WO2013125052A1 - Procédé permettant de traiter des fibres kératiniques - Google Patents

Procédé permettant de traiter des fibres kératiniques Download PDF

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Publication number
WO2013125052A1
WO2013125052A1 PCT/JP2012/055310 JP2012055310W WO2013125052A1 WO 2013125052 A1 WO2013125052 A1 WO 2013125052A1 JP 2012055310 W JP2012055310 W JP 2012055310W WO 2013125052 A1 WO2013125052 A1 WO 2013125052A1
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Prior art keywords
keratin fibers
composition
process according
group
synthetic direct
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PCT/JP2012/055310
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English (en)
Inventor
Boris Lalleman
Maxime De Boni
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L'oreal
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Priority to PCT/JP2012/055310 priority Critical patent/WO2013125052A1/fr
Publication of WO2013125052A1 publication Critical patent/WO2013125052A1/fr

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    • 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
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95

Definitions

  • the present invention relates to a process for treating keratin fibers such as hair.
  • oxidative bases such as ortho- or
  • oxidative bases are generally combined with couplers. These bases and these couplers are colorless or weakly colored compounds which, combined with oxidizing products, can give rise to colored compounds through an oxidative condensation process.
  • This type of dyeing by oxidation makes it possible to get colors with very high visibility, coverage of white hair and in a wide variety of shades but it results in damage to the keratin fibers by the use of oxidizing agents (in particular by repeated application or by combination with other hair treatments).
  • direct dyes are in particular the following: benzene nitrates, anthraquinones, nitropyridines, azos, xanthines, acridinies, azinies, and triarylmethane type.
  • These dyes can be non-ionic, anionic, cationic or amphoteric.
  • These direct dyes are colored or coloring molecules with an affinity for keratin fibers. Most of the direct dyes used have sufficient solubility in aqueous medium and there are now many coloring supports or medium suited for receiving the direct dyes.
  • a composition or compositions containing one or more direct dyes can be applied on keratin fibers for a time needed to obtain the desired shade, and then can be rinsed.
  • the resulting colors are particularly chromatic but remain temporary or semipermanent because of the nature of the interactions which bind the direct dyes to the keratin fiber, and their desorption from the surface and/or core of the fiber is responsible for their weak dyeing power and their poor fastness with washings.
  • some direct dyes can cause staining of the skin or scalp.
  • an objective of the present invention is to provide a dyeing process which is based on direct dye(s) having both good level of color coverage of keratin fibers - but also offering intense coloring - and resistance to external factors or agents, and which can give only little damage to the keratin fibers and/or less stains to the skin or scalp.
  • the above objective of the present invention can be achieved by a process for treating keratin fibers, in particular hair, comprising the steps of:
  • composition comprising at least 0.01% by weight relative to the total weight of the composition, of one or more synthetic direct dyes
  • the process may further comprise the step of rinsing the keratin fibers after the step of applying the composition onto the keratin fibers and/or after the step of heating the keratin fibers.
  • the process may further comprise providing the keratin fibers with mechanical tension.
  • the occlusive space may be formed by at least one coating means.
  • the coating means may be rigid or flexible.
  • the coating means may comprise at least one member selected from the group consisting of a film and a sheet.
  • the keratin fibers may be heated at 60 °C to 150 °C during the step of heating the keratin fibers.
  • the keratin fibers may be heated by at least one heater providing at least one selected from the group consisting of hot air, hot steam, high frequency induction heating, microwave heating, infrared ray irradiation, laser, and flash lamp irradiation.
  • the above coating means may comprise the heater.
  • the synthetic direct dye may be selected from the group consisting of hydrophilic synthetic direct dyes selected from the group consisting of cationic synthetic direct dyes, nonionic synthetic direct dyes and anionic synthetic direct dyes; and hydrophobic synthetic direct dyes.
  • the hydrophobic synthetic direct dye may be selected from the group consisting of nonionic synthetic direct dyes with a logP of at least 2.
  • the composition may comprise the synthetic direct dye(s) in an amount of 0.1 to 30% by weight, relative to the total weight of the composition.
  • composition comprise at least one organic compound which is liquid at 25 °C and atmospheric pressure (760 mmHg) with a value of Hansen solubility parameter ( ⁇ ) of
  • This organic compound may be chosen among C 5 -C 30 alkanols; alcohol ethers, particularly CrC 4 ether of C 5 -C 30 alcohols, preferably saturated, optionally interrupted by one or more non vicinal ether groups; aliphatic esters of Q-C 4 carboxylic acids and C 3 -C 10 monoalcohols or C3-Q0 polyols, optionally interrupted by one or more non vicinal ether groups; aromatic ethers, particularly Ce-Cio, of Q-Q alkyl, optionally bearing a hydroxyl group; alkanol with aryl or oxyaryl substituting group, particularly wherein the aryl part is a C6-C 10 aryl, preferably C 6 , and the alkanol is a Ci-C 4 alkyl; lactones particularly of formula (I)
  • R' represents a hydrogen, a (Q-C ) alkyl group, a (Ci-C 4 ) hydroxyalkyl group, n meansl, 2 or 3; alkylene carbonate of formula (II) :
  • R" represents a hydrogen atom, a (Q-Cs) alkyl group, a (Ci-C 4 ) hydroxyalkyl group.
