WO2003042199A1 - Mittel und verfahren zum färben von keratinfasern enthaltend 2-benzothiazolinon-hydrazon und chinon-derivate - Google Patents
Mittel und verfahren zum färben von keratinfasern enthaltend 2-benzothiazolinon-hydrazon und chinon-derivate Download PDFInfo
- Publication number
- WO2003042199A1 WO2003042199A1 PCT/EP2002/009381 EP0209381W WO03042199A1 WO 2003042199 A1 WO2003042199 A1 WO 2003042199A1 EP 0209381 W EP0209381 W EP 0209381W WO 03042199 A1 WO03042199 A1 WO 03042199A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- benzoquinone
- group
- methyl
- formula
- dione
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Definitions
- the present application relates to an agent for dyeing keratin fibers, such as silk, wool or hair and in particular human hair, which is a combination of (i) at least one 2-benzothiazolinone hydrazone derivative and (ii) at least one quinoid compound contains, as well as a method for dyeing keratin fibers using this agent.
- hair dyes are mainly divided into the area of the oxidation dyes or tints.
- Oxidation hair colors are ideal for covering higher levels of gray, here the oxidation coloring agents used with a gray content of up to 50% are usually referred to as oxidative tints, while those with a gray content of over 50% or for "lightening" are used in the Usually referred to as so-called oxidative colors.
- Direct dyes are mainly contained in non-oxidative coloring agents (so-called tinting agents). Some direct dyes, such as nitro dyes, can penetrate the hair due to their small size and dye them directly - at least in the outer areas.
- tints are very gentle on the hair and usually withstand 6 to 8 washes.
- Direct dyes are also often used in oxidative dyes to create certain shades or to intensify the color.
- coloring systems based on benzoquinones and compounds containing amino groups and / or hydroxyl groups have already been described in EP-OS 0 848942, DE-OS 43 35 624 and EP-PS 0 460 996.
- the present invention therefore relates to an agent for dyeing fibers (A), such as wool, silk, cotton or hair and in particular human hair, which is produced by mixing two components (A1) and (A2) before use and thereby characterized in that component (A1) contains at least one 2-benzothiazolinone hydrazone derivative of the formula (I) or its physiologically tolerable salt,
- R1 and R2 can be the same or different and are independently hydrogen, a halogen atom (F, CI, Br, J), a (C r C 4 ) alkyl group, one substituted with a halogen atom (F, CI, Br, J) (C ⁇ C ⁇ alkyl group, a (C 1 -C 4 ) alkoxy group, a sulfo group, a sulfamoyl group, a carboxy group, a nitro group, an acetamido group or an NR a R b group
- the radicals R a and R b may be the same or different and, independently of one another, represent hydrogen, a (C r C 6 ) alkyl group, a carbocyclic or heterocyclic, substituted or unsubstituted, aromatic compound, or R a and R b together with the nitrogen atom represent a saturated or unsaturated one , substituted or unsubstituted heterocyclic (C
- R3 is equal to a (C r C 4 ) alkyl group, a (CC 4 ) alkyl group substituted with a halogen atom (F, CI, Br, J), a sulfo (C r C 4 ) alkyl group, an acetyl group, a formyl group , a substituted or unsubstituted benzyl group, an isocyclic or heterocyclic compound; and component (A2) contains at least one ortho-quinone of the formula (II) or para-quinone of the formula (III),
- R4, R5, R6 and R7 independently of one another are hydrogen, chlorine, bromine, fluorine, a hydroxyl group, a straight-chain or branched (C, -C 6 ) -alkyl radical, a straight-chain or branched mono-hydroxy- (C 1 -C 6 ) alkyl radical, a straight-chain or branched polyhydroxy (C 2 -C 6 ) alkyl radical, a straight-chain or branched (CC 6 ) alkoxy radical, a straight-chain or branched mono- (C r C 6 ) -alkoxy- (C ⁇ C ⁇ alkyl radical, a straight-chain or branched poly- (C 1 -C 6 ) - alkoxy- (C 2 -C 6 ) alkyl radical, a (CC 2 ) -alkylenedioxy group, a sulfo group, a cyano group, a straight-chain or branched
- 2-benzothiazolinone hydrazone derivatives are preferred: 3-methyl-2-benzothiazolinone hydrazone hydrochloride, 3-ethyl-2-benzothiazolinone hydrazone hydrochloride, 3-phenyl 2-benzothiazolinone hydrazone hydrochloride and 3-benzyl-2-benzothiazolinone hydrazone hydrochloride, with the 3-methyl-2-benzothiazolinone hydrazone hydrochloride being particularly preferred.
