EP1819875A2 - Procede pour produire du papier a grammage eleve - Google Patents

Procede pour produire du papier a grammage eleve

Info

Publication number
EP1819875A2
EP1819875A2 EP05822765A EP05822765A EP1819875A2 EP 1819875 A2 EP1819875 A2 EP 1819875A2 EP 05822765 A EP05822765 A EP 05822765A EP 05822765 A EP05822765 A EP 05822765A EP 1819875 A2 EP1819875 A2 EP 1819875A2
Authority
EP
European Patent Office
Prior art keywords
retention
branched
cationic polyacrylamide
cationic
polyacrylamide
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.)
Granted
Application number
EP05822765A
Other languages
German (de)
English (en)
Other versions
EP1819875B1 (fr
Inventor
Oliver Koch
Rainer Blum
Ron Van Dijk
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1819875A2 publication Critical patent/EP1819875A2/fr
Application granted granted Critical
Publication of EP1819875B1 publication Critical patent/EP1819875B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H23/00—Processes or apparatus for adding material to the pulp or to the paper
    • D21H23/02—Processes or apparatus for adding material to the pulp or to the paper characterised by the manner in which substances are added
    • D21H23/04—Addition to the pulp; After-treatment of added substances in the pulp
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/06—Paper forming aids
    • D21H21/10—Retention agents or drainage improvers
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
    • D21H17/375—Poly(meth)acrylamide
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
    • D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
    • D21H17/45—Nitrogen-containing groups
    • D21H17/455—Nitrogen-containing groups comprising tertiary amine or being at least partially quaternised

