WO2001022931A1 - Composition cosmetique a base de composes organiques du silicium comportant au moins une fonction solubilisante non-basique - Google Patents

Composition cosmetique a base de composes organiques du silicium comportant au moins une fonction solubilisante non-basique Download PDF

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Publication number
WO2001022931A1
WO2001022931A1 PCT/FR1999/002290 FR9902290W WO0122931A1 WO 2001022931 A1 WO2001022931 A1 WO 2001022931A1 FR 9902290 W FR9902290 W FR 9902290W WO 0122931 A1 WO0122931 A1 WO 0122931A1
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WO
WIPO (PCT)
Prior art keywords
group
groups
halogen
hair
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.)
Ceased
Application number
PCT/FR1999/002290
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English (en)
French (fr)
Inventor
Henri Samain
Isabelle Rollat
Valérie JEANNE ROSE
Clément Sanchez
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
Priority to CA002385913A priority Critical patent/CA2385913A1/fr
Priority to DE69930971T priority patent/DE69930971T2/de
Priority to EP99946238A priority patent/EP1216022B1/fr
Priority to US10/089,193 priority patent/US6953584B1/en
Priority to ES99946238T priority patent/ES2260935T3/es
Priority to PCT/FR1999/002290 priority patent/WO2001022931A1/fr
Priority to JP2001526143A priority patent/JP2003510261A/ja
Priority to AU58679/99A priority patent/AU5867999A/en
Priority to BR9917504-5A priority patent/BR9917504A/pt
Publication of WO2001022931A1 publication Critical patent/WO2001022931A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585Organosilicon compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners

Definitions

  • the present invention relates generally to aqueous cosmetic compositions, in particular for the treatment of hair, comprising organic silicon compounds soluble in water, little or not at all polymerized.
  • organic compounds such as polymers to produce cosmetic compositions for the treatment of hair.
  • polymers used to dry solid materials are used to fix the hairstyle in a form. Such materials are also used to give shape retention effects.
  • Polymeric compounds, such as polysiloxanes are also used to give care effects to hair, particularly damaged or difficult to disentangle hair.
  • the cosmetic compositions containing these polymers are deposited on the hair which is left to dry or which is rinsed before going on to drying.
  • the use of polymeric compounds has several drawbacks.
  • the first drawback lies in the fact that, when the polymers are used in compositions above a certain concentration, the compositions obtained are difficult to apply due to the increase in the viscosity of the composition. This difficulty in applying the compositions leads to overloads in certain places of the hair and therefore to cosmetic defects and also implies that certain parts of the hair receive fewer compositions, which, in the end, induces a lesser effect on these parts.
  • the second drawback lies in the fact that these compositions are sometimes difficult to implement. Indeed, the polymeric compounds with low solubility in water, require the use of organic solvent or mixture of organic solvents. The use of organic solvent causes several problems, such as environmental problems and effects on the cosmeticity of the hair.
  • US Patent No. 4,347,763 describes cosmetic compositions comprising an organosiloxane monomer such as an aminoalkylalkoxysilane and an organic titanate in solution in an alcohol.
  • this patent describes a process for shaping the hair which consists in moistening it with water then in applying a solution containing in isopropanol from 0.5 to 15% by weight of an aminoalkylalkoxysilane and 0.005 to 1.5% by weight of an organic titanate and then to put the hair in the desired shape.
  • the solvent of the composition is an aliphatic hydrocarbon or an aliphatic halohydrocarbon, preferably 1, 1, 1 -trichloroethane.
  • the present invention therefore relates to aqueous, stable cosmetic compositions, in particular cosmetic compositions for the treatment and care of the hair, which remedy the drawbacks of the prior art.
  • the present invention relates to aqueous, stable cosmetic compositions for the treatment and care of the hair, giving the hair a long-lasting styling effect and a pleasant touch.
  • compositions which do not require the use of organic solvent and which have an effective cosmetic effect, resistant to rinsing, without the risk of hair problems loaded in the event of superposition, using in these compositions organic silicon compounds little or not polymerized, soluble in water, comprising at least one non-basic solubilizing chemical function. It has been observed that the application of such compositions makes it possible to obtain marked cosmetic effects, without problem in the event of overlapping, the effects of which resist well to rinsing and washing.
  • the cosmetic compositions in particular for the treatment of hair, comprise, in a cosmetically acceptable aqueous medium, at least 0.02% by weight relative to the weight total of the composition, of one or more organic compounds of silicon soluble in water, little or not polymerized, chosen from organosilanes comprising one atom of silicon and organosiloxanes comprising two or three atoms of silicon, organic compounds of silicon further comprising at least one non-basic solubilizing chemical function and at least two hydrolyzable groups per molecule.
  • the organic silicon compounds according to the invention are capable of forming, in an aqueous medium, a non-hybrid compound, after condensation on themselves and evaporation of the support.
  • non-hybrid compound means a compound which is chemically homogeneous as regards silicon, that is to say that it does not contain other additional metallic or organometallic species.
  • the organic silicon compounds are chosen from water-soluble organosilanes, comprising one silicon atom and water-soluble organosiloxanes, comprising two or three atoms. silicon, preferably two. They must also include at least one non-basic solubilizing chemical function, and preferably only one function.
  • the non-basic chemical solubilizing function can be any non-basic and in particular non-amino function which facilitates the solubilization of the organic silicon compound in water.
  • non-basic solubilizing functions mention may be made of carboxylic acids and their salts, quaternary ammoniums, sulfonic acids and their salts and poly (alkyl ether) residues such as poly (oxyalkylene) residues, for example poly (oxide of ethylene) and poly (propylene oxide) and polyglycols, polyacrylamides and acrylamides, and polyols (including natural polyols).
  • alkyl ether residues such as poly (oxyalkylene) residues, for example poly (oxide of ethylene) and poly (propylene oxide) and polyglycols, polyacrylamides and acrylamides, and polyols (including natural polyols).
  • the organic silicon compounds useful in the compositions of the present invention additionally comprise at least two hydrolyzable or hydroxyl groups per silicon atom.
  • the hydrolyzable groups are preferably alkoxy, aryloxy or halogen groups. They can also, optionally, include other chemical functions such as acid or amino functions.
  • this group can also include a chemical function such as an acid or amino function.
  • the preferred organosilanes according to the invention correspond to the formula:
  • R ' represents a halogen, an OR group,, R 0 ;
  • R'" represents a halogen, an OR 3 group, " Q ; at least two of the groups R ', R" and R'"being different from the groups R Q , R ' 0 and R “ 0 ;
  • R is a hydrocarbon group, saturated or unsaturated, linear or branched, comprising a non-basic, in particular non-amino, solubilizing chemical function; Ri, R 2 . R3.
  • RO 'R'o and ⁇ - "o ⁇ have, independently of each other, a saturated or unsaturated, linear or branched hydrocarbon group, optionally carrying additional non-basic solubilizing chemical groups, R,, R 2 and R 3 which may in addition denote hydrogen.
  • R,, R 2 , R 3 , R 0 , R'o and R "o represent an alkyl group from C j to C 12 , an aryl group from C 6 to C 14 , a group alkyl C, AC 8 - aryl from C 6 to C 14 and aryl from C 6 to C 14 alkyl C j to C g.
  • organosiloxanes preferred in the compositions of the present invention can be represented by the formula: R - s Si / R '
  • R represents a halogen or an OR 2 group
  • R, R 2 , R 'and R "' are defined as above, R""represents a halogen, an OR 4 group or a R" O group;
  • R 5 represents a halogen, an OR 6 group or an R "" 0> group
  • R 4 , R 6 , R '"o and R"" 0 represent a hydrocarbon group, saturated or unsaturated, linear or branched, optionally carrying additional non-basic solubilizing chemical groups, R 4 and R 6 can also denote hydrogen at least one of the groups R '", R""and R 5 being different from R" 0 , R'" 0 and R"" 0 .
  • R 4 , R 6 , R Q , R " 0 > R '" o and ⁇ ' o represent an alkyl group of C l to C, 2 , an aryl group of C 6 to C j 4 , an alkyl group of
  • R 5 preferably represents an alkyl group of C j to C 12 , an alkoxy group of C, to C 12 , an aryl group of C 6 to C 14 , an alkyl group of C, to C 8 -aryl of C 6 to C 14 , and an aryl group of C 6 to C 14 -alkyl of C, to C g .
  • the halogen is chlorine.
  • the R groups are preferably chosen from carboxylic acids and their salts, quaternary ammoniums, sulfonic acids and their salts, and polyalkyl ethers.
  • carboxylic acid functions and their salts mention may be made of the radicals of saturated monoacids such as acetic, propionic, butyric, isobutyric, valeric, isovaleric acids, saturated diacids such as oxalic, malonic, succinic, glutaric and adipic acids, unsaturated monoacids such as acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid and citraconic acid, carbocyclic acids such as benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, hydroxy and alkoxy carboxylic acids such as glycolic acid, lactic acid, tartaric acid and salicylic acid and the salts of these acids, in particular the alkaline salts and more particularly the sodium and potassium salts of these acids.
  • saturated monoacids such as acetic, propionic, butyric, isobutyric, valeric, isovaleric acids
  • saturated diacids such as
  • quaternary ammonium functions mention may be made of tetraalkylammonium, quaternary alkylarylammonium, alkyl and or aryl groups which may optionally include functions such as acid, hydroxyl, amino and halogen functions, and cyclic and heterocyclic quaternary ammonium.
  • alkylsulfonic acids such as methylsulfonic acid
  • arylsulfonic acids such as phenylsulfonic acid
  • alkoxysulfonic acids such as ethoxysulfonic acid, alkylaryl and arylalkylsulfonic acids
  • salts of these acids in particular the alkaline salts of these acids and more particularly the sodium and potassium salts of these acids.
  • alkyl ether residues mention may be made of poly (oxyethylene), poly (oxypropylene), poly (oxytetramethylene) and polyglycols such as poly (ethylene glycol) and poly (propylene glycol).
  • compositions according to the invention contain significant amounts of organic silicon compounds that are little or not polymerized, that is to say containing one, two or three silicon atoms.
  • the level of organic compounds of silicon little or not polymerized, according to the invention, is determined by usual methods of analysis such as NMR spectroscopy of silicon 29 and of the proton, and by chromatography.
  • compositions according to the invention are aqueous compositions.
  • adjuvants for example, to add a co-solvent such as an alcohol or a ketone, for example ethyl alcohol or acetone.
  • compositions of the invention may contain the adjuvants customary in the cosmetic field, such as oils, waxes or other usual fatty substances; conventional gelling agents and / or thickeners; emulsifiers; moisturizers; emollients, sun filters; hydrophilic or lipophilic active agents such as ceramides; free anti-radical agents; surfactants; polymers; proteins; bactericides; sequestrants; anti-dandruff; anti-oxidants; preservatives; perfumes; charges; coloring matters.
  • the quantities of these various adjuvants are those conventionally used in the field under consideration.
  • compositions according to the invention can be used in rinse-out or leave-in mode.
  • compositions according to the invention can be in any form suitable for topical application, in particular in the form of solutions of the lotion or serum type; in the form of aqueous gels; in the form of emulsions obtained by dispersion of a fatty phase in an aqueous phase (O / W) or vice versa (W / O), of more or less thick liquid consistency such as milks and more or less creamy creams.
  • compositions are prepared according to the usual methods.
  • compositions according to the invention are preferably used as hair products, in particular for maintaining the hairstyle or shaping the hair. They can also provide temporary coloring to the hair, well ensuring protection of the hair against the effects of UV radiation, while providing hold or fixing properties of the hair.
  • the hair compositions according to the invention are preferably styling products such as gels, styling lotions, brushing lotions, fixing and styling such as hairspray or spray.
  • Lotions can be packaged in various forms, in particular in vaporizers, pump-dispensers or in aerosol containers in order to ensure application of the composition in vaporized form or in the form of foam.
  • Such forms of packaging are indicated, for example when it is desired to obtain a spray, a foam for fixing or treating the hair.
  • the present invention also relates to the use of the composition according to the invention in a method of treating the hair, with a view to maintaining and / or coloring it.
  • the composition is applied to the hair which has been rinsed or not, preferably in the form of a spray, either using a pump bottle or using an aerosol. .
  • the hair can be put in the desired shape, either before application, or immediately after.
  • the drying time can be variable and depends on the nature of the composition.
  • the hair, after combing, has a very pleasant quality of touch.
  • composition Composed of silicon Water little or not polymerized, soluble in water
  • Composition 1 is introduced into a container which is provided with a spray system of the pump bottle type. We prepare two wigs of 15 g of natural hair. The hair is held at the roots on a rubber band and left free over the rest of the length.
  • the composition is sprayed on the first wig (2 g). This wig is left so until drying. The other wig, used for comparison, is also left to rest.
  • the hair is then washed with a sodium lauryl ether sulfate shampoo, then dried.
  • the cosmetic properties are noted a second time. Wig Styling effect before washing Styling effect after washing

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
PCT/FR1999/002290 1999-09-27 1999-09-27 Composition cosmetique a base de composes organiques du silicium comportant au moins une fonction solubilisante non-basique Ceased WO2001022931A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CA002385913A CA2385913A1 (fr) 1999-09-27 1999-09-27 Composition cosmetique a base de composes organiques du silicium comportant au moins une fonction solubilisante non-basique
DE69930971T DE69930971T2 (de) 1999-09-27 1999-09-27 Kosmetische zusammensetzung auf basis von silicium-organischen verbindungen, die mindestens eine nicht basische solubilisierende funktion aufweisen
EP99946238A EP1216022B1 (fr) 1999-09-27 1999-09-27 Composition cosmetique a base de composes organiques du silicium comportant au moins une fonction solubilisante non-basique
US10/089,193 US6953584B1 (en) 1999-09-27 1999-09-27 Cosmetic compositions based on organic silicon compounds comprising at least a non basic solubilising function
ES99946238T ES2260935T3 (es) 1999-09-27 1999-09-27 Composicion cosmetica a base de compuestos organicos de silicio que comprenden al menos una funcion solubilizante no basica.
PCT/FR1999/002290 WO2001022931A1 (fr) 1999-09-27 1999-09-27 Composition cosmetique a base de composes organiques du silicium comportant au moins une fonction solubilisante non-basique
JP2001526143A JP2003510261A (ja) 1999-09-27 1999-09-27 少なくとも一つの非塩基性で可溶化性の官能基を含む有機ケイ素化合物をベースとする化粧品組成物
AU58679/99A AU5867999A (en) 1999-09-27 1999-09-27 Cosmetic compositions based on organic silicon compounds comprising at least a non-basic solubilising function
BR9917504-5A BR9917504A (pt) 1999-09-27 1999-09-27 Composição cosmética

