SE520715C2 - Förfarande för framställning av metylcellulosaetrar - Google Patents
Förfarande för framställning av metylcellulosaetrarInfo
- Publication number
- SE520715C2 SE520715C2 SE0104047A SE0104047A SE520715C2 SE 520715 C2 SE520715 C2 SE 520715C2 SE 0104047 A SE0104047 A SE 0104047A SE 0104047 A SE0104047 A SE 0104047A SE 520715 C2 SE520715 C2 SE 520715C2
- Authority
- SE
- Sweden
- Prior art keywords
- chloride
- methyl
- cellulose
- process according
- temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- -1 methyl cellulose ethers Chemical class 0.000 title claims description 16
- 229920000609 methyl cellulose Polymers 0.000 title claims description 8
- 239000001923 methylcellulose Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 235000010981 methylcellulose Nutrition 0.000 title description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 229940050176 methyl chloride Drugs 0.000 claims abstract description 29
- 229920002678 cellulose Polymers 0.000 claims abstract description 22
- 239000001913 cellulose Substances 0.000 claims abstract description 22
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 claims abstract description 12
- 239000012429 reaction media Substances 0.000 claims abstract description 10
- 238000005189 flocculation Methods 0.000 claims abstract description 9
- 230000016615 flocculation Effects 0.000 claims abstract description 9
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 19
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 11
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 10
- 229960003750 ethyl chloride Drugs 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000005517 mercerization Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 230000004913 activation Effects 0.000 claims description 4
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 229920000896 Ethulose Polymers 0.000 claims description 2
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000000837 carbohydrate group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000001348 alkyl chlorides Chemical class 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 229920003086 cellulose ether Polymers 0.000 description 18
- 238000006467 substitution reaction Methods 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000011987 methylation Effects 0.000 description 5
- 238000007069 methylation reaction Methods 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001720 carbohydrates Chemical group 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006203 ethylation Effects 0.000 description 2
- 238000006200 ethylation reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/193—Mixed ethers, i.e. ethers with two or more different etherifying groups
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0104047A SE520715C2 (sv) | 2001-12-03 | 2001-12-03 | Förfarande för framställning av metylcellulosaetrar |
| AT02789108T ATE360649T1 (de) | 2001-12-03 | 2002-11-26 | Verfahren zur herstellung von methylcelluloseether |
| AU2002353732A AU2002353732A1 (en) | 2001-12-03 | 2002-11-26 | Process for the manufacture of methyl cellulose ether |
| DE60219819T DE60219819T2 (de) | 2001-12-03 | 2002-11-26 | Verfahren zur herstellung von methylcelluloseether |
| CNB028241428A CN1286851C (zh) | 2001-12-03 | 2002-11-26 | 生产甲基纤维素醚的方法 |
| BR0214402-6A BR0214402A (pt) | 2001-12-03 | 2002-11-26 | Processo para fabricação de éter de metil celulose |
| MXPA04005141A MXPA04005141A (es) | 2001-12-03 | 2002-11-26 | Proceso para la elaboracion de eter de metilcelulosa. |
| PCT/SE2002/002165 WO2003048211A1 (en) | 2001-12-03 | 2002-11-26 | Process for the manufacture of methyl cellulose ether |
| US10/497,332 US7504498B2 (en) | 2001-12-03 | 2002-11-26 | Process for the manufacture of methyl cellulose ether |
| KR1020047008394A KR100908312B1 (ko) | 2001-12-03 | 2002-11-26 | 메틸 셀룰로스 에테르의 제조 방법 |
| ES02789108T ES2286311T3 (es) | 2001-12-03 | 2002-11-26 | Procedimiento para la elaboracion de eter de metilcelulosa. |
| EP02789108A EP1453863B1 (de) | 2001-12-03 | 2002-11-26 | Verfahren zur herstellung von methylcelluloseether |
| JP2003549397A JP4568830B2 (ja) | 2001-12-03 | 2002-11-26 | メチルセルロースエーテルの製造のための方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0104047A SE520715C2 (sv) | 2001-12-03 | 2001-12-03 | Förfarande för framställning av metylcellulosaetrar |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE0104047L SE0104047L (sv) | 2003-06-04 |
| SE520715C2 true SE520715C2 (sv) | 2003-08-12 |
Family
ID=20286176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE0104047A SE520715C2 (sv) | 2001-12-03 | 2001-12-03 | Förfarande för framställning av metylcellulosaetrar |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7504498B2 (de) |
| EP (1) | EP1453863B1 (de) |
| JP (1) | JP4568830B2 (de) |
| KR (1) | KR100908312B1 (de) |
| CN (1) | CN1286851C (de) |
| AT (1) | ATE360649T1 (de) |
| AU (1) | AU2002353732A1 (de) |
| BR (1) | BR0214402A (de) |
| DE (1) | DE60219819T2 (de) |
| ES (1) | ES2286311T3 (de) |
| MX (1) | MXPA04005141A (de) |
| SE (1) | SE520715C2 (de) |
| WO (1) | WO2003048211A1 (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0300235D0 (sv) | 2003-01-31 | 2003-01-31 | Akzo Nobel Nv | A nonionic cellulose ether and its use |
| SE526356C2 (sv) * | 2003-12-15 | 2005-08-30 | Akzo Nobel Nv | Associativa vattenlösliga cellulosaetrar |
| DE102006039873B4 (de) * | 2006-08-25 | 2013-10-31 | Henkel Ag & Co. Kgaa | Verstärkung der Reinigungsleistung von Waschmitteln durch baumwollaktives schmutzablösevermögendes Cellulosederivat |
| CN101280023B (zh) * | 2008-01-31 | 2010-12-01 | 重庆力宏精细化工有限公司 | 一种耐酸型羧甲基纤维素钠的制备方法 |
| JP5412191B2 (ja) * | 2009-06-29 | 2014-02-12 | 富士フイルム株式会社 | セルロース樹脂組成物、成形体および電気電子機器用筐体 |
| JP5819941B2 (ja) * | 2010-04-26 | 2015-11-24 | ダウ グローバル テクノロジーズ エルエルシー | 押出成形体用の組成物 |
| CN102391380B (zh) * | 2011-08-26 | 2013-05-22 | 大连工业大学 | 一种大麻杆纤维素复合醚及其制备方法 |
| CN105050396B (zh) | 2013-03-14 | 2018-12-21 | 阿克佐诺贝尔化学国际公司 | 作为漂移控制剂和耐雨剂的纤维素醚 |
| CN105731878A (zh) * | 2014-09-05 | 2016-07-06 | 赫尔克里士公司 | 石漆配制品及其生产方法 |
| CN105017431A (zh) * | 2015-08-19 | 2015-11-04 | 昆山京昆油田化学科技开发公司 | 一种甲基纤维素样品的合成方法 |
| CN105384829A (zh) * | 2015-12-14 | 2016-03-09 | 山东一滕新材料股份有限公司 | 羧甲基羟乙基甲基纤维素醚及其制备方法 |
| CN105384830A (zh) * | 2015-12-14 | 2016-03-09 | 山东一滕新材料股份有限公司 | 羟丙基羟乙基纤维素醚及其制备方法 |
| CN105566501A (zh) * | 2016-03-11 | 2016-05-11 | 山东一滕新材料股份有限公司 | 干法制备纤维素醚 |
| US11834522B2 (en) * | 2017-08-17 | 2023-12-05 | Nouryon Chemicals International B.V. | Methyl-ethyl-hydroxyalkyl-cellulose and its use in building compositions |
| CN108570110A (zh) * | 2018-06-21 | 2018-09-25 | 浙江中维药业股份有限公司 | 一种羟丙基甲基纤维素的制备方法 |
| JP7615049B2 (ja) * | 2019-05-01 | 2025-01-16 | ダウ グローバル テクノロジーズ エルエルシー | 架橋セルロースエーテルを製造するためのプロセス |
| US12121047B2 (en) | 2022-06-14 | 2024-10-22 | Botany Al, Inc. | Dynamically delivering fat and flavor potentiators to foods and methods of use thereof |
| WO2023245070A2 (en) * | 2022-06-14 | 2023-12-21 | BOTANY AL, INC., dba UMMINO | Dynamically delivering fat and flavor potentiators to foods and methods of use thereof |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB162197A (en) | 1920-05-14 | 1921-04-28 | Charles Davis | Improvements in and relating to means for packing and displaying soap or other articles |
| US3342805A (en) | 1964-05-27 | 1967-09-19 | Dow Chemical Co | Process for the manufacture of cellulose ethers |
