CN107814681A - 用于控制和抑制脂肪族单体聚合的添加剂组合物，及其制备和使用方法 - Google Patents
用于控制和抑制脂肪族单体聚合的添加剂组合物，及其制备和使用方法 Download PDFInfo
- Publication number
- CN107814681A CN107814681A CN201711010294.6A CN201711010294A CN107814681A CN 107814681 A CN107814681 A CN 107814681A CN 201711010294 A CN201711010294 A CN 201711010294A CN 107814681 A CN107814681 A CN 107814681A
- Authority
- CN
- China
- Prior art keywords
- composition
- compositions
- additives
- present
- butadiene
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 195
- 239000000178 monomer Substances 0.000 title claims abstract description 63
- 239000000654 additive Substances 0.000 title claims abstract description 50
- 125000001931 aliphatic group Chemical group 0.000 title claims abstract description 36
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title abstract description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 143
- 238000006471 dimerization reaction Methods 0.000 claims abstract description 39
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000001412 amines Chemical class 0.000 claims abstract description 32
- -1 hydroxy alkyl tertiary amine Chemical class 0.000 claims abstract description 25
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 19
- 241001597008 Nomeidae Species 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 42
- 238000000034 method Methods 0.000 abstract description 22
- 229920000768 polyamine Polymers 0.000 abstract description 20
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract description 18
- 239000007788 liquid Substances 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 12
- 230000008901 benefit Effects 0.000 description 10
- 230000000379 polymerizing effect Effects 0.000 description 8
- 230000001629 suppression Effects 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000003359 percent control normalization Methods 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 2
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- AMLFJZRZIOZGPW-NSCUHMNNSA-N (e)-prop-1-en-1-amine Chemical compound C\C=C\N AMLFJZRZIOZGPW-NSCUHMNNSA-N 0.000 description 1
- HCUWXYBKPSKTAB-UHFFFAOYSA-N 4-benzylidene-2,6-ditert-butylcyclohexa-2,5-dien-1-one Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=CC1=CC=CC=C1 HCUWXYBKPSKTAB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
- C08F2/40—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using retarding agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/22—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing an amide or imide moiety
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Water Supply & Treatment (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1165/MUM/2013 | 2013-03-26 | ||
| IN1165MU2013 IN2013MU01165A (https=) | 2013-03-26 | 2013-03-26 | |
| CN201480018900.7A CN105102406B (zh) | 2013-03-26 | 2014-03-20 | 用于控制和抑制脂肪族单体聚合的添加剂组合物，及其制备和使用方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480018900.7A Division CN105102406B (zh) | 2013-03-26 | 2014-03-20 | 用于控制和抑制脂肪族单体聚合的添加剂组合物，及其制备和使用方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107814681A true CN107814681A (zh) | 2018-03-20 |
Family
ID=50489360
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711010294.6A Pending CN107814681A (zh) | 2013-03-26 | 2014-03-20 | 用于控制和抑制脂肪族单体聚合的添加剂组合物，及其制备和使用方法 |
| CN201480018900.7A Expired - Fee Related CN105102406B (zh) | 2013-03-26 | 2014-03-20 | 用于控制和抑制脂肪族单体聚合的添加剂组合物，及其制备和使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480018900.7A Expired - Fee Related CN105102406B (zh) | 2013-03-26 | 2014-03-20 | 用于控制和抑制脂肪族单体聚合的添加剂组合物，及其制备和使用方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9598333B2 (https=) |
| EP (1) | EP2978735B1 (https=) |
| JP (1) | JP6433483B2 (https=) |
| KR (1) | KR102058646B1 (https=) |
| CN (2) | CN107814681A (https=) |
| AR (1) | AR095709A1 (https=) |
| BR (1) | BR112015024595B1 (https=) |
| CA (1) | CA2907963C (https=) |
| ES (1) | ES2813614T3 (https=) |
