KR101903956B1 - 질소-함유 헤테로시클릭 에폭시 경화제, 조성물 및 방법 - Google Patents
질소-함유 헤테로시클릭 에폭시 경화제, 조성물 및 방법 Download PDFInfo
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- KR101903956B1 KR101903956B1 KR1020160152184A KR20160152184A KR101903956B1 KR 101903956 B1 KR101903956 B1 KR 101903956B1 KR 1020160152184 A KR1020160152184 A KR 1020160152184A KR 20160152184 A KR20160152184 A KR 20160152184A KR 101903956 B1 KR101903956 B1 KR 101903956B1
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- Prior art keywords
- amine
- epoxy
- curing agent
- group
- amines
- Prior art date
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 191
- 239000004593 Epoxy Substances 0.000 title claims abstract description 153
- 239000000203 mixture Substances 0.000 title claims abstract description 146
- 238000000034 method Methods 0.000 title claims abstract description 52
- -1 polyethylene Polymers 0.000 claims abstract description 133
- 229920000768 polyamine Polymers 0.000 claims abstract description 63
- 239000004698 Polyethylene Substances 0.000 claims abstract description 61
- 229920000573 polyethylene Polymers 0.000 claims abstract description 61
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 54
- 239000003822 epoxy resin Substances 0.000 claims abstract description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 46
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 46
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 43
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 39
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 152
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 93
- 150000001412 amines Chemical class 0.000 claims description 90
- 239000000047 product Substances 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000007795 chemical reaction product Substances 0.000 claims description 43
- 230000008569 process Effects 0.000 claims description 34
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims description 30
- 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 claims description 24
- 150000004982 aromatic amines Chemical class 0.000 claims description 21
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 19
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 15
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 9
- 229920002866 paraformaldehyde Polymers 0.000 claims description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 8
- 229920003986 novolac Polymers 0.000 claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 6
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 5
- 150000001923 cyclic compounds Chemical class 0.000 abstract description 2
- 238000001723 curing Methods 0.000 description 203
- 238000000576 coating method Methods 0.000 description 62
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- 239000011248 coating agent Substances 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 238000012360 testing method Methods 0.000 description 29
- 239000007788 liquid Substances 0.000 description 25
- 229920005989 resin Polymers 0.000 description 23
- 239000011347 resin Substances 0.000 description 23
- 238000009472 formulation Methods 0.000 description 22
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 21
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 21
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 20
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- 230000015572 biosynthetic process Effects 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002131 composite material Substances 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- HUVYLRHAZAEUHY-UHFFFAOYSA-N 2-(4,5-dihydroimidazol-1-yl)ethanamine Chemical compound NCCN1CCN=C1 HUVYLRHAZAEUHY-UHFFFAOYSA-N 0.000 description 13
- 239000004952 Polyamide Substances 0.000 description 13
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 13
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- 239000000758 substrate Substances 0.000 description 13
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 12
- 239000008199 coating composition Substances 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 11
- 239000000853 adhesive Substances 0.000 description 10
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- 125000001931 aliphatic group Chemical group 0.000 description 10
- 239000004848 polyfunctional curative Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229940106691 bisphenol a Drugs 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
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- 238000011161 development Methods 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
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- 150000004665 fatty acids Chemical class 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 235000019445 benzyl alcohol Nutrition 0.000 description 7
- 238000010276 construction Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 239000000565 sealant Substances 0.000 description 7
