JP2004502003A5 - - Google Patents
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- Publication number
- JP2004502003A5 JP2004502003A5 JP2002505879A JP2002505879A JP2004502003A5 JP 2004502003 A5 JP2004502003 A5 JP 2004502003A5 JP 2002505879 A JP2002505879 A JP 2002505879A JP 2002505879 A JP2002505879 A JP 2002505879A JP 2004502003 A5 JP2004502003 A5 JP 2004502003A5
- Authority
- JP
- Japan
- Prior art keywords
- catechol
- gallate
- cation
- contribute
- substituted
- 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
- 150000001768 cations Chemical class 0.000 description 7
- 150000001450 anions Chemical group 0.000 description 5
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 5
- 239000003446 ligand Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- -1 alcohol carboxylic acid esters Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 description 2
- 229940074391 gallic acid Drugs 0.000 description 2
- 235000004515 gallic acid Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- FBSFWRHWHYMIOG-UHFFFAOYSA-N methyl 3,4,5-trihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=C(O)C(O)=C1 FBSFWRHWHYMIOG-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000003624 transition metals Chemical group 0.000 description 2
- 0 *c(c(*)c(c(*)c1O)I)c1O Chemical compound *c(c(*)c(c(*)c1O)I)c1O 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- XIROXSOOOAZHLL-UHFFFAOYSA-N 2',3',4'-Trihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C(O)=C1O XIROXSOOOAZHLL-UHFFFAOYSA-N 0.000 description 1
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 1
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- YHKWFDPEASWKFQ-UHFFFAOYSA-N 3-nitrobenzene-1,2-diol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1O YHKWFDPEASWKFQ-UHFFFAOYSA-N 0.000 description 1
- XJNPNXSISMKQEX-UHFFFAOYSA-N 4-nitrocatechol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1O XJNPNXSISMKQEX-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004262 Ethyl gallate Substances 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- XOPOEBVTQYAOSV-UHFFFAOYSA-N butyl 3,4,5-trihydroxybenzoate Chemical compound CCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 XOPOEBVTQYAOSV-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 235000019277 ethyl gallate Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- IBKQQKPQRYUGBJ-UHFFFAOYSA-N methyl gallate Natural products CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000005463 sulfonylimide group Chemical group 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/602,855 US6482868B1 (en) | 1998-12-31 | 2000-06-26 | Accelerators useful for energy polymerizable compositions |
| US09/602,855 | 2000-06-26 | ||
| PCT/US2000/029965 WO2002000758A1 (en) | 2000-06-26 | 2000-10-31 | Accelerators useful for energy polymerizable compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004502003A JP2004502003A (ja) | 2004-01-22 |
| JP2004502003A5 true JP2004502003A5 (enExample) | 2008-01-31 |
| JP4833491B2 JP4833491B2 (ja) | 2011-12-07 |
Family
ID=24413059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002505879A Expired - Fee Related JP4833491B2 (ja) | 2000-06-26 | 2000-10-31 | エネルギー重合性組成物に有用な促進剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6482868B1 (enExample) |
| EP (1) | EP1299448B1 (enExample) |
| JP (1) | JP4833491B2 (enExample) |
| KR (1) | KR100679000B1 (enExample) |
| AT (1) | ATE301684T1 (enExample) |
| AU (1) | AU2001214467A1 (enExample) |
| DE (1) | DE60021922T2 (enExample) |
