WO2024126555A1 - Utilisation d'un ou de plusieurs composés alkylamine particuliers pour le traitement cosmétique de fibres kératiniques - Google Patents

Utilisation d'un ou de plusieurs composés alkylamine particuliers pour le traitement cosmétique de fibres kératiniques Download PDF

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Publication number
WO2024126555A1
WO2024126555A1 PCT/EP2023/085518 EP2023085518W WO2024126555A1 WO 2024126555 A1 WO2024126555 A1 WO 2024126555A1 EP 2023085518 W EP2023085518 W EP 2023085518W WO 2024126555 A1 WO2024126555 A1 WO 2024126555A1
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WO
WIPO (PCT)
Prior art keywords
hydrogen atom
group
keratin fibres
represent
formula
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Application number
PCT/EP2023/085518
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English (en)
Inventor
Andrew Greaves
Bérangère Baril
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by L'oreal filed Critical L'oreal
Publication of WO2024126555A1 publication Critical patent/WO2024126555A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—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
    • 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

Definitions

  • the invention also relates to a composition comprising at least one alkylamine compound as described below.
  • These hair care compositions which are intended to be applied regularly to the hair, can be, for example, conditioners, masks or sera, and can be provided in the form of gels, hair lotions and care creams which are more or less thick.
  • a subject-matter of the present invention is thus in particular the use of one or more alkylamine compounds corresponding to the general formula (I): in which formula (I):
  • Ri, R2, R3 and R4 which are identical or different, represent a hydrogen atom; a linear or branched C1-C4 hydrocarbon group, optionally substituted by one or more identical or different groups chosen from hydroxyl or amino (NH2); a hydroxyl group; a C1-C4 alkoxy group; an amino (NH2) group; preferably a hydrogen atom;
  • R9 represents a hydrogen atom or a linear or branched Ci-Cs hydrocarbon group, optionally substituted by one or more identical or different groups chosen from hydroxyl or amino (NH2) and/or optionally interrupted by one or more heteroatoms chosen from O, S or NR, with R denoting a hydrogen atom or a C1-C4 alkyl group, preferably optionally interrupted by O or S; R9 preferably representing a hydrogen atom; with the proviso that, when R9 represents a hydrogen atom, then Rs or Rio cannot represent a hydroxyl group; with the proviso that, when Ri, R2, R3, R4, Rs, Re, R7, Rs, R9, Rio and R11 represent a hydrogen atom, then the compound of formula (I) is in a nonpolymerized form.
  • ⁇ Rs and Re which are identical or different, represent a hydrogen atom or a linear or branched C1-C4 hydrocarbon group; preferably a hydrogen atom;
  • R3 and R4 represent a hydrogen atom.
  • R7 and Rn which are identical or different, represent a hydrogen atom or a linear or branched C1-C3, preferably C1-C2, in particular Ci, hydrocarbon group.
  • Ri, R2, R3, R4, Rs, Re, R7, Rs, Rio and Rn represent a hydrogen atom.
  • ⁇ Ri, R2, R3, R4, Rs, Re, R7 and Rn represent a hydrogen atom
  • the compound of formula (I) is chosen from the group consisting of 4-(2-aminoethyl)phenol, its optical isomers, its geometrical isomers, its tautomers, its organic or inorganic acid or base salts, and its solvates, such as the hydrates.
  • the use of the compound(s) of formula (I), as defined above takes place in a pH range extending from 3 to 10, preferably at acidic pH, i.e. pH less than 7 (the value 7 being excluded).
  • the use of the compound(s) of formula (I), as defined above, can take place in a medium in which the pH varies from 3 to 10, preferably at acidic pH, i.e. pH less than 7 (the value 7 being excluded).
  • the use of the compound(s) of formula (I), as defined above advantageously takes place in a reaction medium in which the pH varies from 3 to a value strictly of less than 7, more preferentially in a pH range extending from 4 to 5.
  • the present invention relates to the use of one or more compounds of formula (I) as described above for the cosmetic treatment of keratin fibres, without detrimentally affecting their colour.
  • the term "sensitized keratin fibres” is understood to mean keratin fibres which have been sensitized chemically, i.e. by one or more chemical treatments, such as those described above.
  • sensitized keratin fibres are distinctly different from keratin fibres that have been mechanically stressed.
  • the said at least one compound of formula (I), as defined above may be used for the cosmetic treatment of sensitized keratin fibres (in other words, chemically sensitized keratin fibres) that have also been mechanically stressed.
  • the invention relates to the use of one or more compounds of formula (I), as defined above, for reinforcing sensitized keratin fibres, such as permanent-waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres.
  • the present invention advantageously relates to the use of one or more compounds of formula (I) as described above for preventing the breakage of sensitized keratin fibres, such as permanent- waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres.
  • sensitized keratin fibres such as permanent- waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres.
  • the present invention also relates to a composition
