EP2099529A2 - Stick antitranspirant sans traces - Google Patents

Stick antitranspirant sans traces

Info

Publication number
EP2099529A2
EP2099529A2 EP07857357A EP07857357A EP2099529A2 EP 2099529 A2 EP2099529 A2 EP 2099529A2 EP 07857357 A EP07857357 A EP 07857357A EP 07857357 A EP07857357 A EP 07857357A EP 2099529 A2 EP2099529 A2 EP 2099529A2
Authority
EP
European Patent Office
Prior art keywords
antiperspirant stick
linear
antiperspirant
oil
saturated
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
EP07857357A
Other languages
German (de)
English (en)
Inventor
Bernhard Banowski
Marcus Claas
Armin Wadle
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP2099529A2 publication Critical patent/EP2099529A2/fr
Ceased 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
    • 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
    • A61K8/0216—Solid or semisolid forms
    • A61K8/0229—Sticks
    • 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
    • A61K8/31—Hydrocarbons
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone

Definitions

  • the present invention relates to an antiperspirant stick of the type of anhydrous or low-water dispersion sticks whose antiperspirant active ingredients are dispersed in a carrier consisting of a liquid, non-polar carrier material, setting fat or wax components and surfactants.
  • water-free dispersion pencils consist of a dispersion of finely divided astringent aluminum or zirconium salts in a nonpolar carrier liquid solidified by gelling agents or waxy fatty components.
  • a non-polar carrier liquids can, for example hydrocarbons or silicone oils, preferably those having boiling points below 200 0 C, or with a certain volatility, for example, cyclic siloxanes (cyclomethicone) and mixtures thereof are used with skin-softening ⁇ lkomponen- th.
  • Such anhydrous dispersion pencils occasionally have the disadvantage that the antiperspirant effect of the astringent salts does not begin rapidly and intensively enough.
  • the pens of the prior art have the further disadvantage that they leave a more or less significant residue on the skin and / or that they heavily contaminate the clothing that comes into contact with the treated skin areas. It has already been achieved by the addition of surfactants, a hydrophilization of the stick mass and also improves the washability of the residues from the skin or garments.
  • antiperspirant sticks which contain up to 5 wt .-% of a fatty alcohol polyglycol ether.
  • EP 491843 B1 discloses antiperspirant stick compounds which contain an adduct of 10 mol of propylene oxide and butanediol to reduce the whitening effect.
  • EP 777463 B1 discloses antiperspirant sticks which contain a 1,1-12-dihydroxystearic acid as the setting fat or wax component.
  • Cyclotetrasiloxane, cyclopentasiloxane and cyclohexasiloxane are the most commonly used commercially available cyclomethicones. Cyclotetrasiloxane whose melting point is an exceptionally high -11 0 C may result in the typical for a water-free or low-water dispersion pen higher amounts to problems in the storage stability. In addition, for toxicological reasons, it is nowadays widely discernible from the use of the cyclotetrasiloxane. The usual commercial products are almost free of cyclotetrasiloxane. Nevertheless, the substance class of cyclomethicones is a problematic raw material due to even the trace content of cyclotetrasiloxane. On the other hand, the cyclomethicones have excellent performance properties, making their replacement extremely difficult.
  • An object of the present invention was to provide an adequate replacement material for cyclomethicones in anhydrous antiperspirant sticks. Another object of the present invention was to provide a highly effective antiperspirant stick having good abrasion properties. Another object of the present invention was to provide a highly effective antiperspirant stick with low soiling behavior. Another object of the present invention was to provide a highly effective antiperspirant stick with minimized residue behavior.
  • antiperspirant sticks also have a relatively high content of liquid under normal conditions oil, selected from linear polydimethylsiloxanes having 2 to 50 siloxane units, optionally in combination with at least one below normal Conditions of liquid oil, which is selected from poly-C 2 -C 6 -olefins, which are preferably hydrogenated, solve the tasks in an excellent manner.
  • liquid under normal conditions oil selected from linear polydimethylsiloxanes having 2 to 50 siloxane units, optionally in combination with at least one below normal Conditions of liquid oil, which is selected from poly-C 2 -C 6 -olefins, which are preferably hydrogenated, solve the tasks in an excellent manner.
  • anhydrous antiperspirant sticks containing a) at least one lipid or wax component with a melting point> 3O 0 C, b) at least one liquid under normal conditions oil selected from linear polydimethylsiloxanes having 2 to 50 siloxane units, c) maximum 5 Wt .-% water, based on the total composition, d) at least one antiperspirant active ingredient.
  • normal conditions are a temperature of 20 ° C. and a pressure of 1013.25 mbar. Melting point data likewise refer to a pressure of 1013.25 mbar.
  • Antiperspirant actives that can be used in the antiperspirant sticks of the present invention include any conventional aluminum, zirconium and aluminum zirconium salts known to be useful as antiperspirant actives. These salts include aluminum halides and aluminum hydroxyhalides (e.g., aluminum chlorohydrate), and mixtures and complexes thereof with zirconyl oxyhalides and zirconyl hydroxyhalides (e.g., aluminum zirconium chlorohydrate).
  • Preferred antiperspirant active substances are selected from the water-soluble astringent inorganic and organic salts of aluminum, zirconium and zinc or any desired mixtures of these salts.
  • Particularly preferred antiperspirant active ingredients are selected from the aluminum chlorohydrates, in particular the aluminum chlorohydrates having the general formula [Al 2 (OH) 5 Cl ⁇ 2-3 H 2 O] n , which may be present in non-activated or in activated (depolymerized) form , further aluminum sesquichlorohydrate, aluminum chlorohydrex propylene glycol (PG) or polyethylene glycol (PEG), aluminum or aluminum zirconium glycol complexes, e.g.
  • solubility of at least 5 wt .-% at 20 0 C is understood according to the invention, solubility in water, that is, amounts of at least 5 g of the antiperspirant active ingredient in 95 g of water are soluble at 20 0 C.
