JP2015512989A5 - - Google Patents
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- JP2015512989A5 JP2015512989A5 JP2015502188A JP2015502188A JP2015512989A5 JP 2015512989 A5 JP2015512989 A5 JP 2015512989A5 JP 2015502188 A JP2015502188 A JP 2015502188A JP 2015502188 A JP2015502188 A JP 2015502188A JP 2015512989 A5 JP2015512989 A5 JP 2015512989A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- groups
- composition according
- polyisocyanate composition
- 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 claims description 104
- 150000001875 compounds Chemical class 0.000 claims description 74
- 239000003054 catalyst Substances 0.000 claims description 48
- 229920001228 polyisocyanate Polymers 0.000 claims description 48
- 239000005056 polyisocyanate Substances 0.000 claims description 48
- 238000005829 trimerization reaction Methods 0.000 claims description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 19
- 229920005862 polyol Polymers 0.000 claims description 19
- 150000003077 polyols Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000001033 ether group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 7
- 229920005906 polyester polyol Polymers 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- -1 alkali metal salt Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000007942 carboxylates Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000002524 organometallic group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- 229920000582 polyisocyanurate Polymers 0.000 claims description 4
- 239000011495 polyisocyanurate Substances 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001744 Sodium fumarate Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 claims description 2
- SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 239000004300 potassium benzoate Substances 0.000 claims description 2
- 235000010235 potassium benzoate Nutrition 0.000 claims description 2
- 229940103091 potassium benzoate Drugs 0.000 claims description 2
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 2
- 239000001521 potassium lactate Substances 0.000 claims description 2
- 235000011085 potassium lactate Nutrition 0.000 claims description 2
- 229960001304 potassium lactate Drugs 0.000 claims description 2
- BLGUIMKBRCQORR-UHFFFAOYSA-M potassium;hexanoate Chemical compound [K+].CCCCCC([O-])=O BLGUIMKBRCQORR-UHFFFAOYSA-M 0.000 claims description 2
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940005573 sodium fumarate Drugs 0.000 claims description 2
- 235000019294 sodium fumarate Nutrition 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 1
- 239000001747 Potassium fumarate Substances 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- SHPKCSFVQGSAJU-SEPHDYHBSA-L potassium fumarate Chemical compound [K+].[K+].[O-]C(=O)\C=C\C([O-])=O SHPKCSFVQGSAJU-SEPHDYHBSA-L 0.000 claims 1
- 235000019295 potassium fumarate Nutrition 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12162154.4A EP2644270A1 (en) | 2012-03-29 | 2012-03-29 | Polyisocyanate trimerization catalyst composition |
| EP12162154.4 | 2012-03-29 | ||
| PCT/EP2013/055014 WO2013143841A1 (en) | 2012-03-29 | 2013-03-12 | Polyisocyanate trimerization catalyst composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015512989A JP2015512989A (ja) | 2015-04-30 |
