EP1189576A2 - Composition capillaire comprenant un oxidase et de la cyclodextrine - Google Patents

Composition capillaire comprenant un oxidase et de la cyclodextrine

Info

Publication number
EP1189576A2
EP1189576A2 EP00940802A EP00940802A EP1189576A2 EP 1189576 A2 EP1189576 A2 EP 1189576A2 EP 00940802 A EP00940802 A EP 00940802A EP 00940802 A EP00940802 A EP 00940802A EP 1189576 A2 EP1189576 A2 EP 1189576A2
Authority
EP
European Patent Office
Prior art keywords
hair
amino
phenylenediamine
methyl
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00940802A
Other languages
German (de)
English (en)
Inventor
Joji Mitamura
Takeshi Onuki
Mutsumi Noguchi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lion Corp
Original Assignee
Lion Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lion Corp filed Critical Lion Corp
Publication of EP1189576A2 publication Critical patent/EP1189576A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/66—Enzymes
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/738—Cyclodextrins
    • 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 a hair composition in which a substance to be oxidized, an enzyme which utilizes oxygen as a substrate and does not produce hydrogen peroxide, and a cyclodextrin compound are compounded and, more particularly, it relates to a hair composition having a good stability with a lapse of time and being suitably able to be used as a reactive hairdye (a single preparation type) , a permanent-waving preparation of a single preparation type , a depilatory of a single preparation type, etc.
  • the present inventors have carried out an intensive study for achieving the above-mentioned object and, as a result, have found that , when a cyclodextrin compound is compounded with a hair composition wherein a substance to be oxidized and an oxidase which is an enzyme generating no hydrogen peroxide and utilizes oxygen as substrates are compounded, the said substance to be oxidized and the said oxidase are included in the said cyclodextrin compound whereby generation of insoluble aggregates, etc. as the time goes by is suppressed as shown in the examples mentioned later and stability with a lapse of time of the said hair composition is significantly improved.
  • the present invention has been accomplished consequently.
  • K is a hydrogen atom, NH 2 , OH or any of C 1 , 6 linear or branched alkyl group, alkenyl group and alkoxy group
  • L is OH or NH 2
  • K is located at 5-, 6- or 7-position in the ring and is located at ortho- position to L.
  • each of the above-mentioned substances to be oxidized may be used solely or two or more thereof may be used jointly.
  • a component used as a substance to be oxidized are thioglycolic acid, thioglycolate, cysteine, hydroxy ⁇ ysteine, dihydroxycysteine, acetylated cysteine and sodium sulfite. Each of them may be used solely or two or more thereof may be used jointly. Due to its object for use, the above-mentioned coloring substance is not compounded with those preparations .
  • a permanent-waving preparation it is appropriate to compound in an amount of 0.01-40% or, particularly, 0.1-20% to the total composition while, in the case of a depilatory, it is appropriate to compound in an amount of 0.01-50% or, particularly, 0.1-30% to the total composition.
  • the compounding amount of the substance to be oxidized is too small, it may be necessary to use a large amount of the composition for achieving the effect of the compounding sufficiently while, when the amount is too much, the compounding amount of oxidase naturally becomes small whereby the action by oxidation in use is hardly available and, moreover, stabilization may be sometimes difficult.
  • WO 99/36034, WO 99/36035, WO 99/36036, WO 99/36037, WO 99/36038, WO 99/36039, WO 99/36040, WO 99/36041, WO 99/36042, WO 99/36043, WO 99/36044, WO 99/36045 and WO 99/36046 in the name of L'Oreal discloses different kind of oxidizing dyes (developed substances or oxidation bases) and coupling components (coupling agents) which can also be used according to the present invention and which are hereby incorporated by reference.