  • the composition comprises an astringent of the aluminum salt, especially aluminum chlorohydrate, for example, in powder form under the names Micro Dry ® Ultra Fine, Micro Dry ® Super Ultra Fine, chlorohydrol ® Microdry and chlorohydrol ® Microdry Ultrafine, as well as in activated form as Reach ® 501 , Reach® 101 and Reach® 103 are sold by Reheis.
  • powdered aluminum are particularly preferred sesquichlorohydrate, such as Reach ® 301 from Reheis or "ACH-308 Alcohol Soluble Beads" from Summit Research Labs.
  • Aluminum salts are those having the general formula Al 2 (OH) 6 - a X a , in which X is Cl, Br, I or NO 3 and "a" is 0.3 to 4 and preferably 1 to 2, so that Molar ratio of Al to X in the range of 1: 1 to 2.1: 1.
  • these salts contain water of crystallization, typically of the order of 1 to 6 moles of water per mole of salt.
  • zirconium salts are mixtures or complexes of the aluminum salts described above with zirconium salts of the formula ZrO (OH) 2 _ pb Y b wherein Y is Cl, Br, I, NO 3 or SO 4, "b" 0.8 to 2 and "p” is the valence of Y.
  • the zirconium salts usually contain some water of crystallization, typically of the order of 1 to 7 moles of water per mole of salt.
  • the zirconium salt is zirconyl hydroxychloride of the formula ZrO (OH) 2. b Cl b , wherein "b” is 1 to 2 and preferably 1, 2 to 1, 9.
  • the preferred aluminum-zirconium salts have an Al: Zr ratio of 1.7 to 12.5, and most preferably 2 to 10, and a metal / (X + Y) ratio of 0.73 to 2.1, and preferably 0 , 9 to 1, 5.
  • a preferred salt is aluminum-zirconium chlorohydrate (ie, X and Y are Cl) having an Al: Zr ratio of 2 to 10 and a metal: Cl ratio of 0.9 to 2.1, preferably 0.95 to 1. 5, more preferably 1 - 1, 3, having.
  • aluminum zirconium chlorohydrate the forms tri-, tetra-, penta- and octachlorohydrate should be included.
  • the aluminum-zirconium salt complexes can also contain a neutral amino acid, preferably glycine, typically having a Gly: Zr ratio of about 1: 1, ie 0.8-1.2, more preferably 1.
  • Preferred antiperspirant sticks according to the invention are characterized in that the at least one antiperspirant active ingredient is present in an amount of 3 to 27% by weight, preferably 5 to 25% by weight, more preferably 8 to 22% by weight and most preferably 18% by weight. 20 wt .-%, based on the total weight of the active substance (USP, US Pharmacopoeia) in the total composition.
  • the amount of antiperspirant salt (s) indicated in the instant application is to be calculated according to the method of US Pharmacopoeia (USP) according to which the weight of the bound water of crystallization and other ligands, e.g. As glycine, is not considered.
  • USP US Pharmacopoeia
  • astringent salts are coated or impregnated with a water-soluble, nonionic surfactant.
  • Particularly suitable surfactants for this purpose have been found to be alkyl (oligo) glycosides.
  • Particularly preferred is a coating or impregnation with alkyl (oligo) glycosides, which were applied in amounts of 0.1 to 5 wt .-% to the surface of the salt particles.
  • the stick compositions of the invention may contain both at least one deodorant and at least one antiperspirant active.
  • the water of crystallization entered with the antiperspirant active ingredients is not taken into account in the water content of the pencil.
  • pens contain a maximum of 5 wt .-%, more preferably less than 3 wt .-% water, based on the total weight of the stick composition, in which case only the free water counts and not bound as water of crystallization water, for example, in the antiperspirant active ingredients is included.
  • Antiperspirant sticks preferred according to the invention are characterized in that the at least one linear polydimethylsiloxane having 2 to 50 siloxane units is selected from hexamethyldisiloxane (L 2 ), octamethyltrisiloxane (L 3 ), decamethyltetrasiloxane (L 4 ), dodecamethylpenta- siloxane (L 5 ) , any two, three and four mixtures of L 2 , L 3 , L 4 and / or L 5 , linear polydimethylsiloxanes having 6 to 50 siloxane units, preferably 7 to 45 siloxane units, more preferably 8 to 40 siloxane units, most preferably 9 to 35 siloxane units.
  • Further preferred linear polydimethylsiloxanes are selected from those having 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 and 20 siloxane units.
  • Other preferred linear polydimethylsiloxanes are selected from those having 21, 22, 23, 24, 25, 26, 27, 28, 29 and 30 siloxane units.
  • Other preferred linear polydimethylsiloxanes are selected from those having 31, 32, 33, 34, 35, 36, 37, 38, 39 and 40 siloxane units.
  • linear polydimethylsiloxanes are commercially available.
  • the commercial products contain mixtures of linear polydimethylsiloxanes with different numbers of siloxane units.
  • the specification of the commercial products is based more on the (kinematic) viscosity (at 25 ° C.) than on the number of siloxane units.
  • hexamethyldisiloxane z. B. as product Dow Corning ® 200 (0.65 cSt) with a kinematic viscosity (at 25 0 C) of 0.65 cSt sold.
  • Octamethyltrisiloxane is z. B.
  • Dow Corning® 200 (1 cst) having a kinematic viscosity (at 25 0 C) of 1 cSt.
  • Other commercial products such as Dow Corning® 200 (1.5 cSt), with an average kinematic viscosity of 1.35- 1.65 cSt (25 ° C.), are mixtures of linear polydimethylsiloxanes having different numbers of siloxane units: Dow Corning® 200 (1, 5 cSt) z. B. contains predominantly polydimethylsiloxanes with 3 and 4 siloxane units.
  • Corresponding inventively preferred linear polydimethylsiloxanes are z. B. in the commercial products DC 2-1184, Dow Corning ® 200 (0.65 cSt), Dow Corning ® 200 (1, 0 cSt), Dow Corning ® 200 (1, 5 cSt), Dow Corning ® 200 (2 cSt ) and Dow Corning® 200 (5 cSt) from Dow Corning.
