US20110207856A1 - Use as an agent improving the workability of an aqueous formulation with a hydraulic binder base, of a (meth)acrylic comb-branched copolymer and an associative acrylic thickener - Google Patents

Use as an agent improving the workability of an aqueous formulation with a hydraulic binder base, of a (meth)acrylic comb-branched copolymer and an associative acrylic thickener Download PDF

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US20110207856A1
US20110207856A1 US13/126,021 US200913126021A US2011207856A1 US 20110207856 A1 US20110207856 A1 US 20110207856A1 US 200913126021 A US200913126021 A US 200913126021A US 2011207856 A1 US2011207856 A1 US 2011207856A1
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comb
acrylic
aqueous formulation
meth
branched copolymer
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David Platel
Jean Moro
Olivier Guerret
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Coatex SAS
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Coatex SAS
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    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • 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
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C04B16/00—Use of organic materials as fillers, e.g. pigments, for mortars, concrete or artificial stone; Treatment of organic materials specially adapted to enhance their filling properties in mortars, concrete or artificial stone
    • C04B16/04—Macromolecular compounds
    • 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
    • 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
    • C04B40/00—Processes, in general, for influencing or modifying the properties of mortars, concrete or artificial stone compositions, e.g. their setting or hardening ability
    • C04B40/0028—Aspects relating to the mixing step of the mortar preparation
    • C04B40/0039—Premixtures of ingredients
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • 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
    • 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
    • C04B2103/0049—Water-swellable polymers
    • C04B2103/005—Alkali-swellable 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
    • C04B2103/32—Superplasticisers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group

Definitions

  • the present invention pertains to the field of admixtures which are used in aqueous formulations with hydraulic binder bases, such as cements, concretes, or mortars, in order to improve their workability.
  • hydraulic binder bases such as cements, concretes, or mortars.
  • the highest-performance among these workability agents today are comb-branched polymers, which have a skeleton of a (meth)acrylic nature onto which are grafted monomers with hydrophilic functions, of the alcoxy- or hydroxy-polyakylene glycol type. These polymers are hereafter designated as “hydrophilic (meth)acrylic comb-branched polymers”.
  • the present invention which, relies on combining these methacrylic comb-branched polymers having a grafted monomer with a hydrophilic function, with an ASE (alkali-soluble emulsion) associative acrylic thickener, makes it possible to advantageously remedy this drawback.
  • ASE alkali-soluble emulsion
  • these polymers Once adsorbed onto the surface of the cement particles, these polymers, which are negatively charged, cause a phenomenon of electrostatic repulsion, which is the impetus for the cement particle dispersion mechanism; they require a dosage of about 0.4% solids content of the polymer in relation to the solids content of the cement, as instructed in the document “Superplasticizers for extending workability” (International Conference on superplasticizers and other chemical admixtures in concrete, Sorrento Italy, Oct. 29-Nov. 1, 2006, supplementary paper, Ed. Malhotra, American Concrete Institute, pp. 263-277)
  • This improved water-reducing power is explained by the existence of a steric repulsion mechanism relating to the presence of the side-chains, in combination with the electrostatic repulsion phenomenon caused by the anionic carboxylic groups.
  • This improvement leads to the ability to use a lower quantity of the polymer (on the order of 0.2% solids content in relation to the cement's solids content) for a consistency comparable to that obtained with the first-generation products.
  • the fluidifying effect acts against the dispersion mechanism: the distribution of the components is no longer even throughout the formulation, which negatively impacts its mechanical properties.
  • the initial fluidifying power is so noteworthy that it leads to segregation, i.e. a physical separation of the medium's various components. This issue is recounted in the document WO 2007/047407.
  • ASE (alkali soluble emulsion) thickeners designate thickeners in an emulsion which are copolymers of (meth)acrylic acid with an ester of these acids.
  • HASE hydrophobically modified alkali-soluble emulsions
  • thickeners are different from HASE (hydrophobically modified alkali-soluble emulsions) polymers, which designate thickeners in an emulsion which are copolymers of (meth)acrylic acid, an ester of these acids, and a hydrophobic monomer.
  • ASE polymers in the form of dispersions when in an acidic state, only become soluble once neutralized. By neutralizing the medium, an ionic repulsion mechanisms is caused between the various carboxylate groups carried by the polymer chain. These ionized groups polarize a large quantity of water molecules, which causes the medium's viscosity to increase.
  • HASE polymers involve interactions between the hydrophobic groups, which also contributes to thickening the medium.
  • hydrophobic (meth)acrylic comb-branched copolymers when used in an aqueous formulation with a hydraulic binder base in the presence of a hydrophilic (meth)acrylic comb-branched copolymer, the result is a very large increase in the dose of the hydrophilic comb-branched copolymer in relation to the prior art, without segregating or altering the mechanical properties: quantities greater than 0.6% solids content of hydrophilic comb-branched polymer in relation to the weight of the cement are achieved.
  • a first object of the invention consists of the use, as an agent improving the workability of an aqueous formula with a hydraulic binder base, of:
  • this use as an agent improving the workability of an aqueous formula with a hydraulic binder base is further characterized in that said comb-branched copolymer a) and said acrylic polymer b) are added to said aqueous formulation separately.
  • this use as an agent improving the workability of an aqueous formulation with a hydraulic binder base is further characterized in that said comb-branched copolymer a) and said acrylic polymer b) are added in the form of a mixture.
  • the mixture has a solids content between 10% and 50% of its total weight.
  • the mixture has a dry solids content of comb-branched copolymer a) of between 5% and 95%, and more preferably between 10% and 90% of its total solid matter.
  • ASE acrylic polymers b) are made up of (meth)acrylic acid and an ester of these acids.
  • comb-branched copolymer a) and acrylic polymer b) may be obtained by radical polymerization in a solution, direct emulsion, or inverse emulsion, in a suspension or precipitation in solvents, in the presence of catalytic systems and transfer agents, or by radical mediated polymerization and more preferably by nitroxide mediated polymerization (NMP) or cobaloxyme mediated polymerization, by atom transfer radical polymerization (ATRP), or by radical mediated polymerization by sulfur derivatives, chosen from among carbamates, dithioesters or trithiocarbonatcs (RAFT) or xanthates.
  • NMP nitroxide mediated polymerization
  • ATRP atom transfer radical polymerization
  • sulfur derivatives chosen from among carbamates, dithioesters or trithiocarbonatcs (RAFT) or xanthates.
  • This use is further characterized in that comb-branched copolymer a) and acrylic polymer b) are distilled, after polymerization.
  • This use is further characterized in that comb-branched copolymer a) and acrylic polymer b) are separated into several phases, using static or dynamic separation processes, by one or more polar solvents more preferably belonging to the group formed by water, methanol, ethanol, propanol, isopropanol, butanols, acetone, tetrahydrofurane, and mixtures thereof.
  • comb-branched copolymer a) and acrylic polymer b) are fully or partially neutralized by one or more neutralization agents having a monovalent or polyvalent cation, said agents more preferably being chosen from among ammonium hydroxide or from among calcium or magnesium hydroxides and/or oxides, or from among sodium, potassium, or lithium hydroxides, or from among primary, secondary, and tertiary aliphatic and/or cyclic amines and more preferably stearylamine, ethanolamines (mono-, di-, triethanolamine), mono- and diethylamine, cyclohexylamine, methylcyclohexylamine, amino-methyl-propanol, morpholine, and more preferably in that the neutralization agent is chosen from among triethanolamine and sodium hydroxide.
  • This use as an agent improving the workability of an aqueous formulation with a hydraulic binder base is further characterized in that said formulation is a cement, a mortar, a concrete, or a grout, and more preferably a concrete.
  • said aqueous formulation with a hydraulic binder base contains 0.1% 2%, more preferably 0.2% to 1%, and very preferably 0.4% to 0.8% solids content of components a) and b) in relation to the solid content of hydraulic binder.
  • Another object of the invention consists of an aqueous formulation with a hydraulic binder base, containing as an agent improving its workability:
  • This formulation is further characterized in that said comb-branched copolymer a) is made up of, expressed as a percentage by weight of each of its monomers, the sum of these percentages being equal to 100%:
  • This formulation is further characterized in that said ASE acrylic polymers b) are made up of (meth)acrylic acid and an ester of these acids, and (meth)acrylic acid and an ester of these acids.
  • comb-branched copolymer a) and acrylic polymer b) may be obtained by radical polymerization in a solution, direct emulsion, or inverse emulsion, in a suspension or precipitation in solvents, in the presence of catalytic systems and transfer agents, or by radical mediated polymerization and more preferably by nitroxide mediated polymerization (NMP) or by cobaloxyme mediated polymerization, by atom transfer radical polymerization (ATRP), by radical mediated polymerization by sulfur derivatives, chosen from among carbamates, dithioesters or trithiocarbonates (RAFT) or xanthates.
  • NMP nitroxide mediated polymerization
  • ATRP atom transfer radical polymerization
  • sulfur derivatives chosen from among carbamates, dithioesters or trithiocarbonates (RAFT) or xanthates.
  • This formulation is further characterized in that comb-branched copolymer a) and acrylic polymer b) are distilled, after polymerization.
  • This formulation is further characterized in that comb-branched copolymer a) and acrylic polymer b) are separated into several phases, using static or dynamic separation processes, by one or more polar solvents more preferably belonging to the group formed by water, methanol, ethanol, propanol, isopropanol, butanols, acetone, tetrahydrofurane, and mixtures thereof.
  • This formulation is further characterized in that comb-branched copolymer a) and acrylic copolymer b) are fully or partially neutralized by one or more neutralization agents having a monovalent or polyvalent cation, said agents being more preferably chosen from among ammonium hydroxide or from among calcium or magnesium hydroxides and/or oxides, or from among sodium, potassium, or lithium hydroxides, or from among primary, secondary, and tertiary aliphatic and/or cyclic amines and more preferably stearylamine, ethanolamines (mono-, di-, triethanolamine), mono- and diethylamine, cyclohexylamine, methylcyclohexylamine, amino-methyl-propanol, morpholine, and more preferably in that the neutralization agent is chosen from among triethanolamine and sodium hydroxide.
  • This formulation is further characterized in that it is a cement, a mortar, a concrete, or a grout, and more preferably a concrete.
  • This formulation is further characterized in that it contains 0.1% to 2%, more preferably 0.2% to 1%, and very preferably 0.4% to 0.8% solids content of components a) and b) in relation to the solid content of hydraulic binder.
  • the molecular mass of the polymers used in aqueous solutions a) are determined using a multi-detection steric exclusion chromatography (SEC 3D) technique, as indicated in the document FR 2,917,091.
  • SEC 3D multi-detection steric exclusion chromatography
  • the masses of the polymers used in aqueous solutions b) are determined using a steric exclusion chromatography technique, as indicated in the document FR 2,907,347.
  • the polymers used are obtained by polymerization techniques which are well-known to the person skilled in the art.
  • the dry materials are mixed for 1 minute.
  • the mixing of the blend is then continued for 7 minutes.
  • the slump is then measured with an Abraham cone using the method described in the AFNOR EN 12350-2 standard. This first measurement corresponds to the initial slump value, whose change is tracked over time.
  • the slump of values has been depicted in FIG. 1 , in centimeters of slump over time in minutes.
  • the dotted curve with round symbols relates to Test 1 in accordance with the prior art, in which it is necessary to add product to compensate for the loss of workability (relative to the slump measurement).
  • the dotted curve with square symbols relates to Test 2 according to the prior art, in which the product is overdosed.
  • the solid curve with round symbols relates to Test 3 according to the invention, which uses two products added separately.
  • the solid curve with square symbols relates to Test 4 according to the invention, which uses two products added as a mixture.
  • the product is (hydrophilic comb-branched polymer) used is therefore 0.40% solids content of the copolymer in relation to the cement's solids content, which corresponds to the dose normally used by the person skilled in the art.
  • the dose of the product (a hydrophilic comb-branched polymer) that is used is equal to 0.62% by solids content in relation to the solids content of the cement: this illustrates an “overdosage” test as sometimes practiced in the prior art.
  • FIG. 2 which is a photo representing the composition at the initial moment, once the Abraham cone has been removed, a very noteworthy segregation phenomenon appears, which is undesirable for the person skilled in the art.
  • the aqueous solution is initially added in the form of the mixture between solutions a) and b).
  • Tests 3 and 4 do not lead to any segregation phenomenon: however, they make it possible to overdose the quantity of hydrophilic comb-branched copolymer a) that is used.
  • the result is a workability that is at all points greater than that obtained for the prior art, without adding product later on.
  • the slump is then measured with an Abraham cone using the method described in the AFNOR EN 12350-2 standard. This first measurement corresponds to the initial slump value A 0 (cm). The same measurement is taken after 180 minutes A 180 (cm).
  • the concrete is checked to verify there is no segregation, and then the change in the slump value is checked after 180 minutes.
  • hydrophilic comb-branched copolymer a in relation to the solids content of cement.
  • hydrophilic comb-branched copolymer a in relation to the solids content of cement.
  • hydrophilic comb-branched copolymer a in relation to the solids content of cement.
  • hydrophilic comb-branched copolymer a in relation to the solids content of cement.
  • hydrophilic comb-branched copolymer a in relation to the solids content of cement.
  • hydrophilic comb-branched copolymer a in relation to the solids content of cement.
  • the invention successfully increases the dose of aqueous solution a).

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Ceramic Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US13/126,021 2008-12-08 2009-11-25 Use as an agent improving the workability of an aqueous formulation with a hydraulic binder base, of a (meth)acrylic comb-branched copolymer and an associative acrylic thickener Abandoned US20110207856A1 (en)

Applications Claiming Priority (3)

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FR0858346 2008-12-08
FR0858346A FR2939428B1 (fr) 2008-12-08 2008-12-08 Utilisation comme agent ameliorant la maniabilite d'une formulation aqueuse a base de liants hydrauliques, d'un copolymere (meth) acrylique peigne et d'un epaississant acrylique associatif
PCT/IB2009/007589 WO2010067155A1 (fr) 2008-12-08 2009-11-25 Utilisation comme agent améliorant la maniabilité d'une formulation aqueuse à base de liants hydrauliques, d'un copolymère (méth)acrylique peigne et d'un épaississant acrylique associatif

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US14/510,186 Continuation US9850374B2 (en) 2008-12-08 2014-10-09 Use as an agent improving the workability of an aqueous formulation with a hydraulic binder base, of a (meth)acrylic comb-branched copolymer and an associative acrylic thickener

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US14/510,186 Expired - Fee Related US9850374B2 (en) 2008-12-08 2014-10-09 Use as an agent improving the workability of an aqueous formulation with a hydraulic binder base, of a (meth)acrylic comb-branched copolymer and an associative acrylic thickener

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US (2) US20110207856A1 (enExample)
EP (1) EP2370485A1 (enExample)
JP (1) JP5607644B2 (enExample)
KR (1) KR20110112323A (enExample)
CN (1) CN102239193B (enExample)
BR (1) BRPI0922138A2 (enExample)
CA (1) CA2740641C (enExample)
FR (1) FR2939428B1 (enExample)
RU (1) RU2503632C2 (enExample)
WO (1) WO2010067155A1 (enExample)
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CN103554387A (zh) * 2013-11-04 2014-02-05 上海三瑞高分子材料有限公司 一种增稠剂共聚物及其制备方法和用途
CN105542096A (zh) * 2015-12-22 2016-05-04 四川大学 一种具有高效减水功能的嵌段共聚物及其制备方法与应用
FR3030307A1 (fr) * 2014-12-23 2016-06-24 Coatex Sas Polymere multiphasique a titre d'agent epaississant et suspensif

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FR2973241B1 (fr) 2011-03-28 2013-04-19 Coatex Sas Polymeres peignes pour les cheveux
FR2974502B1 (fr) 2011-04-26 2013-05-24 Coatex Sas Utilisation de copolymeres acryliques peignes comme agent developpeur de couleur dans des compositions cosmetiques.
FR2993278B1 (fr) * 2012-07-13 2016-02-19 Coatex Sas Utilisation d'un polymere peigne pour preparer une suspension contenant du carbonate de calcium et presentant une sensibilite a la temperature reduite.
US20170369371A1 (en) * 2014-12-22 2017-12-28 Dow Global Technologies Llc Derivatized polyimides and methods of making and using
WO2017058802A1 (en) * 2015-09-28 2017-04-06 Terravia Holdings, Inc. Triglyceride oils having asymmetric triglyceride molecules
CN105669913B (zh) * 2016-03-03 2018-03-13 江苏中铁奥莱特新材料股份有限公司 一种分子结构可控的星型聚羧酸系减水剂的制备方法
JP6966254B2 (ja) * 2016-08-03 2021-11-10 株式会社日本触媒 ポリカルボン酸系共重合体と消泡剤とを含むセメント用添加剤、およびセメント組成物
JP6821250B2 (ja) * 2016-12-16 2021-01-27 花王株式会社 水硬性組成物の硬化体の製造方法
JP6837824B2 (ja) * 2016-12-16 2021-03-03 花王株式会社 水硬性組成物
WO2020115790A1 (ja) * 2018-12-03 2020-06-11 竹本油脂株式会社 水硬性組成物用添加剤及び水硬性組成物

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EP2370485A1 (fr) 2011-10-05
FR2939428A1 (fr) 2010-06-11
RU2503632C2 (ru) 2014-01-10
FR2939428B1 (fr) 2010-11-19
JP2012510949A (ja) 2012-05-17
CA2740641A1 (fr) 2010-06-17
US20150051319A1 (en) 2015-02-19
BRPI0922138A2 (pt) 2016-01-05
CA2740641C (fr) 2017-12-19
WO2010067155A1 (fr) 2010-06-17
RU2011127994A (ru) 2013-01-20
ZA201102634B (en) 2012-07-25
US9850374B2 (en) 2017-12-26
JP5607644B2 (ja) 2014-10-15

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