EP1727835A1 - Polymere presentant des groupes amide et ester, procede pour le produire et utilisation de celui-ci - Google Patents

Polymere presentant des groupes amide et ester, procede pour le produire et utilisation de celui-ci

Info

Publication number
EP1727835A1
EP1727835A1 EP05733482A EP05733482A EP1727835A1 EP 1727835 A1 EP1727835 A1 EP 1727835A1 EP 05733482 A EP05733482 A EP 05733482A EP 05733482 A EP05733482 A EP 05733482A EP 1727835 A1 EP1727835 A1 EP 1727835A1
Authority
EP
European Patent Office
Prior art keywords
group
acid
carbon atoms
compound
polymer
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Withdrawn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
EP05733482A
Other languages
German (de)
English (en)
Inventor
Ueli Sulser
Irene Schober
Ulf Velten
Anna Krapf
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.)
Sika Technology AG
Original Assignee
Sika Technology AG
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 Sika Technology AG filed Critical Sika Technology AG
Priority to EP05733482A priority Critical patent/EP1727835A1/fr
Publication of EP1727835A1 publication Critical patent/EP1727835A1/fr
Withdrawn legal-status Critical Current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
    • C04B24/2641—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
    • C04B24/2688—Copolymers containing at least three different monomers
    • C04B24/2694—Copolymers containing at least three different monomers containing polyether side chains
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/14—Esterification
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/48—Isomerisation; Cyclisation
    • 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
    • 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
    • C04B2103/40—Surface-active agents, dispersants
    • C04B2103/408—Dispersants

Definitions

  • (Meth) acrylic acid throughout the present document means both acrylic acid and methacrylic acid ure understood.
  • the homo- or copolymer P1 of (meth) acrylic acid can be present as a free acid, as a full or partial salt, the term “salt” here and below, in addition to the classic salts as obtained by neutralization with a base, also Complex chemical connections between metal ions and the carboxylate or carboxyl groups as ligands.
  • Methacrylic acid and its salts or partial salts are typically obtained after the radical polymerization.
  • Preferred homopolymer P1 is polymethacrylic acid or polyacrylic acid, in particular polymethacrylic acid, their salts or partial salts.
  • the salts or partial salts are typically obtained after the radical polymerization.
  • P1 is preferably a homopolymer.
  • the homo- or copolymer P1 of (meth) acrylic acid is obtained by a radical polymerization according to conventional methods. It can be carried out in solvent, preferably in water or in bulk.
  • this first step is carried out in the presence of an esterification catalyst, in particular an acid.
  • an esterification catalyst in particular an acid.
  • Such acid is preferably sulfuric acid, p-toluenesulfonic acid, benzenesulfonic acid, methanesulfonic acid, phosphoric acid or phosphorous acid. Sulfuric acid is preferred.
  • the water is removed from the reaction mixture can be carried out under atmospheric pressure or under vacuum, or a gas stream can be passed over or through the reaction mixture, air or nitrogen can be used as the gas stream.
  • the monoamine compound A ' is preferably a primary monoamine.
  • R 4 here represents a C1 to C4 alkylene group.
  • R 5 represents a Cp to C 4 alkyl group.
  • R 6 represents an alkylene group, optionally with heteroatoms, and forms a 5-er to 8-er with the nitrogen atom Ring, especially a 6-ring.
  • the substituent R 1 and the indices x, y and z have the meanings as have already been defined for the compound of the formula (I).
  • a solvent is preferably used for the reaction in the second step.
  • Preferred solvents are, for example, hexane, toluene, xylene, methylcyclohexane, cyclohexane or dioxane as well as alcohols, in particular ethanol or isopropanol, and water, water being the most preferred solvent.
  • the second step is carried out by introducing the amine in a solvent, preferably water, and for this purpose the product from the first reaction step as a polymer melt or else in solid form, for example as a powder or in the form of flakes, or a granulate is added with stirring. The addition as a polymer melt is preferred.
  • the amide and ester group-containing polymer P can be a component of a hydraulically setting composition, a so-called dry mixture, which can be stored for a long period of time and is typically packaged in or in bags Silos is stored and used.
  • the polymer P having amide and ester groups can also be added to a customary hydraulic setting composition with or shortly before or shortly after the addition of the water.
  • the addition of the polymer P having amide and ester groups has been shown to be suitable in the form of an aqueous solution or dispersion, in particular as mixing water or as part of the mixing water.
  • Example series 1 esterification / amidation and formation of hydrogen
  • a reaction vessel with stirrer, thermometer, vacuum connection and distillation device 960 g of a 40% aqueous solution
  • Mortar mix 1 MM1 (largest grain 8mm) amount of cement (Swiss CEM I 42.5) 750 g limestone filler 141 g sand 0-1 mm 738 g sand 1-4 mm 1107 g sand 4-8 mm 1154 g
  • the air content of the mortar was determined in accordance with EN 196-1.
  • the setting time was determined by means of the temperature development in a styrofoam kettle of approx. 11 contents filled with mortar.
  • the time at which the temperature curve has the maximum value was defined as the setting end.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Ceramic Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Polymerisation Methods In General (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Polyamides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyethers (AREA)

