EP1485519B1 - Composition et procede de revetement de substrat metallique - Google Patents

Composition et procede de revetement de substrat metallique Download PDF

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Publication number
EP1485519B1
EP1485519B1 EP20030727594 EP03727594A EP1485519B1 EP 1485519 B1 EP1485519 B1 EP 1485519B1 EP 20030727594 EP20030727594 EP 20030727594 EP 03727594 A EP03727594 A EP 03727594A EP 1485519 B1 EP1485519 B1 EP 1485519B1
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Prior art keywords
weight
coating composition
film
composition according
coating
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Expired - Lifetime
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EP20030727594
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German (de)
English (en)
French (fr)
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EP1485519A2 (fr
Inventor
Jean-Marie Poulet
Alain Chesneau
Georges Leger
Denis Begue
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NOF Metal Coatings Europe
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Dacral SA
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    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
    • C23C22/05—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions
    • C23C22/60—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using alkaline aqueous solutions with pH greater than 8
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
    • C23C22/05—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions
    • C23C22/60—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using alkaline aqueous solutions with pH greater than 8
    • C23C22/66—Treatment of aluminium or alloys based thereon
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C2222/00—Aspects relating to chemical surface treatment of metallic material by reaction of the surface with a reactive medium
    • C23C2222/20—Use of solutions containing silanes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31678—Of metal