  • compositions for treating keratin fibers at a temperature from 50 to 250 °C in an occlusive space comprising at least one synthetic direct dye as mentioned above, in an amount of 0.01 % by weight or more, relative to the total weight of the composition.
  • the composition may comprise at least one oxidizing agent.
  • the present invention also relates to a kit for treating keratin fibers, comprising:
  • At least one coating means to form an occlusive space
  • At least one heater to heat the keratin fibers to from 50 to 250 °C in the occlusive space
  • composition comprising at least one synthetic direct dye as previously defined, in an amount of 0.01% by weight or more, relative to the total weight of the composition.
  • the above dyeing process involves in heating keratin fibers in a closed or occlusive environment, which limits the evaporation of water or moisture from the keratin fibers and maintains the keratin fibers at a higher temperature in the wet state.
  • the present invention is a process for treating keratin fibers comprising the steps of:
  • composition comprising at least 0.01% by weight relative to the total weight of the composition, of one or more synthetic direct dyes
  • the present invention can provide keratin fibers with intense color, low selectivity (good level of color coverage along with the keratin fibers from root to tip), resistance to external factors or agents such as a shampoo, and only little damage, and can provide the skin or scalp with less stains. (Composition)
  • composition used for the present invention contains at least one synthetic direct dye. Two or more types of the synthetic direct dye may be used in combination.
  • the synthetic direct dye may be hydrophilic or hydrophobic.
  • the hydrophilic direct dye can be selected from the group consisting of cationic synthetic direct dyes, nonionic synthetic direct dyes, and anionic(acidic) synthetic direct dyes. It is preferable that the hydrophilic synthetic direct dyes have a logP value of less than 2.
  • the logP value conventionally represents the partition coefficient of the dye between octanol and water.
  • the logP value may be calculated according to the method described in Meylan & Howard, Atom/Fragment contribution method for estimating octanol- water partition coefficient, J. Pharm. Sci., 84, 83-92 (1995). This value may also be calculated using a range of commercially available software that determines the logP value as a function of the structure of a molecule, for example, Epiwin software from the United States Environmental Protection Agency.
  • hydrophilic dyes include neutral, anionic(acidic), and cationic dyes such as azo, methine, carbonyl, azine, nitro(hetero)aryl types or tri(hetero)arylmethane direct dyes, porphyrins and phthalocyanines, alone or as mixtures.
  • dyes of the family of the carbonyls mention may be made, for example, of synthetic dyes chosen from acridone, benzoquinone, anthraquinone, naphthoquinone,
  • benzanthrone anthranthrone, pyranthrone, pyrazolanthrone, pyrimidinoanthrone, flavanthrone, indanthrone, flavone, (iso)violanthrone, isoindolinone, benzimidazolone, isoquinolinone, anthrapyridone, pyrazoloquinazolone, perinone, quinacridone, quinophthalone, naphthalimide, anthrapyrimidine, diketopyrrolopyrrole or coumarin dyes.
  • dyes of the family of the cyclic azines mention may in particular be made of azine, xanthene, thioxanthene, fluorindine, acridine, (di)oxazine, (di)thiazine or pyronine dyes.
  • nitro(hetero)aromatic dyes are more particularly nitrobenzene or nitropyridine direct dyes.
  • cationic or noncationic compounds optionally comprising one or more metals or metal ions, such as, for example, alkali and alkaline earth metals, zinc and silicon.
  • tetraazacarbocyanines quinone and in particular anthraquinone, naphthoquinone or benzoquinone direct dyes, or azine, xanthene, triarylmethane, mdoamine, phmalocyanine and porphyrin direct dyes, alone or as mixtures.
  • these synthetic direct dyes are chosen from nitrobenzene dyes, azo, azomethine or methine direct dyes and tetraazacarbocyanines (tetraazapentamethines); alone or as mixtures. Mention may be made, among the azo, azomethine, methine or tetraazapentamethine direct dyes which can be used according to the invention, of the cationic dyes described in Patent
  • D represents a nitrogen atom or the -CH group
  • Ri and R 2 which are identical or different, represent a hydrogen atom; a Ci-C 4 alkyl radical which can be substituted by a -CN, -OH or -NH 2 radical or can form, with a carbon atom of the benzene ring, an optionally oxygen-comprising or nitrogen-comprising heterocycle which can be substituted by one or more Q-Q alkyl radicals; or a 4'-arninophenyl radical,
  • R 3 and R' 3 which are identical or different, represent a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a cyano radical, a C 1 -C 4 alkyl radical, a C1-C4 alkoxy radical or an acetyloxy radical,
  • X " represents an anion, preferably chosen from chloride, methyl sulphate and acetate,
  • A represents a group chosen from the following structures:
  • R4 represents a Ci-C 4 alkyl radical which can be substituted by a hydroxyl radical
  • R 5 represents a hydrogen atom, a Q-C 4 alkoxy radical or a halogen atom, such as bromine, chlorine, iodine or fluorine,
  • 3 ⁇ 4 represents a hydrogen atom or a Q-C 4 alkyl radical or forms, with a carbon atom in the benzene ring, a heterocycle which optionally comprises oxygen and/or is optionally substituted by one or more Q-C 4 alkyl groups,
  • X " represents a cosmetically acceptable anion preferably chosen from chloride, methyl sulphate and acetate,
  • E represents a group chosen from the following structures: in which R' represents a C 1 -C 4 alkyl radical;
  • E can also denote a group with the following structure:
  • hydrophilic direct dyes can be chosen for example, from the following direct dyes.