  • linear polydimethylsiloxanes mixtures having a kinematic viscosity (25 0 C) from 0.65 to 8 cSt, and particularly preferably 25 cSt comprise - 10 cSt, preferably 1 - 9 cSt, more preferably 1; 5.
  • the at least one linear polydimethylsiloxane having 2 to 50 siloxane units in a total amount of 10 to 60 wt .-%, particularly preferably 20 to 50 wt .-%, most preferably 25 to 35 wt .-%, based on the total antiperspirant Pen, included.
  • Particularly preferred antiperspirant sticks of the invention comprise a mixture of linear polydimethylsiloxanes having a kinematic viscosity (25 0 C) 0.65 to 10 cSt, preferably 1 - 9 cSt, particularly preferably 1, 5-8 cSt, and particularly preferably 25 cSt, in a total amount of 10 - 60 wt .-%, particularly preferably 20 - 50 wt .-%, most preferably 25 - 35 wt .-%, based on the total antiperspirant stick.
  • Also particularly preferred antiperspirant sticks of the invention contain two mixtures of linear polydimethylsiloxanes which each have a kinematic viscosity (25 0 C) 0.65 to 10 cSt, preferably 1 - 9 cSt, particularly preferably 1, 5-8 cSt, and particularly preferably 2-5 cSt, in a total amount of 10 - 60 wt .-%, particularly preferably 20 - 50 wt .-%, most preferably 25 - 35 wt .-%, based on the total antiperspirant stick.
  • the combination of a mixture with 2 cSt and a mixture with 5 cSt is particularly preferred, in particular in a weight ratio of 1: 2 to 2: 1, particularly preferably 1: 1.
  • Also particularly preferred antiperspirant sticks of the invention comprise three mixtures of linear polydimethylsiloxanes which each have a kinematic viscosity (25 0 C) 0.65 to 10 cSt, preferably 1 - 9 cSt, particularly preferably 1, 5-8 cSt, and particularly preferably 2 - 5 cSt, in a total amount of 10 - 60 wt .-%, particularly preferably 20 - 50 wt .-%, most preferably 25 - 35 wt .-%, based on the total antiperspirant stick.
  • a kinematic viscosity 25 0 C
  • Also particularly preferred antiperspirant sticks of the invention comprise four mixtures of linear polydimethylsiloxanes which each have a kinematic viscosity (25 0 C) 0.65 to 10 cSt, preferably 1 - 9 cSt, particularly preferably 1, 5-8 cSt, and particularly preferably 2 - 5 cSt, in a total amount of 10 - 60 wt .-%, particularly preferably 20 - 50 wt .-%, most preferably 25 - 35 wt .-%, based on the total antiperspirant stick.
  • a kinematic viscosity 25 0 C
  • antiperspirant sticks are characterized in that no cyclomethicone is included.
  • antiperspirant sticks according to the invention are characterized in that at least one oil which is liquid under normal conditions and is selected from poly-C 2 -C 16 -olefins, in particular selected from polybutene, polyisobutene and polydecene, is contained.
  • the poly-C 2 -C 16 -olefin oils are in hydrogenated form. Particularly preferred are hydrogenated polybutene, hydrogenated polyisobutene and hydrogenated polydecene, and mixtures thereof.
  • the poly-C 2 -C 16 -olefin oils and the hydrogenated poly-C 2 -C 16 -olefin oils have a total carbon number of from 20 to 60, preferably from 24 to 50, particularly preferably from 30 to 40, in the molecule.
  • Particular preference is given to isoeicosane, hydrogenated polyisobutenes (INCI designation) with at least 50% by weight C 32 component, and also hydrogenated polydecenes (INCI designation) having 75-85% by weight C 30 component and 15% 25 wt .-% C 40 content, and mixtures thereof.
  • the at least one poly-C 2 -C 6 -olefin oil and / or the at least one hydrogenated poly-C 2 -C 6 -olefin oil are preferably in a total amount of 5 to 30% by weight, particularly preferably 10-25% by weight, most preferably 12-15% by weight, based on the total antiperspirant stick.
  • Extremely preferred antiperspirant sticks are by content Hydrogenated polydecenes (INCI name) with 75-85 wt .-% C 30 content and 15- 25 wt .-% C 40 content of in a total amount of 5-25 wt .-%, particularly preferably 10-18 wt %, most preferably 12-15% by weight, based on the total antiperspirant stick.
  • Further inventively preferred antiperspirant sticks are characterized in that at least one linear polydimethylsiloxane having 2 to 50 siloxane units and at least one liquid under normal conditions oil selected from poly-C 2 -C 16 -olefinen, in particular selected from polybutene, polyisobutene and polydecene containing is.
  • both classes of substance are contained in a weight ratio of about 1: 1, in particular when the linear polydimethylsiloxane is selected from L 2 and / or L 3 , and the polyolefin is selected from polydecene.
  • both substance classes linear polydimethylsiloxane, polyolefin
  • a weight ratio of about 1: 1 in particular if the linear polydimethylsiloxane is selected from those having 2 to 20 siloxane units, and the polyolefin is selected from hydrogenated polydecenes (INCI name) with 75-85% by weight of C 30 component and 15-25% by weight of C 40 component.
  • both classes of substance linear polydimethylsiloxane, polyolefin
  • linear polydimethylsiloxane in a weight ratio of about 1: 1, especially when the linear polydimethylsiloxane is selected from those having a kinematic viscosity (25 0 C) of 0.65 - 10 cSt, preferably 1 - 9 cSt, more preferably 1, 5 - 8 cSt and most preferably 2 - 5 cSt, and the polyolefin is selected from Hydrogenated Polydecene (INCI name) with 75 - 85 wt .-% C 30 content and 15 - 25 wt .-% C 40 content.