Definitions

  • the present invention relates to a metal substrate coating composition based on an aqueous solution of sodium silicate and / or potassium.
  • the present invention also relates to methods of applying this composition to said metal substrate and to the various uses of this coating composition.
  • the coating composition is intended to be applied to a steel substrate having a free outer surface consisting of a metal layer of zinc or zinc-based alloy.
  • said metal layer may have been deposited on said steel substrate electrolytically or by hot dipping.
  • the metal surface treatment is subjected to multiple constraints of both technical nature; economic and environmental.
  • Sheet metal coils are produced by steelmakers using very fast processes, with line speeds ranging from a few m / min up to 250 m / min.
  • the surface treatment technologies must accommodate these line speed constraints.
  • Technical difficulties can then arise if one wishes to maintain a good chemical reactivity between the substrate and the treatment products, but also in terms of film formation, if one wishes to obtain a good tension and a good homogeneity of the deposits. of movie.
  • Anti-corrosion treatment technologies usually use chromium-based products (hexavalent or trivalent) that are applied in one or more layers. However, these products are harmful to the environment and need to be replaced by non-environmental treatment products.
  • manufacturers are subject to economic constraints and thus seek compact treatments from formulations that are firstly prepared in an aqueous medium (and therefore do not require additional investment for the reprocessing of possible solvents. organic) and which allow the other hand the application of a single layer with a single drying.
  • on-line operating constraints also require products that are on the one hand mono-component (that is to say that do not require the preparation of a mixture of several products prior to industrial implementation) and which are, on the other hand, stable over time (that is to say, with a lifespan greater than 3 weeks to accommodate the productions made by campaign).
  • the present invention relates to a composition that meets the requirements and constraints mentioned above.
  • the coating composition is intended to be applied to a metal substrate.
  • the wet film thus obtained is then dried and gives rise to a dry coating film.
  • the coating composition preferably contains 5 to 30% by weight of sodium and / or potassium silicate (s), more preferably 5 to 20% by weight of sodium and / or potassium silicate (s), even more preferentially 8 to 15% by weight of sodium silicate (s) and / or potassium and / or lithium.
  • this coating composition can be prepared in the form of a concentrate in which the percentage of sodium and / or potassium silicate (s) can reach up to approximately 40% by weight, or else in the form of a powder in which the percentage sodium silicate (s) and / or potassium may be up to about 80% by weight.
  • This sodium silicate solution may also contain a small proportion of Na 2 CO 3 of the order of 0.1% by weight relative to the weight of the silicate solution.
  • the present invention also relates to the dry coating film obtainable from the application method (described below) of the coating composition on a metal substrate.
  • This dry film of coating is characterized in that it comprises at least 40% by weight of dry matter of sodium silicate (s) and / or potassium preferably between 60% and 99.9% by weight relative to the total weight of dry film coating.
  • tensioning agent means an additive whose function is to lower and control the liquid surface energy of the composition (or surface tension).
  • Surface energy is the energy required to bring the molecules of the liquid interior of the composition to its surface. The lower the surface energy of the composition, the greater the wettability of the surface of the metal substrate. Wettability is the ability for said substrate to receive a liquid allowing it to spread over the largest possible area.
  • the surface energy of the composition is preferably adjusted to obtain good wettability of the surface to be coated under high line speed conditions before the product is frozen upon entering the drying zone.
  • the coating composition contains between 0.01 and 1% by weight of a tensioning agent, preferably about 0.1% by weight of a tensioning agent.
  • a coating composition having a surface tension value of between 20 and 50 Dynes.cm -1 (20mN.m -1 and 50mN.m -1 ), preferably between 22 and 45 Dynes.cm -1 ( 22mN.m -1 and 45mN.m -1 ), more preferably between 22 and 40 Dynes.cm -1 (22mN.m -1 and 40mN.m -1 ).
  • the tensioning agent may be added separately or on the occasion of the incorporation of another component containing such an agent, for example a dispersion or an emulsion of a polymer.
  • voltage agent may be mentioned polypropylene glycol and polyethylene glycol copolymers (such as Pluronic ® PE 3100 manufactured by BASF), silicone resins (such as ® BYK348, manufactured by BYK) , acetylenic glycols (such as Dynol604 ® , manufactured by Air Products), anionic and nonionic mixtures (such as Dapro W95 HS ® , marketed by Elementis), ammonium quaternary alcohols (such as Cycloquart ® , made by Clariant), modified polyethoxylated alcohols (such as Triton DF16 ® , manufactured by Union Carbide), and their compatible blends.
  • polypropylene glycol and polyethylene glycol copolymers such as Pluronic ® PE 3100 manufactured by BASF
  • silicone resins such as ® BYK348, manufactured by BYK
  • acetylenic glycols such as Dynol604 ® , manufactured by Air Products
  • the tensioning agent can be added to the composition according to the present invention in the form of an aqueous solution, a dispersion or an emulsion in water, with or without a co-solvent.
  • the water used in the coating composition according to the present invention is first subjected to a deionization process such that the conductivity of this water is approximately less than 20 ⁇ S / cm.
  • the pH of the coating composition is between 11 and 13, more preferably between 11 and 12.
  • the coating composition may further contain a polymer whose function is to lower the glass transition temperature of the dry coating film.
  • the presence of said polymer imparts elasticity and flexibility properties to the dry film of coating thus obtained. Said polymer then makes it possible to reduce or eliminate the appearance of cracks in the dry coating film, during a subsequent mechanical deformation of the metal substrate.