  • para-phenylenediamines of the above formula ( 3 ) the following are especially preferred: para-phenylenediamine, paratoluylenediamine, 2-isopropyl para-phenylenediamine, 2- ⁇ -hydroxyethyl para-phenylenediamine, 2- ⁇ -hydroxyethyloxy para-phenylenediamine, 2,6-dimethyl para-phenylenediamine, 2,6-diethyl para-phenylenediamine, 2 , 3-dimethyl para- phenylenediamine, N,N-bis- ( ⁇ -hydroxyethyl) para- phenylenediamine, 2-chloro para-phenylenediamine, 2- ⁇ - acetylaminoethyloxy para-phenylenediamine and their addition salts with an acid.
  • compositions described for instance in the patents GB-PS 1026978 and GB-PS 1153196 can in particular be mentioned: 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 the addition salts thereof.
  • pyrazolo- [ 1, 5-a] - pyrimidines of the formula (6) shown below their addition salts with an acid or base and their tautomeric forms when a tautomeric equilibrium exists:
  • pyrazolo- [ 1 , 5-a] -pyrimidines of the above formula (6) the following can be mentioned in particular: pyrazolo- [ 1 , 5-a] -pyrimidine-3 , 7-diamine; 2,5-dimethyl pyrazolo- [ 1 , 5-a] -pyrimidine-3 , 7-diamine; pyrazolo- [ 1 , 5-a] -pyrimidine-3 , 5-diamine;
  • meta-aminophenol or meta-aminophenols applicable as coupling agents in the ready-to-use dye composition according to the invention is/are preferably selected from compounds of the following formula (7) and acid addition salts thereof:
  • R 26 and R 27 which are identical or differ, each represents a hydrogen atom, C 1 -C 4 alkyl or a halogen atom selected from chlorine, bromine and fluorine.
  • a halogen atom selected from chlorine, bromine and fluorine.
  • the meta-diphenols of the above formula (9) the following can in particular be mentioned: 1 , 3-dihydroxy-benzene, 2-methyl-l,3-dihydroxy-benzene, 4-chloro-l , 3-dihydroxy- benzene, 2-chloro-l , 3-dihydroxybenzene, and acid addition salts thereof .
  • Ri represents a hydrogen atom or C 1 -C 4 -alkyl
  • D represents a nitrogen atom or a group -CH
  • R 19 and R 20 which are identical or differ, each represents a hydrogen atom, a C 1 -C 4 alkyl group, which can be substituted with one of the groups -CN, -OH or -NH 2 or together with a carbon atom in the benzene ring form an optionally oxygen-containing or nitrogen-containing heterocyclic group, which can be substituted with one or more C 1 -C 4 alkyl groups; or a 4'- aminophenyl group,
  • R 32 represents a hydrogen atom or a C 1 -C 4 alkyl group, or R 32 together with a carbon atom in the benzene ring forms a heterocyclic group, which optionally includes an oxygen atom and/or is substituted with one or more C 1 -C 4 alkyl groups
  • R 33 represents a hydrogen atom or a halogen atom such as bromine, chlorine, iodine or fluorine,
  • X " represents an anion, preferably selected from chloride, methylsulphate and acetate,
  • the oxidase used in the present invention is that which uses oxygen as a substrate and does not generate hydrogen peroxide.
  • an oxidase of a four-electron reduced type has been known and its examples are catechol oxidase, amine oxidase and laccase. Each of them may be used solely or two or more thereof may be used jointly.
  • Particularly preferred enzymes are laccases and related enzymes, the term "laccases and related enzymes" including enzymes comprised by the enzyme classification E.C. 1.10.3.2
  • bilirubin oxidase enzymes comprised by the enzyme classification E.C. 1.3.3.5 and mono-phenol mono-oxygenase enzymes comprised by the enzyme classification E.C. 1.14.99.1.
  • the laccase may also be from a plant such as Rhus sp. , e.g. Rhus vernlclfera ,
  • Oxidases yielding peroxide are typically used in combination with a peroxidase to remove or at least reduce the peroxide produced.
