EP1413653B1 - Fibre âme-gaine conductrice, resistant à la salissure et aux produits chimiques, procédé de fabrication et utilisation - Google Patents

Fibre âme-gaine conductrice, resistant à la salissure et aux produits chimiques, procédé de fabrication et utilisation Download PDF

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Publication number
EP1413653B1
EP1413653B1 EP03021088A EP03021088A EP1413653B1 EP 1413653 B1 EP1413653 B1 EP 1413653B1 EP 03021088 A EP03021088 A EP 03021088A EP 03021088 A EP03021088 A EP 03021088A EP 1413653 B1 EP1413653 B1 EP 1413653B1
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EP
European Patent Office
Prior art keywords
melt
core
sheath
polymer
weight
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EP03021088A
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German (de)
English (en)
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EP1413653A3 (fr
EP1413653A2 (fr
Inventor
Hans-Joachim Brüning
Herbert Hofmann
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Teijin Monofilament Germany GmbH
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Teijin Monofilament Germany GmbH
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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/09—Addition of substances to the spinning solution or to the melt for making electroconductive or anti-static filaments
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
    • D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
    • D01F8/12—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyamide as constituent
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
    • D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
    • D01F8/14—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyester as constituent

Definitions

  • the present invention relates to conductive soil-repellent core-sheath fibers, in particular monofilaments, which can be used in particular in technical fabrics.
  • melt-spinnable fluoropolymers have good thermal stability, good chemical resistance and dirt-repellent properties. It has already been attempted to process melt-spinnable fluoropolymers into fibers, multi- and monofilaments in order to produce textile surfaces for technical applications with the above-mentioned properties of fluoropolymers.
  • a disadvantage of melt-spinnable fluoropolymers is the high creep behavior. Fibers and filaments of this material therefore have only low tensile strengths and are not dimensionally stable.
  • fluoropolymers have good mechanical performance properties, e.g. with polyethylene terephthalate (hereinafter also referred to as "PET").
  • PET polyethylene terephthalate
  • fluoropolymers are often incompatible with other polymers and generally do not mix. Thus, a two-phase mixture often arises in which the fluoropolymers form spatial islands. The proportion by weight of fluoropolymer which can be metered in is thus frequently limited, since the boundary layers of the polymers adhere only poorly to one another. In fibers, this property is noticeable as a "splice tendency".
  • the electrically conductive fibers may include electrically conductive particles such as carbon black or metal particles, metal coatings, or may be made of electrically conductive materials such as polyanilines. As fiber materials polyester and polyolefins are described.
  • yarns are known for making spiral tapes coated with a layer of thermosetting polymers.
  • This layer contains electrically conductive carbon.
  • polymers for the cladding layer melamine resins, epoxies, phenolic resins or polyurethanes are exemplified.
  • the DE-A-39 38 414 describes high-strength fabrics of synthetic fibers, which are woven in the form of electrically conductive fibers in warp and weft, and continue to contain electrically non-conductive fibers.
  • the electrically conductive fibers consist of polyolefins and contain graphite or carbon black.
  • the EP-A-160.320 describes core-shell monofilaments for use in hairbrushes of selected polymers.
  • the core contains nylon or polyester comprising at least 60% by weight of polybutylene terephthalate units.
  • the jacket contains special types of nylon or copolyetherester.