  • said polymer in particular may be mentioned acrylic polymers or copolymers such as Polysol M-19 ® (manufactured by SHOWA Highpolymer Co. Ltd.) or Rhodopas ® D-20 40 (manufactured by Rhodia), polyurethanes alkyds, epoxy esters, as well as their compatible mixtures.
  • acrylic polymers or copolymers such as Polysol M-19 ® (manufactured by SHOWA Highpolymer Co. Ltd.) or Rhodopas ® D-20 40 (manufactured by Rhodia), polyurethanes alkyds, epoxy esters, as well as their compatible mixtures.
  • said polymer may be added to the composition according to the present invention in the form of a dispersion or an emulsion in water or an aqueous solution, in a proportion which allows advantageously up to 60% by weight of the dry coating film.
  • said polymer can at the same time provide the composition with the previously mentioned tensioning agent.
  • the coating composition additionally contains an additive making it possible to increase the hydrophobicity of the dry coating film, in a proportion which makes it possible to reach up to 50% by weight of the dry film of coating, preferably up to 25% by weight of the dry film coating.
  • This additive is a silane, preferably chosen from di- or trimethoxysilanes, or functionalized di- or triethoxysilanes, and mixtures thereof.
  • the organic functionality can be vinyl, amine or oxyrane (epoxy) type.
  • the silane is chosen from epoxy functional silanes such as beta- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 4 (trimethoxysilyl) 1,2-butane-epoxide or gamma-glycidoxypropyltrimethoxysilane.
  • the silane may also act as a binder, a stabilizer for the coating composition, and may increase the corrosion resistance of the dry coating film.
  • silanes can be used independently or in combination in prehydrolysed form or not.
  • silane may also be associated with the addition of Titanate or Zirconate to enhance the crosslinking of the binder system depending on the characteristics required of the coating.
  • the increase in the hydrophobicity of the dry film coating can be observed visually, especially during cyclic corrosion tests (DIN 50017KTW), by the formation of droplets of condensed water vapor (from the electrolyte) less spread only in the case of a coating whose binder is only composed of silicate.
  • the hydrophobicity of the dry coating film by introducing the silane into the coating composition allows a lower dry film thickness to be applied for the same corrosion resistance result.
  • the coating composition may furthermore contain an additive making it possible to reduce the free surface alkalinity of the dry coating film, in a proportion which advantageously makes it possible to attain up to 25% by weight. dry film coating.
  • This additive is preferably a cerium (Ce) salt, a Lanthanum salt (La), a molybdenum salt (Mo), molybdic acid, para-toluenesulphonic acid and their salts, or a polyol such as as glycerol, as well as their mixtures.
  • the coating composition may furthermore contain an additive making it possible to increase the anticorrosion properties of the dry coating film, in a proportion which advantageously makes it possible to attain up to 25% by weight of the film dry coating.
  • This additive is preferably a mineral binder such as a titanate or a zirconate, and mixtures thereof.
  • the coating composition may further contain a lubricating agent.
  • a lubricating agent such as synthetic organic polymers such as polytetrafluoroethylene, polyethylene, polyethylene glycol or natural organic polymers such as carnauba wax or paraffins, as well as mixtures thereof.
  • the lubricant is added to the coating composition in a proportion which advantageously makes it possible to attain up to 15% by weight of the dry coating film, preferably between 1.5 and 15% by weight of the dry coating film, more preferably between 3 and 15% by weight of the dry film of coating, even more preferably between 5 and 15% by weight of the dry film coating.
  • the lubricant may require a stabilizer to avoid phase separation in the coating composition.
  • organophilic clays natural or synthetic
  • silica derivatives cellulose derivatives
  • xanthan gum or associative thickeners of polyurethane or acrylic type, and mixtures thereof.
  • the stabilizer is added to the coating composition according to the present invention in a proportion that achieves between about 0.1 to 5% by weight of the dry coating film.
  • the coating composition may additionally be added with an antifoam agent chosen in a manner compatible with the other constituents of the coating composition and the optimal amount of which is determined according to the conventional experiments of routines known to those skilled in the art.
  • said composition may be substantially free of organic solvent.
  • organic solvents have proven, in practice, to be incompatible with sodium and / or potassium silicates, the main constituents of the coating composition.
  • the present invention also relates to a method of coating a metal substrate which comprises applying the previously described coating composition to the surface of said substrate.
  • the application of the coating composition described above is carried out during an operation which consists in depositing a wet film of said composition, of suitable low thickness, followed by a drying operation of said composition.
  • metal substrate thus coated, giving rise to a dry coating film of said substrate.
  • the wet film thickness of the coating composition deposited on the metal substrate is between 0.3 and 39 ⁇ m, preferably between 0.3 and 30 ⁇ m and the wet film is applied at a rate of 0.6 to 40 g / m 2 , preferably 0.6 to 24 g / m 2 .
  • the method which is the subject of the present invention can be carried out online, after the metal coating step of zinc or zinc-based alloy of the steel substrate, or on a recovery line such as on a pre-lacquering line (" coil-coating ").
  • the operation of depositing the wet film of the coating composition on the metal substrate can advantageously be carried out by spraying, spraying followed by a spinning operation, by soaking followed by spinning operation or by means of a coating system composed of at least one roller.
  • the spinning operation makes it possible to control the thickness of the wet film deposited on the metal substrate.
  • This spinning operation can be advantageously carried out using a set of spinning rolls.