  • Suitable oxidases include glucose oxidase (E.C. 1.1.3.4), hexose oxidase (E.C. 1.1.3.5), L-amino-acid oxidase (E.C. 1.4.3.2), xylitol oxidase, galactose oxidase (E.C. 1.1.3.9), pyranose oxidase (E.C. 1.1.3.10) and alcohol oxidase (E.C. 1.1.3.13).
  • the compounding amount of the cyclodextrin compound in the composition it is preferred to compound 0.1-75% or, particularly preferably, 0.5-60% to the total composition.
  • the compounding amount is too small, the effect by compounding of the cyclodextrin compound may not be well achieved while , when it is too much, there is a tendency that an increase in the effect proportional to an increase in the compounding amount is not resulted.
  • alcohol such as ethanol, propanol, n-butanol, sec-butanol and isopropanol
  • aromatic alcohol such as benzyl alcohol, phenoxyethanol and 2-benzyloxyethanol
  • polyhydric alcohol such as ethylene glycol, propylene glycol, butylene glycol and glycerol
  • aqueous ether such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl carbitol and ethyl carbitol
  • cyclic ketone such as propylene carbonate, N-methylpyrrolidone, N-ethylpyrrolidone and N- hexylpyrrolidone
  • formamide derivative such as N-cyclohexyl formamide and N,N-dibutyl formamide
  • acid such as glycolic acid and levulinic acid.
  • the original liquid was prepared by a conventional method according to the above formulation to prepare an original liquid for a permanent-waving preparation.
  • the original liquid was charged in an aerosol can and clinched In vacuo and 2.0 kg of LPG (a propellant) were charged so as to make the ratio of the original liquid to the gas 95:5 (by weight ) whereupon a permanent-waving preparation of an aerosol type of a single preparation type was prepared.
  • This permanent-waving preparation of a single preparation type was preserved at room temperature for six months, its appropriate amount was applied to 1.0 g of normal hair and the hair was wound on a curler, allowed to stand for 30 minutes, washed with water and shampooed.
  • Example 20 Depilatory of a Single Preparation Type (Foamy) Compounding Components Compounding Amount (wt%) (Original Liquid) Thioglycolic acid 5.0
  • the original liquid was prepared by a conventional method according to the above formulation to prepare an original liquid for a depilatory.
  • the original liquid was charged in an aerosol can and clinched In vacuo and 2.0 kg of LPG (a propellant) were charged so as to make the ratio of the original liquid to the gas 95:5 (by weight) whereupon a depilatory of an aerosol type of a single preparation type was prepared.
  • LPG a propellant
  • Toluene-2,5-diamine sulfate 1 m-Phenylenediamine hydrochloride 0.1 m-Aminophenol 0.8
  • ordinary containers such as aluminum can or tin-plated can with direct-jet nozzle or piston type nozzle may be used or a double container such as a bag-in type or an EXXEL type may be used as well.
  • the above hairdye was preserved at room temperature for six months , its appropriate amount was applied to 1.0 g of white hair and the hair was allowed to stand for 20 minutes, washed with water and shampooed.
  • the hair treated as such was dried using a drier whereupon the white hair was dyed in dark brown color and its shade was the same as that immediately after being prepared.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition capillaire qui se caractérise en ce qu'une substance à oxyder, une oxydase qui utilise l'oxygène en tant que substrat et ne génère pas de peroxyde d'hydrogène, et un composé de cyclodextrine sont combinés dans la même composition.
EP00940802A 1999-06-30 2000-06-22 Composition capillaire comprenant un oxidase et de la cyclodextrine Withdrawn EP1189576A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP18696199A JP4488125B2 (ja) 1999-06-30 1999-06-30 毛髪用組成物
JP18696199 1999-06-30
PCT/JP2000/004090 WO2001000144A2 (fr) 1999-06-30 2000-06-22 Composition capillaire