  • Core sheath fibers are known, the core of thermoplastic material, preferably of polyamide, and their sheath of electrically conductive plastic, preferably of polyamide, which contains soot or metals embedded.
  • the JP-A-07 / 278.956 describes electrically conductive copolyesters containing mainly polybutylene terephthalate units doped with carbon black. It also describes core-sheath fibers of this material in which the core is made of aromatic polyester.
  • electrically conductive heterofilaments are known, which may be configured, for example, as core-sheath fibers.
  • core and sheath polymers PET and other polyesters or PET / nylon are described.
  • the WO-A-01 / 20.076 discloses nonwovens with high dielectric constant.
  • fiber material mixtures of polyvinylidene fluoride and polypropylene are proposed.
  • the resulting products are characterized by a prolonged half-life of electrostatic charges and can be used as electrostatic filters.
  • the US-A-6,085,061 describes a brush for cleaning electrostatically charged surfaces.
  • core-sheath fibers can be used, the core of which is electrically conductive and whose sheath consists of polyvinylidene fluoride.
  • melt-spun undrawn, electrically nonconductive core-sheath fibers whose sheaths contain fluoropolymers are known.
  • the core polymer used is polycarbonate.
  • This fiber is used as an optical fiber and is not suitable because of the low strength for technical textiles, such as technical fabrics.
  • high reflection at the boundary layer and the lowest possible attenuation of the electromagnetic wave are important. Both properties can only be achieved by using a high-purity coating.
  • a semiconducting fiber of a carbon black-containing fluoropolymer will be described.
  • This fiber has no core-shell structure and is used for the production of non-wovens, for example by the melt-blow process. The fiber is not stretched.
  • the prioritized, not pre-published WO-A-03/004738 describes core-sheath fibers of high strength and good chemical resistance.
  • the sheath of the fibers contains a fluoropolymer.
  • Combinations of PET as core material and PVDF as cladding material are described.
  • This document also discloses in a general way the possibility of adding additives in core or shell. Possible additives include electrically conductive materials.
  • the present invention has the object to combine the performance advantages of the known materials for fiber production without having to accept the disadvantages associated with the use of the individual materials in purchasing.
  • Another object of the present invention is thus to provide core-sheath fibers with good adhesion between the individual layers.
  • the present invention thus provides fibers, in particular monofilaments, which combine antistatic properties with high chemical and chemical properties have thermal resistance and good mechanical dimensional stability and high tensile strength.
  • the invention relates to a melt spun fiber having a core-sheath structure and a tensile strength of at least 15 cN / tex, the core of which contains a melt-spinnable synthetic thermoplastic polymer having a first melting point which is not a fluoropolymer and whose sheath comprises at least one melt-spinnable fluoropolymer having a second melting point , which is at least 20 ° C below the first melting point, and contains particles of electrically conductive material, the amount of which is up to 50 wt.%, Based on the amount of the shell material.
  • the core thermoplastic synthetic polymers can be of any nature as long as they are melt-spun and impart the fiber with the properties desired for the particular application. Fluoropolymers are not included in the synthetic thermoplastic polymers, although the core may also contain fluoropolymers as the blending component in addition to these polymers.