| WO (1) | WO2002000758A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6635689B1 (en) * | 2000-06-26 | 2003-10-21 | 3M Innovative Properties Company | Accelerators for cationic polymerization catalyzed by iron-based catalysts |
| US20050256230A1 (en) * | 2002-04-01 | 2005-11-17 | Hiroaki Yamaguchi | Cationic polymerizable adhesive composition and anisotropically electroconductive adhesive composition |
| US20050126697A1 (en) * | 2003-12-11 | 2005-06-16 | International Business Machines Corporation | Photochemically and thermally curable adhesive formulations |
| US8501886B2 (en) * | 2003-12-22 | 2013-08-06 | Dow Global Technologies Llc | Accelerated organoborane amine complex initiated polymerizable compositions |
| JP2007515547A (ja) * | 2003-12-22 | 2007-06-14 | ダウ グローバル テクノロジーズ インコーポレイティド | 促進されたオルガノボランアミン錯体開始重合性組成物 |
| JP4574993B2 (ja) | 2004-01-16 | 2010-11-04 | オリンパス株式会社 | 病変検出システム |
| US20050250929A1 (en) * | 2004-05-10 | 2005-11-10 | 3M Innovative Properties Company | Ferrocenium-derived catalyst for cationically polymerizable monomers |
| JP5383988B2 (ja) * | 2007-07-30 | 2014-01-08 | 花王株式会社 | 縮重合反応用助触媒 |
| CN101977919B (zh) * | 2008-03-24 | 2014-04-23 | 昭和电工株式会社 | 环氧化合物及其制造方法 |
| US8399099B1 (en) * | 2008-05-23 | 2013-03-19 | Henkel Ireland Limited | Coating compositions |
| US20090288771A1 (en) * | 2008-05-23 | 2009-11-26 | Loctite (R&D) Limited | Surface-promoted cure of one-part radically curable compositions |
| US20090288770A1 (en) * | 2008-05-23 | 2009-11-26 | Loctite (R&D) Limited | Surface-promoted cure of one-part cationically curable compositions |
| WO2010094634A1 (en) | 2009-02-17 | 2010-08-26 | Loctite (R & D) Limited | Cationically curable compositions and a primer therefor |
| JP5684275B2 (ja) * | 2010-09-24 | 2015-03-11 | 電気化学工業株式会社 | エネルギー線硬化性樹脂組成物とそれを用いた接着剤及び硬化体 |
| US8816211B2 (en) * | 2011-02-14 | 2014-08-26 | Eastman Kodak Company | Articles with photocurable and photocured compositions |
| CN103289072A (zh) * | 2013-05-22 | 2013-09-11 | 苏州志向纺织科研股份有限公司 | 一种含二茂铁衍生物的燃速催化剂 |
| CN103435658B (zh) * | 2013-08-24 | 2016-04-27 | 北京化工大学 | 一种单宁酸铑配位催化剂的制备及对丁腈橡胶加氢应用 |
| MX388803B (es) * | 2014-03-07 | 2025-03-20 | Henkel Ag & Co Kgaa | Sistemas de resina epoxi fotocurable. |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3907706A (en) | 1973-07-06 | 1975-09-23 | Minnesota Mining & Mfg | Latent catalyst systems for cationically polymerizable materials |
| US4297458A (en) | 1980-07-14 | 1981-10-27 | General Electric Company | Curable epoxy resins |
| DE3369398D1 (en) | 1982-05-19 | 1987-02-26 | Ciba Geigy Ag | Curable compositions containing metallocen complexes, activated primers obtained therefrom and their use |
| US4518676A (en) | 1982-09-18 | 1985-05-21 | Ciba Geigy Corporation | Photopolymerizable compositions containing diaryliodosyl salts |
| US5191101A (en) | 1982-11-22 | 1993-03-02 | Minnesota Mining And Manufacturing Company | Energy polymerizable compositions containing organometallic initiators |
| US5089536A (en) | 1982-11-22 | 1992-02-18 | Minnesota Mining And Manufacturing Company | Energy polmerizable compositions containing organometallic initiators |
| US5073476A (en) | 1983-05-18 | 1991-12-17 | Ciba-Geigy Corporation | Curable composition and the use thereof |
| EP0152377B1 (de) | 1984-02-10 | 1987-12-09 | Ciba-Geigy Ag | Härtbare Zusammensetzung und deren Verwendung |
| US4503211A (en) | 1984-05-31 | 1985-03-05 | Minnesota Mining And Manufacturing Co. | Epoxy resin curing agent, process and composition |
| JPS6136302A (ja) | 1984-07-30 | 1986-02-21 | Toshiba Corp | 光重合性組成物 |
