WO2001035916A1 - Compositions de teinture contenant une association de deux polyethers polyurethanes - Google Patents
Compositions de teinture contenant une association de deux polyethers polyurethanes Download PDFInfo
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- WO2001035916A1 WO2001035916A1 PCT/FR2000/002902 FR0002902W WO0135916A1 WO 2001035916 A1 WO2001035916 A1 WO 2001035916A1 FR 0002902 W FR0002902 W FR 0002902W WO 0135916 A1 WO0135916 A1 WO 0135916A1
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- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/87—Polyurethanes
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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
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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
- A61Q5/10—Preparations for permanently dyeing the hair
Definitions
- the present invention relates to compositions for dyeing keratin fibers and in particular human keratin fibers such as the hair, comprising at least two specific polyether polyurethanes, as well as the methods and devices implementing said compositions.
- the first is semi-permanent or temporary coloring, or direct coloring, which uses dyes capable of bringing to the natural coloring of the hair, a more or less marked change in color possibly resistant to several shampoos. These dyes are called direct dyes; they can be used with or without an oxidizing agent. In the presence of an oxidant, the aim is to obtain a direct lightening coloration.
- the lightening coloration is implemented by applying to the hair the extemporaneous mixture of a direct dye and an oxidant and makes it possible in particular to obtain, by lightening the melanin of the hair, an advantageous effect such as a solid color in in the case of gray hair or to bring out the color in the case of naturally pigmented hair.
- the second is permanent coloring or oxidation coloring.
- oxidation dyes comprising the oxidation coloring precursors and the couplers.
- the oxidation coloring precursors commonly called “oxidation bases”
- oxidation bases are initially colorless or weakly colored compounds which develop their dyeing power within the hair in the presence of oxidizing agents added at the time of use, by conducting to the formation of colored and coloring compounds.
- the formation of these colored and coloring compounds ' results either from an oxidative condensation of the "oxidation bases” on themselves, or from an oxidative condensation of the "oxidation bases” on color-modifying compounds called commonly “couplers" and generally present in the dye compositions used in oxidation dyeing.
- EP-875237 and WO99 / 36047 and more particularly the commercial products sold by the company ROHM & HAAS under the trade names ACULYN 46 and ACULYN 44.
- the so-called "permanent" coloration obtained by means of these oxidation dyes must satisfy a certain number of requirements. Thus, it must be harmless from the toxicological point of view; it must make it possible to obtain nuances in the desired intensity and have good resistance to external agents (light, bad weather, washing, permanent waving, perspiration, friction).
- the dyes must also make it possible to cover white hair, and be the least selective possible, that is to say allow to obtain the smallest possible discoloration differences throughout a same keratin fiber, which can be indeed differently sensitized (ie damaged) between its tip and its root. Finally, the dye, whether direct or permanent, must be able to restore the natural shine of the hair.
- the dyeing compositions obtained according to the invention have excellent rheological properties allowing optimal application to the fibers. They also have a very smooth and homogeneous texture allowing a regular flow at the outlet of the packaging articles.
- compositions when the polyether polyurethanes are used within well-defined limits, make it possible to synergistically improve the shine of the hair.
- a subject of the present invention is therefore a composition for dyeing keratin fibers, in particular human keratin fibers, such as the hair, comprising, in a medium suitable for dyeing, at least one dye, and characterized in that it contains at least the association:
- a polyether polyurethane capable of being obtained by polycondensation of at least three compounds comprising (i) at least one polyethyieneglycol comprising from 50 to 500 moles of ethylene oxide,
- polyurethane polyether capable of being obtained by polycondensation of at least three compounds comprising (i) at least one polyethyieneglycol comprising from 50 to 500 moles of ethylene oxide, (ii) at least one alcohol fatty C8-C30 different from that of polyether polyurethane (a) and (iii) at least one diisocyanate.
- polyether polyurethanes (a) and (b) will be used for which the polyethylene glycol contains 150 or 180 moles of ethylene oxide. Also preferably, use will be made of a polyurethane polyether (a) or (b) associated with a saccharide and more particularly with maltodextrin. Still preferably, polyether polyurethanes (a) and (b) will be used for which the diisocyanate is methylene bis (4-cyclohexylisocyanate).
- a more particularly preferred dye composition according to the invention is a composition as defined above, for which the polyether polyurethane (a) is obtained by polycondensation of at least three compounds comprising, a polyethylene glycol at 150 or 180 moles d ethylene oxide, stearyl alcohol (C18) and methylene bis (4-cyclohexylisocyanate), and the polyether polyurethane (b) is obtained by polycondensation of at least three compounds comprising, a polyethylene glycol with 150 or 180 moles of ethylene oxide, decyl alcohol (C10) and methylene bis (4-cyclohexylisocyanate).
- ACULYN 46 which is a polycondensate comprising at least as elements, a polyethylene glycol with 150 or 180 moles of ethylene oxide, stearyl alcohol and methylene bis (4-cyclohexyl-isocyanate) (SMDI), at 15% by weight in a matrix of maltodextrin (4%) and water (81%).