  • thermoplastic materials are polyolefins such as polyethylene, polypropylene or copolymers containing ethylene and / or propylene units in conjunction with other alpha-olefin units copolymerized therewith, such as alpha-butylene, alpha-pentylene, alpha-hexylene or alpha-octylene; Polyesters such as polycarbonate, aliphatic / aromatic polyesters or wholly aromatic polyesters; Polyamides, such as aliphatic or aliphatic / aromatic polyamides (nylon types) or wholly aromatic polyamides (aramids); or polyether ketones, ie polymers which have at least ether and ketone groups and, as a rule, aromatic divalent radicals, such as phenylene, in the recurring chain, many combinations of these groups being possible, for example PEK, PEEK or PEKK; or polyarylene sulfides, preferably polyphenylene sulfide; or polyether esters, ie polyole
  • the core of the core-sheath fibers according to the invention contains polyamides and in particular polyesters.
  • thermoplastic polyamides which are preferably used in the compositions according to the invention are known per se.
  • thread-forming polyamides such as aliphatic or aliphatic / aromatic polyamides, e.g. Polycaprolactam, poly (hexamethylene-1,6-diaminadipamide), poly (hexamethylene-1,6-diamine-sebacic acid diamide), poly (hexamethylene-1,6-diamine-terephthalic acid diamide) or poly (hexamethylene) -1,6-diamine isopthalklarediamid); or completely aromatic polyamides, such as poly (phenylene-1,4-diamine-terephthalic acid diamide) or poly (phenylene-1,4-diaminisophthalic acid diamide).
  • polycaprolactam poly (hexamethylene-1,6-diaminadipamide), poly (hexamethylene-1,6-diamine-sebacic acid diamide), poly (hexamethylene-1,6-diamine-terephthalic acid diamide) or poly (hexamethylene) -1,6
  • the polyamides used according to the invention usually have viscosity numbers according to DIN 53727 of 120 to 350, preferably 150 to 320 cm 3 / g (measured at 25 ° C in sulfuric acid).
  • thermoplastic polyesters and / or aromatic liquid-crystalline polyesters which are particularly preferably used in the compositions according to the invention are known per se.
  • polyesters such as polycarbonate or aliphatic / aromatic polyesters, such as polybutylene terephthalate, polycyclohexanedimethyl terephthalate, polyethylene naphthalate or especially polyethylene terephthalate, but also completely aromatic, liquid crystalline polyesters, such as Polyoxibenzonaphtoat.
  • Building blocks of thread-forming polyesters are preferably diols and dicarboxylic acids, or appropriately constructed oxycarboxylic acids.
  • the main acid constituent of the polyesters is terephthalic acid or cyclohexanedicarboxylic acid, but other aromatic and / or aliphatic or cycloaliphatic dicarboxylic acids may also be suitable, preferably para or trans aromatic compounds, for example 2,6-naphthalenedicarboxylic acid or 4,4'-biphenyldicarboxylic acid , but also p-hydroxy-benzoic acid.
  • aliphatic Dicarboxylic acids such as adipic acid or sebacic acid are preferably used in combination with aromatic dicarboxylic acids.
  • Typical suitable dihydric alcohols are aliphatic and / or cycloaliphatic and / or aromatic diols, for example ethylene glycol, propanediol, 1,4-butanediol, 1,4-cyclohexanedimethanol but also hydroquinone.
  • thermoplastic polyesters are in particular selected from the group consisting of polyethylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polypropylene terephthalate, polybutylene terephthalate, polycyclohexanedimethanol terephthalate, polycarbonate or a copolycondensate comprising polybutylene glycol, terephthalic acid and naphthalenedicarboxylic acid units.
  • thermoplastic polyesters are aromatic, liquid-crystalline polyesters, in particular polyesters containing p-hydroxybenzoate units.
  • polyesters which are to be used in moist-hot environments, as in the case of monofilaments used in paper machines, and which contain polyester as the core component, these polyesters are preferably stabilized against hydrolytic degradation by addition of polyester stabilizers.
  • Such stabilized fibers show a significant reduction in the level of degradation of the polyester, so that life of monofilaments equivalent to monofilaments based on highly durable fiber materials such as polyarylene sulfides or oxides can be achieved.
  • fibers comprising core-stabilized polyesters, more preferably carbodiimides.
  • the polyesters used according to the invention usually have solution viscosities (IV values) of at least 0.60 dl / g, preferably from 0.60 to 1.05 dl / g, particularly preferably from 0.62 to 0.93 dl / g ( measured at 25 ° C in dichloroacetic acid (DCE)).
