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WO1994002114A1 - Procede de prevention de formation de mauvaises odeurs dans une operation de deformation permanente des cheveux et composition pour sa mise en ×uvre - Google Patents

Procede de prevention de formation de mauvaises odeurs dans une operation de deformation permanente des cheveux et composition pour sa mise en ×uvre Download PDF

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Publication number
WO1994002114A1
WO1994002114A1 PCT/FR1993/000756 FR9300756W WO9402114A1 WO 1994002114 A1 WO1994002114 A1 WO 1994002114A1 FR 9300756 W FR9300756 W FR 9300756W WO 9402114 A1 WO9402114 A1 WO 9402114A1
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Prior art keywords
liquid
foam
preferabiy
agents
air
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Ceased
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PCT/FR1993/000756
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English (en)
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WO1994002114A9 (fr
Inventor
Nikoletta Giannovits-Argyriadis
Sophia Mamalakis-Karvounis
Alexandros Stavropoulos
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LOreal SA
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LOreal SA
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants

Definitions

  • the present invention reiates to hair styling mousse products.
  • it relates to non-aerosol hair styling mousse products which provide optimum foaming, hair setting, hair feel and hair conditioning characteristics while reducing stickiness and being easily spreadable on the hair.
  • the desire to have hair retain a particular shape or configuration is one that is widely held. It is possible to alter the shape of the hair either permanently or temporarily. Permanent alteration invoives the use of chemical agents to react with the hair in order to achieve the desired effect. This process can be carried out at either room or elevated temperature.
  • the temporary set given to hair is, as the term indicates, a temporary arrangement which can be removed by water or by shampooing.
  • the materials used to provide the set hâve generally been resins or gums.
  • the temporary set compositions hâve taken the form of gels, lotions and sprays as well as others. The compositions are applied most often to hair dampened with water, combed or by other means spread through the hair and let dry.
  • the set given will vary depending on the materials used.
  • the conventional hair styling mousse generally utilizes a water soluble polymer, water, possibly a conditioning agent, an emulsifier, aesthetic agents and the propellant. More recently, however, due to an increasing public awareness of the effects of volatile orga ⁇ ic compounds, such as aerosol propellants, on the enviro ⁇ ment, hair styling mousse products hâve been formulated without a propellant and dispensed from a manually-actuable container so as to be of the non-aerosol type. Unfortunately, however, there are a number of problems associated with non-aerosol products. In particular they provide mousses which are of poor foam quality and stability and which are undesirably sticky. Moreover, many of thesis formulations are lacking in hair holding, hair feel or hair conditioning characteristics.
  • non-aerosol, hair styling mousse product which provides a high quality mousse with the desired combination of good initial foam formation, foam breakdown under shear, non-soapiness and easy spreadability, while at the same time not being too sticky. It would also be desirable to provide a non-aerosol hair styling mousse product with improved foaming quality together with good hold, hair feel and conditioning.
  • a mousse which possesses the desired characteristics of good quality foaming, easy spreadability, non-stickiness , hold, feel and conditioning. Consequently it is an object of the present invention to provide a superior non-aerosol hair styling mousse product by incorporating therein a selected mixture of amphoteric surfactant, water-soluble cationic surfactant and polymer resins.
  • a hair styling mousse product comprising a manually-actuable, non-aerosol dispenser equipped with a reservoir, spray head and liquid / air mixing means, which the reservoir contains a hair-styling mousse composition comprising:
  • amphoteric surfactants having the formula (I)
  • R 1 is an alkyl, alkenyl, or hydroxyalkyl radical of from about 8 to about 22 carbon atoms, optionally interupted with up to about 10 ethylene oxide moieties and / or 1 glyceryl moiety
  • R2 and R3 are individually selected from alkyl and monohydroxyalkyl groups containing from about 1 to about 3 carbon atoms
  • 4 is alkylene, or hydroxyalkylene of from about 1 to about 4 carbon atoms
  • Z is a radical selected from carboxylate, sulpho ⁇ ate or sulphate
  • x is 0 or 1
  • n is from about 1 to about 6
  • m is 0 or 1.
  • a non-aerosol hair styling mousse product comprising a manually-actuable dispenser containing a reservoir, dispensing head, and liquid / air mixing means, the reservoir comprising a hair styling mousse composition.
  • the present invention also relates to the mousse composition itself and to use thereof in a manually- actuable dispenser.
  • the hair styling mousse composition of the present invention understood a nonionic, anionic or amphoteric hair setting polymer resin, and / or a cationic 5 hair conditioning polymer resin, an amphoteric surfactant, a water-soluble cationinc surfactant and water or a water / solvent mixture.
  • the hair setting polymer resin is preferabiy present in an amount of from about 0.5% to about 10%, more preferabiy from about 1% to about 5% by weight of composition.
  • Hair setting resins suitable for use herein include any resin soluble or colloidally dispersible in the aqueous phase (if water is the only solvent in the aqueous phase, the resin should be soluble or dispersible in water; if an optional cosolvent such as ethanol is present the resin should be soluble or dispersible in the combined solvent System). Solubility / dispersibility is determined at ambient conditions of temperature and pressure (25 ° C at 1 At).
  • Resins for use in the compositions of the present invention include anionic, nonionic, and amphoteric resins.
  • resins for use herein include polyvinylpyrrolidone, copolymers of polyvinylpyrrolidone and methylmethacrylate, copolymers of polyvinylpyrrolidone and vinylacetate, polyvinyl alcohol, copolymers of polyvinylalcohol and crotonic acid, copolymers of polyvinylalcohol and maleic anhydride, hydroxypropyl cellulose, hydroxypropyl guarene ethylmethacrylate / methacrylic acid terpolymer, octylacrylamide / acrylate / butylaminoethyl methacrylate copolymers, and mixtures thereof.
  • Preferred resins for use in the compositions of the present invention include polyvinylpyrrolidone, copolymers of polyvinylpyrrolidone and vinyl acetate, and mixtures thereof. Such resins are available under the trade name Luviskol (RTM), a most preferred resin being Luviskol VA64 (PVA / VA 60/40).
