, phthalocyanine, methine cyanine direct dyes, and fluorescent dyes.
  • aromatic and/or non-aromatic dyes such as neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, natural direct dyes, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes, azine, triarylmethane, ind
  • compositions comprising the decontaminated pre-hydrolysed henna, in particular A, B and/or C of the invention as defined previously may also contain one or more natural dyes other than henna and indigo-producing plant(s).
  • natural direct dyes mention may be made of juglone, isatin, curcumin, spinulosin, apigenidin and orceins.
  • These natural dyes may be added in the form of defined compounds, extracts or plant parts.
  • Said defined compounds from extracts or from plant parts are preferably in the form of powders, in particular fine powders whose particles have sizes identical to that of the henna and/or indigo-producing plant powder a) as defined previously.
  • the natural or non-natural direct dye(s), other than the henna and/or indigo-producing plant powder a), in the composition according to the invention particularly represents from 0.001 % to 10% by weight relative to the total weight of the composition and even more preferentially from 0.05% to 5% by weight relative to the total weight of the composition under consideration.
  • compositions comprising the decontaminated pre-hydrolysed henna, in particular A, and also B and/or C of the invention as defined previously do not contain any synthetic direct dyes, i. e. dyes which do not occur naturally.
  • compositions comprising the decontaminated pre-hydrolysed henna, in particular A, and also B and/or C of the invention as defined previously may also contain one or more oxidation bases and/or one or more couplers conventionally used for dyeing keratin fibres.
  • oxidation bases mention may be made of para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, bis-para-aminophenols, ortho- aminophenols and heterocyclic bases, and the addition salts thereof.
  • compositions comprising the decontaminated pre-hydrolysed henna, in particular A, B and/or C of the invention do not contain any para-phenylenediamine(s).
  • couplers mention may be made in particular of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and the addition salts thereof.
  • the oxidation base(s) present in the composition(s) are each generally present in an amount of between 0.001 % and 10% by weight, relative to the total weight of the dye composition(s).
  • compositions comprising the decontaminated pre-hydrolysed henna, in particular A, B and/or C do not contain any oxidation dyes. pH of the compositions
  • the pH of the aqueous composition comprising the decontaminated pre-hydrolysed henna, in particular A, and also B, is acid to neutral (3.5-6.5) and more preferentially from 5 to 6.5 and/or C is alkaline, i.e. of pH around 8.5 (preferably ranging from 7.5 to 9, better still from 7.5 to 8.7).
  • the pH of the aqueous composition comprising the decontaminated pre-hydrolysed henna, in particular A, and also B and/or C may be adjusted to the desired value by means of acidifying or alkaline agents normally used in the dyeing of keratin fibres or alternatively using conventional buffer systems.
  • inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid or carboxylic acids.
  • the alkaline agents are as defined previously.
  • Example 1 Henna alone The percentages are indicated on a weight basis relative to 100 g of composition.
  • compositions 1 and 2 are Compositions 1 and 2
  • compositions 1 and 2 were prepared by mixing the ingredients of the table in a mixer, and are left stirring at 100 rpm for a period of between 2 hours and 6 hours at ambient temperature (25°C). The compositions are then deflocculated at a rotational speed of 700 rpm for 4 minutes - 900 rpm for 4 minutes. Compositions 1 and 2 are in the form of pastes. These pastes are then bagged under vacuum at a pressure of between 20 and 200 mb, for 1 minute. The packaging is carried out in sealed multilayer pouches under vacuum; in particular, the pouches are constituted of polyethylene terephthalate (PET), polypropylene terephthalate (PPT) and/or polyamide imide (Al). These pastes can also be packaged under an inert atmosphere (argon or nitrogen).
  • PET polyethylene terephthalate
  • PPT polypropylene terephthalate
  • Al polyamide imide
  • the pouches are stored at 25°C for 2 hours, 6 hours and 24 hours.
  • the pouches are then opened, and an amount of 20 g of composition comprising the henna is placed on locks of 1 g (20/1 bath ratio) of hair containing 90% natural white hairs (90 NW).
  • the applications are carried out with a leave-on time of 1 h.
  • a control lock was prepared, before henna treatment, and two comparative locks were also dyed with extemporaneously prepared henna which had not been either decontaminated or pre-hydrolysed A, or which had been decontaminated but not pre-hydrolysed B, it being understood that the bath ratio is identical, namely 20 g of composition per 1 g of 90 NW hair.
  • the colouring obtained was measured using a Minolta CM-2600D spectrocolorimeter.
  • L * represents the intensity of the colour
  • a * indicates the green/red colour axis
  • b * indicates the blue/yellow colour axis.
  • the lower the value of L the darker or more intense the colour.
  • the higher the value of a * the redder the shade, and the higher the value of b * , the yellower the shade.
  • the variation in colouration of the locks before and after treatment is calculated according to the following equation:
  • L * , a * and b * represent the values measured after dyeing
  • L 0 * , a 0 * and bo * represent the values before dyeing
  • L * represents the intensity of the colour
  • a * indicates the green/red colour axis
  • b * indicates the blue/yellow colour axis.
  • the decontaminated pre-hydrolysed henna makes it possible to obtain colours that are very effective in particular in terms of colour buildup, intensity and chromaticity, compared with the non-pre-hydrolysed and non- decontaminated henna.
  • Composition 3 based on pre-hydrolysed and decontaminated henna
  • Composition 4 based on indigo decontaminated using gamma-radiation at 25 KGy
  • step 3 is not to heat over the plastic film and to allow the hair to dry naturally. Colorimetric results
  • the colouring obtained was measured using a Minolta CM-2600D spectrocolorimeter.
  • L * represents the intensity of the colour
  • a * indicates the green/red colour axis
  • b * indicates the blue/yellow colour axis.
  • the lower the value of L the darker or more intense the colour.
  • the higher the value of a * the redder the shade, and the higher the value of b * , the yellower the shade.
  • L * , a * and b * represent the values measured after dyeing
  • L 0 * , a 0 * and bo * represent the values before dyeing
  • L * represents the intensity of the colour
  • a * indicates the green/red colour axis
  • b * indicates the blue/yellow colour axis.

