CA2869325A1 - Polythioether sealants - Google Patents
Polythioether sealants Download PDFInfo
- Publication number
- CA2869325A1 CA2869325A1 CA2869325A CA2869325A CA2869325A1 CA 2869325 A1 CA2869325 A1 CA 2869325A1 CA 2869325 A CA2869325 A CA 2869325A CA 2869325 A CA2869325 A CA 2869325A CA 2869325 A1 CA2869325 A1 CA 2869325A1
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- composition
- curable
- monomer
- polythioether polymer
- 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.)
- Abandoned
Links
- 229920006295 polythiol Polymers 0.000 title claims abstract description 53
- 239000000565 sealant Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 89
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 229920000642 polymer Polymers 0.000 claims abstract description 26
- 230000005855 radiation Effects 0.000 claims abstract description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 10
- 150000004662 dithiols Chemical class 0.000 claims abstract description 7
- 150000001993 dienes Chemical class 0.000 claims abstract description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 5
- 150000003573 thiols Chemical class 0.000 claims abstract description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 18
- 239000000945 filler Substances 0.000 claims description 10
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 9
- 239000002105 nanoparticle Substances 0.000 claims description 8
- 239000000446 fuel Substances 0.000 claims description 7
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- 230000004584 weight gain Effects 0.000 claims description 4
- 235000019786 weight gain Nutrition 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 5
- 239000003999 initiator Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 1
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 241000579895 Chlorostilbon Species 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CUDSBWGCGSUXDB-UHFFFAOYSA-N Dibutyl disulfide Chemical group CCCCSSCCCC CUDSBWGCGSUXDB-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229920001079 Thiokol (polymer) Polymers 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229910052876 emerald Inorganic materials 0.000 description 1
- 239000010976 emerald Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229910002011 hydrophilic fumed silica Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
-
- 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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
- C08K2003/265—Calcium, strontium or barium carbonate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261619178P | 2012-04-02 | 2012-04-02 | |
| US61/619,178 | 2012-04-02 | ||
| US201361779393P | 2013-03-13 | 2013-03-13 | |
| US61/779,393 | 2013-03-13 | ||
| PCT/US2013/034623 WO2013151893A2 (en) | 2012-04-02 | 2013-03-29 | Polythioether sealants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2869325A1 true CA2869325A1 (en) | 2013-10-10 |
Family
ID=48096324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2869325A Abandoned CA2869325A1 (en) | 2012-04-02 | 2013-03-29 | Polythioether sealants |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20150065600A1 (enExample) |
| EP (1) | EP2834287B1 (enExample) |
| JP (1) | JP6189930B2 (enExample) |
| KR (1) | KR20140146145A (enExample) |
| CN (1) | CN104812806A (enExample) |
| CA (1) | CA2869325A1 (enExample) |
| WO (1) | WO2013151893A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016516848A (ja) * | 2013-03-13 | 2016-06-09 | スリーエム イノベイティブ プロパティズ カンパニー | ポリチオエーテル系シーラント |
| CA2935343A1 (en) | 2013-12-30 | 2015-07-09 | 3M Innovative Properties Company | Compositions including a polythiol, an unsaturated compound, and a dye and methods relating to such compositions |
| CN105874015B (zh) | 2013-12-30 | 2019-01-18 | 3M创新有限公司 | 染料、由其制备的填料、包括填料的组合物以及确定此类组合物的固化度的方法 |
| JP7016698B2 (ja) | 2014-12-23 | 2022-02-07 | スリーエム イノベイティブ プロパティズ カンパニー | ２系統硬化のポリチオエーテル |
| EP3256541B1 (de) * | 2015-02-13 | 2022-11-16 | Chemetall GmbH | Verfahren zum auftragen einer schwefel-haltigen dichtmasse, vorrichtung hierzu, und seine verwendung |
| BR112017023446A2 (pt) | 2015-04-29 | 2018-07-31 | 3M Innovative Properties Co | método para a fabricação de uma rede polimérica a partir de um politiol e um poliepóxido |
| CA2991039A1 (en) | 2015-06-29 | 2017-01-05 | 3M Innovative Properties Company | Compositions including a polythiol, an unsaturated compound, and a dye and methods relating to such compositions |
