CN108276833A - A kind of ternary block polymer aqueous dispersion of RAFT synthesis - Google Patents
A kind of ternary block polymer aqueous dispersion of RAFT synthesis Download PDFInfo
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- CN108276833A CN108276833A CN201711399309.2A CN201711399309A CN108276833A CN 108276833 A CN108276833 A CN 108276833A CN 201711399309 A CN201711399309 A CN 201711399309A CN 108276833 A CN108276833 A CN 108276833A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
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- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
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- 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
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/02—Acids; Metal salts or ammonium salts thereof, e.g. maleic acid or itaconic acid
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- 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
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- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
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- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Graft Or Block Polymers (AREA)
- Paints Or Removers (AREA)
Abstract
The present invention relates to a kind of ternary block polymer aqueous dispersions of RAFT synthesis, and by itaconic acid, vinylbenzenesulfonic acid sodium, methacryloxypropyl alkylol phosphate monoester, RAFT agent, azo-initiator are synthesized by RAFT technologies；Its number-average molecular weight is 3000~8000, polydispersity coefficient PDI≤1.2；The ternary block polymer aqueous dispersion of the present invention, its anchoring group carboxylate ion, sulfonate ion, phosphate ester salt ion multiple spot is adsorbed on particle surface and forms electric double layer electrostatic repulsion, and vinylbenzenesulfonic acid base, the pectination distribution of methacryl oxyalkyl, which generates steric hindrance, mutually to be wound, and it extends in dispersion, due to the double action of electrostatic repulsion and steric hindrance, not only dispersion efficiency is high, viscosity reduction is good, and form stable suspension system, it can be used for aqueous color paste, water nano mill base, aqueous UV/LED mill bases, the dispersion of water-based industrial paint mill base.
Description
Technical field
The present invention relates to aqueous point of the ternary block polymers that a kind of aqueous dispersion more particularly to a kind of RAFT are synthesized
Powder belongs to dispersant technical field.
Background technology
In the chemical industries such as coating, ink, cement, ceramics, the dispersion of pigment, filler is the important ring of manufacturing technology
Section.In order to make organic and inorganic pigment, filler in related system obtain stable homogeneous dispersion, dispersant is commonly used.Although passing
The dispersant of system shows effective stably dispersing effect in aqueous dispersion medium, but since they are on pigment particles surface
Absorption very securely, is not easy the desorption from particle surface and reassembles or precipitate so as to cause scattered particle, system
Long-time stability are not good enough, adversely affected to paint film appearance, hardness and the properties such as ageing-resistant yet.To overcome the office of traditional dispersant
It is sex-limited, it develops in recent years and applies macromolecule dispersing agent.Macromolecule dispersing agent is dispersed with remarkable result to pigment, filler,
Especially there is sizable effect to wetability, stability etc., also have larger improvement to the application performance of pigment, it has also become is new
The dispersant with high efficiency of a generation.
Chinese patent CN101117450A discloses a kind of non-ionic hyperbranched macromolecular dispersant for organic pigment
Preparation method mainly takes hydrophobicity dissaving polymer, coupler and hydrophily chain to be dissolved in solvent respectively, through fully molten
Solution is uniformly mixed and solution is made；Coupler solvent solution is placed in reaction vessel, is heated up under stiring, hydrophily chain is added
Solvent solution is placed in above-mentioned reaction vessel, agitated, insulation reaction, adds hydrophobicity dissaving polymer solvent solution,
Under stiring heating, insulation reaction, then through cooling, be filtered, washed, be dried in vacuo for non-ionic hyperbranched macromolecular disperse
Agent.The invention can obtain solid content height, good fluidity, stability height, brightly painted nanoscale organic pigment；Technological process letter
Single, reaction can carry out at a lower temperature, purification of products is convenient, be not in gel and automatically speed up phenomenon；But due to non-
The anchoring group of ionic dispersant is anchored for the relatively weak hydrogen bond of binding force and due to being synthesized using traditional polymerization,
The invention synthetic dispersing agent dispersion efficiency is slightly lower.
Chinese patent CN101845122A discloses a kind of water-based polymer pigment dispersant and leather prepared therefrom sun
Ion pigment paste has developed one kind using esters of acrylic acid, acrylate derivative and functional unsaturated monomer synthesis
Novel aqueous cationic polymer dispersant has prepared the leather Series of Water with same dispersion using the dispersant
Property ultra-fine cationic pigment paste, average grain diameter reaches 0.3-1.0 microns, when being used for leather finish, can obtain soft feel
It is bright-colored with good covering power.Wherein, the macromolecule dispersing agent has the weight average molecular weight of about 5000-50000, tool
There is cationic characteristic, is suitable for the dispersion of the common all kinds of pigment of leather industry, but since dispersant is cationic, limit
Its application in other field.
Chinese patent CN104086762A disclose a kind of Hyperbranched Polyester Resin pigment dispersing agent, preparation method and its
The application of pigment dispersion color paste and mill base；The present invention Hyperbranched Polyester Resin pigment dispersing agent be with hydroxy functional group,
Dendritic, hyperbranched, 3D structures polyester, number-average molecular weight are 1500~20000, and solid content is 20%~90%,
It is to be reacted using acid anhydrides and hyper-branched polyester, is then the chemical combination that mono-epoxy-functional's other end is hydrophobicity Long carbon chain with one end
It is prepared by object reaction；Chain alkyl/aryl that dispersant introduces has well like the structure of grasp with coating matrix resin strand
Compatibility, and can reduce dispersion flocculation once again or aggregation possibility.Using the paint or color of the dispersant of the invention
Slurry grinding very short time can reach fineness requirement, use it for finished product paint, hardness height, thermmal storage and the room temperature storage of finished product paint
Stability is good, can effectively slow down finished product paint precipitation and loose colour；But since the dispersant uses esterification process, the invention synthetic dispersing agent
The polydispersity coefficient of molecular weight is higher, causes its dispersion performance unstable.
Invention content
The present invention is intended to provide a kind of ternary block polymer aqueous dispersion and preparation method thereof of RAFT synthesis.
RAFT is the abbreviation of reversible addion-fragmentation chain transfer polymerization, is one kind of activity/controllable free-radical polymerisation (CRP),
Using RAFT control technologies synthesize high molecular polymer have the characteristics that molecular weight controllably, narrow molecular weight distribution.
The ternary block polymer aqueous dispersion, molecular structural formula are as follows：
Wherein, n=5~20 in molecular formula, p=4~10, m=4~10；The anchoring group be carboxylate anion,
Sulfonate anionic, phosphate ester salt anion.
The ternary block polymer aqueous dispersion, number-average molecular weight are 3000~8000, polydispersity coefficient PDI
≤1.2。
Ternary block polymer aqueous dispersion of the present invention, by itaconic acid, vinylbenzenesulfonic acid sodium, metering system
Acyloxyalkyl group alcohol phosphate monoester, the ternary block polymer dispersant synthesized using RAFT reagents, RAFT technology synthetic reactions
Formula is as follows：
A kind of ternary block polymer aqueous dispersion of RAFT synthesis of the present invention, preparation process are as follows：
By weight, successively by 10.0~30.0 parts of itaconic acids, 5.0~15.0 parts of sodium p styrene sulfonates, 10.0~
20.0 parts of methacryloxypropyl alkylol phosphates, 1.0~3.0 parts of RAFT agent, 40.0~80.0 parts of solvents are added
Into reaction kettle, lead to N2Protection is warming up to 50~100 DEG C, then drops evenly 8.0~15.0 after unlatching stirring and dissolving is uniform
The solvent solution for part containing 10% initiator, drips off in 0.5h, is maintained at 50~100 DEG C the reaction was continued 6~8h；Then slowly add
Enter aqueous slkali and deionized water, it is 7~8 to be adjusted to pH, obtains the ternary block polymer aqueous dispersion.
Wherein, the methacryloxypropyl alkylol phosphate is methylacryoyloxyethyl alcohol phosplate, methyl
Acryloxypropyl alcohol phosplate, methacryloxypropyl butyl alcohol phosplate, methacryloxypropyl amyl alcohol phosplate,
At least one of methacryloxypropyl hexyl alcohol phosplate, methacryloxypropyl heptyl alcohol phosplate.
The initiator is azodiisobutyronitrile, azobisisoheptonitrile, azo-bis-iso-dimethyl, two isobutyl of azo
At least one of base amidine hydrochloride.
The RAFT agent is anionic or cationic modified water-soluble dithioesters, water-soluble trithio
Ester；Further, it is preferable to be 4,4 '-two thio phenylacetic acids, α-two thio phenyls carbomethoxy to benzylidene pyridinium chloride salt, S,
Bis- (α, the α '-dimethyl-α "-acetic acid) trithiocarbonates of S '-, isopropyl xanthogen disulfide, diethyl-dithio ammonia
At least one of carbamate type quaternary ammonium salt.
The solvent is water, methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, isobutanol, propylene glycol monomethyl ether, the third two
At least one of alcohol butyl ether, butyl.
The aqueous slkali is at least one of sodium hydroxide, potassium hydroxide, ammonium hydroxide.
A kind of ternary block polymer aqueous dispersion of RAFT synthesis of the present invention, anchoring group carboxylate ion,
Sulfonate ion, phosphate ester salt ion multiple spot be adsorbed on particle surface formed electric double layer electrostatic repulsion, and vinylbenzenesulfonic acid base,
The pectination distribution of methacryl oxyalkyl, which generates steric hindrance, mutually to be wound, and extends in dispersion, due to quiet
Electricity repels and the double action of steric hindrance, and not only dispersion efficiency is high, and compatibility is good, and forms stable suspension system；This
The ternary block polymer aqueous dispersion of invention using RAFT synthetic method molecular weight medium (3000~8000), narrowly distributing and
It is even, and contain more anchoring groups, dispersion efficiency is high, and viscosity reduction is good.It can be used for aqueous color paste, water nano mill base, aqueous UV/LED
The dispersion of mill base, water-based industrial paint mill base.
Specific implementation mode
A kind of ternary block polymer aqueous dispersion of RAFT synthesis of the present invention is done into one with reference to embodiment
The description of step.It is understood that specific embodiment described herein is used only for explaining related invention, rather than to the invention
Restriction.
Embodiment 1
A kind of ternary block polymer aqueous dispersion of RAFT synthesis, preparation process are as follows：
By weight, successively by 25.0 parts of itaconic acids, 12.0 parts of sodium p styrene sulfonates, 19.0 parts of methacryloxypropyls
Butyl alcohol phosplate, 1.6 parts of S, bis- (α, the α '-dimethyl-α "-acetic acid) trithiocarbonates of S '-, 80.0 parts of ethyl alcohol are added
Into reaction kettle, lead to N2Protection is warming up to 75 DEG C after unlatching stirring and dissolving is uniform, drops evenly 10.0 parts and contains 10% azo two
The ethanol solution of isobutyronitrile, drips off in 0.5h, is maintained at 75 DEG C the reaction was continued 6h；Be then slowly added into 10%NaOH solution and
Deionized water, it is 7~8 to be adjusted to pH, obtains the ternary block polymer aqueous dispersion.
Embodiment 2
A kind of ternary block polymer aqueous dispersion of RAFT synthesis, preparation process are as follows：
By weight, successively by 22.0 parts of itaconic acids, 13.0 parts of sodium p styrene sulfonates, 15.0 parts of methacryloxypropyls
Ethyl alcohol phosplate, the 4 of 3.0 parts, 4 '-two thio phenylacetic acids, 70.0 parts of isopropanols are added in reaction kettle, lead to N2Protection,
After unlatching stirring and dissolving is uniform, 70 DEG C are warming up to, drops evenly 8.0 parts of isopropanols for containing 10% azo diisobutyl amidine hydrochloride
Solution drips off in 0.5h, is maintained at 70 DEG C the reaction was continued 6h；It is then slowly added into 10%NaOH solution and deionized water, is adjusted
It is 7~8 to pH, obtains the ternary block polymer aqueous dispersion.
Embodiment 3
A kind of ternary block polymer aqueous dispersion of RAFT synthesis, preparation process are as follows：
By weight, successively by 16.0 parts of itaconic acids, 10.0 parts of sodium p styrene sulfonates, 12.0 parts of methacryloxypropyls
Alkyl propanols phosplate, 2.0 parts of diethyldithiocarbamate type quaternary ammonium salt, 60.0 parts of water are added to reaction kettle
In, lead to N2Protection is warming up to 85 DEG C after unlatching stirring and dissolving is uniform, drops evenly 12.0 parts and contains 10% azodiisobutyronitrile
Aqueous solution drips off in 0.5h, is maintained at 85 DEG C the reaction was continued 6h；It is then slowly added into 10%NaOH solution and deionized water,
It is 7~8 to be adjusted to pH, obtains the ternary block polymer aqueous dispersion.
Dispersant technical indicator described in the embodiment of the present invention is as shown in table 1：
1 ternary block polymer aqueous dispersion technical indicator of table
| Project | Embodiment 1 | Embodiment 2 | Embodiment 3 |
| Appearance | Weak yellow liquid | Weak yellow liquid | Weak yellow liquid |
| Solid content, % | 41.6 | 42.3 | 40.5 |
| pH | 7~8 | 7~8 | 7~8 |
| Number-average molecular weight, Mn | 4000~4300 | 3700~4000 | 7200~7500 |
| Polydispersity coefficient, Mw/Mn | 1.17 | 1.16 | 1.2 |
Although the present invention has been explained in detail and has referred to embodiment, for those of ordinary skill in the art, show
Various schemes, modification and the change that can so make as specified above, should be construed as being included within the scope of the claims.
Claims (6)
1. a kind of ternary block polymer aqueous dispersion of RAFT synthesis, it is characterised in that：The ternary block polymer
Aqueous dispersion, molecular structural formula are as follows：
Wherein, n=5~20 in molecular formula, p=4~10, m=4~10；The anchoring group is carboxylate anion, sulfonic acid
Salt anionic, phosphate ester salt anion；The ternary block polymer aqueous dispersion, number-average molecular weight be 3000~
8000, polydispersity coefficient PDI≤1.2；
The ternary block polymer aqueous dispersion, preparation process are as follows：
By weight, successively by 10.0~30.0 parts of itaconic acids, 5.0~15.0 parts of sodium p styrene sulfonates, 10.0~20.0
Part methacryloxypropyl alkylol phosphate, 1.0~3.0 parts of RAFT agent, 40.0~80.0 parts of solvents are added to instead
It answers in kettle, leads to N2Protection is warming up to 50~100 DEG C, then drops evenly 8.0~15.0 parts and contain after unlatching stirring and dissolving is uniform
The solvent solution of 10% initiator, drips off in 0.5h, is maintained at 50~100 DEG C the reaction was continued 6~8h；It is then slowly added into alkali
Solution and deionized water, it is 7~8 to be adjusted to pH, obtains the ternary block polymer aqueous dispersion.
2. the ternary block polymer aqueous dispersion of RAFT synthesis according to claim 1, it is characterised in that：Described
Methacryloxypropyl alkylol phosphate is methylacryoyloxyethyl alcohol phosplate, methacryloxypropyl alcohol monophosphate
Ester, methacryloxypropyl butyl alcohol phosplate, methacryloxypropyl amyl alcohol phosplate, methacryloxypropyl hexyl alcohol list
At least one of phosphate, methacryloxypropyl heptyl alcohol phosplate.
3. the ternary block polymer aqueous dispersion of RAFT synthesis according to claim 1, it is characterised in that：Described
Initiator is in azodiisobutyronitrile, azobisisoheptonitrile, azo-bis-iso-dimethyl, azo diisobutyl amidine hydrochloride
It is at least one.
4. the ternary block polymer aqueous dispersion of RAFT synthesis according to claim 1, it is characterised in that：Described
RAFT agent is 4,4 '-two thio phenylacetic acids, α-two thio phenyls carbomethoxy to benzylidene pyridinium chloride salt, S, and S '-is bis-
(α, α '-dimethyl-α "-acetic acid) trithiocarbonate, isopropyl xanthogen disulfide, diethyldithiocar bamic acid
At least one of ester type quaternary ammonium salt.
5. the ternary block polymer aqueous dispersion of RAFT synthesis according to claim 1, it is characterised in that：Described
Solvent is water, methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, isobutanol, propylene glycol monomethyl ether, propandiol butyl ether, diethylene glycol
At least one of butyl ether.
6. the ternary block polymer aqueous dispersion of RAFT synthesis according to claim 1, it is characterised in that：Described
Aqueous slkali is at least one of sodium hydroxide, potassium hydroxide, ammonium hydroxide.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113773693A (en) * | 2021-09-14 | 2021-12-10 | 扬州工业职业技术学院 | Wetting dispersant and application thereof |
| CN115286967A (en) * | 2022-07-07 | 2022-11-04 | 江苏景宏新材料科技有限公司 | Water-based acrylate adhesive, water-based matte gloss oil and preparation method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113773693A (en) * | 2021-09-14 | 2021-12-10 | 扬州工业职业技术学院 | Wetting dispersant and application thereof |
| CN115286967A (en) * | 2022-07-07 | 2022-11-04 | 江苏景宏新材料科技有限公司 | Water-based acrylate adhesive, water-based matte gloss oil and preparation method thereof |
| CN115286967B (en) * | 2022-07-07 | 2023-11-21 | 江苏景宏新材料科技有限公司 | Water-based acrylate binder, water-based matte gloss oil and preparation method thereof |
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Application publication date: 20180713 |