WO2001005870A1 - Polycarbonate mit asparaginsäureesterfunktionellen silikonen - Google Patents

Polycarbonate mit asparaginsäureesterfunktionellen silikonen Download PDF

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Publication number
WO2001005870A1
WO2001005870A1 PCT/EP2000/006381 EP0006381W WO0105870A1 WO 2001005870 A1 WO2001005870 A1 WO 2001005870A1 EP 0006381 W EP0006381 W EP 0006381W WO 0105870 A1 WO0105870 A1 WO 0105870A1
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WO
WIPO (PCT)
Prior art keywords
functional silicones
aspartic acid
silicones
acid ester
functional
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.)
Ceased
Application number
PCT/EP2000/006381
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German (de)
English (en)
French (fr)
Inventor
Burkhard KÖHLER
Klaus Horn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE1999133129 external-priority patent/DE19933129C2/de
Application filed by Bayer AG filed Critical Bayer AG
Priority to JP2001511521A priority Critical patent/JP2003505549A/ja
Priority to EP00949269A priority patent/EP1203044B1/de
Priority to US10/031,912 priority patent/US6664342B1/en
Priority to DE50003926T priority patent/DE50003926D1/de
Priority to AU62690/00A priority patent/AU6269000A/en
Publication of WO2001005870A1 publication Critical patent/WO2001005870A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
    • C08G64/085—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing silicon
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/18—Block or graft polymers
    • C08G64/186—Block or graft polymers containing polysiloxane sequences
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
    • C08G77/448—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences containing polycarbonate sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent

Definitions

  • the invention relates to aromatic polycarbonates containing aspartic acid-functional silicones which are distinguished by very good low-temperature toughness and very good ESC behavior.
  • Aromatic polycarbonates are highly impact-resistant plastics that are characterized by very good room temperature impact strength. Disadvantages are the susceptibility to solvents (stress crack, ESC behavior) and the declining
  • aromatic polycarbonates containing aspartic ester-functional silicones which can be prepared by incorporating the aspartic ester-functional silicones during the polycarbonate synthesis from bisphenols and carbonic acid derivatives or by reaction of unmodified aromatic polycarbonate with aspartic ester-functional silicones, can be produced by a very good low temperature and have very good ESC behavior.
  • the invention therefore relates to aromatic polycarbonates with 1 to
  • aspartic ester-functional silicones obtainable by reaction of bisphenols and aspartic acid ester-functional silicones with carbonic acid derivatives or by reaction of polycarbonates with aspartic acid ester-functional silicones.
  • Aspartic acid ester-functional silicones are preferably used, which can be obtained by adding fumaric acid esters and / or maleic acid esters of the formula (I)
  • ROOC-CH CH-COOR (I), where R is a CC ⁇ alkyl or alkenyl radical,
  • Preferred compounds of the formula (I) are methyl maleic or fumaric acid, methyl maleic or fumaric acid, maleic or fumaric acid n-propyl, maleic or fumaric acid isopropyl, maleic or fumaric acid n-butyl, maleic or fumaric acid i-butyl ester, maleic acid or
  • Fumaric acid sec-butyl ester maleic acid or fumaric acid tert-butyl ester, maleic acid or fumaric acid allyl ester.
  • the amine-functional silicones are obtainable by reacting open-chain siloxanes and / or cyclic oligosiloxanes, in which 45 to 100% of the substituents on the siloxane groups are methyl groups and the rest are preferably phenyl groups, with aminosilanes, preferably with aminosilanes of the formula (II)
  • X is a divalent organic radical with 2 to 22 carbon atoms, preferably -CH 2 -CH 2 -CH 2 - and
  • n is 1 or 2 or 3, preferably 2 or 3, very particularly preferably 2.
  • the reaction is preferably carried out at temperatures from 120 to 250 ° C. in the presence of acidic catalysts, such as, for example, p-toluenesulfonic acid, basic catalysts, such as, for example, alkali metal alcoholates or metal catalysts, such as, for example, dibutyltin oxide, SnCl2, Sn (II) carboxylates, or transition metal salts.
  • acidic catalysts such as, for example, p-toluenesulfonic acid
  • basic catalysts such as, for example, alkali metal alcoholates or metal catalysts, such as, for example, dibutyltin oxide, SnCl2, Sn (II) carboxylates, or transition metal salts.
  • the amino-functional silicones used according to the invention can also be produced by polymer-analogous hydrosilylation of SiH-functional silicones with unsaturated amines, preferably allylamine.
  • the amine equivalent weight of the aspartic ester-functional silicones according to the invention and the amino-functional silicones used as starting materials is 1000 to 50,000 g / val, preferably 4000 to 20,000 g / val.
  • the molecular weight of the aspartic ester-functional silicones is 2,000 to 5,000,000 g / mol, preferably 20,000 to 2,000,000 g / mol.
  • the aspartic acid ester-functional silicones are prepared by reacting amino-functional silicones with compounds of the formula (I).
  • the molar ratio of amino groups to compounds of formula (I) is 1: 1 to 1:20, preferably 1: 2 to 1:10, the reaction is 1 to 10 hours at 80 to
  • the excess of compounds of formula (I) is then distilled off at a pressure of 1 to 100 mbar and temperatures of 150 to 250 ° C.
  • the amino functionalization of the open-chain siloxanes and / or cyclic oligosiloxanes with aminosilanes and the subsequent reaction with compounds of the formula (I) is carried out in a preferred embodiment in a one-pot reaction in succession.
  • an aspartic ester-functional silicone which contains the following structural unit:
  • the aspartic acid ester-functional silicones according to the invention can be used as soft blocks or impact modifiers for plastics.
  • Aromatic polycarbonates suitable according to the invention as reactants for the aspartic ester-functional silicones are those based on the diphenols of the
  • A is a single bond, -CC 5 alkylene, C 2 -Cs alkylidene, C 5 -C 6 cycloalkylidene, -S- or -SO 2 -,
  • R 1 and R 2 independently of one another are hydrogen, halogen, preferably chlorine or bromine, -CC 8 -alkyl, C 5 -C 6 -cycloalkyl, C 6 -C -o-aryl, preferably phenyl, and C -C 2 -aryalkyl, preferably Phenyl-C 1 -C 6 -alkyl, in particular benzyl,
  • n is an integer from 4 to 7, preferably 4 or 5
  • R 3 and R 4 can be selected individually for each Z, independently of one another hydrogen or
  • Z mean carbon, with the proviso that ZR and R 4 mean alkyl on at least one atom.
  • Examples include hydroquinone, resorcinol, dihydroxydiphenyl, bis (hydroxyphenyl) alkanes, bis (hydroxyphenyl) cycloalkanes, bis (hydroxyphenyl) sulfides, ethers, ketones, sulfoxides, sulfones and ⁇ , ⁇ - Bis- (hydroxyphenyl) -diisopropylbenzenes and their nuclear alkylated and nuclear halogenated compounds.
  • Suitable diphenols are described, for example, in US Pat. Nos. 3,028,365, 2,999,835, 3,062,781, 3,148,172 and 4,982,014, in German Offenlegungsschriften 1,570,703 and 2,063,050 and in the monograph "H. Schnell, Chemistry and Physics of Polycarbonates, Interscience Publishers, New York, 1964 ".
  • Preferred diphenols are 4,4'-dihydroxydiphenyl, 2,2-bis (4-hydroxyphenyl) propane, 2,4-bis (4-hydroxyphenyl) -2-methylbutane, 1,1-bis (4-hydroxyphenyl ) -cyclohexane, ⁇ , ⁇ -bis- (4-hydroxyphenyl) -p-diisopropylbenzene, 2,2-bis- (3-methyl-4-hydroxyphenyl) -propane, 2,2-bis- (3-chloro-4 -hydroxyphenyl) propane, bis (3,5-dimethyl-4-hydroxyphenyl) methane, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propane,
  • diphenols are, for example: 2,2-bis (4-hydroxyphenyl) propane, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propane, 2,2-bis (3,5 dichloro-4-hydroxyphenyl) -propane,
  • 1,1-bis (3,5-dimethyl-4-hydroxyphenyl) -4-methylcyclohexane 1,1-bis (3,5-dimethyl-4-hydroxyphenyl) -4-methylcyclohexane.
  • 2,2-bis (4-hydroxyphenyl) propane and 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane are preferred.
  • phenolic hydroxyl groups can be used in a known manner.
  • Some of the compounds which can be used with three or more than three phenolic hydroxyl groups are, for example, 1,3,5-tri- (4-hydroxyphenyl) benzene, 1,1,1-tri- (4-hydroxyphenyl) ethane, 2, 6-bis (2-hydroxy-5'-methyl-benzyl) -4-methylphenol, 2- (4-hydroxyphenyl) -2- (2,4-dihydroxyphenyl) propane, hexa- (4- (4th -hydroxyphenylisopropyl) phenyl) ortho-terephthalic acid ester, tetra- (4-hydroxyphenyl) methane and 1,4-bis- (4 ', 4 "-dihydroxytriphenyl) methyl) benzene.
  • Some of the other three-functional compounds are 2,4-dihydroxybenzoic acid, trimesic acid, cyano chloride and 3,3-bis- (4-hydroxy-3-methylphenyl) -2-oxo-2,3-dihydroindole.
  • the block polycarbonates according to the invention can essentially be prepared by the known dispersed phase solution process (so-called two-phase interface process) (cf. H. Schnell, "Chemistry and Physics of Polycarbonates", Polymer Review, Vol. IX, page 27 ff, Interscience Publ. 1964) respectively:
  • the diphenols to be used are dissolved in an aqueous alkaline phase.
  • the chain terminators required for the production of the polycarbonates according to the invention are added in amounts of 1 to 20 mol%, based on moles of diphenol, in an organic solvent or in bulk.
  • the reaction is then carried out with phosgene in the presence of an inert, preferably polycarbonate-dissolving, organic phase.
  • the reaction temperature is between 0 ° C and 40 ° C.
  • the polyiso Butylene- ⁇ -halogeno-ketocarboxylic acids are added in the desired amount to the reaction as pure substance or dissolved in the solvent forming the organic phase.
  • Another object of the invention is a process for the production of aromatic polycarbonates containing aspartic ester functional silicones, characterized in that aromatic polycarbonates are reacted with silicones functional aspartic ester in solution or in the melt.
  • Solutions of the reactants can be mixed in solvents with a boiling point greater than 100 ° C., the mixture heated to reflux and the reaction mixture worked up by precipitation or spray evaporation.
  • the reactants can be dissolved, mixed and evaporated in evaporation extruders. This procedure is the preferred embodiment of the invention.
  • the reactants can also be mixed in the melt in kneaders or extruders at temperatures of 170 to 330 ° C.
  • Another object of the invention is a process for the preparation of aromatic polycarbonates containing aspartic ester-functional silicones, characterized in that bisphenols and aspartic ester-functional silicones are reacted with carbonic acid derivatives, if appropriate in the presence of chain terminators and / or branching agents.
  • aromatic polycarbonates When carrying out this process according to the invention, methods are used which have been described above for the production of the aromatic polycarbonates, with an amount of silicones functional with aspartic acid ester being present such that the content is 1 to 30% by weight, preferably 5 to 15% by weight ,
  • the aromatic polycarbonates according to the invention can, before or after their processing, be admixed with the usual amounts of additives, such as stabilizers, mold release agents, pigments, flame retardants, antistatic agents, fillers and reinforcing materials, for thermoplastic polycarbonates.
  • the aromatic polycarbonates according to the invention can be processed into moldings by, for example, extruding the aromatic polycarbonates isolated in a known manner into granules and, if appropriate after injection of the additives mentioned above, processing these granules into various articles in a known manner.
  • aromatic polycarbonates according to the invention can be used as moldings wherever the polycarbonates known hitherto have been used, that is to say, for example, in the electrical sector and in the construction sector, specifically when increased resistance to chemicals is required.
  • Examples of uses are films, composite films, extrusion and injection molded parts with and without fillers or glass fiber reinforcement such as Safety helmets, foams, sheet goods and blown bodies, as well as medical articles such as tubes and short-term implants.
  • aromatic polycarbonates according to the invention also serve as blend partners for thermoplastic molding compositions.
  • Polycarbonate with a relative solution viscosity of 1.28 shows an MVI of 6, a tough / brittle transition of + 10 ° C and the following ESC behavior:

