WO2010040612A1 - Produit de polycondensation phosphaté, son procédé de production et son utilisation - Google Patents

Produit de polycondensation phosphaté, son procédé de production et son utilisation Download PDF

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Publication number
WO2010040612A1
WO2010040612A1 PCT/EP2009/061547 EP2009061547W WO2010040612A1 WO 2010040612 A1 WO2010040612 A1 WO 2010040612A1 EP 2009061547 W EP2009061547 W EP 2009061547W WO 2010040612 A1 WO2010040612 A1 WO 2010040612A1
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WO
WIPO (PCT)
Prior art keywords
represented
structural unit
polycondensation product
different
iii
Prior art date
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PCT/EP2009/061547
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German (de)
English (en)
Inventor
Alexander Kraus
Frank Dierschke
Fabian Becker
Thomas Schuhbeck
Harald Grassl
Tanja DÖRFLER
Karin Groess
Original Assignee
Construction Research & Technology Gmbh
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Filing date
Publication date
Application filed by Construction Research & Technology Gmbh filed Critical Construction Research & Technology Gmbh
Priority to CN200980148980.7A priority Critical patent/CN102239127B/zh
Publication of WO2010040612A1 publication Critical patent/WO2010040612A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/24—Macromolecular compounds
    • C04B24/28—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/30—Condensation polymers of aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/24—Macromolecular compounds
    • C04B24/243—Phosphorus-containing polymers
    • C04B24/246—Phosphorus-containing polymers containing polyether side chains
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/335—Polymers modified by chemical after-treatment with organic compounds containing phosphorus
    • C08G65/3353—Polymers modified by chemical after-treatment with organic compounds containing phosphorus containing oxygen in addition to phosphorus
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
    • C04B2103/30—Water reducers, plasticisers, air-entrainers, flow improvers
    • C04B2103/34—Flow improvers

Definitions

  • the present invention relates to a phosphated polycondensation product, a process for its preparation and the use as additives in a building material mixture.
  • aqueous slurries of powdered inorganic or organic substances such as clays, silicate, chalk, carbon black, rock powder and hydraulic binders to improve their processability, d. H. Kneadability, spreadability, sprayability, pumpability or flowability, additives added in the form of dispersants.
  • Such additives are able to prevent the formation of solid agglomerates, to disperse the particles already present and re-formed by hydration and thus to improve the processability.
  • This effect is also exploited specifically in the production of building material mixtures containing hydraulic binders such as cement, lime, gypsum, hemihydrate or anhydrite.
  • additives are used which are generally referred to as water reducers or flow agents.
  • water reducers or flow agents As such agents in particular polycondensation products and copolymers are used in practice.
  • polycondensation products based on an aromatic or heteroaromatic compound (A) having 5 to 10 C atoms or heteroatoms with at least one oxyethylene or oxypropylene radical and an aldehyde (C) are selected from the group formaldehyde Glyoxylic acid and benzaldehyde or mixtures thereof, which, compared to the conventionally used Poykondensations occur cause improved liquefying action of inorganic binder suspensions and this effect over a longer
  • these may also be phosphated polycondensation products, but the phosphated monomers used are relatively expensive since they must be prepared and purified separately.
  • structural unit (II) and structural unit (III) differ solely in that the OP (OH) 2 group of the structural unit (II) in structural unit (III) is replaced by H and structural unit (III) is not structural unit (I).
  • A is the same or different and is represented by a substituted or unsubstituted aromatic or heteroaromatic compound having 5 to 10 C atoms
  • B is the same or different and represented by N, NH or O.
  • R 1 and R 2 are independently the same or different and represented by a branched or unbranched d- to Cio-alkyl radical, Cs to Cs-cycloalkyl radical, aryl radical, heteroaryl radical or H.
  • X is identical or different and represented by a branched or unbranched C 1 to C 10 -alkyl radical, C 8 to C 8 -cycloalkyl radical, aryl radical, heteroaryl radical or H
  • D is identical or different and represented by a substituted or unsubstituted aromatic or heteroaromatic compound having 5 to 10 C atoms
  • E is the same or different and represented by N, NH or O.
  • R 3 and R 4 are each independently the same or different and represented by a branched or unbranched C 1 to C 10 alkyl radical, C 8 to C 8 cycloalkyl radical, aryl radical, heteroaryl radical or H.
  • the polycondensation product contains a further structural unit (IV), which is represented by the following formula
  • R 5 is identical or different and represented by H, CH 3, COOH or a substituted or unsubstituted aromatic or heteroaromatic compound having 5 to 10 C atoms
  • R 6 is identical or different and represented by H, CH 3, COOH or a substituted or unsubstituted aromatic or heteroaromatic compound having 5 to 10 C atoms.
  • R 5 and R 6 in structural unit (IV) independently of one another are preferably represented by H, COOH and / or methyl.
  • the molar ratio of the structural units (I), (II), (III) and (IV) of the phosphated polycondensation product according to the invention can be varied within wide limits. It has proved to be advantageous that the molar ratio of the structural units [(I) + (II) + (III)]: (IV) 1: 0.8 to 3, preferably 1: 0.9 to 2 and particularly preferably 1: 0.95 to 1.2.
  • the molar ratio of the structural units (I): [(II) + (III)] is normally from 1:10 to 10: 1, preferably from 1: 7 to 5: 1 and more preferably from 1: 5 to 3: 1.
  • the groups A and D in the structural units (I), (II) and (III) of the polycondensation product are usually replaced by phenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4- Methoxyphenyl, naphthyl, 2-hydroxynaphthyl, 4-hydroxynaphthyl, 2-methoxynaphthyl, 4-methoxynaphthyl preferably represents phenyl, where A and D can be selected independently of one another and can each consist of a mixture of said compounds.
  • Groups B and E are preferably independently represented by O.
  • R 1 , R 2 , R 3 and R 4 can be selected independently of one another and are preferably represented by H, methyl, ethyl or phenyl, more preferably by H or methyl and especially preferably by H.
  • a in structural unit (I) is preferably represented by an integer from 5 to 280, in particular from 10 to 160 and more preferably from 12 to 120, and b in structural unit (II) and (III) by an integer from 0 to 10, preferably 1 to 7 and more preferably 1 to 5.
  • the respective radicals, whose length is defined by a or b, may in this case consist of uniform assemblies, but it may also be expedient that it is a mixture of different components.
  • the radicals of the structural units (I) or (II) and (III) may each independently have the same chain length, wherein a and b are each represented by a number. However, it will generally be expedient that they are each mixtures with different chain lengths, so that the radicals of the structural units in the polycondensation product have a different value for a and independently for b.
  • the phosphated polycondensation product according to the invention has a weight-average molecular weight of 4000 g / mol to 150,000 g / mol, preferably 10,000 to 100,000 g / mol and particularly preferably 20,000 to 75,000 g / mol.
  • the phosphated polycondensation product according to the invention is present in aqueous solution containing 2 to 90% by weight of water and 98 to 10% by weight of dissolved water.
  • compound mass preferably 40 to 80% by weight of water and 60 to 20% by weight of dissolved dry matter, more preferably 45 to 75% by weight of water and 55 to 25% by weight of dissolved dry matter.
  • the dry mass then essentially consists of the anhydrous phosphated polycondensation product, but it may also be advantageous to include further components such as defoamers and other auxiliaries.
  • the present invention further provides that it is a sodium, potassium, ammonium and / or calcium salt and, preferably, a sodium and calcium salt, of the phosphated polycondensation product.
  • the present invention also relates to a process for preparing a phosphated polycondensation product, wherein it is to be regarded as essential to the invention that the polycondensation and the phosphating are carried out in a reaction mixture.
  • a reaction mixture By this is meant that the phosphated component formed in the reaction solution is neither purified nor isolated.
  • the phosphating can be carried out before, during or after the polycondensation. It is considered preferable to carry out both the phosphating and the polycondensation in the same reaction vessel.
  • reaction mixture contains at least
  • (lilac) a monomer containing an aromatic or heteroaromatic compound, where (lilac) is partially phosphated during the reaction and the monomer (IIa) and / or in the polycondensation product form the structural unit (IIa),
  • structural unit (IIIa) is other than structural unit (Ia).
  • the monomers (Ia), (IIa), (IIIa) and (IVa) and in the polycondensation product the structural unit (IIa) are preferably represented by the following general formulas
  • A is the same or different and is represented by a substituted or unsubstituted aromatic or heteroaromatic compound having 5 to 10 C atoms
  • B is the same or different and represented by N, NH or O.
  • R 1 and R 2 are independently the same or different and represented by a branched or unbranched d- to Cio-alkyl radical, Cs to Cs-cycloalkyl radical, aryl radical, heteroaryl radical or H.
  • X is identical or different and represented by a branched or unbranched C 1 to C 10 -alkyl radical, C 8 to C 8 -cycloalkyl radical, aryl radical, heteroaryl radical or H
  • D is identical or different and represented by a substituted or unsubstituted aromatic or heteroaromatic compound having 5 to 10 C atoms
  • E is the same or different and represented by N, NH or O.
  • R 3 and R 4 are independently the same or different and represented by a branched or unbranched d- to Cio-alkyl radical, Cs to Cs-cycloalkyl radical, aryl radical, heteroaryl radical or H.
  • R 7 is identical or different and represented by H, CH 3, COOH and / or a substituted or unsubstituted aromatic or heteroaromatic compound having 5 to 10 C atoms
  • R 8 is identical or different and represented by H, CH 3, COOH and / or a substituted or unsubstituted aromatic or heteroaromatic compound having 5 to 10 C atoms.
  • the monomer (IIIa) is first reacted with a phosphating agent and the resulting monomer (IIa) is polycondensed with the monomers (Ia), (IIIa) and (IVa).
  • the monomer (purple) can in this case originate from an incomplete reaction in the phosphating reaction or be added to the reaction mixture in a targeted manner after the phosphating reaction.
  • polyphosphoric acid and / or phosphorus pentoxide have proven suitable as phosphating agents.
  • the polycondensation is carried out in the presence of an acidic catalyst, which is preferably sulfuric acid, methanesulfonic acid, para-toluenesulfonic acid or mixtures thereof.
  • an acidic catalyst which is preferably sulfuric acid, methanesulfonic acid, para-toluenesulfonic acid or mixtures thereof.
  • the polycondensation and the phosphating are advantageously carried out at a temperature between 20 and 140 0 C and a pressure between 1 and 10 bar.
  • a temperature range between 80 and 110 0 C has proven to be expedient.
  • the reaction time can be between 0.1 and 24 hours.
  • the desired degree of crosslinking which can be determined, for example, by measuring the viscosity of the reaction mixture, the reaction mixture is cooled.
  • the reaction mixture is subjected to a thermal aftertreatment at a pH between 8 and 13 and a temperature between 60 and 130 ° C. Due to the thermal aftertreatment, which advantageously takes between 5 minutes and 5 hours, it is possible to significantly lower the aldehyde content, in particular the formaldehyde content in the reaction solution.
  • the present invention provides that to reduce the aldehyde content, the reaction mixture after completion of the condensation and phosphating a vacuum post-treatment at pressures between 10 and 900 mbar subjects.
  • a vacuum post-treatment at pressures between 10 and 900 mbar subjects.
  • other methods known to those skilled in the art for reducing the formaldehyde content can also be used.
  • An example is the addition of small amounts of sodium bisulfite, ethylene urea and / or polyethyleneimine.
  • the resulting phosphated polycondensation products can be used directly as flow aids.
  • Sodium hydroxide, potassium hydroxide, ammonium hydroxide or calcium hydroxide have proved to be particularly useful, it being considered preferable to neutralize the reaction mixture.
  • salts of the phosphated polycondensation but also other alkali and alkaline earth metal salts and salts of organic amines in question.
  • the present invention also provides for the preparation of mixed salts of the phosphated polycondensation products. These can be conveniently prepared by reacting the polycondensation products with at least two basic compounds.
  • salts of the polycondensation products according to the invention can be prepared with which the duration of processability of aqueous suspensions of inorganic binders and especially of concrete can be influenced. While, in the case of the sodium salt, a reduction in processability over time is observed, in the case of the calcium salt of the identical polymer, a complete reversal of this behavior occurs, with initially less water reduction (low slump) occurring, which increases with time. As a result, sodium salts of the phosphated polycondensation products over time reduce the processability of the binder-containing composition, e.g.
  • the corresponding calcium salts over time lead to improved processability.
  • the amount of sodium and calcium salts of the phosphated polycondensation products used it is thus possible to control the development over time of the processability of binders containing masses.
  • the corresponding phosphated polycondensation products which consist of sodium and calcium salts, prepared by reaction with a mixture of basic calcium and sodium compounds, in particular calcium hydroxide and sodium hydroxide.
  • the catalyst used can also be separated in the context of the present invention. Appropriately, this can be done via the salt formed in the neutralization.
  • sulfuric acid is used as a catalyst and the reaction solution is treated with calcium hydroxide, the formed calcium sulfate can be easily separated by filtration, for example.
  • the pH of the reaction solution is 1, 0 to 4.0, in particular 1, 5 to 2.0, the phosphated polycondensation be separated by phase separation of the aqueous salt solution and separated. The phosphated polycondensation product can then be taken up in the desired amount of water.
  • the invention relates to a building material mixture comprising the phosphated polycondensation product according to the invention and a hydraulic binder and / or a latent hydraulic binder.
  • the hydraulic binder is present as cement, lime, gypsum, hemihydrate or anhydrite or as mixtures of these components, preferably as cement.
  • the latent hydraulic binder is normally present as fly ash, trass or blast furnace slag.
  • the phosphated polycondensation product in an amount of 0.01 to 10 wt .-%, in particular 0.05 to 5 wt .-%, is used.
  • the phosphated polycondensation products according to the invention it has proven to be particularly advantageous that they can be prepared by a very cost-effective process, with no further purification of intermediates being necessary.
  • no waste materials must be disposed of.
  • the claimed method also provides further progress in the state of the art from an environmental point of view.
  • the resulting reaction mixture may, if appropriate after treatment with basic compounds, be supplied directly to the intended use as additive for building material mixtures. The underlying task is thus fully solved.
  • a heatable reactor equipped with stirrer is charged with 600 parts of poly (ethylene oxide) monophenyl ether (average molecular weight 2000 g / mol), 58.9 parts of concentrated sulfuric acid, 39 parts of water, 194.4 parts of oligoethylene glycol monophenyl ether phosphoric acid ester (average molecular weight 324 g / mol) and 89.5 parts of 30% formaldehyde solution.
  • the reaction mixture is heated with stirring for 4 hours at 1 10 0 C. Then allowed to cool and neutralized with 50% sodium hydroxide solution to pH 7.
  • a heatable reactor equipped with a stirrer is charged with 16 parts of polyphosphoric acid and heated to 105 0 C. Within 15 minutes, 27.6 parts of phenoxyethanol are metered in with stirring. After 60 minutes, 400 parts of polyisocyanate
  • a heated reactor equipped with a stirrer is charged with 17.8 parts of polyphosphoric phoric acid and heated to 90 0 C. Within 15 minutes, 30.7 parts of phenoxyethanol are added with stirring. After 60 minutes, 445 parts of poly (ethylene oxide) monophenyl ether (average molecular weight 5000 g / mol), 34.8 parts of concentrated methanesulfonic acid, 14.16 parts of paraformaldehyde and 23.2 parts of water are added. The reaction mixture is heated to 105 ° C. with stirring for a further 6 hours. Then allowed to cool and neutralized with 50% sodium hydroxide solution to pH 7.
  • a heatable reactor equipped with a stirrer is charged with 200 parts of polyethylene.
  • step I 600 g cement powder are dry homogenized and placed in a RILEM mixer. Then the amount of water required according to a W / Z value is added and mixed for 30 seconds at 140 rpm (step I). The addition of the sand mixture is then carried out while the mixer is running using a funnel and it is mixed for 30 s at 140 U / min (stage I). After a mixing break of 1.5 minutes, the edges of the mixer are cleaned and an appropriate amount of flow agent from Comparative Example 1 or Invention Examples 2, 3, and 4 is added. It is mixed for a further 60 s at 285 rpm (stage II) and then the flow rate (slump) determined by tapping on a tapping table with Hägermann cone 10 times (DIN EN 1015-3).
  • the dosage of the flow agent is kept constant and the water-cement ratio adjusted so that a slump of about 24 cm is obtained.
  • a mortar based on Karlstadt CEM I 42.5 R and a sand-cement ratio of 2.2 is used.
  • the sand consists of a mixture of 70% by weight of standard sand and 30% by weight of quartz sand.

