EP1339693A1 - Diaminopyrazolderivate und ihre verwendung für die oxidative färbung von keratinfasern - Google Patents

Diaminopyrazolderivate und ihre verwendung für die oxidative färbung von keratinfasern

Info

Publication number
EP1339693A1
EP1339693A1 EP01999561A EP01999561A EP1339693A1 EP 1339693 A1 EP1339693 A1 EP 1339693A1 EP 01999561 A EP01999561 A EP 01999561A EP 01999561 A EP01999561 A EP 01999561A EP 1339693 A1 EP1339693 A1 EP 1339693A1
Authority
EP
European Patent Office
Prior art keywords
chosen
salts
alkyl
cooh
composition according
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Withdrawn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
EP01999561A
Other languages
English (en)
French (fr)
Inventor
Thilo Fessmann
Eric Terranova
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.)
LOreal SA
Original Assignee
LOreal SA
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 LOreal SA filed Critical LOreal SA
Publication of EP1339693A1 publication Critical patent/EP1339693A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to new diaminopyrazole derivatives, to a composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, comprising at least, as oxidation base, a derivative of diaminopyrazole and to the oxidation dyeing processes using it.
  • oxidation dye precursors in particular ortho- or paraphenylenediamines, ortho- or para-aminophenols, heterocyclic compounds such as derivatives diaminopyrazole, generally called oxidation bases.
  • oxidation bases are colorless or weakly colored compounds which, associated with oxidizing products, can give rise, through an oxidative condensation process, to colored and coloring compounds.
  • couplers or color modifiers the latter being chosen in particular from aromatic metadiamines, meta-aminophenols, metadiphenols and certain compounds. heterocyclic.
  • the dyes must also make it possible to cover white hair, and finally be the least selective possible, that is to say allow to obtain the smallest possible color differences throughout the same keratin fiber, which can be sensitized differently (that is to say damaged) between its tip and its root. They must also have good chemical stability in the formulations. They must have a good toxicological profile.
  • the subject of the present invention is therefore the new diaminopyrazoles having the following structure:
  • Ri denotes a C ⁇ -C 6 alkyl or C 2 -C 6 alkenyl radical, preferably up to C, linear or branched, carrying at least one substituent chosen from OR, NHR, NRR ', SR, SOR, S0 2 R, COOH, CONH 2 , CONRR ', PO (OH) 2 , SH, S0 3 X, a non-cationic heterocycle, Cl, Br or I,
  • X denotes H, Na, K or NH 4 ,
  • R and R ' identical or different, denote a C ⁇ -C 6 alkyl or C 2 -C 6 alkenyl radical, preferably up to C 4 , linear or branched, unsubstituted or substituted by one or more chosen functional groups among OH, NH 2 , OR,
  • R 2 denotes H, or a C ⁇ -C 6 alkyl or C 2 -C 6 alkenyl radical, preferably up to C 4 , linear or branched, unsubstituted or substituted by one or more functional groups chosen from OH, NH 2 , OR, NHR, NRR ', SR,
  • a subject of the invention is also the physiologically acceptable acid or base salts of the compounds of formula (I) such as the hydrochlorides, hydrobromides, sulfates, tartrates, lactates or acetates, or the salts obtained with the soda, potash, ammonia or amines or alkanolamines.
  • the subject of the invention is also a composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, characterized in that it contains, in a medium suitable for dyeing, at least as an oxidation base a diaminopyrazole of formula (I) above, or its physiologically acceptable acid or base salts.
  • the colors obtained with the oxidation dye composition in accordance with the invention are powerful, particularly bright and chromatic. They make it possible in particular to obtain shades free or containing very little blue or yellow. They also have excellent resistance properties vis-à-vis the action of various external agents (light, bad weather, washing, permanent waving, perspiration, friction).
  • the subject of the invention is also a process for the oxidation dyeing of keratin fibers using such a dye composition.
  • diaminopyrazoles of formula (I) As examples of diaminopyrazoles of formula (I) according to the invention, mention may be made of the compounds belonging to the following classes:
  • Ri is a linear C ⁇ -C 3 alkyl radical, substituted by a group S0 3 H, COOH, CONH 2 , methoxy, 2-hydroxyethyloxy, 2- hydroxyethylamino, mono- or dimethylamino, pyrrolidin-1-yle -3-ol, imidazolidin-1-yle, pintzrazin-1-yle, pioutheasternrazin-1-yl-ethanol, tetrahydrofuran-2-yle or tetra ydropyran-2-yle and R 2 denotes H, methyl, ethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-aminoethyl or carboxymethyl.
  • the diaminopyrazoles of formula (I) preferred according to the invention have the following structures:
  • the diaminopyrazoles of formula (I) more particularly preferred according to the invention are 4,5-diamino-l- (2'-methoxyethyl) - ⁇ yrazole and 4-amino- l- (2'-methoxyethyl) -5-methylamino pyrazole or their addition salts with physiologically acceptable acids.
