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EP1799309A1 - Deodorants et antitranspirants aerosol contenant du chitosane - Google Patents

Deodorants et antitranspirants aerosol contenant du chitosane

Info

Publication number
EP1799309A1
EP1799309A1 EP05799527A EP05799527A EP1799309A1 EP 1799309 A1 EP1799309 A1 EP 1799309A1 EP 05799527 A EP05799527 A EP 05799527A EP 05799527 A EP05799527 A EP 05799527A EP 1799309 A1 EP1799309 A1 EP 1799309A1
Authority
EP
European Patent Office
Prior art keywords
chitosan
preparation according
molecular weight
weight distribution
chitosans
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Withdrawn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
EP05799527A
Other languages
German (de)
English (en)
Inventor
Thomas Nuebel
Stefan Biel
Cornelia Meier-Zimmerer
Melanie Maurath
Ulrich Kux
Yvonne Cierpisz
Heike Foelster
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.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
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 Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP1799309A1 publication Critical patent/EP1799309A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • 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
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/86—Products or compounds obtained by genetic engineering

Definitions

  • Aerosol deodorants and antiperspirants containing chitosan Aerosol deodorants and antiperspirants containing chitosan
  • the invention relates to aerosol deodorants and antiperspirants with a proportion of chitosan.
  • antiperspirants in so-called antiperspirants (AT), astringents-predominantly aluminum salts, such as aluminum hydroxychloride (aluminum chlorohydrate, ACH or activated ACH-AACH) or aluminum-zirconium salts (AZG), can reduce the formation of perspiration.
  • ALCG aluminum-zirconium salts
  • Cosmetic deodorants are used to eliminate body odor that occurs when the odorless fresh sweat is decomposed by microorganisms.
  • the usual cosmetic deodorants are based on different active principles.
  • the bacterial flora on the skin can be reduced. Ideally, only the odor causing microorganisms should be effectively reduced.
  • the sweat flow itself is not affected, in the ideal case, only the microbial decomposition of the sweat is temporarily stopped.
  • Deodorants should fulfill the following conditions:
  • liquid deodorants for example roll-ons and solid preparations, for example deodorant sticks (sticks), powders, powder sprays, intimate cleaners, etc., as well as aerosol sprays, are known and commonly used.
  • An aerosol is a disperse system in which a solid or liquid is extremely finely dispersed in a gas.
  • the aerosol is usually only when using a suitable spray system by spraying solutions, emulsions or suspensions self-produced, including, for example, spray cans can be used, in which a liquefied compressed gas serves as a propellant gas.
  • Pressure valve escapes the propellant-preparation mixture through a fine nozzle, the propellant evaporates and leaves the finely divided spray as an aerosol.
  • Active substances can be present in aerosol formulations both dissolved and in solid form; if they are in solid form, they must, however, be suspended in the propellant system accordingly.
  • Aerosol products for the regulation of axillary sweat production contain antiperspirant active ingredients usually as solids suspended in an oil phase.
  • silicates such as bentonites or aerosils
  • these excipients have the disadvantages that they can inactivate the De-AT drugs by adsorption, that they are water-insoluble and contribute to the whiteness on the skin.
  • a further disadvantage of such formulations is that the metal cans which are generally used as containers can corrode due to the separation of residual water from the oil phase, specifically the higher the corrosivity of the auxiliary agents, additives and / or active ingredients used. It is therefore common and usually necessary to paint the used cans from the inside.
  • Chitosan is described as a potent Deowirker because of its anti-adhesive effect. Since chitosan can not be dissolved in alcohol, but for the deodorant action must be present in the dissolved state, it has not been possible to formulate alcoholic deodorant aerosols without the addition of water and / or emulsifiers with chitosan as the main Deowirker.
  • the water-soluble polymers such as chitosan, celluloses, polyurethanes, carbomers are not difficult or difficult to formulate in anhydrous aerosol products of the prior art because of a lack of water phase.
  • WO 01070191 describes the use of nanoscale chitosans in AT aerosol products which are predominantly anhydrous.
  • the object of the present invention is therefore to provide deodorant and / or AT aerosols in which
  • Chitosans are partially deacetylated chitins of different molecular weights containing the idealized monomer component. In contrast to most hydrocolloids, which are negatively charged in the range of biological pH values, the The chitosans to be used are cationic compounds under these conditions. The positively charged chitosans can interact with oppositely charged surfaces and are therefore commonly used in cosmetic hair and body care products. Surveys on this topic are, for example, by B.Gesslein et al. in HAPPI 27, 57 (1990), O. Sakkaudud in Drug Cosm. Ind. 148, 24 (1991) and E. Onsoyen et al.
