WO2013131776A1 - Amine curable epoxy resin composition - Google Patents

Amine curable epoxy resin composition Download PDF

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Publication number
WO2013131776A1
WO2013131776A1 PCT/EP2013/053762 EP2013053762W WO2013131776A1 WO 2013131776 A1 WO2013131776 A1 WO 2013131776A1 EP 2013053762 W EP2013053762 W EP 2013053762W WO 2013131776 A1 WO2013131776 A1 WO 2013131776A1
Authority
WO
WIPO (PCT)
Prior art keywords
amine
epoxy resin
based composition
amine based
curable epoxy
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
PCT/EP2013/053762
Other languages
English (en)
French (fr)
Inventor
Derek Jingui JIANG
Peter Congxiao WANG
Timothy Marc Handyside
Iris Chunbin ZHAO
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.)
Construction Research and Technology GmbH
Original Assignee
Construction Research and Technology 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 Construction Research and Technology GmbH filed Critical Construction Research and Technology GmbH
Priority to US14/383,189 priority Critical patent/US20150025178A1/en
Priority to AU2013229697A priority patent/AU2013229697B2/en
Priority to EP13707342.5A priority patent/EP2822985B1/en
Priority to CA2866565A priority patent/CA2866565A1/en
Priority to CN201380012616.4A priority patent/CN104159946A/zh
Priority to JP2014560304A priority patent/JP2015511983A/ja
Priority to BR112014019983A priority patent/BR112014019983A8/pt
Priority to RU2014140671A priority patent/RU2014140671A/ru
Publication of WO2013131776A1 publication Critical patent/WO2013131776A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5033—Amines aromatic
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
    • C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
    • C04B41/48—Macromolecular compounds
    • C04B41/4853—Epoxides
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/223—Di-epoxy compounds together with monoepoxy compounds
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/226—Mixtures of di-epoxy compounds
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the invention relates to an amine curable epoxy resin composition.
  • the invention also relates to use of the amine curable epoxy resin composition as primer, topcoat and screeds for application on concrete.
  • Amine curable epoxy resin compositions are used broadly in the floorings and coatings. For the moment, amine curable epoxy resin compositions in the market have longer Return to Service time or shorter pot life at room temperature, which causes them not able to being used easily at room temperature.
  • GB 2 286 592 A disclosed an amine curable epoxy resin composition, wherein the composition with hardener GASMAMINE 328 has compressive strength of 30.5 MPa after application for 24 hours.
  • GASMAMINE 328 has compressive strength of 30.5 MPa after application for 24 hours.
  • an amine curable epoxy resin composition comprising:
  • (A) epoxy resin component comprising:
  • (B) hardener component comprising:
  • the first amine based composition comprises N,N'-bis(3 -amino methylbenzyl)-2 -hydroxytrimethylenediamine represented by the following formula (I) and m-xylylenediamine
  • the second amine based composition comprises the reaction products of m-xylylenediamine and styrene represented by the following formula (II) and m-xylylenediamine
  • A is phenylene, and each of Ri, R 2 and R 3 independently represents hydrogen or phenylethyl;
  • each component content is 100wt%, and each weight percentage is based on the total weight of the amine curable epoxy resin composition.
  • the invention also provides a hardener comprising 20-90 wt% of first amine based composition and 10-80 wt% of second amine based composition, wherein the first amine based composition comprises N,N'-bis(3 -amino methylbenzyl)-2-hydroxytrimethylenediamine represented by the following formula (I) and m-xylylenediamine, and the second amine based composition comprises the reaction products of m-xylylenediamine and styrene represented by the following formula (II) and m-xylylenediamine,
  • each component content is 100wt%, and each weight percentage is based on the total weight of the first amine based composition and the second amine based composition.
  • the invention also provides use of the amine curable epoxy resin composition as primer, topcoat and screeds for application on concrete.
  • the amine curable epoxy resin composition of the present invention has pot life of more than 25 minutes, Return to Service time of less than 12 hours and compressive strength of more than 80 MPa after application for 20 hours at room temperature.
  • the invention provides an amine curable epoxy resin composition comprising:
  • (A) epoxy resin component comprising:
  • (B) hardener component comprising:
  • the first amine based composition comprises N,N'-bis(3 -amino methylbenzyl)-2 -hydroxytrimethylenediamine represented by the following formula (I) and m-xylylenediamine
  • the second amine based composition comprises the reaction products of m-xylylenediamine and styrene represented by the following formula (II) and m-xylylenediamine
  • A is phenylene, and each of Ri , R 2 and R 3 independently represents hydrogen or phenylethyl;
  • each component content is 100wt%, and each weight percentage is based on the total weight of the amine curable epoxy resin composition.
  • the invention provides a hardener comprising 20-90 wt% of first amine based composition and 10-80 wt% of second amine based composition, wherein the first amine based composition comprises N,N'-bis(3 -amino methylbenzyl)-2 -hydroxytrimethylenediamine represented by the following formula (I) and m-xylylenediamine, and the second amine based composition comprises the reaction products of m-xylylenediamine and styrene represented by the following formula (II) and m-xylylenediamine,
  • A is phenylene, and each of Ri , R 2 and R 3 independently represents hydrogen or phenylethyl;
