WO2021226869A1 - Agent réducteur d'eau à base d'acide polycarboxylique solide et son procédé de préparation - Google Patents

Agent réducteur d'eau à base d'acide polycarboxylique solide et son procédé de préparation Download PDF

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Publication number
WO2021226869A1
WO2021226869A1 PCT/CN2020/090002 CN2020090002W WO2021226869A1 WO 2021226869 A1 WO2021226869 A1 WO 2021226869A1 CN 2020090002 W CN2020090002 W CN 2020090002W WO 2021226869 A1 WO2021226869 A1 WO 2021226869A1
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WO
WIPO (PCT)
Prior art keywords
reducing agent
polycarboxylic acid
preparation
acid water
water reducing
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PCT/CN2020/090002
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English (en)
Chinese (zh)
Inventor
朱建民
刘兆滨
董振鹏
杨雪
张建东
Original Assignee
辽宁奥克化学股份有限公司
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.)
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Application filed by 辽宁奥克化学股份有限公司 filed Critical 辽宁奥克化学股份有限公司
Priority to DE112020007177.4T priority Critical patent/DE112020007177T5/de
Priority to PCT/CN2020/090002 priority patent/WO2021226869A1/fr
Publication of WO2021226869A1 publication Critical patent/WO2021226869A1/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
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • 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
    • C04B24/28—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/32—Polyethers, e.g. alkylphenol polyglycolether
    • 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
    • C08F2/02—Polymerisation in bulk
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
    • C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
    • C08G65/2624—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aliphatic amine groups
    • 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
    • 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

Definitions

  • the invention relates to the field of concrete admixtures, in particular to a solid polycarboxylic acid water reducing agent and a preparation method thereof.
  • Water reducer is an indispensable part in today's concrete industry, starting from the first generation of lignosulfonate series of ordinary water reducing agents, to the second generation of naphthalene-based water-reducing agents, melamine-based water-reducing agents, and amino High-efficiency water-reducing agents such as sulfonate-based water-reducing agents and fatty acid-based water-reducing agents, and to the current third-generation polycarboxylic acid-based high-performance water-reducing agents, each water-reducing agent has its own unique advantages; In particular, the polycarboxylic acid-based high-performance water-reducing agent is the most widely used concrete in today's concrete, and it has its presence in major projects.
  • the polycarboxylic acid-based water-reducing agents on the market are mainly mother liquor water agents, and the solid content of the product is generally about 40%-50%, which will increase the cost during transportation.
  • the application in engineering construction is restricted.
  • the mother liquor of water reducing agent can be directly converted into powder polycarboxylic acid by spray drying method, the spray drying method has high energy consumption, and some products will be lost during drying and production. Security Question.
  • CN108192041A discloses a preparation method and application of a powdered polycarboxylic acid water reducing agent, the preparation of a benzene ring-containing polycarboxylic acid water reducing agent and how to spray and dry it into a powdered polycarboxylic acid water reducing agent Method and application.
  • the preparation method includes: preparing a polycarboxylic acid monomer a, a small benzene ring-containing monomer b, and a benzene ring-containing polyether monomer c in an aqueous medium through free radical copolymerization to obtain a polycarboxylic acid water reducing agent Mother liquor; the polycarboxylic acid water-reducing agent mother liquor is directly passed through the centrifugal atomizer of the sprayer to form droplets without adding a release agent.
  • the average particle size of the powder is controlled to be 50-150um, and the droplets are dried after entering the drying chamber
  • the material is turned into powder, and the material is led to the discharge port through the induced draft fan, and the material is packaged and discharged by the bag packaging machine to obtain the powdery polyshuttle acid water reducing agent.
  • the invention will have a certain loss during the spray centrifugation process, and spray drying requires a higher temperature, and the energy consumption requirement under the same output is too high.
  • CN108484841A discloses a method for preparing a solid sheet-like polycarboxylic acid water-reducing agent by bulk polymerization.
  • the solid sheet-like polycarboxylic acid water-reducing agent is prepared by bulk polymerization, and a certain amount of just synthesized liquid polyether is monohydrated.
  • the process is relatively complicated in the synthesis process, and the higher reaction temperature causes a great loss of energy consumption.
  • the purpose of the present invention is to overcome the shortcomings of the prior art and provide a solid polycarboxylic acid water reducing agent with good workability and low production and transportation costs.
  • a preparation method of solid polycarboxylic acid water reducing agent including:
  • the mixed solution is subjected to aging treatment, and then cooled and solidified to obtain the solid polycarboxylic acid water reducing agent.
  • the added amount of the polyether monomer is 82-89%, the added amount of the hyperbranched monomer is 0.4-3%, and the unsaturated carboxylic acid
  • the addition amount of the chain transfer agent is 7-11%, the addition amount of the chain transfer agent is 0.2-0.7%, and the addition amount of the initiator is 0.4-1.5%.
  • the polyether monomer is selected from one or more of methallyl polyoxyethylene ether, prenol polyoxyethylene ether and hydroxybutyl polyoxyethylene ether, and The molecular weight of the polyether monomer is 1200-5000, preferably 2000-4000.
  • the hyperbranched monomer has a structure as shown in Formula I, wherein n is an integer from 1 to 15, m is an integer from 1 to 10, x is an integer from 1 to 10, and y is from 1 to 1. An integer of 10.
  • the initiator is selected from benzoyl peroxide, lauryl peroxide, ammonium persulfate, potassium persulfate, sodium persulfate, azobisisobutyronitrile, azobisisoheptonitrile, One or more of azobisisovaleronitrile, azobiscyclohexylcarbonitrile, dimethyl azodiisobutyrate, dicyclohexyl peroxydicarbonate, and hexadecyl peroxydicarbonate.
  • the unsaturated carboxylic acid is selected from one or more of acrylic acid, methacrylic acid, itaconic acid, maleic anhydride, maleic acid, and fumaric acid.
  • the chain transfer agent is selected from sodium methacrylate sulfonate, sodium allyl sulfonate, thioglycolic acid, mercaptopropionic acid, mercaptoethanol, n-dodecyl mercaptan, sodium hypophosphite, ethylene One or more of sodium sulfonate, sodium propenyl sulfonate and sodium styrene sulfonate.
  • the unsaturated carboxylic acid and the chain transfer agent are added to the liquid by dropping, and the dropping time is 0.5-2h.
  • the aging treatment time is 0.5-3h.
  • the present invention provides a solid polycarboxylic acid water reducing agent, which is prepared according to the above method.
  • the solid polycarboxylate water-reducing agent of the present invention Due to the addition of hyperbranched monomers, the solid polycarboxylate water-reducing agent of the present invention has reduced requirements for viscosity during polymerization, and has good workability to concrete in the process of concrete evaluation, without bleeding, bleeding, or bleeding. Phenomena such as stone leakage can reduce the viscosity of concrete under the condition of low water-cement ratio.
  • the method of the present invention can obtain an anhydrous solid polycarboxylic acid water reducing agent product after the preparation is completed, and it does not need to be spray-dried like the traditional mother liquor water agent to obtain the powder polycarboxylic acid water reducing agent, and the powder polycarboxylic acid water reducing agent Compared with the agent, the production cost and the long-distance transportation cost are greatly reduced.
  • the invention provides a preparation method of a solid polycarboxylic acid water reducing agent, which comprises the following steps:
  • the mixed solution is subjected to aging treatment, and then cooled and solidified to obtain the solid polycarboxylic acid water reducing agent.
  • the added amount of the polyether monomer is 82-89%, the added amount of the hyperbranched monomer is 0.4-3%, and the added amount of the unsaturated carboxylic acid is 7- 11%, the added amount of the chain transfer agent is 0.2-0.7%, and the added amount of the initiator is 0.4-1.5%.
  • the polyether monomer and the hyperbranched monomer first melt into a liquid within a certain temperature range.
  • the polyether monomer can be completely melted first, and then the hyperbranched monomer is added to melt.
  • the temperature of the chemical material can be controlled at 65-100°C.