| JP2015512989A5 true JP2015512989A5 (enExample) | 2015-11-12 |
Family
ID=47844386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015502188A Pending JP2015512989A (ja) | 2012-03-29 | 2013-03-12 | ポリイソシアネート三量化触媒組成物 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20150031527A1 (enExample) |
| EP (2) | EP2644270A1 (enExample) |
| JP (1) | JP2015512989A (enExample) |
| KR (1) | KR20140143411A (enExample) |
| CN (2) | CN109553739A (enExample) |
| BR (1) | BR112014023105B1 (enExample) |
| CA (1) | CA2866990C (enExample) |
| IN (1) | IN2014DN07402A (enExample) |
| MX (1) | MX370889B (enExample) |
| RU (1) | RU2628084C2 (enExample) |
| TW (1) | TWI491446B (enExample) |
| WO (1) | WO2013143841A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2687551A1 (en) * | 2012-07-17 | 2014-01-22 | Huntsman International Llc | Intermediate polyisocyanurate comprising materials |
| EP2805976A1 (en) * | 2013-05-24 | 2014-11-26 | Huntsman International Llc | Aldehyde comprising compositions suitable for making curable polyisocyanate compositions |
| AU2014356702B2 (en) | 2013-11-29 | 2018-03-15 | Basf Se | Polyurethane system with long pot life and rapid hardening |
| CA2986802A1 (en) * | 2015-05-27 | 2016-12-01 | Basf Se | Use of a composition for stabilizing a geological formation in oil fields, gas fields, water pumping fields, mining or tunnel constructions |
| MX391443B (es) | 2015-05-28 | 2025-03-21 | Basf Se | Compuesto de poliuretano-poliisocianurato que comprende excelentes propiedades mecanicas. |
| DK3303437T3 (da) * | 2015-05-29 | 2020-03-16 | Basf Se | Polyurethan-polyisocyanurat-harpiks til fiber-kompositmaterialer med lang åben klæbetid |
| EP3390509B1 (en) * | 2015-12-18 | 2020-03-04 | Sika Technology AG | Heat expandable foam for low temperature cure |
| CN109153764B (zh) * | 2016-05-18 | 2021-12-21 | 巴斯夫欧洲公司 | 制备聚异氰脲酸酯硬质泡沫的方法 |
| US12447699B2 (en) * | 2016-09-20 | 2025-10-21 | Covestro Deutschland Ag | Anisotropic composite materials based on polyisocyanates |
| EP3381962A1 (de) * | 2017-03-29 | 2018-10-03 | Covestro Deutschland AG | Erzeugung von polyisocyanuratschichten durch getrennte auftragung von isocyanatkomponenten und katalysatoren |
| CN108730753B (zh) * | 2017-04-14 | 2020-07-07 | 江苏先诺新材料科技有限公司 | 一种聚酰亚胺纤维复合材料气瓶及其制备方法和应用 |
| WO2020074293A1 (en) | 2018-10-09 | 2020-04-16 | Basf Se | A process for preparing a prepreg binder composition, a prepreg and use thereof |
| CN117586473A (zh) * | 2018-12-11 | 2024-02-23 | 三聚体科技有限责任公司 | 聚异氰脲酸酯基聚合物和纤维增强复合材料 |
| WO2020165135A1 (en) | 2019-02-11 | 2020-08-20 | Basf Se | Acrylic copolymer capsule designed to open up at < 90°c for controlled release of in-situ forming pu/pir catalyst |
| US12319777B2 (en) | 2019-08-19 | 2025-06-03 | Basf Se | Polyurethane-polyisocyanurate compound with outstanding mechanical properties |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1230778B (de) | 1965-05-24 | 1966-12-22 | Bayer Ag | Verfahren zur Herstellung von acylierten Harnstoffpolyisocyanaten |
| GB1234728A (en) * | 1968-09-11 | 1971-06-09 | Takeda Chemical Industries Ltd | Method for producing organic isocyanate polymers |
| GB1340068A (en) | 1970-09-22 | 1973-12-05 | Insituform Pipes & Structures | Lining of surfaces defining passageways |