  • X " represents an anion preferably chosen from chloride, iodide, methyl sulphate, ethyl sulphate acetate.
  • hydrophobic synthetic direct dye have a logP value of at least 2.
  • examples of the hydrophobic synthetic direct dye include those listed in the following table.
  • the logP value of the hydrophobic synthetic direct dyes is greater than 4, preferably greater than 6.
  • the synthetic direct dye may be selected from fluorescent dyes. Two or more types of the fluorescent dye may be used in combination.
  • fluorescent dyes may make it possible to obtain, on dark hair, colors which are more visible than with conventional hydrophilic or hydrophobic direct dyes. Furthermore, these fluorescent dyes, when applied to dark hair, may also make it possible to lighten the hair without damaging it.
  • fluorescent dyes is understood to mean fluorescent compounds and optical brighteners.
  • the fluorescent dye is soluble in the medium of the composition.
  • Fluorescent dyes are fluorescent compounds which absorb visible radiation, for example, wavelengths ranging from 400 to 800 nm, and which are capable of re-emitting light in the visible region at a higher wavelength.
  • the fluorescent dyes useful for the present invention re-emit orange-colored fluorescent light. They exhibit, for instance, a maximum re-emission wavelength ranging from 500 to 700 nm.
  • Non-limiting examples of fluorescent dyes include compounds known in the art, for example, those described in Ullmann's Encyclopedia of Industrial Chemistry, Release 2004, 7th edition, “Fluorescent Dyes” chapter.
  • the optical brighteners of the present disclosure also known under the name of "brighteners”, or “fluorescent brighteners”, or “fluorescent brightening agents” or “F WA”, or “fluorescent whitening agents”, or “whiteners”, or “fluorescent whiteners”, are colorless transparent compounds as they do not absorb in visible light but only in ultraviolet light (wavelengths ranging from 200 to 400 nanometers) and convert the energy absorbed into fluorescent light of higher wavelength emitted in the visible part of the spectrum, generally in the blue and/or green, that is to say in wavelengths ranging from 400 to 550 nanometers.
  • Optical brighteners are known in the art, for example, they are described in Ullmann's
  • the fluorescent dyes which can be used in the composition of the present disclosure include compounds known from the art, for example, those described in French Patent No. 2 830 189.
  • Soluble fluorescent compounds that may especially be mentioned include those belonging to the following families: naphthalimides, coumarins, xanthenes and in particular
  • xanthenodiquinolizines and azaxanthenes naphtholactams; azlactones; oxazines; thiazines;
  • the fluorescent dyes are preferred, more particularly, those re-emitting orange-colored fluorescent light.
  • composition used for the present invention contains the synthetic direct dye(s) in an amount of 0.01% by weight or more, and may contain, for example, 0.01 to 30% by weight, preferably 0.1 to 20% by weight, and more preferably 1 to 10% by weight, relative to the total weight of the composition.
  • compositions used for the present invention may also contain at least one additional dye such as at least a natural direct dye.
  • natural dye mention may be made of quinone dyes (such as lawsone and juglone), alizarin, purpurin, laccaic acid, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, sorghum, isatin, betanin, curcuminoids (such as curcumin), spinulosin, various types of chlorophyll and chlorophyllin, hematoxylin, hematein, brazilein, brazilin, safflower dyes (such as carmamin), flavonoids (such as rutin, quercetin, catechin, epicatechin, morin, apigenidin, and sandalwood), anthocyans (such as apigeninidin and apigenidin), carotenoids, orceins, santalins and cochineal carmine.
  • composition used for the present invention may contain the natural dye(s) in an amount of 0.1 to 30% by weight, preferably 1 to 20% by weight, and more preferably 2 to 10% by weight, relative to the total weight of the composition.
  • the composition used for the present invention may also contain at least one additional dye ⁇ chosen among the oxidative dyes.
  • the oxidation dye comprises one or more oxidation bases and/or one or more couplers.
  • the oxidation bases are chosen from para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases and addition salts thereof.
  • the oxidation base(s) may be present in an amount ranging from around 0.001 to 30% by weight, preferably ranging from 0.001 to 20% by weight, and more preferably 0.1 to 10% by weight, relative to the total weight of the composition.
  • the composition used for the present invention may contain at least one coupler conventionally used for dyeing keratin fibers.
  • couplers conventionally used for dyeing keratin fibers.
  • the coupler(s) may be present in an amount ranging from around 0.001 to 30% by weight, preferably ranging from 0.001 to 20% by weight, and more preferably 0.1 to 10% by weight, relative to the total weight of the composition.