- Preferred ortho-quinones of the formula (II) are: 4,5-dimethoxy-3,5-cyclohexadiene-1,2-dione, 5 (5H), 6 (6H) -dioxo-1,3-benzodioxole, 2,3 Dihydro-1,4-dimethyl-3-hydroxy-1 H-indole-5,6-dione, 2,3-dihydro-3-hydroxy-4-methoxy-1-methyl-1 H-indole-5,6 -dione, 3,5-di (1,1-dimethylethyl) -3,5-cyclohexadiene-1,2-dione, 2,3-dihydro-3-hydroxy-1-methyl-1 H-indole-5,6 -dione, 3,4,5,6-tetrachloro-3,5-cyclohexadiene-1,2-dione, 4,5-dimethoxy-3,6-diphenyl-3,5-cyclohexadiene-1,2-
- Preferred para-quinones of the formula (III) are: 1, 4-benzoquinone, 2-methyl-1, 4-benzoquinone, 2-tert-butyl-1, 4-benzoquinone, 2-phenyl-1, 4-benzoquinone, 2 , 5-Dimethyl-1, 4-benzoquinone, 2,6-dimethyl-1, 4-benzoquinone, 2-methyl-5- (1-methylethyl) -1, 4-benzoquinone, 2,5-di-tert-butyl -1,4-benzoquinone, 2,6-di-tert-butyl-1,4-benzoquinone, 2,5-diphenyl-1,4-benzoquinone, 2,3,5,6-tetramethyl-1,4-benzoquinone , 2-methoxy-1,4-benzoquinone, 2-methoxy-5-methyl-1,4-benzoquinone, 2,5-dimethoxy-1,4-benzoquinone, 2,6-dimethoxy-1,
- 1,4-benzoquinone 2-methyl-1,4-benzoquinone, 2,5-diphenyl-1,4-benzoquinone, 2,5-dihydroxy-1,4-benzoquinone, 2,3,5,6-tetrahydroxy- 1,4-benzoquinone, 2,5-di ((2-hydroxyethyl) amino) -1,4-benzoquinone,
- the compounds of the formula (I) and the ortho- or para-quinones of the formula (II) or (III) are generally stored separately from one another and are only mixed with one another shortly before use. However, if the compounds of the formula (I) and the ortho- or para-quinones of the formula (II) or (III) are in solid form, it is also possible to package them together and the ready-to-use colorant (A) shortly before use by mixing the compounds of the formula (I) and the ortho- or para-quinones of the formula (II) or (III) with water or a liquid preparation containing the other constituents of the composition.
- the colorant according to the invention can optionally additionally contain further customary, physiologically harmless, direct dyes from the group of cationic and anionic dyes, disperse dyes, azo dyes, quinone dyes and triphenylmethane dyes.
- These direct dyes can be used in component (A2) in a total amount of about 0.02 to 20 percent by weight, preferably 0.2 to 10 percent by weight, the total amount of direct dyes in that obtained by mixing components (A1) and ( A2) ready-to-use coloring agent (A) is about 0.01 to 10 percent by weight, preferably 0.1 to 5 percent by weight.
- the colorant according to the invention generally consists of a mixture of components (A1) and (A2), namely a colorant (A1) which contains the compound of the formula (I) and a further colorant (A2) which is the quinoid compound of the Contains formula (ll) / (lll).
- the compounds of the formula (I) and the ortho-quinones of the formula (II) and / or para-quinones of the formula (III) are each in a total amount in the respective color carrier composition (component (A1) or component (A2)) about 0.02 to 20 percent by weight, preferably about 0.2 to 10 percent by weight, wherein in the ready-to-use colorant (A) the compounds of the formula (I) and the ortho-quinone of the formula (II) and / or para-quinone of the formula (III) are each present in a total amount of about 0.01 to 10 percent by weight, preferably about 0.1 to 5 percent by weight.
- the preparation form for components (A1) and (A2) and the ready-to-use colorant (A) can be, for example, a solution, in particular an aqueous or aqueous-alcoholic solution, a cream, a gel or an emulsion.
- Their composition represents one Mixture of the compound of formula (I) or the ortho-quinones of the formula (II) and / or para-quinones of the formula (III) with the additives customary for such preparations.
- Customary additives used in colorants in solutions, creams, emulsions, gels or aerosol foams are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, n-propanol and isopropanol or glycols such as glycerol and 1,2-propanediol, furthermore wetting agents or Emulsifiers from the classes of anionic, cationic, amphoteric or nonionic surface-active substances, such as fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkyl sulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, oxethylated fatty alcohols, oxethylated nonylphenols, fatty ethyl fatty alcohols, fatty acids, fatty alcohol fatty acids, higher fatty alcohol fatty acids, fatty acid fatty alcohol starches
- the constituents mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight (in each case based on component (A1) or (A2)), the thickeners in one amount from about 0.1 to 25 percent by weight (in each case based on component (A1) or (A2)) and the care substances in a concentration of about 0.1 to 5.0 percent by weight (in each case based on component (A1) or (A2)).