  • a composition comprising at least one alkylamine compound of formula (I), as described above, and their optical isomers, their geometrical isomers, their tautomers, their organic or inorganic acid or base salts, and/or their solvates, such as the hydrates.
  • composition according to the invention comprises at least one compound of formula (I), in which Ri, R2, R3, R4, Rs, Re, R7, Rs, R9, Rio and R11 represent a hydrogen atom, then the composition is devoid of polyphenol oxidase.
  • the compound of formula (I) can be present in the composition according to the invention in a content ranging from 0.01% to 25% by weight, preferably in a content ranging from 0.25% to 15% by weight, more preferentially in a content ranging from 0.5% to 10% by weight, more preferentially still in a content ranging from 1% to 5% by weight, with respect to the total weight of the composition.
  • the composition according to the invention also comprises at least one acidifying agent, preferably an organic and/or inorganic acidifying agent, in particular an inorganic acidifying agent.
  • inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, such as acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids, and their mixtures.
  • the acidifying agents are chosen from the group consisting of inorganic acids, more preferentially sulfuric acid, hydrochloric acid and their mixtures, better still hydrochloric acid.
  • the pH of the composition according to the invention can vary from 3 to 10 and is preferably acidic, i.e. less than 7 (the value 7 being excluded).
  • the pH of the composition according to the invention varies from
  • composition according to the invention can additionally comprise one or more organic solvents.
  • the organic solvent(s) can be chosen from the group consisting of linear or branched monoalcohols having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, polyols, polyethylene glycols, aromatic alcohols and their mixtures.
  • polyethylene glycols of propylene glycol, dipropylene glycol, isoprene glycol, butylene glycol and pentylene glycol.
  • the organic solvent(s) is or are chosen from the group consisting of linear or branched monoalcohols having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, and their mixtures.
  • the organic solvent is ethanol.
  • the total content of organic solvents can vary from 1% to 99.9% by weight, preferably from 10% to 90% by weight, more preferentially from 15% to 50% by weight, with respect to the total weight of the composition according to the invention.
  • the composition according to the invention comprises water.
  • the composition comprises water and at least one organic solvent, preferably chosen from the group consisting of linear or branched monoalcohols having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, in particular ethanol.
  • organic solvent preferably chosen from the group consisting of linear or branched monoalcohols having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, in particular ethanol.
  • the ratio by weight of the content of water to the content of organic solvent varies from 90/10 to 50/50, preferably from 80/20 to 60/40, such as 70/30.
  • the composition does not comprise polyphenol oxidase.
  • composition according to the invention can also optionally comprise one or more additional compounds other than the compounds defined above, preferably chosen from the group consisting of anionic surfactants, cationic surfactants, non-ionic surfactants, amphoteric or zwitterionic surfactants, reducing agents, emollients, antifoaming agents, moisturizing agents, UV-screening agents, peptizers, solubilizers, fragrances, anionic, cationic, non-ionic or amphoteric polymers or their mixtures, antidandruff agents, anti-seborrhoeic agents, vitamins and pro-vitamins, including panthenol, plasticizers, solubilizing agents other than the solvents of the invention, inorganic or organic thickening agents, in particular polymeric thickening agents, antioxidants, hydroxy acids, preservatives and their mixtures.
  • additional compounds other than the compounds defined above preferably chosen from the group consisting of anionic surfactants, cationic surfactants, non-
  • the additional compound(s) are generally present in a content of, for each of them, between 0.01% and 20% by weight, with respect to the total weight of the composition which comprises them.
  • the present invention also relates to the use of the composition as described above for the cosmetic treatment of keratin fibres, in particular human keratin fibres, such as the hair.
  • the composition according to the invention is used for the cosmetic treatment of sensitized keratin fibres, such as permanent- waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres.
  • composition according to the invention is used for reinforcing sensitized keratin fibres, such as permanent-waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres.
  • the term "sensitized keratin fibres” is understood to mean keratin fibres which have been sensitized chemically, i.e. by one or more chemical treatments, such as those described above.
  • composition according to the invention is used in particular for reinforcing chemically sensitized keratin fibres.
  • the composition according to the invention is advantageously used for repairing and/or preventing the breakage of sensitized keratin fibres, such as permanent-waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres.
