WO2016026346A1 - Procédé à basse température de préparation de réducteur d'eau d'acide éther polycarboxylique à haute adaptabilité - Google Patents

Procédé à basse température de préparation de réducteur d'eau d'acide éther polycarboxylique à haute adaptabilité Download PDF

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Publication number
WO2016026346A1
WO2016026346A1 PCT/CN2015/081810 CN2015081810W WO2016026346A1 WO 2016026346 A1 WO2016026346 A1 WO 2016026346A1 CN 2015081810 W CN2015081810 W CN 2015081810W WO 2016026346 A1 WO2016026346 A1 WO 2016026346A1
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WIPO (PCT)
Prior art keywords
acid
parts
reducing agent
ether
water
Prior art date
Application number
PCT/CN2015/081810
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English (en)
Chinese (zh)
Inventor
方云辉
蒋卓君
柯余良
林艳梅
苏晋升
钟丽娜
张小芳
陈小路
郭鑫祺
林添兴
Original Assignee
科之杰新材料集团有限公司
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Application filed by 科之杰新材料集团有限公司 filed Critical 科之杰新材料集团有限公司
Priority to PH12015502804A priority Critical patent/PH12015502804A1/en
Publication of WO2016026346A1 publication Critical patent/WO2016026346A1/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
    • 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
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • 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
    • C04B24/16—Sulfur-containing 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
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • 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
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • 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
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (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
    • C08F228/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
    • C08F228/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur by a bond to sulfur
    • 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
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/40—Redox systems