- SMDI methylene bis (4-cyclohexyl-isocyanate)
- ACULYN 44 which is a polycondensate comprising at least as elements, a polyethyieneglycol containing 150 or 180 moles of oxide of ethylene, decyl alcohol and methylene bis (4-cyclohexylisocyanate) (SMDI), at 35% by weight in a mixture of propylene glycol (39%) and water (26%).
- compositions A and B consisting of a ready-to-use dye composition, consisting of a composition A comprising, in a medium suitable for dyeing, either at least one oxidation dye (base and / or coupler) , or at least one direct dye and of a composition B comprising at least one oxidizing agent, the polyurethane polyethers (a) and (b) defined above being together present in composition A and / or in composition B, or separately in each of compositions A or B.
- the invention also relates to a process for dyeing keratin fibers, and in particular human keratin fibers such as the hair, consisting in applying to the dry or wet keratin fibers, at least one composition containing, in a medium suitable for dyeing, at least one direct dye and at least one combination defined above of polyurethane polyethers (a) and (b), and that after having optionally allowed the composition to act on the fibers for an exposure time ranging from 3 to 60 minutes, the fibers are rinsed, optionally washed, rinsed again and then dried.
- the invention relates more particularly to a process for dyeing keratin fibers, and in particular human keratin fibers such as the hair, consisting in applying to the fibers at least one composition A containing, in a medium suitable for dyeing, ie at least an oxidation dye precursor and optionally at least one coupler, or at least one direct dye, the color being revealed at alkaline, neutral or acidic pH, using an oxidizing composition B which is mixed just at the time of use in composition A or which is applied sequentially without intermediate rinsing, the polyurethane polyethers (a) and (b) defined above, being present together in composition A and / or in composition B, or separately in each compositions A and B.
- the invention also relates to dyeing devices or “kits” with several compartments.
- a device with 2 compartments comprises a first compartment containing a composition A1 containing, in a medium suitable for dyeing, at least one direct dye, and another compartment containing a composition B1 containing, in a medium suitable for dyeing , at least one of the polyurethane polyethers (a) or (b) defined above, the other polyether polyether (s) being present in composition A1.
- Another 2-compartment device comprises a compartment containing a composition A2 containing, in a medium suitable for dyeing, either at least one oxidation dye precursor, and optionally one or more couplers, or at least one dye direct, and another compartment containing a composition B2 containing, in a medium suitable for dyeing, an oxidizing agent, the polyether polyurethanes (a) and (b) defined above being present together in composition A2 and / or the composition B2, or separately in each of compositions A2 and B2.
- Another device with 3 compartments according to the invention, comprises a first compartment containing a composition A3 containing, in a medium suitable for dyeing, either at least one oxidation dye precursor, and optionally one or more couplers, or at least one direct dye, a second compartment containing a composition B3 containing, in a medium suitable for dyeing, at least one agent oxidant, and a third compartment containing a composition C containing, in a medium suitable for dyeing, at least one polyether polyurethane (a) or (b) above defined, the other polyether (s) polyurethane (s) being present independently of one another in one or more of said three compartments.
- Another subject of the present invention is the use of a dye composition containing at least the combination of polyurethane polyethers (a) and (b) defined above to improve or restore the shine of keratin fibers, in particular human fibers and of preferably hair.
- polyurethane polyethers (a) and (b) according to the invention can be prepared according to the methods described in US Patents 4,079,028, 4,180,491, 4,155,892 and 5,281,654.
- the amount by weight of the polyurethane polyether (a) is preferably between approximately 0.01 and 5%, and even more preferably between 0.02 and 2%, and that of the polyether polyurethane (b) varies preferably between about 0.01 and 5%, and even more preferably between 0.02 and 2%, relative to the total weight of the composition.
- the weight ratio of the polyether polyurethane (a) to the polyether polyurethane (b) is between 0.1 and 10 and preferably between 0.5 and 5.
- the oxidation dyes which can be used according to the invention are chosen from oxidation bases and / or couplers.
- the compositions according to the invention contain at least one oxidation base.
- oxidation bases which can be used in the context of the present invention are chosen from those conventionally known in oxidation dyeing, and among which mention may especially be made of paraphenylenediamines, double bases, ortho- and para-aminophenols and heterocyclic bases following:
- R- ! represents a hydrogen atom, an alkyl radical C ⁇ -C 4 monohydroxyalkyl C ⁇ -C 4 polyhydroxyalkyl, C 2 -C 4 alkoxy (C ⁇ -C 4) alkyl (Cr C) alkyl, C ⁇ -C 4 substituted by a nitrogen, phenyl or 4'-aminophenyl group;
- R 2 represents a hydrogen atom, a C ⁇ -C 4 alkyl radical, C- ⁇ -C monohydroxyalkyl or C 2 -C 4 polyhydroxyalkyl, alkoxy (d- C 4 ) alkyl (CrC) or dC 4 alkyl substituted by a nitrogen group;
- R 3 represents a hydrogen atom, a halogen atom such as a chlorine atom, an alkyl radical in CC, sulfo, carboxy, monohydroxyalkyl in C ⁇ -C or hydroxyalkoxy in C ⁇ -C 4 , acetylaminoalkoxy in CC 4 , C ⁇ -C mesylaminoalkoxy or CC 4 carbamoylaminoalkoxy,
- l ⁇ represents a hydrogen atom, a halogen atom or a CC 4 alkyl radical.
- nitrogen groups of formula (I) above there may be mentioned in particular the amino, monoalkyl (C- ⁇ -C 4 ) amino, dialkyl (CrC 4 ) amino, trialkyl (C ⁇ -C 4 ) amino, monohydroxyalkyl radicals (CrC 4 ) amino, imidazolinium and ammonium.
- paraphenylenediamines of formula (I) above there may be mentioned more particularly paraphenylenediamine, paratoluylenediamine, 2-chloro-paraphenylenediamine, 2,3-dimethyl-paraphenylenediamine, 2,6-dimethyl-paraphenylenediamine, 2 , 6-diethyl-paraphenylenediamine, 2,5-dimethyl-paraphenylenediamine, N, N-dimethyl-paraphenylenediamine, N, N-diethyl-paraphenylenediamine, N, N-dipropyl-paraphenylenediamine, 4-amino-N, N-diethyl-3-methyl-aniline, N, N-bis- ( ⁇ -hydroxyethyl) - paraphenylenediamine, 4-amino-N, N-bis- ( ⁇ -hydroxyethyl) -3-methyl-aniline, 4 -amino-3-chloro-N,
- 2-hydroxymethyl-paraphenylenediamine la - N, N-dimethyl-3-methyl- paraphenylenediamine, N, N- (ethyl, ⁇ -hydroxyethyl) -paraphenylenediamine, N- ( ⁇ , ⁇ -dihydroxypropyl) paraphenylenediamine, N- (4'-aminophenyl) - paraphenylenediamine, N-phenyl-paraphenylenediamine, 2- ⁇ -hydroxyethyloxy-paraphenylenediamine, and their addition salts with an acid.
- paraphenylenediamines of formula (I) above very particularly preferred is paraphenylenediamine, paratoluylenediamine, 2-isopropyl-paraphenylenediamine, 2- ⁇ -hydroxyethyl-paraphenylenediamine, 2- ⁇ -hydroxyethyloxy-paraphenylenediamine, 6-dimethyl-paraphenylene diamine, 2,6-diethyl-paraphenylenediamine, 2,3-dimethyl- paraphenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) -paraphenylenediamine, 2-chloro-paraphenylenediamine, and their addition salts with an acid.
- double bases is intended to mean compounds comprising at least two aromatic rings on which are carried amino and / or hydroxyl groups.
- double bases which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may in particular be made of the compounds corresponding to the following formula (II), and their addition salts with an acid:
- - Zi and Z 2 identical or different, represent a hydroxyl radical or -NH 2 which can be substituted by an alkyl radical in CC 4 or by a link arm Y;
- the link arm Y represents an alkylene chain comprising from 1 to 14 carbon atoms, linear or branched which can be interrupted or terminated by one or more nitrogen groups and / or by one or more heteroatoms such as oxygen atoms, sulfur or nitrogen, and optionally substituted by one or more hydroxyl or C1-C6 alkoxy radicals;
- R 5 and R ⁇ represent a hydrogen or halogen atom, a C 1 -C 4 alkyl radical, C1-C4 monohydroxyalkyl, C -C 4 polyhydroxyalkyl, aminoalkyl in
- R 7 , R 8 , Rg, R10, R11 and R 12 identical or different, represent a hydrogen atom, a link arm Y or a C ⁇ -C 4 alkyl radical; it being understood that the compounds of formula (II) have only one linker arm Y per molecule.
- nitrogen groups of formula (II) above there may be mentioned in particular the amino, monoalkyl (CC 4 ) amino, dialkyl (C 1 -C 4 ) amino, trialkyl (CrC 4 ) amino, monohydroxyalkyl (C ⁇ -) radicals.
- N.N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) 1, 3-diamino propanol N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- ( 4-methylaminophenyl) tetramethylenediamine, N, N'-bis- (ethyl) N, N'-bis- (4'-amino, 3'-methylphenyl) ethylenediamine, 1, 8-bis- (2,5 -diaminophenoxy
- N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) 1, 3-diamino propanol, 1, 8-bis- (2,5-diaminophenoxy) - 3,5-dioxaoctane or one of their addition salts with an acid are particularly preferred.
- R 3 represents a hydrogen atom, a halogen atom such as fluorine, an alkyl radical C ⁇ -C 4 monohydroxyalkyl C ⁇ -C 4 alkoxy (C ⁇ -C 4) alkyl (CC 4) or aminoC CrC 4 , or hydroxyalkyl (CrC) aminoalkyl C ⁇ -C 4 .
- R14 represents a hydrogen atom or a halogen atom such as fluorine, an alkyl radical in C- ⁇ -C 4 monohydroxyalkyl -C 4 polyhydroxyalkyl, C 2 -C 4 aminoalkyl -C 4 cyanoalkyl CC 4 or alkoxy (C- ⁇ -C 4 ) alkyl (CC), it being understood that at least one of the radicals R 13 or R ⁇ 4 represents a hydrogen atom.