| DE2403858A1 (de) | 1974-01-28 | 1975-08-21 | Basf Ag | Stabile, fluessige amid- und/oder acylharnstoffgruppenhaltige isocyanurat-polyisocyanatloesungen |
| US3903018A (en) * | 1974-01-30 | 1975-09-02 | Upjohn Co | Novel cocatalyst system for trimerizing polyisocyanates |
| JPS5152499A (en) * | 1974-11-01 | 1976-05-10 | Hitachi Ltd | Tainetsuseijushino seizohoho |
| DE2712931A1 (de) | 1977-03-24 | 1978-09-28 | Veba Chemie Ag | Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen - enthaltende verbindungen |
| US4284730A (en) | 1980-02-07 | 1981-08-18 | Basf Wyandotte Corporation | Liquid carbodiimide- and uretonimine-isocyanurate-containing polyisocyanate compositions and microcellular foams made therefrom |
| US4366012A (en) | 1981-02-05 | 1982-12-28 | Insituform International Inc. | Impregnation process |
| FR2522667A1 (fr) | 1982-03-04 | 1983-09-09 | Rhone Poulenc Spec Chim | Procede de preparation de polyisocyanates polyisocyanurates par cyclotrimerisation catalytique de polyisocyanates |
| GB8400365D0 (en) | 1984-01-07 | 1984-02-08 | Edgealpha Ltd | Lining of pipelines and passageways |
| FR2579205B1 (fr) | 1985-03-25 | 1987-05-15 | Rhone Poulenc Spec Chim | Procede de preparation de polyisocyanates polyisocyanurates par cyclotrimerisation catalytique de polyisocyanates |
| US4658007A (en) | 1985-05-07 | 1987-04-14 | The Dow Chemical Company | Polyisocyanurate-based polyoxazolidone polymers and process for their preparation |
| US4743627A (en) | 1987-09-14 | 1988-05-10 | Basf Corporation | Liquid isocyanurate-modified polymethylene bis(phenylisocyanate) compositions containing a high two-ring methylene bis(phenylisocyanate) content |
| JPH02110123A (ja) | 1988-10-19 | 1990-04-23 | Asahi Chem Ind Co Ltd | ポリイソシアナートの製法 |
| JPH0395213A (ja) * | 1989-05-11 | 1991-04-19 | Teijin Ltd | 複合系硬化性液状樹脂組成物 |
| AU645290B2 (en) | 1990-03-07 | 1994-01-13 | Huntsman Ici Chemicals Llc | Polyisocyanate composition |
| DE4026474A1 (de) | 1990-08-22 | 1992-02-27 | Bayer Ag | Neue isocyanuratgruppen aufweisende polyisocyanatmischungen, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polyurethanschaumstoffen |
| US5157074A (en) * | 1991-07-23 | 1992-10-20 | Miles Inc. | Aqueous compositions containing an at least partially blocked polyisocyanates and a trimerization catalyst and coatings and binders prepared therefrom |
| US5221743A (en) | 1992-03-02 | 1993-06-22 | Olin Corporation | Process for producing isocyanurates by cyclotrimerizing isocyanates using polymer-bound catalysts |
| DE4229183A1 (de) | 1992-09-02 | 1994-03-03 | Basf Ag | Verfahren zur Herstellung von niedrigviskosen Isocyanurat- und Urethangruppen enthaltenden Polyisocyanatmischungen |
| JP3358261B2 (ja) * | 1992-11-13 | 2002-12-16 | 日本ポリウレタン工業株式会社 | ポリウレタン塗料組成物およびポリウレタン接着剤組成物 |
| US5817732A (en) | 1993-02-12 | 1998-10-06 | Asahi Kasei Kogyo Kabushiki Kaisha | Blocked polyisocyanate and coating composition |
| DE4309689A1 (de) * | 1993-03-25 | 1994-09-29 | Bayer Ag | Verfahren zur Herstellung von Polyurethanschaumstoffen |
| US5288899A (en) * | 1993-06-30 | 1994-02-22 | Miles Inc. | Liquification of diphenylmethane diisocyanate by partially reacting the isocyanate groups with blocking agents |
| US5955609A (en) | 1997-12-31 | 1999-09-21 | Bayer Corporation | Trimer catalyst system for aliphatic and aromatic isocyanates |