  • the drying operation of the metal substrate coated with the wet film is carried out by heating the metal substrate or the wet wire so as to bring the latter to a temperature of between room temperature and room temperature. ° C.
  • the heating operation can be performed directly by induction, or indirectly by convection or infrared. Convection heating generally requires a longer drying time than induction heating or infrared heating.
  • This drying operation is advantageously carried out by heating the metal substrate or the wet film so as to bring the latter preferably to a temperature of at least about 35 ° C for a period of at least 2 seconds if heating is used. convection and for a maximum duration of 10 seconds, preferably 5 seconds, plus preferably from 1 to 2 seconds, if induction or infrared heating is used.
  • the drying operation is carried out in order to obtain a dry film thickness of coating of between 0.05 and 0.80 ⁇ m, preferably between 0.05 and 0.60 ⁇ m and so as to obtain a weight of dry film coating layer between 0.1 g / m 2 and 1.3 g / m 2 , preferably between 0.2 g / m 2 and 1.2 g / m 2 , more preferably between 0.2 to 0.5 g / m 2 .
  • the wet film deposition and drying operations are carried out between zinc or zinc alloy metal coating operations of the steel substrate and final winding.
  • the present invention also relates to the various uses of the coating composition object of the present invention.
  • the coating composition can be used as a corrosion protection layer of metal sheets when it is applied to said sheets.
  • said composition may be used as an anti-corrosion protection layer for metal sheets intended to be temporarily stored.
  • a layer of dry coating film according to the present invention when it has been applied to a metal substrate and then dried at 240 ° C., completely resists said soak baths. degreasing.
  • said layer of dry coating film is partially solubilized by the degreasing baths and when it has been dried at 50 ° C., it is completely solubilized by the degreasing baths.
  • the coating composition can be used as a lubricating layer when it further contains a lubricant and is applied to metal sheets for shaping, particularly for folding, bending and stamping said metal sheets.
  • the coating composition may be used as an anti-fingerprint agent.
  • metal sheets coated with the coating composition object of the present invention can be handled as is, without fingerprints remaining subsequently printed on said metal sheets.
  • the coating composition may be applied to metal substrate parts to be welded.
  • said substrates thus coated retain their weldability property and the welding operations can be done directly.
  • the coating composition may require the addition of conductive pigments such as iron phosphide, ammonium silicate, nickel, tungsten, zinc (pure or alloyed) and carbon, as well as their mixtures.
  • conductive pigments such as iron phosphide, ammonium silicate, nickel, tungsten, zinc (pure or alloyed) and carbon, as well as their mixtures.
  • Comparative Example 5 Surface energy of the coating composition as a function of the tensioning agent.
  • the test consists of subjecting the metal substrate sample to a friction over a length of about 50 mm (see FIG. figure 1 ).
  • the samples have a size of 50 mm x 200 mm and are processed on both sides.
  • a lateral force (F L ) is imposed on the sample and it is subjected to a constant speed pull of 20 mm / min.
  • the tensile force F T is measured after a friction distance of 50 mm.
  • the measurement temperature is 21 ⁇ 2 ° C.
  • the coating dry film layer weights deposited on the metal substrate samples are between 1 and 1.2 g / m 2 .
  • the reference sample is an electrogalvanised sheet (7.5 ⁇ m on each face) on which a layer of ANTICORRIT 4107 S® oil (manufacturer FUCHS) has been applied at a height of 2.5 g / m 2 on each face .
  • This oil is widely used in the automotive industry as a lubricant for sheet metal for stamping.
  • composition of dry coating film Composition of the lubricating agent contained in the composition of the dry coating film (percentages expressed by weight of dry matter) ⁇ (B1) 75% PTFE 0.18 25% PEG (B2) 50% PTFE 0.176 50% PEG (B3) 25% PTFE 0.177 25% PEG 50% PE (B4) 17% PTFE 0.169 50% PEG 33% PE (B5) 34% PTFE 0.178 66% EP (B6) 100% PEG 0.203
  • the coefficients of friction of the samples coated with a dry film of composition according to the present invention (B1) to (B6) are lower than the coefficient of friction of the reference sample. This indicates that lubrication of the dry film-coated samples of the present invention (B1) to (B6) is better than that of the reference sample.
  • Sample hot-dip galvanized steel (10 ⁇ m) Sample of hot-dip galvanized steel (10 ⁇ m) coated with a dry film of coating according to composition (A) with a weight of layer equal to: 0.3 g / m 2 0.6 g / m 2 0.9 g / m 2 1.2 g / m 2 Humidotherm test (duration 15 cycles) performed according to DIN 50017 White rust on 100% of the surface (after 5 cycles only) Change in appearance: White rust on 70% of the surface No appearance changes No appearance changes No appearance changes No appearance changes Salt spray test (48 hours duration) according to ISO 9227 White rust on 100% of the surface (after 24 hours only) White rust on 60% of the surface White rust on 20% of the surface White rust on less than 5% of the surface No appearance changes
  • Example 7 Results of a formulation comprising a silane
  • composition of the coating (E) % mass sodium silicate 20N32 ® 29.7 silane gamma glycidoxypropyltrimethoxysilane 3.73 Pluronic PE 3100 ® 0.07 Water 66.5
  • Test DIN 50017KTW (20 cycles) Hot-dip galvanized steel substrate (10 ⁇ m) coated with a dry coating film according to composition (A) or (E) with a coating weight of: 0.2 g / m 2 0.5 g / m 2 0.65 g / m 2 Formulation (A) Change in appearance: white rust on 90% of the surface Change in appearance: white rust on 50% of the surface Very slight change in appearance: white rust on 15% of the surface Formulation (E) Very slight change in appearance: white rust on 20% of the surface No change in appearance No change in appearance No change in appearance No change in appearance No change in appearance
  • composition comprising the silane is more effective against corrosion than the silane-free composition.
  • introduction of silane thus makes it possible to reduce the weight of the layer while maintaining the same anticorrosion properties.