  • kinematic viscosity 25 0 C
  • the polyolefin is selected from Hydrogenated Polydecene (INCI name) with 75 - 85 wt .-% C 30 content and 15 - 25 wt .-% C 40 content.
  • the at least one lipid or wax component a) is selected from coconut fatty acid glycerol mono-, di- and triesters, butyrospermum parkii (shea butter), esters of saturated, monohydric C 8 - Ci nolen 8 alcohols with saturated C 2 -C 8 monocarboxylic acids, linear, primary d -Alka- 2 -C 24, esters of a saturated, monohydric C 6 -C 6 o-alkanol and a saturated C 8 -C 36 - Monocarboxylic acid, in particular cetyl behenate, stearyl behenate and C 20 -C 40 -alkyl stearate, glycerol triesters of saturated linear C 2 -C 30 -carboxylic acids which may be hydroxylated, candelilla wax, carnauba wax, beeswax, saturated linear C 4 -C 36 -carboxylic
  • lipids and waxes cover a wide melting range. It is well known to those skilled in the art that for good abrasion and strength properties of the stick, the mixture of lipid or wax components must be carefully tuned with respect to their melting or melting range.
  • the lipid or wax matrix of the stick compositions according to the invention comprises at least one lipid or wax component with a melting point> 5O 0 C.
  • waxes of solid to brittle hard consistency coarse to fine crystalline, translucent to opaque, but not glassy, and melt above 50 0 C without decomposition. They are already slightly above the melting point low viscosity and show a strong temperature-dependent consistency and solubility.
  • Preference according to the invention for example, natural vegetable waxes, z. Candelilla wax, carnauba wax, Japan wax, sugarcane wax, ouricoury wax, cork wax, sunflower wax, fruit waxes such as orange waxes, lemon waxes, grapefruit wax, and animal waxes, e.g. Beeswax, shellac wax and spermaceti.
  • it may be particularly preferred to use hydrogenated or hardened waxes.
  • a wax component and chemically modified waxes especially the hard waxes, such as.
  • montan ester waxes hydrogenated jojoba waxes and Sasol waxes used.
  • Synthetic waxes which are also preferable in the invention include, for example, polyalkylene waxes and polyethylene glycol waxes, C 2 oC 4O dialkyl esters of dimer acids, C 30 - 50 alkyl and alkylaryl esters of -Alkylbienenwachs dinner as well as fatty acids.
  • a particularly preferred wax component is selected from at least one ester of a saturated monohydric C 6 -C 6 -alcohol and a saturated Cs-Cs ⁇ -monocarboxylic acid.
  • ester of a saturated monohydric C 6 -C 6 -alcohol and a saturated Cs-Cs ⁇ -monocarboxylic acid also include lactides, the cyclic double esters of ⁇ -hydroxycarboxylic acids of the corresponding chain length.
  • Esters of fatty acids and long-chain alcohols have been found to be particularly advantageous for the composition of the present invention because they give the antiperspirant preparation excellent sensory properties and overall high stability to the pin.
  • the esters are composed of saturated, branched or unbranched monocarboxylic acids and saturated, branched or unbranched monohydric alcohols.
  • esters of aromatic carboxylic acids and hydroxycarboxylic acids eg., 12-hydroxystearic acid
  • saturated, branched or unbranched alcohols are used according to the invention, provided that the wax component has a melting point> 5O 0 C.
  • the wax component C- ⁇ 6-36 alkyl stearates and C 18 - 38 -Alkylhydroxystearoyl- stearate C 20 - 40 -Alkylerucate and cetearyl be advantageous.
  • the wax or the wax components have a melting point> 5O 0 C, preferably> 6O 0 C, more preferably in the range of 75 to 95 0 C, most preferably in the range of 80 to 90 0 C, on.
  • a particularly preferred embodiment of the invention contains as wax component a C 20 -C 40 -alkyl stearate.
  • This ester is known under the name Kester ® ® K82H or Kesterwachs K80H, sold by Koster Keunen Inc.. It is the synthetic imitation of the monoester fraction of beeswax and is characterized by its hardness, oil gelability and broad compatibility with lipid components.
  • This wax can be used as a stabilizer and consistency regulator for W / O and O / W emulsions.
  • Kester wax has the advantage that it has an excellent oil gelability even at low concentrations and so does not make the pencil mass too heavy and allows a velvety abrasion.
  • a further particularly preferred embodiment of the invention contains as wax component cetearyl behenate, ie mixtures of cetyl behenate and stearyl behenate.
  • This ester is known under the name Kester ® K62 and is sold by Koster Keunen Inc..
  • lipid or wax components with a melting point> 5O 0 C are the triglycerides of saturated and optionally hydroxylated C 12 - 3 o-fatty acids, such as hardened triglyceride fats (hydrogenated palm oil, hydrogenated coconut oil, hydrogenated castor oil), glyceryl tribehenate (tribehenin), or glyceryl tri -12-hydroxystearate, furthermore synthetic full esters of fatty acids and glycols or polyols having 2-6 carbon atoms, as long as they have a melting point above 50 0 C, for example preferably C 18 - C 36 Acid triglycerides (Syncrowax ® HGL-C).
  • hardened triglyceride fats hydrogenated palm oil, hydrogenated coconut oil, hydrogenated castor oil
  • tribehenin glyceryl tribehenate
  • glyceryl tri -12-hydroxystearate furthermore synthetic full esters of fatty acids and glycols or polyols having 2-6 carbon
  • hydrogenated castor oil obtainable, for example, as wax component is available.
  • Cutina ® HR having a melting point in the range of 85 - 88 0 C, particularly preferred.
  • Other preferred lipid or wax components with a melting point> 5O 0 C the saturated linear C 14 - C 36 carboxylic acids, in particular myristic acid, palmitic acid, stearic acid and behenic acid, and mixtures of these compounds, for example.
