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)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (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 (https=) |
| EP (1) | EP2834287B1 (https=) |
| JP (1) | JP6189930B2 (https=) |
| KR (1) | KR20140146145A (https=) |
| CN (1) | CN104812806A (https=) |
| CA (1) | CA2869325A1 (https=) |
| WO (1) | WO2013151893A2 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150131076A (ko) * | 2013-03-13 | 2015-11-24 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 폴리티오에테르 실란트 |
| 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 |
| BR112017013742A2 (pt) | 2014-12-23 | 2018-03-13 | 3M Innovative Properties Co | politioéter de cura dupla |
| BR112017017216B1 (pt) * | 2015-02-13 | 2022-09-27 | Chemetall Gmbh | Método para vedação, revestimento ou/e nivelamento aerodinâmico de pelo menos um elemento de conexão, aparelho automático, e, uso do método inventivo ou/e do aparelho inventivo |
| US10526440B2 (en) | 2015-04-29 | 2020-01-07 | 3M Innovative Properties Company | Method of making a polymer network from a polythiol and a polyepoxide |
| 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 |
| WO2018005416A1 (en) * | 2016-06-30 | 2018-01-04 | 3M Innovative Properties Company | Dual curable thiol-ene composition, comprising a polythiol, an unsaturated compound, a photoinitiator and an organic hydroperoxide, as well as a cross-linked polymer sealant prepared therefrom for use in aerospace |
| CA3042860A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Polythiol sealant compositions |
| WO2018085546A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Composition including a polythiol, a polyepoxide, a photolatent base, and an amine and methods relating to the composition |
| US11198757B2 (en) | 2016-11-03 | 2021-12-14 | 3M Innovative Properties Company | Compositions including a photolatent amine, camphorquinone, and 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 |
| US20200347227A1 (en) * | 2018-01-30 | 2020-11-05 | Namics Corporation | Resin composition and cured material of same, adhesive, semiconductor device, and electronic component |
| US20210252830A1 (en) | 2018-06-15 | 2021-08-19 | 3M Innovative Properties Company | Assemblies and methods of making a shim |
| 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 |
|---|---|---|---|---|
| BR9708589A (pt) * | 1996-04-05 | 1999-08-03 | Minnesota Mining & Mfg | Composição polimerizável por luz visível e processos para revestir um substrato com um revestimento protetor e para reparar um defeito em um substrato revestido |
| 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 |
| 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 |
| DK0961804T3 (da) * | 1997-02-19 | 2003-10-06 | Prc Desoto Int Inc | Sammensætning og fremgangsmåde til fremstilling af brændstofbestandige flydende polythioetherpolymerer med god fleksibilitet ved lav temperatur |
| AU2001276841A1 (en) * | 2000-06-30 | 2002-01-14 | Prc-Desoto International, Inc. | Sealants and potting formulations including mercapto-terminated polymers produced by the reaction of polythiol and polyvinyl ether monomer |
| 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 |
| US8932685B2 (en) * | 2010-08-13 | 2015-01-13 | Prc-Desoto International, Inc. | Methods for making cured sealants by actinic radiation and related compositions |
| 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 |
-
2013
- 2013-03-29 WO PCT/US2013/034623 patent/WO2013151893A2/en not_active Ceased
- 2013-03-29 KR KR1020147030228A patent/KR20140146145A/ko not_active Ceased
- 2013-03-29 US US14/389,905 patent/US20150065600A1/en not_active Abandoned
- 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 CN CN201380018818.XA patent/CN104812806A/zh active Pending
- 2013-03-29 CA CA2869325A patent/CA2869325A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR20140146145A (ko) | 2014-12-24 |
| WO2013151893A3 (en) | 2014-02-20 |
| US20150065600A1 (en) | 2015-03-05 |
| EP2834287A2 (en) | 2015-02-11 |
| JP6189930B2 (ja) | 2017-08-30 |
| EP2834287B1 (en) | 2021-09-08 |
| JP2015517012A (ja) | 2015-06-18 |
| WO2013151893A2 (en) | 2013-10-10 |
| CN104812806A (zh) | 2015-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180323 |
|
| FZDE | Discontinued |
Effective date: 20201002 |