CA2339956A1 - Process for the production of low color 2,3-epoxypropyl trialkylammonium halide - Google Patents
Process for the production of low color 2,3-epoxypropyl trialkylammonium halide Download PDFInfo
- Publication number
- CA2339956A1 CA2339956A1 CA002339956A CA2339956A CA2339956A1 CA 2339956 A1 CA2339956 A1 CA 2339956A1 CA 002339956 A CA002339956 A CA 002339956A CA 2339956 A CA2339956 A CA 2339956A CA 2339956 A1 CA2339956 A1 CA 2339956A1
- Authority
- CA
- Canada
- Prior art keywords
- aqueous solution
- color
- halide
- hypochlorous acid
- chlorine
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 56
- -1 2,3-epoxypropyl trialkylammonium halide Chemical class 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title abstract description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 48
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 claims abstract description 36
- 125000002091 cationic group Chemical group 0.000 claims abstract description 28
- 229920002472 Starch Polymers 0.000 claims abstract description 27
- 235000019698 starch Nutrition 0.000 claims abstract description 27
- 239000008107 starch Substances 0.000 claims abstract description 26
- 239000005708 Sodium hypochlorite Substances 0.000 claims abstract description 17
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000460 chlorine Substances 0.000 claims description 33
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 150000004820 halides Chemical class 0.000 claims description 25
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 24
- 239000000835 fiber Substances 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- JMMAMAWBEJRFQN-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1CO1 JMMAMAWBEJRFQN-UHFFFAOYSA-M 0.000 claims 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract description 19
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract description 16
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 239000002002 slurry Substances 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000000010 aprotic solvent Substances 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 238000005119 centrifugation Methods 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 21
- 238000010998 test method Methods 0.000 description 21
- 125000005270 trialkylamine group Chemical group 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 101150052147 ALLC gene Proteins 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 210000000085 cashmere Anatomy 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000000665 guar gum Substances 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006297 regenerated protein fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- AGIBHMPYXXPGAX-UHFFFAOYSA-N 2-(iodomethyl)oxirane Chemical compound ICC1CO1 AGIBHMPYXXPGAX-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VFKZECOCJCGZQK-UHFFFAOYSA-M 3-hydroxypropyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCO VFKZECOCJCGZQK-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000005703 Trimethylamine hydrochloride Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920006319 cationized starch Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/08—Ethers
- C08B31/12—Ethers having alkyl or cycloalkyl radicals substituted by heteroatoms, e.g. hydroxyalkyl or carboxyalkyl starch
- C08B31/125—Ethers having alkyl or cycloalkyl radicals substituted by heteroatoms, e.g. hydroxyalkyl or carboxyalkyl starch having a substituent containing at least one nitrogen atom, e.g. cationic starch
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Paper (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Epoxy Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/136,713 US6123738A (en) | 1998-08-19 | 1998-08-19 | Process for the production of low color 2,3-epoxypropyltrialkylammonium halide |
| US09/136,713 | 1998-08-19 | ||
| PCT/US1999/018369 WO2000010987A1 (en) | 1998-08-19 | 1999-08-12 | Process for the production of low color 2,3-epoxypropyl trialkylammonium halide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2339956A1 true CA2339956A1 (en) | 2000-03-02 |
Family
