RU2468041C2 - Способ получения поликарбоната переэтерификацией в расплаве - Google Patents
Способ получения поликарбоната переэтерификацией в расплаве Download PDFInfo
- Publication number
- RU2468041C2 RU2468041C2 RU2009145793/04A RU2009145793A RU2468041C2 RU 2468041 C2 RU2468041 C2 RU 2468041C2 RU 2009145793/04 A RU2009145793/04 A RU 2009145793/04A RU 2009145793 A RU2009145793 A RU 2009145793A RU 2468041 C2 RU2468041 C2 RU 2468041C2
- Authority
- RU
- Russia
- Prior art keywords
- carbon atoms
- radical
- hydroxyphenyl
- bis
- linear
- Prior art date
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- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 94
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 title claims abstract description 86
- 238000005886 esterification reaction Methods 0.000 title abstract 2
- -1 dihydroxyaryl compound Chemical class 0.000 claims abstract description 164
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 239000000155 melt Substances 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 239000003112 inhibitor Substances 0.000 claims abstract description 23
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 79
- 150000001875 compounds Chemical class 0.000 claims description 45
- 230000008569 process Effects 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 238000005809 transesterification reaction Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001741 organic sulfur group Chemical group 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 4
- YFDUWSBGVPBWKF-UHFFFAOYSA-N Butyl salicylate Chemical compound CCCCOC(=O)C1=CC=CC=C1O YFDUWSBGVPBWKF-UHFFFAOYSA-N 0.000 claims description 3
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 3
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- 229940114055 beta-resorcylic acid Drugs 0.000 claims description 3
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 claims description 2
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 claims description 2
- XSVZEASGNTZBRQ-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfinylphenol Chemical class OC1=CC=CC=C1S(=O)C1=CC=CC=C1O XSVZEASGNTZBRQ-UHFFFAOYSA-N 0.000 claims description 2
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical class OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 claims description 2
- XUFUYOGWFZSHGE-UHFFFAOYSA-N 2-hydroxy-3,5-di(propan-2-yl)benzoic acid Chemical compound CC(C)C1=CC(C(C)C)=C(O)C(C(O)=O)=C1 XUFUYOGWFZSHGE-UHFFFAOYSA-N 0.000 claims description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 150000005205 dihydroxybenzenes Chemical class 0.000 claims description 2
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical class OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 claims 1
- KYGLCUAXJICESS-UHFFFAOYSA-N 2-[2,3-di(propan-2-yl)phenyl]phenol Chemical class CC(C)C1=CC=CC(C=2C(=CC=CC=2)O)=C1C(C)C KYGLCUAXJICESS-UHFFFAOYSA-N 0.000 claims 1
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
- 125000004673 propylcarbonyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
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- 238000001746 injection moulding Methods 0.000 description 33
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- 238000005259 measurement Methods 0.000 description 18
- 239000000758 substrate Substances 0.000 description 18
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 14
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- 239000007858 starting material Substances 0.000 description 13
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- 238000012360 testing method Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
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- 238000001704 evaporation Methods 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 7
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- XVHQFGPOVXTXPD-UHFFFAOYSA-M tetraphenylphosphanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XVHQFGPOVXTXPD-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229920006352 transparent thermoplastic Polymers 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008207 working material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
- G11B7/2534—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31667—Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200710022130 DE102007022130B4 (de) | 2007-05-11 | 2007-05-11 | Verfahren zur Herstellung von Polycarbonat nach dem Schmelzeumesterungsverfahren |
| DE102007022130.6 | 2007-05-11 | ||
| PCT/EP2008/003632 WO2008138517A2 (de) | 2007-05-11 | 2008-05-07 | Verfahren zur herstellung von polycarbonat nach dem schmelzeumesterungsverfahren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009145793A RU2009145793A (ru) | 2011-06-20 |
| RU2468041C2 true RU2468041C2 (ru) | 2012-11-27 |
Family
ID=39829383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009145793/04A RU2468041C2 (ru) | 2007-05-11 | 2008-05-07 | Способ получения поликарбоната переэтерификацией в расплаве |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7814626B2 (enExample) |
| EP (1) | EP2147038B1 (enExample) |
| JP (1) | JP5095815B2 (enExample) |
