JP2013516517A5 - - Google Patents
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- Publication number
- JP2013516517A5 JP2013516517A5 JP2012547153A JP2012547153A JP2013516517A5 JP 2013516517 A5 JP2013516517 A5 JP 2013516517A5 JP 2012547153 A JP2012547153 A JP 2012547153A JP 2012547153 A JP2012547153 A JP 2012547153A JP 2013516517 A5 JP2013516517 A5 JP 2013516517A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- aralkyl
- aryl
- formula
- alkylene
- 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.)
- Granted
Links
- 125000002947 alkylene group Chemical group 0.000 claims description 52
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 48
- 150000001412 amines Chemical class 0.000 claims description 37
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 35
- -1 oxalate compound Chemical class 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
- 229920001577 copolymer Polymers 0.000 claims description 20
- 229920001296 polysiloxane Polymers 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 239000010702 perfluoropolyether Substances 0.000 claims description 18
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 18
- 125000000732 arylene group Chemical group 0.000 claims description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 238000006482 condensation reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 5
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000003901 oxalic acid esters Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- 229920001875 Ebonite Polymers 0.000 description 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- YMTUYHWOWDFXOX-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl) oxalate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OC(=O)C(=O)OC1=C(F)C(F)=C(F)C(F)=C1F YMTUYHWOWDFXOX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- ULOZDEVJRTYKFE-UHFFFAOYSA-N diphenyl oxalate Chemical compound C=1C=CC=CC=1OC(=O)C(=O)OC1=CC=CC=C1 ULOZDEVJRTYKFE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- CIYGMWIAXRMHQS-UHFFFAOYSA-N ditert-butyl oxalate Chemical compound CC(C)(C)OC(=O)C(=O)OC(C)(C)C CIYGMWIAXRMHQS-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- WHIVNJATOVLWBW-SNAWJCMRSA-N methylethyl ketone oxime Chemical compound CC\C(C)=N\O WHIVNJATOVLWBW-SNAWJCMRSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- GEVPIWPYWJZSPR-UHFFFAOYSA-N tcpo Chemical compound ClC1=CC(Cl)=CC(Cl)=C1OC(=O)C(=O)OC1=C(Cl)C=C(Cl)C=C1Cl GEVPIWPYWJZSPR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29103309P | 2009-12-30 | 2009-12-30 | |
| US61/291,033 | 2009-12-30 | ||
| PCT/US2010/061787 WO2011082063A1 (en) | 2009-12-30 | 2010-12-22 | Copolymers with perfluorpolyether segment and polydiorganosiloxane segment |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013516517A JP2013516517A (ja) | 2013-05-13 |
| JP2013516517A5 true JP2013516517A5 (https=) | 2017-03-23 |
| JP6196775B2 JP6196775B2 (ja) | 2017-09-13 |
Family
ID=43530394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012547153A Expired - Fee Related JP6196775B2 (ja) | 2009-12-30 | 2010-12-22 | ペルフルオロポリエーテルセグメント及びポリジオルガノシロキサンセグメントを有するコポリマー |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8552124B2 (https=) |
| EP (1) | EP2519564B1 (https=) |
| JP (1) | JP6196775B2 (https=) |
| CN (1) | CN102695745B (https=) |
| WO (1) | WO2011082063A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102770478B (zh) * | 2009-12-30 | 2014-03-12 | 3M创新有限公司 | 具有全氟聚醚链段和多个氨基乙二酰胺基的共聚物 |
| EP2519559B1 (en) * | 2009-12-30 | 2015-07-15 | 3M Innovative Properties Company | Perfluoropolyether-containing compounds with oxalylamino groups |
| WO2011082069A1 (en) | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Methods of making polydiorganosiloxane polyoxamide copolymers |
| US10377857B2 (en) | 2013-12-24 | 2019-08-13 | Solvay Specialty Polymers Italy S.P.A. | Polyamides modified with (per)fluoropolyether segments |
| WO2015200003A1 (en) * | 2014-06-23 | 2015-12-30 | 3M Innovative Properties Company | Silicon-containing polymer and method of making a silicon-containing polymer |