  • RTM Luviskol
  • VA64 PVA / VA 60/40
  • the mass average molecular weight of the hair setting polymer resin is generally in the range from about 2,000 to about 2,000,000. 6
  • the polycationic hair conditioning polymer resin is preferabiy present in an amount of from about 0.5% to about 10%, preferabiy from about 1% to about 5% by weight of composition.
  • the hair conditioning resins hereof must understood monomers of a cationic character.
  • monomeric units present in the polymers may be referred to as the monomers from which they can be derived.
  • the cationic monomers can be derived from polymerizable cationic starting monomers, or from polymerizable nonionic monomers which are modified subsequent to polymerization to be of cationic character.
  • cationic monomers examples include:
  • (meth) acrylamide derived from (meth) acrylic acid or (meth) acrylamide and a dialkylalkanolami ⁇ e hâve C-1-C4 alkyl groups such as dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylami ⁇ opropyl (meth) acrylate. or dimethylami ⁇ opropyl (meth) acrylamide; and
  • an acid such as hydrochloric acid, or lactic acid
  • modification with a halogenated alkyl such as methyl chloride, ethyl chloride, methyl bromide, or ethyl iodide
  • modification with a halogenated fatty acid ester such as ethyi monochloroacetate, or methyl monochlor
  • the cationic unsaturated monomers include amine derivatives of allyl compounds such as diallyidimethylammonium chloride and the like as well as vinylimidazolium quatemary ammonium monomers.
  • Thiese cationic unsaturated monomers can be polymerized in cationic form, or as an alternative they can be polymerized in the form of their precursors, which are then modified to be cationic, for example, by a quaternizing agent (eg. Ethyl monochloroacetate, dimethyl sulfate, etc.).
  • a quaternizing agent eg. Ethyl monochloroacetate, dimethyl sulfate, etc.
  • Preferred cationic monomers include dimethylami ⁇ oethyl methacrylate, quaternized dimethylaminoethyl methacrylate, diallyldimethyl ammonium chloride, vinylimidazolium quatemary ammonium monomers and mixtures thereof.
  • the hair conditioning polymers hereof should contain at least about 1%, by weight, cationic monomer, preferabiy at least about 2%, more preferabiy at least about 5%.
  • the cationic resins hereof can also contain nonionic monomers includi ⁇ g, both high polarity monomers and low polarity monomers.
  • the cationic resins hereof will generally understood from about 1% to 100% cationic monomers and from 0% to about 99% nonionic monomers, preferabiy from about 2% to about 75% cationic monomers and from about 25% to about 98% S nonionic monomers, more preferabiy from about 5% to about 50% cationic monomers and from about 50% to about 95% nonionic monomers.
  • nonionic mo ⁇ omers are acrylic or methacrylic acid esters of C-1-C24 alcohols, such as methanol, ethanol, 1-propanol, 2-propanol,
  • nonionic monomers include acrylate and methacrylate derivatives such as allyl acrylate and methacrylate, cyclohexyl acrylate and methacrylate, oleyl acrylate and methacrylate, benzyl acrylate and methacrylate, tetrahydrofurfuryl acrylate and methacrylate, ethylene glycol di-acrylate and -methayl -acrylate and -methacrylate, diacetonacrylamide, isobornyl (meth) acrylate, and the like.
  • acrylate and methacrylate derivatives such as allyl acrylate and methacrylate, cyclohexyl acrylate and methacrylate, oleyl acrylate and methacrylate, benzyl acrylate and methacrylate, tetrahydrofurfuryl acrylate and methacrylate, ethylene glycol di-acrylate and -methayl -acrylate and -methacrylate,
  • Preferred nonionic monomers include ⁇ -butyl methacrylate, isobutyl methacrylate, 2-ethyihexyl methacrylate, methyl methacrylate, t-butylacrylate, t-butylmethacrylate, and mixtures thereof. 4
  • Representative polar nonionic monomers include acrylamide, N, N- dimethylacrylamide, methacrylamide, Nt-butyl acrylamide, methacryionitrile, acrylamide, acrylate alcohols (eg. C2-C6 acrylate alcohols such as hydroxyethyl acrylate, hdroxyproxyl acrylate), hydroxyethyl methacrylate, hydroxypropyl vinyl methacr pyrrolidone, vinyl ethers, such as methyl vinyl ether, acyl lactones and vinyl pyridine, allyl alcohols, vinyl alcohols and vinyl caprolactam.
  • acrylate alcohols eg. C2-C6 acrylate alcohols such as hydroxyethyl acrylate, hdroxyproxyl acrylate
  • hydroxyethyl methacrylate hydroxypropyl vinyl methacr pyrrolidone
  • vinyl ethers such as methyl vinyl ether
  • Preferred polycationic polymer resins for use herein include cationic polysaccharides, homopolymers of dimethyldiallyl ammonium chloride, copolymers of dimethyldiallyl ammonium chloride and acrylamide, cationic amino-functional homopolymers and copolymers derived from acrylic acid and / or methacrylic acid, especiaily from alkylaminoalkyl acrylate and methacrylate monomers such as dimethylaminoethyl acrylate and methacrylate, polyalkyle ⁇ e imines and ethoxy polyalkylene imines, vinylimidazolium / vinylpyrrolidone quatemary ammonium copolymers, and mixtures thereof.
