CA2833131A1 - Biologically degradable polymeric composition with high deformability - Google Patents
Biologically degradable polymeric composition with high deformability Download PDFInfo
- Publication number
- CA2833131A1 CA2833131A1 CA2833131A CA2833131A CA2833131A1 CA 2833131 A1 CA2833131 A1 CA 2833131A1 CA 2833131 A CA2833131 A CA 2833131A CA 2833131 A CA2833131 A CA 2833131A CA 2833131 A1 CA2833131 A1 CA 2833131A1
- Authority
- CA
- Canada
- Prior art keywords
- parts
- blends
- composition
- properties
- phb
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 109
- 229920000747 poly(lactic acid) Polymers 0.000 claims abstract description 39
- 239000004626 polylactic acid Substances 0.000 claims abstract description 38
- 239000004014 plasticizer Substances 0.000 claims abstract description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229920001577 copolymer Polymers 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 239000000654 additive Substances 0.000 claims abstract description 8
- 230000000996 additive effect Effects 0.000 claims abstract description 8
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920000903 polyhydroxyalkanoate Polymers 0.000 claims abstract description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 239000003921 oil Substances 0.000 claims abstract description 3
- 229920002959 polymer blend Polymers 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 abstract description 4
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 abstract description 3
- 229920000331 Polyhydroxybutyrate Polymers 0.000 description 40
- 239000005015 poly(hydroxybutyrate) Substances 0.000 description 40
- 238000000034 method Methods 0.000 description 27
- 229920000642 polymer Polymers 0.000 description 19
- 238000012545 processing Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 229920005692 JONCRYL® Polymers 0.000 description 8
- 238000004806 packaging method and process Methods 0.000 description 7
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000006872 improvement Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 208000034530 PLAA-associated neurodevelopmental disease Diseases 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 3
- 239000001069 triethyl citrate Substances 0.000 description 3
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 3
- 235000013769 triethyl citrate Nutrition 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 208000037534 Progressive hemifacial atrophy Diseases 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- -1 compatibilizer Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002667 nucleating agent Substances 0.000 description 2
- 238000012017 passive hemagglutination assay Methods 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 239000010499 rapseed oil Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000003017 thermal stabilizer Substances 0.000 description 2
- 229960002622 triacetin Drugs 0.000 description 2
- AXKZIDYFAMKWSA-UHFFFAOYSA-N 1,6-dioxacyclododecane-7,12-dione Chemical compound O=C1CCCCC(=O)OCCCCO1 AXKZIDYFAMKWSA-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229920000704 biodegradable plastic Polymers 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229920006237 degradable polymer Polymers 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/16—Compositions of unspecified macromolecular compounds the macromolecular compounds being biodegradable
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Biological Depolymerization Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SK26-2011A SK262011A3 (sk) | 2011-04-11 | 2011-04-11 | Biologically degradable polymeric composition having improved properties |
| SKPP26-2011 | 2011-04-11 | ||
| PCT/SK2012/000004 WO2012141660A1 (en) | 2011-04-11 | 2012-04-11 | Biologically degradable polymeric composition with high deformability |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2833131A1 true CA2833131A1 (en) | 2012-10-18 |
Family
ID=46052855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2833131A Abandoned CA2833131A1 (en) | 2011-04-11 | 2012-04-11 | Biologically degradable polymeric composition with high deformability |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20140039096A1 (enExample) |
| EP (1) | EP2710076B1 (enExample) |
| JP (1) | JP5830163B2 (enExample) |
| KR (1) | KR101651319B1 (enExample) |
| CN (1) | CN103459498B (enExample) |
| CA (1) | CA2833131A1 (enExample) |
| RU (1) | RU2605592C2 (enExample) |
| SG (1) | SG194040A1 (enExample) |
| SK (1) | SK262011A3 (enExample) |
| WO (1) | WO2012141660A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015141753A1 (ja) * | 2014-03-17 | 2015-09-24 | 帝人株式会社 | 易分解性樹脂組成物 |
| JP2015227400A (ja) * | 2014-05-30 | 2015-12-17 | 帝人株式会社 | 粉体の製造方法 |
| CN105440617A (zh) * | 2015-12-23 | 2016-03-30 | 江苏道勤新材料科技有限公司 | 一种环保塑料材料 |
| CN105504727B (zh) * | 2016-02-03 | 2018-05-18 | 黑龙江鑫达企业集团有限公司 | 一种高韧性全降解聚乳酸基复合材料及其制备方法 |
