EP2493601A2 - Encapsulation de constituants réactifs pour systèmes unitaires par utilisation de buses coaxiales - Google Patents

Encapsulation de constituants réactifs pour systèmes unitaires par utilisation de buses coaxiales

Info

Publication number
EP2493601A2
EP2493601A2 EP10751930A EP10751930A EP2493601A2 EP 2493601 A2 EP2493601 A2 EP 2493601A2 EP 10751930 A EP10751930 A EP 10751930A EP 10751930 A EP10751930 A EP 10751930A EP 2493601 A2 EP2493601 A2 EP 2493601A2
Authority
EP
European Patent Office
Prior art keywords
core
shell particles
shell
solvent
particles according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP10751930A
Other languages
German (de)
English (en)
Inventor
Mandy MÜHLBACH
Patrick Stenner
Silke Suhr
Peter Neugebauer
Heike Heeb
Günter Schmitt
Peter Reinhard
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.)
Roehm GmbH Darmstadt
Original Assignee
Evonik Roehm GmbH
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 Evonik Roehm GmbH filed Critical Evonik Roehm GmbH
Publication of EP2493601A2 publication Critical patent/EP2493601A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/04—Making microcapsules or microballoons by physical processes, e.g. drying, spraying
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K40/00—Shaping or working-up of animal feeding-stuffs
    • A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • 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
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4833—Encapsulating processes; Filling of capsules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • 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
    • A61K2800/10—General cosmetic use
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4816—Wall or shell material
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2984—Microcapsule with fluid core [includes liposome]