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/FR1999/002290 WO2001022931A1 (fr) 1999-09-27 1999-09-27 Composition cosmetique a base de composes organiques du silicium comportant au moins une fonction solubilisante non-basique

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WO2001022931A1 true WO2001022931A1 (fr) 2001-04-05

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US (1) US6953584B1 (enExample)
EP (1) EP1216022B1 (enExample)
JP (1) JP2003510261A (enExample)
AU (1) AU5867999A (enExample)
BR (1) BR9917504A (enExample)
CA (1) CA2385913A1 (enExample)
DE (1) DE69930971T2 (enExample)
ES (1) ES2260935T3 (enExample)
WO (1) WO2001022931A1 (enExample)

Cited By (8)

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Publication number Priority date Publication date Assignee Title
EP2246039A1 (fr) * 2009-04-30 2010-11-03 L'Oréal Procédé de coloration des cheveux comprenant une étape de traitement des cheveux à partir d'un composé organique du silicium
US9474700B2 (en) 2012-11-09 2016-10-25 L'oreal Methods for altering the color and appearance of hair
US9565916B2 (en) 2011-11-09 2017-02-14 L'oreal Compositions and methods for altering the appearance of hair
US9566221B2 (en) 2012-11-09 2017-02-14 L'oreal Methods for altering the color and appearance of hair
US9565915B2 (en) 2011-11-09 2017-02-14 L'oreal Compositions and methods for altering the appearance of hair
US10085927B2 (en) 2009-01-30 2018-10-02 L'oreal Nondetergent cosmetic compositions comprising at least one alkoxysilane and at least one microbial gum and styling uses
US10524999B2 (en) 2015-12-14 2020-01-07 L'oreal Composition comprising a combination of particular alkoxysilanes and a fatty substance
US11395794B2 (en) 2015-12-14 2022-07-26 L'oreal Process for treating keratin fibres using an aqueous composition comprising a combination of particular alkoxysilanes