  • chitosans For the production of chitosans is based on chitin, preferably the shell remains of crustaceans, which are available as cheap raw materials in large quantities.
  • the chitin is usually initially deproteinized by the addition of bases, demineralized by the addition of mineral acids and finally deacetylated by the addition of strong bases.
  • chitosans in deodorants has been repeatedly described in the prior art, whereby very different chitosans can be used which differ in their polymer, monomer and molecular parameters.
  • EP 857057 discloses deodorizing preparations containing chitosan, aluminum chlorohydrate and esterase inhibitors.
  • DE 10014529 discloses deodorant formulations with nanoscale chitosans, with a diameter of 1 to 300 nm.
  • the chitosans herein have an average molecular weight of 50,000 to 2,000,000 daltons (Da), a Brookfield viscosity of less than 5,000 mPas and a degree of deacetylation in the range from 80 to 88%.
  • DE 4442987 discloses cosmetic compositions containing cationic biopolymers, chitosans, with an average molecular weight of 10,000 to 2,000,000 Daltons, a Brookfield viscosity (1 wt .-% in glycolic acid) in the range of 20,000 to 30,000 mPas.
  • the subject matter of the publication "Chitin, Chitosan, and Related Enzymes” (Ed. John P. Zikakis, New York, Academic Press, 1984, pp. XVII to XXIV and pp. 239 to 255) describes degradation products of chitin which have a degree of deacetylation which is extremely low at just 17.1%. However, such products are completely insoluble in organic acids.
  • FR-A 2701266 likewise discloses degradation products which are obtained by first pretreating chitin with hydrochloric acid and subsequently deacetylating it with sodium hydroxide solution as far as possible. There are obtained products with a degree of deacetylation of 92%, which are characterized by a very low calcium carbonate content, are readily soluble in organic acids and thereby give low-viscosity products. Of crucial disadvantage, however, again, the molecular weight is very low due to the drastic degradation conditions and again the film-forming properties of the final products are unsatisfactory.
  • the cationic biopolymers of the prior art can be divided into two groups: the first group of products include those which have a high degree of deacetylation, are soluble in organic acids and form low-viscosity solutions, but do not have sufficient film-forming Features.
  • the second group include products that have been deacetylated only to a small extent, have a higher molecular weight and good film-forming properties, but are at most difficult to dissolve in organic acids and therefore not be assembled.
  • the prior art products have a number of other disadvantages: they are usually highly discolored as a result of drastic degradation, not acceptable to the odor, and poor in storage stability, i. the viscosity does not remain with longer storage time, but decreases.
  • the addition of preservatives is required, although not welcome, as the products are susceptible to contamination by microorganisms.
  • the object of the present invention is therefore also to provide stable deodorant / AT formulations with chitosan in which the cationic biopolymer chitosan can be incorporated stably into aerosols.
  • chitosans are used in a wide variety of cosmetic formulations.
  • the formulations described, for example, in DE 10208550 or EP 1384404 comprise chitosans having a molecular weight of 800,000 to 1,200,000 Da or oligosaccharides with 1 to 50 monomers and a molecular weight below 10,000 Da. Chitosans in these areas have no anti-adhesive activity, especially against gram-positive bacteria, and show no sweat odor-reducing effect, especially in cosmetic formulations.
  • the bundle is solved by objects by an aerosol formulation according to claim 1.
  • Subject of the dependent claims are advantageous embodiments of the preparation according to the invention.
  • the invention comprises the use of such preparations and the use of chitosans and antiperspirant or deodorant active ingredients for the preparation of aerosol formulations.
  • an aerosol preparation comprising one or more antiperspirant and / or deodorant active ingredients and also chitosan or chitosan derivatives
  • A is a degree of deacetylation of 75% to 99%, preferably 78 to 86%, in particular 82 to 85% or 82 to 84%, and 80 to 99%, preferably 92 to 99%.
  • B has a viscosity of up to 10 mPas, in particular of 5 to 10 mPas, preferably 5 to 8 mPas,
  • C is a weight average molecular weight distribution of less than 300,000
  • Chitosans which are composed of at least 8, preferably at least 15, in particular at least 50, monomers are preferred.
  • chitosan or chitosan derivatives having a deacetylation degree (A) of 80 to 99%, a viscosity (B) of up to 10 mPas, a weight average molecular weight distribution (C) of 10,000 to 300,000 Da and a number average molecular weight distribution (D) of 1,000 to 50,000 da.
  • A deacetylation degree
  • B viscosity
  • C weight average molecular weight distribution
  • D number average molecular weight distribution
  • the chitosan or the chitosan derivatives have been advantageously prepared of maritime origin or enzymatically via genetically modified microorganisms, wherein the chitosans or chitosan derivatives may be protonated, partially protonated or unprotonated.
