CN1232499C - 生产低色值二苯基甲烷多异氰酸酯的方法 - Google Patents
生产低色值二苯基甲烷多异氰酸酯的方法 Download PDFInfo
- Publication number
- CN1232499C CN1232499C CNB021420475A CN02142047A CN1232499C CN 1232499 C CN1232499 C CN 1232499C CN B021420475 A CNB021420475 A CN B021420475A CN 02142047 A CN02142047 A CN 02142047A CN 1232499 C CN1232499 C CN 1232499C
- Authority
- CN
- China
- Prior art keywords
- temperature
- polyisocyanates
- reaction mixture
- aniline
- reaction
- 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
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 22
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 50
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229920000768 polyamine Polymers 0.000 claims abstract description 21
- 239000011541 reaction mixture Substances 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000006386 neutralization reaction Methods 0.000 claims description 14
- 239000003377 acid catalyst Substances 0.000 claims description 12
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 235000019256 formaldehyde Nutrition 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- -1 amine acetal Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 230000011218 segmentation Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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
- C08G73/02—Polyamines
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10141620.2 | 2001-08-24 | ||
| DE10141620A DE10141620A1 (de) | 2001-08-24 | 2001-08-24 | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1406925A CN1406925A (zh) | 2003-04-02 |
| CN1232499C true CN1232499C (zh) | 2005-12-21 |
Family
ID=7696548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB021420475A Expired - Fee Related CN1232499C (zh) | 2001-08-24 | 2002-08-23 | 生产低色值二苯基甲烷多异氰酸酯的方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6720455B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1288190B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2003119235A (cg-RX-API-DMAC7.html) |
| KR (1) | KR100860910B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1232499C (cg-RX-API-DMAC7.html) |
| BR (1) | BR0203370A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2399483A1 (cg-RX-API-DMAC7.html) |
| DE (2) | DE10141620A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2280459T3 (cg-RX-API-DMAC7.html) |
| HK (1) | HK1053105A1 (cg-RX-API-DMAC7.html) |
| HU (1) | HUP0202841A3 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA02008245A (cg-RX-API-DMAC7.html) |
| PL (1) | PL355618A1 (cg-RX-API-DMAC7.html) |
| PT (1) | PT1288190E (cg-RX-API-DMAC7.html) |
| SG (1) | SG99409A1 (cg-RX-API-DMAC7.html) |
| TW (1) | TW575594B (cg-RX-API-DMAC7.html) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10211021A1 (de) * | 2002-03-13 | 2003-09-25 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
| DE10228734A1 (de) * | 2002-06-27 | 2004-01-22 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
| DE102004032416A1 (de) * | 2004-07-05 | 2006-02-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyaminen der Diphenylmethanreihe bei niedriger Protonierung |
| DE102004052370A1 (de) * | 2004-10-28 | 2006-05-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| CN101326153B (zh) * | 2005-12-08 | 2012-06-13 | 亨茨曼国际有限公司 | 制备二氨基二苯基甲烷的方法 |
| DE102006004047A1 (de) * | 2006-01-28 | 2007-08-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| CN101279923B (zh) * | 2007-04-06 | 2010-08-25 | 宁波万华聚氨酯有限公司 | 一种制备多亚甲基多苯基多胺的方法 |
| EP2145874B1 (en) * | 2007-04-06 | 2011-07-27 | Ningbo Wanhua Polyurethanes Co., Ltd. | Process for the preparation of polymethylene polyphenyl polyamine |
| EP2000459A1 (en) * | 2007-06-04 | 2008-12-10 | Huntsman International Llc | Process for the preparation of di-and polyamines of the diphenylmethane series |
| EP2039676A1 (en) | 2007-09-19 | 2009-03-25 | Huntsman International Llc | Process for the production of di-and polyamines of the diphenylmethane series |
| EP2062869A1 (en) * | 2007-09-19 | 2009-05-27 | Huntsman International Llc | Process for the production of di-and polyamines of the diphenylmethane series |
