CA2505977C - Process for the oxidative purification of terephthalic acid - Google Patents
Process for the oxidative purification of terephthalic acid Download PDFInfo
- Publication number
- CA2505977C CA2505977C CA002505977A CA2505977A CA2505977C CA 2505977 C CA2505977 C CA 2505977C CA 002505977 A CA002505977 A CA 002505977A CA 2505977 A CA2505977 A CA 2505977A CA 2505977 C CA2505977 C CA 2505977C
- Authority
- CA
- Canada
- Prior art keywords
- carboxylic acid
- solid liquid
- slurry composition
- zone
- composition
- 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
- 238000000034 method Methods 0.000 title claims abstract description 71
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 90
- 230000001590 oxidative effect Effects 0.000 title claims description 17
- 238000000746 purification Methods 0.000 title abstract description 7
- 239000002002 slurry Substances 0.000 claims abstract description 116
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 99
- 239000007787 solid Substances 0.000 claims abstract description 94
- 239000007788 liquid Substances 0.000 claims abstract description 93
- 238000006073 displacement reaction Methods 0.000 claims abstract description 64
- 239000012535 impurity Substances 0.000 claims abstract description 52
- 238000007254 oxidation reaction Methods 0.000 claims description 105
- 230000003647 oxidation Effects 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 64
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 19
- 238000002425 crystallisation Methods 0.000 claims description 18
- 230000008025 crystallization Effects 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 16
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 12
- PNVDDTCIZTWBNJ-UHFFFAOYSA-N 1-oxofluorene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2C3=CC=C(C(=O)O)C(=O)C3=CC2=C1 PNVDDTCIZTWBNJ-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 239000011572 manganese Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 11
- 239000000047 product Substances 0.000 description 91
- 239000002904 solvent Substances 0.000 description 26
- 239000012452 mother liquor Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000012855 volatile organic compound Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000010960 commercial process Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 aliphatic mono-carboxylic acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- KSOCVFUBQIXVDC-FMQUCBEESA-N p-azophenyltrimethylammonium Chemical compound C1=CC([N+](C)(C)C)=CC=C1\N=N\C1=CC=C([N+](C)(C)C)C=C1 KSOCVFUBQIXVDC-FMQUCBEESA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31529502A | 2002-12-09 | 2002-12-09 | |
| US10/315,295 | 2002-12-09 | ||
| US10/645,737 | 2003-08-21 | ||
| US10/645,737 US7074954B2 (en) | 2002-12-09 | 2003-08-21 | Process for the oxidative purification of terephthalic acid |
| PCT/US2003/038306 WO2004052821A1 (en) | 2002-12-09 | 2003-12-03 | Process for the oxidative purification of terephthalic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2505977A1 CA2505977A1 (en) | 2004-06-24 |
| CA2505977C true CA2505977C (en) | 2009-08-25 |
Family
ID=32511022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002505977A Expired - Fee Related CA2505977C (en) | 2002-12-09 | 2003-12-03 | Process for the oxidative purification of terephthalic acid |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7358392B2 (enExample) |
| EP (1) | EP1569888A1 (enExample) |
| JP (1) | JP2006509045A (enExample) |
| KR (1) | KR101004217B1 (enExample) |
| AU (1) | AU2003293251A1 (enExample) |
| BR (1) | BR0316462A (enExample) |
| CA (1) | CA2505977C (enExample) |
| MX (1) | MXPA05006120A (enExample) |
| PL (1) | PL375596A1 (enExample) |
| RU (1) | RU2005121568A (enExample) |