  • cationic polymers are cationic guar gums, for example, hydroxyproxyltrimethylammonium guar gum, quaternized cellulose ethers such as copolymers of hydroxyethylcellulose with diallyldimethyl ammonium chloride or with trimethyl ammonium substituted epoxides, homopolymers of lower alkylamino alkyl acrylate or methacrylate monomers (eg dimethyl aminoethylmetcr ) and copolymers thereof with compatible monomers such as N-vinylpyrrolidone or with alkyl methacrylates such as methyl, ethyl, abietyl and oleyl methacrylates and mixtures therof and / or with alkyl acrylates such as methyl and butyl acrylates and mixtures thereof, copolymers of dimethyldiallyl ammonium chloride and acrylamide, homopolymers of / 02115
  • cationic polymers preferred for use herein include hydroxypropyl trimethyl ammonium guar gum (ds of from 0.11 to 0.22) available commercially under the trade names Jaguar C-17 (RTM), and also Jaguar C-16 (RTM), which contains hydroxypropyl substituents (ds of from 0.8-1.1) in addition to the above-specified cationic groups, quaternized cellulose ethers available commercially under the trade names Ucare Polymer JR and Celquat (eg Celquat L200), homopolymers of dimethyldiallyl ammonium chloride available commercially under the trade name Merquat 100, copolymers of dimethyldiallyl ammonium chloride and acrylamide available copolymers commercially under the trade name Merquat 550 and Merquat S, quaternized vinyl pyrrolido ⁇ e / alkylami ⁇ oacrylate or methacrylate copolymers commercially under the trade name Gafquat (RTM), and methylvinylimi
  • amphoteric surfactant is present at a level of from about 0.1% to about 3%, preferabiy from about 0.3% to about 2% by weight of composition.
  • Suitable amphoteric surfactants for use herein hâve the gênerai formula (l)
  • R 1 is an alkyl, alkenyl. or hydroxyalkyl radical of from about 8 to about 22 carbon atoms, optionally interupted with up to about 10 ethylene oxide 1 1 moieties and / or 1 glyceryl moiety
  • R 2 and R 3 are individually selected from alkyl and monohydroxyalkyl groups containing from about 1 to about 3 carbon atoms
  • R 4 is alkylene, or hydroxyalkylene of from about 1 to about 4 carbon atoms
  • Z is a radical selected from carboxylate, sulphonate or sulphate
  • x is 0 or 1
  • n is from about 1 to about 6
  • m is 0 or.
  • x is 0 or 1
  • n is from about 1 to about 3
  • Z is carboxylate
  • R 1 is an alkyl, alkenyl, or hydroxy radical of from about 8 to about 18 carbon atoms.
  • Z is carboxylate
  • the formula (I) covers a class of compounds known generally as betaines.
  • betaines useful herein include the high alkyl betaines, such as coco dimethyl carboxymethyl betaine, cocoamidopropyl betaine, cocobetaine, lauryl amidopropyl betaine, oleyl betaine, lauryl dimethyl carboxymethyl betaine, lauryl dimethyl alphacarboxyethyl betaine, cetyl dimethyl carboxymethyl betaine, lauryl bis- (2 -hydroxyethyl) carboxymethyl betaine, stearyl bis- (2-hydroxypropyl) carboxymethyl betaine, oleyl dimethyl gamma- carboxypropyi betaine, and lauryl bis- (2-hydroxypropyl) alpha-carboxyethyl betaine, and mixtures thereof.
  • Preferred betaines for use in the present compositions are coco amidopropyl betaine, coco betaine, lauryl amidopropyl betaine, and oleyl betaine.
  • a most preferred betaine is coco amidopropyl betaine.
  • amphoteric surfactants for use in the compositions of the invention include:
  • R- is C7-C22 alkyl or alkenyl
  • R2 is hydrogen or CH2Z
  • each Z is independently CO2M or CH2CO2M
  • M is H, alkali metal, alkaline earth metal, ammonium or alkanolammonium; and / or ammonium derivatives of formula (III)
  • R- * , R2 and Z are as defined above;
  • n and m are numbers from 1 to 4, and R-
  • and M are independently selected from the groups specified above;
  • Suitable amphoteric surfactants of type (a) are marketed under the trade name Miranol (RTM) and are understood to comprise a complex mixture of species.
  • RTM Miranol
  • Traditionally the Miranols hâve been described as having the gênerai formula II, although the CTFA Cosmetic Ingredient Dictionary, 3rd Edition indicates the non-cyclic structure III.
  • CTFA Cosmetic Ingredient Dictionary, 3rd Edition indicates the non-cyclic structure III.
  • amphoteric surfactants of type (a) include compounds of formula II and / or III in which R-
  • Z is CO2M and R2 is H; the compounds in which R-
  • materials preferred for use in the present invention include cocoamphocarboxypropionate, cocoamphocarboxy propionic acid, and especially cocoamphoacetate and cocoamphodiacetate (otherwise referred to as cocoamphocarboxyglycinate).
  • materials preferred for use in the present invention include cocoamphocarboxypropionate, cocoamphocarboxy propionic acid, and especially cocoamphoacetate and cocoamphodiacetate (otherwise referred to as cocoamphocarboxyglycinate).
  • Specify commercial products include those sold under the trade names of Empigen CDL60 and CDR 60 (Albright & Wilson), Miranol C2M Conc. N.P., Miranol C2M Conc.
  • Miranol C2M SF Miranol CM Spécial (Miranol, Inc.); Alkateric 2CIB (Alkaril Chemicals); Amphoterge W-2 (Lonza, Inc.); Monateric CDX-38, Monateric CSH-32 (Mona Industries); Rewoteric AM-2C (Rewo Chemical Group); and Schercotic MS-2 (Scher Chemicals).
  • amphoteric surfactants of type (b) include salts, especially the triethanolammonium salts and salts of N-lauryl-beta-amino / 021
  • Cationic surfactants useful in compositions of the present invention are water-soluble and contain amino or quatemary ammonium hydrophilic moieties which are positively charged when dissolved in the aqueous composition of the present invention.
  • Preferabiy the cationic surfactant has a critical micelle concentration for the pure material (CMC) of greater than 200 ppm measured at 30 ° C in distilled water.
  • CMC pure material
  • Literature values are taken where possible, especially surface tension or conductimetric values - see Critical Micelle Concentrations of Aqueous Surfactant Systems, P. Mukerjee and K.J. Mysels, NSRDS-NBS 36, (1971).
  • Cationic surfactants materials among those useful herein are disclosed in the following documents: M.C.