| CN106146820B (zh) * | 2016-07-13 | 2018-02-13 | 天津科技大学 | 全氟碘制备单端z型全氟聚醚硅氧烷的方法 |
| JP2019524971A (ja) * | 2016-08-31 | 2019-09-05 | ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． | （ペル）フルオロポリエーテル単位とポリ（オルガノシロキサン）単位とを含むポリアミド |
| WO2018184695A1 (de) * | 2017-04-07 | 2018-10-11 | Wacker Chemie Ag | Verfahren zur herstellung von oxamid-funktionellen siloxanen |
| US11780967B2 (en) * | 2018-07-30 | 2023-10-10 | Wacker Chemie Ag | Process for preparing oxamide-functional siloxanes |
| JP7700226B2 (ja) * | 2020-10-13 | 2025-06-30 | ワッカー ケミー アクチエンゲゼルシャフト | オキサラトポリエーテルで予備架橋したアミノ官能化オルガノポリシロキサンの水性分散液 |
| CN119095898A (zh) * | 2022-04-27 | 2024-12-06 | 大金工业株式会社 | 含氟代聚醚基的氧亚烷基酰胺化合物 |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2343808A (en) | 1939-05-17 | 1944-03-07 | Schlack Paul | Nitrogenous condensation products |
| US3250807A (en) | 1963-08-23 | 1966-05-10 | Du Pont | Dicarboxylic acids of fluorocarbon ethers and fluorides, esters, amides and salts thereof |
| NL148300B (nl) | 1964-01-02 | 1976-01-15 | Edison Soc | Werkwijze ter bereiding van polyoxyperfluormethylenen. |
| US3442942A (en) | 1964-04-09 | 1969-05-06 | Montedison Spa | Fluorinated oxygen containing acyl fluorides |
| NL6709067A (https=) | 1964-04-09 | 1968-01-08 | ||
| US3715378A (en) | 1967-02-09 | 1973-02-06 | Montedison Spa | Fluorinated peroxy polyether copolymers and method for preparing them from tetrafluoroethylene |
| US3485806A (en) | 1968-02-07 | 1969-12-23 | Ashland Oil Inc | Hydroxy substituted aminimides |
| US3810874A (en) | 1969-03-10 | 1974-05-14 | Minnesota Mining & Mfg | Polymers prepared from poly(perfluoro-alkylene oxide) compounds |
| US4085137A (en) * | 1969-03-10 | 1978-04-18 | Minnesota Mining And Manufacturing Company | Poly(perfluoroalkylene oxide) derivatives |
| US3728311A (en) | 1971-12-16 | 1973-04-17 | Du Pont | Polyureas,polyurethanes and polyamides based on a tetra-oxo diamine component |
| US3890269A (en) | 1972-08-11 | 1975-06-17 | Stauffer Chemical Co | Process for preparing aminofunctional polysiloxane polymers |
| US4119615A (en) * | 1976-09-24 | 1978-10-10 | Texaco Development Corporation | Thermoplastic adhesive polyoxamide from polyoxypropylene polyamine |
| US4684728A (en) | 1979-01-12 | 1987-08-04 | Bayer Aktiengesellschaft | Solubilizing biologically active compounds with reactive hydrogen atoms |
| US4472480A (en) * | 1982-07-02 | 1984-09-18 | Minnesota Mining And Manufacturing Company | Low surface energy liner of perfluoropolyether |
| US4647413A (en) * | 1983-12-27 | 1987-03-03 | Minnesota Mining And Manufacturing Company | Perfluoropolyether oligomers and polymers |
| US4565714B1 (en) | 1984-06-14 | 1999-06-29 | Minnesota Mining & Mfg | Low surface energy material |
| US4661577A (en) | 1985-10-01 | 1987-04-28 | General Electric Company | Aminofunctional polysiloxanes |
| US5214119A (en) | 1986-06-20 | 1993-05-25 | Minnesota Mining And Manufacturing Company | Block copolymer, method of making the same, dimaine precursors of the same, method of making such diamines and end products comprising the block copolymer |
| US5512650A (en) | 1986-06-20 | 1996-04-30 | Minnesota Mining And Manufacturing Company | Block copolymer, method of making the same, diamine precursors of the same, method of making such diamines and end products comprising the block copolymer |
| US5026890A (en) | 1988-05-20 | 1991-06-25 | General Electric Company | Method and intermediates for preparation of bis(aminoalkyl)polydiorganosiloxanes |
| US5093432A (en) | 1988-09-28 | 1992-03-03 | Exfluor Research Corporation | Liquid phase fluorination |
| US5266650A (en) | 1990-10-11 | 1993-11-30 | Minnesota Mining And Manufacturing Company | Curing fluorocarbon elastomers |
| JP2684130B2 (ja) | 1991-08-15 | 1997-12-03 | 信越化学工業株式会社 | アミノ基含有ポリシロキサンの製造方法 |
| JP2652304B2 (ja) * | 1992-06-17 | 1997-09-10 | 信越化学工業株式会社 | 含フッ素有機ケイ素化合物 |
| US5488142A (en) | 1993-10-04 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Fluorination in tubular reactor system |
| US5663127A (en) | 1994-07-29 | 1997-09-02 | Minnesota Mining And Manufacturing Company | Perfluoropolyether lubricating compositions |
