CN110183692A - Three-dimensional cross-linked soluble polymer microgel of one kind and preparation method thereof - Google Patents

Three-dimensional cross-linked soluble polymer microgel of one kind and preparation method thereof Download PDF

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Publication number
CN110183692A
CN110183692A CN201910494668.9A CN201910494668A CN110183692A CN 110183692 A CN110183692 A CN 110183692A CN 201910494668 A CN201910494668 A CN 201910494668A CN 110183692 A CN110183692 A CN 110183692A
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soluble polymer
dimensional cross
preparation
linked soluble
microgel
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李宝军
丁兴隆
白少勇
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SUZHOU BOTERUI NEW MATERIALS CO Ltd
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SUZHOU BOTERUI NEW MATERIALS CO Ltd
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F112/00Homopolymers 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 an aromatic carbocyclic ring
    • C08F112/34Monomers containing two or more unsaturated aliphatic radicals
    • C08F112/36Divinylbenzene
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F120/00Homopolymers 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
    • C08F120/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/10Esters
    • C08F120/12Esters of monohydric alcohols or phenols
    • C08F120/14Methyl esters, e.g. methyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/14Methyl esters, e.g. methyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/16Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/02Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/075Macromolecular gels
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/24Crosslinking, e.g. vulcanising, of macromolecules
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/16Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2325/00Characterised by the use of homopolymers or 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 an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/02Homopolymers or copolymers of hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00Characterised by the use 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; Derivatives of such polymers
    • C08J2333/04Characterised by the use 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; Derivatives of such polymers esters
    • C08J2333/06Characterised by the use 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; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2333/10Homopolymers or copolymers of methacrylic acid esters
    • C08J2333/12Homopolymers or copolymers of methyl methacrylate

Abstract

The present invention relates to a kind of three-dimensional cross-linked soluble polymer microgels and preparation method thereof, monomer containing vinyl, anhydrous metal halide catalyst are added in solvent mix together, it is placed in reaction kettle and seals, higher than solvent boiling point and under 80-95 DEG C of bath temperature, reaction 2-48 hours, after the reaction was completed, products therefrom is washed, centrifugation, it is dry after, obtain three-dimensional cross-linked soluble polymer microgel, wherein, the weight ratio of the catalyst and the monomer containing vinyl is (2-100): 100;The volume ratio of the monomer containing vinyl and solvent is (0.5-10): 100.Three-dimensional cross-linked soluble polymer microgel of one kind of the invention and preparation method thereof, preparation process is simple, and reaction condition is safe and reliable, it is swift in response, the yield of microgel is up to 75%, is much higher than free radical solution polymerization method microgel yield obtained, is easy to industrialized production.