  • N,N'-bis(3 -amino methylbenzyl)-2 -hydroxytrimethylenediamine represented by the formula (I) is a reaction product of m-xylylenediamine and epichlorhydrin, which can be prepared by known process in the art.
  • reaction products of m-xylylenediamine and styrene represented by the formula (II) are prepared according to the process described in CN03149428.5, for example see synthesis example 1.
  • the amine curable epoxy resin composition may further comprise silica sand.
  • the particle size of silica sand is 200 meshes.
  • the content of N,N'-bis(3 -amino methylbenzyl)-2-hydroxytrimethylenediamine is 72-76wt% of the first amine based composition and the content of m-xylylenediamine is 24-28wt% of the first amine based composition in the first amine based composition. More preferably, the content of N,N'-bis(3 -amino methylbenzyl)-2-hydroxytrimethylenediamine is about 75wt% of the first amine based composition and the content of m-xylylenediamine is about 25wt% of the first amine based composition in the first amine based composition.
  • Said first amine based composition is for example GASKAMINE 328 commercially available from Mitsubishi Gas Chemical Company, Inc.
  • the content of m-xylylenediamine is less than lwt% of the second amine based composition in the second amine based composition.
  • Said second amine based composition is for example GASKAMINE 240 commercially available from Mitsubishi Gas Chemical America, Inc.
  • said hardener component may further comprise CeTePox EW99 H which is a formulation based on alkyl polyamines, and CeTePox EW99 H is for example commercially available from CTP Chemicals and Technologies for Polymers GmbH.
  • the hardener component may further comprise benzyl alcohol.
  • the diglycidyl ether of bisphenol A is for example GELR 128 commercially available from Epoxy Base Electronic Material Corporation Limited.
  • the diglycidyl ether of bisphenol F is for example Epikote 862 commercially available from Momentive Specialty Chemicals Inc..
  • monoglycidylether is for example Araldite DY-E commercially available from Huntsman.
  • the alkyl in the alkylsulphonic phenyl ester is C12 to CI 8. More preferably, the alkylsulphonic phenyl ester is dodecylsulphonic phenyl ester.
  • the alkylsulphonic phenyl ester is for example MESAMOIL commercially available from LANXESS.
  • the wetting and dispersing agent is a solution of copolymer with acidic groups, and is for example DISPERBYK-110 commercially available from BYK Additives & Instrument.
  • the defoamer is a defoaming polymer mixture without organic silicon, and is for example BYK 1790 commercially available from BYK Additives & Instrument.
  • the particle size of barium sulfate is preferably 325 meshes.
  • the amine curable epoxy resin composition can be prepared as follows: (A) epoxy resin component is added into mixer at room temperature, such as high speed mixing machine, and mixed until homogeneity. Then, (B) hardener component is added into the above mixture and mixed until homogeneity. Optionally, silica sand can be added into the mixture of (A) epoxy resin component and (B) hardener component and mixed until homogeneity. Said high speed mixing machine is known to those skilled in the art.
  • epoxy resin component and (B) hardener component can be packaged separately, and (A) epoxy resin component and (B) hardener component and optionally silica sand are mixed homogeneously before application.
  • the invention also relates to use of the amine curable epoxy resin composition as primer, topcoat and screeds for application on concrete.
  • the amine curable epoxy resin composition can be applied by processes known to those skilled in the art, for example by using notched trowel, roller and spraying machine etc.
  • Return to Service time used herein represents a time period during which its hardness achieves Shore D 70 after the amine curable epoxy resin composition is applied on concrete with moisture content of 5wt% at room temperature.
  • Pult life used herein is measured according to method 1 of ISO 10364.
  • Compressive strength used herein is measured according to ASTM C 109.
  • WFT wet film thickness
  • Mixture 3 is applied by rolling as primer on concrete with moisture content of 5wt% at the temperature of 23 ⁇ 2°C and relative humidity of 50% , and wet film thickness (WFT) is 0.5 millimeter.
  • Mixture 4 is applied by scraping as topcoat on concrete with moisture content of 5wt% at the temperature of 23 ⁇ 2°C and relative humidity of 50% , and wet film thickness (WFT) is 2.0 millimeters.
  • Mixture 5 is applied by scraping as topcoat on concrete with moisture content of 5wt% at the temperature of 23 ⁇ 2°C and relative humidity of 50% , and wet film thickness (WFT) is 3.0 millimeters.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Ceramic Engineering (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Epoxy Resins (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/EP2013/053762 2012-03-09 2013-02-26 Amine curable epoxy resin composition Ceased WO2013131776A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US14/383,189 US20150025178A1 (en) 2012-03-09 2013-02-26 Amine curable epoxy resin composition
AU2013229697A AU2013229697B2 (en) 2012-03-09 2013-02-26 Amine curable epoxy resin composition
EP13707342.5A EP2822985B1 (en) 2012-03-09 2013-02-26 Amine curable epoxy resin composition
CA2866565A CA2866565A1 (en) 2012-03-09 2013-02-26 Amine curable epoxy resin composition
CN201380012616.4A CN104159946A (zh) 2012-03-09 2013-02-26 可胺固化的环氧树脂组合物
JP2014560304A JP2015511983A (ja) 2012-03-09 2013-02-26 アミン硬化型エポキシ樹脂組成物
BR112014019983A BR112014019983A8 (pt) 2012-03-09 2013-02-26 Composição de resina epoxi curável por amina, endurecedor e uso da composição de resina epoxi curável por amina
RU2014140671A RU2014140671A (ru) 2012-03-09 2013-02-26 Отверждающаяся аминами композиция эпоксидной смолы