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Abstract

La présente invention concerne i) un procédé pour préparer une composition aqueuse comprenant du henné pré-hydrolysé et décontaminé, ii) la composition aqueuse préparée selon le procédé, iii) un procédé pour colorer des fibres de kératine, en particulier des fibres de kératine humaines, telles que les cheveux, qui utilise la composition comprenant du henné pré-hydrolysé et décontaminé éventuellement extemporanément avec de l'indigo, et iv) l'utilisation de la composition comprenant le henné pré-hydrolysé et décontaminé pour colorer des fibres de kératine.
PCT/EP2015/080403 2014-12-19 2015-12-18 Procédé de coloration de fibres de kératine à l'aide de henné pré-hydrolysé et décontaminé Ceased WO2016097248A1 (fr)

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FR1462873 2014-12-19
FR1462873A FR3030274B1 (fr) 2014-12-19 2014-12-19 Procede de coloration des fibres keratiniques mettant en œuvre du henne pre-hydrolyse et decontamine

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
WO2019121503A3 (fr) * 2017-12-22 2019-08-01 L'oreal Dispositif à compartiments multiples comprenant au moins un joint cassable interne
WO2019121504A3 (fr) * 2017-12-22 2019-08-01 L'oreal Dispositif à compartiments multiples comprenant au moins un joint cassable interne
KR20210053575A (ko) * 2019-11-04 2021-05-12 동의대학교 산학협력단 며느리배꼽을 포함하는 알레르기성 질환의 예방 및 치료용 조성물
JP2024172720A (ja) * 2023-06-01 2024-12-12 株式会社チームパワーソリューション 染毛剤、染毛剤ペーストおよび染毛方法

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JP2014019656A (ja) * 2012-07-13 2014-02-03 Ray Planing Co Ltd 染毛剤
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019121503A3 (fr) * 2017-12-22 2019-08-01 L'oreal Dispositif à compartiments multiples comprenant au moins un joint cassable interne
WO2019121504A3 (fr) * 2017-12-22 2019-08-01 L'oreal Dispositif à compartiments multiples comprenant au moins un joint cassable interne
KR20210053575A (ko) * 2019-11-04 2021-05-12 동의대학교 산학협력단 며느리배꼽을 포함하는 알레르기성 질환의 예방 및 치료용 조성물
KR102271471B1 (ko) 2019-11-04 2021-06-30 동의대학교 산학협력단 며느리배꼽을 포함하는 알레르기성 질환의 예방 및 치료용 조성물
JP2024172720A (ja) * 2023-06-01 2024-12-12 株式会社チームパワーソリューション 染毛剤、染毛剤ペーストおよび染毛方法
JP7681912B2 (ja) 2023-06-01 2025-05-23 Ｔｅａｍ ｐｏｗｅｒ株式会社 染毛剤、染毛剤ペーストおよび染毛方法

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