EP2900718A1 - Prépolymères nco pauvres en monomères et utilisation desdits prépolymères - Google Patents

Prépolymères nco pauvres en monomères et utilisation desdits prépolymères

Info

Publication number
EP2900718A1
EP2900718A1 EP13759205.1A EP13759205A EP2900718A1 EP 2900718 A1 EP2900718 A1 EP 2900718A1 EP 13759205 A EP13759205 A EP 13759205A EP 2900718 A1 EP2900718 A1 EP 2900718A1
Authority
EP
European Patent Office
Prior art keywords
diisocyanate
nco
aliphatic
compounds
formula
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Withdrawn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
EP13759205.1A
Other languages
German (de)
English (en)
Inventor
Emmanouil Spyrou
Holger Loesch
Andrea Diesveld
Andrea THESING
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.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa 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 Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP2900718A1 publication Critical patent/EP2900718A1/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Withdrawn legal-status Critical Current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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8093—Compounds containing active methylene groups
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2895—Compounds containing active methylene groups
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7843—Nitrogen containing -N-C=0 groups containing urethane groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes

Definitions

  • the invention discloses a low-monomer NCO prepolymer composition of the type A-B-A which is obtained by reacting C-H azider compounds with diisocyanates, as well as processes for their preparation and use.
  • Polyisocyanates are preferred in paint, adhesives, and sealants because of their high reactivity and versatility. For toxicological and workplace hygiene reasons, free monomeric diisocyanates are undesirable. Therefore, one strives diisocyanates in NCO-containing prepolymers by reaction with
  • Monomers is low, while high NCO content in the prepolymers and at the same time low viscosity.
  • the object of the invention was therefore the development of prepolymers which do not have the aforementioned disadvantages, and have a high content of NCO groups in the prepolymers and have a very low viscosity at a low content of monomers.
  • reaction products of an excess of diisocyanates and CH-acidic compounds after removal of the excess monomeric diisocyanate, yield precisely those desired low-monomer NCO-containing prepolymers having a high NCO content and low viscosity.
  • R in formula I and formula II are each independently a bifunctional, organofunctional radical which comprises aromatic, aliphatic and (cyclo) aliphatic and / or cycloaliphatic bifunctional radicals,
  • An organofunctional C-H azide compound HBH of the formula III having at least two acidic hydrogen atoms comprises substituted linear aliphatic, (cyclo) -aliphatic or branched aliphatic compounds having 3 to 25 carbon atoms, at an alpha-carbon atom to the C-H acidic carbon atom at least one
  • the electron withdrawing group or substituent comprises at least one electronegative atom as a C atom, accordingly, the electron withdrawing substituent is more electronegative than a carbon atom, with the electron withdrawing group preferably included or selected is made of ester,
  • the (ii) organofunctional C-H azide compound HBH of the formula III having at least two acidic hydrogen atoms on an alpha-carbon atom to the C-H acidic carbon atom comprises at least one
  • electron-withdrawing group preferably assigns them to both alpha-standing
  • Organofunctional C-H azide compounds of the formula III HBH include ⁇ -di-carbonyl compounds and derivatives of ⁇ -di-carbonyl compounds.
  • the reaction is optionally carried out in the presence of a catalyst, the catalyst may remain in the composition so that the composition will contain small amounts of the catalyst
  • Catalyst may contain.
  • formula I can also be represented as A-B-A by reacting
  • Diisocyanates in simplified form are represented as A in which the acidic HBH is present in the urethane groups.
  • diisocyanates of the general formula II it is preferred to use aromatic, aliphatic and (cyclo) aliphatic and / or cycloaliphatic diisocyanates.
  • diisocyanates are z. B. in Houben-Weyl, Methods of Organic Chemistry, Volume 14/2, page 61 ff. And J. Liebigs Annalen der Chemie, Volume 562, pages 75 to 136 described.
  • Preferably used diisocyanates include isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), diisocyanato-dicyclohexylmethane (H12MDI), 2-methylpentane diisocyanate (MPDI), 2,2,4-trimethylhexamethylene diisocyanate / 2,4,4-trimethylhexamethylene diisocyanate (TMDI), norbornane diisocyanate (NBDI) , Diisocyanatomethyl- cyclohexane (HXDI), toluidine diisocyanate (TDI), and / or methylene diphenyl diisocyanate (MDI) as well as tetramethyl
  • Suitable aliphatic diisocyanates advantageously have 3 to 16
  • Carbon atoms, preferably 4 to 12 carbon atoms, in the linear or branched alkylene radical and suitable cycloaliphatic or (cyclo) aliphatic diisocyanates advantageously 4 to 18 carbon atoms in the cycloalkylene radical, preferably 6 to 15 carbon atoms.
  • suitable cycloaliphatic or (cyclo) aliphatic diisocyanates advantageously 4 to 18 carbon atoms in the cycloalkylene radical, preferably 6 to 15 carbon atoms.