| EP0822952B1 (en) | 1995-04-25 | 2003-07-23 | Minnesota Mining And Manufacturing Company | Polydiorganosiloxane oligourea segmented copolymers and a process for making same |
| US6355759B1 (en) | 1996-04-25 | 2002-03-12 | 3M Innovative Properties Company | Polydiorganosiloxane polyurea segmented copolymers and a process for making same |
| US6441118B2 (en) * | 1996-04-25 | 2002-08-27 | 3M Innovative Properties Company | Polydiorganosiloxane oligourea segmented copolymers and a process for making same |
| US6313335B1 (en) * | 1997-11-25 | 2001-11-06 | 3M Innovative Properties | Room temperature curable silane terminated and stable waterborne polyurethane dispersions which contain fluorine and/or silicone and low surface energy coatings prepared therefrom |
| JP3729687B2 (ja) | 1999-08-04 | 2005-12-21 | 株式会社巴川製紙所 | 反射防止材料 |
| ITMI20021734A1 (it) | 2002-08-01 | 2004-02-02 | Ausimont S P A Ora Solvay Solexis Spa | Processo per la preparazione di perfluoropolieteri con terminali aldeidici, alcolici, amminici mediante riduzione catalitica. |
| TWI293715B (en) | 2002-10-10 | 2008-02-21 | Sipix Imaging Inc | A method for inducing or enhancing the threshold of an electrophoretic display, an electrophoretic fluid and an electrophoretic display |
| US6923921B2 (en) | 2002-12-30 | 2005-08-02 | 3M Innovative Properties Company | Fluorinated polyether compositions |
| US20040266985A1 (en) | 2003-06-26 | 2004-12-30 | Jon Lee Howell | Nitrogenated perfluoropolyether composition |
| US20070149745A1 (en) | 2005-12-23 | 2007-06-28 | 3M Innovative Properties Company | Polydiorganosiloxane-containing materials with oxalylamino groups |
| US8067094B2 (en) | 2005-12-23 | 2011-11-29 | 3M Innovative Properties Company | Films including thermoplastic silicone block copolymers |
| US7371464B2 (en) | 2005-12-23 | 2008-05-13 | 3M Innovative Properties Company | Adhesive compositions |
| US7501184B2 (en) * | 2005-12-23 | 2009-03-10 | 3M Innovative Properties Company | Polydiorganosiloxane polyoxamide copolymers |
| PL1979432T3 (pl) | 2006-01-13 | 2019-05-31 | Chemours Co Fc Llc | Kompozycje dodatków do czynników chłodniczych zawierające perfluoropolietery |
| WO2008027594A2 (en) | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Phenol stabilizers for fluoroolefins |
| JP5008192B2 (ja) * | 2006-09-08 | 2012-08-22 | 信越化学工業株式会社 | パーフルオロポリエーテル−ポリオルガノシロキサン共重合体及びそれを含む表面処理剤 |
| EP2096133A4 (en) | 2006-12-11 | 2012-07-04 | Ube Industries | POLYAMIDE RESIN |
| US7745653B2 (en) | 2007-03-08 | 2010-06-29 | 3M Innovative Properties Company | Fluorochemical compounds having pendent silyl groups |
| US7335786B1 (en) | 2007-03-29 | 2008-02-26 | 3M Innovative Properties Company | Michael-adduct fluorochemical silanes |
| US8063166B2 (en) | 2007-06-22 | 2011-11-22 | 3M Innovative Properties Company | Polydiorganosiloxane polyamide copolymers having organic soft segments |
| US7705101B2 (en) * | 2007-06-22 | 2010-04-27 | 3M Innovative Properties Company | Branched polydiorganosiloxane polyamide copolymers |
| CN102770478B (zh) * | 2009-12-30 | 2014-03-12 | 3M创新有限公司 | 具有全氟聚醚链段和多个氨基乙二酰胺基的共聚物 |
| WO2011082069A1 (en) * | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Methods of making polydiorganosiloxane polyoxamide copolymers |
| EP2519529B1 (en) * | 2009-12-30 | 2015-10-21 | 3M Innovative Properties Company | Moisture-curable siloxane-containing and fluorocarbon-containing compounds and polymers formed therefrom |
| EP2519559B1 (en) * | 2009-12-30 | 2015-07-15 | 3M Innovative Properties Company | Perfluoropolyether-containing compounds with oxalylamino groups |
-
2010
- 2010-12-22 US US13/514,339 patent/US8552124B2/en not_active Expired - Fee Related
- 2010-12-22 JP JP2012547153A patent/JP6196775B2/ja not_active Expired - Fee Related
- 2010-12-22 CN CN2010800603102A patent/CN102695745B/zh not_active Expired - Fee Related
- 2010-12-22 EP EP10803322.6A patent/EP2519564B1/en not_active Not-in-force
- 2010-12-22 WO PCT/US2010/061787 patent/WO2011082063A1/en not_active Ceased
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