JP5317066B2 - ビスシトラコンイミド、ビスイタコンイミド、および／またはシトラコンイミド−イタコンイミドを含んでいる組成物 - Google Patents
ビスシトラコンイミド、ビスイタコンイミド、および／またはシトラコンイミド−イタコンイミドを含んでいる組成物 Download PDFInfo
- Publication number
- JP5317066B2 JP5317066B2 JP2009510393A JP2009510393A JP5317066B2 JP 5317066 B2 JP5317066 B2 JP 5317066B2 JP 2009510393 A JP2009510393 A JP 2009510393A JP 2009510393 A JP2009510393 A JP 2009510393A JP 5317066 B2 JP5317066 B2 JP 5317066B2
- Authority
- JP
- Japan
- Prior art keywords
- biscitraconimide
- itaconimide
- weight
- composition
- citraconimide
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 62
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 24
- 229920003192 poly(bis maleimide) Polymers 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 4
- -1 m-xylylene Chemical group 0.000 claims description 15
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 13
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000000835 fiber Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- FKAWETHEYBZGSR-UHFFFAOYSA-N 3-methylidenepyrrolidine-2,5-dione Chemical compound C=C1CC(=O)NC1=O FKAWETHEYBZGSR-UHFFFAOYSA-N 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 5
- AVEDGBJBUHVIPC-UHFFFAOYSA-N 3-[2-[3-[2-(2,5-dioxopyrrol-3-yl)ethyl]phenyl]ethyl]pyrrole-2,5-dione Chemical group O=C1NC(=O)C(CCC=2C=C(CCC=3C(NC(=O)C=3)=O)C=CC=2)=C1 AVEDGBJBUHVIPC-UHFFFAOYSA-N 0.000 claims description 4
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 claims description 3
- JYFJKHAXRTTXFL-UHFFFAOYSA-N 3-[2-[3-[2-(2,5-dioxopyrrolidin-3-ylidene)ethyl]phenyl]ethylidene]pyrrolidine-2,5-dione Chemical compound O=C1NC(=O)CC1=CCC1=CC=CC(CC=C2C(NC(=O)C2)=O)=C1 JYFJKHAXRTTXFL-UHFFFAOYSA-N 0.000 claims description 2
- GQEAKMWCKUPCFM-UHFFFAOYSA-N pyrrole-2,5-dione hydrobromide Chemical compound C1=CC(=O)NC1=O.Br GQEAKMWCKUPCFM-UHFFFAOYSA-N 0.000 claims 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 15
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 238000006384 oligomerization reaction Methods 0.000 description 7
- 239000011952 anionic catalyst Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 238000011993 High Performance Size Exclusion Chromatography Methods 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 229930188620 butyrolactone Natural products 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- CTDOPUVVTOMREJ-UHFFFAOYSA-N 1,3-dimethylidenecyclohexane Chemical compound C=C1CCCC(=C)C1 CTDOPUVVTOMREJ-UHFFFAOYSA-N 0.000 description 1
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical class OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 1
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 1
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003733 fiber-reinforced composite Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Reinforced Plastic Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06114173 | 2006-05-18 | ||
| EP06114173.5 | 2006-05-18 | ||
| US81065606P | 2006-06-05 | 2006-06-05 | |
| US60/810,656 | 2006-06-05 | ||
| PCT/EP2007/054104 WO2007134948A2 (en) | 2006-05-18 | 2007-04-26 | Compositions comprising biscitraconimide, bisitaconimide, and/or citraconimido-itaconimide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010505966A JP2010505966A (ja) | 2010-02-25 |
