CN107649069B - A kind of phosphate type ternary block polymer dispersing agent and preparation method thereof - Google Patents
A kind of phosphate type ternary block polymer dispersing agent and preparation method thereof Download PDFInfo
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- CN107649069B CN107649069B CN201710866401.9A CN201710866401A CN107649069B CN 107649069 B CN107649069 B CN 107649069B CN 201710866401 A CN201710866401 A CN 201710866401A CN 107649069 B CN107649069 B CN 107649069B
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
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- 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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- C08F2438/00—Living radical polymerisation
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Abstract
The present invention relates to a kind of phosphate type ternary block polymer dispersing agents and preparation method thereof, the dispersing agent is and steric group number-average molecular weight 4000~10000 using phosphate radical and carboxylate radical as anchoring group, with pyrrole network alkanone base, molecular weight polydispersity coefficient is less than 1.3, the structure such as following figure；Advantages of the present invention are as follows: when phosphate anion, carboxylate anion are anchoring group, polyvinylpyrrolidone unit performance steric effect, dispersion is more stable；Using ATRP synthetic method, the dispersant molecule amount is low, even molecular weight distribution, therefore dispersing agent dispersion efficiency of the present invention is high, can be widely applied to the dispersion of pigment, powder, glaze.
Description
Technical field
The present invention relates to a kind of preparation methods of dispersing agent, and in particular to a kind of phosphate type ternary block polymer point
Powder and preparation method thereof belongs to macromolecule dispersing agent technical field.
Background technique
In the chemical industries such as coating, ink, cement, ceramic glaze, the dispersion of pigment, filler is the important of manufacturing technology
Link.In order to make organic and inorganic pigment, filler in related system obtain stable homogeneous dispersion, dispersing agent is commonly used.Although
Traditional dispersing agent shows effective stably dispersing effect in aqueous dispersion medium, but since they are on pigment particles surface
Absorption not very securely, be easy from particle surface desorption reassemble or precipitate so as to cause scattered particle, system
Long-time stability it is not good enough, paint film appearance, hardness and the properties such as ageing-resistant are also adversely affected.To overcome traditional dispersing agent
Limitation is developed in recent years and applies macromolecule dispersing agent.Macromolecule dispersing agent is dispersed with significant effect to pigment, filler
Fruit especially has sizable effect to wetability, stability etc., also has larger improvement to the application performance of pigment, has become
For the dispersant with high efficiency of a new generation.
Atom transfer radical polymerization (Atom Transfer Radical Polymerization, ATRP) is with simple
Organohalogen compounds be initiator, transient metal complex is halogen atom carrier, by redox reaction, reactive species with stop
Reversible dynamic equilibrium is established between kind of sleeping, to realize the control to polymerization reaction.Exist about ATRP polymerization at present
The related application report in macromolecule dispersing agent field, but it is considerably less.
Chinese patent CN102040711A discloses a kind of amphiphilic polymer pigment wetting dispersion for water paint
Agent and preparation method, the invention polymer are solid wetting dispersing agent；The invention can substantially reduce cost, improve efficiency, and
Greatly improve the performance of product.But the monomer as used in the invention is macromonomer, the dispersing agent for causing the invention to prepare point
Son amount is larger, and the application range of dispersing agent is restricted.
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 Hyperbranched Polyester Resin pigment dispersing agent of the invention be with hydroxy functional group,
Dendritic, hyperbranched, 3D structure polyester is to be reacted using acid anhydrides and hyper-branched polyester, is then monocycle oxygen with one end
Functional group's other end is the compound reaction preparation of hydrophobicity Long carbon chain；Chain alkyl/aryl that dispersing agent introduces is like grasp
Structure, have good compatibility with coating matrix resin strand, and can reduce dispersion flocculation once again or aggregation can
It can property.Fineness requirement can reach using paint or mill base the grinding very short time of the dispersing agent of the invention, be used for finished product
Paint, the hardness of finished product paint is high, thermmal storage and room temperature storage stability are good, can effectively slow down finished product paint precipitating and loose colour；But due to
The dispersing agent uses esterification process, and the invention synthetic dispersing agent molecular weight is higher, polydispersity coefficient is bigger than normal, leads to its dispersion performance not
Stablize.
Summary of the invention
In order to overcome the shortcomings of the prior art and insufficient, the present invention provides a kind of dispersions of phosphate type ternary block polymer
Agent and preparation method thereof.
A kind of phosphate type ternary block polymer dispersing agent of the present invention, structural schematic diagram is as follows, the dispersion
Agent is using phosphate radical and carboxylate radical as anchoring group, using pyrrole network alkanone base as steric group, number-average molecular weight 4000~10000,
Molecular weight polydispersity coefficient is less than 1.3.