  • the composition used for the present invention contain at least one organic compound which is liquid at 25 °C and atmospheric pressure (760 mmHg) with a value of Hansen solubility parameter ( ⁇ ) of less than 16 MPa 1 2 at 25 °C.
  • the organic compound is preferably capable of functioning as an organic solvent.
  • the ⁇ value is preferably less than 15 MPa at 25 °C, more preferably less than 14.5 MPa 1/2 at 25 °C, and further more preferably less than 14 MPa 1/2 at 25 °C. According to one particularly preferred embodiment, the ⁇ value is greater than 0.
  • the ⁇ value may be greater than 3 MPa 1/2 at 25 °C, preferably greater than 4 MPa 1/2 at 25 °C, and more preferably greater than 5 MPa 1/2 at 25 °C.
  • the organic compounds such as organic solvents, having a value of the Hansen solubility parameter ⁇ as defined previously are, for example, described in the reference work "Hansen solubility parameters- A user's handbook", Charles M. Hansen, CRC Press, 2000, pages 167 to 185.
  • This value takes into account the solubility parameter ⁇ linked to the formation of hydrogen bonds. It is recalled that there are three main types of interactions in organic compounds, non-polar interactions, permanent dipole-dipole interactions and hydrogen bonding type interactions, the latter being the subject of the parameter that defines the organic compound preferably used in the present invention.
  • the organic compound be selected from the group consisting of C 5 -C 30 alkanols; alcohol ethers, particularly CrC 4 ether of C 5 -C 30 alcohols, preferably saturated, optionally interrupted by one or more non vicinal ether groups; aliphatic esters of C 1 -C 4 carboxylic acids and C 3 -C 10 monoalcohols or C 3 -C 10 polyols, optionally interrupted by one or more non vicinal ether groups; aromatic ethers, particularly C 6 -C 10 , of C]-C 6 alkyl, optionally bearing a hydroxyl group; alkanol with aryl or oxyaryl substituting group, particularly wherein the aryl part is a C 6 -C 10 aryl, preferably C 6 , and the alkanol is a C 1 -C 4 alkyl; lactones particularly of formula (I): wherein R' represents a hydrogen, a (Q-Cs) alkyl group, a
  • R" represents a hydrogen atom, a (CrC 8 ) alkyl group, a hydroxyalkyl group.
  • propylene carbonate is preferred.
  • the organic compound be selected from propyleneglycol derivatives, aromatic alcohols and alkylene carbonates.
  • propyleneglycol derivatives mention may be made of propyleneglycol ethers having at least one free alcohol functional moiety, or propyleneglycol esters having at least one ether moiety.
  • aromatic alcohol means an alcohol having at least one hydroxyl group which does not directly bond to an aromatic moiety such as a benzene ring.
  • aromatic alcohols mention may be made of benzyl alcohol, phenyl ethanol, and phenyl propanol.
  • organic compound mention may be made of the compounds in the following table.
  • the composition used for the present invention may contain the organic compound(s) which is/are liquid at 25 °C and atmospheric pressure (760 mmHg) with a value of Hansen solubility parameter ( ⁇ ) of less than 16 MPa 1 2 at 25 °C in an amount of 0.1 to 80% by weight, preferably 1 to 50% by weight, and more preferably 2 to 30% by weight, relative to the total weight of the composition.
  • the composition used for the present invention may contain water.
  • the amount of water in the composition used for the present invention may be at least equal to 40% by weight relative to the total weight of the composition. More preferably, the amount of water may be at least equal to 70% relative to the total weight of the composition.
  • the composition used for the present invention may contain at least one additional organic solvent different from the compound with the value of the component ⁇ of the Hansen solubility parameter as previously defined.
  • additional organic solvent such as ethanol and isopropanol
  • the amount of the above additional organic solvent(s) in the composition used for the present invention may vary between around 0.1 and 80% by weight, preferably between around 0.5 and 50%) by weight, and more preferably between 1 and 30% by weight, relative to the total weight of the composition.
  • addition salt(s) of the oxidation base(s) and/or of the coupler(s) may be in particular chosen from addition salts with acid such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates, and addition salts with base such as sodium hydroxide, potassium hydroxide, ammonium hydroxide, amines and alkanolamines.
  • an oxidizing agent may be used.
  • the oxidizing agents conventionally used for oxidation dyeing of keratinous fibers are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and oxidase enzymes, among which mention may be made of peroxidases, 2-electron oxidoreductases such as uncases and 4-electron oxygenases such as laccases.
  • Hydrogen peroxide is particularly preferred.
  • This oxidizing agent may also be present in the composition used for the present invention or may be applied to keratin fibers independently as the form of an oxidizing composition.
  • compositions used for the present invention may also contain various adjuvants
  • compositions for dyeing hair such as anionic, non-ionic, cationic, amphoteric or zwitterionic polymers, or mixtures thereof, antioxidants, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, conditioning agents, film-forming agents, ceramides, preservatives and opacifying agents.
