EP2389404A1 - Procédé de fabrication de mousses dures de polyuréthane - Google Patents

Procédé de fabrication de mousses dures de polyuréthane

Info

Publication number
EP2389404A1
EP2389404A1 EP10701121A EP10701121A EP2389404A1 EP 2389404 A1 EP2389404 A1 EP 2389404A1 EP 10701121 A EP10701121 A EP 10701121A EP 10701121 A EP10701121 A EP 10701121A EP 2389404 A1 EP2389404 A1 EP 2389404A1
Authority
EP
European Patent Office
Prior art keywords
polyether alcohol
bii
preparation
toluenediamine
glycerol
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Withdrawn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
EP10701121A
Other languages
German (de)
English (en)
Inventor
Andreas Emge
Marc Fricke
Roman Prochazka
Holger Seifert
Darijo Mijolovic
Achim LÖFFLER
Sirus Zarbakhsh
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP10701121A priority Critical patent/EP2389404A1/fr
Publication of EP2389404A1 publication Critical patent/EP2389404A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/487—Polyethers containing cyclic groups
    • C08G18/4879—Polyethers containing cyclic groups containing aromatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2101/00—Manufacture of cellular products
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0025—Foam properties rigid

Definitions

  • the invention relates to a process for the preparation of polyurethane in the following also abbreviated PU called rigid foams.
  • composite or sandwich elements which are constructed of a rigid polyurethane foam and at least one cover layer of a rigid or elastic material, such as paper, plastic films, aluminum foil, metal sheets, glass fleeces, or chipboard.
  • a rigid or elastic material such as paper, plastic films, aluminum foil, metal sheets, glass fleeces, or chipboard.
  • foaming of cavities in household appliances such as refrigerators, such as refrigerators or chests or hot water storage, with PU rigid foam as a thermal insulation.
  • insulated pipes consisting of a metal or plastic inner ear, a polyurethane insulating layer and an outer sheath made of polyethylene.
  • the insulation of large storage containers or transport ships for example, for storage and transport of liquids or liquefied gases in a temperature range of 160 0 C to -160 0 C is possible.
  • suitable heat and cold PU rigid foams can be known by reacting organic polyisocyanates with one or more compounds having at least two isocyanate-reactive groups, preferably polyester and / or polyether polyols, and usually with the concomitant use of chain extenders and / or crosslinking agents in Presence of blowing agents, catalysts and, optionally, auxiliaries and / or additives are produced.
  • PU rigid foams can be obtained with a low thermal conductivity and good mechanical properties shanks.
  • a constant task in the production of rigid polyurethane foams is the reduction of the thermal conductivity, whereby the mechanical and the processing properties should not be worsened.
  • One way to reduce the thermal conductivity is to increase the content of aromatic moieties in the polyol as described in EP 708127. However, this possibility is limited by the viscosity of the polyol component and the crosslinking of the foam.
  • Polyurethane rigid foams for the production of which polyether alcohols based on toluenediamine (TDA) are used, are gaining in importance recently.
  • TDA toluenediamine
  • polyols have a low viscosity and lead to a reduction in the thermal conductivity of the foams.
  • polyether alcohols having a higher functionality must be used in addition to sufficient crosslinking of the foams.
  • the object of the present invention to provide rigid polyurethane foams using TDA-based polyether alcohols which have a low heat conductivity.
  • the polyol component should have a low viscosity and the flowability of the polyurethane system should be high. Furthermore, the foam should have high crosslinking.
  • the problem could be solved by using in the polyol component a polyether alcohol which was prepared by addition of alkylene oxides to oligomeric glycerol.