  • IV values solution viscosities
  • the mantle-forming fluoropolymers may also be of any nature as long as they are melt-spun and have a melting point that is at least 20 ° C below the melting point of the thermoplastic polymer of the core.
  • the fluoropolymers used in the present invention are poly (fluoroolefin) homopolymers and / or copolymers derived from ethylenically-unsaturated fluorine-containing olefin monomers and other monomers copolymerizable therewith. Such polymers are also known per se.
  • melt-spinnable copolymers of tetrafluoroethylene with other alpha-olefins such as ethylene, propylene, butylene, hexylene or octylene.
  • homopolymers or copolymers derived from other fluorine-containing monomers for example from mono-, di- or trifluoroethylene, from vinyl fluoride or in particular from vinylidene fluoride.
  • Particular preference is given to using melt-spinnable copolymers of tetrafluoroethylene with at least one alpha-olefin, preferably with ethylene.
  • PVDF polyvinylidene fluoride
  • the invention therefore also relates to a heterafilamentary fiber containing at least two components, wherein the first component is an electrical insulator and a thermoplastic polymer which is not a fluoropolymer and the second component comprises polyvinylidene fluoride.
  • the particles of electrically conductive material present in the cladding of the melt-spun fiber according to the invention may be of any nature, as long as they impart increased electrical conductivity to the cladding.
  • These may be particles of carbon, for example carbon fibers, carbon black or graphite; of metals, such as copper, silver, aluminum or iron; of metal alloys, for example of bronze; or of conductive plastics, for example polyanilines or polypyrrole.
  • the particles may be in any form, for example in fibrous form or in the form of round or irregular particles.
  • the content of the electrically conductive particles in the cladding should be chosen such that there is a significant increase in the electrical conductivity of the plastic material. Typical amounts are in the range of up to 50% by weight, preferably 2 to 15% by weight, based on the amount of shell material.
  • melt-spun fibers in which the sheath contains between 2% by weight and 15% by weight, in particular between 4% by weight and 9% by weight, of electrically conductive particles.
  • the core-sheath fibers according to the invention can be present in any desired form, for example as multifilaments, as staple fibers or in particular as monofilaments.
  • the titer of the core-sheath fibers according to the invention can likewise vary within wide limits. Examples are 100 to 45,000 dtex, in particular 400 to 7,000 dtex.
  • the staple lengths of staple fibers can also vary widely, for example between 30 to 70 mm.
  • the core of the core-sheath fiber according to the invention forms the mechanical support of the fiber, while the sheath mainly determines the performance characteristics, such as antistatic behavior and sliding behavior.
  • the core used may preferably be a commercially available PET raw material.
  • a fluoropolymer based on PVDF is particularly preferably used which has been previously processed, in particular with carbon black, into a spinnable mixture.
  • the two polymers or mixtures containing these polymers are preferably dried immediately before being fed into the extruder, melted in the extruder and filtered through a spin pack.
  • the fluoropolymer is provided with the electroconductive particles. This is usually done before the delivery of the fluoropolymer to the extruder, but can also take place immediately before the spin pack. It is also possible to use masterbatches comprising the fluoropolymer and electrically conductive particles.
  • the molten polymer filament is cooled in a spin bath, for example a water bath, and then wound or drawn off.
  • the removal speed is greater than the injection rate of the polymer melt and thus causes a stretching of the formed thread.
