WO2002080871A1 - Hair colouring compositions comprising pyrazolone derivatives and their use - Google Patents
Hair colouring compositions comprising pyrazolone derivatives and their use Download PDFInfo
- Publication number
- WO2002080871A1 WO2002080871A1 PCT/US2002/010631 US0210631W WO02080871A1 WO 2002080871 A1 WO2002080871 A1 WO 2002080871A1 US 0210631 W US0210631 W US 0210631W WO 02080871 A1 WO02080871 A1 WO 02080871A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phenyl
- leaving group
- methyl
- hair
- active
- Prior art date
Links
Classifications
-
- 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
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
Definitions
- This invention relates to new compositions for colouring hair and to methods of using the compositions in hair colouring processes. In particular it relates to new combinations of developer and coupler components .
- compositions comprise various aromatic compounds, commonly known as developers (also known as precursors or primary intermediates) , together with various other compounds, commonly known as couplers. These are referred to as oxidative hair colouring agents because they require an oxidising agent for formation of colour.
- pyrazolones include 1-phenyl, 3 -methyl pyrazolone; 3- methyl pyrazolone; 1-phenyl pyrazolone; and 1,3-dimethyl pyrazolone.
- the composition comprises at least one developer selected from amino aromatic systems capable of being oxidised and thereafter undergoing only a single electrophilic attack (single electrophilic attack developers) .
- single electrophilic attack developers single electrophilic attack developers
- GB 1,025,916 also describes combinations of developers and couplers of this general type, but itself has disadvantages overcome by the international publications discussed above.
- compositions which contain the pyrazolone couplers It would be desirable to improve the UV fade resistance properties of compositions which contain the pyrazolone couplers .
- Various other publications have disclosed the use of pyrazolones in hair colouring compositions.
- FR 1426889 discloses 1-phenyl, 3-methyl pyrazolone in an example.
- EP-A-951,900 discloses various 1-phenyl pyrazolones.
- US 3,884,627 mentions 1,3-dimethyl pyrazolone in a long list of hair colouring components and does not exemplify its use.
- N-phenyl, 3-ethyl pyrazolone may be used in combination with para- phenylene diamine (PPD) .
- a hair colouring composition comprising one or more developers selected from amino aromatic systems capable of being oxidised and thereafter undergoing at least two electrophilic attack reactions, and one or more couplers selected from of the formula I :
- X is a non-leaving substituent
- Z is an active leaving group
- Y is an active leaving group or a non-leaving substituent, such that in the presence of an oxidising agent the or each developer reacts with the or each coupler substantially only at the position having the active leaving group Z and, if Y is an active leaving group
- Y provided that if X is phenyl then Y is not ethyl or methyl .
- the invention also provides a hair colouring kit comprising the defined developer and the defined coupler separately packaged.
- the invention also provides a method for colouring hair comprising applying to the hair the defined developer and the defined coupler.
- 1,025,916 significantly improves the UV fade resistance of the resulting colour. Consequently, the invention also provides the use of the defined developers to improve the UV fade resistance of compositions comprising the defined developers. It is unclear precisely why this benefit arises, but nevertheless it is a demonstrable benefit, as will be seen below.
- the developer is an amino aromatic compound which has a structure such that it is capable of being oxidised by an oxidising agent.
- the structure is also such that the oxidised developer is capable of undergoing electrophilic attack on at least two other molecules.
- Suitable developers of this type include aminoaromatic systems in which there are two primary amine groups .
- coupler is such that in the presence of an oxidising agent the majority couple with the developer at only one position.
- the coupler is of the same general type as disclosed in W098/52519, WO98/52520, W098/52521, W098/52522 and W098/52523 as magenta couplers.
- magenta couplers not specifically disclosed in those publications have particular advantages. These preferred materials are discussed in more detail below.
- the couplers produce a magenta colour on reacting with a developer molecule.
- the defined coupler may be the only coupler in the composition but preferably other types of coupler are also used to give a range of different colours.
- the coupler is of a specific formula which has an active leaving- group Z (and optionally Y) at a defined site.
- an “active leaving group” we mean any group which can be removed (under the conditions prevailing during the hair- dyeing process) so that the developer reacts at that position in the coupler molecule. A bond between the coupler and developer molecule is thus formed at the site of the active leaving group.
- active leaving groups are H, PhO, Cl, Br, alkoxy (RO) such as phenoxy PhO, and RS- in which R is alkyl or aryl, but any leaving group which leaves during the reaction so as to allow coupling between developer and coupler is suitable.
- Y is an active leaving group it may be any of those listed above for Z. Generally Y is a non-leaving substituent. Preferably also Z is H.
- X can be H, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, alkaryl, aralkyl, -R' NHCOR, -R'CONHR, -R'OH, -R'S0 2 R, -R'S0 2 NHR or -R'OR.