Definitions

  • the present invention encompasses the production of core-shell particles for encapsulation of reactive components for one-component resin systems.
  • the present invention encompasses the encapsulation of
  • the invention comprises a method for 100% encapsulation of the Reakti component, so that the Berel ste11u g novel, storage-stable Harzsyste e is made possible.
  • the core-shell particles are constructed in such a way that they are light, fast and almost easy to apply
  • One-component reactive systems can be used in many ways
  • Coatings such as paints or reactive resins such as e.g. Road markings or industrial floors can be used.
  • the curing mechanism by a subsequent, preferably from the environment
  • Oxygen can be started.
  • Moisture-curing systems but mostly isocyanate or silyl based are not suitable for all applications. For example, for very thick layers or applications in the wet area, moisture-curing systems are less suitable. In addition, such systems cure only very slowly, often only over
  • one-component, storage-stable 1-component systems is the encapsulation of a reaction component such as a crosslinker ,, a catalyst . , an accelerator or an initiator.
  • a reaction component such as a crosslinker , a catalyst . , an accelerator or an initiator.
  • reaction resins usually cure by means of radical reaction mechanisms.
  • the initiator system consists in most cases of a Radik.alkettensta.rter or initiator, usually from a peroxide or a redox system, and a
  • the release time of the reactive component is controllable.
  • core-shell particles whose shell is not permeable to the active ingredient and which must be opened to release the active ingredient.
  • both the core not in the shell and the shell must not be soluble in the medium in which the core-shell particle is located.
  • a pure release mechanisms can either be based on an external energy input or a change in chemical formulation parameters such as
  • Moisture content or pH are based. However, release by water or solvent entry has the disadvantage that such methods either only very slowly
  • Shear energy in the mixing is too high for the relatively unstable sheaths. This effect is usually counteracted by producing particles that produce a
  • Be shell material In addition is. breaking up smaller particles more difficult than the larger one. This can lead to incomplete provision of the reactive component and possibly make an even higher proportion of formulation necessary.
  • Emulsion polymerization of styrene or (meth) acrylates Disadvantage of such a method is that components that have even minor water solubility can only be incompletely encapsulated.
  • Disadvantage may prove to be a relatively broad distribution of grain sizes or agglomeration.
  • organic shell materials for encapsulating reactive components or solutions or dispersions are, above all, naturally derived polymers such as gelatin, carrageenan, gum arabic or xanthan gum, or chemically modified materials based thereon, such as methyl cellulose or gelatin polysulfate.
  • naturally derived polymers such as gelatin, carrageenan, gum arabic or xanthan gum, or chemically modified materials based thereon, such as methyl cellulose or gelatin polysulfate.
  • WO 98 26865 the production of core-shell particles mi
  • the capsules with a Size of a maximum of 100 ⁇ be by treatment of
  • Liquid-j et method in which a liquid jet is placed in a precipitation medium and thereby curing individual particles, listed.
  • Disadvantage of this method according to the prior art is that the individual particles mostly by a tearing of the introduced beam in the
  • Particles are not round and a wide
  • Size distribution may have.
  • Non-round particles however, are more unstable than ideal rounds, so they tend to break prematurely when formulated under shear.
  • a mixture of the component to be encapsulated and the shell material is added in the classical liquid j et method. But this is only possible
  • Phase separation lead By suitable process parameters, the method can be varied in such a way that particles form. If previously a component to be encapsulated was dispersed in the solution, forms around this a colloid shell, which can be cured. In the
  • the polycondensates are polyesters or polyamides. However, such capsules are either too permeable to the core trapped
  • the encapsulation mechanism is one
  • Interfacial polymerizations provide the synthesis
  • biocompatible capsule materials e.g. for dental applications.
  • One example is trays
  • microparticles are described with particularly narrow, monomodal size distributions of a divinylbenzene crosslinked polystyrene.
  • styrene is pre-polymerized by introducing the crosslinker and then together with v / eiteren initiators inside a
  • Droplets are provided with an outer layer by a co-axially drained separating and protective liquid and are thereby size-stabilized.
  • Components in the aqueous phase hardens this outer shell and protects the inner area during the
  • Attributed polymer character of the microparticles is Attributed polymer character of the microparticles.
  • Coaxial nozzle Vierden viewed from the inside out, the liquid phase to be encapsulated, a polymer solution from which the shell is formed, and a liquid, which serves as a carrier stream and may be identical to the collecting liquid, dripped and thereby by an amplifier before dropwise analogous structure torn.
  • the drops are dropped into an aqueous polyvinyl alcohol solution where the shell materials cure.
  • the objective here is the synthesis of biodegradable particles for e.g.
  • the shell consists of degradable polymers such as polylactide-glycolide.
  • the core is with solutions of a medicinal agent and not with a technical reactive substance such as initiators,
  • the particles are very small even under 200 yra.
  • a method that does not have the disadvantages of a colloidal system and at the same time hardens quite quickly without a polymerization step.
  • a disadvantage for industrial applications such as e.g. the
  • Biodegradation is targeted to a very slow drug release, a.usge. At xndustrie1.1en
  • the object of the present invention is the development of a method for providing reactive components containing the core-shell particles for 1 -Com onente - coating system - hereinafter referred to briefly as 1 -K system.
  • the task is to provide core-shell particles that can be quickly opened by the simplest possible mechanism.
  • the core-shell particles should be activated in such a way that the reactive component contained in the core is almost completely released in the shortest possible time
  • a further object is to provide a process for the production of core-shell particles which is simple to carry out and can be used to produce particles having an adjustable diameter that is larger than the prior art and ideally a monomodal size distribution.
  • a coaxial nozzle (Fig.l) is a liquid jet consisting of two or three
  • the innermost (2a) of the two or three layers of the liquid jet is a reactive component which is present either as a pure substance or preferably as a stable solution or dispersion.
  • the outermost layer (4a) is one
  • This third layer is optional. e. ) By a device from the beam in free fall ro fen (consisting of 2a + 3a) is formed.
  • the droplet break is supported by a frequency generator and an amplifier
  • the solvent (6) into which the drops fall contains an additional component which prevents or slows down the sedimentation of the resulting particles.
  • the object has been achieved such that the inorganic material is the aqueous solution of a silicate (3), preferably of sodium silicate.
  • water glass on solidification by physical curing in a suitable solvent.
  • the said solvent is notable for being readily miscible with water, as well as having a hygroscopic character, and at the same time being a non-solvent for the silicate dissolved in the aqueous part of the droplet, so that this immediately after being dropped into the solvent ( 6) the
  • the preferred solvents (6) are polar ones Alcohols such as methanol, ethanol or n- or iso-propanol; Ketones such as acetone; and