Definitions

  • the present invention relates to a process for the production of high basis weight papers, in particular cardboard and paperboard by dewatering a paper stock on a wire in the presence of a combination of at least one amino group-containing polymer and at least one branched cationic polyacrylamide as retention and dewatering agent with sheet formation and Drying of the leaves.
  • Polyethyleneimines and modified polyethyleneimines as retention and drainage agents are known, for example, from German Offenlegungsschrift DE 24 34 816.
  • DE 24 34 816 and the literature cited therein describe the reactions of polyethyleneimine with crosslinkers such as epichlorohydrin, reactions of polyethylenimine or other oligoamines with oligocarboxylic acids to give polyamidoamines, crosslinked products of these polyamidoamines and reactions of the polyamidoamines with ethyleneimine and bifunctional crosslinkers.
  • modified polyethyleneimines are known from WO 00/67884 A1 and WO 97/25367. In the processes described therein, the modified polyethyleneimines are obtained by ultrafiltration.
  • modified polyethylenimines are distinguished, in particular, by a good removal of dewatering and formation, although weaknesses in filler and fiber retention are known in practice.
  • Cationic polyacrylamides are also known in combination with other components as so-called microparticle systems.
  • polymers such as modified polyethylenimines or polyacrylamides are added as flocculants which are further flocculated by subsequent addition of inorganic microparticles such as bentonite or colloidal silica.
  • inorganic microparticles such as bentonite or colloidal silica.
  • the order of addition of the components can also be reversed.
  • EP 0 608 986 A1 discloses a process for producing filler-containing paper in which an anionic component such as bentonite is introduced into the thick material and subsequently a cationic polymer is added to the thin material.
  • an anionic component such as bentonite
  • a cationic polymer is added to the thin material.
  • Another microparticle system is known from EP 0 335 575 A2, wherein a high molecular weight cationic polymer such as polyacrylamide is metered to the fiber suspension before the last shear stage.
  • an inorganic component which may be either bentonite or colloidal silica, is added after the last shear stage.
  • a modified polyethylenimine can also be used.
  • WO 98/01623 A1 discloses a process for the production of paper and paperboard in which two different water-soluble polymers are added prior to a shear stage, wherein the polymers are a polyethyleneimine and a further component which is selected from linear polyacrylamides, cationic starch or polymers containing vinylamine units. After the shear stage, the addition of bentonite, colloidal silica or clay takes place.
  • US Pat. No. 6,103,065 also describes a microparticle system which consists of a cationic polymer, which may also be a polyethyleneimine, with a charge density of> 4 meq / g, a further cationic polymer, such as a lower charge density linear polyacrylamide, and a bentonite.
  • a cationic polymer which may also be a polyethyleneimine, with a charge density of> 4 meq / g
  • a further cationic polymer such as a lower charge density linear polyacrylamide
  • a bentonite such as a lower charge density linear polyacrylamide
  • EP 0 278 336 A2 describes aqueous solutions consisting of a modified polyamidoamine and a cationic, linear polyacrylamide.
  • a cationic group the quaternization product of dimethylaminopropylacrylamide is described. This product is intended to simplify the handling of both types of paper adjuvant and also improve both retention and drainage.
  • the object has been achieved by a method for producing high basis weight papers by dewatering a stock on a wire in the presence of a combination of at least two polymers as a retention and dewatering system with sheet formation and drying of the sheets, wherein the sheet formation is in the absence of finely divided inorganic flocculants and makes it as a retention and dehydrating agent
  • papers having high basis weights are understood as meaning those papers whose basis weight is at least 300 g / m 2 , preferably at least 500 g / m 2 , more preferably at least 750 g / m 2 , very particularly preferably at least 1000 g / m 2 and in particular at least 1500 g / m 2 .
  • surface weights There are no limits to the surface weights. Papers with basis weights of 2000 g / m 2 or even 2500 g / m 2 and more are quite common.
  • Papers with such high basis weights are, for example, packaging papers, cardboard and cardboard.
  • Amino-containing polymers are described in the literature. The individual references are hereby expressly and fully incorporated by reference.
  • polymers containing amino groups are generally water-soluble or dispersible amino group-containing polymers, in particular polyethylene imines or modified polyethyleneimines.
  • polyethylene imines or modified polyethyleneimines for the purposes of the present invention, these may be, in particular, the following amino-containing polymers or modified polyethylenimines:
  • a polyamidoamine which consists of 1 part by mole of a dicarboxylic acid having 4 to 10 carbon atoms and 0.8 to 1.4 parts by mole of a polyalkylenepolyamine having 3 to 10 alkyleneimine units, optionally up to 10% by weight of a Diamines contains, has been obtained and optionally grafted up to 8 Ethyleniminiseren per basic nitrogen group grafted with
  • polyamidoamines grafted with ethyleneimine and crosslinked with bisglycidyl ethers of polyethylene glycols which are described in US 4,144,123.
  • reaction products which are obtainable by reaction of Michael addition products of polyalkylenepolyamines, polyamidoamines, ethyleneimine-grafted polyamidoamines and mixtures of said compounds and monoethylenically unsaturated carboxylic acids, salts, esters, amides or nitriles with at least bifunctional crosslinkers.
  • reaction products are known, for example, from WO 94/14873 A1.
  • the described classes of halogen-free crosslinkers are particularly suitable for their preparation.
  • the average molecular weights M.sub.w of the polyethyleneimines contemplated can be up to 2 million and are preferably in the range from 1,000 to 50,000.
  • the polyethylenimines are partially amidated with monobasic carboxylic acids such that, for example, 0.1 to 90, preferably 1 up to 50% of the amidable nitrogen atoms in the polyethylenimines is present as the amide group.
  • Suitable crosslinkers containing at least two functional double bonds are mentioned above.
  • halogen-free crosslinkers are used.
  • Polyethyleneimines and quaternized polyethyleneimines It come for this z. B. both homopolymers of ethyleneimine and polymers into consideration, for example, ethyleneimine (aziridine) grafted contain.
  • the homopolymers are obtained, for example, by polymerizing ethyleneimine in aqueous solution in the presence of acids, Lewis acids or alkylating agents such as
  • the polyethyleneimines thus obtainable have a broad molecular weight distribution and average molecular weights M w of , for example, 120 to 2-10 6 , preferably 430 to 1 -10 6 .
  • the polyethyleneimines and the quaternized polyethyleneimines may optionally be reacted with a crosslinker containing at least two functional groups (see above).
  • the quaternization of the polyethyleneimines can be carried out, for example, with alkyl halides, such as methyl chloride, ethyl chloride, hexyl chloride, benzyl chloride or lauryl chloride, and with, for example, dimethyl sulfate.
  • Other suitable modified polyethyleneimines are Strecker reaction modified polyethyleneimines, e.g. As the reaction products of Poiyethyleniminen with formaldehyde and sodium cyanide with hydrolysis of the resulting nitriles to the corresponding carboxylic acids. If desired, these products may be reacted with a crosslinker containing at least two functional groups (see above).
  • phosphonomethylated polyethyleneimines and alkoxylated polyethyleneimines which are obtainable, for example, by reacting polyethyleneimine with ethylene oxide and / or propylene oxide and are described in WO 97/25367 A1.
  • the phosphonomethylated and the alkoxylated polyethyleneimides may optionally be reacted with a crosslinker containing at least two functional groups (see above).
  • further polymers containing amino groups for the purposes of the present invention are all polymers mentioned under a) to e), which are subsequently subjected to ultrafiltration as described in WO 00/67884 A1 and WO97 / 23567 A1.
  • the polymers containing amino groups or modified polyethyleneimines are preferably selected from polyalkyleneimines, polyalkylenepolyamines, polyamidoamines, polyalkyleneglycol polyamines, polyamidoamines grafted with ethyleneimine and subsequently reacted with at least bifunctional crosslinking agents, and mixtures and copolymers thereof.
  • Preference is given to polyalkyleneimines, in particular polyethyleneimines, and the derivatives thereof.
  • Particularly preferred are polyamidoamines which have been grafted with ethyleneimine and subsequently reacted with at least bifunctional crosslinkers.
  • amino-containing polymers are selected from the polymers described in DE 24 34 816 and the ultrafiltered amino-containing polymers described in WO 00/67884 A1. These publications are hereby incorporated by reference.
  • polymers are used as component (a) by condensation of C 2 -C 12 dicarboxylic acids, in particular adipic acid, with poly (alkylenediamines), in particular diethylenetriamine, triethylenetetramine and tetraethylenepentamine, or mono-, bis -, tris or tetra (aminopropyl) ethylenediamine or mixtures thereof, grafting of the polyamidoamines obtained in the condensation with ethyleneimine and subsequent crosslinking are available. It is preferred to graft with as much ethyleneimine that the polyamidoamine per grafted nitrogen basic group contains 2 to 50, preferably 5 to 10 ethyleneimine units grafted on.
  • the grafted polyamidoamine is crosslinked by reaction with halogen-free, at least bifunctional crosslinkers, preferably bisglycidyl ethers of a polyalkylene glycol.
  • Particularly preferred are bis-glycidyl ethers of polyethylene glycols having molecular weights between 400 and 5,000, in particular 500 to 3,000, such as. B. about 600 or about 2,000.
  • Component (b) of the retention and dewatering agent are those branched cationic polyacrylamides which, apart from acrylamide and at least one permanently cationic comonomer, contain a third difunctional or trifunctional unsaturated component which leads to the branching of the polymer chains.
  • Such branched cationic polymers are described for example in US 20030150575.
  • the branched (co) polyacrylamide is preferably a cationic copolymer of acrylamide and a non-saturated cationic ethylene monomer selected from dimethylaminoethyl acrylate (ADAME), dimethylaminoethylacrylamide, dimethylaminoethyl methacrylate (MADAME) which is quaternized by various acids and quaternizing agents or salt-forming such as benzyl chloride, methyl chloride, alkyl or aryl chloride, dimethyl sulfate, furthermore dimethyldiallylammonium chloride (DADMAC), acrylamidopropyltrimethylammonium chloride (APTAC) and methacrylamidopropyltrimethylammonium chloride (MAPTAC).
  • ADAME dimethylaminoethyl acrylate
  • MADAME dimethylaminoethyl methacrylate
  • DADMAC dimethyldiallylammonium chloride
  • ATAC
  • Preferred cationic monomers are dimethylaminoethyl acrylate methochloride and dimethylaminoethyl acrylamide methochloride, which are obtained by alkylation of dimethylaminoethyl acrylate or dimethylaminoethylacrylamide with methyl chloride.
  • This copolymer is branched, as known to those skilled in the art, through a branching agent consisting of a compound having at least two reactive moieties selected from the group comprising double, aldehyde or epoxy bonds. These compounds are known and are described, for example, in the document EP 0 374 458 A1.
  • a branched polymer is a polymer having branches, groups or branches in its entirety, which are not arranged in three directions as a whole in one plane and in contrast to a cross-linked polymer; such high molecular weight branched polymers are well known as flocculants in papermaking.
  • These branched polyacrylamides differ from the crosslinked polyacrylamides in the fact that in these latter groupings are arranged three-dimensionally to result in practically insoluble products of infinite molecular weight.
  • the branching may preferably be accomplished during (or optionally after) the polymerization, for example by reaction of two soluble polymers having counterions, or by reaction via formaldehyde or a polyvalent metal compound. Often the branching takes place during polymerization by the addition of a branching agent, this solution being preferred in practice.
  • the branched polymerization processes are well known.
  • branching agents which can be incorporated include ionic branching agents such as polyvalent metal salts, formaldehyde, glyoxal, or also, preferably, covalent crosslinking agents which copolymerize with the monomers, preferably diethylene-unsaturated monomers (such as the family of diacrylate esters such as the diacrylates of Polyethylene glycols PEG), or polyethylene-unsaturated monomers of the type conventionally used for the crosslinking of water-soluble polymers. in particular methylenebisacrylamide (MBA) or any of the other known acrylic branching agents.
  • ionic branching agents such as polyvalent metal salts, formaldehyde, glyoxal, or also, preferably, covalent crosslinking agents which copolymerize with the monomers, preferably diethylene-unsaturated monomers (such as the family of diacrylate esters such as the diacrylates of Polyethylene glycols PEG), or polyethylene-unsaturated monomers of the type conventionally used for the
  • crosslinking agents are often identical to the crosslinking agents, but if a branched and uncrosslinked polymer is to be obtained, crosslinking can be achieved by optimizing the polymerization conditions such as concentration in polymerization, type and amount of the transfer agent, temperature, type and amount of Initiators and the like, can be prevented.
  • the branching agent is methylenebisacrylamide (MBA), which is added at five to two hundred (5 to 200), preferably 5 to 50, moles per million moles of the monomer.
  • MBA methylenebisacrylamide
  • In erfindungsgze present method are preferably those branched cationic polyacrylamides used which have a Rl of> 20%, preferably> 40%.
  • branched cationic polyacrylamides which consist of a mixture of branched and linear polyacrylamides, as described in the prior art, by the process according to the invention.
  • a mixture usually consists of a branched cationic polyacrylamide as described above and a linear polyacrylamide in a ratio of 99: 1 to 1: 2, preferably in a ratio of 90: 1 to 2: 1 and more preferably in one Ratio of 90: 1 to 3: 1.
  • mixtures are preferably used in which at least 10 mol% of a cationic monomer, as listed above for component (b), preferably at least 20 mol% of a cationic monomer.
  • components (a) and (b) are preferably used as water-in-oil emulsions.
  • component (a) is preferably fixed in an amount of 100 g to 3 kg, ie pure active substance without solvent of the emulsion, based on one ton of dry paper, preferably in the range of 150 g 2.0 kg, based on one ton of dry paper and more preferably in the range of 200 g to 1, 2 kg based on a ton of dry paper used.
  • the component (b) is fixed in a range of from 50 g to 800 g, i. pure active substance without solvent of the emulsion, based on one ton of dry paper, preferably in the range from 65 g to 600 g, based on one ton of dry paper and more preferably in the range of 80 g to 400 g, based on one ton of dry paper.
  • components (a) and (b) are preferably used in a ratio of at least 2: 1, preferably at least 3: 1 and more preferably at least 4: 1.
  • the retention and dehydrating agent system can be supplied to the paper stock-as a rule, the dosing of the retention and dewatering agent takes place in the thin material-for example in the form of a mixture of components (a) and (b).
  • both components can also be introduced into the thin material separately from one another before or after a shear stage.
  • At least one compound of component (a) is metered in, followed by at least one compound of component (b).
  • the compound of component (a) can be supplied to the stock, for example, before a shear stage and the compound of component (b) after the last shear stage before the headbox.
  • both compounds can be dosed before the last shear stage before the headbox or after the last stage before the headbox for pulp.
  • the present invention is also the use of the combination of
  • papers of high basis weight can be produced by the process according to the invention, as described above.
  • wood pulp, thermo-mechanical pulp (TMP), chemo-thermo-mechanical pulp (CTMP), pressure pulp (PGW) and sulfite and sulfate pulp can be used.
  • TMP thermo-mechanical pulp
  • CMP chemo-thermo-mechanical pulp
  • PGW pressure pulp
  • sulfite and sulfate pulp can be used.
  • Wood pulp and pulp are further processed into paper, especially in the so-called integrated Textilfabrikerün more or less moist form directly without prior thickening or drying. Due to the impurities not completely removed therefrom, these fiber materials still contain substances that greatly disrupt the usual papermaking process. If such pulps are used, it is advisable to work in the presence of a fixative.
  • 100% recovered paper is used for the production of high basis weight papers
  • both unfilled and filler-containing papers can be produced.
  • the filler content in the paper may be up to a maximum of 40% by weight and is preferably in the range of 5 to 30% by weight.
  • Suitable fillers are, for example, clay, kaolin, native and precipitated circles, titanium dioxide, talc, calcium sulfate, barium sulfate, aluminum oxide, satin white or mixtures of the stated fillers.
  • the papermaking can be carried out in the presence of the usual process chemicals in the usual amounts, e.g. bulk sizing agents, such as in particular alkyldiketene dispersions, rosin size, alkenyl succinimide dispersions or sizing polymer dispersions, solidifying agents such as epichlorohydrin cross-linked polyamidoamines, polyvinylamines of average molecular weight or strength, fixatives, biocides, dyes and fillers.
  • the dosage of the usual process auxiliaries is preferably carried out in the thin material.
  • the process according to the invention gives papers of high basis weights with improved retention, especially in the case of fillers, and dewatering, as compared with the products prepared by known processes. Furthermore, the process according to the invention is simpler to carry out in comparison to the microparticle processes.
  • the percentages for the starting materials always mean percent by weight.
  • PEI Polyethyleneimine
  • HM Polymin® ® from BASF Aktiengesellschaft Polymer A: linear cationic polyacrylamide, medium molecular weight with
  • Polymer B linear cationic polyacrylamide, high molecular weight with
  • Polymer C linear cationic polyacrylamide, high molecular weight with 50 mol% cationic content
  • Dewatering time for high basis weight papers is determined under vacuum according to the following method:
  • the fiber mat is dried at 105 0 C to constant mass and weighed again (weight G2).

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  • Paper (AREA)

Abstract

L'invention concerne des procédés pour produire du papier à grammage élevé comprenant le dessèchement d'un matériau en papier sur une toile, en présence d'une combinaison d'au moins deux polymères utilisée en tant que système d'agents de dessèchement et de rétention, lors de la formation de feuilles et du séchage desdites feuilles, la formation de feuilles étant réalisée en l'absence d'agents de floculation inorganiques, en fines particules. Les agents de dessèchement et de rétention correspondent (a) à au moins un polymère contenant un groupe amino et (b) au moins un polyacrylamide cationique ramifié.
EP05822765.3A 2004-12-03 2005-12-01 Procede pour produire du papier a grammage eleve Expired - Lifetime EP1819875B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004058587A DE102004058587A1 (de) 2004-12-03 2004-12-03 Verfahren zur Herstellung von Papieren mit hohen Flächengewichten
PCT/EP2005/012796 WO2006058732A2 (fr) 2004-12-03 2005-12-01 Procede pour produire du papier a grammage eleve

Publications (2)

Publication Number Publication Date
EP1819875A2 true EP1819875A2 (fr) 2007-08-22
EP1819875B1 EP1819875B1 (fr) 2015-03-18

Family

ID=36500066

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05822765.3A Expired - Lifetime EP1819875B1 (fr) 2004-12-03 2005-12-01 Procede pour produire du papier a grammage eleve

Country Status (7)

Country Link
US (1) US8152962B2 (fr)
EP (1) EP1819875B1 (fr)
CN (1) CN101068985B (fr)
CA (1) CA2591299C (fr)
DE (1) DE102004058587A1 (fr)
ES (1) ES2539631T3 (fr)
WO (1) WO2006058732A2 (fr)

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WO2006058732A3 (fr) 2006-10-19
EP1819875B1 (fr) 2015-03-18
WO2006058732A2 (fr) 2006-06-08
US20100147475A1 (en) 2010-06-17
CA2591299A1 (fr) 2006-06-08
ES2539631T3 (es) 2015-07-02
CN101068985B (zh) 2012-10-10
CA2591299C (fr) 2014-10-07
CN101068985A (zh) 2007-11-07
DE102004058587A1 (de) 2006-06-14
US8152962B2 (en) 2012-04-10

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