  • the diaminopyrazoles of formula (I) according to the invention are prepared for example according to the following general method of preparation:
  • the precipitate thus formed is filtered and washed with demineralized water (100 ml).
  • the combined solids are brought to reflux in a Dean-Stark apparatus in the presence of toluene (200 ml).
  • the organic phase is filtered hot.
  • the solvent is evaporated to a residual volume of 110 ml.
  • the solution is cooled to 0-5 ° C for 1 h.
  • the precipitate formed is collected by filtration, washed with cold toluene (20 ml) and dried under vacuum at 80 ° C to give the tribromide (1) in the form of an off-white solid (30 g, 67%).
  • the dye composition according to the invention contains in particular from 0.001 to 10% by weight, preferably from 0.05 to 6% by weight, and even more preferably from 0.1 to 3% by weight, of at least one diaminopyrazole of formula (I) or its salts.
  • the dye composition in accordance with the invention can also contain, in addition to (or) diaminopyrazole (s) defined above, at least one additional oxidation base which can be chosen from the oxidation bases conventionally used in oxidation dyeing and among which there may be mentioned in particular paraphenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heretocyclic bases other than 4,5-diaminopyrazole used.
  • at least one additional oxidation base which can be chosen from the oxidation bases conventionally used in oxidation dyeing and among which there may be mentioned in particular paraphenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heretocyclic bases other than 4,5-diaminopyrazole used.
  • paraphenylenediamines mention may more particularly be made, for example, of paraphenylenediamine, paratoluylenediamine, 2,6-dimethyl paraphenylenediamine, 2- ⁇ -hydroxyethyl paraphenylenediamine, 2-n-propyl paraphenylenediamine, 2-isopropyline paraphenyl , N- ( ⁇ - hydroxypropyl) paraphenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 4-amino N- ( ⁇ -mehoxyethyl) aniline, the paraphenylenediamines described in French patent application FR 2630438, and their addition salts.
  • para-aminophenol there may be mentioned more particularly by way of example, para-aminophenol, 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxy-methyl 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.
  • ortho-aminophenols mention may more particularly be made, by way of example, of 2-amino phenol, 2-amino 5-methyl phenol, 2-amino-6-methylphenol, 5-acetamido 2-amino phenol, and their addition salts.
  • heterocyclic bases that may be mentioned more particularly by way of example, pyridine derivatives, pyrimidine derivatives, pyrazole derivatives other than the diamino pyrazoles of formula (I) used in accordance with the invention, and their addition salts.
  • these additional oxidation bases preferably represent from 0.0005 to 12%) by weight of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight of this weight.
  • the oxidation dye compositions in accordance with the invention may also contain at least one coupler and / or at least one direct dye, in particular for modifying the nuances or enriching them with reflections.
  • the couplers which can be used in the oxidation dye compositions in accordance with the invention can be chosen from the couplers conventionally used in oxidation dyeing and among which there may be mentioned in particular metaphenylenediamines, meta-aminophenols, metadiphenols, mono or polyhydroxy derivatives of naphthalene and heterocyclic couplers such as, for example, indole or pyridine derivatives and their addition salts.
  • couplers are more particularly chosen from 2-methyl 5-aminophenol, 5-N- ( ⁇ -hydroxyethyl) amino 2-methyl phenol, 6-chloro-2-methyl-5-aminophenol, 3-amino phenol, 1,3-dihydroxy benzene, 1,3-dihydroxy 2-methyl benzene, 4-chloro 1,3-dihydroxy benzene, 2,4-diamino l- ( ⁇ -hydroxyethyloxy) benzene, 2-amino 4 - ( ⁇ -hydroxyethylamino) 1- methoxybenzene, 1,3-diamino benzene, l, 3-bis- (2,4-diaminophenoxy) propane, 3-ureido aniline, 3-ureido 1-dimethylamino benzene, sesamol, l- ⁇ -hydroxyethylamino-3,4-methylenedioxybenzene, ⁇ -naphthol, 2 methyl-1 naphthol, 6-hydroxy in
  • these couplers represent in particular from 0.0001 to 10% of the total weight of the dye composition, preferably from 0.005 to 5% by weight, and even more preferably from 0.1 to 3% of this weight.
  • the addition salts with an acid which can be used in the context of the dye compositions of the invention are in particular chosen from hydrochlorides, hydrobromides, sulfates, tartrates, lactates and acetates.
  • the addition salts with a base are especially those obtained with soda, potash, ammonia, amines or alkanolamines.
  • the medium suitable for dyeing (or support) used according to the invention consists of water or of a mixture of water and at least one organic solvent chosen from lower C 1 -C 4 alkanols, polyols and polyol ethers, aromatic alcohols, analogues and their mixtures.
