EP1851282A1 - Collage de thermoplastiques traites par plasma d'air - Google Patents

Collage de thermoplastiques traites par plasma d'air

Info

Publication number
EP1851282A1
EP1851282A1 EP06708196A EP06708196A EP1851282A1 EP 1851282 A1 EP1851282 A1 EP 1851282A1 EP 06708196 A EP06708196 A EP 06708196A EP 06708196 A EP06708196 A EP 06708196A EP 1851282 A1 EP1851282 A1 EP 1851282A1
Authority
EP
European Patent Office
Prior art keywords
plasma
air
adhesive
thermoplastic
substrate
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.)
Withdrawn
Application number
EP06708196A
Other languages
German (de)
English (en)
Inventor
Willy Arber
Patrick Frey
Mario Slongo
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.)
Sika Technology AG
Original Assignee
Sika Technology 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
Application filed by Sika Technology AG filed Critical Sika Technology AG
Priority to EP06708196A priority Critical patent/EP1851282A1/fr
Publication of EP1851282A1 publication Critical patent/EP1851282A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/414—Additional features of adhesives in the form of films or foils characterized by the presence of essential components presence of a copolymer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2400/00—Presence of inorganic and organic materials
    • C09J2400/20—Presence of organic materials
    • C09J2400/22—Presence of unspecified polymer
    • C09J2400/226—Presence of unspecified polymer in the substrate
    • 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]
    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]
    • 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]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • 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]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31935—Ester, halide or nitrile of addition polymer
    • 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]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31938—Polymer of monoethylenically unsaturated hydrocarbon