- a halogen atom such as fluorine, an alkyl radical in C- ⁇ -C 4 monohydroxyalkyl -C 4 polyhydroxyalkyl, C 2 -C 4 aminoalkyl -C 4 cyanoalkyl CC 4 or alkoxy (C- ⁇ -C 4 ) alkyl (CC), it being understood that at least one of the radicals R 13 or R ⁇ 4 represents a hydrogen atom.
- para-aminophenols of formula (III) above there may be mentioned more particularly para-aminophenol, 4-amino-3-methyl-phenol, 4-amino-3-fluoro-phenol, 4-amino -3-hydroxymethyl-phenol, 4-amino- 2-methyl-phenol, 4-amino-2-hydroxymethyl-phenol, 4-amino- 2-methoxymethyl-phenol, 4-amino-2-aminomethyl-phenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) -phenol, and their addition salts with an acid.
- ortho-aminophenols which can be used as oxidation bases in the context of the present invention, are in particular chosen from 2-amino-phenol, 2-amino-1-hydroxy-5-methyl- benzene, 2-amino-1-hydroxy-6-methyl-benzene, 5-acetamido-2-amino-phenol, and their addition salts with an acid.
- heterocyclic bases which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may more particularly be made of pyridine derivatives, pyrimidine derivatives, pyrazole derivatives, and their addition salts with an acid.
- pyridine derivatives mention may be made more particularly of the compounds described for example in patents GB 1,026,978 and GB 1,153,196, such as 2,5-diamino-pyridine, 2- (4-methoxyphenyl) amino-3- amino-pyridine, 2,3-diamino-6-methoxy-pyridine, 2- ( ⁇ -methoxyethyl) amino-3-amino-6-methoxy pyridine, 3,4-diamino-pyridine, and their salts addition with an acid.
- pyrimidine derivatives mention may be made more particularly of the compounds described for example in German patents DE 2,359,399 or Japanese patents JP 88-169 571 and JP 91-10659 or patent applications WO 96/15765, such as 2,4, 5,6-tetra-aminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2, 5,6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which mention may be made of pyrazolo- [1,5-a] -pyrimidine-3,7- diamine; 2,5-dimethyl-pyrazolo- [1,5-a] - pyhmidine-3,7-diamine; pyrazolo- [1,5-a] -pyhm
- the oxidation bases preferably represent from 0.0005 to 12% by weight approximately of the total weight of the composition of the composition (A).
- the couplers which can be used in the dyeing process according to the invention are those conventionally used in oxidation dyeing compositions, that is to say metaphenylenediamines, metaaminophenols and metadiphenols, mono- or poly-hydroxylated derivatives of naphthalene, sesamol and its derivatives and heterocyclic compounds such as, for example, indole couplers, indolinic couplers, pyridine couplers and their acid addition salts.
- couplers can in particular be chosen from 2-methyl-5-amino-phenol, 5-N- ( ⁇ -hydroxyethyl) -amino-2-methyl-phenol, 3-amino-phenol, 1, 3-dihydroxy - benzene, 1, 3-dihydroxy-2-methyl-benzene, 4-chloro-1, 3-dihydroxy-benzene, 2,4-diamino-1 - ( ⁇ -hydroxyethyloxy) -benzene, 2-amino -4- ( ⁇ -hydroxyethyiamino) -1 - methoxy-benzene, 1, 3-diamino-benzene, 1, 3-bis- (2,4-diaminophenoxy) - propane, sesamol, ⁇ -naphthol, 6-hydroxy-indole, 4-hydroxy-indole, 4-hydroxy-N-methyl-indole, 6-hydroxy-indoline, 2,6-dihydroxy-4-methyl-pyridine, 1-H- 3-methyl-pyrazole-5-one
- these couplers preferably represent from 0.0001 to 10% by weight approximately of the total weight of the composition (A), and even more preferably from 0.005 to 5% by weight approximately.
- addition salts with an acid of the oxidation bases and couplers are in particular chosen from hydrochlorides, hydrobromides, sulfates and tartrates, lactates and acetates.
- the direct dyes which can be used in the context of the present invention are those conventionally used in direct dyeing compositions or lightening direct dyeing, that is to say that they can in particular be chosen from benzene nitro, anthraquinone or azo dyes. , neutral, cationic, or anionic, naphthoquinonic dyes, triarylmethane dyes, xanthene dyes, Arianors and dyes described in patent applications WO 95/01772, WO 95/15144 and EP-A-0 714 954. They are used in concentrations of between 0.01 and 20% approximately by weight relative to the total weight of the composition.
- the medium of the composition suitable for dyeing is preferably an aqueous medium consisting of water. It can advantageously contain solvents cosmetically acceptable organic materials, including more particularly alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol, glycerin, or glycols or glycol ethers such as, for example , monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or its ethers such as, for example, propylene glycol monomethyl ether, butylene glycol, dipropylene glycol as well as diethylene glycol alkyl ethers such as, for example, monoethyl ether or monobethyl , in concentrations of between approximately 0.5 and 20% and preferably between approximately 2 and 10% by weight relative to the total weight of the composition.