  • conditioning agent By way of conditioning agent, mention may be made of branched or unbranched, volatile or non- volatile linear or cyclic silicones. These silicones may be in the form of oils, resins or gums, they may in particular be polyorganosiloxanes that are insoluble in the cosmetically acceptable medium.
  • Organopolysiloxanes are defined in greater detail in the work by Walter Noll, "Chemistry and Technology of Silicones” ( 1968) Academic Press. They may be volatile or non- volatile.
  • the silicones are more particularly chosen from those having a boiling point between 60 °C and 260 °C.
  • conditioning agent use can also be made of polymers such as the polyquaterniums 22, 6, 10, 11, 35 and 37 and hexadimethrine chloride.
  • the concentration of conditioning agent(s) in the composition used for the present invention may vary from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight, and more preferably from 0.1 to 3% by weight, relative to the total weight of the composition.
  • compositions used for the present invention may contain, in addition, at least one tMckening agent also known as "rheology modifiers".
  • This agent may be mineral or organic.
  • the organic thickening agents may be chosen from fatty acid amides (coconut diethanolamide or monoethanol-amide, oxyethylenated alkyl ether carboxylic acid monoethanolamide), polymeric thickeners such as cellulose thickeners (hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose), guar gum and its derivatives (hydroxypropyl guar), gums of microbial origin (xanthan gum, scleroglucan gum), homopolymers crosslinked with acrylic acid or acrylamidopropanesulfomc acid and neutral, anionic, amphoteric or cationic associative polymers (polymers comprising hydrophilic zones, and hydrophobic zones having a fatty chain, that are capable, in an aqueous medium, of reversibly associating with
  • the thickener is polymeric and is chosen from cellulose thickeners (hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose), guar gum and its derivatives (hydroxypropyl guar), gums of microbial origin (xanthan gum, scleroglucan gum), homopolymers crosslinked with acrylic acid or acrylamidopropanesulfonic acid.
  • the composition used for the present invention may furthermore contain at least one surfactant.
  • the surfactant(s) may be selected from the following (i) to (iv).
  • anionic surfactants which can be used in the composition according to the invention: alkyl sulfates, alkyl ether sulfates, alkylamidoether sulfates, alkylarylpolyether sulfates, monoglyceride sulfates, alkyl sulfonates, alkyl amide sulfonates, alkyl aryl sulfonates, alpha-olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkyl amide sulfosuccinates, alkyl sulfoacetates, acylsarcosinate, acylglutamates, alkyl sulfosuccinamates, acylisethionates, N-acyltaurates, alkyl and polyglycoside polycarboxylic
  • These compounds can be oxyethylenated and then comprise preferably from 1 to 50 ethylene oxide units.
  • the salts of C 6 -C 24 alkyl and polyglycoside-polycarboxylic acid monoesters can be chosen among the C 6 -C 24 alkyl polyglycoside citrates, C 6 -C 24 alkyl polyglycoside tartrates and the C 6 -C 24 alkyl polyglycoside sulfosuccinates.
  • the anionic surfactant(s) can be chosen from allcaline metal salts such as sodium or potassium salts and preferably sodium, ammonium salts, amine salts and in particular amino alcohols, or alkaline-earth metal salts such as magnesium salts.
  • amino alcohol salts mono-, di- and tri-emanolarnine salts, mono-, di- or tri-isopropanolamine salts, and the salts of 2-amino-2-methyl- 1 -propanol, 2-amino-2-methyl- 1 ,3 -propanediol and tris(hydroxy-methyl)amino methane.
  • alkaline or alkaline earth metal salts and in particular the sodium or magnesium salts are used.
  • (C 12 -C 2 o)alkyl sulfates (C 12 -C 20 )alkylether sulfates comprising from 2 to 20 ethylene oxide units, especially in the form of alkaline metal, ammonium, amino alcohol and alkaline-earth metal salts, or a mixture of these compounds, is preferred.
  • the use of sodium lauryl ether sulfate with 2.2 mol of ethylene oxide is preferred.
  • non-ionic surfactants are themselves also compounds which are well known per se (in this respect see, in particular, "Handbook of Surfactants” by M. R. Porter, published by Blackie & Son (Glasgow and London), 1991 , pp. 116-178). Thus, they may especially be chosen from
  • alcohols non-limiting list
  • a-diols or alkylphenols that are polyethoxylated or polypropoxylated, having a fatty chain comprising, for example 8 to 18 carbon atoms, the number of ethylene oxide or propylene oxide groups possibly ranging, in particular, from 2 to 50.
  • glycerol groups oxyethylenated esters of sorbitan fatty acids having from 2 to 30 mol of ethylene oxide; sucrose fatty acid esters, polyethylene glycol fatty acid esters, alkyl polyglycosides, N-alkylglucamine derivatives, amine oxides such as oxides of (C 10 -C 14 ) alkylamines or oxides of N-acylamino-propylmo holine.
