CN1980876B - 从制备双酚a的含苯酚流中分离苯酚的方法 - Google Patents
从制备双酚a的含苯酚流中分离苯酚的方法 Download PDFInfo
- Publication number
- CN1980876B CN1980876B CN2005800225273A CN200580022527A CN1980876B CN 1980876 B CN1980876 B CN 1980876B CN 2005800225273 A CN2005800225273 A CN 2005800225273A CN 200580022527 A CN200580022527 A CN 200580022527A CN 1980876 B CN1980876 B CN 1980876B
- Authority
- CN
- China
- Prior art keywords
- phenol
- stream
- bottom product
- bpa
- fed
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 238000000034 method Methods 0.000 title claims abstract description 27
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title abstract description 60
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000004821 distillation Methods 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 238000000926 separation method Methods 0.000 claims abstract description 18
- 230000002378 acidificating effect Effects 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 34
- 238000005516 engineering process Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 9
- 238000006317 isomerization reaction Methods 0.000 claims description 8
- 241000282326 Felis catus Species 0.000 claims description 6
- 230000014759 maintenance of location Effects 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 description 25
- 239000002253 acid Substances 0.000 description 18
- 238000005336 cracking Methods 0.000 description 16
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000007599 discharging Methods 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 230000001351 cycling effect Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- -1 sulfhydryl compound Chemical class 0.000 description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000007848 Bronsted acid Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- YQDJQYVIHZYJSE-UHFFFAOYSA-N 1-phenyl-2,3-dihydroindene-1,2-diol Chemical compound OC1CC2=CC=CC=C2C1(O)C1=CC=CC=C1 YQDJQYVIHZYJSE-UHFFFAOYSA-N 0.000 description 1
- MLCQXUZZAXKTSG-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 MLCQXUZZAXKTSG-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- JGDWYKQLFQQIDH-UHFFFAOYSA-N 2-phenyl-3,4-dihydrochromen-2-ol Chemical compound C1CC2=CC=CC=C2OC1(O)C1=CC=CC=C1 JGDWYKQLFQQIDH-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- XDTRNDKYILNOAP-UHFFFAOYSA-N phenol;propan-2-one Chemical compound CC(C)=O.OC1=CC=CC=C1 XDTRNDKYILNOAP-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
M(1)[t/h] | X[-] | c[%] | T(11)[℃] | C(5)[Gew.-%] | M(5)[t/h] | Y[-] | M(9)[t/h] | M(8)[t/h] | τ(11)[h] | |
实施例1<sup>1)2)</sup> | 2.75 | 0.65 | 0.06 | 205 | 99.88 | 2.19 | 1.22 | 0.56 | 3.10 | 19.4 |
实施例2<sup>1)2)</sup> | 2.40 | 0.50 | 0.06 | 210 | 99.91 | 1.72 | 1.43 | 0.68 | 2.95 | 20.3 |
对比实施例3<sup>1)2)</sup> | 2.65 | 0.62 | 0.06 | 180 | 99.75 | 1.69 | 1.03 | 0.96 | 2.80 | 21.4 |
对比实施例4<sup>1)2)</sup> | 2.80 | 0.59 | 0.0 | 205 | 99.87 | 1.60 | 0.97 | 1.20 | 3.05 | 19.7 |
对比实施例5<sup>1)2)</sup> | 2.75 | 0.63 | 0.05 | 200 | 99.89 | 1.82 | 1.05 | 0.93 | 0.5 | 120.0 |
对比实施例6<sup>3)2)</sup> | 2.90 | 0.62 | 0.06 | 205 | 96.25 | 2.28 | 1.27 | 0.62 | 3.2 | 18.8 |
对比实施例7<sup>1)4)</sup> | 2.90 | 0.58 | 0.05 | 205 | 99.58 | 1.70 | 1.01 | 1.20 | 3.2 | 0 |
Claims (5)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004032232.5 | 2004-07-02 | ||