- solvents cosmetically acceptable organic materials including more particularly alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and
- the composition may also contain an effective amount of other agents, which have previously been known in coloring, such as various usual adjuvants such as sequestrants such as ethylenediaminetotetracetic acid and etidronic acid, stabilizers, fatty substances, wetting agents , perfumes, consistency agents, cationic or amphoteric polymers, volatile or non-volatile, linear or cyclic, branched or unmodified, modified or unmodified silicones, preservatives, opacifiers such as fatty ethylene glycol esters, micas and micatitanes, ceramides or pseudoceramides, vitamins such as vitamin C, vitamin E, vitamin B5, vitamin A, provitamins such as panthenol, UVA or UVB filters, anionic surfactants, cationic, non-ionic, amphoteric or zwitterionic or their mixtures, mineral, vegetable or synthetic oils, sugars, etc.
- various usual adjuvants such as sequestrants such as ethylenediamineto
- surfactants suitable for implementing the present invention are in particular the following:
- anionic surfactants which can be used, alone or as mixtures, in the context of the present invention, there may be mentioned in particular (non-limiting list) the salts (in particular alkaline salts, in particular sodium salts, ammonium salts, salts amines, amino alcohol salts or magnesium salts) of the following compounds: alkyl sulfates, alkyl ether sulfates, alkylamidoethersulfates, alkylaryl polyethersulfates, monoglycerides sulfates; alkylsulfonates, alkylphosphates, alkylamidesulfonates, alkylarylsulfonates, ⁇ -olefin-sulfonates, paraffin-sulfonates; (C 6 -C 24 ) alkyl sulfosuccinates, (C 6 -C 24 ) alkyl ethersulfosuccinates, (C 6 -C 24 ) alkyl ethersul
- alkyl esters C 6 -C 24 carboxylic polyglycosides such as the alkylglucoside citrates, the alkyipolyglycoside tartrate and the alkyipolyglycoside sulfosuccinates.
- anionic surfactants which can still be used, mention may also be made of the salts of fatty acids such as the salts of oleic, hcinoleic, palmitic, stearic acids, coconut oil or hydrogenated coconut oil acids; acyl lactylates whose acyl radical contains 8 to 20 carbon atoms.
- alkyl D galactoside uronic acids and their salts the polyoxyalkylenated (C 6 -C 2 ) alkyl ether carboxylic acids, the polyoxyalkylenated (C 6 -C 24 ) aryl ether carboxylic acids, the alkyl (C 6 -C 24 ) polyoxyalkylenated carboxylic amido ether and their salts, in particular those comprising from 2 to 50 alkylene oxide groups, in particular ethylene, and their mixtures.
- Non-ionic surfactants are also well known compounds per se (see in particular in this regard "Handbook of Surfactants” by MR PORTER, Blackie & Son editions (Glasgow and London), 1991, pp 116-178) and their nature is not, in the context of the present invention, critical. Thus, they can in particular be chosen from (nonlimiting list) alcohols, alpha-diols, alkylphenols or polyethoxylated, polypropoxylated fatty acids, having a fatty chain comprising for example 8 to 18 carbon atoms, number of ethylene oxide or propylene oxide groups which can range in particular from 2 to 50.
- copolymers of ethylene and propylene oxide, condensates of ethylene oxide and of propylene on fatty alcohols polyethoxylated fatty amides preferably having from 2 to 30 moles of ethylene oxide, polyglycerolated fatty amides comprising on average 1 to 5 glycerol groups and in particular 1, 5 to 4; polyethoxylated fatty amines preferably having 2 to 30 moles of ethylene oxide; esters of oxyethylenated sorbitan fatty acids having from 2 to 30 moles of ethylene oxide; fatty acid esters of sucrose, polyethyieneglycol fatty acid esters, alkylpolyglycosides, N-alkyl glucamine derivatives, amine oxides such as alkyl (C-] Q - C14) oxides or N-acylaminopropylmorpholine oxides. It will be noted that the alkylpolyglycosides constitute nonionic sur
- Amphoteric or zwitterionic surfactants may in particular be (non-limiting list) derivatives of aliphatic secondary or tertiary amines, in which the aliphatic radical is a chain linear or branched having 8 to 18 carbon atoms and containing at least one water-soluble anionic group (for example carboxylate, sulfonate, sulfate, phosphate or phosphonate); mention may also be made of (C8-C20) alkyl betaines, sulfobetaines, (C8-C20) alkyl amidoalkyl (C-j-Ce) betaines or (C $ - C20) amidoalkyl (C ⁇ -CQ) alkyl sulfobetaines.