| KR (1) | KR20100016395A (enExample) |
| DE (1) | DE102007022130B4 (enExample) |
| ES (1) | ES2546382T3 (enExample) |
| RU (1) | RU2468041C2 (enExample) |
| TW (1) | TWI428367B (enExample) |
| WO (1) | WO2008138517A2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007052968A1 (de) * | 2007-11-07 | 2009-05-14 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polycarbonat nach dem Schmelzeumesterungsverfahren |
| US20090189321A1 (en) * | 2008-01-29 | 2009-07-30 | Dow Global Technologies Inc. | Thermoplastic composition and use for large parison blow molding applications |
| PL2558543T3 (pl) | 2010-04-16 | 2018-01-31 | Swimc Llc | Kompozycja powłokowa do wyrobów opakowaniowych i sposoby powlekania |
| CA2825377C (en) | 2011-02-07 | 2021-03-02 | Valspar Sourcing, Inc. | Coating compositions for containers and other articles and methods of coating |
| EP3483227B1 (en) | 2012-08-09 | 2020-12-16 | Swimc, LLC | Compositions for containers and other articles and methods of using same |
| EP2882792A4 (en) | 2012-08-09 | 2016-04-13 | Valspar Sourcing Inc | POLYCARBONATE |
| EP2882818B1 (en) | 2012-08-09 | 2020-05-06 | Swimc Llc | Stabilizer and coating compositions thereof |
| US10526502B2 (en) | 2012-08-09 | 2020-01-07 | Swimc Llc | Container coating system |
| CN104541210A (zh) | 2012-08-09 | 2015-04-22 | 威士伯采购公司 | 用于热响应记录材料的显影剂 |
| CN104582671B (zh) | 2012-08-09 | 2018-06-29 | 威士伯采购公司 | 牙科材料和制备方法 |
| KR101346516B1 (ko) * | 2013-01-18 | 2013-12-31 | 아주대학교산학협력단 | 염기 촉매를 이용하여 제조된 고분자량의 지방족 폴리카보네이트 |
| JP6746501B2 (ja) | 2014-04-14 | 2020-08-26 | ヴァルスパー・ソーシング・インコーポレーテッド | 容器及び他の物品のための組成物の調製方法並びにその使用方法 |
| JP6666193B2 (ja) * | 2015-04-22 | 2020-03-13 | 国立大学法人名古屋大学 | エステル交換反応用触媒及びそれを用いたエステル化合物の製造方法 |
| TWI614275B (zh) | 2015-11-03 | 2018-02-11 | Valspar Sourcing Inc | 用於製備聚合物的液體環氧樹脂組合物 |
| JP6972026B2 (ja) * | 2016-05-24 | 2021-11-24 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | 充填剤、カルボン酸およびそのグリセロールまたはジグリセロールエステルを含んでなるポリカーボネート組成物 |
| US20190388669A1 (en) * | 2017-01-30 | 2019-12-26 | Sabic Global Technologies B.V. | Microneedles made from polycarbonate-polycarbonate/polysiloxane copolymer compositions |
| CN108359231A (zh) * | 2018-02-09 | 2018-08-03 | 天津德迈特汽车零部件有限公司 | 塑料透镜及其制备方法 |
| CN109880074B (zh) * | 2019-02-25 | 2020-08-11 | 浙江欧威家具股份有限公司 | 聚碳酸酯的制备方法 |
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| US6403754B1 (en) * | 2001-01-29 | 2002-06-11 | General Electric Company | Optimization of polycarbonate preparation by transesterification |
| EP1427770B1 (en) * | 2001-09-07 | 2005-01-19 | General Electric Company | Process for the production of polycarbonate |
| RU2006108794A (ru) * | 2003-08-21 | 2006-09-10 | Мицубиси Кемикал Корпорейшн (Jp) | Способ получения ароматического поликарбоната |
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-
2007
- 2007-05-11 DE DE200710022130 patent/DE102007022130B4/de active Active
-
2008
- 2008-05-07 JP JP2010507825A patent/JP5095815B2/ja active Active
- 2008-05-07 WO PCT/EP2008/003632 patent/WO2008138517A2/de not_active Ceased
- 2008-05-07 EP EP08749353.2A patent/EP2147038B1/de active Active
- 2008-05-07 ES ES08749353.2T patent/ES2546382T3/es active Active
- 2008-05-07 RU RU2009145793/04A patent/RU2468041C2/ru not_active IP Right Cessation
- 2008-05-07 KR KR20097023431A patent/KR20100016395A/ko not_active Abandoned
- 2008-05-09 TW TW97117073A patent/TWI428367B/zh not_active IP Right Cessation
- 2008-05-09 US US12/117,798 patent/US7814626B2/en not_active Expired - Fee Related
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU219188A1 (ru) * | Т. Раудсепп , Э. К. Ярв | Способ получения поликарбонатов | ||
| US5696222A (en) * | 1995-09-19 | 1997-12-09 | Teijin Limited | Process for the production of polycarbonate |
| EP0980861A1 (en) * | 1997-04-04 | 2000-02-23 | Teijin Limited | Salicylic ester derivatives and process for producing the same |
| EP0982340A1 (en) * | 1998-03-17 | 2000-03-01 | Teijin Limited | Process for producing aromatic polycarbonate |
| US6300459B1 (en) * | 1998-03-17 | 2001-10-09 | Teijin Limited | Process for producing aromatic polycarbonate |
| US6403754B1 (en) * | 2001-01-29 | 2002-06-11 | General Electric Company | Optimization of polycarbonate preparation by transesterification |
| EP1427770B1 (en) * | 2001-09-07 | 2005-01-19 | General Electric Company | Process for the production of polycarbonate |
| RU2006108794A (ru) * | 2003-08-21 | 2006-09-10 | Мицубиси Кемикал Корпорейшн (Jp) | Способ получения ароматического поликарбоната |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080319156A1 (en) | 2008-12-25 |
| JP5095815B2 (ja) | 2012-12-12 |
| DE102007022130B4 (de) | 2015-02-19 |
| RU2009145793A (ru) | 2011-06-20 |
| EP2147038B1 (de) | 2015-07-01 |
| KR20100016395A (ko) | 2010-02-12 |
| TWI428367B (zh) | 2014-03-01 |
| EP2147038A2 (de) | 2010-01-27 |
| WO2008138517A3 (de) | 2009-02-12 |
| DE102007022130A1 (de) | 2008-11-13 |
| JP2010526920A (ja) | 2010-08-05 |
| ES2546382T3 (es) | 2015-09-23 |
| US7814626B2 (en) | 2010-10-19 |
| WO2008138517A2 (de) | 2008-11-20 |
| TW200911878A (en) | 2009-03-16 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20150508 |