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US20050208005A1 (en) * 2003-08-11 2005-09-22 Franck Giroud Cosmetic composition comprising particles having a core-shell structure
KR20060134988A (ko) 2004-04-07 2006-12-28 카오카부시키가이샤 모발 처리제 및 모발 처리 방법
JP4509769B2 (ja) * 2004-12-28 2010-07-21 花王株式会社 毛髪改質方法
JP4509760B2 (ja) * 2004-12-08 2010-07-21 花王株式会社 毛髪化粧料
JP4509729B2 (ja) * 2004-04-07 2010-07-21 花王株式会社 毛髪化粧料
JP4883964B2 (ja) * 2005-09-12 2012-02-22 花王株式会社 毛髪化粧料
JP4989058B2 (ja) * 2005-10-06 2012-08-01 花王株式会社 毛髪化粧料
FR2910275B1 (fr) * 2006-12-20 2010-06-04 Oreal Utilisation d'une silicone dans une composition de mise en forme des cheveux comprenant une alcoxysilane contenant un groupe fonctionnel solubilisant
FR2910311B1 (fr) 2006-12-20 2009-02-13 Oreal Composition comprenant un compose silicone et un organosilane particulier
EP2635253A4 (en) 2010-11-02 2014-04-02 Oreal NITRATE CELLULOSE FREE NAIL POLISH COMPOSITIONS
US8556994B2 (en) 2011-12-30 2013-10-15 L'oreal Process for altering the appearance of hair using a composition containing direct dyes and non-hydroxide bases
WO2013098332A2 (en) 2011-12-30 2013-07-04 L'oreal Composition and process for reducing the curl and frizziness of hair
US8343238B1 (en) 2011-12-30 2013-01-01 L'oreal Sa. Process for altering the appearance of hair using a composition containing dyes and non-hydroxide bases
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
US8591872B2 (en) 2011-12-30 2013-11-26 L'oreal Composition and process for reducing the curl and frizziness of hair
US10596100B2 (en) 2012-12-19 2020-03-24 L'oreal Cosmetic compositions containing an alkoxysilane and a silsesquioxane resin
US9084733B2 (en) 2013-12-09 2015-07-21 L'oreal Cleansing composition with cationic silanes and silicones
EP3288520A4 (en) 2015-05-01 2018-12-12 L'oreal Use of active agents during chemical treatments
JP6873994B2 (ja) 2015-11-24 2021-05-19 ロレアル 毛髪を処置するための組成物
WO2017091797A1 (en) 2015-11-24 2017-06-01 L'oreal Compositions for treating the hair
US10576307B2 (en) 2017-05-24 2020-03-03 L'oreal Hair-treatment compositions, methods, and kits for treating hair
US10561599B2 (en) 2017-05-24 2020-02-18 L'oreal Methods and kits for treating chemically relaxed hair
US9974725B1 (en) 2017-05-24 2018-05-22 L'oreal Methods for treating chemically relaxed hair
WO2019133785A1 (en) 2017-12-29 2019-07-04 L'oreal Compositions for altering the color of hair
US11090249B2 (en) 2018-10-31 2021-08-17 L'oreal Hair treatment compositions, methods, and kits for treating hair
US11419809B2 (en) 2019-06-27 2022-08-23 L'oreal Hair treatment compositions and methods for treating hair

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10085927B2 (en) 2009-01-30 2018-10-02 L'oreal Nondetergent cosmetic compositions comprising at least one alkoxysilane and at least one microbial gum and styling uses
EP2246039A1 (fr) * 2009-04-30 2010-11-03 L'Oréal Procédé de coloration des cheveux comprenant une étape de traitement des cheveux à partir d'un composé organique du silicium
FR2944961A1 (fr) * 2009-04-30 2010-11-05 Oreal Procede coloration des cheveux comprenant une etape de traitement des cheveux a partir d'un compose organique du silicium
US7959687B2 (en) 2009-04-30 2011-06-14 L'oreal, S.A. Hair dyeing process comprising a post-treatment using at least one organic silicon compound
US9565916B2 (en) 2011-11-09 2017-02-14 L'oreal Compositions and methods for altering the appearance of hair
US9565915B2 (en) 2011-11-09 2017-02-14 L'oreal Compositions and methods for altering the appearance of hair
US9578944B2 (en) 2011-11-09 2017-02-28 L'oreal Compositions and methods for altering the appearance of hair
US9474700B2 (en) 2012-11-09 2016-10-25 L'oreal Methods for altering the color and appearance of hair
US9566221B2 (en) 2012-11-09 2017-02-14 L'oreal Methods for altering the color and appearance of hair
US10524999B2 (en) 2015-12-14 2020-01-07 L'oreal Composition comprising a combination of particular alkoxysilanes and a fatty substance
US11395794B2 (en) 2015-12-14 2022-07-26 L'oreal Process for treating keratin fibres using an aqueous composition comprising a combination of particular alkoxysilanes

Also Published As

Publication number Publication date
DE69930971T2 (de) 2007-04-12
AU5867999A (en) 2001-04-30
US6953584B1 (en) 2005-10-11
ES2260935T3 (es) 2006-11-01
JP2003510261A (ja) 2003-03-18
EP1216022B1 (fr) 2006-04-19
CA2385913A1 (fr) 2001-04-05
DE69930971D1 (de) 2006-05-24
BR9917504A (pt) 2002-08-13
EP1216022A1 (fr) 2002-06-26

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