Abstract

La présente invention concerne un procédé pour produire un polymère (P) présentant des groupes amide et ester. Ce procédé consiste, dans une première étape, à mettre en réaction un homopolymère ou un copolymère P1 d'acide (méth)acrylique avec un composé monohydroxy E à une température allant jusqu'à 200 DEG C, de façon que des groupes anhydride apparaissent en plus des groupes ester, puis, dans une seconde étape, à mettre en réaction les groupes anhydride formés dans la première étape avec un composé monoamine A à une température nettement inférieure à 100 DEG C. Cette invention concerne également les polymères produits selon ledit procédé, leur utilisation dans des compositions à prise hydraulique, ainsi que ces compositions à prise hydraulique avant et après le durcissement au moyen d'eau.
EP05733482A 2004-03-19 2005-03-18 Polymere presentant des groupes amide et ester, procede pour le produire et utilisation de celui-ci Withdrawn EP1727835A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP05733482A EP1727835A1 (fr) 2004-03-19 2005-03-18 Polymere presentant des groupes amide et ester, procede pour le produire et utilisation de celui-ci

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP04006641A EP1577327A1 (fr) 2004-03-19 2004-03-19 Polymère comportant des groupes amide et ester, sa préparation et son utlisation
PCT/EP2005/051275 WO2005090416A1 (fr) 2004-03-19 2005-03-18 Polymere presentant des groupes amide et ester, procede pour le produire et utilisation de celui-ci
EP05733482A EP1727835A1 (fr) 2004-03-19 2005-03-18 Polymere presentant des groupes amide et ester, procede pour le produire et utilisation de celui-ci

Publications (1)

Publication Number Publication Date
EP1727835A1 true EP1727835A1 (fr) 2006-12-06

Family

ID=34833657

Family Applications (2)

Application Number Title Priority Date Filing Date
EP04006641A Withdrawn EP1577327A1 (fr) 2004-03-19 2004-03-19 Polymère comportant des groupes amide et ester, sa préparation et son utlisation
EP05733482A Withdrawn EP1727835A1 (fr) 2004-03-19 2005-03-18 Polymere presentant des groupes amide et ester, procede pour le produire et utilisation de celui-ci

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP04006641A Withdrawn EP1577327A1 (fr) 2004-03-19 2004-03-19 Polymère comportant des groupes amide et ester, sa préparation et son utlisation

Country Status (7)