  • amphoteric or zwitterionic surfactants may especially be (non-limiting list) derivatives of aliphatic secondary or tertiary amines in which the aliphatic radical is a linear or branched chain comprising 8 to 18 carbon atoms and containing at least one water-solubilizing anionic group (for example carboxylate, sulfonate, sulfate, phosphate or phosphonate); mention may also be made of (C 8 -C 20 )alkyl betaines, sulfobetaines, (C 8 -C 2 o)alkylamido-(C 1 -C 6 ) alkyl betaines or
  • Caprylamphodiacetate Disodium Capryloamphodiacetate, Disodium Cocoamphodipropionate, Disodium Lauroamphodipropionate, Disodium Capryl-amphodipropionate, Disodium
  • cationic surfactants mention may, in particular, be made (non-limiting list) of: salts of primary, secondary or tertiary fatty amines, optionally polyoxyalkylenated; quaternary ammonium salts such as tetraalkylarnmonium, alkylamidoalkyltrialkylammonium, trialkylbenzylarnmonium, Irialkymyckoxyalkylammonium or alkylpyridinium chlorides or bromides; imidazoline
  • the amount of surfactant(s) present in the composition used for the process of the present invention may vary from 0.01 to 40% by weight, preferably from 0.5 to 30% by weight, relative to the total weight of the composition.
  • the pH of the composition applied to the keratin fibers is generally between 2 and 13, preferably between 3 and 10, and more preferably from 7 to 10. It may be adjusted to the desired value using acidifying or basifying agents commonly used in dyeing keratinous fibers or else using conventional buffer systems.
  • acidifying agents mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid and sulfonic acids.
  • mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid and sulfonic acids.
  • basifying agents mention may be made, by way of example, of ammonium hydroxide, . alkali metal carbonates, alkanolamines such as mono-, di- and triemanolamines and also their derivatives, sodium or potassium hydroxide and compounds of formula below:
  • RZ R4 wherein R denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C ⁇ Q alkyl radical, and R ls R 2 , R 3 and R ⁇ independently denote a hydrogen atom, an alkyl radical or a -C 4 hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine and derivatives thereof. Arginine, urea and monoethanolamine are preferable.
  • the process for treating keratin fibers according to the present invention can be performed by: applying onto the keratin fibers the composition as described above;
  • keratin fibers such as hair are subjected to a specific heating process which is performed in an occlusive space.
  • the heating process can be performed by any heating means which can be freely controlled to realize the temperature desired for the process.
  • the heating process may preferably be performed by using a special heating device or devices that can form an occlusive space to restrict the evaporation of evaporable components such as water in the above-described composition from keratin fibers and keep a predetermined temperature in the heating device throughout the process.
  • a special heating device or devices that can form an occlusive space to restrict the evaporation of evaporable components such as water in the above-described composition from keratin fibers and keep a predetermined temperature in the heating device throughout the process.
  • the evaporable components such as water in the above-described composition evaporate from the keratin fibers, most of the heat energy applied to the keratin fibers will be consumed by the evaporation, and therefore the temperature of the keratin fibers cannot increase up to the predetermined temperature until all evaporable components in the composition evaporate.
  • the above heating device may comprise a heat energy source being either in contact with keratin fibers or apart from keratin fibers, and at least one means to form an occlusive space surrounding the keratin fibers.
  • the heat energy source is used to heat keratin fibers.
  • the heat energy source may be at least one heater providing at least one selected from the group consisting of hot air, hot steam, high frequency induction heating, microwave heating, infrared ray irradiation, laser, and flash lamp irradiation.
  • the occlusive space may be formed by at least one coating means.
  • a plurality of coating means may be used.
  • the coating means may be rigid or flexible.
  • the coating means may comprise at least one member selected from the group consisting of a film and a sheet.
  • the material of the film or the sheet is not limited.
  • the film or the sheet may comprise a thermoplastic or thermosetting resin, a paper, a textile, a bonnet, a metal foil such as aluminum foil, and the like.
  • the film or sheet may be set on a heating rod, a heating bar or a heating plate which is covered by keratin fibers.
  • the coating means may comprise the heat energy source. Therefore, for example, the film or sheet which includes a heater may be set on a rod, a bar, or a plate which is covered by keratin fibers.
  • the occlusive conditions can restrict the evaporation of evaporable components such as water in the above-described composition applied to keratin fibers, and therefore the temperature of the keratin fibers can be increased higher than that obtainable by a conventional heating process or device for the keratin fibers in open conditions. Furthermore, the keratin fibers can be heated effectively, and the keratin fibers can be heated evenly.
  • the occlusive space may comprise apertures, the surface area of which is less than 5 %, preferably less than 3 % and more particularly less than 0.5 % of the total surface area of the coating means.
  • the total surface area of the coating means comprises the surface area of, when it is present, an opening means for the coating means.
  • the apertures may be passages, holes or orifices, which may allow an exchange of air between the occlusive space and the exterior thereof, especially when the reaction such as forming vapor inside the occlusive space is too great.
  • a person skilled in the art could form the apertures such that the diffusion of heat in the occlusive space is not impaired.
  • the keratin fibers can be heated at 50°C to 230 °C, preferably 60 °C to 200 °C, more
  • the heating process may be performed for an appropriate time which is required to treat the keratin fibers.
  • the time length for the heating process is not limited, but it may be from 1 minute to 2 hours, preferably 1 minute to 1 hour, and more preferably 1 minute to 30 minutes.