  • quatemary ammonium-co ⁇ taini ⁇ g cationic surfactant materials useful herein are those of the gênerai formula (VI):

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Abstract

Ce procédé, après l'étape de réduction à l'aide de cystéamine ou l'un de ses sels et après l'étape d'oxydation, consiste à appliquer sur les cheveux une composition de post-traitement contenant en association dans un véhicule cosmétique approprié, (i) soit au moins un acide minéral ou un mélange tampon en une proportion telle que le pH de ladite composition soit compris entre 3,5 et 5,5, soit un acide organique en une proportion comprise entre 0,1 et 10 % par rapport au poids total de la composition, et (ii) au moins un composé organique odorant synthétique. Ce procédé permet de prévenir de façon efficace l'apparition des mauvaises odeurs dues aux produits de dégradation de la cystéamine ou de l'un de ses sels.

Description

Hair Cosmetic
Technical Field
The présent invention reiates to hair styling mousse products. In particular it relates to non-aerosol hair styling mousse products which provide optimum foaming, hair setting, hair feel and hair conditioning characteristics while reducing stickiness and being easily spreadable on the hair.
Backαround of the Invention
The désire to hâve hair retain a particular shape or configuration is one that is widely held. It is possible to alter the shape of the hair either permanently or temporarily. Permanent altération invoives the use of chemical agents to react with the hair in order to achieve the desired effect. This process can be carried out at either room or elevated température.
The temporary set given to hair is, as the term indicates, a temporary arrangement which can be removed by water or by shampooing. The materials used to provide the set hâve generally been resins or gums. The temporary set compositions hâve taken the form of gels, lotions and sprays as well as others. The compositions are applied most often to hair dampened with water, combed or by other means spread through the hair and let dry. The set given will vary depending on the materials used.
In récent years a form of a temporary set has been achieved by means of an aérosol foam - a mousse. The gênerai appeal of mousses can be largely attributed to the ease of application and controlled amount of product which are possible from mousse formulations. Mousse formulations can easily be worked through the hair and can provide a set comparable to that given by a gel or a lotion. Thèse products are generally applied to the user's hand and worked through the hair.
The conventional hair styling mousse generally utilizes a water soluble polymer, water, possibly a conditioning agent, an emulsifier, aesthetic agents and the propellant. More recently, however, due to an increasing public awareness of the effects of volatile orgaπic compounds, such as aérosol propellants, on the enviroπment, hair styling mousse products hâve been formulated without a propellant and dispensed from a manually-actuable container so as to be of the non-aerosol type. Unfortunately, however, there are a number of problems associated with non-aerosol products. In particular they provide mousses which are of poor foam quality and stability and which are undesirably sticky. Moreover, many of thèse formulations are lacking in hair holding, hair feel or hair conditioning characteristics.
It would be désirable to provide a non-aerosol, hair styling mousse product which provides a high quality mousse with the desired combination of good initial foam formation, foam breakdown under shear, non-soapiness and easy spreadability, while at the same time not being too sticky. It would also be désirable to provide a non-aerosol hair styling mousse product with improved foaming quality together with good hold, hair feel and conditioning.
It has πow been fouπd that by iπcluding an amphoteric surfactant and a water- soluble cationic surfactant in a πoπ-aerosol mousse composition containiπg certain polymer resins, a mousse is provided which possesses the desired characteristics of good quality foaming, easy spreadability, non-stickiness, hold, feel and conditioning. Accordingly it is an object of the présent invention to provide a superior non- aerosol hair styling mousse product by incorporating therein a selected mixture of amphoteric surfactant, water-soluble cationic surfactant and polymer resins.
AH percentages and ratios used herein are by weight unless otherwise specified.
Summary of the Invention
According to one aspect of the présent invention there is provided a hair styling mousse product comprising a manually-actuable, non-aerosol dispenser equipped with a réservoir, spray head and liquid/air mixing means, wherein the réservoir contains a hair-styling mousse composition comprising:
(i) from about 0.5 % to about 10 % by weight of composition of a nonionic, amphoteric or anionic hair setting polymer resin, and/or
(ii) from about 0.5 % to about 10 % by weight of composition of a polycationic hair conditioning polymer resin,
(iii) from about 0.1 % to about 3 % by weight of composition of an . amphoteric surfactant,
(iv) from about 0.01 % to about 1 % by weight of composition of a water-soluble cationic surfactant, and 4
(v) water or a water/solvent mixture.
Highly preferred herein are amphoteric surfactants having the formula (I)
R2
R1 [ CONH ( CH2 ) n ] χN ( + ) — CH2 (R4 ) mZ ( - )
R3
wherein R1 is an alkyl, alkenyl, or hydroxyalkyl radical of from about 8 to about 22 carbon atoms, optionally interupted with up to about 10 ethylene oxide moieties and/or 1 glyceryl moiety, R2 and R3 are individually selected from alkyl and monohydroxyalkyl groups containing from about 1 to about 3 carbon atoms, 4 is alkylene, or hydroxyalkylene of from about 1 to about 4 carbon atoms, Z is a radical selected from carboxylate, sulphoπate or sulphate, x is 0 or 1 , n is from about 1 to about 6, and m is 0 or 1.
Detailed Description of the Invention
In accordance with one aspect of the présent invention a non-aerosol hair styling mousse product is formed comprising a manually-actuable dispenser containing a réservoir, dispensing head, and liquid/air mixing means, the réservoir comprising a hair styling mousse composition. The présent invention also relates to the mousse composition itself and to use thereof in a manually- actuable dispenser.
The hair styling mousse composition of the présent invention comprises a nonionic, anionic or amphoteric hair setting polymer resin, and/or a cationic 5 hair conditioning polymer resin, an amphoteric surfactant, a water-soluble cationinc surfactant and water or a water/solvent mixture.
The hair setting polymer resin is preferabiy présent in an amount of from about 0.5 % to about 10 %, more preferabiy from about 1 % to about 5 % by weight of composition. Hair setting resins suitable for use herein include any resin soluble or colloidally dispersible in the aqueous phase (if water is the only solvent in the aqueous phase, the resin should be soluble or dispersible in water; if an optional cosolvent such as ethanol is présent the resin should be soluble or dispersible in the combined solvent System). Solubility/dispersibility is determined at ambient conditions of température and pressure (25°C at 1 At). Resins for use in the compositions of the présent invention include anionic, nonionic, and amphoteric resins. Spécifie resins for use herein include polyvinylpyrrolidone, copolymers of polyvinylpyrrolidone and methylmethacrylate, copolymers of polyvinylpyrrolidone and vinylacetate, polyvinyl alcohol, copolymers of polyvinylalcohol and crotonic acid, copolymers of polyvinylalcohol and maleic anhydride, hydroxypropyl cellulose, hydroxypropyl guar gum, sodium polystyrène sulfonate, polyvinylpyrrolidone/ethylmethacrylate/methacrylic acid terpolymer, octylacrylamide/acrylate/butylaminoethyl methacrylate copolymers, and mixtures thereof. Preferred resins for use in the compositions of the présent invention include polyvinylpyrrolidone, copolymers of polyvinylpyrrolidone and vinyl acétate, and mixtures thereof. Such resins are available under the trade name Luviskol (RTM), a most preferred resin being Luviskol VA64 (PVA/VA 60/40). The mass average molecular weight of the hair setting polymer resin is generally in the range from about 2.000 to about 2,000,000. 6
The polycationic hair conditioning polymer resin is preferabiy présent in an amount of from about 0.5 % to about 10 %, preferabiy from about 1 % to about 5 % by weight of composition. As an essential aspect, the hair conditioning resins hereof must comprise monomers of a cationic character. For convenience in describing the polymers hereof, monomeric units présent in the polymers may be referred to as the monomers from which they can be derived. The cationic monomers can be derived from polymerizable cationic starting monomers, or from polymerizable nonionic monomers which are modified subséquent to polymerization to be of cationic character.
Examples of the cationic monomers include:
(i) monomers derived from acrylic acid or methacryiic acid, which is referred to hereinafter collectively as (meth)acryiic acid, and a quaternarized epihalohydrin product of a trialkyl aminé having 1 to 5 carbon atoms in the alkyl group such as (methy)acryloxypropyltrimethylammonium chloride and (meth)acryioxypropyltriethylammonium bromide;
(ii) aminé derivatives of (meth)acrylic acid or aminé derivatives of
(meth)acrylamide derived from (meth)acrylic acid or (meth)acrylamide and a dialkylalkanolamiπe hâve C-1-C4 alkyl groups such as dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylamiπopropyl (meth)acrylate. or dimethylamiπopropyl (meth)acrylamide; and
(iii) derivatives of the products of the group (ii) above by (1) neutralization with an acid such as hydrochloric acid, or lactic acid, (2) modification with a halogenated alkyl, such as methyl chloride, ethyl chloride, methyl bromide, or ethyl iodide, (3) modification with a halogenated fatty acid ester such as ethyi monochloroacetate, or methyl monochloropropionate, and (4) modification with a dialkyl sulfate such as dimethyl sulfate, or diethyl sulfate.
Furthermore, the cationic unsaturated monomers include aminé derivatives of allyl compounds such as diallyidimethylammonium chloride and the like as weil as vinylimidazolium quatemary ammonium monomers.
Thèse cationic unsaturated monomers can be polymerized in cationic form, or as an alternative they can be polymerized in the form of their precursors, which are then modified to be cationic, for example, by a quaternizing agent (eg. ethyl monochloroacetate, dimethyl sulfate, etc.).
Preferred cationic monomers include dimethylamiπoethyl methacrylate, quaternized dimethylaminoethyl methacrylate, diallyldimethyl ammonium chloride, vinylimidazolium quatemary ammonium monomers and mixtures thereof.
The hair conditioning polymers hereof should contain at least about 1%, by weight, cationic monomer, preferabiy at least about 2%, more preferabiy at least about 5%.The cationic resins hereof can also contain nonionic monomers includiπg, both high polarity monomers and low polarity monomers. The cationic resins hereof will generally comprise from about 1% to 100% cationic monomers and from 0% to about 99% nonionic monomers, preferabiy from about 2% to about 75% cationic monomers and from about 25% to about 98% S nonionic monomers, more preferabiy from about 5% to about 50% cationic monomers and from about 50% to about 95% nonionic monomers.
Représentative examples nonionic moπomers are acrylic or methacrylic acid esters of C-1-C24 alcohols, such as methanol, ethanol, 1-propanol, 2-propanol,
1-butanol, 2-methyl-1-propanol, 1-peπtanol, 2-pentanol, 3-pentanol, 2-methyl- 1-butanol, 1-methyl-1-butanol, 3-methyl-1-butanol, 1-methyl-l-pentanol, 2- methyi-1-pentanol, 3-methyl-1-pentanol, t-butanol, cyclohexanol, 2-ethyl-1- butanol, 3-heptanol, beπzyl alcohol, 2-octanol, S-methyl-1-heptanol, 2-ethyl-1- hexaπol, 3,5-dimethyl-1-hexanol, 3,5,5-trimethyl-l-hexaπol, 1-decanol, 1- dodecanol, 1-hexadecanol, 1-octadecanol, and the like, the alcohols having from about 1-24 preferabiy from about 4-18, more preferabiy from about 4-12 carbon atoms; styrène; chiorostyrene; vinyl esters such as vinyl acétate; vinyl chloride; vinylidene chloride; acrylonitrile; alpha-methylstyrene; t-butylstyrene; butadiene; cyclohexadiene; ethylene; propylene; vinyl toluène; alkoxyalkyl (meth)acrylate, such as methoxy ethyl (meth)acrylate and butoxyethyl (meth)acrylate; and mixtures thereof. Other nonionic monomers include acrylate and methacrylate derivatives such as allyl acrylate and methacrylate, cyclohexyl acrylate and methacrylate, oleyl acrylate and methacrylate, benzyl acrylate and methacrylate, tetrahydrofurfuryl acrylate and methacrylate, ethylene glycol di-acrylate and -methacrylate, 1,3-butyleneglycol di-acrylate and -methacrylate, diacetonacrylamide, isobornyl (meth)acrylate, and the like.