Country Link
US (2) US7994259B2 (fr)
EP (2) EP1577327A1 (fr)
JP (1) JP2007529591A (fr)
CN (1) CN1946747B (fr)
AU (1) AU2005223399B2 (fr)
CA (1) CA2560208A1 (fr)
WO (1) WO2005090416A1 (fr)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2005254265B2 (en) * 2004-06-21 2010-07-29 Sika Technology Ag Cement grinding aid
EP1916265A1 (fr) * 2006-10-26 2008-04-30 Sika Technology AG Procédé de fabrication d'un polymère sous forme d'agrégés solides qui contient des groupes amide et ester.
EP2006258B1 (fr) * 2007-06-11 2012-08-15 Sika Technology AG Agent dispersant pour compositions de gypse
ES2359347T3 (es) 2007-10-29 2011-05-20 Sika Technology Ag Agentes dispersantes para sistemas que fraguan por medios hidráulicos.
ATE496875T1 (de) 2007-10-29 2011-02-15 Sika Technology Ag Dispergiermittel für hydraulisch abbindende systeme
JP4975714B2 (ja) * 2007-11-28 2012-07-11 ローム アンド ハース カンパニー ポリマーの製造法
EP2154118A1 (fr) * 2008-07-30 2010-02-17 Sika Technology AG Agent dispersant pour compositions de gypse
EP2159203A1 (fr) 2008-08-26 2010-03-03 Sika Technology AG Additif pour systèmes de raccordement hydraulique ayant une capacité de transformation améliorée et un taux de réduction d'eau réduit
EP2161247B1 (fr) 2008-09-05 2012-10-24 Sika Technology AG Procédé de stabilisation de polycarboxylates
EP2368863A1 (fr) * 2010-03-22 2011-09-28 Sika Technology AG Additif pour systèmes de détachement hydraulique ayant une capacité de traitement améliorée
EP2426095A1 (fr) 2010-09-03 2012-03-07 Sika Technology AG Agent dispersant pour compositions de gypse
EP2463314A1 (fr) * 2010-12-10 2012-06-13 Sika Technology AG Fabrication de polymères en peigne par transestérification
KR101811792B1 (ko) 2011-03-14 2017-12-22 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 폴리머 및 이의 조성물
WO2013020862A1 (fr) 2011-08-10 2013-02-14 Sika Technology Ag Procédé de séchage de dispersants de béton
EP2578608B1 (fr) * 2011-10-03 2014-02-26 Sika Technology AG Agent dispersant pour suspensions de matière solide
JP6289486B2 (ja) 2012-11-09 2018-03-07 シーカ・テクノロジー・アーゲー エポキシ樹脂用の分散剤として使用されるポリカルボキシレートエーテル
EP2784036A1 (fr) 2013-03-26 2014-10-01 Basf Se Composition sous forme de poudre pouvant être rapidement mise en suspension
EP2784038A1 (fr) 2013-03-26 2014-10-01 Basf Se Matière pouvant s'écouler sur des suppléments
EP2784040A1 (fr) 2013-03-26 2014-10-01 Basf Se Composition sous forme de poudre pouvant être rapidement mise en suspension
EP3041872A1 (fr) * 2013-09-06 2016-07-13 Sika Technology AG Éthers de polycarboxylate à base de matières biologiques et procédés pour les produire
WO2015059100A1 (fr) 2013-10-25 2015-04-30 Sika Technology Ag Sucre caramélisé comme fluidifiant pour des compositions de liant minéral
KR20150118527A (ko) * 2014-04-14 2015-10-22 제이엔씨 주식회사 액정 배향제, 액정 배향막 및 액정 표시 소자
US11021398B2 (en) 2015-10-26 2021-06-01 Sika Technology Ag Inerting clay minerals and improving the effect of liquefiers in clay-containing mineral binder compositions
DE102017213607A1 (de) 2017-08-04 2019-02-07 Evonik Röhm Gmbh Fließverbesserer und Wasserreduktionsmittel
EP3549961A1 (fr) 2018-04-03 2019-10-09 Evonik Röhm GmbH Agent améliorant l'écoulement du béton et agent de réduction d'eau
RU2020109396A (ru) 2017-08-04 2021-09-06 Рем Гмбх Улучшители текучести и водоредуцирующие добавки для бетона
DE102017213600A1 (de) 2017-08-04 2019-02-07 Evonik Röhm Gmbh Beton-Fließverbesserer
CN112672985A (zh) 2018-10-05 2021-04-16 Sika技术股份公司 作为膨胀粘土的封闭添加剂的梳型聚合物
EP3789359A1 (fr) 2019-09-03 2021-03-10 Sika Technology AG Utilisation de polymères en peigne en tant qu'agents d'inertage pour des silicates en couches non gonflants
EP3939947A1 (fr) 2020-07-15 2022-01-19 Sika Technology Ag Additifs de blocage d'argile pour compositions de gypse
US20220185733A1 (en) 2020-12-11 2022-06-16 Sika Technology Ag Cementitious compositions comprising oxidatively degraded polysaccharide as water reducing agents
EP4299547A1 (fr) 2022-06-28 2024-01-03 Sika Technology AG Compositions de mortier sans danger pour l'environnement

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CA2224782C (fr) * 1995-06-21 2002-11-26 W.R. Grace & Co.-Conn. Superplastifiants permettant une regulation de l'air
EP0889860B1 (fr) 1996-03-26 2000-05-10 ARCO Chemical Technology, L.P. Additifs pour ciment
DE10015135A1 (de) * 2000-03-29 2001-10-04 Basf Ag Verfahren zur Modifizierung von Säuregruppen enthaltenden Polymerisaten
EP1138696A1 (fr) * 2000-03-29 2001-10-04 Sika AG, vorm. Kaspar Winkler & Co. Polymères pour compositions dispersantes pour ciment
FR2807045B1 (fr) * 2000-03-31 2004-02-27 Atofina Copolymeres acryliques hydrosolubles et leur utilisation comme fluidifiants ou dispersants
EP1348729A1 (fr) * 2002-03-25 2003-10-01 Sika Schweiz AG Polymères en état changeant solide

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Also Published As

Publication number Publication date
CN1946747A (zh) 2007-04-11
EP1577327A1 (fr) 2005-09-21
AU2005223399A1 (en) 2005-09-29
AU2005223399B2 (en) 2010-09-23
US7994259B2 (en) 2011-08-09
US20080021169A1 (en) 2008-01-24
CN1946747B (zh) 2010-11-24
CA2560208A1 (fr) 2005-09-29
WO2005090416A1 (fr) 2005-09-29
JP2007529591A (ja) 2007-10-25
US20110245379A1 (en) 2011-10-06

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