A kind of phosphate type ternary block polymer dispersing agent of the present invention, is synthesized, preparation step using ATRP method
It is as follows:
(a) in the reaction unit of logical nitrogen, successively by 0.2~1.0 part of ligand, 0.5~1.5 part of catalyst, 0.05
~0.1 part of surfactant, 50~80 parts of water, 30 parts of methacryloxypropyl alkylol mono phosphoric acid ester esters monomers are added to reaction dress
In setting, stirring and emulsifying simultaneously heat up 70~90 DEG C, by Dropping feeder be added dropwise 5~10 parts of 10% part of initiators aqueous solution, 0.5~
1h is added dropwise, and then 70~90 DEG C of reaction 1h~2h, obtain solution a；
(b) 5~10 parts of fumaric acid are taken, sodium hydroxide solution is added and is neutralized to pH=7,5~10 parts of water dilutions are then added,
Obtain fumaric acid sodium aqueous solution；Fumaric acid sodium aqueous solution is added dropwise dropwise into above-mentioned solution a, 0.5~1h is added dropwise, and 70~90 DEG C
Lower the reaction was continued 1h~2h, obtains solution b；
(c) 10~15 parts of vinylpyridine network alkanones are dissolved in 20~30 parts of water, obtain vinylpyridine network alkanone solution；To
Vinylpyridine network alkanone solution is added dropwise in above-mentioned solution b dropwise, 0.5~1h is added dropwise, and then continues at 70~90 DEG C anti-
1h~2h is answered, natural cooling is added after sodium hydroxide solution is neutralized to pH-=7 and stops stirring, phosphoric acid of the present invention is made
Precipitating reagent precipitating, dry, washing, re-dry are added into copolymer dispersant solution for salt form block copolymer dispersant solution
Up to a kind of phosphate type block copolymer dispersant of the present invention after granulation.
The ligand is N, N, N ', N '-tetramethylethylenediamine, N, N, N ', N ', N "-pentamethyl methyl acrylate base two
Vinyl triamine, N, N, N ', N ', N ", N "-hexamethyl n-butyl acrylate base triethylene tetraamine, 2,2 '-bipyridyls, N, N,
N ', N ', N "-pentamethyldivinyltriamine, N, N, N ', N ', N ", in N "-hexamethyl methyl acrylate base triethylene tetraamine
At least one.
The catalyst is at least one of cuprous bromide, stannous chloride, cuprous bromide, copper bromide.
The surfactant is double dodecylphenyl ether sodium disulfonates, odium stearate, sodium laurate, OP-10, benzene
Ethyl phenol polyethenoxy ether, tween, fatty alcohol polyethenoxy ether class, octadecyldimethyl vinyl phenyl ammonium chloride, dodecane
At least one of base dimethylvinylsiloxy Phenyl chloride.
The methacryloxypropyl alkylol mono phosphoric acid ester esters monomer is methylacryoyloxyethyl alcohol phosplate, first
Base acryloxypropyl alcohol phosplate, methacryloxypropyl butyl alcohol phosplate, methacryloxypropyl amyl alcohol monophosphate
At least one of ester, methacryloxypropyl hexyl alcohol phosplate, methacryloxypropyl heptyl alcohol phosplate.
The initiator is 4- [2- (the bromo- 2- methylpropionyloxy of 2-) ethyoxyl] -4- oxo -2- sulfonic group butyric acid two
Sodium, 4- [10- (the bromo- 2- methylpropionyloxy of 2-) decyloxy] -4- oxo -2- sulfonic group butyric acid disodium, 4- [6- (the bromo- 2- first of 2-
Base propionyloxy) hexyloxy] -4- oxo -2- sulfonic group butyric acid disodium, 4- [10- (the bromo- 2- methylpropionyloxy of 2-) pungent oxygen
Base] -4- oxo -2- sulfonic group butyric acid disodium, 2- chlorine propionamide, 2- bromine propionamide, 2- iodo methyl acrylate, 2- chloro third
Nitrile, 2- bromopropene acetoacetic ester, 2- bromopropene acid methyl esters, propylene bromide acetoacetic ester, 1- bromoacetonitrile, 2- methyl -2- bromo propylene
Acetoacetic ester, 2- isobutyl ethyl bromide, 2- bromopropene acetoacetic ester, N, at least one of N- diethyl -2- bromo acrylamide.