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Silicon Polymers (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
PCT/EP2000/006381 1999-07-19 2000-07-06 Polycarbonate mit asparaginsäureesterfunktionellen silikonen Ceased WO2001005870A1 (de)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2001511521A JP2003505549A (ja) 1999-07-19 2000-07-06 アスパラギン酸エステル官能基を有するシリコーンを含有する芳香族ポリカーボネート
EP00949269A EP1203044B1 (de) 1999-07-19 2000-07-06 Polycarbonate mit asparaginsäureesterfunktionellen silikonen
US10/031,912 US6664342B1 (en) 1999-07-19 2000-07-06 Polycarbonates containing aspartic acid-ester functional silicones
DE50003926T DE50003926D1 (de) 1999-07-19 2000-07-06 Polycarbonate mit asparaginsäureesterfunktionellen silikonen
AU62690/00A AU6269000A (en) 1999-07-19 2000-07-06 Polycarbonates containing aspartic acid ester-functional silicones

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19933077.8 1999-07-19
DE1999133129 DE19933129C2 (de) 1999-07-19 1999-07-19 Aromatische Polycarbonate mit asparaginsäureesterfunktionellen Silikonen als Modifikator
DE19933077 1999-07-19
DE19933129.4 1999-07-19

Publications (1)

Publication Number Publication Date
WO2001005870A1 true WO2001005870A1 (de) 2001-01-25

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PCT/EP2000/006381 Ceased WO2001005870A1 (de) 1999-07-19 2000-07-06 Polycarbonate mit asparaginsäureesterfunktionellen silikonen