DE102004032232A DE102004032232A1 (de) | 2004-07-02 | 2004-07-02 | Verfahren zur Abtrennung von Phenol aus phenolhaltigen Strömen aus der Herstellung von Bisphenol A |
PCT/EP2005/006603 WO2006002788A1 (de) | 2004-07-02 | 2005-06-18 | Verfahren zur abtrennung von phenol aus phenolhaltigen strömen aus der herstellung von bisphenol a |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1980876A CN1980876A (zh) | 2007-06-13 |
CN1980876B true CN1980876B (zh) | 2010-12-01 |
Family
ID=35063346
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2005800225273A Expired - Fee Related CN1980876B (zh) | 2004-07-02 | 2005-06-18 | 从制备双酚a的含苯酚流中分离苯酚的方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7301056B2 (zh) |
EP (1) | EP1765752B1 (zh) |
JP (1) | JP2008504320A (zh) |
KR (1) | KR20070028473A (zh) |
CN (1) | CN1980876B (zh) |
DE (1) | DE102004032232A1 (zh) |
ES (1) | ES2550008T3 (zh) |
RU (1) | RU2401255C2 (zh) |
WO (1) | WO2006002788A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102171172B (zh) * | 2008-10-28 | 2013-08-21 | 巴杰许可有限责任公司 | 从bpa废物流回收苯酚的方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8431749B2 (en) | 2011-06-06 | 2013-04-30 | Badger Licensing Llc | Recovery of phenol and acetone from bisphenol-A streams |
TWI557103B (zh) | 2011-06-06 | 2016-11-11 | 貝吉特許有限責任公司 | 雙酚-a殘留物流份之處理 |
CN104056464B (zh) * | 2014-07-02 | 2015-08-05 | 南通星辰合成材料有限公司 | 以蒸汽喷射与液环真空泵实现双酚a汽提单元真空的方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6015648B2 (ja) * | 1980-09-29 | 1985-04-20 | アイシン化工株式会社 | シエルモ−ルド用樹脂の製造方法 |
DE59500998D1 (de) | 1994-05-02 | 1998-01-02 | Ferag Ag | Verfahren und Vorrichtung zum Speichern von Zuschnitten |
DE19529855A1 (de) | 1995-08-14 | 1997-02-20 | Bayer Ag | Verfahren zur Reinigung von Bisphenol |
US5783733A (en) | 1996-06-13 | 1998-07-21 | General Electric Company | Process for manufacture of bisphenol |
US6133486A (en) * | 1998-12-30 | 2000-10-17 | General Electric Company | Phenol recovery from BPA process waste streams |
-
2004
- 2004-07-02 DE DE102004032232A patent/DE102004032232A1/de not_active Withdrawn
-
2005
- 2005-06-18 ES ES05756999.8T patent/ES2550008T3/es active Active
- 2005-06-18 JP JP2007518497A patent/JP2008504320A/ja not_active Withdrawn
- 2005-06-18 EP EP05756999.8A patent/EP1765752B1/de active Active
- 2005-06-18 WO PCT/EP2005/006603 patent/WO2006002788A1/de active Application Filing
- 2005-06-18 CN CN2005800225273A patent/CN1980876B/zh not_active Expired - Fee Related
- 2005-06-18 RU RU2007103892/04A patent/RU2401255C2/ru not_active IP Right Cessation
- 2005-06-18 KR KR1020067027776A patent/KR20070028473A/ko not_active Application Discontinuation
- 2005-06-28 US US11/168,025 patent/US7301056B2/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102171172B (zh) * | 2008-10-28 | 2013-08-21 | 巴杰许可有限责任公司 | 从bpa废物流回收苯酚的方法 |
Also Published As
Publication number | Publication date |
---|---|
JP2008504320A (ja) | 2008-02-14 |
DE102004032232A1 (de) | 2006-01-19 |
RU2007103892A (ru) | 2008-08-10 |
EP1765752A1 (de) | 2007-03-28 |
WO2006002788A1 (de) | 2006-01-12 |
US20060004234A1 (en) | 2006-01-05 |
ES2550008T3 (es) | 2015-11-03 |
CN1980876A (zh) | 2007-06-13 |
EP1765752B1 (de) | 2015-08-26 |
KR20070028473A (ko) | 2007-03-12 |
US7301056B2 (en) | 2007-11-27 |
RU2401255C2 (ru) | 2010-10-10 |
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