A kind of phosphate type ternary block polymer dispersing agent of the invention, ATRP preparation process schematic diagram are as follows:
Compared with the existing technology, a kind of phosphate type ternary block polymer dispersing agent of the present invention and its preparation side
Method has the advantage that (1) using methacryloxypropyl alkylol mono phosphoric acid ester esters as monomer, neutralized rear dispersant molecule
Segment contains the efficient anchoring group of phosphate, and anchoring effect and electric double layer effect are obvious；(2) when phosphate anion, carboxylate
Anion-adsorption is in pigment or filler grain surface, and different pigment or filler ion surface are because generating electrical charge rejection between electric double layer
It acts on and spreads out, polyvinylpyrrolidone is because its special structure plays steric effect, so that dispersion is more steady
Fixed, pigment or filler grain be not easy to reunite；(3) dispersing agent of the invention be using ATRP synthetic method molecular weight it is low (4000~
10000), the clamps copolymer of even molecular weight distribution, different dispersant molecule segments, same dispersing agent different segments between
It is not susceptible to mutually wind, therefore dispersing agent dispersion efficiency of the present invention is high, can be widely applied to pigment, powder, glaze
Dispersion.
Specific embodiment
Below with reference to embodiment to a kind of phosphate type ternary block polymer dispersing agent and preparation method thereof of the invention
It is further described.It is understood that specific embodiment described herein is used only for explaining related invention, rather than it is right
The restriction of the invention.
Embodiment 1
A kind of phosphate type ternary block polymer dispersing agent of the present invention, the dispersing agent is with phosphate radical and carboxylic acid
Root is anchoring group, is with pyrrole network alkanone base and steric group, number-average molecular weight 4000~10000, molecular weight polydisperse system
Number is less than 1.3；Its ATRP preparation step is as follows:
(a) in the reaction unit of logical nitrogen, successively by 0.5 part of N, N, N ', N '-tetramethylethylenediamine, 0.7 part of bromination
Cuprous, 0.06 part of octadecyldimethyl vinyl phenyl ammonium chloride, 65 parts of water, 30 parts of methyl acryloyl-oxy amyl alcohol list phosphorus
Acid esters is added in reaction unit, and stirring and emulsifying simultaneously heats up 78 DEG C, and 5~10 parts of 10% part of 4- [10- are added dropwise by Dropping feeder
(the bromo- 2- methylpropionyloxy of 2-) octyloxy] -4- oxo -2- sulfonic group butyric acid disodium aqueous solution, 0.5~1h is added dropwise,
Then 78 DEG C of reaction 1.5h, obtain solution a；
(b) 5 parts of fumaric acid are taken, adding sodium hydroxide solution is neutralized to pH=7, and 10 parts of water dilutions are then added, obtain fumaric acid
Sodium water solution；Fumaric acid sodium aqueous solution is added dropwise dropwise into above-mentioned solution a, 0.5h is added dropwise, the reaction was continued at 75 DEG C 2h, obtains
Solution b；
(c) 10 parts of vinylpyridine network alkanones are dissolved in 30 parts of water, obtain vinylpyridine network alkanone solution；To above-mentioned solution
Vinylpyridine network alkanone solution is added dropwise in b dropwise, 0.5h is added dropwise, then the reaction was continued at 75 DEG C 2h, and natural cooling adds
Enter after sodium hydroxide solution is neutralized to pH-=7 and stop stirring, phosphate type block copolymer dispersant of the present invention is made
Solution is added after precipitating reagent precipitating, dry, washing, re-dry granulation up to of the present invention into copolymer dispersant solution
A kind of phosphate type block copolymer dispersant.
Above-mentioned block polymer dispersant solution is applied to 1250 mesh 70% and contains ceramic glaze admittedly containing kaolin and 70% admittedly
The dispersion of slurry, data are seen attached list.
Embodiment 2
A kind of phosphate type ternary block polymer dispersing agent of the present invention, the dispersing agent is with phosphate radical and carboxylic acid
Root is anchoring group, is with pyrrole network alkanone base and steric group, number-average molecular weight 4000~10000, molecular weight polydisperse system
Number is less than 1.3；Its ATRP preparation step is as follows:
(a) in the reaction unit of logical nitrogen, successively by 1.0 parts of N, N, N ', N ', N "-pentamethyl methyl acrylate base
0.5 part of cuprous bromide of diethylene triamine, 0.05 part of dodecyl dimethyl vinyl phenyl ammonium chloride, 80 parts of water, 30 parts of propylene
Monomethacryloxypropyl alcohol phosplate is added in reaction unit, and stirring and emulsifying simultaneously heats up 90 DEG C, is added dropwise 5 part 10% by Dropping feeder
The aqueous solution of part 4- [10- (the bromo- 2- methylpropionyloxy of 2-) decyloxy] -4- oxo -2- sulfonic group butyric acid disodium, 1h are dripped
Finish, then 70 DEG C of reaction 2h, obtain solution a；
(b) 8 parts of fumaric acid are taken, adding sodium hydroxide solution is neutralized to pH=7, and 5 parts of water dilutions are then added, obtain fumaric acid sodium
Aqueous solution；Fumaric acid sodium aqueous solution is added dropwise dropwise into above-mentioned solution a, 1h is added dropwise, the reaction was continued at 90 DEG C 1h, obtains solution
b；
(c) 15 parts of vinylpyridine network alkanones are dissolved in 30 parts of water, obtain vinylpyridine network alkanone solution；To above-mentioned solution
Vinylpyridine network alkanone solution is added dropwise in b dropwise, 0.5h is added dropwise, then the reaction was continued at 90 DEG C 1.5h, natural cooling,
It is added after sodium hydroxide solution is neutralized to pH-=7 and stops stirring, phosphate type block copolymer dispersion of the present invention is made
Agent solution is added after precipitating reagent precipitating, dry, washing, re-dry granulation up to institute of the present invention into copolymer dispersant solution
A kind of phosphate type block copolymer dispersant stated.