  • (cyclo) aliphatic diisocyanates the skilled worker understands at the same time cyclic and aliphatic bound NCO groups.
  • cycloaliphatic diisocyanates are understood to mean those which have only NCO groups bonded directly to the cycloaliphatic ring. Examples are cyclohexane diisocyanate,
  • methyldiphenyl diisocyanate such as diphenylmethane-2,2'-diisocyanate, diphenylmethane-2,4-diisocyanate, diphenylmethane-4,4'-diisocyanate or mixtures comprising the abovementioned MDIs, 2,4- and / or 2, 6-toluene diisocyanate (TDI), 4-methylcyclohexane-1,3-diisocyanate, 2-butyl-2-ethylpentamethylene diisocyanate, 3 (4) -isocyanatomethyl-1-methylcyclohexyl isocyanate, 2-isocyanatopropylcyclohexylisocyanate, 2,4 ' Methyl bis (cyclohexyl) diisocyanate, 1, 4-diisocyanato-4-methylpentane.
  • MDI methyldiphenyl diisocyanate
  • TDI 6-tolu
  • cycloaliphatic diisocyanates Under (cyclo) aliphatic diisocyanates, the skilled worker understands at the same time cyclic and aliphatic bound NCO groups, as z. B. isophorone diisocyanate is the case. In contrast, cycloaliphatic diisocyanates are understood as those which have only directly attached to the cycloaliphatic ring NCO groups, for. Eg H12MDI.
  • C-H acidic organofunctional compounds which can be used according to the invention have at least one of the alpha-terminal carbon of the aliphatic C-H acid hydrogen
  • Compounds of the general formula III HBH are, according to the invention, those compounds which carry a hydrogen atom attached to an aliphatic carbon atom, activation of the corresponding carbon-hydrogen bond being effected by virtue of at least one or more electron-withdrawing groups.
  • the electron-withdrawing group may be groups of any atoms that have an inductive (eg, I-effect) and / or mesomeric (eg, -M-effect) effect on a C [BOND] H acidity of the [alpha] lead-hydrogen.
  • Suitable electronegative substituents are, for example, halogen atoms.
  • Preferred electronegative groups include ester groups, sulfoxide groups, sulfone groups, nitro groups, phosphonate groups,
  • Preferred electron-withdrawing Substituents are nitrile and ester groups, more preferably the carboxylic acid methyl ester and carboxylic acid ethyl ester groups.
  • the abovementioned compounds may according to a preferred embodiment be present as ⁇ -di-functionalized compounds, such as preferably as ⁇ -di-carbonyl, ⁇ -di-ester, ⁇ -di-nitrile, ⁇ -di-nitro, ⁇ -di di-sulfoxide,
  • ⁇ -di-sulfone ⁇ -di-nitro, ⁇ -di-phosphonato, ⁇ -di-isonitrile compounds or as a ⁇ -di-functionalized compound comprising at least two of the abovementioned electronegative groups or electron-withdrawing substituents.
  • Preferred organofunctional CH azide compounds HBH of the formula III having at least two acidic hydrogen atoms include diketones, ketoesters, diesters, nitriles and halogens substituted aliphatic compounds, linear aliphatic, (cyclo) aliphatic or branched aliphatic compounds having 3 to 25 carbon atoms selected from ⁇ -di-carbonyl compounds, diketones, ketoesters, diesters, nitrile esters, dinitriles and also cyclic diketones and derivatives of the abovementioned compounds.
  • the two H in HBH the acidic hydrogens of the C-H aziden compound.
  • Particularly preferred organofunctional CH acid compounds HBH of the formula III having at least two acidic hydrogen atoms are selected from 1,3-cyclohexanedione, dimedone, malonic acid diesters, acetoacetic acid esters, especially the ethyl or methyl esters of acetoacetic acid, acetylacetone and / or a mixture comprising at least two of the mentioned CH acidic compounds.
  • compositions according to the invention have at least preferably greater than or equal to 0.1% by weight of NCO prepolymers according to the invention having two NCO groups in the general formula (I) with respect to the total composition, preferably greater than or equal to 1% by weight and particularly preferably greater than or equal to 5 wt .-% NCO prepolymers with two NCO groups.
  • the compositions may be greater than or equal to 10% by weight, 20% by weight or
  • a content of monomer of less than or equal to 2.0% by weight, preferably less than or equal to 0.7% by weight, relative to the total composition is adjusted. It is particularly preferred that the process according to the invention
  • compositions of prepolymers are obtained whose content of prepolymers having two NCO groups of the general formula (I) is greater than or equal to 10 wt .-%, preferably greater than or equal to 20 wt .-% in the total composition.
  • the reaction of the (i) diisocyanate and the (ii) CH-acidic compound is preferably carried out in a molar ratio of 1: 1: 1 to 100: 1, in particular from 10: 1 to 1: 1, particularly preferably from 5: 1 to 2 : 1, including the limits.
  • the reaction can be carried out at 20 to 200 ° C until the theoretical NCO number corresponding to the molar reaction of two acidic hydrogen atoms of the C-H acidic compound used is achieved with the diisocyanates used. Therefore, the theoretical NCO number results from the molar amount of diisocyanates used, which react in the molar ratio of 2 to 1 with the C-H acid compounds in the ideal case.
  • the theoretical NCO number is on the
  • the cooled composition can be optionally further treated, are separated in the optionally present solvent and the excess of monomeric diisocyanates, in particular until a content of monomer of less than 2.0 wt .-% is present. This is preferably done by gentle distillation, for. B.