  • Preferred antiperspirant sticks according to the invention are characterized in that the wax component a) is selected from esters of a saturated, monohydric C 12 -C 6 o-alkane nol and a saturated Cs-Cs ⁇ monocarboxylic acid, in particular lauryl laurate, lauryl myristate, lauryl palmitate, lauryl stearate, lauryl 12-hydroxystearate, lauryleicosanate, laurylbehenate, lauryl lignocerate, laurylcerate, laurylmyrate, myristyl laurate, myristyl myristate, myristyl palmitate, myristyl stearaate, myristyl-12 -hydroxystearat, Myristyleicosanat, Myristylbehenat, Myristyllignocerat, myristyl cerate, Myristylmyricat, cetyl laurate, cetyl myristate, cet
  • HEAR oil rich rapeseed oil
  • LEAR oil fully hydrogenated low-erucic rapeseed oil
  • canola oil fully hydrogenated Crambe oil
  • meadowfoam oil fully hydrogenated cottonseed oil
  • hyd whole oil fully hydrogenated thistle oil
  • sunflower oil fully hydrogenated sesame oil
  • fully hydrogenated coconut oil fully hydrogenated palm oil
  • palm kernel oil fully hydrogenated babassu oil
  • fully hydrogenated peanut oil fully hydrogenated cocoa butter, shea butter, llipebutter
  • animal fats especially tallow or Bacon
  • fully hydrogenated oils of marine origin such as swordfish oil, sardine oil, whale oil and herring oil.
  • wax component a) is selected from saturated linear C 4 -C 36 -carboxylic acids, in particular myristic acid, palmitic acid, stearic acid, 12-hydroxystearic acid, eicosanoic acid, behenic acid, lignoceric acid, ceric acid, myric acid, and Mixtures of the abovementioned acids.
  • Particularly preferred wax component mixtures a) are selected from mixtures of cetyl behenate, stearyl behenate, hardened castor oil, palmitic acid and stearic acid.
  • Further particularly preferred wax component mixtures a) are selected from mixtures comprising C 2 -C 4 -alkyl stearate, hydrogenated castor oil, palmitic acid and stearic acid. Further particularly preferred wax component mixtures a) are selected from mixtures comprising C 16 -C 2 o-Alkylbehenat, hydrogenated castor oil, palmitic acid and stearic acid. Further particularly preferred wax component mixtures a) are selected from mixtures comprising arachyl stearate, behenyl stearate, lignoceryl stearate, ceryl stearate, myricyl stearate, hydrogenated castor oil, palmitic acid and stearic acid. Further particularly preferred wax component mixtures a) are selected from mixtures comprising palmityl behenate, stearyl behenate, arachyl behenate, hardened castor oil, palmitic acid and stearic acid.
  • Particularly preferred antiperspirant sticks according to the invention are characterized in that at least one lipid or wax component with a melting point in the range of> 30 to below 5O 0 C, selected from Kokosfettchureglycerinmono- mono-, di- and triesters, Butyrospermum Parkii (Shea Butter) and esters of saturated, monohydric C 8 -C 8 alcohols with saturated C 2 - cis-monocarboxylic acids and mixtures of these substances, is contained.
  • These lower melting lipid or wax components allow for consistency optimization of the product and a minimization of the visible residue on the skin.
  • Further preferred esters of saturated, monovalent Ci 2 -Ci 8 - alcohols with saturated C 2 -C 8 monocarboxylic acids are stearyl laurate, cetearyl (z. B. Crodamol ® CSS), cetyl palmitate (z. B. Cutina ® CP) and myristyl myristate (z. B. Cetiol ® MM).
  • Preferred as lipid and wax component a) are in particular mixtures of i) at least one linear Ci 6 -C 22 -alkanol, selected from cetyl alcohol, stearyl alcohol, arachidyl alcohol and Behenylalko- hol, ii) at least one glyceryl ester having a melting point in the range of 30 - 40 0 C, preferably in the range of 30 - 32 ° C and iii) at least a wax or lipid having a melting point of more than 60 0 C, preferably in the range 70-90 0 C.
  • linear C 16 -C 22 -alkanol i) stearyl alcohol is used; Cetyl alcohol is less preferred because higher levels of cetyl alcohol adhere less well to the skin and can form a slightly crumbly residue. It is particularly preferred if, in addition to stearyl alcohol, small amounts, in particular 0.1-0.2% by weight, of behenyl alcohol are added.
  • Such mixtures i), ii) and iii) provide according to the invention preferred antiperspirant sticks with good abrasion, excellent residue behavior, very good antiperspirant effect and good strength.
  • Preferred antiperspirant sticks according to the invention are characterized in that the lipid or wax component a) in total amounts of 18-30% by weight, preferably 20-25% by weight, particularly preferably 22-24% by weight, in each case based on the total weight of the antiperspirant stick.
  • the antiperspirant effect and / or the application behavior of the antiperspirant sticks according to the invention can be further improved by adding an oil-in-water emulsifier.
  • an oil-in-water emulsifier Mainly for reasons of skin compatibility, nonionic oil-in-water emulsifiers are preferred.
  • antiperspirant sticks according to the invention are therefore characterized in that at least one, preferably nonionic, oil-in-water emulsifier is present.
  • Oil-in-water emulsifiers are not part of the claimed lipid or wax component a) having a melting point above 30 0 C.
  • Suitable water-soluble surfactants are in principle all those in the system to 1 wt .-% at 2O 0 C soluble and in water at 2O 0 C to at least 1 wt .-% of soluble surfactants. Although structure and ionogeneity are insignificant per se, nonionic surfactants, in particular the solid adducts of ethylene oxide with fatty acid molecules having at least one alkoxylable group, which are solid under normal conditions, appear to be particularly suitable.
  • Such suitable surfactants are, for example, the addition products of 10 to 40 mol of ethylene oxide to linear fatty alcohols having 16 to 22 carbon atoms, to fatty acids having 12 to 22 carbon atoms, to fatty acid alkanolamides, to fatty acid monoglycec ride, on sorbitan fatty acid monoesters, on fatty acid alkanolamides, on fatty acid glycerides, eg on hardened castor oil, on methyl glucoside monofatty acid esters and mixtures thereof.