- R is H, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl or aralkyl
- R' is alkylene, cycloalkylene, alkenylene, cycloalkenylene, arylene, alkarylene or aralkylene (or substituted versions of any of these).
- Suitable substituting groups include OH, -OR, Cl, Br, F, -C0 2 H, -C0 2 R, -NH 2 , and -COR.
- X is preferably selected from methyl and phenyl.
- Y may be H, -OH, -C0 2 H, -C0 2 R, F, Cl, Br, -CN, -N0 2 , CF 3 , alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl, aralkyl, -NH 2 , -NHR, -NR 2 , -NHCOR, -R'NHCOR, CONHR, -R'CONHR, -R'OH, -S0 2 R, -S0 2 NHR, -R'S0 2 R, -R'S0 2 NHR, - S0 3 H, -OR, -R'OR or -COR.
- R is H, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl or aralkyl
- R' is alkylene, cycloalkylene, alkenylene, cycloalkenylene, arylene, alkarylene or aralkylene (or substituted versions of any of these) .
- Suitable substituting groups include OH, -OR, Cl, Br, F, -C0 2 H, -C0 2 R, -NH 2 , and -COR.
- Y is selected from phenyl and NHCOR in which R is alkyl and is preferably selected from phenyl and N- acetyl .
- R is alkyl and is preferably selected from phenyl and N- acetyl .
- X is methyl and Y is phenyl;
- X is phenyl and Y is NHCOR, preferably N-acetyl;
- X is methyl and Y is NHCOR, preferably N-acetyl;
- X is methyl or phenyl and Y is NHCOPhNH 2 ;
- X is phenyl and Y is phenyl.
- Y is not ethyl or methyl.
- X is phenyl then Y is not hydrogen.
- X is phenyl then Y is not ami o .
- Preferred compounds of the formula I are novel for use in hair colouring compositions.
- a hair colouring composition comprising one or more developers and one or more couplers selected from 1-methyl, 3-N-acetyl pyrazolone; 1-methyl, 3-phenyl pyrazolone; 1-phenyl, 3-N-acetyl pyrazolone; and 1-methyl, 3 -phenyl pyrazolone.
- the defined couplers can be used in amounts of from for instance 0.01 to 4%, preferably 0.01 to 2%, more preferably 0.03 to 3, eg 0.03 to 2%, and in some compositions not more than 1 or 0.5%.
- the developer is an amino aromatic system capable of being oxidised and thereafter undergoing at least two electrophilic attack reactions. It can for instance be selected from ortho or para-disubstituted benzene compounds, disubstituted pyridine compounds, disubstituted pyrimidines and diaminosubstituted pyrazoles . Preferably it is para- phenylene diamine .
- the composition contains no developers which are amino aromatic systems capable of being oxidised and thereafter undergoing only one electrophilic attack reaction (single electrophilic attack developers) .
- Developer is often included in the composition in amounts of from 0.01 to 7%, preferably 0.01 to 5% by weight based on total composition applied to the hair.
- Preferred amounts of developer are from 0.3 to 4%, eg 0.3 to 2%, preferably 0.4 to 3%, eg 0.4 to 1.5%.
- the solubility properties can be important.
- the developer and coupler compounds themselves should have solubility such that they can be formulated in appropriate concentrations. They preferably have solubility of at least 5 g/100 ml deionised water at pH about 10 and 25°C.
- the compositions of the invention may contain any other suitable oxidative dye materials, for instance other couplers of the general types disclosed in W098/52522 and the other PCT publications in this series referred to above, and other oxidative dye compounds .
- An optional component of the composition is an antioxidant. It may be selected from for instance sulphites such as sodium sulphite, hydroquinone, sodium bisulphite, sodium metabisulphite, thioglycolic acid, sodium dithionite, erythrobic acid and other mercaptans, ascorbic acid and n- propyl gallate.
- sulphites such as sodium sulphite, hydroquinone, sodium bisulphite, sodium metabisulphite, thioglycolic acid, sodium dithionite, erythrobic acid and other mercaptans, ascorbic acid and n- propyl gallate.
- antioxidant is included in an amount of at least 0.01 and usually not more than 3 or 4 wt.%, based on total weight of composition applied to the hair.
- antioxidant is included in an amount of at least 0.01 and usually not more than 3 or 4 wt.%, based on total weight of composition applied to the hair.
- This oxidising agent is normally included in the composition just before it is applied to the hair.
- the composition of the invention will be supplied in at least two individual packages such as bottles, the oxidising agent being included in one package and the developers and couplers being included in another.
- a preferred oxidising agent is hydrogen peroxide. This is often used in amounts up to 10 wt.%, based on composition applied to the hair.
- Other oxidising agents which may be used include other inorganic peroxygen oxidising agents, preformed organic peroxyacid oxidising agents and other organic peroxides such as urea peroxide, melamine peroxide, and mixtures of any of these.
- Suitable oxidising agents are preferably water-soluble, that is they have a solubility of at least about 5g in 1,000 ml of deionised water at 25°C ("Chemistry" C.E. Mortimer, 5th Edition, page 277) .
- the colouring compositions of the invention have pH above 7, in particular above pH 8 or 9.
- a pH of from 9 to 12 is often suitable.
- the systems of the invention can also be incorporated into low pH (eg pH 1 to 6) hair colouring systems.
- composition of the first aspect of the invention may be supplied to the consumer as a single package containing developer and coupler in a single unit such as a bottle.
- Couplers may be supplied as a preformed mixture selected to give a particular colour. Alternatively they can be supplied separately for mixing by the consumer to give a variety of different hair colours.
- the essential components are mixed to form the composition of the invention before application to the hair.
- oxidising agent is individually packaged separately from any of the colouring components. It is often mixed with these to form a component of the hair colouring composition before application to the hair. Alternatively it can be applied to the hair separately either before or after the hair colouring composition.
- the developers, couplers and oxidising agent, and any other materials to be applied to the hair as components of the composition of the invention may be provided in any suitable physical form.
- a preferred physical form is liquid.
- the liquid may be of low viscosity, for instance it may be water thin, or it may be of higher viscosity.
- the material may be suspended in a gel network.
- the gel may be solid or of low viscosity.
- the materials for colouring the hair are often formulated so that when they are mixed to form the composition of the invention for application to the hair they form a product of cream-like consistency, which is convenient for application to the hair.
- the final composition which is applied to the hair is often in the form of an emulsion.
- Each individual material may be supplied in a form such that the composition containing it has a pH of above or below 7. For instance it may be from pH 1 to 11.
- the carrier may have a pH of above 6.1 or 6.5 or even above 7, for instance from pH 8 or 9 to pH 10 or 11.
- a pH as supplied of from 1 to 6 can assist in improving stability of the components .
- the materials may be provided such that the pH of the final composition when mixed for application to the hair has a pH below 7 even though one of the components used to form it has a pH of above 7.
- Alcohols such as ethanol in amounts of from for instance 5 to 10 or 25% may be included to aid solubility of the developers and, particularly, the couplers in a water-based carrier.
- compositions may contain other optional ingredients.
- These can include other oxidative and non- oxidative colouring agents, buffering agents, hair swelling agents, catalysts for the oxidising agent, thickeners, diluents, enzymes, surfactants (especially anionic amphoteric, non-ionic or zwitterionic surfactants) , proteins and polypeptides and derivatives thereof; water-soluble or solubilizable preservatives; dye removers; H 2 0 2 stabilisers; moisturising agents; solvents; anti-bacterial agents; low temperature phase modifiers; viscosity control agents; hair conditioning agents; enzyme stabilisers; Ti0 2 and Ti0 2 - coated mica; perfumes and perfume solubilizers; chelating agents.
- Other optional materials include anti-dandruff actives such as ZPT. Details of suitable optional ingredients can be found in W098/52522. Examples
- "a” is a measure of the red and green quotients (colour hues) such that positive equates to red and negative to green
- "b” is a measure of the yellow and blue quotients (colour hues) such that positive equates to yellow and negative equates to blue.
- the machine is set to: mode - 0/45; port size - 1 inch; view size - 1 inch; light - D65; field of view - 10°; UV lamp/filter - none.
- the hair is placed in a sample holder designed to hold the hair in uniform orientation during measurement.
- Equivalent colorimeters can be used, but it must be ensured that the hair does not move during measurement .
- the hair must be spread to cover the 1 inch port during colour measurement.
- Dots are placed on the switch holder to guide the positioning of the holder at the port. The dots are lined up with a mark on the port and readings are taken at each spot .
- compositions according to the present invention can be used to colour hair of all colours, types and condition.
- various test hair switches can be tested herein. Two of these standard hair switches can be measured in terms of their approximate L, a, b values .
- a 4 gramme switch of about 8 inch long hair (or a 2 gramme switch of 4 inch long hair) is hung over a suitable container.
- the test colouring product is then prepared (ie, where applicable the separate bottle components are mixed together) and about 2 grammes of product per gramme hair is applied directly to the test hair switch.
- the colourant is massaged through the hair switch for up to about 1 minute and then left on the hair switch for up to about 30 minutes.
- the coloured hair switch is then cleansed (according to the shampoo protocol IV below) and dried. Drying can be effected either naturally (without heat assistance) or using a drier.
- the colour development (initial colour) of the coloured, cleansed, dried test hair switch can then be assessed using the Hunter Colourquest spectrophotometer .