  • the invention accordingly provides a process for producing rigid polyurethane foams by reacting
  • component b) contains at least one polyether alcohol bi), prepared by addition of alkylene oxides to toluenediamine, and at least one polyether alcohol bii), prepared by addition of alkylene oxides to H-functional starter substances containing oligomeric glycerol.
  • the oligomeric glycerin is composed of 4-10 glycerol units.
  • the polyether alcohol bii) preferably has a hydroxyl number in the range between 350 and 500 mg KOH / g. its preparation is carried out by the below explained in more detail basic catalysed addition of alkylene oxides, preferably ethylene oxide and / or propylene oxide, particularly preferably pure propylene oxide, to the oligomeric glycerol.
  • alkylene oxides preferably ethylene oxide and / or propylene oxide, particularly preferably pure propylene oxide
  • the starting substance in the preparation of the polyether alcohol bii) contains exclusively oligomeric glycerol.
  • the starting substance in the preparation of the polyether alcohol bii) contains oligomeric glycerol and at least one further H-functional compound.
  • these may be alcohols or amines.
  • alcohols having at least 3 hydroxyl groups are used as further H-functional compound.
  • the starting substance in the preparation of the polyether alcohol bii) comprises oligomeric glycerol and trimethylolpropane. In a further embodiment of the invention, in the preparation of the polyether alcohol bii) the starting substance contains oligomeric glycerol and at least sucrose or sorbitol.
  • the polyether alcohol bii) preferably has a molar ratio of oligomeric glycerol to sucrose or sorbitol of from 2.5: 1 to 1: 2.5.
  • all isomers of the TDA can be used in the preparation of the polyether alcohol bi). It is possible to use a mixture that does not contain o-TDA. Preference is given to mixtures which contain at least 25% by weight, based on the weight of the TDA, of o-TDA, also referred to as vicinal TDA. In a particularly preferred embodiment of the invention, the mixtures of TDA isomers contain at least 95% by weight, based on the weight of the TDA, of vicinal TDA.
  • the preparation of the polyether alcohols is carried out by addition of ethylene oxide, propylene oxide and mixtures thereof to the TDA.
  • the alkylene oxides can be attached individually one after another or in a mixture with each other.
  • ethylene oxide is added first, followed by propylene oxide.
  • the addition of the ethylene oxide takes place preferably without the presence of a catalyst and the addition of the propylene oxide in the presence of a basic catalyst.
  • the polyether alcohol bi) has a hydroxyl number in the range between 120 and 450.
  • the components bi) and bii) are used in a weight ratio of 5: 1 to 1: 2.
  • the component b) may contain further compounds having at least two isocyanate-reactive hydrogen atoms.
  • component b) contains, in addition to components bi) and bii), a polyether alcohol biii) which has been started with at least sucrose.
  • the polyether alcohol biii) has a hydroxyl number in the range between 350 and 550.
  • the polyether alcohols bii) and biii) are used in a weight ratio of 1:10 to 2: 1.
  • Oligomeric glycerol also called polyglycerol
  • Polyglycerin is formed by base-catalyzed reaction with itself.
  • the oligomerization of the glycerol can also be carried out in the presence of other polyfunctional alcohols, for example pentaerythritol or trimethylolpropane.
  • the glycerin is present in a molar excess, since otherwise high-viscosity or solid products are formed.
  • the molar ratio of glycerol to the other alcohol is 5: 1 to 10: 1, especially 9: 1.
  • the alkoxylation of the oligomeric glycerol is preferably carried out in the presence of alkaline catalysts. Particularly preferred are potassium hydroxide or tertiary amines.
  • polyether alcohols which have been prepared by reacting polyglycerol with alkylene oxides is known as an insert component for rigid polyurethane foams.
  • Polyether alcohols started with polyglycerol at the Polyurethanes Technical Conference of 24.-26.9.2007 in Orlando, as well as a rigid polyurethane foam prepared using these polyols
  • the advantages of polyglycerol-initiated polyether alcohols were, in particular, the low viscosity of the polyglycerol and the comparatively high functionality of polyglycerol. onality of polyols called.
  • the polyglycerol-started polyether alcohol was used in combination with a sucrose-initiated polyether alcohol.
  • Suitable organic polyisocyanates a) are all known organic di- and polyisocyanates, preferably aromatic polyfunctional isocyanates.
  • TDI 2,4- and 2,6-toluene diisocyanate
  • MDI 4,4'-, 2,4'- and 2,2'-diphenylmethane diisocyanate
  • MDI 4,4'-, 2,4'- and 2,2'-diphenylmethane diisocyanate
  • the organic di- and polyisocyanates can be used individually or in the form of mixtures.
  • modified polyvalent isocyanates i. Products obtained by chemical reaction of organic di- and / or polyisocyanates used. Examples include uretdione, carbamate, isocyanurate, carbodiimide, allophanate and / or urethane groups-containing di- and / or polyisocyanates.
  • the modified polyisocyanates may optionally be reacted with each other or with unmodified organic polyisocyanates, e.g. 2,4'-, 4,4'-diphenylmethane diisocyanate, crude MDI, 2,4- and / or 2,6-toluene diisocyanate are mixed.
  • reaction products of polyfunctional isocyanates with polyhydric polyols as well as their mixtures with other di- and polyisocyanates can be used.
  • Suitable compounds having at least two isocyanate-reactive hydrogen atoms which are used in addition to the components bi) and bii) are those which contain at least two reactive groups, preferably OH groups, and in particular polyether alcohols and / or polyester alcohols having OH numbers in the range of 25 to 800 mg KOH / g used.
  • the polyester alcohols used are usually obtained by condensation of polyfunctional alcohols, preferably diols, having 2 to 12 carbon atoms, preferably 2 to 6 carbon atoms, with polyfunctional carboxylic acids having 2 to 12 carbon atoms, for example succinic, glutaric, adipic, suberic, azelaic, sebacic, decanedicarboxylic, maleic, fumaric and preferably phthalic, isophthalic, terephthalic and isomeric naphthalenedicarboxylic acids.
  • the polyesterols used usually have a functionality of 1, 5 - 4.
  • polyether polyols which are prepared by known processes, for example by anionic polymerization of alkylene oxides onto H-functional starter substances in the presence of catalysts, preferably alkali metal hydroxides or double metal cyanide catalysts (DMC catalysts), are used.
  • catalysts preferably alkali metal hydroxides or double metal cyanide catalysts (DMC catalysts).
  • alkylene oxides are usually ethylene oxide or propylene oxide, but also tetrahydrofuran, various butylene oxides, styrene oxide, preferably pure 1, 2-
  • the alkylene oxides can be used individually, alternately in succession or as mixtures.
  • Starting substances used are in particular compounds having at least 2, preferably 2 to 8 hydroxyl groups or having at least two primary amino groups in the molecule.
  • starting substances having at least 2 to 8 hydroxyl groups in the molecule are preferably trimethylolpropane, glycerol, pentaerythritol, Zuckerverbin- fertilize such as glucose, sorbitol, mannitol and sucrose, polyhydric
  • Phenols, resoles e.g. oligomeric condensation products of phenol and formaldehyde and Mannich condensates of phenols, formaldehyde and dialkanolamines and melamine used.
  • starting substances with at least two primary amino groups in the molecule are preferably aromatic di- and / or polyamines, for example phenylenediamines, and 4,4'-, 2,4'- and 2,2'-diaminodiphenylmethane and aliphatic di- and polyamines, such as ethylenediamine used.
  • aromatic di- and / or polyamines for example phenylenediamines, and 4,4'-, 2,4'- and 2,2'-diaminodiphenylmethane and aliphatic di- and polyamines, such as ethylenediamine used.