Definitions

  • the present invention is concerned with the bonding of thermoplastics.
  • primers so-called primers
  • cleaning with or swelling with solvent is often used. Due to occupational hygiene and safety reasons, however, such solvent-based pretreatments are often undesirable.
  • physical or physicochemical pretreatment processes are known, which are used to increase the adhesion. These include in particular the corona treatment, flaming and various plasma treatments. However, it has been found that the surfaces of these polymers undergo massive changes within hours after the pretreatment, as described, for example, by AJ.
  • thermoplastics have the great disadvantage that surfaces pretreated in such a way must be bonded within a short time after the pretreatment, the so-called “lying time”, in order to achieve reliable adhesion.
  • thermoplastic materials in such a way that they can be bonded in the long term.
  • This object has surprisingly been achieved by a method according to claim 1 and a use according to claim 14. Particularly preferred embodiments are specified in the subclaims.
  • thermoplastics treated with air plasma at atmospheric ambient pressure have an extraordinary elongation of the bondability and can surprisingly still be bonded during very long lay times, which may take up to years, even under different storage conditions, without the adhesive strength being markedly reduced.
  • the present invention relates to a method for bonding two substrates S1 and S2 by means of adhesives.
  • At least the substrate S1 is in this case a thermoplastic film, which is a copolymer CP of at least two monomers which are selected from the group comprising vinyl acetate, vinyl alcohol, styrene, ethylene, propylene, butadiene, esters of (meth) acrylic acid and mixtures thereof, or includes.
  • the method comprises the following steps
  • thermoplastic film S1 (i) treating the thermoplastic film S1 with an air plasma at atmospheric ambient pressure at least in the area to be bonded
  • Said copolymer CP consists of at least two monomers, in particular it is a copolymer CP of two or three of said monomers.
  • Preferred copolymers CP have proved to be those which are prepared from at least two monomers which are selected from the group comprising ethylene, vinyl acetate, (meth) acrylates, styrene, acrylonitrile and mixtures thereof.
  • the copolymer CP is preferably an amorphous thermoplastic.
  • Particularly preferred copolymers are ethylene / vinyl acetate copolymers (EVA) and (meth) acrylate / styrene / acrylonitrile copolymers. Most preferred is EVA.
  • EVA ethylene / vinyl acetate copolymers
  • ingredients to be present are, in addition to other thermoplastics, the usual components for films and processing agents, such as fillers, additives such as UV and heat stabilizers, plasticizers, lubricants lubricant, flame retardants, antioxidants, pigments and dyes.
  • films and processing agents such as fillers, additives such as UV and heat stabilizers, plasticizers, lubricants lubricant, flame retardants, antioxidants, pigments and dyes.
  • polyolefins in particular polyethylene, polypropylene and ethylene / propylene copolymers, are considered as further thermoplastics; Polyvinyl chloride, chlorinated polyolefins such as chlorinated polyethylenes (CPE), or chlorosulfonated polyethylenes.
  • CPE chlorinated polyethylenes
  • Polyethylene in particular polyethylene produced via metallocenes, and also chlorosulfonated polyethylenes have on the one hand particular preference as additional thermoplastics. Most preferred are chlorosulfonated polyethylenes, especially those commercially available under the trade name Hypalon® from DuPont.
  • the thermoplastics are preferably amorphous thermoplastics. Chalks, in particular coated chalks, carbon black, titanium dioxides, aluminum oxides, silicon oxides and silicates, preferably chalks, have proved to be fillers.
  • the films preferably have thicknesses of more than 0.5 mm, in particular of at least 1 mm, preferably between 1 and 5 mm, most preferably between 1 and 2 mm.
  • the film is preferably present in the form of a roll.
  • Films have proven to be particularly advantageous which comprise, in addition to at least one copolymer CP, at least one further thermoplastic material and at least one filler.
  • both the copolymer CP and the further thermoplastic material are each an amorphous thermoplastic.
  • Particularly suitable films have, in addition to an EVA copolymer CP as a chlorosulfonated polyethylene as another thermoplastic material and preferably at least one filler.
  • the weight ratio of other thermoplastics to copolymer CP is a value between 0 to 40, in particular between 0.5 and 20.
  • the proportion of fillers is between 0 and 70 wt .-%, in particular between 5 and 60 wt .-%, based on the weight of the film.
  • a particularly suitable film is Hypalon® / EVA-based films, which are commercially available from Sika für AG under the trade name Sikadur®-Combiflex® tape and strips.
  • the thermoplastic film is preferably elastic and in particular has an elongation at break of between 200 and 800%.
  • the thermoplastic film is treated with an air plasma at atmospheric ambient pressure at least in the area to be bonded.
  • An atmospheric pressure atmospheric plasma is produced by a non-thermal discharge from a working gas, which is air when a high frequency high voltage is applied in a nozzle tube between two electrodes.
  • the working gas is preferably under atmospheric pressure or slightly elevated pressure.
  • the air-plasma treatment used here is carried out at atmospheric ambient pressure. This has the great advantage that no chamber is necessary and that therefore this method can be used outside of industrial applications, and that even larger bodies can be easily treated with the air plasma.
  • the working gas is air.
  • the air is preferably used as compressed air. In this case, a pressure between 2 and 10 bar is preferably used.
  • the plasma exits at the nozzle opening and is directed to the substrate to be treated.
  • Characteristic of such a plasma is that the plasma is energetic but low tempered. In addition, it has a high electron temperature and a low ion temperature.
  • Such plasma sources for generating an air plasma at atmospheric ambient pressure are described in detail in EP 0 761 415 A1 and EP 1 335 641 A1 and are commercially available from Plasmatreat GmbH, Steinhagen, Germany, where they are used for the so-called OpenAir® plasma Technology used. Systems are possible with a plasma nozzle or a plurality of plasma nozzles rotating at very high rotational speeds, which are referred to below as "rotating nozzles".
  • the distance between the substrate surface to be treated and the nozzle is advantageously between 3 mm and 20 mm, in particular between 5 mm and 9 mm. It is clear to the person skilled in the art that a plurality of nozzles can be arranged next to one another or one behind the other. That too treating substrate is treated with a relative speed to the plasma source (without taking into account any rotational speed of a rotating nozzle) between preferably 5 and 50 m / min, in particular between 10 and 25 m / min, preferably between 10 and 15 m / min. In one embodiment, the nozzle is moved and preferably the substrate to be treated is not.
  • Such a treatment form is chosen in particular if the substrate to be treated has a complex shape, in particular if it is a three-dimensional body, or if the treatment in more complex patterns is required.
  • the substrate to be treated is moved relative to a stationary plasma source.
  • This embodiment is preferably used in films, in particular full-surface treatment or on large films, in particular rolls.
  • the treatment width per nozzle is preferably between 20 and 120 mm, in particular between 25 and 100 mm. Wider areas than the treatment width of a nozzle are preferably treated by a plurality of juxtaposed nozzles with air plasma.
  • the substrate can be treated with the air plasma over the whole area or part of the area. For example, only those points can be treated on which later a bonding takes place. Depending on the type of later use, a partial or full-surface bonding is possible.
  • a film it can also be advantageous if both sides are treated with air plasma.
  • Such a double-sided air-plasma treatment can be carried out by simultaneously applying at least one plasma source per side, or first one side, as described, treated with air plasma, then the film is reversed and then the other side also with air Plasma treated. For the air-plasma treatment is no warming up or cooling of the
  • Thermoplastic films treated in this way can be made up after the air-plasma treatment, in particular cut to length or cut into shape, or rolled up.
  • a release film is inserted between the layers.
  • Such release films may consist of a wide variety of materials, such as polyethylene, polypropylene, PET, paper, Teflonized or siliconized plastics or papers. These release films are advantageously added when rolling up. However, the use of such release films is not absolutely necessary.
  • an adhesive is used.
  • either the adhesive is applied to the substrate S2 and then added to the air plasma treated substrate S1 or applied to the air plasma treated substrate S1 and then joined to the substrate S2.
  • one-component moisture-curing adhesives or two-component polyurethane adhesives are suitable as polyurethane adhesives.
  • Such adhesives contain polyisocyanates, especially in the form of isocyanate group-containing prepolymers.
  • Polyurethane adhesives such as those sold by Sika GmbH AG under the product lines Sikaflex® and SikaPower®, are preferred.
  • (Meth) acrylate adhesives are to be understood as meaning two-component adhesives whose first component comprises acrylic acid and / or methacrylic acid and / or their esters, and whose second component comprises a free-radical initiator, in particular a peroxide.
  • Preferred such adhesives are commercially available from Sika Buch AG under the SikaFast® product line.
  • Epoxy adhesives are adhesives which are formulated on the basis of glycidyl ethers, in particular diglycidyl ethers of bisphenol A and / or bisphenol F. Particularly suitable are two-component one-component epoxy resin adhesives, one component of which contains diglycidyl ethers of bisphenol A and / or bisphenol F and the second component of which contains polyamines and / or polymercaptans. Preference is given to two-component epoxy resin adhesives, such as those commercially available from Sika GmbH under the product line Sikadur®.
  • the two-component epoxy resin adhesives Sikadur® -Combiflex®, Sikadur®-31, Sikadur®-31 DW and Sikadur®-33, preferably Sikadur®-Combiflex®, from Sika Sau AG have proven particularly suitable for bonding films.
  • Adhesives based on alkoxysilane-functional prepolymers are understood in particular to be adhesives based on MS polymers or SPUR (silane-terminated polyurethane) prepolymers.
  • reactive hot-melt adhesives can also be used.
  • the adhesive is applied to the substrate S2 and then added to the pretreated with air plasma substrate S1.
  • the adhesive is applied to the surface of the pretreated with air plasma substrate S1 and then be joined to the substrate S2.
  • the former method is particularly preferred when substrate S2 is a large area Body is.
  • the adhesive is applied to the mineral substrate S2, in particular concrete or masonry, and then the air-plasma-treated film S1 is applied, so that the adhesive contacts the film.
  • the substrate S2 is different from the substrate S1, it may be advantageous to pretreat the surface of the substrate S2 prior to bonding.
  • this may be an application of a primer or a coupling agent composition and / or a mechanical cleaning.
  • S2 is a mineral substrate
  • the mechanical cleaning in particular brushing, grinding, sand or shot peening
  • the removal of the so-called cement skin in particular by means of grinding, sandblasting or shot peening, and optionally additionally the use of a primer, is to be recommended as advantageous for ensuring a good and durable bonding.
  • the substrate S2 may, in principle, be all materials suitable for the adhesive used. In addition to the same material as the substrate S1, materials such as glass, ceramics, metals, alloys, paints, plastics, or mineral materials are particularly suitable as substrate S2.