| GB1162197A (en) * | 1968-02-13 | 1969-08-20 | Vladimirsky Nii Sint Smol | A Method for the Manufacture of Methylcellulose |
| DE2635403B2 (de) * | 1976-08-06 | 1979-07-12 | Loedige Fritz | Verfahren zum Herstellen von CeUuIoseäthern |
| JPS5951561B2 (ja) * | 1978-09-01 | 1984-12-14 | 株式会社興人 | セルロ−スエ−テルの製造方法 |
| DE3140813A1 (de) * | 1981-10-14 | 1983-04-21 | Wolff Walsrode Ag, 3030 Walsrode | Verfahren zur herstellung von celluloseethern |
| DE3306621A1 (de) | 1983-02-25 | 1984-08-30 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von celluloseethern mit einem dimethoxyethan enthaltenden dispergierhilfsmittel |
| DE3316124A1 (de) * | 1983-05-03 | 1984-11-08 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von wasserloeslichen cellulosemischethern |
| DE3628826A1 (de) | 1986-08-25 | 1988-03-03 | Henkel Kgaa | Verfahren zur aufarbeitung von wasserloeslichen cellulosederivaten mit hohen flockungspunkten |
| US5032392A (en) * | 1986-09-04 | 1991-07-16 | Vision Pharmaceuticals | Aqueous ophthalmic solutions for the treatment of dryness and/or irritation of human or animal eyes |
| US4845206A (en) * | 1987-05-21 | 1989-07-04 | The Dow Chemical Company | Production of cellulose ethers using a premix of alkali and etherifying agent |
| JPH07119241B2 (ja) * | 1989-11-02 | 1995-12-20 | 信越化学工業株式会社 | 高重合度セルロースエーテルの製造方法 |
| DE59309448D1 (de) * | 1992-06-06 | 1999-04-22 | Clariant Gmbh | Verwendung von carboxymethylierten Methylhydroxyethyl- oder Methylhydroxypropylcelluloseethern und daraus erhältliche Zementmischungen |
| US6434654B1 (en) * | 1999-03-26 | 2002-08-13 | Koninklijke Philips Electronics N.V. | System bus with a variable width selectivity configurable at initialization |
| AU3932400A (en) | 1999-04-01 | 2000-10-23 | Dow Chemical Company, The | Enhanced gel strength methylcellulose |
-
2001
- 2001-12-03 SE SE0104047A patent/SE520715C2/sv not_active IP Right Cessation
-
2002
- 2002-11-26 AT AT02789108T patent/ATE360649T1/de not_active IP Right Cessation
- 2002-11-26 CN CNB028241428A patent/CN1286851C/zh not_active Expired - Fee Related
- 2002-11-26 JP JP2003549397A patent/JP4568830B2/ja not_active Expired - Fee Related
- 2002-11-26 EP EP02789108A patent/EP1453863B1/de not_active Expired - Lifetime
- 2002-11-26 US US10/497,332 patent/US7504498B2/en not_active Expired - Lifetime
- 2002-11-26 ES ES02789108T patent/ES2286311T3/es not_active Expired - Lifetime
- 2002-11-26 AU AU2002353732A patent/AU2002353732A1/en not_active Abandoned
- 2002-11-26 WO PCT/SE2002/002165 patent/WO2003048211A1/en not_active Ceased
- 2002-11-26 DE DE60219819T patent/DE60219819T2/de not_active Expired - Lifetime
- 2002-11-26 MX MXPA04005141A patent/MXPA04005141A/es active IP Right Grant
- 2002-11-26 KR KR1020047008394A patent/KR100908312B1/ko not_active Expired - Fee Related
- 2002-11-26 BR BR0214402-6A patent/BR0214402A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20050176951A1 (en) | 2005-08-11 |
| MXPA04005141A (es) | 2004-08-11 |
| WO2003048211A1 (en) | 2003-06-12 |
| DE60219819D1 (de) | 2007-06-06 |
| KR100908312B1 (ko) | 2009-07-17 |
| ATE360649T1 (de) | 2007-05-15 |
| US7504498B2 (en) | 2009-03-17 |
| DE60219819T2 (de) | 2008-01-17 |
| CN1286851C (zh) | 2006-11-29 |
| JP4568830B2 (ja) | 2010-10-27 |
| BR0214402A (pt) | 2004-11-03 |
| ES2286311T3 (es) | 2007-12-01 |
| EP1453863A1 (de) | 2004-09-08 |
| AU2002353732A1 (en) | 2003-06-17 |
| KR20050044632A (ko) | 2005-05-12 |
| JP2005511803A (ja) | 2005-04-28 |
| EP1453863B1 (de) | 2007-04-25 |
| CN1599756A (zh) | 2005-03-23 |
| SE0104047L (sv) | 2003-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |