ES2673860T3 - Procedimiento para la preparación de espumas rígidas de poliuretano y espumas rígidas de poliisocianurato - Google Patents
Procedimiento para la preparación de espumas rígidas de poliuretano y espumas rígidas de poliisocianurato Download PDFInfo
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- ES2673860T3 ES2673860T3 ES15702428.2T ES15702428T ES2673860T3 ES 2673860 T3 ES2673860 T3 ES 2673860T3 ES 15702428 T ES15702428 T ES 15702428T ES 2673860 T3 ES2673860 T3 ES 2673860T3
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- polyol
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- acid
- polyester polyol
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- 238000002360 preparation method Methods 0.000 title claims description 44
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 41
- 229920000582 polyisocyanurate Polymers 0.000 title claims description 41
- 239000011495 polyisocyanurate Substances 0.000 title claims description 40
- 239000011496 polyurethane foam Substances 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 39
- 150000003077 polyols Chemical class 0.000 claims abstract description 135
- 229920005862 polyol Polymers 0.000 claims abstract description 127
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 98
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 62
- -1 polyethylene terephthalate Polymers 0.000 claims abstract description 62
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 52
- 229920000570 polyether Polymers 0.000 claims abstract description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 23
- 239000000194 fatty acid Substances 0.000 claims abstract description 23
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- 238000005886 esterification reaction Methods 0.000 claims abstract description 22
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 21
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 20
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- 239000003999 initiator Substances 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
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- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 9
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 30
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- 229920001228 polyisocyanate Polymers 0.000 claims description 30
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 26
- 125000005442 diisocyanate group Chemical group 0.000 claims description 22
- 239000012948 isocyanate Substances 0.000 claims description 22
- 239000012757 flame retardant agent Substances 0.000 claims description 21
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- 229920000728 polyester Polymers 0.000 claims description 17
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 15
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
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- GTRSAMFYSUBAGN-UHFFFAOYSA-N tris(2-chloropropyl) phosphate Chemical compound CC(Cl)COP(=O)(OCC(C)Cl)OCC(C)Cl GTRSAMFYSUBAGN-UHFFFAOYSA-N 0.000 claims description 10
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 9
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 9
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 9
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 6
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 claims description 6
- 238000007046 ethoxylation reaction Methods 0.000 claims description 6
- 235000021313 oleic acid Nutrition 0.000 claims description 6
- 239000003549 soybean oil Substances 0.000 claims description 6
- 235000012424 soybean oil Nutrition 0.000 claims description 6
- 239000003760 tallow Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 abstract description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 55
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 38
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
- 239000004814 polyurethane Substances 0.000 description 18
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- 229910052757 nitrogen Inorganic materials 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 13
- 239000003063 flame retardant Substances 0.000 description 12
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 11
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 229960002887 deanol Drugs 0.000 description 11
- 239000012972 dimethylethanolamine Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 150000002460 imidazoles Chemical class 0.000 description 5
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 5
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- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 4
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- 229920000877 Melamine resin Polymers 0.000 description 4
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 4
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- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/141—Hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- 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
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L2666/66—Substances characterised by their function in the composition