| IN (1) | IN2013MU01165A (https=) |
| MX (1) | MX350061B (https=) |
| MY (1) | MY169124A (https=) |
| PH (1) | PH12015502195B1 (https=) |
| PL (1) | PL2978735T3 (https=) |
| RU (1) | RU2725611C2 (https=) |
| SG (1) | SG11201507999SA (https=) |
| TW (1) | TWI657075B (https=) |
| WO (1) | WO2014155248A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2758521C (en) * | 2009-04-15 | 2015-02-17 | Dorf Ketal Chemicals (I) Pvt. Ltd. | An effective novel non - polymeric and non - fouling additive for inhibiting high - temperature naphthenic acid corrosion and method of using the same |
| IN2013MU01165A (https=) | 2013-03-26 | 2015-04-24 | Dorf Ketal Chemicals India Private Ltd | |
| US11180578B2 (en) | 2018-07-13 | 2021-11-23 | Ecolab Usa Inc. | Polymerization inhibitor and retarder compositions with amine stabilizer |
| EP3820836A1 (en) | 2018-07-13 | 2021-05-19 | Ecolab USA, Inc. | Compositions of oxygenated amines and quinone methides as antifoulants for vinylic monomers |
| TWI880966B (zh) | 2019-10-11 | 2025-04-21 | 美商藝康美國公司 | 醌甲基化物及銨鹽抗聚合劑組合物及方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002094884A2 (en) * | 2001-05-22 | 2002-11-28 | Ge Betz, Inc. | Methods and compositions for inhibiting polymerization of vinyl monomers |
| CN101102984A (zh) * | 2004-12-03 | 2008-01-09 | 科聚亚公司 | 作为聚合抑制剂的与含氮氧自由基的化合物或c-亚硝基苯胺结合的芳族磺酸、胺和硝基酚 |
| CN101189203A (zh) * | 2005-06-17 | 2008-05-28 | 科聚亚公司 | 作为聚合抑制剂的邻亚硝基苯酚 |
| CN103764686A (zh) * | 2011-08-26 | 2014-04-30 | 多尔夫凯塔尔化学制品（I）私人有限公司 | 用于控制及抑制苯乙烯聚合反应的添加剂组合物、及其制备和使用方法 |
| CN103998404A (zh) * | 2011-12-26 | 2014-08-20 | 多尔夫凯塔尔化学制品（I）私人有限公司 | 用于控制及抑制芳香族乙烯基单体聚合的改良的基于胺的添加剂组合物，及其使用方法 |
| CN104350095A (zh) * | 2011-12-02 | 2015-02-11 | 多尔夫凯塔尔化学制品（I）私人有限公司 | 用于控制及抑制苯乙烯聚合的基于胺与氮氧化物的添加剂组合物及其使用方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5290888A (en) * | 1990-07-20 | 1994-03-01 | Ciba-Geigy Corporation | Process for stabilizing ethylenically unsaturated compounds and stabilized monomer compositions |
| RU2129112C1 (ru) * | 1997-03-25 | 1999-04-20 | Открытое акционерное общество "Ангарский завод полимеров" | Способ ингибирования термополимеризации стирола |
| RU2152377C1 (ru) * | 1998-07-29 | 2000-07-10 | Открытое акционерное общество "Ангарский завод полимеров" | Ингибирующая композиция термополимеризации стирола |
| US6200461B1 (en) * | 1998-11-05 | 2001-03-13 | Betzdearborn Inc. | Method for inhibiting polymerization of ethylenically unsaturated hydrocarbons |
| ES2292487T3 (es) * | 1999-12-03 | 2008-03-16 | Chemtura Corporation | Composicion y metodo para inhibir la polimerizacion y el crecimiento polimerico. |
| US6403850B1 (en) * | 2000-01-18 | 2002-06-11 | Uniroyal Chemical Company, Inc. | Inhibition of polymerization of unsaturated monomers |
| US7045647B2 (en) * | 2000-10-16 | 2006-05-16 | Uniroyal Chemical Company, Inc. | Blends of quinone alkide and nitroxyl compounds and polymerization inhibitors |
| US6525147B1 (en) * | 2001-06-20 | 2003-02-25 | Baker Hughes Incorporated | Use of diamines and alkanolamines to inhibit unsaturated monomer polymerization |
| WO2003106390A1 (en) * | 2002-06-13 | 2003-12-24 | A H Marks & Company Limited | Polymerisation inhibitor |
| CA2565160C (en) * | 2004-05-26 | 2013-02-12 | Jean-Roch Pauquet | Flame-retardants |
| US7696290B2 (en) * | 2004-12-03 | 2010-04-13 | Crompton Corporation | Aromatic sulfonic acids, amines, and nitrophenols in combination with nitroxyl radical-containing compounds or C-nitrosanilines as polymerization inhibitors |
| DE102007052891A1 (de) * | 2007-11-02 | 2009-05-07 | Evonik Degussa Gmbh | Verfahren zur Stabilisierung von olefinisch ungesättigten Monomeren |
| US7651635B1 (en) * | 2009-02-05 | 2010-01-26 | Nalco Company | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxylamine combination |
| US9090526B2 (en) * | 2011-06-13 | 2015-07-28 | Nalco Company | Synergistic combination for inhibiting polymerization of vinyl monomers |