  • sensitized keratin fibres such as permanent-waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres.
  • the composition according to the invention is advantageously used for repairing and/or preventing the breakage of sensitized keratin fibres, such as permanent-waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres, which are optionally mechanically stressed.
  • sensitized keratin fibres such as permanent-waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres, which are optionally mechanically stressed.
  • mechanical stress is understood to mean, within the meaning of the present invention, that the sensitized keratin fibres are subjected to one or more mechanical stresses, for example one or more bending and/or abrading actions, which are liable to take place by brushing and/or combing.
  • composition according to the invention can be included in a shampooing composition, a conditioning composition, a mask, a serum or other conventional formulation forms known to a person skilled in the art.
  • the present invention relates to a method for the cosmetic treatment of keratin fibres, in particular human keratin fibres, such as the hair, comprising at least the application to said fibres of at least one compound of formula (I) or a composition according to the invention as defined above.
  • the method is advantageously implemented for the cosmetic treatment of sensitized keratin fibres as previously defined.
  • the composition according to the invention comprises at least one compound corresponding to the formula (I), in which Ri, R2, R3, R4, Rs, Re, R7, Rs, R9, Rio and R11 represent a hydrogen atom
  • the method does not comprise a stage of application of polyphenol oxidase, before and/or after the application of said composition according to the invention.
  • composition according to the invention can be applied to dry or wet keratin fibres, preferably wet keratin fibres, and also to all types of fibres, light or dark, washed or unwashed, natural or dyed, permanent- waved, bleached or straightened.
  • the composition according to the invention is applied to sensitized keratin fibres, such as permanent-waved, straightened, dyed and bleached keratin fibres, in particular bleached keratin fibres.
  • sensitized keratin fibres such as permanent-waved, straightened, dyed and bleached keratin fibres, in particular bleached keratin fibres.
  • composition according to the invention can be applied before and/or after the implementation of at least one method for the cosmetic treatment of keratin fibres, in particular chosen from the group consisting of a method for permanent reshaping, dyeing and/or bleaching of keratin fibres, in particular after at least one method for bleaching keratin fibres.
  • composition according to the invention can also be applied during the implementation of at least one method for the cosmetic treatment of keratin fibres, in particular chosen from the group consisting of a method for permanent reshaping, dyeing and/or bleaching of keratin fibres, in particular during at least one method for bleaching keratin fibres.
  • composition according to the invention can be applied after the implementation of at least one method for the cosmetic treatment of keratin fibres, in particular chosen from the group consisting of a method for permanent reshaping, dyeing and/or bleaching of keratin fibres, in particular after at least one method for bleaching keratin fibres, optionally followed by one or more operations of washing keratin fibres.
  • composition according to the invention can be applied immediately or several days after at least one method for the cosmetic treatment of keratin fibres, as defined above.
  • the method according to the invention can comprise: one or more cosmetic treatments of keratin fibres chosen from the group consisting of a method for washing, method for permanent reshaping, dyeing and/or bleaching of keratin fibres, at least the application to said fibres of at least one composition according to the invention.
  • the method according to the invention comprises: one or more cosmetic treatments of keratin fibres chosen from the group consisting of a method for washing, method for permanent reshaping, dyeing and/or bleaching of keratin fibres, in particular one or more methods for bleaching, followed by at least the application to said fibres of a composition according to the invention.
  • the bath ratio for application of the composition according to the invention preferably varies from 0.1 to 10 of composition per gram of keratin fibres.
  • bath ratio is understood to mean the ratio of the total weight of the applied composition to the total weight of the keratin fibres to be treated.
  • the method according to the invention can comprise at least one additional successive stage chosen from the following stages ii) to iv): ii) a stage of leaving the composition on the keratin fibres, preferably for a period of time of at least 10 seconds, said leave-on stage optionally being carried out under a hermetic film of foil or plastic film type; iii) a stage of rinsing and/or washing the keratin fibres;
  • the leave-on stage can have a duration ranging from 10 seconds to 60 minutes, preferably from 30 seconds to 30 minutes.
  • the washing stage can, for example, be carried out using a shampoo.
  • the temperature of the heating device can range from 45°C to 230°C, preferably from 45°C to 100°C, more preferentially from 50°C to 80°C. Use may be made, for example, as heating device, of a hair dryer, a heating hood, an iron or a heating brush.