  • the polyether polyols have a functionality of preferably 2 to 8 and hydroxyl numbers of preferably 25 mg KOH / g to 800 mg KOH / g and in particular 150 mg KOH / g to 570 mg KOH / g.
  • the compounds having at least two isocyanate-reactive hydrogen atoms also include the optionally used chain extenders and crosslinkers.
  • chain extenders and crosslinking agents are preferably used alkanolamines and in particular diols and / or triols having molecular weights less than 400, preferably 60 to 300.
  • Chain extenders, crosslinkers or mixtures thereof are suitably used in an amount of 1 to 20 wt .-%, preferably 2 to 5 wt .-%, based on the polyol component.
  • the preparation of rigid foams is usually carried out in the presence of blowing agents, catalysts, flame retardants and cell stabilizers and, if necessary, further auxiliaries and / or additives.
  • chemical blowing agents such as water and / or formic acid can be used, which react with isocyanate groups with elimination of carbon dioxide or carbon dioxide and carbon monoxide.
  • physical blowing agents can also be used in combination with or instead of water. These are compounds which are inert to the starting components and which are usually liquid at room temperature and evaporate under the conditions of the urethane reaction. The boiling point of these compounds is preferably below 50 ° C.
  • the physical blowing agents also include compounds which are gaseous at room temperature and are introduced under pressure into or dissolved in the starting components, for example carbon dioxide, low-boiling alkanes and fluoroalkanes.
  • the blowing agents are usually selected from the group comprising formic acid, alkanes and / or cycloalkanes having at least 4 carbon atoms, dialkyl ethers, esters, ketones, acetals, fluoroalkanes having 1 to 8 carbon atoms, and tetraalkylsilanes having 1 to 3 carbon atoms in the alkyl chain, in particular tetramethylsilane ,
  • Examples include propane, n-butane, iso- and cyclobutane, n-, iso- and cyclopentane, cyclohexane, dimethyl ether, methyl ethyl ether, methyl butyl ether, methyl formate, acetone, as well as fluoroalkanes, which can be degraded in the troposphere and therefore for the Ozone layer are harmless, such as trifluoromethane, difluoromethane, 1, 3,3,3-pentafluoropropene, 1, 1, 1, 3,3-pentafluorobutane, 1, 1, 1, 3,3-pentafluoropropane, 1, 1 , 1, 2-tetrafluoroethane, difluoroethane and heptafluoropropane.
  • the said physical blowing agents can be used alone or in any combination with each other.
  • blowing agent mixture is a mixture of formic acid, water and pentane.
  • the blowing agent component is usually used in an amount of 1 to 45 wt .-%, preferably 1 to 30 wt .-%, particularly preferably 1, 5 to 20 wt .-% and in particular 2 to 15 wt .-%, based on the total weight the components polyol, blowing agent, catalyst system, and possibly foam stabilizers, flame retardants and other additives used.
  • the polyurethane or Polyisocyanuratschaumstoffe usually contain flame retardants.
  • flame retardants Preferably, bromine-free flame retardants are used.
  • flame retardants containing phosphorus atoms in particular trischloroisopropyl phosphate, diethylethane phosphonate, triethyl phosphate and / or diphenyl cresyl phosphate are used.
  • the catalysts used are in particular compounds which greatly accelerate the reaction of the isocyanate groups with the groups reactive with isocyanate groups.
  • Such catalysts are, for example, basic amines, such as secondary aliphatic amines, imidazoles, amidines, alkanolamines, Lewis acids or organometallic compounds, especially those based on tin.
  • Catalyst systems consisting of a mixture of different catalysts can also be used.
  • isocyanurate groups are to be incorporated into the rigid foam, special catalysts are required.
  • the isocyanurate catalysts used are usually metal carboxylates, in particular potassium acetate and its solutions.
  • the catalysts can be used alone or in any desired mixtures, as required.