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 7
- 238000004383 yellowing Methods 0.000 description 7
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 150000002118 epoxides Chemical group 0.000 description 6
- 238000009408 flooring Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 0 *C(N(*)CC1)N1I Chemical compound *C(N(*)CC1)N1I 0.000 description 5
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000004497 NIR spectroscopy Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
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- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
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- 230000003068 static effect Effects 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
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- 125000003700 epoxy group Chemical group 0.000 description 4
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- 238000004817 gas chromatography Methods 0.000 description 4
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 4
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
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- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 3
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- 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
- C08G59/56—Amines together with other curing agents
- C08G59/60—Amines together with other curing agents with amides
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
-
- 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
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- Phenolic Resins Or Amino Resins (AREA)
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| US62/256,262 | 2015-11-17 | ||
| US15/343,632 US10556985B2 (en) | 2015-11-17 | 2016-11-04 | Nitrogen-containing heterocyclic epoxy curing agents, compositions and methods |
| US15/343,632 | 2016-11-04 |
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| KR20170066220A KR20170066220A (ko) | 2017-06-14 |
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| US10465039B2 (en) | 2015-11-17 | 2019-11-05 | Evonik Degussa Gmbh | Epoxy curing agents, compositions and uses thereof |
| EP3339391B1 (en) * | 2016-12-23 | 2020-02-05 | Evonik Operations GmbH | Apcha as a building block in curing agent formulations for structural adhesives |
| US10450406B2 (en) * | 2017-08-30 | 2019-10-22 | Saudi Arabian Oil Company | Fluorinated polyimide-based epoxy materials |
| JP7242694B2 (ja) | 2018-03-05 | 2023-03-20 | エボニック オペレーションズ ゲーエムベーハー | エポキシ配合物のための脂環式アミン:エポキシ系のための新規な硬化剤 |
| US10696888B2 (en) | 2018-08-30 | 2020-06-30 | Saudi Arabian Oil Company | Lost circulation material compositions and methods of isolating a lost circulation zone of a wellbore |
| US11168243B2 (en) * | 2018-08-30 | 2021-11-09 | Saudi Arabian Oil Company | Cement compositions including epoxy resin systems for preventing fluid migration |
| US11352541B2 (en) | 2018-08-30 | 2022-06-07 | Saudi Arabian Oil Company | Sealing compositions and methods of sealing an annulus of a wellbore |
| EP3798246B1 (en) * | 2019-09-27 | 2024-01-31 | Henkel AG & Co. KGaA | One component (1k) composition based on modified epoxy resin |
| US11891476B2 (en) * | 2019-11-08 | 2024-02-06 | Evonik Operations Gmbh | Phenalkamine epoxy curing agents from methylene bridged poly(cyclohexyl-aromatic) amines and epoxy resin compositions containing the same |
| US11332656B2 (en) | 2019-12-18 | 2022-05-17 | Saudi Arabian Oil Company | LCM composition with controlled viscosity and cure time and methods of treating a lost circulation zone of a wellbore |
| US11370956B2 (en) | 2019-12-18 | 2022-06-28 | Saudi Arabian Oil Company | Epoxy-based LCM compositions with controlled viscosity and methods of treating a lost circulation zone of a wellbore |
| US11193052B2 (en) | 2020-02-25 | 2021-12-07 | Saudi Arabian Oil Company | Sealing compositions and methods of plugging and abandoning of a wellbore |
| US11236263B2 (en) | 2020-02-26 | 2022-02-01 | Saudi Arabian Oil Company | Method of sand consolidation in petroleum reservoirs |
| CN115803358A (zh) * | 2020-07-10 | 2023-03-14 | 赢创运营有限公司 | 环氧-胺加合物 |
| US12173113B2 (en) | 2021-03-17 | 2024-12-24 | Evonik Operations Gmbh | Waterborne epoxy curing agent |
| WO2023010442A1 (en) | 2021-08-05 | 2023-02-09 | Evonik Operations Gmbh | Amine composition, epoxy system prepared from the amine composition and an epoxy resin, and use of the epoxy system |
| US11827841B2 (en) | 2021-12-23 | 2023-11-28 | Saudi Arabian Oil Company | Methods of treating lost circulation zones |
| CN117327433B (zh) * | 2023-09-28 | 2025-05-06 | 江苏进华重防腐涂料有限公司 | 建筑物排水用铸铁管和铸铁配件的环氧漆及其制备和应用 |
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| CN107099021A (zh) | 2017-08-29 |
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| JP2017095703A (ja) | 2017-06-01 |
| KR20170066220A (ko) | 2017-06-14 |
| EP3170849B1 (en) | 2019-08-28 |
| US10556985B2 (en) | 2020-02-11 |
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