| SK289234B6 (sk) * | 2017-09-13 | 2024-08-14 | Panara, A.S. | Biodegradovateľná polymérna zmes a spôsob jej prípravy |
| CN108587092B (zh) * | 2018-05-02 | 2020-09-04 | 张家港绿洲新材料科技有限公司 | 生物基可降解的聚羟基羧酸合金材料及其制备方法和应用 |
| FR3083544B1 (fr) | 2018-07-06 | 2020-09-11 | Carbiolice | Matiere plastique à haute teneur en pla comprenant des oligomeres d’acide lactique |
| FR3083543B1 (fr) | 2018-07-06 | 2021-03-05 | Carbiolice | Matiere plastique à haute teneur en pla comprenant un ester de citrate |
| CN117050486A (zh) * | 2022-05-07 | 2023-11-14 | 深圳市裕同包装科技股份有限公司 | 用于制造阻隔层的组合物、阻隔层及其制造方法和包装材料 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9001A (en) * | 1852-06-08 | Keflector-lamp | ||
| US622316A (en) | 1899-04-04 | Display-rack | ||
| US3021A (en) * | 1843-03-30 | Stove with elevated ovejst | ||
| US10008A (en) * | 1853-09-13 | India-rtjbbee | ||
| EP0052459B1 (en) | 1980-11-18 | 1985-12-04 | Imperial Chemical Industries Plc | Beta-hydroxybutyrate polymers |
| GB9311399D0 (en) * | 1993-06-02 | 1993-07-21 | Zeneca Ltd | Polyester composition |
| US5883199A (en) * | 1997-04-03 | 1999-03-16 | University Of Massachusetts | Polyactic acid-based blends |
| RU2225705C2 (ru) * | 2001-11-08 | 2004-03-20 | Чухаджян Ара Гарникович | Адгезивная пленка для фиксации съемных протезов |
| US6869985B2 (en) * | 2002-05-10 | 2005-03-22 | Awi Licensing Company | Environmentally friendly polylactide-based composite formulations |
| US7098292B2 (en) * | 2003-05-08 | 2006-08-29 | The Procter & Gamble Company | Molded or extruded articles comprising polyhydroxyalkanoate copolymer and an environmentally degradable thermoplastic polymer |
| US7368503B2 (en) * | 2003-12-22 | 2008-05-06 | Eastman Chemical Company | Compatibilized blends of biodegradable polymers with improved rheology |
| ES2397898T3 (es) | 2004-06-23 | 2013-03-12 | Natureworks Llc | Polímeros de ácido láctico ramificados y métodos para preparar los mismos |
| CN101098932B (zh) * | 2005-01-12 | 2011-08-17 | 巴斯福股份公司 | 可生物降解聚酯混合物 |
| WO2007022080A2 (en) | 2005-08-12 | 2007-02-22 | Michigan State University | Biodegradable polymeric nanocomposite compositions particularly for packaging |
| BRPI0600783A (pt) | 2006-02-24 | 2007-11-20 | Phb Ind Sa | composição polimérica biodegradável e método para produção de uma composição polimérica biodegradável |
| BRPI0600683A (pt) * | 2006-02-24 | 2007-11-20 | Phb Ind Sa | composição polimérica ambientalmente degradável e seu processo de obtenção |
| BRPI0600787A (pt) | 2006-02-24 | 2007-11-20 | Phb Ind Sa | composição polimérica ambientalmente degradável e seu método de obtenção |
| JP5388410B2 (ja) * | 2006-06-08 | 2014-01-15 | 大阪瓦斯株式会社 | 耐熱性を向上させた植物由来プラスチック材料及び成形体 |
| CN101205356A (zh) * | 2006-12-22 | 2008-06-25 | 深圳市奥贝尔科技有限公司 | 聚羟基烷酸酯及其共聚物与聚乳酸的共混改性 |
| NL1033719C2 (nl) * | 2007-04-19 | 2008-10-21 | Synbra Tech Bv | Deeltjesvormig expandeerbaar polymelkzuur, werkwijze voor het vervaardigen hiervan, geschuimd vormdeel op basis van deeltjesvormig expandeerbaar polymelkzuur evenals werkwijze voor het vervaardigen hiervan. |
| TW201022328A (en) | 2008-06-25 | 2010-06-16 | Metabolix Inc | Branched PHA compositions, methods for their production, and use in applications |
| JP5556010B2 (ja) * | 2008-12-16 | 2014-07-23 | 株式会社リコー | 熱可塑性樹脂の成形方法及び成形品 |
| US20100330382A1 (en) | 2009-06-26 | 2010-12-30 | Toray Plastics (America), Inc. | Biaxially oriented polylactic acid film with improved moisture barrier |
| CN102906193B (zh) * | 2010-05-17 | 2015-07-01 | 梅塔玻利克斯公司 | 含有聚羟基烷酸酯的增韧聚乳酸 |
| CN101875763A (zh) * | 2010-06-22 | 2010-11-03 | 中国科学院长春应用化学研究所 | 一种高韧性聚乳酸树脂及其制备方法 |
-
2011
- 2011-04-11 SK SK26-2011A patent/SK262011A3/sk unknown
-
2012
- 2012-04-11 CA CA2833131A patent/CA2833131A1/en not_active Abandoned
- 2012-04-11 US US14/111,536 patent/US20140039096A1/en not_active Abandoned
- 2012-04-11 JP JP2014505108A patent/JP5830163B2/ja active Active
- 2012-04-11 SG SG2013073648A patent/SG194040A1/en unknown
- 2012-04-11 WO PCT/SK2012/000004 patent/WO2012141660A1/en not_active Ceased
- 2012-04-11 EP EP12720304.0A patent/EP2710076B1/en active Active
- 2012-04-11 KR KR1020137027069A patent/KR101651319B1/ko active Active
- 2012-04-11 RU RU2013149900/05A patent/RU2605592C2/ru active
- 2012-04-11 CN CN201280017779.7A patent/CN103459498B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2710076B1 (en) | 2018-06-06 |
| EP2710076A1 (en) | 2014-03-26 |
| SK262011A3 (sk) | 2012-11-05 |
| JP2014510826A (ja) | 2014-05-01 |
| KR101651319B1 (ko) | 2016-08-25 |
| RU2013149900A (ru) | 2015-05-20 |
| SG194040A1 (en) | 2013-11-29 |
| CN103459498A (zh) | 2013-12-18 |
| US20140039096A1 (en) | 2014-02-06 |
| RU2605592C2 (ru) | 2016-12-20 |
| JP5830163B2 (ja) | 2015-12-09 |
| CN103459498B (zh) | 2017-03-01 |
| WO2012141660A1 (en) | 2012-10-18 |
| KR20140047598A (ko) | 2014-04-22 |
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| Date | Code | Title | Description |
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Effective date: 20180411 |