| FR2818974B1 (fr) * | 2000-12-29 | 2003-10-24 | Rhodia Chimie Sa | (cyclo) condensation de composes isocyanates |
| DE10110437A1 (de) * | 2001-03-05 | 2002-09-19 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten durch Umsetzung von Carbonsäuren mit Isocyanaten, die nach diesem Verfahren hergestellten Produkte und deren Verwendung in Polyurethankunststoffen |
| EP1288239A1 (en) * | 2001-08-30 | 2003-03-05 | Huntsman International Llc | Process for making rigid urethane-modified polyisocyanurate foams |
| US7553963B2 (en) | 2003-10-29 | 2009-06-30 | Bayer Materialscience Llc | Liquid partially trimerized and allophanized polyisocyanates based on toluene diisocyanate and diphenylmethane diisocyanate |
| US20060223969A1 (en) * | 2005-03-31 | 2006-10-05 | Bayer Materialscience Llc | Low surface energy polyisocyanates and their use in one- or two-component coating compositions |
| DE102005034052A1 (de) * | 2005-07-21 | 2007-01-25 | Goldschmidt Gmbh | Trimerisierungskatalysatoren |
| JP5159640B2 (ja) | 2006-02-21 | 2013-03-06 | ハンツマン・インターナショナル・エルエルシー | ポリイソシアヌレート複合物の製造方法 |
| US7666971B2 (en) * | 2006-11-14 | 2010-02-23 | Bayer Materialscience Llc | Amide/urea-modified liquid diphenylmethane diisocyanates |
| US8445622B2 (en) * | 2006-12-04 | 2013-05-21 | Basf Se | Process for preparing polyisocyanates |
| US8373004B2 (en) | 2007-03-27 | 2013-02-12 | Basf Se | Method for producing colorless isocyanurates of diisocyanates |
| CN101646700B (zh) * | 2007-03-27 | 2013-05-22 | 巴斯夫欧洲公司 | 生产二异氰酸酯的无色异氰脲酸酯的方法 |
| WO2008147641A1 (en) * | 2007-05-29 | 2008-12-04 | Dow Global Technologies Inc. | Isocyanate-epoxy formulations for improved cure control |
| CA2732421C (en) | 2008-08-28 | 2016-05-17 | Huntsman International Llc | Mixture obtained by reacting polyol and anhydride and its use in polyisocyanates for making polyisocyanurates |
| PL2421906T3 (pl) * | 2009-04-21 | 2017-08-31 | Huntsman International Llc | Kompozycja poliizocyjanianowa |
| WO2013075938A1 (en) * | 2011-11-22 | 2013-05-30 | Huntsman International Llc | Curable polyisocyanate composition comprising an epoxy resin |
| JP2015504110A (ja) * | 2011-12-28 | 2015-02-05 | ハンツマン・インターナショナル・エルエルシー | ポリイソシアネート組成物を含む硬化性組成物 |
-
2012
- 2012-03-29 EP EP12162154.4A patent/EP2644270A1/en not_active Ceased
-
2013
- 2013-03-12 WO PCT/EP2013/055014 patent/WO2013143841A1/en not_active Ceased
- 2013-03-12 MX MX2014011587A patent/MX370889B/es active IP Right Grant
- 2013-03-12 EP EP13708493.5A patent/EP2830761B1/en active Active
- 2013-03-12 JP JP2015502188A patent/JP2015512989A/ja active Pending
- 2013-03-12 BR BR112014023105-2A patent/BR112014023105B1/pt not_active IP Right Cessation
- 2013-03-12 RU RU2014143488A patent/RU2628084C2/ru active
- 2013-03-12 US US14/382,020 patent/US20150031527A1/en not_active Abandoned
- 2013-03-12 KR KR1020147029847A patent/KR20140143411A/ko not_active Ceased
- 2013-03-12 CA CA2866990A patent/CA2866990C/en active Active
- 2013-03-12 CN CN201811358609.0A patent/CN109553739A/zh active Pending
- 2013-03-12 CN CN201380016760.5A patent/CN104394985A/zh active Pending
- 2013-03-12 IN IN7402DEN2014 patent/IN2014DN07402A/en unknown
- 2013-03-22 TW TW102110385A patent/TWI491446B/zh not_active IP Right Cessation
-
2022
- 2022-01-18 US US17/577,896 patent/US20220134322A1/en active Pending
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