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Landscapes
- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
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- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyesters Or Polycarbonates (AREA)
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| EP14154645 | 2014-02-11 | ||
| EP14154645 | 2014-02-11 | ||
| PCT/EP2015/051569 WO2015121057A1 (de) | 2014-02-11 | 2015-01-27 | Verfahren zur herstellung von polyurethan-hartschäumen und polyisocyanurat-hartschäumen |
Publications (1)
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| ES2673860T3 true ES2673860T3 (es) | 2018-06-26 |
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| CA3091147C (en) | 2018-02-16 | 2022-03-08 | H.B. Fuller Company | Electric cell potting compound and method of making |
| JP7323106B2 (ja) * | 2018-04-10 | 2023-08-08 | ステパン カンパニー | 改善された低温r値を有するポリオールブレンド及び硬質フォーム |
| CA3109540A1 (en) * | 2018-08-16 | 2020-02-20 | Basf Se | Environmentally friendly driven polyurethane spray foam systems |
| WO2020089439A1 (en) * | 2018-11-02 | 2020-05-07 | Covestro Deutschland Ag | A rigid polyurethane precast panel |
| CN111138618A (zh) * | 2018-11-02 | 2020-05-12 | 科思创德国股份有限公司 | 聚氨酯硬质预制板 |
| CN114213797A (zh) * | 2022-01-11 | 2022-03-22 | 陈小云 | 一种耐磨防刮smc模塑料及其制备方法 |
| CN119013337A (zh) | 2022-04-04 | 2024-11-22 | 巴斯夫欧洲公司 | 用于从聚氨酯硬质泡沫回收基于亚磷酸酯的阻燃剂的价值链返回方法 |
| EP4612224A1 (en) | 2022-11-03 | 2025-09-10 | Basf Se | Value chain return process for the recovery of not bonded additives by extraction from polyurethane or polyisocyanurate rigid foams and depolymerization of the polyurethane rigid foams |
| CN120153019A (zh) | 2022-11-03 | 2025-06-13 | 巴斯夫欧洲公司 | 用于从废聚氨酯和聚异氰脲酸酯硬质泡沫的解聚中回收聚合亚甲基亚苯基胺(pMDA)作为其HCl盐的价值链返回方法 |
| WO2025016860A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Process for recycling polyurethane foams |
| WO2025016927A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Method for selecting, from a foam mix comprising one or more foam pieces, target foam pieces, method and pre-processing arrangement for pre-processing a foam mix for feeding a reactor of a recycling process and respective computer program |
| WO2025016900A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Process for recycling polyurethane waste through remonomerization by hydro ammonolysis |
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| EP4491364A1 (en) | 2023-07-14 | 2025-01-15 | Basf Se | Method and pre-processing arrangement for pre-processing a foam mix for feeding a reactor |
| WO2025016903A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Recovery of polyesterols from polyesterol-based polyurethanes via hydrolysis and re-condensation |
| WO2025016861A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Method and pre-processing arrangement for pre-processing a foam mix for feeding a reactor of a recycling process for recovering raw materials and respective computer program |
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| DE1003714B (de) | 1956-01-25 | 1957-03-07 | Glanzstoff Ag | Verfahren zum Abbau von Polyaethylenterephthalat zu Terephthalsaeuredimethylester |
| US4529744A (en) * | 1982-10-25 | 1985-07-16 | Stepan Company | Compatibilized aromatic polyester polyols |
| US5051528A (en) | 1990-04-24 | 1991-09-24 | Eastman Kodak Company | Recovery process for ethylene glycol and dimethylterephthalate |
| US6461536B2 (en) * | 1998-02-09 | 2002-10-08 | Basf Corporation | Stable polyester polyol composition |
| WO2006100756A1 (ja) * | 2005-03-22 | 2006-09-28 | Kawasaki Kasei Chemicals Ltd. | ポリエステルポリオールの製造方法 |
| CA2629090C (en) * | 2005-11-14 | 2014-05-27 | Dow Global Technologies Inc. | Method of molding rigid polyurethane foams with enhanced thermal conductivity |
| SI2340269T1 (sl) | 2008-10-15 | 2013-01-31 | Basf Se | Poliesterski polioli na bazi terefthalične kisline |
| CA2819569C (en) * | 2010-12-02 | 2020-01-14 | Basf Se | Polyester polyols based on aromatic dicarboxylic acids |
| US20120214891A1 (en) * | 2011-02-23 | 2012-08-23 | Basf Se | Polyester polyols based on aromatic dicarboxylic acids |
| HUE025196T2 (en) * | 2011-03-22 | 2016-02-29 | Basf Se | PU rigid foam with low heat and good thermal stability |
| CA2862774C (en) * | 2012-01-02 | 2020-08-18 | Basf Se | Producing rigid polyurethane foams and rigid polyisocyanurate foams |
| US20130251975A1 (en) * | 2012-03-23 | 2013-09-26 | Basf Se | Producing rigid polyurethane foams and rigid polyisocyanurate foams |
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| CA2938060A1 (en) | 2015-08-20 |
| KR20160119838A (ko) | 2016-10-14 |
| MX367477B (es) | 2019-08-23 |
| EP3105274A1 (de) | 2016-12-21 |
| US10259906B2 (en) | 2019-04-16 |
| PL3105274T3 (pl) | 2018-08-31 |
| RU2016136382A3 (enExample) | 2018-07-25 |
| WO2015121057A1 (de) | 2015-08-20 |
| JP2017509738A (ja) | 2017-04-06 |
| US20160347904A1 (en) | 2016-12-01 |
| MX2016009946A (es) | 2016-11-11 |
| BR112016017431A8 (pt) | 2020-06-16 |
| RU2016136382A (ru) | 2018-03-15 |
| KR102338624B1 (ko) | 2021-12-14 |
| CN105980438A (zh) | 2016-09-28 |
| EP3105274B1 (de) | 2018-03-14 |
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