Country Status (7)

Country Link
US (1) US6664342B1 (https=)
EP (1) EP1203044B1 (https=)
JP (1) JP2003505549A (https=)
AU (1) AU6269000A (https=)
DE (1) DE50003926D1 (https=)
ES (1) ES2208375T3 (https=)
WO (1) WO2001005870A1 (https=)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2108025A4 (en) * 2006-12-29 2012-01-25 Cheil Ind Inc POLYCARBONATE POLYSILOXAN COPOLYMER RESIN COMPOSITION HAVING HIGH RESISTANCE TO CHIP AND MECHANICAL STRENGTH
CN115975205A (zh) * 2023-01-29 2023-04-18 厦门弘嘉顺逸科技有限公司 一种自乳化氨基硅油的制备方法和氨基硅油乳液
WO2024036052A1 (en) 2022-08-09 2024-02-15 Exxonmobil Chemical Patents Inc. Methods for preparing diphenylsilane bridged c1 symmetric catalysts and polymers made therefrom

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KR100791902B1 (ko) * 2002-03-14 2008-01-07 에스케이케미칼주식회사 폴리아스파르트산 제조방법
DE102010063737A1 (de) 2010-12-21 2012-06-21 Wacker Chemie Ag Siliconasparaginat-Copolymere
WO2012158767A1 (en) * 2011-05-17 2012-11-22 Momentive Performance Materials Gmbh Polysiloxane-polyorgano block copolymers
US11179312B2 (en) 2017-06-05 2021-11-23 Momentive Performance Materials Inc. Aqueous compositions for the treatment of hair
ES2972689T3 (es) * 2018-10-19 2024-06-14 Momentive Performance Mat Gmbh Polisiloxanos con funcionalidad éster de ácido aspártico, su preparación y uso de los mismos
US11090255B2 (en) 2018-12-04 2021-08-17 Momentive Performance Materials Inc. Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
US10617617B1 (en) 2018-12-04 2020-04-14 Momentive Performance Materials Inc. Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
US12577353B2 (en) 2022-02-14 2026-03-17 Momentive Performance Materials Gmbh Aspartic acid ester-functional polysiloxanes, their preparation and use thereof

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US5194524A (en) * 1990-10-05 1993-03-16 General Electric Company Process for making poly(carbonate-siloxanes) via alkyl amino terminated silicones
DE4421556A1 (de) * 1994-06-20 1995-12-21 Bayer Ag Polyisobutylene mit Asparaginsäureesterendgruppen
EP0764676A2 (en) * 1995-09-20 1997-03-26 General Electric Company Method of preparing polycarbonate-polysiloxane block copolymers
EP0924231A1 (en) * 1997-12-17 1999-06-23 Bayer Corporation Aqueous polyurethane/urea dispersions containing alkoxysilane groups

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US3743588A (en) * 1971-10-18 1973-07-03 Gen Electric Ion-specific membrane
US5194524A (en) * 1990-10-05 1993-03-16 General Electric Company Process for making poly(carbonate-siloxanes) via alkyl amino terminated silicones
DE4421556A1 (de) * 1994-06-20 1995-12-21 Bayer Ag Polyisobutylene mit Asparaginsäureesterendgruppen
EP0764676A2 (en) * 1995-09-20 1997-03-26 General Electric Company Method of preparing polycarbonate-polysiloxane block copolymers
EP0924231A1 (en) * 1997-12-17 1999-06-23 Bayer Corporation Aqueous polyurethane/urea dispersions containing alkoxysilane groups

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2108025A4 (en) * 2006-12-29 2012-01-25 Cheil Ind Inc POLYCARBONATE POLYSILOXAN COPOLYMER RESIN COMPOSITION HAVING HIGH RESISTANCE TO CHIP AND MECHANICAL STRENGTH
WO2024036052A1 (en) 2022-08-09 2024-02-15 Exxonmobil Chemical Patents Inc. Methods for preparing diphenylsilane bridged c1 symmetric catalysts and polymers made therefrom
CN115975205A (zh) * 2023-01-29 2023-04-18 厦门弘嘉顺逸科技有限公司 一种自乳化氨基硅油的制备方法和氨基硅油乳液
CN115975205B (zh) * 2023-01-29 2023-11-17 厦门弘嘉顺逸科技有限公司 一种自乳化氨基硅油的制备方法和氨基硅油乳液

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Publication number Publication date
EP1203044B1 (de) 2003-10-01
JP2003505549A (ja) 2003-02-12
EP1203044A1 (de) 2002-05-08
AU6269000A (en) 2001-02-05
DE50003926D1 (de) 2003-11-06
US6664342B1 (en) 2003-12-16
ES2208375T3 (es) 2004-06-16

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