| RU2612507C2 (ru) * | 2011-11-29 | 2017-03-09 | Дорф Кетал Кемикалс (Индия) Прайвит Лимитэд | Композиция добавки на основе амина для контроля и ингибирования полимеризации стирола и способ ее использования |
| BR112014013855B1 (pt) * | 2011-12-09 | 2020-11-17 | Dorf Ketal Chemicals (I) Private Limited | composição aditiva para o controle e inibição de polimerização de monômeros vinil aromáticos e método de utilização da mesma |
| US9234057B2 (en) * | 2012-08-24 | 2016-01-12 | Dorf Ketal Chemicals (India) Private Limited | Composition of quinone methide derivatives and amines for control and inhibition of polymerization of monomers, and method of preparation and use thereof |
| IN2013MU01165A (https=) | 2013-03-26 | 2015-04-24 | Dorf Ketal Chemicals India Private Ltd |
-
2013
- 2013-03-26 IN IN1165MU2013 patent/IN2013MU01165A/en unknown
-
2014
- 2014-03-20 PL PL14717873T patent/PL2978735T3/pl unknown
- 2014-03-20 MX MX2015013718A patent/MX350061B/es active IP Right Grant
- 2014-03-20 MY MYPI2015002441A patent/MY169124A/en unknown
- 2014-03-20 KR KR1020157030584A patent/KR102058646B1/ko active Active
- 2014-03-20 CN CN201711010294.6A patent/CN107814681A/zh active Pending
- 2014-03-20 JP JP2016504793A patent/JP6433483B2/ja active Active
- 2014-03-20 CN CN201480018900.7A patent/CN105102406B/zh not_active Expired - Fee Related
- 2014-03-20 EP EP14717873.5A patent/EP2978735B1/en active Active
- 2014-03-20 BR BR112015024595-1A patent/BR112015024595B1/pt active IP Right Grant
- 2014-03-20 CA CA2907963A patent/CA2907963C/en active Active
- 2014-03-20 ES ES14717873T patent/ES2813614T3/es active Active
- 2014-03-20 US US14/779,843 patent/US9598333B2/en active Active
- 2014-03-20 WO PCT/IB2014/059998 patent/WO2014155248A1/en not_active Ceased
- 2014-03-20 SG SG11201507999SA patent/SG11201507999SA/en unknown
- 2014-03-20 RU RU2015145214A patent/RU2725611C2/ru active
- 2014-03-21 AR ARP140101322A patent/AR095709A1/es active IP Right Grant
- 2014-03-24 TW TW103110898A patent/TWI657075B/zh active
-
2015
- 2015-09-21 PH PH12015502195A patent/PH12015502195B1/en unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002094884A2 (en) * | 2001-05-22 | 2002-11-28 | Ge Betz, Inc. | Methods and compositions for inhibiting polymerization of vinyl monomers |
| CN101102984A (zh) * | 2004-12-03 | 2008-01-09 | 科聚亚公司 | 作为聚合抑制剂的与含氮氧自由基的化合物或c-亚硝基苯胺结合的芳族磺酸、胺和硝基酚 |
| CN101189203A (zh) * | 2005-06-17 | 2008-05-28 | 科聚亚公司 | 作为聚合抑制剂的邻亚硝基苯酚 |
| CN103764686A (zh) * | 2011-08-26 | 2014-04-30 | 多尔夫凯塔尔化学制品（I）私人有限公司 | 用于控制及抑制苯乙烯聚合反应的添加剂组合物、及其制备和使用方法 |
| CN104350095A (zh) * | 2011-12-02 | 2015-02-11 | 多尔夫凯塔尔化学制品（I）私人有限公司 | 用于控制及抑制苯乙烯聚合的基于胺与氮氧化物的添加剂组合物及其使用方法 |
| CN103998404A (zh) * | 2011-12-26 | 2014-08-20 | 多尔夫凯塔尔化学制品（I）私人有限公司 | 用于控制及抑制芳香族乙烯基单体聚合的改良的基于胺的添加剂组合物，及其使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102058646B1 (ko) | 2019-12-23 |
| PH12015502195A1 (en) | 2016-01-25 |
| PH12015502195B1 (en) | 2016-01-25 |
| PL2978735T3 (pl) | 2020-11-16 |
| EP2978735B1 (en) | 2020-06-24 |
| CN105102406A (zh) | 2015-11-25 |
| KR20150134404A (ko) | 2015-12-01 |
| CN105102406B (zh) | 2018-07-06 |
| CA2907963A1 (en) | 2014-10-02 |
| MX2015013718A (es) | 2016-07-06 |
| US9598333B2 (en) | 2017-03-21 |
| ES2813614T3 (es) | 2021-03-24 |
| RU2015145214A (ru) | 2017-04-25 |
| IN2013MU01165A (https=) | 2015-04-24 |
| SG11201507999SA (en) | 2015-10-29 |
| MX350061B (es) | 2017-08-25 |
| US20160083315A1 (en) | 2016-03-24 |
| EP2978735A1 (en) | 2016-02-03 |
| MY169124A (en) | 2019-02-18 |
| JP6433483B2 (ja) | 2018-12-05 |
| TW201446735A (zh) | 2014-12-16 |
| AR095709A1 (es) | 2015-11-04 |
| BR112015024595B1 (pt) | 2020-12-15 |
| WO2014155248A1 (en) | 2014-10-02 |
| BR112015024595A2 (pt) | 2017-08-22 |
| RU2725611C2 (ru) | 2020-07-03 |
| TWI657075B (zh) | 2019-04-21 |
| CA2907963C (en) | 2017-08-01 |
| JP2016520674A (ja) | 2016-07-14 |
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