  • the heterofilament spun yarn produced in this way is then preferably subjected to a post-drawing, more preferably in several stages, in particular a two- or three-stage post-drawing, with a total draw ratio of 1: 3 to 1: 8, preferably 1: 4 to 1: 6.
  • the spinning take-off speed is usually 10 to 40 m per minute.
  • thermoplastic polymer of the core and the fluoropolymer of the shell When spinning the thermoplastic polymer of the core and the fluoropolymer of the shell to a bicomponent monofilament core-sheath structure surprisingly shows a very good core-shell adhesion.
  • the conductivity of the jacket may be lost during stretching, but may be restored by a heat treatment and the shrinkage caused thereby, preferably above the melting point of the jacket material but below the melting temperature of the core.
  • the conductively doped fluoropolymer mainly determines the surface properties.
  • the fibers of the invention are characterized by very good dirt repellency, good chemical resistance and electrical conductivity.
  • the combination with the fluoropolymer results in fibers with improved slip properties compared to pure thermoplastic polymer fibers. These fibers show increased soil repellency compared to pure thermoplastic polymer fibers.
  • the fibers according to the invention may contain auxiliaries in addition to the components A) and B).
  • auxiliaries include processing aids, stabilizers, antioxidants, plasticizers, lubricants, pigments, matting agents, viscosity modifiers or crystallization accelerators.
  • processing aids are siloxanes, waxes or longer-chain carboxylic acids or their salts, aliphatic, aromatic esters or ethers.
  • stabilizers and antioxidants are the polyester stabilizers already mentioned above, phosphorus compounds such as phosphoric acid esters or carbodiimides.
  • pigments or matting agents examples include organic dye pigments or titanium dioxide.
  • viscosity modifiers are polybasic carboxylic acids and their esters or polyhydric alcohols.
  • the fibers according to the invention are preferably used for the production of textile fabrics, such as fabrics, knitted fabrics, crocheted, laid and nonwovens.
  • Textile fabrics comprising monofilaments according to the invention are particularly suitable for technical applications, such as for filters, as screen printing materials or in particular as paper machine screens.
  • the monofilaments according to the invention have good textile-physical properties and can be easily interwoven.
  • the fabrics have the usual dimensional stability of the core forming thermoplastic polymers.
  • Fabrics made of these monofilaments are excellently suited for technical fabrics, in particular in the filtration of aggressive media, which are also at risk of electrostatic charge; i.e. especially in the solid-gaseous and solid-liquid filtration.
  • the invention also relates to the use of the fibers for making fabrics used in environments of high chemical and / or physical stress, in particular as paper machine fabrics or as technical fabrics, e.g. used in filtration, for the production of conveyor belts or as reinforcing inserts.
  • the fibers are used as monofilaments and in particular as weft threads in the fabric.
  • the use of the monofilaments according to the invention as papermaking fabrics may take place in the forming section, the press section or, in particular, in the dryer section respectively.
  • the monofilaments according to the invention are used in particular as spiral sieves.
  • the fibers used according to the invention in particular in the form of monofilaments, usually have a titer range of 10 to 4500 tex, a modulus of elasticity of 2.0 to 8.0 N / tex, a tenacity of 15 to 50 cN / tex Elongation at break of 15 to 45% and hot air shrinkage at 180 ° C of 1.0 to 20.0%.
  • PET polyethylene terephthalate
  • PVDF polyvinylidene fluoride
  • the core-sheath monofilament obtained had the following properties: titres 2890 dtex strength 24 cN / tex HLS (hot air shrink 10 'at 160 ° C) 2.5% loop strength > 20 cN / tex elongation 44% BZD (reference strain at 12 cN / tex): 8.5% BZD (reference strain at 15 cN / tex): 13% EGG. Resistance (10 mm clamping length): 8 * 10 5 (ohms) EGG. Resistance (150 mm clamping length): 9 * 10 6 (ohms)