| JP2010505966A5 JP2010505966A5 (https=) | 2010-06-17 |
| JP5317066B2 true JP5317066B2 (ja) | 2013-10-16 |
Family
ID=38623979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009510393A Expired - Fee Related JP5317066B2 (ja) | 2006-05-18 | 2007-04-26 | ビスシトラコンイミド、ビスイタコンイミド、および／またはシトラコンイミド−イタコンイミドを含んでいる組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8048489B2 (https=) |
| EP (1) | EP2018401B1 (https=) |
| JP (1) | JP5317066B2 (https=) |
| AT (1) | ATE456586T1 (https=) |
| DE (1) | DE602007004593D1 (https=) |
| DK (1) | DK2018401T3 (https=) |
| WO (1) | WO2007134948A2 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5497660B2 (ja) * | 2007-12-17 | 2014-05-21 | ランクセス・ドイチュランド・ゲーエムベーハー | 硬化系およびそれによって得られるコーティング |
| NL1037120C2 (en) | 2009-07-15 | 2011-01-18 | Holland Novochem Technical Coatings B V | Heat-resistant, chemical resistant, room temperature curable, solvent-free resin compositions to apply as protective coating. |
| NL1038104C2 (en) * | 2010-07-14 | 2012-01-23 | Holland Novochem Technical Coatings B V | Heat-resistant, chemical resistant, room temperature curable, solvent-free resin compositions to apply as protective coating. |
| TWI454490B (zh) | 2011-12-30 | 2014-10-01 | Ind Tech Res Inst | 共聚物及其形成方法 |
| IL299364B2 (en) | 2020-06-24 | 2024-04-01 | Arxada Ag | Innovative compositions with improved properties |
| JP7451058B2 (ja) | 2021-03-23 | 2024-03-18 | 信越化学工業株式会社 | 熱硬化性シトラコンイミド樹脂組成物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2057089T5 (es) * | 1989-07-11 | 1996-03-16 | Akzo Nobel Nv | (co)polimero de biscitraconimida y procedimiento para curar biscitraconimidas con un catalizador anionico. |
| US5198515A (en) * | 1989-08-03 | 1993-03-30 | Akzo N.V. | Biscitraconimide copolymers with olefinically unsaturated materials |
| DE69200964T2 (de) * | 1991-01-16 | 1995-07-27 | Akzo Nv | Citrazonimidcopolymerisate und ihre Härtung mit anionischem Katalysator. |
| US5194567A (en) * | 1991-04-08 | 1993-03-16 | Dayco Products, Inc. | Reaction injection moldable (RIM) thermoset polyimide elastomers |
| US5230666A (en) * | 1991-04-08 | 1993-07-27 | Dayco Products, Inc. | Reaction injection moldable (RIM) thermoset polyimide elastomers |
| US20060223950A1 (en) * | 2003-08-27 | 2006-10-05 | Flexsys B.V. | Process for enhancing the melt strength of polypropylene |
-
2007
- 2007-04-26 DK DK07728559.1T patent/DK2018401T3/da active
- 2007-04-26 WO PCT/EP2007/054104 patent/WO2007134948A2/en not_active Ceased
- 2007-04-26 DE DE602007004593T patent/DE602007004593D1/de active Active
- 2007-04-26 JP JP2009510393A patent/JP5317066B2/ja not_active Expired - Fee Related
- 2007-04-26 EP EP07728559A patent/EP2018401B1/en not_active Not-in-force
- 2007-04-26 AT AT07728559T patent/ATE456586T1/de not_active IP Right Cessation
- 2007-04-26 US US12/301,183 patent/US8048489B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2018401B1 (en) | 2010-01-27 |
| ATE456586T1 (de) | 2010-02-15 |
| WO2007134948A2 (en) | 2007-11-29 |
| EP2018401A2 (en) | 2009-01-28 |
| DE602007004593D1 (de) | 2010-03-18 |
| WO2007134948A3 (en) | 2009-01-22 |
| US8048489B2 (en) | 2011-11-01 |
| DK2018401T3 (da) | 2010-05-03 |
| JP2010505966A (ja) | 2010-02-25 |
| US20090186158A1 (en) | 2009-07-23 |
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