- a 4 gramme, 8 inch test switch (or a 2 gramme, 4 inch test switch) of coloured hair is clamped over a suitable container and rinsed thoroughly for about 10 seconds using warm water (at about 100°F at about 1.5 gallons/minute pressure).
- Shampoo about 0.1 ml non-conditioning shampoo per gramme hair
- the shampoo and lathering process is then repeated with a final 60 second rinse. Excess water can be removed (squeezed) from the test switch using the fingers.
- the test switch is then dried either naturally, or using a pre-heated dryer box at about 140°F (for about 30 minutes) .
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2002578910A JP3742388B2 (en) | 2001-04-05 | 2002-04-04 | Hair coloring composition containing pyrazolone derivative and use thereof |
MXPA03008247A MXPA03008247A (en) | 2001-04-05 | 2002-04-04 | Hair colouring compositions comprising pyrazolone derivatives and their use. |
EP02725524A EP1372584A1 (en) | 2001-04-05 | 2002-04-04 | Hair colouring compositions comprising pyrazolone derivatives and their use |
US10/679,619 US20040107516A1 (en) | 2001-04-05 | 2003-10-06 | Hair colouring compositions and their use |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0108617A GB0108617D0 (en) | 2001-04-05 | 2001-04-05 | Hair colouring compositions and their use |
GB0108617.2 | 2001-04-05 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/679,619 Continuation US20040107516A1 (en) | 2001-04-05 | 2003-10-06 | Hair colouring compositions and their use |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002080871A1 true WO2002080871A1 (en) | 2002-10-17 |
Family
ID=9912347
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2002/010631 WO2002080871A1 (en) | 2001-04-05 | 2002-04-04 | Hair colouring compositions comprising pyrazolone derivatives and their use |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1372584A1 (en) |
JP (1) | JP3742388B2 (en) |
CN (1) | CN1258355C (en) |
GB (1) | GB0108617D0 (en) |
MX (1) | MXPA03008247A (en) |
WO (1) | WO2002080871A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5872265B2 (en) * | 2011-11-29 | 2016-03-01 | 花王株式会社 | Oxidative hair dye first agent |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1426889A (en) * | 1964-03-02 | 1966-02-04 | Oreal | New hair dye solution |
GB1213697A (en) * | 1967-04-29 | 1970-11-25 | Therachemie Chem Therapeut | Improvements in dyeing hair |
US4003699A (en) * | 1974-11-22 | 1977-01-18 | Henkel & Cie G.M.B.H. | Oxidation hair dyes based upon tetraaminopyrimidine developers |
US4043750A (en) * | 1975-04-12 | 1977-08-23 | Henkel & Cie Gmbh | Developer-coupler hair dyes based on triamino-pyrimidinones |
US4104020A (en) * | 1975-06-21 | 1978-08-01 | Henkel Kommanditgesellschaft Auf Aktien | Hair dye compositions containing 4,7-diaminoindazoles |
-
2001
- 2001-04-05 GB GB0108617A patent/GB0108617D0/en not_active Ceased
-
2002
- 2002-04-04 MX MXPA03008247A patent/MXPA03008247A/en unknown
- 2002-04-04 WO PCT/US2002/010631 patent/WO2002080871A1/en not_active Application Discontinuation
- 2002-04-04 EP EP02725524A patent/EP1372584A1/en not_active Withdrawn
- 2002-04-04 JP JP2002578910A patent/JP3742388B2/en not_active Expired - Fee Related
- 2002-04-04 CN CN 02807265 patent/CN1258355C/en not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1426889A (en) * | 1964-03-02 | 1966-02-04 | Oreal | New hair dye solution |
GB1079553A (en) * | 1964-03-02 | 1967-08-16 | Oreal | Compositions for dyeing keratinic fibres |
GB1213697A (en) * | 1967-04-29 | 1970-11-25 | Therachemie Chem Therapeut | Improvements in dyeing hair |
US4003699A (en) * | 1974-11-22 | 1977-01-18 | Henkel & Cie G.M.B.H. | Oxidation hair dyes based upon tetraaminopyrimidine developers |
US4043750A (en) * | 1975-04-12 | 1977-08-23 | Henkel & Cie Gmbh | Developer-coupler hair dyes based on triamino-pyrimidinones |
US4104020A (en) * | 1975-06-21 | 1978-08-01 | Henkel Kommanditgesellschaft Auf Aktien | Hair dye compositions containing 4,7-diaminoindazoles |
Also Published As
Publication number | Publication date |
---|---|
MXPA03008247A (en) | 2004-01-29 |
JP3742388B2 (en) | 2006-02-01 |
CN1258355C (en) | 2006-06-07 |
EP1372584A1 (en) | 2004-01-02 |
GB0108617D0 (en) | 2001-05-23 |
JP2004536793A (en) | 2004-12-09 |
CN1499953A (en) | 2004-05-26 |
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