| EP2421818B1 (de) | 2009-04-24 | 2014-08-27 | Basf Se | Verfahren zur herstellung von farbstabilem mda und mdi |
| KR101785129B1 (ko) | 2009-12-18 | 2017-10-12 | 바스프 에스이 | Ｍｄａ 합성에서 균일 촉매의 비용 효과적인 침착을 위한 2 단 공정 |
| CN107827756B (zh) * | 2017-11-17 | 2020-09-08 | 万华化学集团股份有限公司 | 一种低n-甲基杂质含量的二苯基甲烷系列二胺和多胺的制备方法及装置和催化剂 |
| CN111646927A (zh) * | 2020-06-12 | 2020-09-11 | 万华节能科技集团股份有限公司 | 阻燃二苯基甲烷二异氰酸酯的衍生物及其合成方法 |
| WO2025073928A1 (en) | 2023-10-06 | 2025-04-10 | Basf Se | Process for preparing mda |
| CN119100935A (zh) * | 2024-09-04 | 2024-12-10 | 万华化学集团股份有限公司 | 一种二苯基甲烷系列的二胺和多胺的制备方法及应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60199861A (ja) * | 1984-03-23 | 1985-10-09 | Mitsui Toatsu Chem Inc | 芳香族ジアミン類の精製方法 |
| DE4208359A1 (de) | 1992-03-16 | 1993-09-23 | Bayer Ag | Verfahren zur herstellung von isocyanaten oder isocyanatgemischen und deren verwendung zur herstellung von polyurethanschaumstoffen |
| US5310769A (en) | 1992-05-01 | 1994-05-10 | Bayer Aktiengesellschaft | Process for the production of polyamine mixtures of the polyamino-polyaryl-polymethylene series |
| DE4232769A1 (de) | 1992-09-30 | 1994-03-31 | Basf Ag | Verfahren zur Herstellung von Mischungen aus Diphenylmethandiisocyanaten und Polyphenyl-polymethylen-polyisocyanaten mit einer verminderten Iodfarbzahl |
| US6031136A (en) * | 1993-07-21 | 2000-02-29 | Bayer Corporation | Process for preparing methylene diphenylamines by partial neutralization of acidic methylene diphenylamines |
| DE19804915A1 (de) * | 1998-02-07 | 1999-08-12 | Basf Ag | Verfahren zur Herstellung von Methylendi(phenylamin) und Methylendi(phenylisocyanat) |
| DE19815055A1 (de) | 1998-04-03 | 1999-10-07 | Bayer Ag | Verfahren zur Farbaufhellung von polymeren Diphenylmethandiisocyanat sowie die Verwendung von aufgehellten Diphenylmethandiisocyanat bei der Herstellung von Polyurethankunststoffen |
-
2001
- 2001-08-24 DE DE10141620A patent/DE10141620A1/de not_active Withdrawn
-
2002
- 2002-08-08 SG SG200204842A patent/SG99409A1/en unknown
- 2002-08-12 PT PT02017778T patent/PT1288190E/pt unknown
- 2002-08-12 DE DE50209217T patent/DE50209217D1/de not_active Expired - Lifetime
- 2002-08-12 ES ES02017778T patent/ES2280459T3/es not_active Expired - Lifetime
- 2002-08-12 EP EP02017778A patent/EP1288190B1/de not_active Expired - Lifetime
- 2002-08-20 US US10/224,003 patent/US6720455B2/en not_active Expired - Fee Related
- 2002-08-22 JP JP2002241861A patent/JP2003119235A/ja active Pending
- 2002-08-22 CA CA002399483A patent/CA2399483A1/en not_active Abandoned
- 2002-08-22 TW TW91118950A patent/TW575594B/zh not_active IP Right Cessation
- 2002-08-22 PL PL02355618A patent/PL355618A1/xx not_active Application Discontinuation
- 2002-08-23 KR KR1020020049991A patent/KR100860910B1/ko not_active Expired - Fee Related
- 2002-08-23 MX MXPA02008245A patent/MXPA02008245A/es unknown
- 2002-08-23 CN CNB021420475A patent/CN1232499C/zh not_active Expired - Fee Related
- 2002-08-23 HU HU0202841A patent/HUP0202841A3/hu unknown
- 2002-08-23 BR BR0203370-4A patent/BR0203370A/pt not_active IP Right Cessation
-
2003
- 2003-07-24 HK HK03105349.4A patent/HK1053105A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0202841A2 (hu) | 2003-03-28 |
| EP1288190A2 (de) | 2003-03-05 |
| TW575594B (en) | 2004-02-11 |
| SG99409A1 (en) | 2003-10-27 |
| EP1288190A3 (de) | 2003-06-04 |
| HUP0202841A3 (en) | 2004-03-01 |
| US6720455B2 (en) | 2004-04-13 |
| HU0202841D0 (cg-RX-API-DMAC7.html) | 2002-11-28 |
| CA2399483A1 (en) | 2003-02-24 |
| MXPA02008245A (es) | 2005-09-08 |
| HK1053105A1 (zh) | 2003-10-10 |
| PT1288190E (pt) | 2007-04-30 |
| KR20030017415A (ko) | 2003-03-03 |
| KR100860910B1 (ko) | 2008-09-29 |
| ES2280459T3 (es) | 2007-09-16 |
| EP1288190B1 (de) | 2007-01-10 |
| DE10141620A1 (de) | 2003-03-06 |
| CN1406925A (zh) | 2003-04-02 |
| JP2003119235A (ja) | 2003-04-23 |
| BR0203370A (pt) | 2003-05-27 |
| DE50209217D1 (de) | 2007-02-22 |
| PL355618A1 (en) | 2003-03-10 |
| US20030045745A1 (en) | 2003-03-06 |
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