WO2000012576A1 - Procede de production de polymere d'acide (meth)acrylique - Google Patents

Procede de production de polymere d'acide (meth)acrylique Download PDF

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Publication number
WO2000012576A1
WO2000012576A1 PCT/JP1999/004276 JP9904276W WO0012576A1 WO 2000012576 A1 WO2000012576 A1 WO 2000012576A1 JP 9904276 W JP9904276 W JP 9904276W WO 0012576 A1 WO0012576 A1 WO 0012576A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
weight
acid
parts
Prior art date
Application number
PCT/JP1999/004276
Other languages
English (en)
Japanese (ja)
Inventor
Kengo Shibata
Haruya Minou
Haruyuki Sato
Toshinao Ukena
Original Assignee
Kao Corporation
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 Kao Corporation filed Critical Kao Corporation
Publication of WO2000012576A1 publication Critical patent/WO2000012576A1/fr

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Classifications

    • 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
    • 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
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
    • C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
    • 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
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers

Definitions

  • the present invention relates to a method for producing a (meth) acrylic acid-based polymer useful as a dispersant for cement for improving the dispersibility of cement particles in a hydraulic composition such as cement paste, mortar, and concrete.
  • Step 2 A step of copolymerizing PGMA (meth) acrylate and a monomer copolymerizable with PGMA (meth) acrylate in the range of pH 1.5 to 3.5.
  • alkyl (meth) acrylate refers to both alkyl acrylate and alkyl methacrylate
  • PGMA (meth) acrylate refers to both acrylate and methacrylate.
  • the amount of the acid catalyst or the basic catalyst used is preferably from 0.1 to 10 parts by weight based on 100 parts by weight of dalicol ether. When the amount is 0.1 part by weight or more, the reaction rate can be maintained at an appropriate level, and when the amount is 10 parts by weight or less, it is economical.
  • an alkali agent is added to deactivate the acid catalyst.
  • the alkaline agent include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide.
  • the amount of the alkali agent to be used is preferably 0.9 to 1.5 equivalent times, more preferably 1.0 to 1.3 equivalent times, relative to the acid catalyst used.
  • (meth) acrylic acid methyl (meth) acrylate or methoxypolyethylene glycol mono (meth) acrylate is preferred, and methacrylic acid is preferred. Particularly preferred.
  • Examples of the acid used for adjusting the pH include phosphoric acid, sulfuric acid, nitric acid, alkylphosphoric acid, alkynoleic acid, alkylsulfonic acid, alkylbenzenesulfonic acid, benzenesulfonic acid and the like.
  • phosphoric acid is preferred because it has a pH buffering action, easily adjusts pH to a predetermined range, and can suppress foaming of the polymerization reaction system.
  • the reaction can be performed in the presence of a solvent to reduce the viscosity of the polymerization reaction system.
  • Step 1 of Example 1 100 parts by weight of polyethylene glycol monomethyl ether (number of moles of added ethylene oxide 9, weight average molecular weight 4229), 1200 parts by weight of methyl methacrylate and 40 parts by weight of p-toluenesulfonic acid
  • An esterification reaction product (A) -3 was obtained in the same manner as in Example 1 except for using parts by weight.
  • the methacrylate concentration of this (A) -3 was 93.4%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un procédé de production d'un polymère d'acide (méth)acrylique convenant pour être utilisé comme dispersant de ciment de qualité stable. Le procédé comporte les étapes consistant à : 1) soumettre un (méth)acrylate d'alkyle et un éther monoalkyle de polyalkylène glycol à une transestérification selon un rapport molaire se situant entre 5/1 et 50/1, puis distiller le sous-produit d'alcool et le reste de (méth)acrylate d'alkyle pour obtenir un produit d'estérification contenant un (méth)acrylate PGMA ; et 2) copolymériser le (méth)acrylate PGMA présent dans le produit d'estérification avec un monomère pouvant être copolymérisé avec celui-ci dans la plage de pH de 1,5 à 3,5.
PCT/JP1999/004276 1998-08-27 1999-08-06 Procede de production de polymere d'acide (meth)acrylique WO2000012576A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10/241256 1998-08-27
JP24125698 1998-08-27

Publications (1)

Publication Number Publication Date
WO2000012576A1 true WO2000012576A1 (fr) 2000-03-09

Family

ID=17071544

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/JP1999/004276 WO2000012576A1 (fr) 1998-08-27 1999-08-06 Procede de production de polymere d'acide (meth)acrylique
PCT/JP1999/004527 WO2000012577A1 (fr) 1998-08-27 1999-08-23 Procede de production d'un polymere d'acide (meth)acrylique

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/JP1999/004527 WO2000012577A1 (fr) 1998-08-27 1999-08-23 Procede de production d'un polymere d'acide (meth)acrylique

Country Status (1)

Country Link
WO (2) WO2000012576A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007029837A1 (fr) * 2005-09-05 2007-03-15 Kao Corporation Procédé de production d’un polymère phosphaté
JP4137445B2 (ja) * 1999-08-23 2008-08-20 花王株式会社 （メタ）アクリル酸系重合体の製造方法
CN100487011C (zh) * 2005-05-09 2009-05-13 中国科学院过程工程研究所 聚乙二醇改性的甲基丙烯酸缩水甘油酯树脂及制备方法和应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004059489C5 (de) 2004-12-10 2011-12-08 Clariant Produkte (Deutschland) Gmbh Verfahren zur Herstellung von reinen alpha-Alkoxy-omega-hydroxy-Polyalkylenglykolen

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS3620385B1 (fr) * 1960-08-01 1961-10-25
JPS4842473B1 (fr) * 1970-11-19 1973-12-12
JPS5092985A (fr) * 1973-12-24 1975-07-24
JPS53126093A (en) * 1977-04-12 1978-11-02 Japan Exlan Co Ltd Preparation of aqueous polymer emulsion having modified stability
JPH09267034A (ja) * 1996-04-01 1997-10-14 Toyo Ink Mfg Co Ltd 消泡性ノニオン系高分子界面活性剤及びその用途

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS3620385B1 (fr) * 1960-08-01 1961-10-25
JPS4842473B1 (fr) * 1970-11-19 1973-12-12
JPS5092985A (fr) * 1973-12-24 1975-07-24
JPS53126093A (en) * 1977-04-12 1978-11-02 Japan Exlan Co Ltd Preparation of aqueous polymer emulsion having modified stability
JPH09267034A (ja) * 1996-04-01 1997-10-14 Toyo Ink Mfg Co Ltd 消泡性ノニオン系高分子界面活性剤及びその用途

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4137445B2 (ja) * 1999-08-23 2008-08-20 花王株式会社 （メタ）アクリル酸系重合体の製造方法
CN100487011C (zh) * 2005-05-09 2009-05-13 中国科学院过程工程研究所 聚乙二醇改性的甲基丙烯酸缩水甘油酯树脂及制备方法和应用
WO2007029837A1 (fr) * 2005-09-05 2007-03-15 Kao Corporation Procédé de production d’un polymère phosphaté
CN101277986B (zh) * 2005-09-05 2010-09-15 花王株式会社 磷酸酯类聚合物的制造方法
US7964682B2 (en) 2005-09-05 2011-06-21 Kao Corporation Method for producing phosphoric acid ester-based polymer

Also Published As

Publication number Publication date
WO2000012577A1 (fr) 2000-03-09

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