Description

Three-dimensional cross-linked soluble polymer microgel of one kind and preparation method thereof
Technical field
The present invention relates to technical field of polymer materials, more particularly to a kind of three-dimensional cross-linked soluble polymer microgel And preparation method thereof.
Background technique
Microgel (microgel) is a kind of three-dimensional cross-linked soluble polymer material.Microgel had both had three-dimensional cross-linked Structure, under certain condition, have preferable physics and chemical stability, while " can also dissolve " in certain solvent In, it is easy to process at various devices, in favor of heavy industrialization manufacture.Therefore, microgel is widely used in coating, absorption The various fields such as agent, catalyst carrier and senser element.In recent years, the requirement of solar cell silk screen printing is continuously improved, and is The transfer efficiency of solar battery is improved, filament printing needs constantly to reduce the sintered width of thin grid, it is necessary to improve The ink excessively of silver paste of solar cells, the addition of microgel can greatly improve the ink excessively of silver paste.
Currently, the preparation method of microgel mainly includes emulsion polymerization and polymerisation in solution.Emulsion polymerization needs a large amount of table Face activating agent stablizes the size of drop in polymerization process, and after completion of polymerization, these surfactants are generally difficult to remove, and have The performance of product may be influenced.Solution polymerization system is relatively simple, generally contains only monomer, solvent and initiator, because This products therefrom is more pure.However, in the polymerization of free radical weak solution, since monomer conversion is lower, the yield of microgel Usually lower (being lower than 30%), constrain the large-scale production of microgel.
Summary of the invention
The present invention provides a kind of three-dimensional cross-linked soluble polymer microgels and preparation method thereof, and preparation process is simple, Reaction condition is safe and reliable, is swift in response, and the yield of microgel is up to 75%, is obtained much higher than free radical solution polymerization method Microgel yield, be easy to industrialized production.
The present invention provides a kind of preparation methods of three-dimensional cross-linked soluble polymer microgel, specifically according to the following steps It carries out: the monomer containing vinyl, anhydrous metal halide catalyst being added in solvent mix together, reaction kettle is placed in Middle sealing reacts 2-48 hours, after the reaction was completed, products therefrom higher than solvent boiling point and under 80-95 DEG C of bath temperature Washed, centrifugation, it is dry after to get to particle diameter distribution 50-300nm three-dimensional cross-linked soluble polymer microgel, Wherein, the weight ratio of the catalyst and the monomer containing vinyl is (2-100): 100;The monomer containing vinyl with The volume ratio of solvent is (0.5-10): 100.
Preferably, the monomer containing vinyl includes but is not limited to divinylbenzene, ethyl acrylate, acrylic acid first Ester, methyl methacrylate, n-BMA, Isobutyl methacrylate, benzyl methacrylate, styrene and 2- The composition of one of (2- oxygen -1- imidazolidinyl) ethylmethyl acrylate or in which several arbitrary proportions.
Preferably, the anhydrous metal halide catalyst includes but is not limited to anhydrous ferric chloride, silver bromide, calcirm-fluoride.
Preferably, the solvent includes but is not limited to dichloroethanes, acetonitrile, isopropanol, tetrahydrofuran.
Preferably, the reaction time is 4-6 hours.
Preferably, the volume ratio of the monomer containing vinyl and solvent is (0.8-1.5): 100.
Preferably, the weight ratio of the catalyst and the monomer containing vinyl is (5-20): 100.
The present invention also provides a kind of three-dimensional cross-linked soluble polymer microgels, by any of the above-described preparation method It is made.
Advantages of the present invention: three-dimensional cross-linked soluble polymer microgel of one kind of the invention and preparation method thereof, preparation Process is simple, and reaction condition is safe and reliable, is swift in response, and the yield of microgel is up to 75%, is much higher than free radical solution polymerization Method microgel yield obtained, is easy to industrialized production.
Specific embodiment
In order to deepen the understanding of the present invention, below in conjunction with embodiment, the invention will be described in further detail, the reality It applies example for explaining only the invention, protection scope of the present invention is not constituted and limited.
Embodiment one
Present embodiments provide a kind of three-dimensional cross-linked soluble polymer microgel, by 3mL divinylbenzene monomers, 0.15g anhydrous ferric trichloride, 300mL tetrahydrofuran are prepared.
Preparation method: by 3mL divinylbenzene monomers, 0.15g anhydrous ferric trichloride, 300mL tetrahydrofuran in ice-water bath Under conditions of it is miscible, be then added into the polytetrafluoroethyllining lining of stainless steel cauldron, seal;It is subsequently placed in water-bath, water Bath temperature is set as 88 DEG C, reacts 6 hours, after the reaction was completed, wash with isopropanol, centrifugation, it is dry after to get arriving partial size It is distributed in the three-dimensional cross-linked soluble polydivinylbenezene microgel of 50-300nm, yield 75% dissolves in conventional organic Solvent.
Embodiment two
Present embodiments provide a kind of three-dimensional cross-linked soluble polymer microgel, by 3mL methyl methacrylate monomer, 0.6g silver bromide, 300mL acetonitrile are prepared.
Preparation method: by 3mL methyl methacrylate monomer, 0.6g silver bromide, 300mL acetonitrile under conditions of ice-water bath It is miscible, it is then added into the polytetrafluoroethyllining lining of stainless steel cauldron, seals;It is subsequently placed in water-bath, bath temperature is set Be set to 90 DEG C, react 5 hours, after the reaction was completed, with ethanol washing, centrifugation, it is dry after to get to particle diameter distribution in 50- The three-dimensional cross-linked soluble polymethyl methacrylate microgel of 300nm, yield 73% dissolve in conventional organic solvent.
Embodiment two
Present embodiments provide a kind of three-dimensional cross-linked soluble polymer microgel, by 3mL methyl methacrylate monomer, 0.6g silver bromide, 300mL acetonitrile are prepared.
Preparation method: by 1.5mL methyl methacrylate monomer, 1.5mL n-BMA monomer, 0.55g chlorine It is miscible under conditions of ice-water bath to change silver, 300mL acetonitrile, is then added into the polytetrafluoroethyllining lining of stainless steel cauldron, Sealing;It is subsequently placed in water-bath, bath temperature is set as 90 DEG C, reacts 4 hours, after the reaction was completed, is washed, is centrifuged with isopropanol Precipitating, it is dry after to get to particle diameter distribution 50-300nm three-dimensional cross-linked soluble methyl methacrylate and metering system Sour N-butyl copolymer microgel, yield 71% dissolve in conventional organic solvent.
Polymer microgel of above embodiments and preparation method thereof, preparation process is simple, and reaction condition is safe and reliable, instead Should rapidly, the yield of microgel may be up to 75%, is much higher than free radical solution polymerization method microgel yield obtained, is easy to Industrialized production.
Above-described embodiment should not in any way limit the present invention, all to be obtained by the way of equivalent replacement or equivalency transform Technical solution fall within the scope of protection of the present invention.

Claims (8)

1. a kind of preparation method of three-dimensional cross-linked soluble polymer microgel, it is characterised in that: be specifically according to the following steps into Capable: the monomer containing vinyl, anhydrous metal halide catalyst are added in solvent mix together, is placed in reaction kettle 2-48 hours, after the reaction was completed, products therefrom warp higher than solvent boiling point and under 80-95 DEG C of bath temperature, are being reacted in sealing Washing, centrifugation, it is dry after to get to particle diameter distribution 50-300nm three-dimensional cross-linked soluble polymer microgel, In, the weight ratio of the catalyst and the monomer containing vinyl is (2-100): 100;The monomer containing vinyl with it is molten The volume ratio of agent is (0.5-10): 100.
2. the preparation method of the three-dimensional cross-linked soluble polymer microgel of one kind according to claim 1, it is characterised in that: The monomer containing vinyl includes but is not limited to divinylbenzene, ethyl acrylate, methyl acrylate, methyl methacrylate Ester, n-BMA, Isobutyl methacrylate, benzyl methacrylate, styrene and 2- (2- oxygen -1- imidazolidine Base) one of ethylmethyl acrylate or in which several arbitrary proportions composition.
3. the preparation method of the three-dimensional cross-linked soluble polymer microgel of one kind according to claim 1, it is characterised in that: The anhydrous metal halide catalyst includes but is not limited to anhydrous ferric chloride, silver bromide, calcirm-fluoride.
4. the preparation method of the three-dimensional cross-linked soluble polymer microgel of one kind according to claim 1, it is characterised in that: The solvent includes but is not limited to dichloroethanes, acetonitrile, isopropanol, tetrahydrofuran.
5. the preparation method of the three-dimensional cross-linked soluble polymer microgel of one kind according to claim 1, it is characterised in that: The reaction time is 4-6 hours.
6. the preparation method of the three-dimensional cross-linked soluble polymer microgel of one kind according to claim 1, it is characterised in that: The volume ratio of the monomer containing vinyl and solvent is (0.8-1.5): 100.
7. the preparation method of the three-dimensional cross-linked soluble polymer microgel of one kind according to claim 1, it is characterised in that: The weight ratio of the catalyst and the monomer containing vinyl is (5-20): 100.
8. a kind of three-dimensional cross-linked soluble polymer microgel, it is characterised in that: by system of any of claims 1-7 Preparation Method is made.
CN201910494668.9A 2019-06-10 2019-06-10 Three-dimensional cross-linked soluble polymer microgel of one kind and preparation method thereof Pending CN110183692A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110964593A (en) * 2019-12-18 2020-04-07 中国科学院兰州化学物理研究所 Polymerization-induced self-assembly oleogel and preparation method and application thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2246135A1 (en) * 2004-04-02 2006-02-01 Universidad Complutense De Madrid Set of microgel particles containing immobilised glucose oxidase consists of a glucose amperometric biosensor with a silver chloride reference electrode
CN107635655A (en) * 2015-01-06 2018-01-26 Lvmh研究公司 PEG methacrylate microgel, preparation method and purposes
CN108976334A (en) * 2018-06-22 2018-12-11 济南大学 Three-dimensional cross-linked soluble polydivinylbenezene microgel of one kind and preparation method thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2246135A1 (en) * 2004-04-02 2006-02-01 Universidad Complutense De Madrid Set of microgel particles containing immobilised glucose oxidase consists of a glucose amperometric biosensor with a silver chloride reference electrode
CN107635655A (en) * 2015-01-06 2018-01-26 Lvmh研究公司 PEG methacrylate microgel, preparation method and purposes
CN108976334A (en) * 2018-06-22 2018-12-11 济南大学 Three-dimensional cross-linked soluble polydivinylbenezene microgel of one kind and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110964593A (en) * 2019-12-18 2020-04-07 中国科学院兰州化学物理研究所 Polymerization-induced self-assembly oleogel and preparation method and application thereof
CN110964593B (en) * 2019-12-18 2021-06-01 中国科学院兰州化学物理研究所 Polymerization-induced self-assembly oleogel and preparation method and application thereof

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