  • the protonated, partially protonated and unprotonated forms of chitosans are hereby subsumed.
  • the essential parameters of the chitosan or the chitosan derivatives according to the invention are determined as follows.
  • the viscosity of a 1% solution is measured according to Brookfield in 1% acetic acid at 25 ° C.
  • the molecular weight is determined according to GPC analysis in a 0.1 molar NaCl / 0.1 vol.% Trifluoroacetic acid solution at 23 ° C with a PSS-Novema column (10 ⁇ m, linear, ID 8.0 mm x 300 mm) Flow of 1.0 ml / min, a sample concentration of 2.0 g / l and an injection volume of 20 ul determined.
  • the degree of deacetylation can be determined by the direct titration method.
  • the invention particularly efficient acting chitosans have a molecular weight between 10,000 to 300,000 Da, in particular between 50,000 - 160,000 Da, a degree of deacetylation of 75 to 99%, a viscosity of not more than 10 mPas, a number average molecular weight distribution less than 50,000 Da and set from at least 8, in particular at least 15, preferably at least 50 monomers together.
  • chitosans according to the invention or their derivatives with the following combinations of preferred parameter ranges A, B, C and D can be selected, produced and used individually for the specific application.
  • chitosan and its derivatives especially short chain chitosan hydrochloride (MW ⁇ 100 kDa), have the excellent property of keeping the solids content in aerosols in a loose, easily shaken state.
  • AT active ingredients and / or perfume oils are not inaktierviert or changed by the addition of chitosan, what it was compared to the prior art to improve. Due to the good solubility in water of the chitosans according to the invention or their derivatives, furthermore, the whitening effect after application to the skin is greatly reduced.
  • the short-chain chitosans preferably as hydrochloride, preferably with a MW ⁇ 100 kDa, are able to develop a deodorant effect from preferably alcoholic deo-aerosols, although chitosan is not dissolved here, i. in suspension.
  • preparations according to the invention are extremely stable.
  • stability is to be understood in particular as meaning that the preparations either do not damage or corrode the aerosol containers and / or that the preparations remain stable after addition of the propellant gas.
  • the proportion of chitosan in the preparation according to the invention is preferably from 0.001 to 2% by weight, based on the total mass of the preparation. Preferably, a proportion in the range of 0.01 to 1 wt.%, Preferably 0.025 to 0.3 wt.%.
  • the formulations according to the invention comprising the chitosans defined according to the invention or their derivatives, have a better, faster and longer lasting deodorizing power than formulations containing chitosans which do not have these parameters.
  • the chitosans according to the invention are distinguished by the fact that they have no or less than 10% killed bacteria in live / dead staining tests.
  • the samples are stained with two different fluorescent dyes.
  • Syto 9 generally stains all cells of the sample (green fluorescence), whereas propidium iodide only stains cells with damaged cell membrane (red fluorescence).
  • red fluorescence By a suitable mixing ratio of the two dyes can be differentiated due to the different fluorescence between living (green) and dead cells (red).
  • SYBR Green II is a DNA-specific dye that stains bacterial cells green and is often used to determine bacterial titers.
  • the bacterial cells are green fluorescent after staining.
  • the chitosan structures were red-stained with WGA-Texas Red, which allowed determination of the number of bound bacteria to the chitosan structures.
  • the chitosan according to the invention with the specific parameters is not responsible for destruction or killing of the bacteria. Rather, it has been shown that the chitosans according to the invention in combination with corneocytes and bacteria are present as chitosan structures both in vitro and in rinses on the test subject, in which 10-10,000, in particular 10-1,000, are bound to bacteria, i. there is a binding of the bacteria to or in the chitosans according to the invention.
  • the bacteria in the chitosan structures are 90% vital, these chitosan structures nevertheless lead to a bacterial metabolism of the sweat can no longer occur. That is, the chitosans or their derivatives according to the invention have no killing effect, which in turn promises a mildness to the skin for the preparations according to the invention, and yet a microbial decomposition of perspiration is temporarily stopped.
  • Long-term effect here means an effect that lasts for a period of several hours, in particular more than 24 hours.
  • Long-term effect means that chitosan-containing deodulations achieve a higher reduction in the SNIFF score after 24 hours than after 4 hours.
  • the 4-hour SNIFF score is higher than the SNIFF score after 24 hours.
  • the specific chitosans or their derivatives show no killing effect on bacteria, which in turn promises a mildness to the skin for the preparations according to the invention, since the skin flora remains in their natural equilibrium and is thus in no way restricted in their function.