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  • Chemical & Material Sciences (AREA)
  • Ceramic Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyethers (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

L'invention concerne un produit de polycondensation phosphaté utilisable comme agent auxiliaire de fluidité pour liants hydrauliques, caractérisé en ce qu'il comprend un motif structural (I) présentant un composé aromatique ou hétéroaromatique et une chaîne latérale polyéther, un motif structural phosphaté (II) présentant un composé aromatique ou hétéroaromatique, et un motif structural (III) présentant un composé aromatique ou hétéroaromatique, en ce que le motif structural (II) et le motif structural (III) se différencient exclusivement par le fait que le groupe OP(OH)2 du motif structural (II) dans le motif structural (III) est remplacé par H, et en ce que le motif structural (III) est différent du motif structural (I).
PCT/EP2009/061547 2008-10-06 2009-09-07 Produit de polycondensation phosphaté, son procédé de production et son utilisation WO2010040612A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN200980148980.7A CN102239127B (zh) 2008-10-06 2009-09-07 磷酸化缩聚产物、其制备方法及用途

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08165915.3 2008-10-06
EP08165915 2008-10-06

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WO2011029711A1 (fr) * 2009-09-02 2011-03-17 Basf Construction Polymers Gmbh Formulation et son utilisation
WO2012100417A1 (fr) 2011-01-26 2012-08-02 Construction Research & Technology Gmbh Procédé pour produire un produit de polycondensation
US20120255464A1 (en) * 2011-04-08 2012-10-11 Frank Dierschke Polyelectrolytic flow agent
WO2012136425A1 (fr) 2011-04-08 2012-10-11 Basf Construction Polymers Gmbh Agent d'écoulement polyélectrolytique
WO2012049077A3 (fr) * 2010-10-11 2012-11-22 Basf Construction Polymers Gmbh Dispersant contenant une bouillie de gypse
WO2013152963A1 (fr) * 2012-04-11 2013-10-17 Construction Research & Technology Gmbh Produit de polycondensation à base de composés aromatiques, son procédé de fabrication et son utilisation
EP2687496A1 (fr) 2012-07-20 2014-01-22 BASF Construction Polymers GmbH Synthèse et utilisation de matériau d'ensemencement de plâtre
EP2826827A1 (fr) 2013-07-18 2015-01-21 Basf Se Composition CMP comprenant des particules abrasives à cérium
EP2886580A1 (fr) 2013-12-20 2015-06-24 Construction Research & Technology GmbH Additif pour améliorer la rhéologie des liants inorganiques
EP2899162A1 (fr) 2014-01-22 2015-07-29 Basf Se Synthèse et utilisation d'accélérateurs de durcissement à base de CaSO4
EP2952492A1 (fr) 2014-06-06 2015-12-09 Basf Se Composition à base d'hydrate de silicate de calcium
WO2016146402A1 (fr) 2015-03-13 2016-09-22 Basf Se Procédé de production d'un agent dispersant
WO2017113992A1 (fr) * 2015-12-31 2017-07-06 江苏苏博特新材料股份有限公司 Polycondensat phosphorylé comme agent réducteur d'eau à rendement élevé et son procédé de préparation
WO2017194329A1 (fr) 2016-05-09 2017-11-16 Construction Research & Technology Gmbh Procédé de traitement de scories
WO2018029095A1 (fr) 2016-08-11 2018-02-15 Basf Se Composition de dispersant pour suspensions solides inorganiques
WO2018120385A1 (fr) * 2016-12-30 2018-07-05 江苏苏博特新材料股份有限公司 Polymère séquencé à fonction phosphonato, procédé de préparation associé et application correspondante
US20180346378A1 (en) * 2014-11-20 2018-12-06 Basf Se Rheology modifier for inorganic suspensions
WO2020007664A1 (fr) 2018-07-06 2020-01-09 Basf Se Composition pour masses réfractaires fluides
US10618842B2 (en) 2015-08-21 2020-04-14 Basf Se Accelerator composition
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WO2022214567A1 (fr) 2021-04-09 2022-10-13 Basf Se Utilisation de polyéthers pour dispersions de pigments
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Cited By (43)

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WO2011029711A1 (fr) * 2009-09-02 2011-03-17 Basf Construction Polymers Gmbh Formulation et son utilisation
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