Preferred nonionic monomers include π-butyl methacrylate, isobutyl methacrylate, 2-ethyihexyl methacrylate, methyl methacrylate, t-butylacrylate, t-butylmethacrylate, and mixtures thereof. 4
Représentative polar nonionic monomers include acrylamide, N,N- dimethylacrylamide, methacrylamide, N-t-butyl acrylamide, methacryionitrile, acrylamide, acrylate alcohols (eg. C2-C6 acrylate alcohols such as hydroxyethyl acrylate, hdroxyproxyl acrylate), hydroxyethyl methacrylate, hydroxypropyl methacrylate, vinyl pyrrolidone, vinyl ethers, such as methyl vinyl ether, acyl lactones and vinyl pyridine, allyl alcohols, vinyl alcohols and vinyl caprolactam.
Preferred polycationic polymer resins for use herein include cationic polysaccharides, homopolymers of dimethyldiallyl ammonium chloride, copolymers of dimethyldiallyl ammonium chloride and acrylamide, cationic amino-functional homopolymers and copolymers derived from acrylic acid and/or methacrylic acid, especiaily from alkylaminoalkyl acrylate and methacrylate monomers such as dimethylaminoethyl acrylate and methacrylate, polyalkyleπe imines and ethoxy polyalkylene imines, vinylimidazolium/vinylpyrrolidone quatemary ammonium copolymers, and mixtures thereof.
Of thèse, preferred cationic polymers are cationic guar gums, for example, hydroxyproxyltrimethylammonium guar gum, quaternized cellulose ethers such as copolymers of hydroxyethylcellulose with diallyldimethyl ammonium chloride or with trimethyl ammonium substituted epoxides, homopolymers of lower alkylamino alkyl acrylate or methacrylate monomers (e.g. dimethyl aminoethylmethacrylate) and copolymers thereof with compatible monomers such as N-vinylpyrrolidone or with alkyl methacrylates such as methyl , ethyl, abietyl and oleyl methacrylates and mixtures therof and/or with alkyl acrylates such as methyl and butyl acrylates and mixtures thereof, copolymers of dimethyldiallyl ammonium chloride and acrylamide, homopolymers of /02115
10 dimethyldiallyl ammonium chloride, vinylimidazolium/vinyl pyrrolidone copolymers, and mixtures thereof.
By way of exemplification, cationic polymers preferred for use herein include hydroxypropyl trimethyl ammonium guar gum (d.s. of from 0.11 to 0.22) available commercially under the trade names Jaguar C-17(RTM), and also Jaguar C-16(RTM), which contains hydroxypropyl substituents (d.s. of from 0.8-1.1) in addition to the above-specified cationic groups, quaternized cellulose ethers available commercially under the trade names Ucare Polymer JR and Celquat (e.g. Celquat L200), homopolymers of dimethyldiallyl ammonium chloride available commercially under the trade name Merquat 100, copolymers of dimethyldiallyl ammonium chloride and acrylamide available copolymers commercially under the trade name Merquat 550 and Merquat S, quaternized vinyl pyrrolidoπe/alkylamiπoacrylate or methacrylate copolymers commercially under the trade name Gafquat (RTM), and methylvinylimidazolium/vinylpyrrolidone quatemary ammonium copolymers commercially available under the tradename Luviquat(RTM).
The amphoteric surfactant is présent at a level of from about 0.1 % to about 3 %, preferabiy from about 0.3 % to about 2 % by weight of composition. Suitable amphoteric surfactants for use herein hâve the gênerai formula (l)
R'
R1[CONH(CH2)n] )—CH2(R4)mZ(-)
Figure imgf000012_0001
wherein R1 is an alkyl, alkenyl. or hydroxyalkyl radical of from about 8 to about 22 carbon atoms, optionally interupted with up to about 10 ethylene oxide 1 1 moieties and/or 1 glyceryl moiety, R2 and R3 are individually selected from alkyl and monohydroxyalkyl groups containing from about 1 to about 3 carbon atoms, R4 is alkylene, or hydroxyalkylene of from about 1 to about 4 carbon atoms, Z is a radical selected from carboxylate, sulphonate or sulphate, x is 0 or 1 , n is from about 1 to about 6, and m is 0 or . Preferabiy, x is 0 or 1 , n is from about 1 to about 3, Z is carboxylate, and R1 is an alkyl, alkenyl, or hydroxy radical of from about 8 to about 18 carbon atoms. When Z is carboxylate, the formula (I) covers a class of compounds known generally as betaines.
Examples of betaines useful herein include the high alkyl betaines, such as coco dimethyl carboxymethyl betaine, cocoamidopropyl betaine, cocobetaine, lauryl amidopropyl betaine, oleyl betaine, lauryl dimethyl carboxymethyl betaine, lauryl dimethyl alphacarboxyethyl betaine, cetyl dimethyl carboxymethyl betaine, lauryl bis-(2-hydroxyethyl) carboxymethyl betaine, stearyl bis-(2-hydroxypropyl) carboxymethyl betaine, oleyl dimethyl gamma- carboxypropyi betaine, and lauryl bis-(2-hydroxypropyl) alpha-carboxyethyl betaine, and mixtures thereof. Preferred betaines for use in the présent compositions are coco amidopropyl betaine, coco betaine, lauryl amidopropyl betaine, and oleyl betaine. A most preferred betaine is coco amidopropyl betaine.
Other suitable amphoteric surfactants for use in the compositions of the invention include:
(a) imidazolinium surfactants of formula (II) 12
Figure imgf000014_0001
wherein R-| is C7-C22 alkyl or alkenyl, R2 is hydrogen or CH2Z, each Z is independently CO2M or CH2CO2M, and M is H, alkali métal, alkaline earth métal, ammonium or alkanolammonium; and/or ammonium derivatives of formula (III)
Figure imgf000014_0002
R2
wherein R-* , R2 and Z are as defined above;
(b) aminoalkanoates of formula (IV)
R-( NH(CH2)nCθ2M
and iminodialkanoates of formula (V)
Rl N[(CH2) CO2M]2
wherein n and m are numbers from 1 to 4, and R-| and M are independently selected from the groups specified above; and
(c) mixtures thereof. 13
Suitable amphoteric surfactants of type (a) are marketed under the trade name Miranol (RTM) and are understood to comprise a complex mixture of species. Traditionally, the Miranols hâve been described as having the gênerai formula II, although the CTFA Cosmetic Ingrédient Dictionary, 3rd Edition indicates the non-cyclic structure III. In practice, a complex mixture of cyclic and non-cyclic species is likely to exist and both définitions are given hère for sake of completeness. Preferred for use herein, however, are the non-cyclic species.