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CNPCT/CN2012/072130 2012-03-09
CN2012072130 2012-03-09

Publications (1)

Publication Number Publication Date
WO2013131776A1 true WO2013131776A1 (en) 2013-09-12

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ID=47790189

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/053762 Ceased WO2013131776A1 (en) 2012-03-09 2013-02-26 Amine curable epoxy resin composition

Country Status (8)

Country Link
US (1) US20150025178A1 (https=)
EP (1) EP2822985B1 (https=)
JP (1) JP2015511983A (https=)
AU (1) AU2013229697B2 (https=)
BR (1) BR112014019983A8 (https=)
CA (1) CA2866565A1 (https=)
RU (1) RU2014140671A (https=)
WO (1) WO2013131776A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3805288A4 (en) * 2018-05-24 2021-08-11 Mitsubishi Gas Chemical Company, Inc. HARDENER FOR AQUATIC EPOXY RESIN, AQUATIC EPOXY RESIN COMPOSITION AND HARDENING PRODUCT THEREOF

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JP7177580B2 (ja) * 2016-11-24 2022-11-24 三菱瓦斯化学株式会社 エポキシ樹脂硬化剤、エポキシ樹脂組成物及びその硬化物
EP3546494B1 (en) * 2016-11-24 2021-11-24 Mitsubishi Gas Chemical Company, Inc. Curing agent for water-based epoxy resin, water-based epoxy resin composition, and cured product thereof
JP6829417B2 (ja) * 2017-03-01 2021-02-10 住友大阪セメント株式会社 コンクリート構造物床版補修用プライマー及び当該プライマーを用いたコンクリート構造物床版補修工法
JP7363810B2 (ja) * 2018-11-26 2023-10-18 三菱瓦斯化学株式会社 水系エポキシ樹脂組成物及びその硬化物
DE112019007547T5 (de) * 2019-07-16 2022-03-31 Mitsubishi Electric Corporation Isolierlackzusammensetzung, spule für eine rotierende maschine sowie rotierende maschine

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EP0088623A1 (en) * 1982-03-08 1983-09-14 Mitsubishi Gas Chemical Company, Inc. Polyamine compound of M-xylenediamine and its use as hardening agent
GB2286592A (en) 1994-02-17 1995-08-23 Sandoz Ltd Amine curable epoxy resin compositions
WO1998017724A1 (en) * 1996-10-18 1998-04-30 Henkel Corporation Epoxy curing agent
EP1375554A1 (en) * 2002-06-18 2004-01-02 Mitsubishi Gas Chemical Company, Inc. Amino composition and process for producing the same
WO2005123800A1 (en) * 2004-06-21 2005-12-29 Huntsman Advanced Materials (Switzerland) Gmbh Curing agents for epoxy resins

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3805288A4 (en) * 2018-05-24 2021-08-11 Mitsubishi Gas Chemical Company, Inc. HARDENER FOR AQUATIC EPOXY RESIN, AQUATIC EPOXY RESIN COMPOSITION AND HARDENING PRODUCT THEREOF
US11572436B2 (en) 2018-05-24 2023-02-07 Mitsubishi Gas Chemical Company, Inc. Curing agent for water-based epoxy resin, water-based epoxy resin composition, and cured product thereof

Also Published As

Publication number Publication date
RU2014140671A (ru) 2016-04-27
EP2822985A1 (en) 2015-01-14
AU2013229697A1 (en) 2014-09-25
CA2866565A1 (en) 2013-09-12
JP2015511983A (ja) 2015-04-23
BR112014019983A2 (https=) 2017-06-20
US20150025178A1 (en) 2015-01-22
AU2013229697B2 (en) 2015-12-17
BR112014019983A8 (pt) 2017-07-11
EP2822985B1 (en) 2016-11-30

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