Publications (1)

Publication Number Publication Date
EP1189576A2 true EP1189576A2 (fr) 2002-03-27

Family

ID=16197764

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00940802A Withdrawn EP1189576A2 (fr) 1999-06-30 2000-06-22 Composition capillaire comprenant un oxidase et de la cyclodextrine

Country Status (4)

Country Link
EP (1) EP1189576A2 (fr)
JP (1) JP4488125B2 (fr)
AU (1) AU5567700A (fr)
WO (1) WO2001000144A2 (fr)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002255765A (ja) * 2001-03-05 2002-09-11 Kao Corp 染毛剤組成物
JP2003119115A (ja) * 2001-10-15 2003-04-23 Kao Corp 染毛剤組成物
JP2007518714A (ja) * 2003-12-24 2007-07-12 ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン カチオンクリーム基剤
EP1736207A1 (fr) * 2005-06-23 2006-12-27 Mibelle AG Cosmetics Composition dépilatoire
GB0520930D0 (en) * 2005-10-14 2005-11-23 Reckitt Benckiser Uk Ltd Composition and method of use
JP5363702B2 (ja) * 2006-06-07 2013-12-11 花王株式会社 一剤式染毛剤組成物
JP5252785B2 (ja) * 2006-06-07 2013-07-31 花王株式会社 エアゾール型一剤式染毛剤組成物
EP2030606B1 (fr) 2006-06-07 2017-03-29 Kao Corporation Composition de colorant capillaire en étui monopièce
JP5363703B2 (ja) * 2006-06-07 2013-12-11 花王株式会社 一剤式染毛剤組成物
JP2007326810A (ja) 2006-06-07 2007-12-20 Kao Corp 一剤式染毛剤組成物
JP5363700B2 (ja) * 2006-06-07 2013-12-11 花王株式会社 エアゾール型一剤式染毛剤組成物
JP5450945B2 (ja) * 2007-09-05 2014-03-26 ホーユー株式会社 酸化剤組成物
DE102010063518A1 (de) * 2010-12-20 2012-06-21 Henkel Ag & Co. Kgaa Verfahren und Zusammensetzungen zur Glättung keratinhaltiger Fasern
US8506651B2 (en) * 2011-12-30 2013-08-13 L'oreal S.A. Process for altering the appearance of hair using a composition containing dyes and non-hydroxide bases
JP7027042B2 (ja) * 2017-03-30 2022-03-01 株式会社コーセー 皮膚外用剤又は化粧料
JP7093291B2 (ja) * 2017-11-20 2022-06-29 花王株式会社 毛髪化粧料
EP3900790A4 (fr) * 2018-12-20 2022-11-16 Kao Corporation Composition
KR20220041099A (ko) 2019-08-05 2022-03-31 오노 야꾸힝 고교 가부시키가이샤 면역 체크포인트 저해약의 유효성 판정 바이오마커
WO2021208060A1 (fr) * 2020-04-17 2021-10-21 咏达生医材料股份有限公司 Dispositif d'alimentation en gaz, son utilisation pour éclaircir la couleur des cheveux et méthode
US20220354761A1 (en) * 2021-04-30 2022-11-10 L'oreal Compositions and methods for treating keratin fibers
FR3125414B1 (fr) * 2021-07-22 2025-12-26 Oreal Compositions et méthodes pour le traitement des fibres kératineuses
WO2024137598A1 (fr) * 2022-12-19 2024-06-27 L'oreal Compositions et procédés pour la décoloration des cheveux
FR3146401A1 (fr) * 2023-03-07 2024-09-13 L'oreal COMPOSITIONS ET PROCÉDÉS POUR éliminer la couleur des cheveux

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JPH0745385B2 (ja) * 1987-03-31 1995-05-17 協和醗酵工業株式会社 毛髪用化粧料組成物
FR2673534B1 (fr) * 1991-03-08 1995-03-03 Perma Composition pour la coloration enzymatique des fibres keratiniques, notamment des cheveux, et son application dans un procede de coloration.
US5432274A (en) * 1993-07-28 1995-07-11 National Research Council Of Canada Redox dye and method of preparation thereof using 2-hydroxypropyl-β-cyclodextrin and 1,1'-dimethylferrocene
WO1997019999A1 (fr) * 1995-11-30 1997-06-05 Novo Nordisk A/S Laccase avec des proprietes colorantes ameliorees
JP3796557B2 (ja) * 1997-06-11 2006-07-12 ライオン株式会社 染毛用組成物
JP3854736B2 (ja) * 1998-11-06 2006-12-06 ライオン株式会社 染毛剤組成物

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Also Published As

Publication number Publication date
WO2001000144A2 (fr) 2001-01-04
WO2001000144A3 (fr) 2001-07-05
AU5567700A (en) 2001-01-31
JP2001010938A (ja) 2001-01-16
JP4488125B2 (ja) 2010-06-23

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