EP1189576A2 - Hair composition comprising an oxidase and cyclodextrin - Google Patents
Hair composition comprising an oxidase and cyclodextrinInfo
- 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- Withdrawn
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)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18696199 | 1999-06-30 | ||
JP18696199A JP4488125B2 (ja) | 1999-06-30 | 1999-06-30 | 毛髪用組成物 |
PCT/JP2000/004090 WO2001000144A2 (en) | 1999-06-30 | 2000-06-22 | Hair composition comprising an oxidase and cyclodextrin |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1189576A2 true EP1189576A2 (en) | 2002-03-27 |
Family
ID=16197764
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00940802A Withdrawn EP1189576A2 (en) | 1999-06-30 | 2000-06-22 | Hair composition comprising an oxidase and cyclodextrin |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1189576A2 (ja) |
JP (1) | JP4488125B2 (ja) |
AU (1) | AU5567700A (ja) |
WO (1) | WO2001000144A2 (ja) |
Families Citing this family (22)
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 |
EP1715837B1 (de) * | 2003-12-24 | 2015-02-25 | Henkel AG & Co. KGaA | Kationische cremegrundlage |
EP1736207A1 (de) * | 2005-06-23 | 2006-12-27 | Mibelle AG Cosmetics | Zusammensetzung zur Depilierung |
GB0520930D0 (en) * | 2005-10-14 | 2005-11-23 | Reckitt Benckiser Uk Ltd | Composition and method of use |
JP2007326810A (ja) | 2006-06-07 | 2007-12-20 | Kao Corp | 一剤式染毛剤組成物 |
TWI386229B (zh) | 2006-06-07 | 2013-02-21 | Kao Corp | 一劑式染毛劑組成物 |
JP5363702B2 (ja) * | 2006-06-07 | 2013-12-11 | 花王株式会社 | 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 |
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 |
JP5363703B2 (ja) * | 2006-06-07 | 2013-12-11 | 花王株式会社 | 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 |
CN111372563A (zh) * | 2017-11-20 | 2020-07-03 | 花王株式会社 | 毛发化妆品 |
CN113195059B (zh) * | 2018-12-20 | 2024-03-15 | 花王株式会社 | 组合物 |
WO2021025031A1 (ja) | 2019-08-05 | 2021-02-11 | 小野薬品工業株式会社 | 免疫チェックポイント阻害薬の有効性判定バイオマーカー |
WO2021208060A1 (zh) * | 2020-04-17 | 2021-10-21 | 咏达生医材料股份有限公司 | 气体供应装置、用于淡化发色的用途及方法 |
US20220354761A1 (en) * | 2021-04-30 | 2022-11-10 | L'oreal | Compositions and methods for treating keratin fibers |
FR3125414A1 (fr) * | 2021-07-22 | 2023-01-27 | L'oreal | Compositions et méthodes pour le traitement des fibres kératineuses |
WO2024137598A1 (en) * | 2022-12-19 | 2024-06-27 | L'oreal | Compositions and methods for removing color from hair |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP0865465B1 (en) * | 1995-11-30 | 2001-05-30 | Novozymes A/S | Laccases with improved dyeing properties |
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 |
-
1999
- 1999-06-30 JP JP18696199A patent/JP4488125B2/ja not_active Expired - Fee Related
-
2000
- 2000-06-22 WO PCT/JP2000/004090 patent/WO2001000144A2/en not_active Application Discontinuation
- 2000-06-22 AU AU55677/00A patent/AU5567700A/en not_active Abandoned
- 2000-06-22 EP EP00940802A patent/EP1189576A2/en not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO0100144A3 * |
Also Published As
Publication number | Publication date |
---|---|
JP2001010938A (ja) | 2001-01-16 |
JP4488125B2 (ja) | 2010-06-23 |
AU5567700A (en) | 2001-01-31 |
WO2001000144A3 (en) | 2001-07-05 |
WO2001000144A2 (en) | 2001-01-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2001000144A2 (en) | Hair composition comprising an oxidase and cyclodextrin | |
KR0185009B1 (ko) | 케라틴 섬유의 산화 염색용 조성물 및 그를 이용한염색방법 | |
AU718420B2 (en) | Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres | |
AU9269698A (en) | Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres | |
HU224430B1 (hu) | Keratintartalmú rostok oxidációs festésére való készítmény és festési eljárás a készítmény alkalmazásával | |
JP4600635B2 (ja) | 角質繊維染色用組成物 | |
AU9269098A (en) | Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres | |
EP0969798B1 (fr) | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition | |
US20020007524A1 (en) | Method for dyeing dry hair | |
FR2773478A1 (fr) | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition | |
AU9269398A (en) | Oxidising composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres | |
US6572843B1 (en) | Method for treating hair | |
EP1137391B1 (en) | Method for treating hair | |
EP1129691A2 (fr) | Compositions de teinture des fibres kératiniques contenant des dérives d'indolizine et procédé de teinture | |
AU1974299A (en) | Composition for the oxidation dyeing of keratinous fibres containing a laccase and dyeing method using this composition | |
US6702863B1 (en) | Hairdye composition | |
FR2773477A1 (fr) | Composition tinctoriale et procedes de teinture des fibres keratiniques la mettant en oeuvre | |
EP1165027A1 (en) | Hairdye composition of single preparation type containing an oxidase | |
KR100553651B1 (ko) | 환원제로서 ν-아세틸시스테인을 사용하고 산화제로서락카아제를 사용하는 산화 염색 방법 | |
JP4471051B2 (ja) | 染毛剤組成物及びその製造方法 | |
FR2773471A1 (fr) | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition | |
AU718518B2 (en) | Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres | |
WO2000078273A2 (en) | Process for producing a hairdye composition | |
FR2773475A1 (fr) | Composition tinctoriale et procedes de teinture des fibres keratiniques la mettant en oeuvre | |
AU9353798A (en) | Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20011120 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE |
|
AX | Request for extension of the european patent |
Free format text: AL;LT;LV;MK;RO;SI |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
18W | Application withdrawn |
Withdrawal date: 20021126 |
|
RBV | Designated contracting states (corrected) |
Designated state(s): DE FR GB |