  • the drying stage iv) can also be a combination of drying in air or with a heating device at a temperature ranging from 50°C to 80°C, such as a hair dryer or a heating hood, followed by a stage of treating with an iron.
  • the method according to the invention is a method for reinforcing keratin fibres, in particular human keratin fibres, such as the hair, without detrimentally affecting the colour thereof.
  • the method according to the invention is a method which makes it possible to prevent the breakage of and/or to repair keratin fibres, in particular human keratin fibres, such as the hair, comprising the application of at least one composition according to the invention as defined above, in particular without detrimentally affecting the colour thereof.
  • the method according to the invention is a method which makes it possible to prevent the breakage of and/or to repair sensitized keratin fibres, such as permanent- waved, straightened, dyed and bleached keratin fibres, especially bleached keratin fibres, in particular without detrimentally affecting the colour thereof.
  • sensitized keratin fibres such as permanent- waved, straightened, dyed and bleached keratin fibres, especially bleached keratin fibres, in particular without detrimentally affecting the colour thereof.
  • the method according to the invention is a method which makes it possible to prevent the breakage of keratin fibres, in particular human keratin fibres, such as the hair, comprising the application of at least one composition according to the invention as defined above.
  • the method according to the invention is a method which makes it possible to repair keratin fibres, in particular human keratin fibres, such as the hair, comprising the application of at least one composition according to the invention as defined above.
  • the method according to the invention is a method which makes it possible to repair sensitized keratin fibres, such as permanent-waved, straightened, dyed and bleached keratin fibres, in particular bleached keratin fibres.
  • composition Al (according to the invention) was prepared by mixing 4-(2- aminoethyl)phenol with an acidifying agent and a mixture of water and absolute ethanol (water/ethanol 70/30 w/w%).
  • composition A2 identical to the composition Al but devoid of 4-(2- aminoethyl)phenol, was prepared.
  • the breakdown of the compositions is shown in Table 1 below:
  • Locks of Caucasian hair with a colour depth level of 4 (DL4), of 2.7 grams and of 27 cm in length, are bleached by two successive bleaching operations, then washed with Elseve Color Vive shampoo, then superficially dried between the fingers (two passes between the fingers).
  • compositions Al and A2 are subsequently each applied to the doubly bleached locks with a bath ratio of 0.4 (i.e. 0.4 gram of composition Al or A2 per 1 gram of lock).
  • the locks are subsequently massaged with the fingers, making circular movements along the entire length of the lock (5 times), and then the lock is left for 5 minutes.
  • the locks are rinsed with tap water for 30 seconds, superficially dried, and subsequently dried at a temperature of 60°C (10 min/g of hair). These various stages are repeated to have 5 applications in total.
  • the locks of hair are subjected to a cyclic fatigue test (CFTT) in order to study their breakage.
  • CFTT cyclic fatigue test
  • the cyclic fatigue technique is known to a person skilled in the art for breakage of keratin fibres (reference: https://www.diastron.eom/app/uploads/2017/06/Dia-Stron-CYC801- Brochure.pdf).
  • the principle of the test is to measure the number of cycles of extension of a single fibre before breakage. Fibres with a length of 30 mm are subjected to a constant stress (140 MPa) and to a constant speed (40 mm/s). The studies are carried out at a temperature of 25°C and 45% relative humidity.
  • a Diastron CYC801 device from Diastron is used. A series of measurements comprises 50 individual hairs. Results: [Table 2]
  • Hair breakage is also studied by a flexabrasion technique known to a person skilled in the art.
  • the flexabrasion technique is known to a person skilled in the art for the breakage of keratin fibres (references: Flexabrasion: A Method for Evaluating Hair Strength, Cosmetics & Toiletries Journal, June 26, 2009, and Hair Breakage in Normal and Weathered Hair: Focus on the Black Patient, Journal of Investigative Dermatology Symposium Proceedings, Volume 12, Issue 2, December 2007, pages 6-9).
  • the principle of the test is to measure the time necessary for hair fibres subjected to a mechanical stress (bending and abrasion) to break.
  • a Flexabrasion device (Fibrestress model from Textechno) is used. An individual hair is attached to a 20 g weight at one end and the other end is attached to an immobile bar.
  • the individual hair carries out a to-and-fro movement over a 300 pm stainless steel wire.
  • the movement exhibits an amplitude of 10 mm and a frequency of 0.5 Hz.
  • Breakage is detected by an optical sensor which records the lifetime (drop time before breakage) in seconds, that is to say the time which the individual hair takes before breaking).
  • a series of measurements comprises 75 individual hairs.
  • a difference in drop time of 100 seconds is acknowledged by a person skilled in the art as a significant difference.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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Abstract