Definitions

  • the invention belongs to the technical field of building materials, in particular to a low-temperature preparation method of a highly adaptable ether polycarboxylic acid water reducing agent.
  • the polycarboxylate water-reducing agent can synthesize the polymerizable structural unit into a predetermined structure and performance water-reducing agent by radical copolymerization according to molecular design principles, usually from a carboxylic acid group, a sulfonic acid group or an ester group. Some monomers having an unsaturated group such as a polyoxyethylene group are synthesized by a radical copolymerization reaction. In the molecular bonding process of the polymer, different monomers are randomly or regularly polymerized to make the molecule have a comb structure, and its special structure determines its superior performance.
  • the technical problem to be solved by the present invention is to provide a highly adaptable ether polycarboxylate water reducing agent and a low temperature preparation method thereof, which can overcome the problems and deficiencies in the prior art and production, and can be synthesized by using a heatless source process.
  • the technical solution of the present invention is:
  • a low-temperature preparation method of a highly adaptable ether polycarboxylic acid water reducing agent comprising the following steps:
  • reaction temperature is adjusted to 10-40 ° C, 0.1-3 parts of the oxidizing agent is added in one portion, and stirred to dissolve.
  • the mixed solution A and the mixed solution B are simultaneously added dropwise, and the dropping time is 2-4 h;
  • the unsaturated carboxylic acid is one or both of acrylic acid, methyl acrylate, ethyl acrylate, hydroxymethyl acrylate, hydroxyethyl acrylate, and itaconic acid.
  • the unsaturated sulfonate is one of sodium vinyl sulfonate, sodium allyl sulfonate, sodium methacrylate sulfonate, and sodium styrene sulfonate.
  • the unsaturated phosphonic acid is one of isopropenylphosphonic acid, 2-acrylamido-2-methylpropylphosphonic acid, dimethyl allylphosphonate, and diethyl allylphosphonate.
  • the chain transfer agent is one of 2-mercaptoacetic acid and 3-mercaptopropionic acid.
  • the reducing agent C is 2-hydroxy-2-sulfinic acid acetic acid, 2-hydroxy-2-sulfinic acid disodium salt, 2-hydroxy-2-sulfonic acid acetic acid, 2-hydroxy-2 One or both of the sulfonic acid acetic acid disodium salts.
  • the unsaturated polyoxyethylene ether is allyl polyoxyethylene ether, methallyl polyoxyethylene ether, isopentenyl polyoxyethylene ether, 4-hydroxybutyl vinyl ether polyoxygen One of the vinyl ethers.
  • the buffering agent is one of disodium hydrogen phosphate and sodium hydrogencarbonate.
  • the oxidizing agent is one of hydrogen peroxide, sodium peroxide, lithium peroxide, sodium persulfate, potassium persulfate, ammonium persulfate, sodium peroxodisulfate, potassium peroxoborate or peracetic acid.
  • the reducing agent D is one of a white block, ascorbic acid, and sodium sulfite.
  • the present invention has the following effective effects:
  • the preparation method of the invention adopts a redox system initiation system with low activation energy, which improves the reaction activity and reduces the occurrence of side reactions, so that the conversion rate of the product is high, and can reach about 99%.
  • the preparation method of the invention can be polymerized at normal temperature, is easy for industrial production, has simple process, and does not require heating in production, and is a green environmental protection process.
  • the preparation method of the invention adopts the introduction of carboxylate, sulfonate and phosphonate groups to improve the dispersibility and dispersibility retention ability of the product, and the adaptability to the cementitious material.
  • the mixed solution A and the mixed solution B were simultaneously added dropwise, and the dropping time was 2 h; after the completion of the dropwise addition, the reaction was continued for 1 hour; finally, 10 kg of a 30% by mass sodium hydroxide solution was added for neutralization, thereby obtaining the above-mentioned Polycarboxylate water reducing agent, monomer conversion rate of 98.9%.
  • the mixed solution A and the mixed solution B are simultaneously added dropwise, and the dropping time is 3 hours; after the dropping is completed, the mixture can be added at one time.
  • 0.3 kg of ascorbic acid was further reacted for 1 hour; finally, 15 kg of a 30% by mass sodium hydroxide solution was added for neutralization to obtain the polycarboxylic acid water reducing agent, and the monomer conversion rate was 98.7%.
  • the sample obtained by the synthesis of Examples 1-4 and the comparative example were made of standard cement, China Resources Cement PO.42.5, sinter cement PO.42.5, ⁇ cement PO.42.5, The amount of cement is 0.2% according to the quality of the cement. According to GB 8076-2008 "Concrete admixture", the concrete water reduction rate is measured. Concrete mix was: Cement 360kg / m 3, sand 803kg / m 3, stone 982kg / m 3, slump control 210 ⁇ 10mm, the obtained results are shown in Table.
  • the invention adopts a redox system initiation system with low activation energy, improves the reaction activity, and improves the dispersibility and dispersibility retention ability of the product and the adaptation to the cement material by introducing carboxylate, sulfonate and phosphonate groups. Sex.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Ceramic Engineering (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé à basse température de préparation de réducteur d'eau d'acide éther polycarboxylique à haute adaptabilité. Le procédé comprend les étapes suivantes : la formulation d'acide carboxylique insaturé, de sulfonate insaturé, d'acide phosphonique insaturé, d'agent de transfert de chaîne et d'eau en une solution mélangée A; la formulation d'agent réducteur C et d'eau en une solution mélangée B; l'ajout d'éther de polyoxyéthylène insaturé, d'un agent tampon et d'eau dans une cuve de réaction; l'ajustement de la température de réaction à 10 à 40°C, l'addition d'un oxydant en une fois et la dissolution par agitation; respectivement et simultanément l'addition goutte à goutte de la solution mélangée A et de la solution mélangée B; à la fin de l'addition goutte à goutte, l'ajout de 0 à 0,5 partie de réducteur D en une fois, en faisant réagir en continu pendant 1-2 heures; et l'ajout de 10 à 20 parties de 30% en poids d'une solution d'hydroxyde de sodium afin de neutraliser, ce qui permet d'obtenir un réducteur d'eau d'acide polycarboxylique. Le procédé de la présente invention est simple. Le réducteur d'eau préparé peut avoir une dispersibilité élevée par une faible quantité de dopage. Le réducteur à basse température à haute efficacité est introduit pour mettre en oeuvre la polymérisation à basse température de l'acide polycarboxylique, ce qui permet d'améliorer le taux de conversion du produit.
PCT/CN2015/081810 2014-08-22 2015-06-18 Procédé à basse température de préparation de réducteur d'eau d'acide éther polycarboxylique à haute adaptabilité WO2016026346A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PH12015502804A PH12015502804A1 (en) 2014-08-22 2015-12-17 Method for preparing high-adaptable ether polycarboxylate superplasticizer at low temperature

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CN201410417642.1 2014-08-22
CN201410417642.1A CN104177557B (zh) 2014-08-22 2014-08-22 一种高适应性醚类聚羧酸减水剂的低温制备方法

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