- the pH of the ready-to-use colorant (A) and the colorant (A1) and (A2) is in each case about 3 to 12, preferably about 4 to 10, the pH of the ready-to-use colorant (A) generally being Mix component (A1) with component (A2).
- alkaline agents such as alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal acetates (especially sodium acetate) and alkaline earth metal acetates can be used to adjust the pH value of components (A1) and (A2) and the ready-to-use colorant (A), if required , Alkali carbonates or alkaline earth carbonates (especially sodium carbonate), or acids such as lactic acid, acetic acid, tartaric acid, phosphoric acid, hydrochloric acid, citric acid, ascorbic acid or boric acid.
- the ready-to-use colorant is prepared immediately before use by mixing components (A1) and (A2), optionally with the addition of an alkalizing agent or an acid, and then applied to the fiber, in particular human hair. Depending on the desired depth of color, this mixture is left to act for about 5 to 60 minutes, preferably about 15 to 30 minutes, at a temperature of about 20 to 50 ° C., in particular at about 30 to 40 ° C.
- the fiber is then rinsed with water, optionally washed with a shampoo and then dried.
- Another object of the present invention is a multi-component kit consisting of an agent of component (A1) and an agent of component (A2), and optionally an agent for adjusting the pH (alkalizing agent or acid).
- the means of components (A1) and (A2) can also consist of several Individual components exist which are only mixed with one another immediately before use.
- a two-component kit is also possible, the first component of which comprises the compounds of the formula (I) and the ortho-quinones of the formula (II) and / or para-quinones of the formula (III) and, if appropriate, further customary cosmetic powdery form Powder containing additives, and its second component is water or a liquid cosmetic preparation.
- a two-component kit consisting of an agent of component (A1) and an agent of component (A2) is particularly preferred.
- the colorant according to the invention enables a gentle, uniform and permanent coloring of the fibers, in particular keratin fibers, such as human hair, a wide range of colors from yellow to red or brown-black colors being possible.
- the ready-to-use coloring agent (A) is adjusted to the value given in Table 1 using sodium hydroxide solution, sodium carbonate, ammonia or citric acid.
- the ready-to-use hair dye is applied to the hair and evenly distributed with a brush. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with lukewarm water and then dried.
- the amount of ortho or para quinones used and the colorations obtained are summarized in Table 1 below.
- the L * a * b * color measurement values given in the present examples were determined using a color measuring device from Minolta, type Chromameter II.
- the L-value stands for the brightness (i.e. the lower the L-value, the greater the color intensity)
- the a-value is a measure of the red component (i.e. the larger the a-value, the greater the red component is larger).
- the b-value is a measure of the blue component of the color, the more negative the b-value, the greater the blue component.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02772186A EP1448540A1 (de) | 2001-11-14 | 2002-08-22 | Mittel und verfahren zum färben von keratinfasern enthaltend 2-benzothiazolinon-hydrazon und chinon-derivate |
JP2003544035A JP4046189B2 (ja) | 2001-11-14 | 2002-08-22 | ケラチン繊維を染色するための薬剤及び方法 |
US10/250,847 US7070625B2 (en) | 2001-11-14 | 2002-08-22 | Agent and method for coloring keratin fibers containing 2-benzothiazolinone-hydrazone and quinone derivatives |
BR0206394-8A BR0206394A (pt) | 2001-11-14 | 2002-08-22 | Agente e processo para tingimento de fibras de ceratina |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10155907A DE10155907A1 (de) | 2001-11-14 | 2001-11-14 | Mittel und Verfahren zur Färbung von Keratinfasern |
DE10155907.0 | 2001-11-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003042199A1 true WO2003042199A1 (de) | 2003-05-22 |
Family
ID=7705711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/009381 WO2003042199A1 (de) | 2001-11-14 | 2002-08-22 | Mittel und verfahren zum färben von keratinfasern enthaltend 2-benzothiazolinon-hydrazon und chinon-derivate |
Country Status (6)
Country | Link |
---|---|
US (1) | US7070625B2 (de) |