| JP2019521223A (ja) * | 2016-06-30 | 2019-07-25 | スリーエム イノベイティブ プロパティズ カンパニー | ポリチオール、不飽和化合物、光開始剤、及び有機ハイドロパーオキサイドを含む、二元硬化性チオール−エン組成物、並びにそれから調製した航空宇宙産業における使用のための架橋ポリマーシーラント |
| EP3535332A1 (en) | 2016-11-03 | 2019-09-11 | 3M Innovative Properties Company | Method of applying a sealant to an aircraft component |
| WO2018085190A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Polythiol sealant compositions |
| WO2018085534A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Compositions including a photolatent amine, camphorquinone, and a coumarin and related methods |
| US10591950B2 (en) | 2017-04-19 | 2020-03-17 | United States Of America As Represented By The Secretary Of The Army | Copolymerized bis-(ethylene oxy) methane polysulfide polymer and hydroxyl terminated poly butadiene as a solid fueled ramjet fuel |
| CN107312174B (zh) * | 2017-07-19 | 2019-10-18 | 北京化工大学 | 一种聚硫醚的合成方法 |
| PH12020500618B1 (en) * | 2018-01-30 | 2024-02-21 | Namics Corp | Resin composition and cured material of same, adhesive, semiconductor device, and electronic component |
| CN112262014A (zh) | 2018-06-15 | 2021-01-22 | 3M创新有限公司 | 组件和制备垫片的方法 |
| US20220258848A1 (en) | 2019-07-25 | 2022-08-18 | 3M Innovative Properties Company | Methods of shimming an assembly |
| CN110903479A (zh) * | 2019-12-02 | 2020-03-24 | 锦西化工研究院有限公司 | 一种用作聚硫密封剂增塑剂的硫醚聚合物的制备方法 |
| CN111944392B (zh) * | 2020-08-25 | 2021-08-24 | 江南大学 | 一种超支化聚硫醚/环氧丙烯酸酯树脂复合光固化涂料及其制备方法和应用 |
| CN114031775B (zh) * | 2021-09-27 | 2023-07-07 | 武汉纺织大学 | 绿色无溶剂生物基抗菌胶粘剂及其制备方法 |
| CN115678011B (zh) * | 2022-11-11 | 2024-09-10 | 赛感科技(深圳)有限公司 | 聚硫醚弹性体及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1215421A (zh) * | 1996-04-05 | 1999-04-28 | 美国3M公司 | 可见光可聚合的组合物 |
| US6509418B1 (en) * | 1997-02-19 | 2003-01-21 | Prc-Desoto International, Inc. | Sealants and potting formulations including mercapto-terminated polymers produced by the reaction of a polythiol and polyvinyl ether monomer |
| US5912319A (en) * | 1997-02-19 | 1999-06-15 | Courtaulds Aerospace, Inc. | Compositions and method for producing fuel resistant liquid polythioether polymers with good low temperature flexibility |
| DE69815662T2 (de) * | 1997-02-19 | 2004-04-08 | PRC-DeSoto International, Inc., Burbank | Zusammensetzung und verfahren zur herstellung von flüssiger, treibstoffbeständiger polymere mit hoher biegsamkeit bei tiefer temperatur |
| JP5102424B2 (ja) * | 2000-06-30 | 2012-12-19 | ピーアールシー−デソト インターナショナル，インコーポレイティド | ポリチオールとポリビニルエーテルモノマーとの反応によって調製されるメルカプト末端ポリマーを含むシーラント及び注封配合物 |
| SE522479C2 (sv) * | 2002-01-16 | 2004-02-10 | Ericsson Telefon Ab L M | Sammansatt effektförstärkare |
| US20100210745A1 (en) * | 2002-09-09 | 2010-08-19 | Reactive Surfaces, Ltd. | Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes |
| US7097883B2 (en) * | 2003-06-05 | 2006-08-29 | Ppg Industries Ohio, Inc. | Low temperature liquid polythioether polymers |
| US7390859B2 (en) * | 2005-02-08 | 2008-06-24 | Ppg Industries Ohio, Inc. | Compositions and methods of making compositions exhibiting fuel resistance |
| US20110319559A1 (en) * | 2010-06-25 | 2011-12-29 | PRC-DeSolo International, Inc. | Polythioether polymers, methods for preparation thereof, and compositions comprising them |
| US8729198B2 (en) * | 2010-08-13 | 2014-05-20 | Prc Desoto International, Inc. | Compositions comprising thiol-terminated polymers and sulfur-containing ethylenically unsaturated silanes and related cured sealants |
| US8932685B2 (en) * | 2010-08-13 | 2015-01-13 | Prc-Desoto International, Inc. | Methods for making cured sealants by actinic radiation and related compositions |
-
2013
- 2013-03-29 EP EP13716668.2A patent/EP2834287B1/en not_active Not-in-force
- 2013-03-29 JP JP2015504641A patent/JP6189930B2/ja not_active Expired - Fee Related
- 2013-03-29 WO PCT/US2013/034623 patent/WO2013151893A2/en not_active Ceased
- 2013-03-29 CN CN201380018818.XA patent/CN104812806A/zh active Pending
- 2013-03-29 KR KR1020147030228A patent/KR20140146145A/ko not_active Ceased
- 2013-03-29 CA CA2869325A patent/CA2869325A1/en not_active Abandoned
- 2013-03-29 US US14/389,905 patent/US20150065600A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2834287A2 (en) | 2015-02-11 |
| WO2013151893A2 (en) | 2013-10-10 |
| KR20140146145A (ko) | 2014-12-24 |
| CN104812806A (zh) | 2015-07-29 |
| JP2015517012A (ja) | 2015-06-18 |
| US20150065600A1 (en) | 2015-03-05 |
| WO2013151893A3 (en) | 2014-02-20 |
| JP6189930B2 (ja) | 2017-08-30 |
| EP2834287B1 (en) | 2021-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180323 |
|
| FZDE | Discontinued |
Effective date: 20201002 |