  • Chitosans of the prior art for example, with MW over 300,000 Da, do not show the described effect of vitality maintenance of the bacteria.
  • chitosan-containing aerosol preparations which are deodorizing, skin-friendly, skin-care and, above all, stable and remain effective for up to 24 h.
  • the chitosan or chitosan derivatives according to the invention having a degree of deacetylation of 75% to 98%, a viscosity of up to 10 mPas, a weight average molecular weight distribution of less than 300,000 Da, a number average molecular weight distribution of less than 100,000 Da, composed of at least 15 monomers
  • antiperspirant active ingredients preferably aluminum chlorohydrate and / or activated aluminum chlorohydrate
  • chitosans with the listed properties of low molecular weight, low viscosity and high deacetylation, stable cosmetic aerosol formulations produce that the disadvantages of the prior Do not have technology.
  • an antiperspirant active it is advantageous to incorporate acidic aluminum and / or aluminum salts in aqueous solution.
  • concentration ranges described relate to the so-called active contents of the antiperspirant complexes: in the case of the aluminum compounds, to anhydrous complexes or buffer-free complexes.
  • the buffer used here is usually glycine.
  • glycine-free aluminum salts can also be used.
  • chitosan invention aerosol preparations can be prepared by the addition of chitosan invention aerosol preparations, with a preferred proportion of antiperspirant active ingredients in the range of 1 to 35 wt.%, Preferably from 1 to 25 wt.%, Particularly preferably from 1 to 20 wt.%, Based on the Total mass of the preparation.
  • antiperspirant active ingredients in which case aluminum chlorohydrate (ACH), in a 50% aqueous solution, whose proportion is then preferably in the range from 10 to 50% by weight, in particular in the range from 16 to 45% by weight, is preferred.
  • ACH aluminum chlorohydrate
  • the AT active ingredients in combination with the chitosans according to the invention or their derivatives in aerosols can be kept in a loose, easily Anlagenschütelnden state. And in particular even with prolonged upright storage of the aerosol containers, the AT active substance does not form, as usual, a solid sediment that can not be resuspended by shaking.
  • the Seaein on the skin or clothing of the applied aerosol product is thereby reduced at the same time.
  • formulations according to the invention may also be added to deodorants or instead of the AT agents.
  • the bacterial flora on the skin can be reduced. Ideally, only the odor causing microorganisms should be effectively reduced.
  • the sweat flow itself is not affected, in the ideal case, only the microbial decomposition of the Sweat temporarily stopped.
  • the combination of astringents with antimicrobial substances in one and the same composition is also common.
  • odor maskers such as the common perfume ingredients, odor absorbers, for example the sheet silicates described in DE 40 09 347, of these in particular montmorillonite, kaolinite, IIit, beidellite, nontronite, saponite, hectorite, bentonite , Smectite, furthermore, for example, zinc salts of ricinoleic acid.
  • Germ-inhibiting agents are also suitable to be incorporated in the preparations according to the invention.
  • Advantageous substances are, for example, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (Irganan), 1,6-di- (4-chlorophenylbiguanido) hexane (chlorhexidine), 3,4,4'-trichlorocarbanilide, quaternary ammonium compounds, clove oil, mint oil, thyme oil, thiethyl citrate, Famesol (3,7,11-trimethyl-2,6,10-dodecatrien-1-ol) as well as those described in DE 37 40 186, DE 39 38 140, DE 42 04 321, DE 42 29 707, DE 42 29 737, DE 42 37 081, DE 43 09 372, DE 43 24 219 described effective agents. Also, sodium bicarbonate is advantageous to use.
  • the amount of deodorants (one or more compounds) in the preparations is preferably from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight, based on the total weight of the preparation.
  • the cosmetic deodorant / AT aerosol preparations according to the invention may contain cosmetic auxiliary substances as are customarily used in such preparations, e.g. Oils, waxes, emulsifiers, minerals etc.
  • the aerosols according to the invention thus serve in particular to avoid compaction of the suspended active ingredients.
  • pressurized gas containers for the aerosols come vessels made of metal (aluminum, tinplate), protected or non-splittemdem and splintering glass or plastic in question, in their selection pressure and fracture resistance, corrosion resistance, easy filling and aesthetic aspects, handiness, printability, etc . play a role.
  • hydrophilic propellants such as carbon dioxide, can be used advantageously in the context of the present invention, when the proportion of hydrophilic gases is selected low and lipophilic propellant gas (eg., Propane / butane) is present in excess.
  • Propane, butane, isobutane or mixtures of these propellant gases are particularly preferred.
  • the gases mentioned can be used individually or in any desired mixtures with one another.
  • the concentration of the propellant gases is usually 10 to 90% by weight, preferably 40 to 80% by weight, in each case based on the total weight of the preparation.