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  • Chemical & Material Sciences (AREA)
  • Metallurgy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Laminated Bodies (AREA)
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EP20030727594 2002-03-18 2003-03-18 Composition et procede de revetement de substrat metallique Expired - Lifetime EP1485519B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP20100159057 EP2208809B9 (fr) 2002-03-18 2003-03-18 Composition et procede de revetement de substrat metallique

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0203353A FR2837218B1 (fr) 2002-03-18 2002-03-18 Composition de revetement de substrat metallique
FR0203353 2002-03-18
PCT/FR2003/000863 WO2003078683A2 (fr) 2002-03-18 2003-03-18 Composition et procede de revêtement de substrat métallique

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EP20100159057 Division EP2208809B9 (fr) 2002-03-18 2003-03-18 Composition et procede de revetement de substrat metallique
EP10159057.8 Division-Into 2010-04-02

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EP1485519A2 EP1485519A2 (fr) 2004-12-15
EP1485519B1 true EP1485519B1 (fr) 2010-05-19

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US (1) US7232479B2 (es)
EP (2) EP1485519B1 (es)
AT (1) ATE468424T1 (es)
AU (1) AU2003233381A1 (es)
BR (1) BR0308562A (es)
CA (1) CA2479060C (es)
DE (1) DE60332605D1 (es)
ES (2) ES2343244T3 (es)
FR (1) FR2837218B1 (es)
MX (1) MXPA04009082A (es)
WO (1) WO2003078683A2 (es)

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EP2208809B1 (fr) 2013-06-12
AU2003233381A8 (en) 2003-09-29
WO2003078683A3 (fr) 2004-06-03
US7232479B2 (en) 2007-06-19
ATE468424T1 (de) 2010-06-15
DE60332605D1 (de) 2010-07-01
WO2003078683A2 (fr) 2003-09-25
AU2003233381A1 (en) 2003-09-29
US20060086281A1 (en) 2006-04-27
FR2837218A1 (fr) 2003-09-19
ES2423317T3 (es) 2013-09-19
CA2479060A1 (fr) 2003-09-25
FR2837218B1 (fr) 2005-02-18
MXPA04009082A (es) 2004-12-06
WO2003078683A9 (fr) 2004-07-15
ES2343244T3 (es) 2010-07-27
EP2208809A1 (fr) 2010-07-21
EP1485519A2 (fr) 2004-12-15
CA2479060C (fr) 2011-05-24
EP2208809B9 (fr) 2014-11-12
BR0308562A (pt) 2005-01-04

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