| WO (1) | WO2004052821A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004052820A1 (en) * | 2002-12-09 | 2004-06-24 | Eastman Chemical Company | Process for the purification of a crude carboxylic acid slurry |
| US7495125B2 (en) * | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7615663B2 (en) * | 2004-09-02 | 2009-11-10 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| JP2008511665A (ja) * | 2004-09-02 | 2008-04-17 | イーストマン ケミカル カンパニー | 最適化液相酸化 |
| CN101766979B (zh) * | 2004-09-02 | 2012-12-26 | 奇派特石化有限公司 | 优化的液相氧化 |
| BRPI0514769A (pt) * | 2004-09-02 | 2008-06-24 | Eastmann Chemical Company | processo de oxidação em fase lìquida |
| US7504535B2 (en) * | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7683210B2 (en) * | 2004-09-02 | 2010-03-23 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572932B2 (en) * | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7361784B2 (en) * | 2004-09-02 | 2008-04-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| DE102004047076A1 (de) | 2004-09-28 | 2006-04-06 | Zimmer Ag | Verfahren zur Herstellung von Polyestern |
| EP1671938B1 (en) * | 2004-12-15 | 2006-12-13 | Saudi Basic Industries Corporation | Process for preparing purified terephthalic acid |
| CN100447124C (zh) * | 2006-08-31 | 2008-12-31 | 无锡百川化工股份有限公司 | 利用间歇式鼓泡氧化塔多塔串联连续氧化生产偏苯三甲酸的方法 |
| CN102199082B (zh) | 2010-03-26 | 2016-08-17 | 英威达技术有限公司 | 芳香羧酸和氧化催化剂的回收 |
| CN109251139B (zh) * | 2018-11-02 | 2021-06-25 | 中国石油天然气集团有限公司 | 采用深度氧化的pia生产方法和生产系统 |
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| US3064044A (en) | 1957-08-15 | 1962-11-13 | Standard Oil Co | Multistage oxidation system for preparing dicarboxylic acid |
| US3170768A (en) * | 1959-04-22 | 1965-02-23 | Standard Oil Co | System for continuous preparation of terephthalic acid |
| GB983677A (en) | 1962-04-27 | 1965-02-17 | Mitsui Petrochemical Ind | A process for the preparation of terephthalic acid having extremely high purity |
| GB1152577A (en) | 1965-05-17 | 1969-05-21 | Standard Oil Co | Purification of Aromatic Polycarboxylic Acids. |
| US3513193A (en) | 1965-07-28 | 1970-05-19 | Chemische Werke Witten Gmbh | Process for the preparation of terephthalic acid |
| US3584039A (en) | 1967-08-30 | 1971-06-08 | Standard Oil Co | Fiber-grade terephthalic acid by catalytic hydrogen treatment of dissolved impure terephthalic acid |
| DE1909440A1 (de) | 1968-03-18 | 1969-11-13 | Lummos Company | Verfahren zur Herstellung von aromatischen Carbonsaeuren |
| US3839436A (en) | 1969-05-26 | 1974-10-01 | Standard Oil Co | Integration of para-or meta-xylene oxidation to terephthalic acid or isophthalic acid and its purification by hydrogen treatment of aqueous solution |
| US3683018A (en) | 1969-05-26 | 1972-08-08 | Standard Oil Co | Integrated oxidation of isomeric xylene mixture to isomeric phthalic acid mixture and separation of mixture of isomeric phthalic acids into individual isomer products |
| JPS4826740A (enExample) | 1971-08-06 | 1973-04-09 | ||
| GB1358520A (en) | 1972-06-05 | 1974-07-03 | Crampton K J A | Oxidation of aromatic organic compounds |
| GB1388289A (en) | 1972-08-25 | 1975-03-26 | Phillips Petroleum Co | Production and recovery of terephthalic acid |
| JPS5328421B2 (enExample) | 1973-05-15 | 1978-08-15 | ||
| US4158738A (en) * | 1977-05-26 | 1979-06-19 | E. I. Du Pont De Nemours And Company | Process for the production of fiber-grade terephthalic acid |
| US4330676A (en) | 1977-07-04 | 1982-05-18 | Imperial Chemical Industries Limited | Oxidation process |
| US4201871A (en) | 1978-02-23 | 1980-05-06 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for recovering terephthalic acid |
| JPS5517309A (en) | 1978-07-21 | 1980-02-06 | Mitsubishi Gas Chem Co Inc | Preparation of high purity terephthalic acid |