  • the nonionic oil-in-water emulsifier is particularly preferably selected from surface-active substances having an HLB value of more than 7, selected from: ethoxylated C 8 -C 24 -alkanols with an average of 10 to 100 moles of ethylene oxide per mole, ethoxylated C 8 -C 24 carboxylic acids with an average of 10 to 100 moles of ethylene oxide per
  • Alkyl mono- and oligoglycosides having 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs, ethoxylated sterols,
  • Partial esters of polyglycerols having n 2 to 10 glycerol units and esterified with 1 to 4 saturated or unsaturated, linear or branched, optionally hydroxylated C 8 - C 30 fatty acid residues, if they have an HLB value of more than 7, and mixtures of the aforementioned substances.
  • the ethoxylated C 8 -C 24 -alkanols have the formula R 1 O (CH 2 CH 2 O) n H, where R 1 is a linear or branched alkyl and / or alkenyl radical having 8-24 carbon atoms and n, the middle one Number of ethylene oxide units per molecule, for numbers from 10 to 100, preferably 10 to 30, moles of ethylene oxide to 1 mole of caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, isocetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, Elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and cetearyl alcohol, and technical mixtures thereof. Also adducts of 10-100
  • the ethoxylated C 8 -C 24 carboxylic acids have the formula R 1 O (CH 2 CH 2 O) n H, where R 1 O is a linear or branched saturated or unsaturated acyl radical having 8-24 carbon atoms and n, the middle ( weight average) number of ethylene oxide units per molecule, for numbers from 10 to 100, preferably 10 to 50, more preferably 30 to 40, moles of ethylene oxide to 1 mole of caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, cetylic acid, palmitoleic acid , Stearic acid, isostearic acid, oleic acid, elaidic acid, petrose lynic acid, arachyic acid, gadoleic acid, behenic acid, erucic acid and brassidic acid and their technical mixtures.
  • Adducts of 10 to 100 mol of ethylene oxide with technical fatty acids containing 12 to 18 carbon atoms, such as coconut, palm, palm kernel or tallow fatty acid are also suitable. Particularly preferred are PEG-40 monostearate, PEG-50 monostearate, PEG-100 monostearate, PEG-40 monooleate, PEG-50 monooleate, PEG-100 monooleate, PEG-40 monolaurate, PEG-50 monolaurate and PEG-100 monolaurate.
  • C 12 -C 18 -alkanols or the C 12 -C 18 -carboxylic acids with in each case 10 to 40 units of ethylene oxide per molecule and also mixtures of these substances, in particular ceteth-12, ceteth-20, isoceteth-20, ceteth- 30, steareth-12, steareth-20, steareth-30, ceteareth-12, ceteareth-20, ceteareth-30, laureth-12, beheneth-20 and PEG-40 monostearate.
  • C 8 -C 22 -alkyl mono- and -oligoglycosides preference is given to using C 8 -C 22 -alkyl mono- and -oligoglycosides.
  • C 8 -C 22 -alkyl mono- and oligoglycosides are known, commercially available surfactants and emulsifiers. They are prepared in particular by reacting glucose or oligosaccharides with primary alcohols having 8-22 carbon atoms.
  • the glycoside radical both monoglycosides in which a cyclic sugar radical is glycosidically linked to the fatty alcohol and oligomeric glycosides having a degree of oligomerization of up to about 8, preferably 1-2, are suitable.
  • the degree of oligomerization is a statistical mean, which is based on a homolog distribution typical for such technical products.
  • Particularly preferred C 8 -C 22 alkyl mono- and oligoglycosides are selected from octyl glucoside, decyl glucoside, lauryl glucoside, palmityl glucoside, isostearyl glucoside, stearyl glucoside, arachidyl glucoside and behenyl glucoside and mixtures thereof.
  • the glucamine-derived acylglucamides are also suitable as nonionic oil-in-water emulsifiers.
  • Ethoxylated sterols in particular ethoxylated soy sterols, are also suitable oil-in-water emulsifiers according to the invention.
  • the degree of ethoxylation must be greater than 5, preferably at least 10, in order to have an HLB value greater than 7.
  • Suitable commercial products are, for. PEG-10 Soy Sterol, PEG-16 Soy Sterol and PEG-25 Soy Sterol.
  • partial esters of polyglycerols having 2 to 10 glycerol units and having 1 to 4 saturated or unsaturated, linear or branched, optionally hydroxylated C 8 -C 30 -fatty acid radicals are preferably used if they have an HLB value of more than 7 ,
  • Particularly preferred Diglycerinmonocaprylat, Diglycerinmonocaprat, Diglycerinmono- are laurate, Triglycerinmonocaprylat, Triglycerinmonocaprat, triglycerol, Tetraglycerinmono- caprylate, cerinmonocaprat Tetraglycerinmonocaprat, Tetraglycerinmonolaurat, Pentaglycerinmonocaprylat, Pentagly-, Pentaglycerinmonolaurat, Hexaglycerinmonocaprylat, Hexaglycerinmonocaprat, Hexaglycerinmonolaurat, Hexaglycerinmonomyrist
  • antiperspirant sticks according to the invention are characterized in that the at least one oil-in-water emulsifier is present in a total amount of from 0.5 to 10% by weight, preferably from 1 to 4% by weight, most preferably from 2 to 3 Wt .-%, each based on the total weight of the pen is included.
  • antiperspirant effect of the antiperspirant sticks according to the invention can be further improved by adding a polar oil.