  • the dye composition according to the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic, cationic polymers , non-ionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, antioxidant agents, reducing agents, sun filters, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, silicones, film-forming agents, preserving agents, opacifying agents.
  • adjuvants conventionally used in compositions for dyeing the hair
  • anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof anionic, cationic polymers , non-ionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, antioxidant agents, reducing agents, sun filters, penetration agents, sequestering
  • the pH of the dye composition according to the invention is between 3 and 12.
  • the dye composition according to the invention can be in various forms, such as in the form of liquids, creams, gels, or under any other suitable form for dyeing keratin fibers, and in particular human hair.
  • the subject of the invention is also a process for dyeing keratin fibers and in particular human keratin fibers such as the hair using the dye composition as defined above.
  • At least one dye composition as defined above is applied to the fibers, for a time sufficient to develop the desired coloration, either in air or using an oxidizing agent.
  • the dye composition may optionally contain oxidation catalysts, in order to accelerate the oxidation process.
  • the coloring of the fibers can be carried out without the addition of an oxidizing agent, only in contact with the oxygen in the air.
  • At least one dye composition as defined above is applied to the fibers, the color being revealed at acidic, neutral or alkaline pH using an oxidizing agent which is added just at the time of use to the dye composition or which is present in an oxidizing composition applied simultaneously or sequentially separately.
  • the dye composition described above is preferably mixed with an oxidizing composition containing, in a medium suitable for dyeing, at the time of use, at least one oxidizing agent present in an amount sufficient to develop coloring.
  • the mixture obtained is then applied to the keratin fibers and left to stand for 3 to 50 minutes, preferably 5 to 30 minutes, after which it is rinsed, washed with shampoo, rinsed again and dried.
  • the oxidizing agent present in the oxidizing composition as defined above can be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratin fibers, and among which mention may be made of hydrogen peroxide, peroxide of urea, alkali metal bromates, persalts such as perborates and persulfates. Hydrogen peroxide is particularly preferred.
  • the pH of the oxidizing composition containing the oxidizing agent as defined above is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibers preferably varies between 3 and 12, and even more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers and as defined above.
  • the oxidizing composition as defined above may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
  • composition which is finally applied to the keratin fibers can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair. .
  • Another object of the invention is a device with several compartments or "kit” for dyeing or any other packaging system with several compartments, a first compartment of which contains the dye composition as defined above and a second compartment of which contains the oxidizing composition. as defined above.
  • These devices can be equipped with a means enabling the desired mixture to be delivered to the hair, such as the devices described in patent FR-2,586,913 in the name of the applicant.
  • each weight-for-weight dye composition is mixed with a solution of hydrogen peroxide at 20 volumes (6% by weight), the pH of which has been adjusted to approximately 2.5 with orthophosphoric acid.
  • the mixture is applied to gray hair with 90% white, natural or permanent, at a rate of 5 g for 0.5 g of hair, for 30 min.
  • the hair is then rinsed, washed with a standard shampoo and dried.
  • the color of the locks was evaluated in the L * a * b * system, on white and permanent hair, using a CM 2002 MINOLTA spectrophotometer.
  • clarity is indicated by the value L * on a scale from 0 to 100 while hue and saturation are expressed by a * and b *: a * and b * indicate two color axes, a * red-green axis and b * yellow-blue axis.
  • the 4,5-diaminopyrazoles according to the invention therefore make it possible to obtain intense and chromatic shades at alkaline pH.
  • Gray hair strands containing 90% natural and permanent whites are dyed with the dye compositions 5 and 6 above in the same way as for dyeing at alkaline pH.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP01999561A 2000-12-06 2001-11-29 Diaminopyrazolderivate und ihre verwendung für die oxidative färbung von keratinfasern Withdrawn EP1339693A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0015837A FR2817551B1 (fr) 2000-12-06 2000-12-06 Nouveaux derives de diaminopyrazole et leur utilisation en teinture d'oxydation des fibres keratiniques
FR0015837 2000-12-06
PCT/FR2001/003778 WO2002046165A1 (fr) 2000-12-06 2001-11-29 Derives de diaminopyrazole et leur utilisation en teinture d'oxydation des fibres keratiniques

Publications (1)

Publication Number Publication Date
EP1339693A1 true EP1339693A1 (de) 2003-09-03

Family

ID=8857314

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01999561A Withdrawn EP1339693A1 (de) 2000-12-06 2001-11-29 Diaminopyrazolderivate und ihre verwendung für die oxidative färbung von keratinfasern

Country Status (11)

Country Link
US (1) US7250063B2 (de)
EP (1) EP1339693A1 (de)
JP (1) JP2004515495A (de)
KR (1) KR20030070046A (de)
CN (1) CN1478079A (de)
AR (1) AR031774A1 (de)
AU (1) AU2002222074A1 (de)
BR (1) BR0116190A (de)
FR (1) FR2817551B1 (de)
MX (1) MXPA03005029A (de)
WO (1) WO2002046165A1 (de)

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FR2830190B1 (fr) * 2001-09-28 2004-10-01 Oreal Composition tinctoriale comprenant une base d'oxydation du type diaminopyrazole, une base d'oxydation heterocyclique et un coupleur
FR2835742B1 (fr) * 2002-02-12 2006-06-02 Oreal Composition tinctoriale comprenant une base d'oxydation du type diaminopyrazole, une base d'oxydation cationique et un coupleur
US7135046B2 (en) 2003-06-19 2006-11-14 L'oreal S.A. Dye composition comprising at least one oxidation base chosen from 4,5-diamino-1-(β-hydroxyethyl)-1H-pyrazole and 4,5-diamino-1-(β-methoxyethyl)-1H-pyrazole and the addition salts thereof and at least one coupler chosen from 6-hydroxyindole and the addition salts thereof
FR2856290B1 (fr) * 2003-06-19 2005-08-26 Oreal Composition tinctoriale comprenant le 4,5-diamino-1-(b-hydroxyethyl)-1h-pyrazole comme base d'oxydation et la 2,6-dihydroxy-3,4-dimethyl pyridine comme coupleur
FR2856293B1 (fr) * 2003-06-19 2005-08-26 Oreal Composition tinctoriale comprenant le 4,5-diamino-1-(b-hydroxyethyl)-1h-pyrazole comme base d'oxydation et le 2,6-bis-(b-hydroxyethyl)-amino toluene comme coupleur
FR2856292B1 (fr) * 2003-06-19 2005-08-26 Oreal Composition tinctoriale comprenant le 4,5-diamino-1-(b-hydroxyethyl)-1h-pyrazole ou le 4,5-diamino-1-(b-methoxyethyl)-1h-pyrazole a titre de base d'oxydation et la 2,6-diamino pyridine a titre de coupleur
FR2856291B1 (fr) * 2003-06-19 2005-08-26 Oreal Composition tinctoriale comprenant le 4,5-diamino-1-(b-hydroxyethyl)-1h-pyrazole ou le 4,5-diamino-1-(b-methoxyethyl)-1h-pyrazole a titre de base d'oxydation et le 6-hydroxy indole a titre de coupleur