Examples of suitable amphoteric surfactants of type (a) include compounds of formula II and/or III in which R-| is CgH-(7 (especially iso-capryl), CgH-jg and
C-| 1 H23 alkyl. Especially preferred are the compounds in which R-| is CgH-jg,
Z is CO2M and R2 is H; the compounds in which R-| is C-| 1 H23, Z is CO2M and R2 is CH2CO2M; and the compounds in which R-| is C-* 1 H23, Z is CO2M and R2 is H.
In CTFA nomenclature, materials preferred for use in the présent invention include cocoamphocarboxypropionate, cocoamphocarboxy propionic acid, and especially cocoamphoacetate and cocoamphodiacetate (otherwise referred to as cocoamphocarboxyglycinate). Spécifie commercial products include those sold under the trade names of Empigen CDL60 and CDR 60 (Albright & Wilson), Miranol C2M Conc. N.P., Miranol C2M Conc. O.P., Miranol C2M SF, Miranol CM Spécial (Miranol, Inc.); Alkateric 2CIB (Alkaril Chemicals); Amphoterge W-2 (Lonza, Inc.); Monateric CDX-38, Monateric CSH-32 (Mona Industries); Rewoteric AM-2C (Rewo Chemical Group); and Schercotic MS-2 (Scher Chemicals).
Examples of suitable amphoteric surfactants of type (b) include salts, especially the triethanolammonium salts and salts of N-lauryl-beta-amino /021
14 propionic acid and N-lauryl-imiπo-dipropionic acid. Such materials are sold under the trade name Deriphat by General Mills and Mirataiπe by Miranol Inc. Amphoterics preferred for use herein, however, are those of formula II and/or
Cationic surfactants useful in compositions of the présent invention are water- soluble and contain amino or quatemary ammonium hydrophilic moieties which are positively charged when dissolved in the aqueous composition of the présent invention. Preferabiy the cationic surfactant has a critical micelle concentration for the pure material (CMC) of greater than 200 ppm measured at 30°C in distilled water. Literature values are taken where possible, especially surface tension or conductimetric values - see Critical Micelle Concentrations of Aqueous Surfactant Systems, P. Mukerjee and K.J. Mysels, NSRDS-NBS 36, (1971). Cationic surfactants materials among those useful herein are disclosed in the following documents: M.C. Publishing Co., McCutcheon's, Détergents & Emulsifiers, (North American édition 1979); Schwartz, et al., Surface Active Agents, Their Chemistry and Technology, New York: Iπterscience Publishers, 1949; U.S. Pat. No. 3,155,591 , Hiifer, issued Nov. 3, 1964; U.S. Pat No. 3,929,678, Laughlin, et al., issued Dec. 30, 1975; U.S. Pat No. 3,959,461 , Bailey, et al., issed May 25, 1976; and U.S. Pat. No. 4,387,090, Bolich, Jr., issued June 7, 1983.
Among the quatemary ammonium-coπtainiπg cationic surfactant materials useful herein are those of the gênerai formula (VI):
?2
R: N ( + ) — R2 χ ( - )
R2

Claims

1 wherein R-) is selected from C8-C20. preferabiy C-|n-C-|6 alkyl, alkenyl and alkaryl groups; each R2 is independently selected from C-1-C4 alkyl, hydroxyalkyl and benzyl groups, and X is an anioπ selected from halogen, acétate, phosphate, nitrate and alkylsulphate radicals. The aliphatic groups may contain, in addition to carbon and hydrogen atoms, ether linkages, and other groups such as amido groups. Preferred surfactants of this class include the cetyl trimethyl ammonium halides.
Other quatemary ammonium salts useful herein are diquatemary ammonium salts, such as those of the formula (VII):
R.
(+) ( CH2 ) 3 N ( + ) R-, 2X ( -)
R2 R2
wherein R-j , R2 and X are as defined above. Such quatemary ammonium salts include, for example, tallow propane diammonium dichloride.
The compositions also comprise water or a water/solvent mixture. Suitable solvents include lower (e.g. C-j-Cβ) alcohols and polyols such as isopropyl alcohol, propylene glycol, ethanol, hexylene glycol, glycérine, propane diois, etc.
The mousse compositions of the présent invention can also contain a variety of non-essential, optional components such as preservatives, emulsifiers, block polymers, thickeners and viscosity modifiers, fatty alcohols, pH adjusting agents, colouring agents, hair oxidizing agents, hair reducing agents, perfume oils, perfume solubilizing agents, sequestering agents, polymer plasticizing /02115
H) agents and volatile and non-volatile silicone fluids. Such conventional optional ingrédients are weil known to a person skilled in the art, e.g. preservatives such as benzyl alcohol, methyl paraben, propyl paraben, imidazolidinyl urea, and DMDM Hydantoin; emulsifiers such as anionics (e.g., sodium alkyl sulphate) and nonionics (aminé oxides); thickeners and viscosity modifiers such as diethanolamides of long chaiπ fatty acids; block polymers of ethylene oxide and propylene oxide such as Pluronic (RTM) F88 offered by BASF Wyandotte; fatty alcohols such as cetearyl alcohol; viscosity modifiers such as sodium chloride, sodium sulphate, and ethyl alcohol; pH adjusting agents such as citric acid, succinic acid, sodium hydroxide and triethanoiamine; colouring agents such as aπy of the FD & C or D & C dyes; hair oxidizing (bleaching) agents such as hydrogen peroxide, perborate salts and persulphate salts; hair reducing agents such as the thioglycolates; perfume oils such as Florasynth (RTM) perfumes; perfume oil solubilizers such as polyethylene glycol fatty acid esters; sequestering agents such as ethylenediamine tetraacteic acid; and, among many other agents, polymer plasticizing agents such as glycerin and propylene glycol. Thèse optional materials can be présent at a level of from about 0.01 % to about 10 %, preferabiy from about 0.5 % to about 5 % by weight of composition.