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)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
EP05799527A 2004-10-09 2005-10-07 Deodorants et antitranspirants aerosol contenant du chitosane Withdrawn EP1799309A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004049282A DE102004049282A1 (de) 2004-10-09 2004-10-09 Kosmetische oder dermatologische Formulierung enthaltend Chitosan
PCT/EP2005/010832 WO2006040092A1 (fr) 2004-10-09 2005-10-07 Deodorants et antitranspirants aerosol contenant du chitosane

Publications (1)

Publication Number Publication Date
EP1799309A1 true EP1799309A1 (fr) 2007-06-27

Family

ID=35631017

Family Applications (2)

Application Number Title Priority Date Filing Date
EP05799527A Withdrawn EP1799309A1 (fr) 2004-10-09 2005-10-07 Deodorants et antitranspirants aerosol contenant du chitosane
EP05795638A Expired - Lifetime EP1799189B1 (fr) 2004-10-09 2005-10-07 Formulations cosmetiques contenant du chitosane

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP05795638A Expired - Lifetime EP1799189B1 (fr) 2004-10-09 2005-10-07 Formulations cosmetiques contenant du chitosane

Country Status (6)

Country Link
EP (2) EP1799309A1 (fr)
AT (1) ATE467410T1 (fr)
CH (2) CH697888B8 (fr)
DE (2) DE102004049282A1 (fr)
ES (1) ES2342950T3 (fr)
WO (2) WO2006040092A1 (fr)

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DE102005060788A1 (de) * 2005-12-16 2007-06-28 Beiersdorf Ag Verbesserte Langzeitwirkung von Antitranspirantien
US20100260689A1 (en) * 2007-11-02 2010-10-14 Beiersdorf Ag Reducing shaving frequency
AT506334B1 (de) 2008-01-22 2010-12-15 Chemiefaser Lenzing Ag Verfahren zur behandlung cellulosischer formkörper
AT507386A1 (de) * 2008-09-22 2010-04-15 Chemiefaser Lenzing Ag Verfahren zur behandlung cellulosischer formkörper
DE102010044787A1 (de) * 2010-09-09 2012-03-15 Beiersdorf Ag Makroemulsionen mit verbesserter Deodorantwirksamkeit
EP3060310A1 (fr) * 2013-10-23 2016-08-31 Unilever PLC Composition antitranspirante
DE102014221673A1 (de) 2014-10-24 2016-04-28 Henkel Ag & Co. Kgaa Chitosanhaltige schweißhemmende kosmetische Mittel, welche frei sind von Halogeniden und/oder Hydroxyhalogeniden von Aluminium und/oder Zirconium
WO2018099931A1 (fr) 2016-12-01 2018-06-07 Unilever Plc Composition antitranspirante comprenant du chitosane
RU2667130C1 (ru) * 2017-07-18 2018-09-14 Сергей Рудольфович Утц Хитозансодержащий гидрогель и способ косметического ухода за кожей с его использованием
DE202018004125U1 (de) 2018-09-05 2018-10-11 Beiersdorf Ag Alkylamidothiazole in Polypropylen-haltigen Packmitteln
US11376199B2 (en) 2019-03-12 2022-07-05 The Procter & Gamble Company Anhydrous cosmetic compositions and uses
MX2023000870A (es) 2020-07-21 2023-05-19 Chembeau LLC Formulaciones cosmeticas de diester y usos de las mismas.
DE102020214349A1 (de) * 2020-11-16 2022-05-19 Beiersdorf Aktiengesellschaft Pumpspray mit Aluminiumsalzen
FR3150117A1 (fr) * 2023-06-20 2024-12-27 L'oreal Composition cosmétique à base de chitosan et d’argile modifiée

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Also Published As

Publication number Publication date
CH697888B1 (de) 2009-03-13
CH697888B8 (de) 2009-05-29
EP1799189A2 (fr) 2007-06-27
WO2006040091A3 (fr) 2006-07-27
EP1799189B1 (fr) 2010-05-12
WO2006040092A1 (fr) 2006-04-20
CH697625B1 (de) 2008-12-31
ATE467410T1 (de) 2010-05-15
DE102004049282A1 (de) 2006-04-20
DE502005009570D1 (de) 2010-06-24
WO2006040091A2 (fr) 2006-04-20
ES2342950T3 (es) 2010-07-19

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