US7150765B2 (en) 2003-07-11 2006-12-19 L'oreal S.A. Fatty acid-free liquid dye composition comprising at least one oxidation base and 2-methyl-1, 3-propanediol, dyeing process, and device
DE10354584A1 (de) * 2003-11-21 2005-06-30 Wella Ag Kationische Diaminopyrazole, ein Verfahren zu deren Herstellung und diese Verbindungen enthaltende Färbemittel
KR100667890B1 (ko) * 2006-07-10 2007-01-11 주식회사 건화 친환경적인 하천 굴곡부의 사면보호시설
CA2659998C (en) 2006-08-10 2013-10-01 Combe Incorporated A catalyzed air oxidation haircolor
WO2013105992A1 (en) 2011-02-22 2013-07-18 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a pyridine and derivatives thereof
CN103379894B (zh) 2011-02-22 2016-11-02 宝洁公司 包含1-己基/庚基-4,5-二氨基吡唑和1,3-苯二胺及其衍生物的氧化性染色组合物
EP2677992A1 (de) 2011-02-22 2014-01-01 The Procter and Gamble Company Haarfärbemittelzusammensetzungen mit einem 1-hexyl-/heptyl-4,5-diaminopyrazol und einem 2-aminophenol und derivaten davon
EP2677989A1 (de) 2011-02-22 2014-01-01 The Procter and Gamble Company Oxidative färbemittelzusammensetzungen mit einem 1-hexyl-/heptyl-4,5-diaminopyrazol und einem benzen-1,3-ol sowie derivaten davon
WO2013085553A2 (en) 2011-02-22 2013-06-13 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzo[1,3]dioxol-5-ylamine and derivatives thereof
MX336046B (es) 2011-02-22 2016-01-07 Procter & Gamble Composiciones para teñido oxidativo que comprenden un 1-hexil/heptil-4,5-diaminopirazol y un naftalen-1-ol y derivados de estos.
JP6436627B2 (ja) 2011-02-22 2018-12-12 ノクセル・コーポレーション １−ヘキシル−４，５−ジアミノピラゾール及びｍ−アミノフェノール及びその誘導体を含む酸化染色組成物
EP2628730B1 (de) 2012-02-16 2017-12-06 Noxell Corporation Mehrstufige eintopfsynthese von salzen des 5-amino-4-nitroso-1-alkyl-1h-pyrazols
EP2628731B1 (de) 2012-02-16 2014-04-23 The Procter and Gamble Company 1-Hexyl-1H-pyrazol-4,5-diamin-hemisulfat und seine Verwendung in Färbezusammensetzungen

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Also Published As

Publication number Publication date
US7250063B2 (en) 2007-07-31
JP2004515495A (ja) 2004-05-27
FR2817551B1 (fr) 2005-07-01
US20040083558A1 (en) 2004-05-06
FR2817551A1 (fr) 2002-06-07
WO2002046165A1 (fr) 2002-06-13
AU2002222074A1 (en) 2002-06-18
KR20030070046A (ko) 2003-08-27
AR031774A1 (es) 2003-10-01
MXPA03005029A (es) 2003-09-05
CN1478079A (zh) 2004-02-25
BR0116190A (pt) 2004-02-25

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