ID=22474040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002339956A Abandoned CA2339956A1 (en) | 1998-08-19 | 1999-08-12 | Process for the production of low color 2,3-epoxypropyl trialkylammonium halide |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6123738A (enExample) |
| EP (1) | EP1112260B1 (enExample) |
| JP (1) | JP2002523406A (enExample) |
| BR (1) | BR9914296A (enExample) |
| CA (1) | CA2339956A1 (enExample) |
| DE (1) | DE69917049T2 (enExample) |
| ES (1) | ES2216563T3 (enExample) |
| ID (1) | ID28825A (enExample) |
| WO (1) | WO2000010987A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8399590B2 (en) * | 2009-10-07 | 2013-03-19 | Akzo Nobel Chemicals International B.V. | Superhydrophilic amphiphilic copolymers and processes for making the same |
| US11173106B2 (en) * | 2009-10-07 | 2021-11-16 | Johnson & Johnson Consumer Inc. | Compositions comprising a superhydrophilic amphiphilic copolymer and a micellar thickener |
| US8258250B2 (en) | 2009-10-07 | 2012-09-04 | Johnson & Johnson Consumer Companies, Inc. | Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof |
| DE102010001350A1 (de) * | 2010-01-29 | 2011-08-04 | Evonik Goldschmidt GmbH, 45127 | Neuartige lineare Polydimethylsiloxan-Polyether-Copolymere mit Amino- und/oder quaternären Ammoniumgruppen und deren Verwendung |
| JP6135275B2 (ja) | 2013-04-22 | 2017-05-31 | 三菱マテリアル株式会社 | 保護膜形成用スパッタリングターゲット |
| FI126960B (en) | 2014-02-06 | 2017-08-31 | Kemira Oyj | Stabilized adhesive formulation |
| CN108951148A (zh) * | 2018-07-28 | 2018-12-07 | 黄勇 | 一种织物硬挺剂的制备方法 |
| CN114921800B (zh) * | 2022-06-16 | 2023-10-31 | 肯特催化材料股份有限公司 | 一种四丙基氢氧化铵的制备方法及其制备的四丙基氢氧化铵水溶液 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2876217A (en) * | 1956-12-31 | 1959-03-03 | Corn Products Co | Starch ethers containing nitrogen and process for making the same |
| US3346563A (en) * | 1964-08-07 | 1967-10-10 | Staley Mfg Co A E | Preparation of quaternary ammonium starch ethers |
| US3532751A (en) * | 1967-01-10 | 1970-10-06 | Dow Chemical Co | Synthesis of 3-chloro-2-hydroxypropyl quaternary ammonium salts |
| US3475458A (en) * | 1967-08-11 | 1969-10-28 | Shell Oil Co | Production of epoxy ammonium salts |
| DE2055046B2 (de) * | 1970-11-09 | 1978-08-03 | Hoffmann's Staerkefabriken Ag, 4902 Bad Salzuflen | Verfahren zur Herstellung von nicht vernetzten kationenaktiven Stärkederivaten |
| US4066673A (en) * | 1974-02-25 | 1978-01-03 | Westvaco Corporation | Process for making quaternary amines of epichlorohydrin |
| NL8007126A (nl) * | 1980-12-31 | 1982-07-16 | Zaltbommel Chem Fab | Werkwijze ter bereiding van watervrij 2-hydroxy-3-chloorpropyltrimethylammoniumchloride. |
| DE3103713C2 (de) * | 1981-02-04 | 1983-03-03 | Degussa Ag, 6000 Frankfurt | Verfahren zur Reinigung der bei der Herstellung von 2,3-Epoxypropyltrialkylammoniumchloriden entstehenden Umsetzungsgemische |
| US4594452A (en) * | 1985-06-24 | 1986-06-10 | Allied Corporation | Process for the preparation of anhydrous N-(3-chloro-2-hydroxypropyl) trialkylammonium salts |
| US5006125A (en) * | 1988-09-13 | 1991-04-09 | The Dow Chemical Company | Process for improving the dyeability and whiteness of cellulosic fabrics |
-
1998
- 1998-08-19 US US09/136,713 patent/US6123738A/en not_active Expired - Lifetime
-
1999
- 1999-08-12 DE DE69917049T patent/DE69917049T2/de not_active Expired - Fee Related
- 1999-08-12 CA CA002339956A patent/CA2339956A1/en not_active Abandoned
- 1999-08-12 ES ES99945046T patent/ES2216563T3/es not_active Expired - Lifetime
- 1999-08-12 JP JP2000566260A patent/JP2002523406A/ja active Pending
- 1999-08-12 BR BR9914296-1A patent/BR9914296A/pt not_active Application Discontinuation
- 1999-08-12 EP EP99945046A patent/EP1112260B1/en not_active Expired - Lifetime
- 1999-08-12 ID IDW20010367A patent/ID28825A/id unknown
- 1999-08-12 WO PCT/US1999/018369 patent/WO2000010987A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1112260B1 (en) | 2004-05-06 |
| US6123738A (en) | 2000-09-26 |
| BR9914296A (pt) | 2001-06-19 |
| DE69917049T2 (de) | 2004-09-02 |
| ID28825A (id) | 2001-07-05 |
| JP2002523406A (ja) | 2002-07-30 |
| DE69917049D1 (de) | 2004-06-09 |
| WO2000010987A1 (en) | 2000-03-02 |
| ES2216563T3 (es) | 2004-10-16 |
| EP1112260A1 (en) | 2001-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |