EP1203121A1 - Wasserlösliches wasserretentionsmittel - Google Patents

Wasserlösliches wasserretentionsmittel

Info

Publication number
EP1203121A1
EP1203121A1 EP00951645A EP00951645A EP1203121A1 EP 1203121 A1 EP1203121 A1 EP 1203121A1 EP 00951645 A EP00951645 A EP 00951645A EP 00951645 A EP00951645 A EP 00951645A EP 1203121 A1 EP1203121 A1 EP 1203121A1
Authority
EP
European Patent Office
Prior art keywords
weight
monomer units
chosen
monomers
water
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
EP00951645A
Other languages
English (en)
French (fr)
Other versions
EP1203121B1 (de
Inventor
François DUPONT
Henri Grondin
Georges Ravet
Jean-Marc Suau
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.)
Coatex SAS
Original Assignee
Coatex SAS
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 Coatex SAS filed Critical Coatex SAS
Publication of EP1203121A1 publication Critical patent/EP1203121A1/de
Application granted granted Critical
Publication of EP1203121B1 publication Critical patent/EP1203121B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • D21H19/00—Coated paper; Coating material
    • D21H19/36—Coatings with pigments
    • D21H19/44—Coatings with pigments characterised by the other ingredients, e.g. the binder or dispersing agent
    • D21H19/56—Macromolecular organic compounds or oligomers thereof obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H19/58—Polymers or oligomers of diolefins, aromatic vinyl monomers or unsaturated acids or derivatives thereof
    • 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
    • Y10T428/3188—Next to cellulosic
    • Y10T428/31895—Paper or wood

Definitions

  • the present invention relates to the technical sector of the manufacture of paper and cardboard, and in particular the sector of water retention agents and rheology modifying agents used for the manufacture of coating sauces.
  • a coating composition is deposited on the surface or surfaces of the support which may contain one or more mineral fillers, one or more binders and various additives.
  • a composition for coating paper generally consists of a filler which may be one or more pigments, one or more polymeric binders and various additives such as in particular a lubricant such as calcium stearate, a wax, or an ester of fatty acid, and optionally anti-foaming agents, and the like, well known to those skilled in the art.
  • a filler which may be one or more pigments, one or more polymeric binders and various additives such as in particular a lubricant such as calcium stearate, a wax, or an ester of fatty acid, and optionally anti-foaming agents, and the like, well known to those skilled in the art.
  • the coating sauce After depositing on the support, the coating sauce has a natural tendency to transfer all or part of the water and the water-soluble parts which it contains into the support. It is necessary to control a too rapid migration which would harm the physical and optical characteristics of the layer.
  • Natural or synthetic agents such as carboxymethylcellulose (CMC), starch, polyvinyl alcohols (PVA) or some latexes or emulsions of highly carboxylated polymers or polycarboxylates, for example of the polyacrylate type.
  • CMC carboxymethylcellulose
  • PVA polyvinyl alcohols
  • Some latexes or emulsions of highly carboxylated polymers or polycarboxylates, for example of the polyacrylate type for example of the polyacrylate type.
  • Such products are described, for example, in patent EP 0509 878.
  • a particular class of retention agents is called swellable alkali polymers, and is described in the aforementioned patent, and as prior art in US patent 4,780,500 which describes water retention agents essentially consisting of acrylic acid monomer and secondarily of itaconic acid monomer, of molecular weight from 100,000 to 800,000.
  • the coating sauce such as pigments such as carbonates, kaolin and the like, or binders such as SBR type latex (“styrene-butadiene-rubber” latex), and other ingredients well known to those skilled in the art;
  • the invention relates in particular to agents aimed at obtaining the above properties.
  • US Patent 4,474,919 also describes non-water-soluble agents of the latex type containing styrene and for example acrylic acid.
  • patent FR 2 675 165 relates to a composition for coating paper with an alkaline pH comprising a mixture of two insoluble latexes with special particle sizes, these particle sizes forming the essential teaching of this patent, and a mineral pigment which is also well specified. , aimed at improving water retention and machinability, with a "suitable" viscosity. Note that particle size is also the main teaching of patent FR 2740456.
  • document JP 58-054096 which describes agents which, according to the proportions of their components, are latexes.
  • Patent JP-56101996 which relates to a mixture of a copolymer of styrene and hemiester of maleic acid and of a terpolymer of styrene, acrylic acid and acrylic ester, also says nothing about the simultaneous control of the viscosity and water retention of the coating sauce. The same analysis applies to patent JP-56101995.
  • patent DD 151 463 describes a viscosity regulating latex which is of the conventional binder type and relates only to the improvement of the viscosity and not of the water retention.
  • patent JP-55018423 describes a copolymer of acrylic acid and other monomers such as styrene in order to produce a simple dispersant which improves only the flow characteristics of the sauce.
  • styrene and (meth) acrylic monomers are naturally monomers generally known in the field of coating coatings for paper, and also in many other fields such as dispersants, agents for painting, etc.
  • the merit of the invention is to have approached the problem from a different angle by looking for a single agent which makes it possible to solve the whole of the above problem and of its technical components also described above.
  • one of the aims of the invention consists in the use, for the manufacture of paper coating coatings, of a copolymer as an agent making it possible to simultaneously regulate the water retention of the coating coat and its Brookfield viscosity. That is to say simultaneously obtaining a high water retention of the coating sauce and a low Brookfield viscosity of said coating sauce or else a high water retention of the coating sauce and a high Brookfield viscosity of said coating coating sauce when the latter is desired by the end user.
  • the Applicant means copolymers which give a homogeneous, clear to cloudy solution in neutral or alkaline medium.
  • the invention proposes the use of an agent on the one hand regulating the water retention of coating sauces for the manufacture of paper and cardboard, and on the other hand making it possible to regulate without additives the viscosity of the said coating sauce, use characterized in that the said agent is water-soluble in neutral or alkaline medium and in that it consists of copolymers composed of:
  • anionic monomer units chosen from acrylic acid or methacrylic acid or their mixtures and optionally chosen from:
  • MTAS - methallylsulfonate
  • sodium allylsulfonate MTAS
  • the invention proposes the use of an agent on the one hand regulating the water retention of coating sauces for the manufacture of paper and cardboard, and on the other hand allowing the viscosity of said coating sauce to be adjusted without additional additives, use characterized in that said agent is water-soluble in neutral or alkaline medium and in that it consists of copolymers composed of:
  • anionic monomer units chosen from acrylic acid or methacrylic acid or their mixtures and optionally chosen from:
  • MTAS methallylsulfonate
  • Fallylsulfonate sodium Fallylsulfonate
  • nonionic monomer units other than the monomers A) chosen more particularly from methyl, ethyl, butyl, 2-ethylhexyl acrylates or methacrylates, ethylene or propylene glycol, oxyethylated acrylates or methacrylates terminated by a chain, linear or branched such as linear or branched alkyl, aryl, alkylaryl, arylalkyl groups having 1 to 50 carbon atoms and in particular di-, tri- and tetrastyrylphenol groups, nonylsphenols, l vinyl acetate, allyl ethers or diisobutylene, vinylpyrrolidone, vinylcaprolactam, acrylonitrile, acrylurethanes, methacrylurethanes, ⁇ - ⁇ 'dimethyl-m- isopropenylbenzyl urethane, allylurethane, acrylamides and acrylamides substituted or not.
  • monomer units having at least two ethylenic unsaturations chosen in a nonlimiting manner from the group consisting of ethylene glycol dimethacrylate, trimethylolpropanetriacrylate, allyl acrylate, maleates d allyl, methylene-bis-acrylamide, methylene-bis-methacrylamide, tetrallyloxyethan
  • the invention therefore also provides a new agent, on the one hand regulating the water retention of coating sauces for the manufacture of paper and cardboard, and on the other hand allowing the viscosity of said coating sauce to be adjusted without additional additives.
  • This new agent is characterized in that it is the copolymer defined above.
  • a high water retention of the coating sauces means, in the context of the invention, a higher water retention than that of the prior art, at equal Brookfield viscosity.
  • a low Brookfield viscosity means, in the context of the invention, a viscosity lower than that of the prior art, with equal water retention.
  • the invention also relates to the coating sauces containing said agent.
  • coating sauces according to the invention are characterized in that they contain, in addition to the usual additives, 0.1% to 2.0% by dry weight and preferably 0.5% to 1.0% by dry weight, by relative to the dry weight of the fillers, of the new agent according to the invention.
  • coating sauces according to the invention are prepared in a conventional manner by a person skilled in the art by mixing, in water, aqueous suspensions of mineral fillers such as for example natural calcium carbonates in particular chalk, cal cite, marble or synthetic calcium carbonates, dolomites, kaolins, talc, titanium dioxide, satin white, mica, calcined clay, aluminum hydroxide, calcium sulphate or their mixtures , water retaining agent, optionally one or more binders of natural or synthetic origin such as, for example, casein, starch, carboxymethylcellulose, alcohols polyvinyl or of latex of the styrene-acrylate or styrene-butadiene type or also of acrylic or vinyl or other latexes.
  • mineral fillers such as for example natural calcium carbonates in particular chalk, cal cite, marble or synthetic calcium carbonates, dolomites, kaolins, talc, titanium dioxide, satin white, mica, calcined clay, aluminum hydroxide, calcium sulphate or
  • the coating sauces according to the invention can also contain, in known manner, usual additives such as rheology modifiers, organic fillers, anti-foaming agents, optical brighteners, biocidal agents, lubricants, alkali hydroxides, insolubilizing agents such as for example ureas and / or melamine-formaldehyde, epichlorohydrin, and others.
  • usual additives such as rheology modifiers, organic fillers, anti-foaming agents, optical brighteners, biocidal agents, lubricants, alkali hydroxides, insolubilizing agents such as for example ureas and / or melamine-formaldehyde, epichlorohydrin, and others.
  • the paper coating sauces containing one or more fillers, the water retentor (s), optionally one or more polymeric binders, pigments, optical brighteners and various other papermaking additives are characterized in that the retention of water and the Brookfield viscosities of the paper coating sauces are simultaneously regulated by the use of the water-retaining agent according to the invention.
  • the water retention of coating sauces is determined by the method described below.
  • the paper coating sauce to be tested is subjected to a pressure of 100 psi (7 bars) in a standardized cylinder, equipped with a filter paper type surface capable of letting water pass.
  • This body (3) consists of:
  • This base (4) supports a metal screen (5) of 60 to 80 mesh on which the paper is placed 90 mm diameter filter (6) (Whatman TM n ° 50) whose equivalent is the DURIEUX BLEU TM n ° 3 type;
  • the assembly is then placed in the stirrup (1) and blocked with the clamping screw (2), then there is a graduated cylinder (12) under the nozzle.
  • a pressure of 7 bars is applied by simultaneously starting a stopwatch.
  • the volume of fluid collected in the test piece (12) is then noted after 20 minutes.
  • the accuracy of the result obtained is ⁇ 0.2 ml.
  • the invention relates to paper and cardboard coated with the coating sauces according to the invention.
  • Other characteristics and advantages of the invention will appear better on reading the description which follows, and with reference to the examples below which cannot have any limiting character of the invention.
  • This example relates to the evaluation of the effectiveness of the agents according to the invention by the determination of the various values of Brookfield viscosity and of water retention of the various 100% calcium carbonate coating sauces which are composed of:
  • CMC carboxymethylcellulose
  • the dry matter content of the coating sauce is of the order of 65.8% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • CMC carboxymethylcellulose
  • CMQ B carboxymethylcellulose
  • the dry matter content of the coating sauce is of the order of 66.2% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • CMQ C carboxymethylcellulose
  • the dry matter content of the coating sauce is of the order of 66.2% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.1% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 65.8% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.1% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is around 66.0% and the pH is about 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.2% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.1% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • This test illustrates the invention and uses an agent according to the invention composed of: - 40.6% by weight of styrene,
  • the dry matter content of the coating sauce is of the order of 65.9% and the pH is of the order of 8.5 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.1% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.1% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 65.8% and the pH is of the order of 8.5 by adjustment with an aqueous solution of sodium hydroxide.
  • Table 1 Also shown in Table 1 are the results of the Brookfield viscosity measurements determined at 10 and 100 revolutions per minute at 25 ° C. using a Brookfield DV-1 viscometer equipped with the appropriate mobile.
  • Reading table 1 makes it possible to highlight on the one hand that, compared to a couple of viscosity and water retention, said here standard, and represented by test n ° 1, the prior art does not allow to fall (tests n ° 2 and n ° 3) or to increase (tests n ° 4 and n ° 5) the viscosity and the water retention only concomitantly.
  • this table 1 makes it possible to demonstrate that, compared with a couple of viscosity and water retention, here called standard, and represented by test n ° 1 of the prior art, the object of the invention represented by tests no. 6, 7, 8, 10, 11 and 12 makes it possible to obtain water retentions greater than or equal to the standard with corresponding viscosities lower than those of the standard.
  • Test No. 9 shows that a water retention value three times higher than that of the standard is obtained for a viscosity value slightly higher than that of the standard of the prior art.
  • This example relates to the evaluation of the effectiveness of the agents according to the invention by the determination of the different values of Brookfield viscosity and of water retention of the different coating sauces (80% calcium carbonate - 20% kaolin) which are composed from:
  • CMQ A carboxymethylcellulose
  • the dry matter content of the coating sauce is of the order of 65.8% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • CMC carboxymethylcellulose
  • the dry matter content of the coating sauce is of the order of 66.2% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • CMC carboxymethylcellulose
  • the dry matter content of the coating sauce is of the order of 66.0% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • CMC carboxymethylcellulose
  • the dry matter content of the coating sauce is of the order of 66.1% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • Test No. 19 This test illustrates the prior art and uses a water retaining agent of the prior art composed, by weight percentage of monomer, of 37% methacrylic acid and 63% ethyl acrylate.
  • the dry matter content of the coating sauce is of the order of 66.0% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.2% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 65.9% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • Test # 22 This test illustrates the invention and uses an agent according to the invention composed of:
  • the dry matter content of the coating sauce is of the order of 66.0% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 65.8% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.0% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.1% and the pH is of the order of 83 by adjustment with an aqueous solution of sodium hydroxide.
  • This test illustrates the invention and uses an agent according to the invention composed of: - 40.6% by weight of styrene,
  • the dry matter content of the coating sauce is around 65.9% and the pH is about 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.0% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 65.6% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • This test illustrates the invention and uses an agent according to the invention composed of: - 30.0% by weight of styrene, - 60.0% by weight of methacrylic acid,
  • the dry matter content of the coating sauce is of the order of 65.8% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • Table 2 Also shown in Table 2 are the results of the Brookfield viscosity measurements determined at 10 and 100 revolutions per minute at 25 ° C. using a Brookfield viscometer of DV-1 type equipped with the appropriate mobile.
  • Reading table 2 makes it possible to highlight on the one hand that, compared to a couple of viscosity and water retention, said here standard, and represented by Fexcellent n ° 15, the prior art does not allow to decrease (tests n ° 16 and n ° 17) or to increase (tests n ° 18 and n ° 19) the viscosity and the water retention only concomitantly.
  • this table 2 makes it possible to highlight that, compared with a couple of viscosity and water retention, said here standard, and represented by Fexcellent n ° 15 of the prior art, the object of l he invention represented by tests no. 21, 22, 23, 24, 25 and 29 makes it possible to obtain water retentions greater than or equal to the standard with corresponding viscosities lower than those of the prior art.
  • Tests 20 and 28 show that a water retention slightly lower than that of the standard is obtained for a viscosity very significantly lower than that of the standard of the prior art.
  • This example relates to the use of various quantities of agents according to the invention by the determination of the different values of Brookfield viscosity and of water retention of a 100% calcium carbonate coating sauce which is composed of:
  • CMQ A carboxymethylcellulose
  • the dry matter content of the coating sauce is of the order of 66.1% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • CMQ A carboxymethylcellulose
  • the dry matter content of the coating sauce is of the order of 66.1% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • the dry matter content of the coating sauce is of the order of 66.2% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • This test illustrates the invention and uses 1.0 part, expressed as dry matter, of the same agent as that of the previous test.
  • the dry matter content of the coating sauce is of the order of 66.0% and the pH is of the order of 8.6 by adjustment with an aqueous solution of sodium hydroxide.
  • Table 3 Also shown in Table 3 are the results of the Brookfield viscosity measurements determined at 10 and 100 revolutions per minute at 25 ° C. using a Brookfield viscometer of DV-1 type equipped with the appropriate mobile.
  • Reading Table 3 illustrates the production of coating sauce according to the invention containing 0.1% to 2.0% by dry weight, relative to the dry weight of the fillers, of the agent according to the invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paper (AREA)
  • Paints Or Removers (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
EP00951645A 1999-07-16 2000-07-10 Wasserlösliches wasserretentionsmittel Expired - Lifetime EP1203121B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9909416A FR2796403B1 (fr) 1999-07-16 1999-07-16 Nouvel agent de retention d'eau hydrosoluble en milieu neutre ou alcalin de type copolymere vinylique-acrylique, applications aux sauces de couchage pour papier et carton, et sauces de couchage et papiers et cartons ainsi obtenus
FR9909416 1999-07-16
PCT/FR2000/001992 WO2001006057A1 (fr) 1999-07-16 2000-07-10 Agent de retention d'eau hydrosoluble

Publications (2)

Publication Number Publication Date
EP1203121A1 true EP1203121A1 (de) 2002-05-08
EP1203121B1 EP1203121B1 (de) 2006-03-01

Family

ID=9548318

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00951645A Expired - Lifetime EP1203121B1 (de) 1999-07-16 2000-07-10 Wasserlösliches wasserretentionsmittel

Country Status (12)

Country Link
US (2) US7138160B1 (de)
EP (1) EP1203121B1 (de)
AT (1) ATE318953T1 (de)
AU (1) AU6451900A (de)
CA (1) CA2379527C (de)
DE (1) DE60026317T2 (de)
DK (1) DK1203121T3 (de)
ES (1) ES2258977T3 (de)
FR (1) FR2796403B1 (de)
MX (1) MXPA02000533A (de)
PT (1) PT1203121E (de)
WO (1) WO2001006057A1 (de)

Cited By (1)

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WO2007069037A1 (fr) 2005-12-16 2007-06-21 Coatex S.A.S. Procede de fabrication de sauces de couchage a la retention d'eau et a la viscosite brookfieldtm ameliorees mettant en oeuvre un polymere peigne avec au moins une fonction greffee oxyde de polyalkylene

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JP4285481B2 (ja) * 2003-07-23 2009-06-24 東亞合成株式会社 水性インク
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FR3088327B1 (fr) * 2018-11-08 2021-11-05 Arkema France Composition copolymerique hydrosoluble
CN114773544B (zh) * 2022-01-19 2023-11-21 浙江莱科新材料科技有限公司 一种含弱阳离子大侧环的聚合物流变保水剂的制备方法及在造纸涂料配方中应用

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WO2007069037A1 (fr) 2005-12-16 2007-06-21 Coatex S.A.S. Procede de fabrication de sauces de couchage a la retention d'eau et a la viscosite brookfieldtm ameliorees mettant en oeuvre un polymere peigne avec au moins une fonction greffee oxyde de polyalkylene

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CA2379527C (fr) 2009-06-02
DK1203121T3 (da) 2006-07-10
US20050288428A1 (en) 2005-12-29
MXPA02000533A (es) 2004-09-10
PT1203121E (pt) 2006-07-31
WO2001006057A1 (fr) 2001-01-25
ATE318953T1 (de) 2006-03-15
ES2258977T3 (es) 2006-09-16
EP1203121B1 (de) 2006-03-01
US7138160B1 (en) 2006-11-21
FR2796403B1 (fr) 2001-09-28
AU6451900A (en) 2001-02-05
CA2379527A1 (fr) 2001-01-25
FR2796403A1 (fr) 2001-01-19
DE60026317D1 (de) 2006-04-27
DE60026317T2 (de) 2006-11-30

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