JP2002534495A - アゾイミノエーテル及びアゾカルボン酸エステルの製造方法並びに新規のアゾカルボン酸混合エステル - Google Patents
アゾイミノエーテル及びアゾカルボン酸エステルの製造方法並びに新規のアゾカルボン酸混合エステルInfo
- Publication number
- JP2002534495A JP2002534495A JP2000593568A JP2000593568A JP2002534495A JP 2002534495 A JP2002534495 A JP 2002534495A JP 2000593568 A JP2000593568 A JP 2000593568A JP 2000593568 A JP2000593568 A JP 2000593568A JP 2002534495 A JP2002534495 A JP 2002534495A
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- ester
- alkyl
- unsubstituted
- alkoxy
- 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.)
- Pending
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 56
- 239000002253 acid Substances 0.000 title claims abstract description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 102
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 87
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 61
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 238000004519 manufacturing process Methods 0.000 claims abstract description 24
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 19
- 150000002170 ethers Chemical class 0.000 claims abstract description 18
- 239000003849 aromatic solvent Substances 0.000 claims abstract description 6
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 150000002367 halogens Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 19
- 150000001298 alcohols Chemical class 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 239000012074 organic phase Substances 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 238000003786 synthesis reaction Methods 0.000 claims description 11
- -1 azo imino ether salt Chemical class 0.000 claims description 10
- 238000011065 in-situ storage Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000003505 polymerization initiator Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- LYIMSMCQBKXQDK-UHFFFAOYSA-N 2-ethyl-2-methylhexanoic acid Chemical compound CCCCC(C)(CC)C(O)=O LYIMSMCQBKXQDK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000012467 final product Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- SYWIXHZXHQDFOO-UHFFFAOYSA-N methyl n-phenyliminocarbamate Chemical compound COC(=O)N=NC1=CC=CC=C1 SYWIXHZXHQDFOO-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HOSVESHQDSFAST-UHFFFAOYSA-N 2-[2-(2-cyanopropan-2-yl)hydrazinyl]-2-methylpropanenitrile Chemical compound N#CC(C)(C)NNC(C)(C)C#N HOSVESHQDSFAST-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VBZBISQOWJYWCC-UHFFFAOYSA-N 2-(2-carboxypropan-2-yldiazenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)N=NC(C)(C)C(O)=O VBZBISQOWJYWCC-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 238000003482 Pinner synthesis reaction Methods 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- WLSFTWSDLDZJJX-UHFFFAOYSA-N Cl.NON Chemical compound Cl.NON WLSFTWSDLDZJJX-UHFFFAOYSA-N 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OSDZHDOKXGSWOD-UHFFFAOYSA-N nitroxyl;hydrochloride Chemical compound Cl.O=N OSDZHDOKXGSWOD-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- ZVQXQPNJHRNGID-UHFFFAOYSA-N tetramethylsuccinonitrile Chemical compound N#CC(C)(C)C(C)(C)C#N ZVQXQPNJHRNGID-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/04—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
- C07C257/06—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR99/00391 | 1999-01-15 | ||
| FR9900391A FR2788517B1 (fr) | 1999-01-15 | 1999-01-15 | Procede de preparation d'azoiminoethers et d'esters d'acides azocarboxyliques, et nouveaux esters mixtes d'acides azocarboxyliques |
| PCT/FR2000/000022 WO2000042000A1 (fr) | 1999-01-15 | 2000-01-07 | Procede de preparation d'azoiminoethers et d'esters d'acides azocarboxyliques, et nouveaux esters mixtes d'acides azocarboxyliques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002534495A true JP2002534495A (ja) | 2002-10-15 |