  • the time for heating may be from 5 to 20 minutes, preferably 10 to 15 minutes.
  • the keratin fibers may be rinsed after the step of applying the composition onto the keratin fibers and/or after the step of heating the keratin fibers.
  • mechanical tension may be applied to the keratin fibers. If mechanical tension is provided to keratin fibers, the treatment process according to the present invention may be performed as follows.
  • keratin fibers are subjected to mechanical tension.
  • the mechanical tension can be applied to the keratin fibers by any means to deform the keratin fibers to an intended shape.
  • the mechanical tension may be provided by at least one reshaping or mechanically tensioning means selected f om the group consisting of a curler, a roller, a clip, a plate and an iron.
  • the reshaping or mechanically tensioning means may comprise at least one heater as described above. If the keratin fibers are rolled around a curler, this rolling-up may be performed on the entire length of the keratin fibers or, for example, on half the length of the keratin fibers. Depending on, for example, the desired hairstyle shape and amount of curls, the rolling-up may be performed with more or less thick locks.
  • the above-described composition is applied to the keratin fibers.
  • the application of the composition may be performed by any means, such as a brush and a comb.
  • the keratin fibers to which the mechanical tension has been applied should be treated with the composition. It may be possible that the keratin fibers are left as they are for a certain amount of time, if necessary.
  • the heat energy is applied to the keratin fibers under occlusive conditions as described above.
  • This process for permanent deformation of keratin fibers may be performed without any step of oxidizing the keratin fibers. Therefore, the time required for the process according to the present invention can be shorter than that for a conventional process which needs an oxidizing step. Furthermore, damage to the keratin fibers by the oxidizing step can be avoided.
  • the keratin fibers may be rinsed after the step of applying the composition onto the keratin fibers and/or after the step of heating the keratin fibers.
  • One embodiment of the treatment process according to the present invention may comprise: a) a step of placing keratin fibers under mechanical tension by rolling them up on at least one reshaping or mechanically tensioning means so as to form curls;
  • the time for the heating should not be limited.
  • the temperature can be set, adjusted and regulated by using one or more heating means, and may be measured with a thermo-measurement probe such as Digital Surface Sensor Module, reference MT-144, sold by Sakaguchi E.H VOC Corp (Japan), set on the keratin fibers.
  • a thermo-measurement probe such as Digital Surface Sensor Module, reference MT-144, sold by Sakaguchi E.H VOC Corp (Japan) set on the keratin fibers.
  • the probe is set on a single keratin fiber.
  • the probe be set on the part of the keratin fibers which directly contacts with the occlusive space, and more preferably, the probe be set on the part of the keratin fibers which directly contacts with the occlusive space and forms the curl end of the keratin fibers, if a curler is used.
  • the temperature is measured at atmospheric pressure of 101,325 Pa.
  • the temperature of the keratin fibers may be constant with a fluctuation of ⁇ 2 or 3 °C over the head, if the keratin fibers are hair, of an individual, and the probe may be set on any type of keratin fibers.
  • the constant temperature with a fluctuation of ⁇ 2 or 3 °C can be obtained for any type of hair, and the temperature of the hair can be controlled to be constant ⁇ 2 or 3 °C during the heating of the hair at a certain temperature.
  • the hair style becomes uniform and homogeneous for the entirety of the hair, and a further excellent hair style can be finally obtained.
  • the coating means may comprise one or more thermal insulating materials, and more advantageously, the coating means may consist of the material(s).
  • thermal insulating material means any material which has an electric conductivity of 0 to 1 W/m°C (PVC: 0.17 W/m°C).
  • the heating means may be adjusted such that the temperature measured on the keratin fibers is 50°C or more, more preferably 55°C to less than 150°C, and further more preferably less than 100°C. It is preferable that the heating be performed by heating via electrical resistance.
  • the coating means is impermeable with regard to the composition used in the step b).
  • At least one of the reshaping or mechanical tensioning means and at least one of the covering means may include a heater.
  • occlusive space means that when the coating means is placed on the reshaping or mechanical tensioning means, or vice versa, they together form a closed structure in which heat can diffuse, but heat cannot diffuse out of or is difficult to diffuse out of the closed structure. It is preferable that the coating means and the reshaping or mechanical tensioning means can form the occlusive space when they are set on the head, if the keratin fibers are hair.
  • the occlusive space may form a condensation cage in which water and a component or components in the composition used in the step b) may evaporate from the keratin fibers, adhere to the wall of the coating means, and drop onto the keratin fibers .
  • This cycle may be repeated during the heating of the keratin fibers.
  • the keratin fibers can be always kept wet, and drying and deterioration of the keratin fibers will be prevented.
  • the formation of the occlusive space is an important characteristic of the present invention, because the keratin fibers in the occlusive space can be kept wet and the temperature of the keratin fibers can be kept constant.
  • the process of the present invention may comprise an additional step of tightening the coating means on the head of an individual, if the keratin fibers are hair, by an elastic cord, an extensible band, or a stretch.
  • the amount of a cosmetic component or components in the composition is advantageously reduced as compared to the processes in the prior art.