  • auxiliaries and / or additives are known for this purpose substances, such as surface-active substances, foam stabilizers, cell regulators, fillers, pigments, dyes, antioxidants, hydrolysis, antistatic agents, fungistatic and bacteriostatic agents are used.
  • the polyisocyanates and the compounds having at least two isocyanate-reactive hydrogen atoms are reacted in amounts such that the isocyanate index in the case of the polyurethane foams is in a range between 100 and 220, preferably between 15 and 180, lies.
  • the polyisocyanates a) and component b) are reacted in amounts such that the isocyanate index of the foam is 90 to 350, preferably 100 to 180, more preferably 110 to 140.
  • the rigid polyurethane foams can be prepared batchwise or continuously by known methods, for example on a double belt or in a mold.
  • Polyol 1 polyether alcohol based on vicinal TDA, ethylene oxide and propylene oxide, hydroxyl number: 390 mg KOH / g
  • Polyol 2 polyether alcohol based on sucrose, glycerol and propylene oxide, functionality 5, hydroxyl number: 450 mg KOH / g
  • Polyol 3 polyetheralcohol based on vicinal TDA, ethylene oxide and propylene oxide, hydroxyl number: 160 mg KOH / g
  • Polyol 4 polyether alcohol based on oligomeric glycerol and propylene oxide, functionality 4.5, hydroxyl number: 450 mg KOH / g
  • polyol 5 polyether alcohol based on oligomeric glycerol and propylene oxide, functionality 6.5, hydroxyl number: 450 mg KOH / g
  • Polyol 6 polyether alcohol based on oligomeric glycerol, functionality 6.5, hydroxyl number: 1 100 mg KOH / g
  • polyol 7 polyether alcohol based on sucrose, glycerol, ethylene oxide and propylene oxide, functionality 6.5, hydroxyl number: 450 mg KOH / g
  • Polyol 8 polyetheralcohol based on sucrose, glycerol, oligomeric glycerol and propylene oxide, functionality 6, hydroxyl number: 450 mg KOH / g polyol 9: polyetheralcohol based on vicinal TDA, ethylene oxide and propylene oxide, hydroxyl number: 160 mg KOH / g containing 35% graft particles made of acrylonitrile / stryol (3: 1). Silicone stabilizer: Tegostab® B 8462 Degussa,
  • Catalyst Mixture of 26% N, N-dimethylcyclohexylamine, 53% Lupragen® N301, BASF SE, 21% Lupragen® N600, BASF SE.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention porte sur un procédé de fabrication de mousses dures de polyuréthane par réaction de a) polyisocyanates avec b) des composés comprenant au moins deux atomes d'hydrogène aptes à réagir avec des groupes isocyanate en présence c) d'agents d'expansion, caractérisé par le fait que le constituant b) contient au moins un polyétheralcool bi), produit par addition d'oxydes d'alkylène sur la toluylènediamine, et au moins un polyétheralcool bii) produit par addition d'oxydes d'alkylène sur des substances de départ à fonction H, qui contiennent des oligomères de glycérine.
EP10701121A 2009-01-20 2010-01-12 Procédé de fabrication de mousses dures de polyuréthane Withdrawn EP2389404A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10701121A EP2389404A1 (fr) 2009-01-20 2010-01-12 Procédé de fabrication de mousses dures de polyuréthane

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09150896 2009-01-20
EP10701121A EP2389404A1 (fr) 2009-01-20 2010-01-12 Procédé de fabrication de mousses dures de polyuréthane
PCT/EP2010/050299 WO2010084058A1 (fr) 2009-01-20 2010-01-12 Procédé de fabrication de mousses dures de polyuréthane

Publications (1)

Publication Number Publication Date
EP2389404A1 true EP2389404A1 (fr) 2011-11-30

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP10701121A Withdrawn EP2389404A1 (fr) 2009-01-20 2010-01-12 Procédé de fabrication de mousses dures de polyuréthane

Country Status (6)

Country Link
US (1) US20120022179A1 (fr)
EP (1) EP2389404A1 (fr)
JP (1) JP2012515804A (fr)
KR (1) KR20110117084A (fr)
CN (1) CN102282190A (fr)
WO (1) WO2010084058A1 (fr)

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US20120022179A1 (en) 2012-01-26
WO2010084058A1 (fr) 2010-07-29
JP2012515804A (ja) 2012-07-12
CN102282190A (zh) 2011-12-14
KR20110117084A (ko) 2011-10-26

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