EP (1) | EP1448540A1 (de) |
JP (1) | JP4046189B2 (de) |
BR (1) | BR0206394A (de) |
DE (1) | DE10155907A1 (de) |
WO (1) | WO2003042199A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004078152A1 (de) * | 2003-03-05 | 2004-09-16 | Wella Aktiengesellschaft | Mittel und verfahren zum gleichzeitigen aufhellen und färben von keratinfasern |
WO2006094217A2 (en) * | 2005-03-03 | 2006-09-08 | The Procter & Gamble Company | Agent and method for colouring keratin fibres |
US7244278B2 (en) * | 2003-12-16 | 2007-07-17 | Wella Ag | Agent and method for oxidative coloring of keratin fibers |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10309523A1 (de) * | 2003-03-05 | 2004-09-16 | Wella Ag | Mittel und Verfahren zum Färben von Keratinfasern |
US20100010100A1 (en) * | 2008-07-09 | 2010-01-14 | Hinman Andrew W | Dermatological compositions with anti-aging and skin even-toning properties |
FR2983854B1 (fr) * | 2011-12-13 | 2014-01-10 | Oreal | Colorants directs quinoniques particuliers, composition tinctoriale comprenant au moins un tel colorant, procede de mise en oeuvre et utilisation |
US9359275B2 (en) | 2012-02-23 | 2016-06-07 | Children's Medical Center Corporation | Natural product antibiotics and analogs thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3869454A (en) * | 1971-06-04 | 1975-03-04 | Oreal | Novel diazamerocyanines and their use for dyeing keratinous fibers |
EP0460996A1 (de) * | 1990-05-29 | 1991-12-11 | L'oreal | Verfahren für die Keratin-Fasern-Färbung mit einem Aminoindol zusammen mit einem Chinonderivat |
EP0848942A1 (de) * | 1996-12-20 | 1998-06-24 | Wella Aktiengesellschaft | Mittel und Verfahren zum Färben von Keratinfasern |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE114415C (de) | ||||
DE1049381B (de) | 1959-01-29 | |||
JPS5119767A (en) | 1974-08-07 | 1976-02-17 | Nippon Kayaku Kk | 33 arukirubenzochiazoron 22 hidorazonjudotaino seiho |
DE4335624A1 (de) | 1993-10-19 | 1995-06-14 | Henkel Kgaa | Chinonhaltige Mittel zum Färben keratinhaltiger Fasern |
-
2001
- 2001-11-14 DE DE10155907A patent/DE10155907A1/de not_active Withdrawn
-
2002
- 2002-08-22 JP JP2003544035A patent/JP4046189B2/ja not_active Expired - Fee Related
- 2002-08-22 EP EP02772186A patent/EP1448540A1/de not_active Withdrawn
- 2002-08-22 BR BR0206394-8A patent/BR0206394A/pt not_active IP Right Cessation
- 2002-08-22 WO PCT/EP2002/009381 patent/WO2003042199A1/de not_active Application Discontinuation
- 2002-08-22 US US10/250,847 patent/US7070625B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3869454A (en) * | 1971-06-04 | 1975-03-04 | Oreal | Novel diazamerocyanines and their use for dyeing keratinous fibers |
EP0460996A1 (de) * | 1990-05-29 | 1991-12-11 | L'oreal | Verfahren für die Keratin-Fasern-Färbung mit einem Aminoindol zusammen mit einem Chinonderivat |
EP0848942A1 (de) * | 1996-12-20 | 1998-06-24 | Wella Aktiengesellschaft | Mittel und Verfahren zum Färben von Keratinfasern |
Non-Patent Citations (1)
Title |
---|
ESPIN J.C. ET AL: "Inhibition of Mushroom Polyphenol Oxidase by Agaritine", J. AGRIC. FOOD CHEM., vol. 46, no. 8, 1998, pages 2976 - 2980, XP002223784 * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004078152A1 (de) * | 2003-03-05 | 2004-09-16 | Wella Aktiengesellschaft | Mittel und verfahren zum gleichzeitigen aufhellen und färben von keratinfasern |
US7326254B2 (en) | 2003-03-05 | 2008-02-05 | Wella Ag | Means and method for the simultaneous bleaching and dyeing of keratin fibres |
US7244278B2 (en) * | 2003-12-16 | 2007-07-17 | Wella Ag | Agent and method for oxidative coloring of keratin fibers |
WO2006094217A2 (en) * | 2005-03-03 | 2006-09-08 | The Procter & Gamble Company | Agent and method for colouring keratin fibres |
EP1754514A1 (de) * | 2005-03-03 | 2007-02-21 | Wella Aktiengesellschaft | Mittel und Verfahren zum Färben von Keratinfasern |
WO2006094217A3 (en) * | 2005-03-03 | 2007-03-08 | Procter & Gamble | Agent and method for colouring keratin fibres |
JP2008531727A (ja) * | 2005-03-03 | 2008-08-14 | ザ プロクター アンド ギャンブル カンパニー | ケラチン繊維を着色するための薬剤及び方法 |
Also Published As
Publication number | Publication date |
---|---|
JP4046189B2 (ja) | 2008-02-13 |
EP1448540A1 (de) | 2004-08-25 |
US20040060124A1 (en) | 2004-04-01 |
DE10155907A1 (de) | 2003-05-15 |
JP2005509034A (ja) | 2005-04-07 |
BR0206394A (pt) | 2004-02-03 |
US7070625B2 (en) | 2006-07-04 |
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