  • the solvent is preferably an alcohol, more preferably ethanol.
  • the solvent hereinafter referred to as collecting liquid (6) into which the drops fall, contains a
  • This component which slows down or prevents sedimentation is a thickener which is miscible with solvent, which is preferably a polar alcohol. Also of great importance is that the miscibility of the
  • the thickener may be, for example carboxyvinyl polymers, such as Tego Carbomer ® 340 FD act. Preference is given to between 0.01% by weight and 3% by weight, more preferably between 1% by weight and. 2 Gewi, the thickener used.
  • liquid jet also from three
  • Layers (2a, 3a and 4a) to be composed The additional outer layer (4a), the carrier stream, would be a solvent medium that co-operates with the carrier
  • Solvent mixture as used as collecting liquid (6) This optional carrier stream (4a) stabilizes the liquid jet and the
  • the form uniformity of the resulting core-shell particles can be influenced by such a carrier flow.
  • a particular aspect compared to the prior art is the mass ratio between the core or its contents and the shell.
  • the trays must have a certain minimum thickness in order for them to be e.g. during the
  • the shell has a thickness between 30 and 1G0Q ⁇ m, preferably between 50 and 500 ⁇ m.
  • the core-shell particles have a particle size diameter of at least 100 ⁇ m, preferably at least 300 ⁇ m, especially
  • the particle size distribution is preferably monomodal.
  • particle size is meant in this document the actual average primary particle size. Since the formation of agglomerates is excluded, the average primary particle size corresponds to the actual particle size. The particle size also corresponds approximately to the diameter of an approximately circular appearing particle. For non-round particles, the mean diameter is calculated as the average of the shortest and longest diameters. Under diameter is in this context a distance of one point at the edge of the
  • the particle size may be the expert z. B. with the help of image analysis or static light scattering determine.
  • the core-shell particles are ideally close to ideal
  • the particles may also be rod-shaped, drop-shaped, disc-shaped or cup-shaped.
  • the surfaces of the particles are generally round, but may also have adhesions.
  • As a measure of the geometry approximation to the spherical shape can serve to specify an aspect ratio in a known manner. This gives way to the maximum occurring Maximum aspect ratio of 50% of the average aspect ratio.
  • the invention is particularly suitable for the production of core-shell particles with a maximum
  • Particles having a maximum aspect ratio of 3 can be, for example, short rod-shaped or also discus-shaped,
  • the particles have a more or less ball-like or granular shape.
  • the particles are after the dripping of the
  • peroxides can be used for example with methyl methacrylate.
  • the primary particles can interact in such a way that bonds form, which can consist of up to 20 or 30 primary particles. As a rule, they can be partially separated again into primary particles by slight mechanical treatment, without the shells being opened. These bonds are not aggregates in the classical
  • the core-shell particles may be further enhanced by powdering, e.g. It can also be treated with Aeros.il (Evonik Degussa)
  • Aeros.il Evonik Degussa
  • the powder is also used as a desiccant
  • methods of applying the powder such as the application of the powder material in the solvent during curing, an additional washing step with a powder containing dispersion, for example in ethanol or MA, or a pollination of the dry particles, for example in a
  • the core of the core Scha.le ⁇ Part.ikel contains an active ingredient, preferably a liquid solution or dispersion of a
  • Reactive component and more preferably a dispersion of a peroxide in a Eq.
  • Drakesol 260 AT, Polyoel 130 and Degaroute W3, particularly preferably Dagaroute W3 from Evonik Rö m GmbH can be used. To ensure, that The oil contains no more water, this can before the
  • desired effect causes may be as different substances such as dyes, pigments, effect pigments or thickeners in paint or
  • Coating applications act. It may also be vitamins, flavorings, dietary supplements, trace minerals or other food or pet food additives that would not be stable under normal storage conditions. It may continue around
  • cosmetic applications e.g. in creams, toothpaste, hair care products, soaps or lotions can be used.
  • it may also be medicinal agents in controlled release medicaments.
  • Reactive component contained in the core-shell particles according to the invention to initiators, accelerators or
  • Catalysts particularly preferably initiators
  • the reactive component is an initiator, it is preferably one
  • Radical initiator more preferably an organic peroxide.
  • organic peroxide examples are, without the
  • the accelerators may be, for example, amines, preferably aromatically substituted tertiary amines.
  • amines preferably aromatically substituted tertiary amines.
  • examples again without limitation, are N, N-dimethyl-p-toluidine, N, N-bis (2-hydroxyethyl) -p-toluidine or N, N-bis- (2-hydroxypropyl) -p-toluidine,
  • This mechanical energy may be applied to a hard surface or whirl, for example, in the form of one, two, or three times applied pressure, shear, puncture, squeezing, rubbing, spraying. By introducing this energy, the core-shell particle is broken up and the active ingredient is released.
  • the shape of the mechanical energy input is freely selectable and is not suitable to limit the invention in any way. Alternatively, the
  • Core-shell particles of the invention are also opened by the addition of a suitable solvent, in particular by the addition of water.
  • a suitable solvent in particular by the addition of water.
  • conventional radiation, thermal energy is not suitable for opening the core-shell particles
  • core-shell particles according to the invention can be used in a wide variety of applications, without the following examples in any form
  • the core-shell particles filled with an initiator, catalyst or accelerator are in
  • Reaction resin mixtures e.g. for road marking, laying of floors, bridge construction or Rapid
  • Prototyping used can also be used in sealants, chemical dowels, adhesives or other coatings.
  • Reactive materials - such as monomers - filled core-shell particles can be used in self-healing materials.
  • Particles filled with active ingredients can be used, for example, in cosmetics, medicine or animal nutrition. Designations from the drawing Fig.1
  • Measuring body Plate (solvent trap) / cone, DC 60/2 ° filling
  • Sample vessel 5.9 mL sodium silicate solution
  • Gear pump for initiator oil suspension 1 - 2 1 / h
  • Viscosity of 110 mPas is in one
  • BPO 75 benzoyl peroxide, hereinafter BPO
  • BPO 75 benzoyl peroxide
  • Ultraturrax (alternatively ultrasound) treated. 1 minute each on level one, 10 minutes on level two and finally 3 minutes on level three.
  • the sodium silicate solution (3) and the initiator suspension (2) from BPO and Degaroute W3 are added to the appropriate storage containers.
  • the frequency generator (1) and the light source (5) are switched on at a frequency of 16kHz.
  • the pumps for the Sodium silicate solution (3b) and the suspension (2b) switched on in a timely manner and regulated a continuous flow.
  • a collecting vessel (9) is a 600mL beaker with a
  • the dropping height between nozzle head and collecting medium is 16 cm.At the beginning of the batching, one waits until a trumpet has formed by stirring.After every two to three minutes, when the solution is saturated, the beaker is replaced by another containing fresh catchment medium,
  • the particle-containing collecting solutions are ' combined and filtered off the particles through a sieve with a pore size less than 500 ym. Subsequently, the particles are first with technical ethanol and then with
  • Washed methyl methacrylate Between the individual
  • the diameters were determined microscopically using a Bi 1dana 1yse