The mousse compositions are dispensed using a manually-actuable, non- aerosol dispenser such as a pump-actuated or compressible dispenser. Compressible, non-aerosol dispenser of the so-called "squeeze-foamer" type comprise a réservoir, a dispensiπg head, liquid/air mixing means and preferabiy, homogeπizing means and πon-return valve means.
Squeeze foamer packages are weil known as exemplified by the disclosures in the following patents: 17
US-A-3,709,437 (Wright, issued January 9th, 1973);
US-A-3,937,364 (Wright, issued February 10th, 1976);
US-A-4,022,351 (Wright, issued May 10th, 1977);
US-A-4, 147,306 (Bennett, issued April 3rd, 1979);
US-A-4, 184,615 (Wright, issued January 22nd, 1980);
US-A-4,598,862 (Rice, issued July 8th, 1986);
US-A-4,615,467 (Grogan et al., issued October 7th, 1986); and FR-A-2,604,622 (Verlhulst, published April 8th, 1988).
The above packages do not use any propellant and are therefore safe for the consumer and the environmeπt. The mousse composition is placed in the container réservoir which may for instance, take the form of a plastic squeeze bottle. Squeezing the container réservoir with the hand forces the composition through liquid/air mixing means where the composition is mixed with air and then preferabiy through a homogeniziπg means that makes the foam more homogeneous and controls the coπsistency of the foam. The foam is then discharged as a uniform, πoπ-pressurized aerated foam through the dispensing head of the dispenser.
The minimum force to activate the squeeze foamer is about 1 psig, preferabiy from about 2 psig to about 15 psig. The minimum force is related to the size of the chanπels in the dispenser, the viscosity of the composition, etc. In gênerai, the density of the foam should be between about 0.002 and about 0.25 g/cc, preferabiy between about 0.01 and about 0.07 g/cc. Foam density is inversely related to foam creaminess so lower foam densities are preferred. 18
The mousse compositions herein can also be packaged in a pump-actuated non-aerosol dispenser of the so-called "pump-foamer" type which comprise a réservoir, a dispeπsing head, pump means, liquid/air mixing means and preferabiy homogenising means and non-return valve means.
Highly preferred for use herein is a pump foamer pack as described in Japanese Utility Model 1-66900. In brief, the pump foam dispenser comprises a manually actuated, spriπg-mounted piston tube arraπged for reciprocal, up and down movement withiπ a air/liquid cylinder, wherein the piston tube and the upper large diameter part of the cylinder together act as an air pump and wherein the piston tub and the lower, small diameter part of the cylinder together act as a liquid pump. The liquid and air pumps are synchronized by the common piston mechanism. The pumping action is controlled by means of three check valves, a first check valve which régulâtes eπtry of liquid from the réservoir into the liquid cylinder, a second check valve which régulâtes entry of air into the air cylinder, and a third check valve which régulâtes discharge of liquid from the liquid cylinder to a liquid/air mixing chamber. The liquid/air mixing chamber preferabiy iπcludes a homogenizing means which makes the generated foam more homogeneous and controls the consistency of the foam. The foam is then discharged as a uniform noπ-pressurized aerated foam through the dispensiπg head of the dispenser.
In gênerai, the density of the foam should be between about 0.002 and about 0.25 g/cc, preferabiy between about 0.01 and about 0.07 g/cc. Foam density can be controlled by regulating the air/liquid ratio of the dispenser which is preferabiy at least 20:1 , more preferabiy at least 40:1. A preferred method of regulating air/liquid ratio is by preaerating the liquid entering the liquid cylinder, for example, by introducing a small air bleed hole in the dip-tube which 19 connects the liquid cylinder to the liquid réservoir. Thus, introducing a 0.6 mm bleed hole at a point approximately 3 mm below the first check valve (ie. above the normal liquid level in the réservoir) increases the air to liquid ratio from approximately 20:1 up to about 50:1.
The présent compositions are emitted from the non-aerosol dispenser as a foam which is worked through the hair with the fingers or a hair styling implement and either left on the hair or rinsed out.
PCT/FR1993/000756 1992-07-23 1993-07-23 Procede de prevention de formation de mauvaises odeurs dans une operation de deformation permanente des cheveux et composition pour sa mise en ×uvre Ceased WO1994002114A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2535038A2 (fr) 2011-04-21 2012-12-19 PZ Cussons (International) Limited Composition de mise en forme des cheveux et méthode de coiffage
KR20180081816A (ko) * 2015-12-23 2018-07-17 로레알 모발 형태의 형성 또는 변형을 위한 조성물 및 방법

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Publication number Priority date Publication date Assignee Title
EP0362663A1 (fr) * 1988-10-04 1990-04-11 Henkel Kommanditgesellschaft auf Aktien Composition d'ondulation des cheveux
FR2681227A1 (fr) * 1991-09-13 1993-03-19 Oreal Procede de deformation permanente des cheveux de generant pas d'odeur desagreable.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0362663A1 (fr) * 1988-10-04 1990-04-11 Henkel Kommanditgesellschaft auf Aktien Composition d'ondulation des cheveux
FR2681227A1 (fr) * 1991-09-13 1993-03-19 Oreal Procede de deformation permanente des cheveux de generant pas d'odeur desagreable.

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Title
PATENT ABSTRACTS OF JAPAN vol. 10, no. 31 (C-327) *
PATENT ABSTRACTS OF JAPAN vol. 16, no. 81 (C-915) *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2535038A2 (fr) 2011-04-21 2012-12-19 PZ Cussons (International) Limited Composition de mise en forme des cheveux et méthode de coiffage
KR20180081816A (ko) * 2015-12-23 2018-07-17 로레알 모발 형태의 형성 또는 변형을 위한 조성물 및 방법
KR102184572B1 (ko) * 2015-12-23 2020-12-01 로레알 모발 형태의 형성 또는 변형을 위한 조성물 및 방법

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