  • the substrate S2 is preferably a metal or an alloy, in particular a steel or an aluminum, or a mineral material, in particular a concrete or a masonry. It may be necessary for the substrate S2 to pretreat the surface of the substrate immediately before bonding. Such a pretreatment can be of a mechanical, chemical or physicochemical nature, as already mentioned above.
  • step (iv) is not to be understood as the beginning of curing, ie the beginning of the cross-linking, but to the effect that the cross-linking has already progressed sufficiently that the adhesive has already built up such a strength that it can transmit forces, and has reached the so-called early strength.
  • the curing is complete when the adhesive has reached its final strength.
  • thermoplastic substrates S1 pretreated with air plasma at ambient atmospheric pressure have an extraordinarily prolonged bondability. This is possible without the need for additional pretreatments, such as the application of primers, primer compositions or corona, plasmas or flame treatments. It has been found that the bondability during weeks,
  • thermoplastics pretreated with air plasma leads to the great technical and economic advantage that these thermoplastics can be treated in a large amount efficiently with the air plasma in a central location, preferably in a film production plant, and subsequently, if appropriate after extensive storage can be transported without haste to the place of bonding, without further pretreatment, such as the application of primers or primer compositions or by surface reactivation by means of energy input or repeated plasma or Coronavor analog, the thermoplastic can be glued easily.
  • the bondability is guaranteed immediately after the air-plasma treatment at atmospheric pressure, but is at least one
  • thermoplastic in particular at least one month, preferably at least one year guaranteed. It is preferred that the air plasma treated thermoplastic is not adhered immediately after treatment, but at least one
  • Week in particular at least one month, preferably at least one year before the adhesion is stored.
  • the elongation of the bondability described here is not limited to the shape of the body, thus an extended bondability was found not only in the thermoplastic films described above but also in other sheet-like bodies and other three-dimensional shapes, such as three-dimensional moldings, from such thermoplastics.
  • particularly preferred body shapes are films, in particular in the form of tapes or strips.
  • a special area where the invention can be used is found as a sealing film in the construction sector, in particular in civil engineering.
  • this is a sealing of working, connecting, dilatation or settlement joints and cracks and the rehabilitation of leaky joints in earth covered components, in groundwater, in tunnels, shafts, dams, sewage systems, water reservoirs and swimming pools.
  • thermoplastic films based on chlorosulfonated polyethylene and an EVA copolymer have been used for this sector Copolymer CP in combination with a two-component epoxy resin adhesive having a first component containing a bisphenol A digylcidyl ether and a second component containing a polyamine, as preferably shown.
  • the slides especially in the form of
  • the film is not glued over the entire surface of the concrete, but only at the edges.
  • the edges of the film are advantageously comprised of adhesive on both sides.
  • the thermoplastic film is pretreated on both sides with air plasma at least in the edge region.
  • the film is advantageously not covered with an adhesive.
  • the advantageous elastic film can thus movements of the dilation joints limiting concrete or masonry parts on which the film is positively connected by means of adhesive, join in and thus accomplish the crack-bridging sealing function.
  • thermoplastic film is glued over a working joint, or a crack, bridging the entire surface with the concrete or masonry.
  • the film is advantageously also covered on the concrete or masonry opposite side with adhesive.
  • the film is thus advantageously surrounded on all sides by adhesive in this embodiment. In order to ensure a good adhesive bond and anchoring of the film in the adhesive, it is therefore advantageous for this embodiment, when the thermoplastic film is pretreated on both sides with air plasma. Examples
  • thermoplastics indicated in Table 1 were melted in a CoIMn rolling mill at a temperature between 150 and 170 ° C, mixed and rolled to a coat of approximately 1.8 mm thickness. Subsequently, the coat was pressed by means of a heated to a temperature between 150 and 170 ° C plate press with a pressure of 80 kN, based on the pressing plate surface, to a film of 1.5 mm thickness. Subsequently, films were cut to dimension 280 * 200 * 1.5 mm. preparation
  • the films produced in this way were treated with an air plasma at atmospheric ambient pressure using a plasma generator Manutec Agrodyn from Plasmatreat GmbH.
  • air at 2.5 bar was used.
  • a rotating nozzle with a diameter of 25 mm was used. The nozzle was moved by means of a robot over the lying film in strips at a distance of 6 mm to the sample surface at a speed of 12 m / min and the films were treated in this way with air plasma.
  • 1.5 mm thick and 20 cm wide Sikadur®-Combiflex® tapes were air-plasma at atmospheric pressure over a Plasmatreat plasma generator with two, juxtaposed, rotating nozzles with a treatment width of 100 mm at a distance of The sample surface of 6-8 mm treated at a speed of 12 m / min.
  • the film was moved under the stationary plasma source.
  • the pressure required for the plasma air was 4 bar. After the air-plasma pretreatment, the film strips were loosely rolled without release films.
  • the films were stored as follows during the time indicated in Table 2: • 23 ° C: The samples were stored in roll form unpacked at ambient temperature in contact with air
  • the measured peel resistance values are shown in Table 2.
  • the steel was pretreated with Sika® ADPrep-5901 (Sika für AG) and flashed for 10 minutes.
  • the Sikadur®-Combiflex® tapes were not subjected to further pretreatment before bonding.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