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Food Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Zoology (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Catalysts (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Dental Preparations (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

La présente invention concerne la préparation de particules coeur-enveloppe pour encapsuler des constituants réactifs pour des systèmes de résine unitaires. L'invention fait intervenir notamment l'encapsulation d'initiateurs radicalaires tels que des peroxydes. L'invention a également pour objet un procédé pour encapsuler à 100% les constituants réactifs pour permettre la mise à disposition de nouveaux systèmes de résine stables au stockage. Dans le même temps, les particules coeur-enveloppe sont produites de sorte qu'au cours de l'application elles peuvent être ouvertes facilement, rapidement et approximativement en intégralité, alors qu'avant application elles présentent une stabilité au stockage et au cisaillement suffisantes.
EP10751930A 2009-10-30 2010-09-07 Encapsulation de constituants réactifs pour systèmes unitaires par utilisation de buses coaxiales Withdrawn EP2493601A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009046244A DE102009046244A1 (de) 2009-10-30 2009-10-30 Verkapselung von Reaktivkomponenten für 1-K-Systeme unter Verwendung von Koaxialdüsen
PCT/EP2010/063068 WO2011051033A2 (fr) 2009-10-30 2010-09-07 Encapsulation de constituants réactifs pour systèmes unitaires par utilisation de buses coaxiales

Publications (1)

Publication Number Publication Date
EP2493601A2 true EP2493601A2 (fr) 2012-09-05

Family

ID=43806958

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10751930A Withdrawn EP2493601A2 (fr) 2009-10-30 2010-09-07 Encapsulation de constituants réactifs pour systèmes unitaires par utilisation de buses coaxiales

Country Status (10)

Country Link
US (1) US20120171492A1 (fr)
EP (1) EP2493601A2 (fr)
JP (1) JP2013509287A (fr)
CN (1) CN102711977A (fr)
AU (1) AU2010311801A1 (fr)
BR (1) BR112012010165A2 (fr)
CA (1) CA2778910A1 (fr)
DE (1) DE102009046244A1 (fr)
RU (1) RU2012122004A (fr)
WO (1) WO2011051033A2 (fr)

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WO2018216888A1 (fr) * 2017-05-21 2018-11-29 엘지전자 주식회사 Appareil de préparation de composition fluide
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JP2013509287A (ja) 2013-03-14
AU2010311801A1 (en) 2012-03-08
WO2011051033A3 (fr) 2012-06-28
RU2012122004A (ru) 2013-12-10
WO2011051033A2 (fr) 2011-05-05
DE102009046244A1 (de) 2011-05-19
CA2778910A1 (fr) 2011-05-05
US20120171492A1 (en) 2012-07-05
CN102711977A (zh) 2012-10-03
BR112012010165A2 (pt) 2016-04-12

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