  • Further preferred antiperspirant sticks according to the invention are therefore characterized in that a polar oil which is liquid under normal conditions and is selected from is contained
  • symmetrical, unsymmetrical or cyclic esters of carbonic acid with C 8 -C 22 -FEK alcohols in particular di-n-octyl carbonate, di-2-ethylhexyl carbonate and di-dodecyl carbonate,
  • esters of linear or branched C 2 -C- ⁇ 0 alkanols Esters of branched saturated or unsaturated fatty alcohols having 2 to 30 carbon atoms with linear or branched saturated or unsaturated fatty acids having 2 to 30 carbon atoms, which may be hydroxylated,
  • esters of dimers of unsaturated C 2 -C 22 -fatty acids with monovalent linear, branched or cyclic C 2 -C 8 -alkanols or with polyvalent linear or branched C 2 -C 6 -alkanols,
  • Particularly preferred polar oils are selected from the addition products of at least 6 ethylene oxide and / or propylene oxide units to monovalent or polyvalent C 3 . 22 -alkanols such as butanol, butanediol, myristyl alcohol and stearyl alcohol, for.
  • PPG-14 butyl ether Ucon Fluid ® AP
  • PPG-9-butyl ether Breox B25 ®
  • PPG-10 butanediol Macol ® 57
  • PPG-15 stearyl ether Arlamol ® E
  • polar oils are selected from the addition products of 1 to 5 propylene oxide units of mono- or polyhydric C 8 - 22 -alkanols such as octanol, decanol, decanediol, lauryl alcohol, myristyl alcohol and stearyl alcohol, eg. PPG-2 myristyl ether and PPG-3 myristyl ether (Witconol APM ®).
  • very preferred polar oils are selected from the C 8 -C 22 fatty alcohol ethers, in particular from di-n-octyl ether, di-2-ethylhexyl ether and di-dodecyl ether.
  • Other very preferred polar oils are selected from the C 8 -C 22 fatty alcohol esters of monohydric or polyhydric C 2 -C 7 hydroxycarboxylic acids, in particular the esters of glycolic acid, lactic acid, malic acid, tartaric acid, citric acid and salicylic acid.
  • esters based on linear Ci 4 / i 5 alkanols eg. B.
  • Ci 2 .Ci 5 -Alkyllactat, and of branched in the 2-position C 12 / i 3 - alkanols are under the trademark Cosmacol ® by Nordmann, Rassmann GmbH & Co, Hamburg, to obtain, in particular the commercial products Cosmacol ® ESI, Cosmacol® ® EMI and Cosmacol® ® EIT.
  • polar oils according to the invention are selected from branched saturated or unsaturated fatty alcohols having 6 to 30 carbon atoms. These alcohols are also often referred to as Guerbet alcohols, as they are obtainable by the Guerbet reaction.
  • Preferred alcohol oils are Hexyldecanol (Eutanol ® G 16, Guerbitol ® T 16) Octyldodecanol (Eutanol ® G, Guerbitol ® 20), 2-ethylhexyl alcohol and the commercial products Guerbitol ® 18, Isofol ® 12, Isofol ® 16, Isofol ® 24, Isofol ® 36, Isocarb 12 ®, ® Isocarb 16 or Isocarb ® 24th
  • preferred polar oils are mixtures of Guerbet alcohols and Guerbet alcohol esters, for example the commercial product Cetiol ® PGL (hexyldecanol and hexyldecyl laurate).
  • Further inventively preferred polar oils are selected from the symmetrical, asymmetrical or cyclic esters of carbonic acid with fatty alcohols, eg. As glycerol carbonate, dicaprylyl (Cetiol ® CC) or the esters of DE 197 56 454 A1.
  • suitable polar oils are selected from the triglycerides of linear or branched, saturated or unsaturated, optionally hydroxylated C 8 - acids o-3 fat.
  • Particularly suitable may be the use of natural oils, for example soybean oil, cottonseed oil, sunflower oil, palm oil, palm kernel oil, linseed oil, almond oil, castor oil, corn oil, olive oil, rapeseed oil, sesame oil, thistle oil, wheat germ oil, peach kernel oil and the liquid portions of coconut oil and the like.
  • natural oils for example soybean oil, cottonseed oil, sunflower oil, palm oil, palm kernel oil, linseed oil, almond oil, castor oil, corn oil, olive oil, rapeseed oil, sesame oil, thistle oil, wheat germ oil, peach kernel oil and the liquid portions of coconut oil and the like.
  • synthetic triglyceride oils in particular Capric / Caprylic triglycerides, z.
  • Myritol ® 318 Myritol ® 331 (Cognis) or Miglyol ® 812 (Hüls) with unbranched fatty acid residues and glyceryl triisostearin
  • Estol ® GTEH 3609 Uniqema
  • Myritol ® GTEH Cognis
  • polar oils suitable according to the invention are selected from the dicarboxylic acid esters of linear or branched C 2 -C 10 -alkanols, in particular diisopropyl adipate, di-n-butyl adipate, di (2-ethylhexyl) adipate, dioctyl adipate, diethyl / di-n-butyl / Dioctyl sebacate, diisopropyl sebacate, dioctyl malate, dioctyl maleate, dicaprylyl maleate, diisooctyl succinate, di-2-ethylhexyl succinate and di- (2-hexydep ectyl) -succinate.
  • polar oils which are suitable according to the invention are selected from the esters of linear or branched saturated or unsaturated fatty alcohols having 2 to 30 carbon atoms with linear or branched saturated or unsaturated fatty acids having 2 to 30 carbon atoms which may be hydroxylated.
  • these include, hexyldecyl stearate (Eutanol ® G 16 S), hexyldecyl laurate, isodecyl neopentanoate, isononyl isononanoate, 2-ethylhexyl palmitate (Cegesoft ® C 24) and 2-ethyl hexyl stearate (Cetiol ® 868).
  • polar oils suitable according to the invention are selected from the esters of dimers of unsaturated C 12 -C 22 -fatty acids (dinner fatty acids) with monovalent linear, branched or cyclic C 2 -C 18 -alkanols or with polyvalent linear or branched C 2 -C 6 -alkanols , It may be preferred according to the invention to use mixtures of the aforementioned oils.
  • Particularly preferred antiperspirant sticks according to the invention are characterized in that at least one polar oil, in particular at least one of the above-listed polar oils, in a total amount of 2-25% by weight, preferably 5-20% by weight, more preferably 7, 5 to 15% by weight and most preferably 10 to 12% by weight, based on the total weight of the antiperspirant stick.