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Multicomponent Fibers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Laminated Bodies (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)

Claims (13)

  1. Fibre filée en fusion à structure âme-gaine et avec une résistance à la traction d'au moins 15 cN/tex, dont l'âme contient un polymère synthétique thermoplastique filable en fusion, avec un premier point de fusion, qui n'est pas un polymère fluoré, et dont la gaine contient au moins un polymère fluoré filable en fusion avec un deuxième point de fusion qui se trouve au moins 20 °C en dessous du premier point de fusion, et des particules en un matériau conducteur de l'électricité, dont la quantité s'élève à jusqu'à 50 % en poids, rapportés à la quantité du matériau de la gaine, sachant que l'âme constitue entre 50 et 95 % en poids et la gaine entre 50 et 5 % en poids, rapportés à la quantité totale de l'âme et de la gaine.
  2. Fibre filée en fusion selon la revendication 1, caractérisée en ce que le polymère thermoplastique synthétique de l'âme est un polyamide et en particulier un polyester.
  3. Fibre filée en fusion selon la revendication 2, caractérisée en ce que le polyester est un polyéthylène téréphtalate.
  4. Fibre filée en fusion selon la revendication 2, caractérisée en ce que le polyester est un polyester cristallin liquide.
  5. Fibre filée en fusion selon la revendication 1, caractérisée en ce que le polymère fluoré filable en fusion est un copolymère de tétrafluoréthylène avec au moins une alpha-oléfine, de préférence de l'éthylène.
  6. Fibre filée en fusion selon la revendication 1, caractérisée en ce que le polymère fluoré filable en fusion est un polyfluorure de vinylidène.
  7. Fibre filée en fusion selon la revendication 1, caractérisée en ce que la gaine contient de 2 à 15 % en poids de particules conductrices de l'électricité.
  8. Fibre filée en fusion selon la revendication 6, caractérisée en ce que la gaine contient entre 2 % en poids et 15 % en poids, en particulier entre 4 % en poids et 9 % en poids de particules conductrices de l'électricité.
  9. Fibre filée en fusion selon la revendication 1, caractérisée en ce que les particules de matériau conducteur de l'électricité consistent en carbone, en métaux ou en alliages de métaux, en particulier sont du noir de fumée ou du graphite.
  10. Fibre filée en fusion selon la revendication 1, caractérisée en ce que celle-ci est un filament, en particulier un monofilament.
  11. Procédé pour la production de la fibre filée en fusion à structure âme-gaine selon la revendication 1, comprenant les mesures:
    i) Choix d'un premier polymère qui est un polymère synthétique thermoplastique filable en fusion et n'est pas un polymère fluoré et présente un premier point de fusion,
    ii) Choix d'un deuxième polymère, qui est polymère fluoré filable en fusion qui présente un deuxième point de fusion qui se trouve au moins 20 °C en dessous du premier point de fusion, et qui contient des particules en un matériau conducteur de l'électricité, dont la quantité s'élève à jusqu'à 50 % en poids, rapportés à la quantité du matériau de la gaine,
    iii) Coextrusion du premier polymère et du deuxième polymère par une filière pour hétérofilaments à une température de filage au-dessus du premier point de fusion, de telle sorte qu'il se forme une fibre à deux composants avec une âme en le premier polymère et une gaine en le deuxième polymère, et
    iv) Étirement du filament âme-gaine formé pour l'augmentation de la résistance à la traction.
  12. Utilisation de fibres filées en fusion à structure âme-gaine selon la revendication 1 à la fabrication de tissus techniques.
  13. Utilisation selon la revendication 12, caractérisée en ce que le tissu technique est un tamis de machine à papier, un tissu filtrant, un tissu pour sérigraphie, une bande transporteuse ou une garniture de renforcement.
EP03021088A 2002-10-24 2003-09-18 Fibre âme-gaine conductrice, resistant à la salissure et aux produits chimiques, procédé de fabrication et utilisation Expired - Lifetime EP1413653B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10249585 2002-10-24
DE10249585A DE10249585B4 (de) 2002-10-24 2002-10-24 Leitfähige, schmutzabweisende Kern-Mantel-Faser mit hoher Chemikalienresistenz, Verfahren zu deren Herstellung und Verwendung

Publications (3)

Publication Number Publication Date
EP1413653A2 EP1413653A2 (fr) 2004-04-28
EP1413653A3 EP1413653A3 (fr) 2004-10-06
EP1413653B1 true EP1413653B1 (fr) 2009-02-11

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Country Link
US (1) US20040078903A1 (fr)
EP (1) EP1413653B1 (fr)
JP (1) JP2004143659A (fr)
AT (1) ATE422570T1 (fr)
DE (2) DE10249585B4 (fr)
DK (1) DK1413653T3 (fr)
ES (1) ES2321389T3 (fr)
PL (1) PL363021A1 (fr)
PT (1) PT1413653E (fr)

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JP2004143659A (ja) 2004-05-20
DE50311164D1 (de) 2009-03-26
DE10249585B4 (de) 2007-10-04
DK1413653T3 (da) 2009-05-11
EP1413653A3 (fr) 2004-10-06
EP1413653A2 (fr) 2004-04-28
ATE422570T1 (de) 2009-02-15
DE10249585A1 (de) 2004-05-13
PT1413653E (pt) 2009-04-29
US20040078903A1 (en) 2004-04-29
PL363021A1 (en) 2004-05-04

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