- aliphatic secondary or tertiary amines in which the aliphatic radical is a chain linear or branched having 8 to 18 carbon atoms and containing at least one water-soluble anionic group (for example
- B represents -CH 2 CH 2 OX '
- C represents - (CH 2 ) Z -Y'
- z 1 or 2
- X 'de notes the group -CH 2 CH -COOH or a hydrogen atom
- Y' denotes - COOH or the radical -CH 2 - CHOH - SO3H
- R 2 'de notes an alkyl radical of an acid Rg -COOH present in coconut oil or in hydrolysed linseed oil, an alkyl radical, in particular C7, Cg , C11 or C-13, a C-17 alkyl radical and its iso form, an unsaturated C17 radical.
- Disodium Cocoamphodipropionate Disodium Lauroamphodipropionate, Disodium
- Caprylamphodipropionate Disodium Capryloamphodipropionate, Lauroampho- dipropionic acid, Cocoamphodipropionic acid.
- cocoamphodiacetate sold under the trade name MIRANOL® C2M concentrated by the company RHODIA
- cationic surfactants that may be mentioned in particular (nonlimiting list): the salts of primary, secondary or tertiary fatty amines, optionally polyoxyalkylenated; quaternary ammonium salts such as chlorides or bromides of tetraalkylammonium, alkylamidoalkyltrialkylammonium, trialkylbenzylammonium, trialkylhydroxyalkylammonium or alkylpyridinium; imidazoline derivatives; or amine oxides of a cationic nature.
- the amounts of surfactants present in the composition according to the invention can vary from 0.01 to 40% and preferably from 0.5 to 30% of the total weight of the composition.
- cationic polymer designates any polymer containing cationic groups and / or groups which can be ionized into cationic groups.
- the cationic polymers which can be used in accordance with the present invention can be chosen from all those already known per se as improving the cosmetic properties of the hair, namely in particular those described in patent application EP-A-337 354 and in French patents FR- 2,270,846, 2,383,660, 2,598,611, 2,470,596 and 2,519,863.
- the preferred cationic polymers are chosen from those which contain units comprising primary, secondary, tertiary and / or quaternary amine groups which can either be part of the main polymer chain or be carried by a lateral substituent directly connected thereto.
- the cationic polymers used generally have a number average molecular mass of between 500 and 5.10 6 approximately, and preferably between 10 3 and 3.10 6 approximately.
- cationic polymers mention may more particularly be made of polymers of the polyamine, polyaminoamide and quaternary polyammonium type.
- R3 identical or different, denote a hydrogen atom or a CH3 radical
- A identical or different, represent an alkyl group, linear or branched, from 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms or a hydroxyalkyl group from 1 to 4 carbon atoms;
- R4, R5, R6 > identical or different, represent an alkyl group having from 1 to
- R-] and R 2 identical or different, represent hydrogen or an alkyl group having from 1 to 6 carbon atoms and preferably methyl or ethyl;
- X denotes an anion derived from a mineral or organic acid such as a methosulfate anion or a halide such as chloride or bromide.
- the polymers of family (1) may also contain one or more units deriving from comonomers which can be chosen from the family of acrylamides, methacrylamides, diacetones, acrylamides, acrylamides and methacrylamides substituted on nitrogen by lower alkyls (CJ-C4) , acrylic acids or methacrylics or their esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, vinyiic esters.
- comonomers which can be chosen from the family of acrylamides, methacrylamides, diacetones, acrylamides, acrylamides and methacrylamides substituted on nitrogen by lower alkyls (CJ-C4) , acrylic acids or methacrylics or their esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, vinyiic esters.
- Cationic cellulose derivatives such as cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, and described in particular in US Pat. No. 4,131,576, such as hydroxyalkyl celluloses, such as hydroxymethyl- , hydroxyethyl- or hydroxypropyl celluloses grafted in particular with a salt of methacryloylethyl trimethylammonium, of methacrylmidopropyl trimethylammonium, of dimethyl-diallylammonium.
- guar gums containing cationic trialkylammonium groups Guar gums modified with a salt (eg chloride) of 2,3-epoxypropyl trimethylammonium are used, for example.
- a salt eg chloride
- Such products are marketed in particular under the trade names of JAGUAR C13 S, JAGUAR C 15, JAGUAR C 17 or JAGUAR C162 by the company MEYHALL.
- Polyaminoamide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation by bifunctional agents Mention may be made, for example, of the adipic acid-diacoylaminohydroxyalkoyldialoylene triamine polymers in which the alkyl radical contains from 1 to 4 carbon atoms and preferably denotes methyl, ethyl, propyl. Such polymers are described in particular in French patent 1,583,363. Among these derivatives, there may be mentioned more particularly the adipic acid / dimethylaminohydroxypropyl / diethylene triamine polymers sold under the name "Cartaretine F, F4 or F8" by the company Sandoz.
- the molar ratio between the polyalkylene po.ylamine and the dicarboxylic acid being between 0.8: 1 and 1.4: 1; the resulting polyaminoamide being reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyaminoamide of between 0.5: 1 and 1.8: 1.
- Such polymers are described in particular in the patents American 3,227,615 and 2,961,347.
- Polymers of this type are in particular sold under the name "Hercosett 57” by the company Hercules Inc. or else under the name of "PD 170” or “Delsette 101” by the company Hercules in the case of the adipic acid copolymer / epoxypropyl / diethylenetriamine.
- 7 denotes a hydrogen atom or a methyl radical
- R 5 and R 16 independently of one another, denote an alkyl group having from 1 to 22 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably has 1 to 5 carbon atoms, a lower amidoalkyl group (CJ-C4), or R 15 and R 16 may denote, jointly with the nitrogen atom to which they are attached, heterocyclic groups, such as piperidinyl or morpholinyl
- Y " is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate, phosphate.
- R20 and R21 represent a linear or branched C ⁇ ⁇ -CQ alkyl radical substituted by a nitrile, ester, acyl, amide or -CO-O- R 22 -D or -CO-NH- R 2 -D group where R 22 is an alkylene and D a quaternary ammonium group;
- A1 and B1 represent polymethylenic groups containing from 2 to 20 carbon atoms which may be linear or branched, saturated or unsaturated, and which may contain, linked to or intercalated in the main chain, one or more aromatic rings, or one or more atoms of oxygen, sulfur or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and
- X " denotes an anion derived from a mineral or organic acid;
- 8 and 20 can form with the two nitrogen atoms to which they are attached a piperazine ring; in addition if A1 denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, B1 can also denote a group - (CH) n-CO-D-OC- (CH 2 ) n- in which D denotes: a) a glycol residue of formula: -OZO-, where Z denotes a linear or branched hydrocarbon radical or a group corresponding to one of the following formulas:
- x and y denote an integer from 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing an average degree of polymerization; b) a bis-secondary diamine residue such as a piperazine derivative; c) a bis-primary diamine residue of formula: -NH-Y-NH-, where Y denotes a linear or branched hydrocarbon radical, or else the bivalent radical
- X " is an anion such as chloride or bromide.
- These polymers have a number average molecular weight generally between 1000 and 100,000.
- Quaternary polyammonium polymers consisting of units of formula (VII): - - O - (CH 2 ) 2 (VII)
- D may be zero or may represent a group - (CH 2 ) r -CO- in which r denotes a number equal to 4 or 7, X- is an anion ;
- Such polymers can be prepared according to the methods described in U.S. Pat. Nos. 4,157,388, 4,702,906, 4,719,282. They are described in particular in patent application EP-A-122 324.
- Quaternary polymers of vinylpyrrolidone and of vinylimidazole such as for example the products marketed under the names Luviquat FC 905, FC 550 and FC 370 by the company B.A.S.F.
- -C4) trialkyl (C ⁇ - C4) ammonium salts such as the polymers obtained by homopolymerization of dimethylaminoethylmethacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethylmethacrylate quaternized by methyl chloride, homo or copolymerization being followed by crosslinking with an olefinically unsaturated compound, in particular methylene bis acrylamide.
- This dispersion is marketed under the name of "SALCARE® SC 92" by the company ALLIED COLLOIDS.
- These dispersions are marketed under the names of "SALCARE® SC 95" and "SALCARE® SC 96" by the company ALLIED COLLOIDS.
- cationic polymers which can be used in the context of the invention are polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and epichlorohydrin, quaternary polyureylenes and chitin derivatives.
- cationic polymers capable of being used in the context of the present invention, it is preferred to use the polymers of families (1), (9), (10) (11) and (14) and even more preferably the polymers of formulas (W) and (U) below:
- the concentration of cationic polymer in the compositions according to the present invention can vary from 0.01 to 10% by weight relative to the total weight of the composition, preferably from 0.05 to 5% and even more preferably from 0.1 to 3%.
- the composition can also contain antioxidants or reducing agents. These can be chosen in particular from sodium sulfite, thioglycolic acid, thiolactic acid, sodium bisulfite, ascorbic acid, dehydroascorbic acid, hydroquinone, 2-methyl-hydroquinone, ter.butyl-hydroquinone and homogentisic acid, and they are then generally present in amounts ranging from approximately 0.05 to 1.5% by weight relative to the total weight of the composition.
- antioxidants or reducing agents can be chosen in particular from sodium sulfite, thioglycolic acid, thiolactic acid, sodium bisulfite, ascorbic acid, dehydroascorbic acid, hydroquinone, 2-methyl-hydroquinone, ter.butyl-hydroquinone and homogentisic acid, and they are then generally present in amounts ranging from approximately 0.05 to 1.5% by weight relative to the total weight of the composition.
- composition (B) the oxidizing agent is preferably chosen from urea peroxide, bromates or ferricyanides of alkali metals, persalts such as perborates, persulfates and organic peroxides.
- the use of hydrogen peroxide is particularly preferred.
- Composition (B) advantageously consists of a solution of hydrogen peroxide, the titer of which can vary, more particularly, from approximately 1 to 40 volumes, and even more preferably from approximately 5 to 20.
- the pH of the ready-to-use composition applied to the keratin fibers is generally between the values 4 and 11. It is preferably between 6 and 10, and can be adjusted to the desired value by means of acidifying or basifying agents or buffers well known in the prior art in dyeing keratin fibers.
- basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and thethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of formula (VIII) below:
- R ⁇ ⁇ R 30 in which R is a propylene residue optionally substituted by a hydroxyl group or a CC 4 alkyl radical;
- R 27 , R 28 , R 2 g and R 30 identical or different, represent a hydrogen atom, a C 1 -C 4 alkyl or C1-C 4 hydroxyalkyl radical.
- the acidifying agents are conventionally, for example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as tartaric acid, citric acid, lactic acid, or acids sulfoniques.-
- An oxidation dye composition A1 was prepared containing ACULYN 46 [polyether polyurethane (a)] in an amount of 0.1% in active material (MA) and ACULYN 44 [polyether polyurethane (b)] at a rate of 0.1% in active material
- ACULYN 46 polyether polyurethane (a)] in an amount of 0.1% in active material (MA)
- ACULYN 44 polyether polyurethane (b)] at a rate of 0.1% in active material
- Two comparative compositions B1 and C1 were prepared in parallel which respectively contained only either the ACULYN 46 at the concentration of 0.2% MA or the ACULYN 44 at the concentration of 0 , 2% MA The exact compositions of these dyes are given below.
- compositions A1, B1 and C1 were mixed, at the time of use, in a plastic bowl and for 2 minutes to an oxidizing composition given below at the rate of 1 part of coloring composition per 1 5 part of oxidizing composition
- Each of the 3 oxidation dye mixtures obtained AB and C from compositions A1, B1 and C1 respectively was applied to locks of natural hair containing 90% white hairs and left to stand for 30 minutes. The locks were then rinsed with water, they were washed in standard shampoo again rinsed with water, then dried and untangled
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00969639A EP1233742A1 (fr) | 1999-11-18 | 2000-10-18 | Compositions de teinture contenant une association de deux polyethers polyurethanes |
AU79307/00A AU7930700A (en) | 1999-11-18 | 2000-10-18 | Dyeing composition containing a combination of two polyether polyurethanes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR99/14506 | 1999-11-18 | ||
FR9914506A FR2801205B1 (fr) | 1999-11-18 | 1999-11-18 | Compositions de teinture contenant une association de deux polyethers polyurethanes |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001035916A1 true WO2001035916A1 (fr) | 2001-05-25 |
Family
ID=9552258
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/002902 WO2001035916A1 (fr) | 1999-11-18 | 2000-10-18 | Compositions de teinture contenant une association de deux polyethers polyurethanes |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1233742A1 (fr) |
AU (1) | AU7930700A (fr) |
FR (1) | FR2801205B1 (fr) |
WO (1) | WO2001035916A1 (fr) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997024106A1 (fr) * | 1995-12-29 | 1997-07-10 | The Procter & Gamble Company | Compositions pour teintures capillaires |
WO1998027941A1 (fr) * | 1996-12-23 | 1998-07-02 | The Procter & Gamble Company | Compositions de coloration |
FR2769221A1 (fr) * | 1997-10-03 | 1999-04-09 | Oreal | Composition oxydante et utilisations pour la teinture, pour la deformation permanente ou pour la decoloration des fibres keratiniques |
WO1999036047A1 (fr) * | 1998-01-16 | 1999-07-22 | Bristol-Myers Squibb Company | Compositions de teinture capillaire a deux composantes, renfermant des polyether-polyurethanes et des agents conditionneurs |
EP0978522A1 (fr) * | 1998-08-06 | 2000-02-09 | National Starch and Chemical Investment Holding Corporation | Agents épaississants associatifs en milieu aqueux |
-
1999
- 1999-11-18 FR FR9914506A patent/FR2801205B1/fr not_active Expired - Fee Related
-
2000
- 2000-10-18 WO PCT/FR2000/002902 patent/WO2001035916A1/fr not_active Application Discontinuation
- 2000-10-18 AU AU79307/00A patent/AU7930700A/en not_active Abandoned
- 2000-10-18 EP EP00969639A patent/EP1233742A1/fr not_active Withdrawn
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997024106A1 (fr) * | 1995-12-29 | 1997-07-10 | The Procter & Gamble Company | Compositions pour teintures capillaires |
WO1998027941A1 (fr) * | 1996-12-23 | 1998-07-02 | The Procter & Gamble Company | Compositions de coloration |
FR2769221A1 (fr) * | 1997-10-03 | 1999-04-09 | Oreal | Composition oxydante et utilisations pour la teinture, pour la deformation permanente ou pour la decoloration des fibres keratiniques |
WO1999036047A1 (fr) * | 1998-01-16 | 1999-07-22 | Bristol-Myers Squibb Company | Compositions de teinture capillaire a deux composantes, renfermant des polyether-polyurethanes et des agents conditionneurs |
EP0978522A1 (fr) * | 1998-08-06 | 2000-02-09 | National Starch and Chemical Investment Holding Corporation | Agents épaississants associatifs en milieu aqueux |
Also Published As
Publication number | Publication date |
---|---|
FR2801205A1 (fr) | 2001-05-25 |
EP1233742A1 (fr) | 2002-08-28 |
AU7930700A (en) | 2001-05-30 |
FR2801205B1 (fr) | 2003-06-13 |
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