| US4603182A (en) * | 1984-10-05 | 1986-07-29 | General Electric Company | Low viscosity epoxy resin compositions |
| US4677137A (en) | 1985-05-31 | 1987-06-30 | Minnesota Mining And Manufacturing Company | Supported photoinitiator |
| JPS6245617A (ja) * | 1985-08-23 | 1987-02-27 | Matsushita Electric Works Ltd | エポキシ樹脂硬化促進剤 |
| US4788235A (en) | 1987-11-23 | 1988-11-29 | Minnesota Mining And Manufacturing Company | Phosphite modified epoxy resin |
| DE3814876A1 (de) | 1988-05-02 | 1989-11-16 | Henkel Kgaa | Lichtinduziert dunkelhaertende klebstoffe |
| JP2841810B2 (ja) * | 1990-09-27 | 1998-12-24 | 関西ペイント株式会社 | 有機容剤形熱硬化性塗料組成物 |
| CA2082258A1 (en) | 1990-04-23 | 1991-10-24 | Michael C. Palazzotto | Energy curable cationically and free-radically polymerizable pressure sensitive compositions |
| US5059701A (en) | 1990-09-20 | 1991-10-22 | Minnesota Mining And Manufacturing Company | Methods for preparation of cyclopentadienyliron (II) arenes |
| US5252694A (en) | 1992-01-22 | 1993-10-12 | Minnesota Mining And Manufacturing Company | Energy-polymerization adhesive, coating, film and process for making the same |
| US5212210A (en) | 1992-03-18 | 1993-05-18 | Minnesota Mining And Manufacturing Company | Energy curable compositions having improved cure speeds |
| US5494943A (en) | 1993-06-16 | 1996-02-27 | Minnesota Mining And Manufacturing Company | Stabilized cationically-curable compositions |
| US5453450A (en) * | 1993-06-16 | 1995-09-26 | Minnesota Mining And Manufacturing Company | Stabilized curable adhesives |
| US5362421A (en) | 1993-06-16 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Electrically conductive adhesive compositions |
| DE4340949A1 (de) * | 1993-12-01 | 1995-06-08 | Thera Ges Fuer Patente | Lichtinitiiert kationisch härtende Epoxidmasse und ihre Verwendung |
| DE4421623A1 (de) * | 1994-06-21 | 1996-01-04 | Thera Ges Fuer Patente | Mehrkomponentige, kationisch härtende Epoxidmassen und deren Verwendung sowie Verfahren zur Herstellung gehärteter Massen |
| DE69520222T2 (de) | 1994-10-31 | 2001-08-23 | Minnesota Mining And Mfg. Co., Saint Paul | Mit sichtbarem licht härtbares epoxysystem mit verbesserter härtungstiefe |
| US5554664A (en) | 1995-03-06 | 1996-09-10 | Minnesota Mining And Manufacturing Company | Energy-activatable salts with fluorocarbon anions |
| DE19534664A1 (de) | 1995-09-19 | 1997-03-20 | Thera Ges Fuer Patente | Lichtinitiiert kationisch härtende, dauerflexible Epoxidharzmasse und ihre Verwendung |
| JPH09325479A (ja) | 1996-05-31 | 1997-12-16 | Hitachi Chem Co Ltd | 感光性組成物、感光材料、レリーフパターンの製造法及びポリイミドパターンの製造法 |
| US6265459B1 (en) | 1998-12-31 | 2001-07-24 | 3M Innovative Properties Company | Accelerators useful for energy polymerizable compositions |
| US6133335A (en) | 1998-12-31 | 2000-10-17 | 3M Innovative Properties Company | Photo-polymerizable compositions and articles made therefrom |
-
2000
- 2000-06-26 US US09/602,855 patent/US6482868B1/en not_active Expired - Lifetime
- 2000-10-31 KR KR1020027017601A patent/KR100679000B1/ko not_active Expired - Fee Related
- 2000-10-31 AT AT00976732T patent/ATE301684T1/de not_active IP Right Cessation
- 2000-10-31 JP JP2002505879A patent/JP4833491B2/ja not_active Expired - Fee Related
- 2000-10-31 EP EP00976732A patent/EP1299448B1/en not_active Expired - Lifetime
- 2000-10-31 WO PCT/US2000/029965 patent/WO2002000758A1/en not_active Ceased
- 2000-10-31 AU AU2001214467A patent/AU2001214467A1/en not_active Abandoned
- 2000-10-31 DE DE60021922T patent/DE60021922T2/de not_active Expired - Lifetime
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