  • antiperspirant sticks preferred according to the invention may also contain at least one phenyl-substituted polydimethylsiloxane, in particular phenyl trimethicone.
  • Phenyl-substituted polydimethylsiloxanes are preferably present in amounts of from 0.1 to 3% by weight and further promote the residue behavior and the application properties. You can also further optimize antiperspirant performance.
  • antiperspirant sticks according to the invention are characterized in that at least one deodorant active substance is present, which is preferably selected from
  • Arylsulfatase inhibitors ⁇ -glucuronidase inhibitors, aminoacylase inhibitors,
  • Trialkylcitric acid esters in particular triethyl citrate,
  • Zinc compounds in particular zinc phenolsulfonate and zinc ricinoleate
  • Organohalogen compounds in particular triclosan, chlorhexidine, chlorhexidine gluconate and benzalkonium halides, quaternary ammonium compounds, in particular cetylpyridinium chloride,
  • Odor absorbers in particular silicates and zeolites
  • Lantibiotics and mixtures of the aforementioned substances, and / or the antiperspirant active ingredient is selected from the water-soluble astringent inorganic and organic salts of aluminum, zirconium and zinc or any mixtures of these salts.
  • Further preferred antiperspirant sticks according to the invention are characterized in that deodorant active ingredient in a total amount of 0.1-10% by weight, preferably 0.2-7% by weight, particularly preferably 0.3-5% by weight and very preferably 0.4-1.0% by weight, based on from 0.1-10% by weight, in each case based on the total weight of the active substance in the inventive to the total composition according to the invention.
  • stick compositions of the invention may contain conventional excipients and cosmetic and / or dermatological agents.
  • inert, finely divided, inorganic or organic fillers are inert, finely divided, inorganic or organic fillers.
  • inert fillers may be e.g. Silicic acids, clays, talc, veegum or organic fillers, e.g. Polymer powder, starch or cellulose powder.
  • the antiperspirant stick compositions according to the invention preferably additionally comprise 1-20% by weight of a finely divided filler selected from talc, silicic acid and mixtures thereof.
  • Further preferred antiperspirant sticks according to the invention are characterized in that further at least one solid, water-insoluble particulate filler is contained.
  • Particularly preferred solid, water-insoluble particulate fillers are selected from optionally modified starches and starch derivatives which are optionally pregelatinized, cellulose and cellulose derivatives, silica, silicas, spherical polyalkylsesquioxane particles, silica gels, talc, kaolin, clays, e.g. As bentonites, magnesium aluminum silicates, boron nitride, lactoglobulin derivatives, glass powder, polymer powders and mixtures of the aforementioned substances.
  • compositions are characterized in that the at least one solid, water-insoluble, particulate filler is contained in a total amount of 0.01 to 20% by weight, preferably 5 to 15% by weight, based on the total composition ,
  • auxiliaries customary in deodorant and antiperspirant compositions are fragrances, antioxidants, complexing agents, antimicrobial substances and odor-absorbing polymers.
  • dyes and colored or white pigments can be added to increase the attractiveness of the sticks and at least one hair growth inhibiting substance.
  • a further subject matter of the present application is a cosmetic, non-therapeutic method for reducing body odor, which is characterized in that an antiperspirant stick composition as described above, in particular an antiperspirant stick composition according to the embodiments 16, and in particular An antiperspirant stick composition according to any one of claims 1 to 19, to which skin, in particular the skin of the armpits, is applied.
  • Another object of the present application is the non-therapeutic use of an antiperspirant stick composition as described above, in particular an antiperspirant stick composition according to the embodiments 1-16, and in particular an antiperspirant stick composition according to any one of claims 1-19, to Reduction of body odor.
  • Examples 1 to 6 according to the invention are extremely preferred antiperspirant sticks with good abrasion, excellent residue behavior, very good antiperspirant effect and good strength.
  • Examples 7-16 are antiperspirant sticks according to the invention with good abrasion, good residue behavior, very good antiperspirant effect and satisfactory strength. All quantities are based on% by weight. The quantities for the antiperspirant active ingredient are based on wt .-% (USP).

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Abstract

L'invention concerne des sticks antitranspirants sans traces, anhydres, ayant des propriétés améliorées.
EP07857357A 2006-12-29 2007-12-11 Stick antitranspirant sans traces Ceased EP2099529A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102006062567 2006-12-29
DE102007059678A DE102007059678A1 (de) 2006-12-29 2007-12-10 Rückstandsarmer Antitranspirant-Stift
PCT/EP2007/063652 WO2008080772A2 (fr) 2006-12-29 2007-12-11 Stick antitranspirant sans traces

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EP2099529A2 true EP2099529A2 (fr) 2009-09-16

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US (1) US20090304617A1 (fr)
EP (1) EP2099529A2 (fr)
AU (1) AU2007341400A1 (fr)
CA (1) CA2674129A1 (fr)
DE (1) DE102007059678A1 (fr)
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WO (1) WO2008080772A2 (fr)

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DE102008052747A1 (de) * 2008-10-22 2010-04-29 Beiersdorf Ag Antitranspirantstift ohne flüchtige Trägeröle
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EP2637632B1 (fr) 2010-11-12 2018-12-05 Unilever PLC Compositions antiperspirantes contenant une triéthylhexanoïne
DE102011002863A1 (de) 2011-01-19 2012-07-19 Henkel Ag & Co. Kgaa Antitranspirant-Stifte mit verbesserter Langzeitstabilität
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WO2008080772A2 (fr) 2008-07-10
RU2009128873A (ru) 2011-02-10
US20090304617A1 (en) 2009-12-10
CA2674129A1 (fr) 2008-07-10
AU2007341400A1 (en) 2008-07-10
DE102007059678A1 (de) 2008-07-03
WO2008080772A3 (fr) 2009-06-25

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