| JP2002534495A5 JP2002534495A5 (enExample) | 2008-05-29 |
Family
ID=9540891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000593568A Pending JP2002534495A (ja) | 1999-01-15 | 2000-01-07 | アゾイミノエーテル及びアゾカルボン酸エステルの製造方法並びに新規のアゾカルボン酸混合エステル |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6407219B1 (enExample) |
| EP (1) | EP1147077B1 (enExample) |
| JP (1) | JP2002534495A (enExample) |
| KR (1) | KR100776703B1 (enExample) |
| CN (1) | CN1211356C (enExample) |
| AT (1) | ATE402139T1 (enExample) |
| AU (1) | AU3051200A (enExample) |
| CA (1) | CA2359459A1 (enExample) |
| DE (1) | DE60039582D1 (enExample) |
| FR (1) | FR2788517B1 (enExample) |
| IL (1) | IL144099A0 (enExample) |
| PL (1) | PL348863A1 (enExample) |
| RU (1) | RU2245872C2 (enExample) |
| WO (1) | WO2000042000A1 (enExample) |
| ZA (1) | ZA200105221B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2813319A1 (fr) * | 2000-08-29 | 2002-03-01 | Atofina | Procede de fabrication de fibres a base d'acrylonitrile |
| FR2870240B1 (fr) * | 2004-05-13 | 2006-07-07 | Arkema Sa | Procede de preparation d'une alcoxyamine ou de ses sels comprenant une etape de photolyse |
| CN103193686B (zh) * | 2013-04-26 | 2014-10-29 | 山东师范大学 | 酯化法制备偶氮二甲酸二烷基酯 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS582230B2 (ja) | 1974-01-29 | 1983-01-14 | 和光純薬工業 （株） | アゾグアニル化合物の製法 |
| GB2111979A (en) * | 1981-11-19 | 1983-07-13 | Ici Plc | Azoimindether hydrochloride production |
| DE3471664D1 (en) * | 1983-11-10 | 1988-07-07 | Nitto Boseki Co Ltd | Process for producing polymers of monoallylamine |
| JPH0625100B2 (ja) * | 1986-01-14 | 1994-04-06 | 和光純薬工業株式会社 | アゾイミノエ−テルの製造法 |
| JP4092739B2 (ja) * | 1996-09-27 | 2008-05-28 | 和光純薬工業株式会社 | アゾエステル化合物の新規な製造方法 |
-
1999
- 1999-01-15 FR FR9900391A patent/FR2788517B1/fr not_active Expired - Lifetime
-
2000
- 2000-01-07 JP JP2000593568A patent/JP2002534495A/ja active Pending
- 2000-01-07 AU AU30512/00A patent/AU3051200A/en not_active Abandoned
- 2000-01-07 CN CNB008027595A patent/CN1211356C/zh not_active Expired - Lifetime
- 2000-01-07 CA CA002359459A patent/CA2359459A1/en not_active Abandoned
- 2000-01-07 WO PCT/FR2000/000022 patent/WO2000042000A1/fr not_active Ceased
- 2000-01-07 US US09/889,147 patent/US6407219B1/en not_active Expired - Lifetime
- 2000-01-07 PL PL00348863A patent/PL348863A1/xx not_active Application Discontinuation
- 2000-01-07 KR KR1020017008907A patent/KR100776703B1/ko not_active Expired - Fee Related
- 2000-01-07 RU RU2001122813/04A patent/RU2245872C2/ru not_active IP Right Cessation
- 2000-01-07 AT AT00900534T patent/ATE402139T1/de not_active IP Right Cessation
- 2000-01-07 IL IL14409900A patent/IL144099A0/xx unknown
- 2000-01-07 DE DE60039582T patent/DE60039582D1/de not_active Expired - Fee Related
- 2000-01-07 EP EP00900534A patent/EP1147077B1/fr not_active Expired - Lifetime
-
2001
- 2001-06-25 ZA ZA200105221A patent/ZA200105221B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL348863A1 (en) | 2002-06-17 |
| RU2245872C2 (ru) | 2005-02-10 |
| KR100776703B1 (ko) | 2007-11-16 |
| DE60039582D1 (de) | 2008-09-04 |
| ATE402139T1 (de) | 2008-08-15 |
| CN1336913A (zh) | 2002-02-20 |
| FR2788517A1 (fr) | 2000-07-21 |
| WO2000042000A1 (fr) | 2000-07-20 |
| EP1147077A1 (fr) | 2001-10-24 |
| EP1147077B1 (fr) | 2008-07-23 |
| ZA200105221B (en) | 2002-10-10 |
| US6407219B1 (en) | 2002-06-18 |
| CN1211356C (zh) | 2005-07-20 |
| IL144099A0 (en) | 2002-05-23 |
| FR2788517B1 (fr) | 2001-03-16 |
| KR20010101530A (ko) | 2001-11-14 |
| AU3051200A (en) | 2000-08-01 |
| CA2359459A1 (en) | 2000-07-20 |
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