  • the amount of the cosmetic component(s) may be 0.3 to 3% by weight of the composition.
  • a coating means may be placed on each hair curler as the reshaping or mechanically tensioning means, if the keratin fibers are hair.
  • each of the hair curlers may be covered individually by a coating means. It is advantageous to cover each hair curler because leaking to the scalp of the composition which has been applied onto keratin fibers in the. step b) can be prevented.
  • a coating means may cover all hair curlers, if two or more hair curlers are used.
  • the coating means may cover the entirety of the head if the keratin fibers are hair.
  • the occlusive space formed in the step d) may be maintained during the step e).
  • the coating means may be removed only after the step e) or after the stopping of the heating in the step e).
  • the composition may be applied to keratin fibers before applying mechanical tension to the keratin fibers. It may be possible that the keratin fibers are left as they are for a certain amount of time, if necessary, before and/or after applying mechanical tension to the keratin fibers, before and/or after applying the above-described composition to the keratin fibers, and before and/or after heating the keratin fibers.
  • the keratin fibers may be fixed by oxidation after being taken out from the coating means.
  • the present invention also relates to use of a composition for treating keratin fibers at a temperature from 50 to 250 °C in an occlusive space, comprising at least one synthetic direct dye as mentioned above in an amount of 0.01% by weight relative to the total weight of the composition.
  • This composition may have the same technical features as those of the
  • composition described above may comprise at least one oxidizing agent.
  • the present invention also relates to a kit for treating keratin fibers, comprising:
  • At least one coating means to form an occlusive space
  • At least one heater to heat the keratin fibers to from 50 to 250 °C in the occlusive space
  • composition comprising at least 0.01% by weight relative to the total weight of the composition, of one or more synthetic direct dyes.
  • the composition may optionally comprise an oxidizing agent.
  • the coating means and the heater, as well as the composition in the kit, may be the same as those described above.
  • each of the other natural hair swatch and the other permed hair swatch was rolled on a curler composed of a 1.7 cm diameter polyethylene cylinder covering an electric resistance. Then, the hair swatch on the curler was further covered with a polyvinylchloride plastic film, and the curler was plugged with electrical connection into a Digital Perm device (Oohiro, model ODIS-2) delivering 10 W of power per curler. Then, the hair swatch was heated for 15 minutes at 90 °C.
  • a dyeing composition A with the following formulation shown in Table 1 was prepared (the unit of the content in Table 1 is grams based on material as provided).
  • a couple of hair swatches of natural or permed Caucasian hair with 90% white hair were treated with the dyeing composition A.
  • each of the natural hair swatch and the other permanent waving treated hair swatch was rolled on a curler composed of a 1.7 cm diameter polyethylene cylinder covering an electric resistance. Then, the hair swatch on the curler was further covered with a polyvinylchloride plastic film, and the curler was plugged with electrical connection into a Digital Perm device (Oohiro, model ODIS-2) delivering 10 W of power per curler. Then, the hair swatch was heated for 15 minutes at 90 °C.
  • Dyeing compositions B to D with the following formulations shown in Table 2 were prepared (the unit of the content in Table 2 is grams based on material as provided).
  • each of the natural and permed hair swatches was rolled on a curler composed of a 1.7 cm diameter polyethylene cylinder covering an electric resistance. Then, the hair swatch on the curler was further covered with a
  • a dyeing composition E with the following formulation shown in Table 3 was prepared (the unit of the content in Table 3 is grams based on material as provided).
  • a couple of hair swatches of natural or permed Caucasian hair with 90% white hair was treated with the dyeing composition E.
  • each of the natural hair swatch and the permed hair swatch was rolled on a curler composed of a 1.7 cm diameter polyethylene cylinder covering an electric resistance. Then, the hair swatch on the curler was further covered with a polyvinylchloride plastic film, and the curler was plugged with electrical connection into a Digital Perm device (Oohiro, model ODIS-2) delivering 10 W of power per curler. Then, the hair swatch was heated for 30 minutes at 90 °C.
  • the colors of the hair swatches according to Example 6 were intense red with a good fastness, and the colored hair swatches had a very soft feel.

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Abstract

La présente invention concerne un procédé permettant de traiter des fibres kératiniques, en particulier des cheveux, comprenant les étapes consistant à : appliquer sur les fibres kératiniques une composition comprenant au moins 0,01 % en poids, par rapport au poids total de la composition, d'un ou de plusieurs colorants directs synthétiques ; placer les fibres kératiniques dans un espace occlusif ; et chauffer les fibres kératiniques à une température comprise entre 50 et 250 °C. La présente invention concerne un nouveau procédé de coloration pour fibres kératiniques, telles que les cheveux, basé sur une ou plusieurs colorations directes pouvant donner une couleur intense aux fibres kératiniques avec un bon niveau de couverture de la couleur, une bonne résistance aux facteurs ou agents externes tels qu'un shampooing, et peu de dommages, et qui provoque moins de taches sur la peau ou le cuir chevelu.
PCT/JP2012/055310 2012-02-24 2012-02-24 Procédé permettant de traiter des fibres kératiniques WO2013125052A1 (fr)

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