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EP3068745A1 - Mittel zur bewahrung der fliessfähigkeit für hydraulische zusammensetzungen, kompatibel mit einem wasserreduzierenden kammpolymerartigen mittel - Google Patents

Mittel zur bewahrung der fliessfähigkeit für hydraulische zusammensetzungen, kompatibel mit einem wasserreduzierenden kammpolymerartigen mittel

Info

Publication number
EP3068745A1
EP3068745A1 EP14809482.4A EP14809482A EP3068745A1 EP 3068745 A1 EP3068745 A1 EP 3068745A1 EP 14809482 A EP14809482 A EP 14809482A EP 3068745 A1 EP3068745 A1 EP 3068745A1
Authority
EP
European Patent Office
Prior art keywords
agent
units
water
copolymer
group
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Withdrawn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
EP14809482.4A
Other languages
English (en)
French (fr)
Inventor
David Platel
Yves MATTER
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 EP3068745A1 publication Critical patent/EP3068745A1/de
Withdrawn legal-status Critical Current

Links

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
    • C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/2688—Copolymers containing at least three different monomers
    • C04B24/2694—Copolymers containing at least three different monomers containing polyether side chains
    • 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
    • C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/2641—Polyacrylates; Polymethacrylates
    • C04B24/2647—Polyacrylates; Polymethacrylates containing polyether side chains
    • 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
    • C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/2664—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of ethylenically unsaturated dicarboxylic acid polymers, e.g. maleic anhydride copolymers
    • C04B24/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of ethylenically unsaturated dicarboxylic acid polymers, e.g. maleic anhydride copolymers containing polyether side chains
    • 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
    • C04B28/00—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements
    • C04B28/02—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements containing hydraulic cements other than calcium sulfates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • C08F220/68—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • 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
    • C04B2103/0045—Polymers chosen for their physico-chemical characteristics
    • C04B2103/0062—Cross-linked polymers
    • 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
    • C04B2103/308—Slump-loss preventing agents

Definitions

  • dispersing agents for hydraulic compositions. These agents differ in their chemical composition and the properties they induce in the compositions containing them.
  • fluidity retentive agents are also proposed to ensure maneuverability for a prolonged time.
  • WO 2007/047407 describes a method for increasing the workability of combining three additives: an initial fluidity increasing agent, a fluidity retaining agent and an agent that controls the response of the agent increasing the initial fluidity when the first two agents are added to said composition.
  • An object of the present invention is to provide a copolymer agent for hydraulic compositions whose essential property fluidity retention.
  • Another object of the present invention is to provide a copolymer which does not provide initial fluidity when it is within a hydraulic composition.
  • a "water reducing agent” or a “plasticizer” is an agent which, in accordance with the ADJUVANT standard NF EN 934-2, allows a water reduction for the adjoining concrete> 5% compared to the control concrete.
  • a "high water reducer” or “superplasticizer” is an adjuvant that allows water reduction for adjuvanted concrete> 12% over control concrete.
  • the fluidity retentive agent according to the invention does not meet these characteristics.
  • the fluid retention agent according to the invention is completely compatible with a water reducing agent, plasticizer or superplasticizer. This makes it possible to formulate the hydraulic compositions adapted to each structure, without having to adjust the amounts of one or the other of the additives to obtain a desired profile of initial fluidity and maintenance of the maneuverability over time.
  • At least one nonionic crosslinking monomer comprising at least two radicals selected from the group consisting of acrylic esters, methacrylic esters, maleic esters, itaconic esters, crotonic esters and a mixture of these esters.
  • the anionic monomers according to a) can be used in a mass proportion varying between 0.5 and 40% by weight according to one aspect of the invention, between 5 and 30% by weight according to another aspect of the invention and between 7 and 25% by weight according to still another aspect of the invention, the percentage being based on the total weight of all the monomers which constitute the retention agent according to the invention.
  • n and p are 0.
  • the flow-retaining agent according to the invention may be in the form of salts, stoichiometric or otherwise, mixed or not and consisting of alkali metals, alkaline earth metals, amines or quaternary ammoniums. According to one embodiment, the flow-retaining agent according to the invention is in acid form.
  • the additive according to the invention is water-soluble or water-dispersible. Handling agent
  • a water-reducing agent of the dispersant copolymer type obtained by polymerization of: a) at least one anionic monomer having a saturable polymerizable function and a carboxyl group and
  • [(EO) i - (OP) j - (OB) k ] represents a polyalkoxylated chain consisting of alkoxylated units, divided into blocks, alternating or random, chosen from ethoxylated units EO, propoxylated units OP and butoxylated units OB ,
  • the water-reducing agent is a copolymer obtained by direct esterification (or grafting or polyesterification) of a polymer (homopolymer or copolymer) containing carboxylic or anhydride functions.
  • a copolymer obtained by direct esterification or grafting or polyesterification
  • a polymer homopolymer or copolymer containing carboxylic or anhydride functions.
  • Coatex WO 2007/132322 which discloses such a method.
  • the handling agent for hydraulic compositions consists of a compatible mixture of the two following additives:
  • a water-reducing agent of dispersing copolymer type obtained by functionalization of a homopolymer and / or a copolymer of (meth) acrylic acid by esterification with at least one compound comprising a polyalkoxylated chain consisting of alkoxylated units, divided into blocks, alternating or random, selected from ethoxylated units EO, propoxylated units OP and butoxylated units OB.
  • said water-reducing agent is a copolymer obtained by polymerization of macromonomers b) of formula (II) in which the radical R ⁇ j is chosen from the group consisting of acrylic esters, methacrylic esters, maleic esters, itaconic esters, crotonic esters and a mixture of these esters.
  • said water-reducing agent is a copolymer obtained by polymerization of macromonomers b) of formula (II) in which the radical Rd is chosen from the group consisting of acrylic esters, methacrylic esters and a mixture of these esters.
  • said water-reducing agent is a copolymer obtained by copolymerization of monomers a) selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, itaconic acid, and a mixture of these monomers.
  • i represents an integer ranging between 1 and 250, for example between 10 and 200 or for example between 40 and 150 and
  • alkylene glycol polymers include: polyalkylene glycols having an average molecular weight of 1,000, 4,000, 6,000 and 10,000 g / mol; polyethylenes polypropylenes glycols having a percentage of ethylene oxides of between 20 and 80% by weight and a percentage of propylene oxides of between 20 and 80% by weight.
  • the fluidity retentive agent makes it possible to extend the handling time of the concrete, in particular when it is added to the composition in combination with the water reducing agent described above. It is a combination of additives having advantageous properties for hydraulic compositions, for example concretes, mortars, glues, coatings or grouts.
  • said hydraulic composition comprises, expressed as a percentage by dry weight of said fluid retention agent relative to the dry weight of cement, from 0.1% to 3% of said fluid retentive agent.
  • said hydraulic composition comprises, expressed as a percentage by dry weight of said workability agent relative to the dry weight of cement, from 0.05% to 5% of said workability agent.
  • Hydraulic compositions for example concrete and mortar compositions, for which the flow-retaining agent according to the invention may be useful may comprise, as hydraulic binder, different types of cements such as CEM I, CEM II, CEM cements. III, EMC V as described in the standard EN 197-1. Of these, CEM I cements do not have additions. It is nevertheless possible to add to these cements slags, fly ash, calcareous fillers, siliceous fillers.
  • the concrete compositions may be concrete of classes of different strengths such as C20 / 25 to C100 / 115.
  • the hydraulic composition according to the invention comprises, relative to the total weight of the composition:
  • the hydraulic composition according to the invention comprises, relative to the total weight of the composition:
  • hydraulic binder comprising a cement
  • fine or ultra-fine fillers for example calcium carbonate or silica, anti-foam agent,
  • said fluid retentive agent and said water reducing agent are introduced separately into said hydraulic composition.
  • the present invention also relates to a copolymer as fluidity retentive agent for hydraulic compositions, said copolymer being obtained by polymerization of: a) at least one anionic monomer comprising a polymerizable unsaturated functional group and a carboxylic group,
  • R f ' represents hydrogen or an alkyl group having from 1 to 4 carbon atoms and
  • [(OE); - (OP) j - (OB) k ] represents a polyalkoxylated chain consisting of alkoxylated units, divided into alternating or random blocks, chosen from ethoxylated units EO, propoxylated units OP and butoxylated units OB,
  • R d ' represents hydrogen or an alkyl group having from 1 to 4 carbon atoms
  • said copolymer having a molecular weight of between 20,000 g / mol and 400,000 g / mol.
  • the molecular weight of the copolymers according to the invention is determined by Steric Exclusion Chromato graphy (CES).
  • the liquid chromatography apparatus contains an isocratic pump (WATERS TM 515) with a flow rate of 0.8 ml / min.
  • the chromatography apparatus also comprises an oven which itself comprises in series the following column system: a precolumn GUARD COLUMN type ULTRAHYDROGEL WATERS TM 6 cm long and 40 mm internal diameter, a linear column type ULTRAHYDROGEL WATERS TM 30 cm long and 7.8 mm inside diameter and two columns ULTRAHYDROGEL 120 ANGSTROM WATERS TM 30 cm long and 7.8 mm inside diameter.
  • the cone is placed on a plate moistened with a sponge.
  • a concrete according to EN 480-1 is prepared by mixing with stirring, standardized sand (0/4), cement (CEM I 52.5N Holcim), gravel 4/11 and 11/22, water and possibly an anti-foaming agent.
  • a water-reducing agent and / or a fluid-retaining agent according to the invention is optionally added.
  • the proportions of each constituent are given in Table 1 below.
  • the dispersant copolymer has a molecular weight of between 110,000 and 150,000 g / mol and is partially neutralized with NaOH (pH 3-4.5).
  • the fluidity retaining agent exemplified in the tests 1-3 to 1-5 below is a copolymer according to the invention, prepared according to the method below.
  • DMDO 1,8-dimercapto-3,6-dioxaoctane
  • a solution consisting of 0.9 g of ammonium persulfate and 4.4 g of deionized water is prepared.
  • the reagents contained in the 3 containers are introduced into the reactor heated to 70 ° C. and with stirring.
  • the mixture is then cooked for 2 hours at 67 ° C.
  • the fluidity retaining agent exemplified is therefore composed of, based on the total weight of the copolymer:
  • the resistance at the young ages of the formulation according to test 1-5 is similar to that of the control composition (test 1-2) comprising as sole additive a water-reducing agent. It is thus demonstrated that the flow-retaining agent according to the invention is not a set-retarding agent. It is furthermore confirmed that, in accordance with the standard ADJUVANT NF EN 934-2 (Table 3.1), the resistance values of the adjuvanted concretes (tests 1-2 and 1-5) at 1 day are greater than 140% of the value. resistance of control concrete without adjuvant (test 1-1).
  • a concrete according to EN 480-1 is prepared by mixing with stirring, standardized sand (0/4), cement (CEM I 52.5N Holcim), gravel 4/11 and 11/22, water and possibly an anti-foaming agent.
  • a water-reducing agent and a flow-retaining agent according to the invention.
  • the proportions of each constituent are given in Table 2 below. More specifically, the water reducing agent exemplified in the tests below is a dispersant copolymer identical to that of Example 1.
  • Tests 2-1 to 2-4 illustrate various fluidity-retaining agents according to the invention or to the invention. They are prepared according to a procedure similar to that of Example 1 above.
  • the fluidity retaining agent exemplified in test 2-1 consists of, based on the total weight of the copolymer:
  • the fluidity retaining agent exemplified in test 2-2 consists of, based on the total weight of the copolymer: 8% by weight of acrylic acid monomers,
  • the fluidity retaining agent exemplified in test 2-3 consists of, based on the total weight of the copolymer:
  • the fluidity retaining agent exemplified in test 2-4 consists of, based on the total weight of the copolymer:
  • na the measured maneuverability at a previous time is ⁇ 100 ⁇ 10 mm or the measurement is impossible
  • test 2-1 and 2-2 show, moreover, that the combination of the said fluid retention agents according to the invention and a high water reducing agent at the same time allows a good initial fluidity as well as a maintenance maneuverability over time.
  • a concrete according to EN 480-1 is prepared by mixing with stirring, standardized sand (0/4), cement (CEM I 52.5N Holcim), gravel 4/11 and 11/22, water and a water-reducing agent and a flow-retaining agent according to the invention are added at two different doses.
  • the proportions of each constituent are given in Table 3 below.
  • Tests 3-1 and 3-2 illustrate a fluid retention agent according to the invention. They are prepared according to a procedure similar to that of Example 1 above.
  • Tests 3-3 and 3-4 illustrate a fluidity retaining agent according to the invention. They are prepared according to a procedure similar to that of Example 1 above.
  • This agent consists of, based on the total weight of the copolymer: 8.1% by weight of acrylic acid monomers,

Landscapes

  • Chemical & Material Sciences (AREA)
  • Ceramic Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
EP14809482.4A 2013-11-15 2014-11-12 Mittel zur bewahrung der fliessfähigkeit für hydraulische zusammensetzungen, kompatibel mit einem wasserreduzierenden kammpolymerartigen mittel Withdrawn EP3068745A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1361234A FR3013350B1 (fr) 2013-11-15 2013-11-15 Agent retenteur de fluidite pour composition hydraulique compatible avec agent reducteur d'eau de type polymere peigne
PCT/FR2014/052871 WO2015071584A1 (fr) 2013-11-15 2014-11-12 Agent retenteur de fluidite pour compositions hydrauliques compatible avec agent reducteur d'eau de type polymere peigne

Publications (1)

Publication Number Publication Date
EP3068745A1 true EP3068745A1 (de) 2016-09-21

Family

ID=50424395

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14809482.4A Withdrawn EP3068745A1 (de) 2013-11-15 2014-11-12 Mittel zur bewahrung der fliessfähigkeit für hydraulische zusammensetzungen, kompatibel mit einem wasserreduzierenden kammpolymerartigen mittel

Country Status (7)

Country Link
US (1) US20160289120A1 (de)
EP (1) EP3068745A1 (de)
CN (1) CN105722804A (de)
CA (1) CA2929307A1 (de)
FR (1) FR3013350B1 (de)
MX (1) MX2016006306A (de)
WO (1) WO2015071584A1 (de)

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Publication number Priority date Publication date Assignee Title
WO2018177908A1 (de) * 2017-03-30 2018-10-04 Basf Se Zwei-komponenten stabilisator für anorganische suspensionen
FR3069548B1 (fr) * 2017-07-28 2019-08-02 Coatex Composition polymerique aqueuse et copolymere
FR3069546B1 (fr) 2017-07-28 2020-09-25 Coatex Sas Composition polymerique aqueuse et copolymere
CN112920337B (zh) * 2021-01-29 2022-11-18 湖北工业大学 一种稳定泵送型保坍剂及其制备方法
CN113174019B (zh) * 2021-05-21 2022-12-16 山西佳维新材料股份有限公司 一种水性环氧酯改性的聚羧酸减水剂及其制备方法和应用
CN116040975B (zh) * 2023-01-16 2024-08-20 杭州构建新型材料有限公司 一种抗泥型聚羧酸减水剂及其制备方法

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JP2774445B2 (ja) * 1993-12-14 1998-07-09 花王株式会社 コンクリート混和剤
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JP5215663B2 (ja) 2004-09-09 2013-06-19 株式会社日本触媒 共重合体および分散剤
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Also Published As

Publication number Publication date
CA2929307A1 (fr) 2015-05-21
FR3013350B1 (fr) 2016-09-02
WO2015071584A1 (fr) 2015-05-21
US20160289120A1 (en) 2016-10-06
CN105722804A (zh) 2016-06-29
FR3013350A1 (fr) 2015-05-22
MX2016006306A (es) 2016-09-06

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