  • the polyether monomer used in the present invention is selected from one or more of methallyl polyoxyethylene ether, prenol polyoxyethylene ether and hydroxybutyl polyoxyethylene ether, and the polyether monomer
  • the molecular weight is 1200-5000, preferably 2000-4000.
  • the hyperbranched monomer used in the present invention is a polymer obtained by adding polyvinyl polyamine as a raw material to random blocks of ethylene oxide and propylene oxide. It has a structure as shown in formula I, where n represents epoxy The addition number of ethane (EO), which is an integer of 1-15, preferably an integer of 3-10, m represents the addition number of propylene oxide (PO), which is an integer of 1-10, preferably 2 An integer of -6, x is an integer of 1-10, and y is an integer of 1-10.
  • EO epoxy
  • EO addition number of ethane
  • PO propylene oxide
  • x is an integer of 1-10
  • y is an integer of 1-10.
  • the initiator used in the present invention is an oil-soluble initiator, which is selected from the group consisting of benzoyl peroxide and ten Diacyl, ammonium persulfate, potassium persulfate, sodium persulfate, azobisisobutyronitrile, azobisisoheptonitrile, azobisisovaleronitrile, azobiscyclohexylcarbonitrile, azobisisobutyric acid
  • the stirring time is usually 5-10min.
  • the unsaturated carboxylic acid and the chain transfer agent can be mixed first and then added at the same time. 0.5-2h.
  • the unsaturated carboxylic acid used in the present invention is selected from one or more of acrylic acid, methacrylic acid, itaconic acid, maleic anhydride, maleic acid and fumaric acid.
  • the chain transfer agent used in the present invention is selected from sodium methacrylate sulfonate, sodium allyl sulfonate, thioglycolic acid, mercaptopropionic acid, mercaptoethanol, n-dodecyl mercaptan, sodium hypophosphite, sodium vinyl sulfonate , One or more of sodium propenyl sulfonate and sodium styrene sulfonate.
  • the temperature is lowered to about 60°C and the material is discharged, and the anhydrous solid polycarboxylic acid water reducing agent can be obtained when the product is solidified at room temperature.
  • the solid polycarboxylic acid water-reducing agent prepared by the present invention can be prepared by adding water to the solid polycarboxylic acid water-reducing agent into liquids of different concentrations or further processed into powdered solid polycarboxylic acid water-reducing agent according to different construction requirements.
  • the solid polycarboxylic acid water-reducing agent can be directly mixed into dry-mixed mortar or sprayed concrete for use. The original performance of the water-reducing agent will not be reduced during the change of the shape.
  • the solid polycarboxylic acid water-reducing agent of the present invention Due to the addition of hyperbranched monomers, the solid polycarboxylic acid water-reducing agent of the present invention has reduced requirements for viscosity during polymerization, and at the same time, its state is stable, and no adhesion occurs when stored at room temperature.
  • the solid polycarboxylic acid water-reducing agent of the present invention has excellent water-reducing and dispersing effect, and has good workability to concrete in the process of concrete evaluation. It exhibits good fluidity and retention ability, maintains excellent workability at different dosages, and shows strong adaptability to different types of cement.
  • the preparation process of the present invention can directly obtain anhydrous solid polycarboxylic acid water-reducing agent products, and does not need to be spray-dried like the traditional mother liquor water agent to obtain the powder polycarboxylic acid water-reducing agent.
  • the mother liquor of carboxylic acid water reducer is simple and has a short cycle, and is more convenient in operation.
  • the product has more obvious advantages in transportation distance and transportation cost.
  • polyether thermal materials can be used to produce solid polycarboxylic acid water reducer, the total cost can be saved. About 30%, which greatly improves the energy saving and consumption reduction of water reducing agent manufacturers.
  • the overall process of the preparation method of the present invention is green and environmentally friendly, is conducive to industrialized production and industrialized promotion and application, and has good economic benefits and social significance.
  • anhydrous solid polycarboxylic acid water reducing agent After adding initiator 2g azobisisobutyronitrile, 2.5g azobisisovaleronitrile, stirring for 10min, start to add dropwise a mixture of 36.2g methacrylic acid, 2.3g sodium hypophosphite, control the dripping reaction time in 1.5h ⁇ 5min, aging for 2.5h after the end of the reaction, pour into the tray after the end of aging, and after the product solidifies, an anhydrous solid polycarboxylic acid water reducing agent can be obtained.
  • hydroxybutyl polyoxyethylene ether (theoretical molecular weight is 2400) is put into the reactor, and the temperature is raised to 75°C. After the material is completely melted into a liquid state, 6g of the hyperbranched monomer 3 obtained in the preparation example is added and the stirring is continued for 10 minutes . After adding initiator 3.8g ammonium persulfate, stirring for 10min, start to add dropwise feeding by a mixture of 30.9g methacrylic acid and 3g sodium methacrylic acid sulfonate, control the dripping reaction time within 1h ⁇ 5min, and aging after the reaction is over 2.5h, after the aging is finished, pour it into the tray and discharge it. After the product is solidified, an anhydrous solid polycarboxylic acid water reducing agent can be obtained.
  • the comparative example is only that the hyperbranched monomer is not added under the same conditions as the example, and the molecular weight of the sample of example 1-8 and the comparative example 1-8 (without hyperbranched monomer added) are tested by gel liquid chromatography. ) The molecular weight of the sample, and the results are shown in Table 1.
  • the viscosity of the sample after adding the hyperbranched monomer is generally between 3000-3500, and the viscosity without the hyperbranched monomer is generally between 4900-5500, and the molecular weight of the solid polycarboxylic acid water-reducing agent is not large. Change; it is proved that adding hyperbranched monomers can significantly reduce the viscosity of solid polycarboxylic acid water-reducing agent.
  • the decrease in viscosity indicates that the equipment requirements of solid polycarboxylic acid water-reducing agent in the production have been reduced, and the production will be increased when the product is sliced There is improvement, and there is more room for improvement in product profit.
  • the solid polycarboxylic acid water-reducing agent prepared in Examples 1-8 is configured as a water-reducing agent with a concentration of 10%. According to the test requirements of the high-performance water-reducing agent in the GB8076-2008 "Concrete Additives" standard, the examples are synthesized The performance of the sample and the commercial water reducer (HD-14 high-performance polycarboxylic acid water reducer produced by Shenyang Haida Building Material Factory) was compared. The experimental formulation is shown in Table 2, and the concrete performance test results are shown in Tables 3 and 4. Shown.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (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)
  • Polymerisation Methods In General (AREA)

Abstract

La présente invention concerne un agent réducteur d'eau à base d'acide polycarboxylique solide et son procédé de préparation. Le procédé de préparation comprend : la fusion d'un monomère de polyol de polyéther et d'un monomère hyper-ramifié pour obtenir un liquide ; l'ajout d'un initiateur au liquide, l'agitation et puis l'ajout d'un acide carboxylique insaturé et d'un agent de transfert réversible de chaîne pour obtenir une solution mixte ; et la réalisation d'un traitement de vieillissement sur la solution mixte, et puis un refroidissement et une solidification pour obtenir l'agent réducteur d'eau à base d'acide polycarboxylique solide. Selon l'agent réducteur d'eau à base d'acide polycarboxylique solide de la présente invention, le monomère hyper-ramifié est ajouté, de sorte à réduire l'exigence de viscosité pendant la polymérisation, à améliorer la maniabilité du béton au cours du processus d'évaluation du béton, à éliminer des phénomènes tels que le ressuage, le ressuage de mortier et la fuite entre les pierres, et à pouvoir réduire la viscosité du béton en cas de faible rapport eau-ciment. De plus, selon le procédé de la présente invention, le produit de type agent réducteur d'eau à base d'acide polycarboxylique solide anhydre peut être obtenu une fois la préparation terminée. Contrairement à l'agent aqueux de solution mère classique, un agent réducteur d'eau à base d'acide polycarboxylique en poudre peut être obtenu par séchage par pulvérisation. Par comparaison avec l'agent réducteur d'eau à base d'acide polycarboxylique en poudre, l'agent réducteur d'eau à base d'acide polycarboxylique solide réduit considérablement le coût de production et le coût de transport longue distance.
PCT/CN2020/090002 2020-05-13 2020-05-13 Agent réducteur d'eau à base d'acide polycarboxylique solide et son procédé de préparation WO2021226869A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE112020007177.4T DE112020007177T5 (de) 2020-05-13 2020-05-13 Festes Polycarbonsäure-Fließmittel und Verfahren zu dessen Herstellung
PCT/CN2020/090002 WO2021226869A1 (fr) 2020-05-13 2020-05-13 Agent réducteur d'eau à base d'acide polycarboxylique solide et son procédé de préparation

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Cited By (2)

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CN114380529A (zh) * 2021-12-31 2022-04-22 河北圣通建材科技有限公司 一种抗泥型聚羧酸减水剂及其制备方法
CN117105596A (zh) * 2023-07-26 2023-11-24 中建三局集团有限公司 一种再生混凝土及其制备方法

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CN110240676A (zh) * 2019-04-10 2019-09-17 武汉理工大学 一种固体聚羧酸减水剂的制备方法

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CN108192041B (zh) 2017-12-29 2020-06-26 江苏苏博特新材料股份有限公司 一种粉末状聚羧酸减水剂的制备方法及应用

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JP2002201240A (ja) * 2000-12-27 2002-07-19 Nippon Shokubai Co Ltd ポリカルボン酸系共重合体の製造方法
WO2003024885A2 (fr) * 2001-09-19 2003-03-27 Construction Research & Technology Gmbh Agents d'amelioration de la maniabilite destines a des compositions de ciment
JP2006256887A (ja) * 2005-03-16 2006-09-28 Nof Corp セメント用添加剤
CN102741342A (zh) * 2009-09-08 2012-10-17 联合利华有限公司 支化共聚物在聚合物共混物中的用途
CN106928440A (zh) * 2015-12-29 2017-07-07 辽宁奥克化学股份有限公司 一种聚醚酰胺、由该聚醚酰胺制得的减水剂及制备方法
CN108484841A (zh) * 2018-03-30 2018-09-04 湖北工业大学 一种本体聚合的固片状聚羧酸减水剂的制备方法
CN110240676A (zh) * 2019-04-10 2019-09-17 武汉理工大学 一种固体聚羧酸减水剂的制备方法

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114380529A (zh) * 2021-12-31 2022-04-22 河北圣通建材科技有限公司 一种抗泥型聚羧酸减水剂及其制备方法
CN117105596A (zh) * 2023-07-26 2023-11-24 中建三局集团有限公司 一种再生混凝土及其制备方法
CN117105596B (zh) * 2023-07-26 2024-06-07 中建三局集团有限公司 一种再生混凝土及其制备方法

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