L'invention concerne un procédé de collage longue durée de thermoplastes. Le traitement par plasma d'air à pression atmosphérique autorise des durées de stockage très longues, pouvant se compter en années, de sorte que les thermoplastes, même dans différentes conditions de stockage, restent collés à long terme, sans que l'adhésion ne diminue de façon notable.
EP06708196A 2005-02-11 2006-02-10 Collage de thermoplastiques traites par plasma d'air Withdrawn EP1851282A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP06708196A EP1851282A1 (fr) 2005-02-11 2006-02-10 Collage de thermoplastiques traites par plasma d'air

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP05101035 2005-02-11
EP06708196A EP1851282A1 (fr) 2005-02-11 2006-02-10 Collage de thermoplastiques traites par plasma d'air
PCT/EP2006/050854 WO2006084901A1 (fr) 2005-02-11 2006-02-10 Collage de thermoplastiques traites par plasma d'air

Publications (1)

Publication Number Publication Date
EP1851282A1 true EP1851282A1 (fr) 2007-11-07

Family

ID=35063380

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06708196A Withdrawn EP1851282A1 (fr) 2005-02-11 2006-02-10 Collage de thermoplastiques traites par plasma d'air

Country Status (7)

Country Link
US (1) US8702892B2 (fr)
EP (1) EP1851282A1 (fr)
JP (1) JP5047811B2 (fr)
CN (1) CN101151340A (fr)
BR (1) BRPI0607182A2 (fr)
MX (1) MX2007009753A (fr)
WO (1) WO2006084901A1 (fr)

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WO2006084901A1 (fr) 2006-08-17
US8702892B2 (en) 2014-04-22
BRPI0607182A2 (pt) 2009-08-11
JP2008530295A (ja) 2008-08-07
MX2007009753A (es) 2007-09-26
CN101151340A (zh) 2008-03-26
US20090226747A1 (en) 2009-09-10
JP5047811B2 (ja) 2012-10-10

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