  • Short path distillation or thin film distillation preferably at temperatures of 120-220 ° C and pressures of 0.001 mbar to 100 mbar, in particular from 0.001 mbar to 50 mbar.
  • compositions thus obtained comprising the NCO prepolymer have a monomer content of ⁇ 2 wt .-%, preferably ⁇ 1 wt .-% and particularly preferably ⁇ 0.5 Wt .-%.
  • the reaction mixture is preferably cooled and subjected to a short path distillation, in particular with a bottom temperature of 100 to 160 ° C, preferably by 150 ° C with plus / minus 10 ° C and a pressure of 0.1 to 1 mbar, preferably by 0.5 mbar with a fluctuation of plus / minus 0.25 mbar.
  • reaction of diisocyanate and the CH-acidic compound can be carried out in the presence of an inert solvent or without an inert solvent.
  • the reaction of diisocyanate and the CH-acidic compound can be carried out in the presence of an inert solvent or without an inert solvent.
  • the reaction of diisocyanate and the CH-acidic compound can be carried out in the presence of an inert solvent or without an inert solvent.
  • the reaction of diisocyanate and the CH-acidic compound can be carried out in the presence of an inert solvent or without an inert solvent.
  • the diisocyanate and the CH azide compound in a molar ratio of A to B from 1, 1 to 100, preferably 2 to 5, mixed in suitable aggregates and while at a reaction temperature of 20 to 220 ° C, preferably 40 -. 100 ° C until the theoretical NCO number (corresponding to the complete reaction of both CH-acidic hydrogen atoms of HBH of formula III (component B)) is achieved.
  • the main product is an A-B-A adduct.
  • known catalysts can be used, for example organometallic salts. Examples are dibutyltin dilaurate or zinc octoate, or metal-free bases such. For example, triethylamine or diazabicyclooctane.
  • a low monomer content composition of NCO prepolymers of general formula (I) to produce reactive OH and / or NCO urethane prepolymers by reacting the low monomer NCO prepolymers with polyols, wherein the molar ratio of NCO groups to OH groups from 1:10 to 10: 1.
  • Polyols include polyhydric alcohols, monomeric, oligomeric or polymeric polyols.
  • polyhydric alcohols include the monomeric polyols such as the monomeric diols, triols and monomeric compounds having greater than or equal to two HO groups (hydroxy groups).
  • monoalcohols is possible.
  • monomeric diols for example, the following can be used without restricting the polyols thereto: ethylene glycol, triethylene glycol, butanediol-1, 4, pentanediol-1, 5,
  • Other useful monomeric tri- and polyols can be used, for example, without restricting the polyols to them: trimethylolpropane,
  • Preferred polymeric polyols may be selected from the following, other poyls known to those skilled in the art may also be used, such as, for example, polyesters, polycaprolactones, polyethers, polycarbonates or OH-terminated poly (meth) acrylates.
  • the monomer-poor NCO prepolymers of the general formula (I) can be used for the preparation of reactive OH or NCO urethane prepolymers by reaction with polyols in the NCO / OH ratio of preferably 1: 2 to 2: 1. With an NCO excess, an NCO-containing urethane prepolymer is obtained, which can crosslink, for example, by a moisture cure.
  • an OH or NCO urethane prepolymers of the general formula (I) can be used for the preparation of reactive OH or NCO urethane prepolymers by reaction with polyols in the NCO / OH ratio of preferably 1: 2 to 2: 1.
  • an NCO excess an NCO-containing urethane prepolymer is obtained, which can crosslink, for example, by a moisture cure.
  • organometallic salts are dibutyltin dilaurate or zinc octoate.
  • metal-free bases triethylamine or diazabicyclooctane are suitable.
  • Moisture cure is usually at room temperature or at slightly elevated temperatures. It is preferably carried out in a temperature range of 20 to 80 ° C, preferably 80 ° C are not exceeded.
  • the aforementioned catalysts can be used for moisture curing.
  • the reaction of OH groups with CH-azide-blocked NCO groups at 100-180 ° C carried out with elimination of monomeric alcohols. This reaction can also be accelerated by catalysts.
  • amines such. B. 1, 5-diazabicyclo [4.3.0] non-5-ene (DBN) or 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU) used.
  • the subject of the invention is the use of a
  • composition obtained by the process of the composition comprising low-monomer NCO prepolymers together with polyols for the production of lacquer,
  • Adhesives plastics, composites and sealants are Adhesives plastics, composites and sealants.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Sealing Material Composition (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une composition de prépolymère NCO pauvre en monomères de type A-B-A, obtenue en faisant réagir des composés azidiques C-H avec des diisocyanates, ainsi que des procédés pour la préparer et l'utiliser.
EP13759205.1A 2012-09-27 2013-09-09 Prépolymères nco pauvres en monomères et utilisation desdits prépolymères Withdrawn EP2900718A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102012217549.0A DE102012217549A1 (de) 2012-09-27 2012-09-27 Monomerarme NCO-Prepolymere und ihre Verwendung
PCT/EP2013/068541 WO2014048701A1 (fr) 2012-09-27 2013-09-09 Prépolymères nco pauvres en monomères et utilisation desdits prépolymères

Publications (1)

Publication Number Publication Date
EP2900718A1 true EP2900718A1 (fr) 2015-08-05

Family

ID=49118526

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13759205.1A Withdrawn EP2900718A1 (fr) 2012-09-27 2013-09-09 Prépolymères nco pauvres en monomères et utilisation desdits prépolymères

Country Status (6)

Country Link
US (1) US20150266992A1 (fr)
EP (1) EP2900718A1 (fr)
JP (1) JP2015537060A (fr)
CN (1) CN104837881B (fr)
DE (1) DE102012217549A1 (fr)
WO (1) WO2014048701A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3263616B8 (fr) 2016-06-27 2020-01-15 Evonik Operations GmbH Moyens de revêtement fonctionnalisés par un alkoxysilane et contenant un allophanate
EP3401344B1 (fr) 2017-05-09 2020-04-08 Evonik Operations GmbH Procédé de fabrication de trimères et/ou d'oligomères de diisocyanates
EP3556790B1 (fr) 2018-04-16 2021-07-21 Evonik Operations GmbH Agent de réticulation à faible viscosité contenant des groupes alcoxysilane
CN114874129B (zh) * 2022-06-14 2024-06-14 贵州民族大学 一种可低温高效解封的封闭型异氰酸酯的制备方法

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Publication number Priority date Publication date Assignee Title
DE3046409A1 (de) * 1980-12-10 1982-07-15 Bayer Ag, 5090 Leverkusen Beschichtungsmittel und ein verfahren zur herstellung von ueberzuegen
US4439593A (en) * 1983-05-26 1984-03-27 Mobay Chemical Corporation Polyurethane compositions with improved storage stability
DE3734916A1 (de) * 1987-10-15 1989-04-27 Hoechst Ag Haertungskomponente fuer kunstharze, diese enthaltende haertbare mischungen sowie deren verwendung
JP2765024B2 (ja) * 1989-03-28 1998-06-11 大日本インキ化学工業株式会社 イソシアネート・プレポリマーの製造方法
JP4758094B2 (ja) * 2004-11-26 2011-08-24 トーセツ株式会社 給排気管
DE102005048823A1 (de) * 2005-10-10 2007-04-12 Bayer Materialscience Ag Reaktivsysteme, deren Herstellung und Verwendung
EP1772499A3 (fr) * 2005-10-10 2007-09-05 Bayer MaterialScience AG Systèmes réactifs, leur préparation et leur utilisation
US20080071055A1 (en) * 2006-09-14 2008-03-20 Bayer Materialscience Llc New liquid diisocyanates prepared via modification with 1,3-dicarbonyl compounds
JP5150806B2 (ja) * 2007-05-09 2013-02-27 国立大学法人北陸先端科学技術大学院大学 ポリエステル、高分子金属錯体

Non-Patent Citations (2)

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Title
None *
See also references of WO2014048701A1 *

Also Published As

Publication number Publication date
CN104837881B (zh) 2017-03-08
JP2015537060A (ja) 2015-12-24
WO2014048701A1 (fr) 2014-04-03
DE102012217549A1 (de) 2014-03-27
CN104837881A (zh) 2015-08-12
US20150266992A1 (en) 2015-09-24

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