| EP0021747B1 (en) | 1979-07-02 | 1983-05-18 | Imperial Chemical Industries Plc | Process for the preparation of terephthalic acid |
| IT1129759B (it) | 1980-01-23 | 1986-06-11 | Montedison Spa | Metodo per ricuperare in forma attiva i componenti del sistema catalitico della sintesi dell'acido tereftalico |
| GB2072162B (en) * | 1980-03-21 | 1984-03-21 | Labofina Sa | Process for the production and the recovery of terephthalic acid |
| DE3128474A1 (de) | 1980-07-21 | 1982-06-09 | Hercofina, Wilmington, N.C. | Verfahren zur gegenstromwaesche fein verteilter roher terephthalsaeure |
| US4334086A (en) | 1981-03-16 | 1982-06-08 | Labofina S.A. | Production of terephthalic acid |
| US4447646A (en) | 1983-01-28 | 1984-05-08 | Eastman Kodak Company | Process for the purification of terephthalic acid |
| US4605763A (en) | 1984-08-31 | 1986-08-12 | Eastman Kodak Company | Process for the purification of terephthalic acid |
| DE3536622A1 (de) | 1985-10-15 | 1987-04-16 | Krupp Gmbh | Verfahren und vorrichtung zur gewinnung fester stoffe aus fluessigen stoffgemischen |
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| JP2001288139A (ja) | 2000-02-04 | 2001-10-16 | Mitsubishi Chemicals Corp | 高純度テレフタル酸の製造方法 |
| JP2001247511A (ja) | 2000-03-07 | 2001-09-11 | Mitsubishi Chemicals Corp | 芳香族カルボン酸の製造方法 |
| US6517733B1 (en) | 2000-07-11 | 2003-02-11 | Vermeer Manufacturing Company | Continuous flow liquids/solids slurry cleaning, recycling and mixing system |
| JP3895551B2 (ja) | 2001-02-06 | 2007-03-22 | アルプス電気株式会社 | 光学部材の集合体 |
| ATE433472T1 (de) | 2001-12-03 | 2009-06-15 | Kureha Corp | Verfahren zur kontinuierlichen reinigung von polyarylensulfid |
| WO2004052820A1 (en) | 2002-12-09 | 2004-06-24 | Eastman Chemical Company | Process for the purification of a crude carboxylic acid slurry |
| US20040215036A1 (en) | 2003-04-25 | 2004-10-28 | Robert Lin | Method for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam |
| US7282151B2 (en) | 2003-06-05 | 2007-10-16 | Eastman Chemical Company | Process for removal of impurities from mother liquor in the synthesis of carboxylic acid using pressure filtration |
| US7547803B2 (en) | 2003-06-20 | 2009-06-16 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a high purity aromatic polycarboxylic acid |
| US7557243B2 (en) | 2005-05-19 | 2009-07-07 | Eastman Chemical Company | Enriched terephthalic acid composition |
-
2003
- 2003-12-03 KR KR1020057010421A patent/KR101004217B1/ko not_active Expired - Lifetime
- 2003-12-03 RU RU2005121568/04A patent/RU2005121568A/ru not_active Application Discontinuation
- 2003-12-03 EP EP03790246A patent/EP1569888A1/en not_active Withdrawn
- 2003-12-03 BR BR0316462-4A patent/BR0316462A/pt not_active IP Right Cessation
- 2003-12-03 PL PL03375596A patent/PL375596A1/xx unknown
- 2003-12-03 WO PCT/US2003/038306 patent/WO2004052821A1/en not_active Ceased
- 2003-12-03 CA CA002505977A patent/CA2505977C/en not_active Expired - Fee Related
- 2003-12-03 JP JP2005508452A patent/JP2006509045A/ja active Pending
- 2003-12-03 AU AU2003293251A patent/AU2003293251A1/en not_active Abandoned
- 2003-12-03 MX MXPA05006120A patent/MXPA05006120A/es active IP Right Grant
-
2006
- 2006-02-02 US US11/346,393 patent/US7358392B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006509045A (ja) | 2006-03-16 |
| PL375596A1 (en) | 2005-12-12 |
| BR0316462A (pt) | 2005-10-11 |
| US20060128987A1 (en) | 2006-06-15 |
| CA2505977A1 (en) | 2004-06-24 |
| MXPA05006120A (es) | 2005-08-16 |
| AU2003293251A1 (en) | 2004-06-30 |
| KR101004217B1 (ko) | 2010-12-24 |
| WO2004052821A1 (en) | 2004-06-24 |
| EP1569888A1 (en) | 2005-09-07 |
| RU2005121568A (ru) | 2006-01-20 |
| US7358392B2 (en) | 2008-04-15 |
| KR20050085463A (ko) | 2005-08-29 |
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