La présente invention concerne l'utilisation d'un ou de plusieurs composés alkylamine particuliers pour le traitement cosmétique des fibres kératiniques, en particulier des fibres kératiniques humaines, telles que les cheveux. L'invention concerne également une composition comprenant au moins un composé alkylamine particulier. La présente invention concerne également un procédé de traitement cosmétique des fibres kératiniques, en particulier des fibres kératiniques humaines, telles que les cheveux, comprenant au moins l'application sur lesdites fibres d'au moins une composition comprenant au moins un composé alkylamine particulier.
PCT/EP2023/085518 2022-12-14 2023-12-13 Utilisation d'un ou de plusieurs composés alkylamine particuliers pour le traitement cosmétique de fibres kératiniques WO2024126555A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FRFR2213400 2022-12-14
FR2213400A FR3143341A1 (fr) 2022-12-14 2022-12-14 Utilisation d’un ou plusieurs composés alkylamines particuliers pour le traitement cosmétique des fibres kératiniques

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WO2024126555A1 true WO2024126555A1 (fr) 2024-06-20

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002015871A1 (fr) * 2000-08-25 2002-02-28 Sederma S.A. Utilisation de la tyramine dans des compositions cosmetiques destinees a eclaicir la peau
WO2020023084A1 (fr) * 2018-07-26 2020-01-30 Applied Biology, Inc. Agonistes du récepteur taar pour le traitement de l'alopécie

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002015871A1 (fr) * 2000-08-25 2002-02-28 Sederma S.A. Utilisation de la tyramine dans des compositions cosmetiques destinees a eclaicir la peau
WO2020023084A1 (fr) * 2018-07-26 2020-01-30 Applied Biology, Inc. Agonistes du récepteur taar pour le traitement de l'alopécie

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Flexabrasion: A Method for Evaluating Hair Strength", COSMETICS & TOILETRIES JOURNAL, 26 June 2009 (2009-06-26)
"Hair Breakage in Normal and Weathered Hair: Focus on the Black Patient", JOURNAL OF INVESTIGATIVE DERMATOLOGY SYMPOSIUM PROCEEDINGS, vol. 12, December 2007 (2007-12-01), pages 6 - 9
KOVACEVIC MAJA ET AL: "Novel shampoo reduces hair shedding by contracting the arrector pili muscle via the trace amine-associated receptor", vol. 18, no. 6, 2 July 2019 (2019-07-02), GB, pages 2037 - 2039, XP093057550, ISSN: 1473-2130, Retrieved from the Internet <URL:https://onlinelibrary.wiley.com/doi/full-xml/10.1111/jocd.13054> DOI: 10.1111/jocd.13054 *

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