Above-mentioned block polymer dispersant solution is applied to 1250 mesh 70% and contains ceramic glaze admittedly containing kaolin and 70% admittedly
The dispersion of slurry, data are seen attached list.
Embodiment 3
A kind of phosphate type ternary block polymer dispersing agent of the present invention, the dispersing agent is with phosphate radical and carboxylic acid
Root is anchoring group, is with pyrrole network alkanone base and steric group, number-average molecular weight 4000~10000, molecular weight polydisperse system
Number is less than 1.3；Its ATRP preparation step is as follows:
(a) in the reaction unit of logical nitrogen, successively by 0.2 part of N, N, N ', N ', N ", the positive fourth of N "-hexamethyl acrylic acid
Ester group triethylene tetraamine, 1.5 parts of stannous chlorides, 0.05 part of dodecyl dimethyl vinyl phenyl ammonium chloride, 80 parts of water, 30
Part methacryloxypropyl butyl alcohol phosplate is added in reaction unit, and stirring and emulsifying simultaneously heats up 70 DEG C, passes through Dropping feeder
The water-soluble of 5 parts of 10% part of 4- [6- (the bromo- 2- methylpropionyloxy of 2-) hexyloxy] -4- oxo -2- sulfonic group butyric acid disodiums is added dropwise
Liquid, 1h are added dropwise, and then 70 DEG C of reaction 2h, obtain solution a；
(b) 10 parts of fumaric acid are taken, adding sodium hydroxide solution is neutralized to pH=7, and 8 parts of water dilutions are then added, obtain fumaric acid
Sodium water solution；Fumaric acid sodium aqueous solution is added dropwise dropwise into above-mentioned solution a, 0.5~1h is added dropwise, and the reaction was continued at 70 DEG C
1.3h obtains solution b；
(c) 12 parts of vinylpyridine network alkanones are dissolved in 25 parts of water, obtain vinylpyridine network alkanone solution；To above-mentioned solution
Vinylpyridine network alkanone solution is added dropwise in b dropwise, 0.8h is added dropwise, then the reaction was continued at 70 DEG C 1.h, natural cooling,
It is added after sodium hydroxide solution is neutralized to pH-=7 and stops stirring, phosphate type block copolymer dispersion of the present invention is made
Agent solution is added after precipitating reagent precipitating, dry, washing, re-dry granulation up to institute of the present invention into copolymer dispersant solution
A kind of phosphate type block copolymer dispersant stated.
Above-mentioned block polymer dispersant solution is applied to 1500 mesh 70% and contains ceramic glaze admittedly containing kaolin and 70% admittedly
The dispersion of slurry, data are seen attached list.
Dispersing agent dispersion effect data are as follows: with the modest FX-600 contrast effect of moral in embodiment
Claims (5)
1. a kind of preparation method of phosphate type ternary block polymer dispersing agent, which is characterized in that steps are as follows:
(a) in the reaction unit of logical nitrogen, successively by 0.2~1.0 part of ligand, 0.5~1.5 part of catalyst, 0.05~0.1
Part surfactant, 50~80 parts of water, 30 parts of methacryloxypropyl alkylol mono phosphoric acid ester esters monomers are added in reaction unit,
Stirring and emulsifying simultaneously heats up 70~90 DEG C, and the aqueous solution of 5~10 parts of 10% part of initiators, 0.5~1h drop are added dropwise by Dropping feeder
Add complete, then 70~90 DEG C of reaction 1h~2h, obtain solution a；
(b) 5~10 parts of fumaric acid are taken, sodium hydroxide solution is added and is neutralized to pH=7,5~10 parts of water dilutions are then added, obtain rich
Horse acid sodium aqueous solution；Fumaric acid sodium aqueous solution is added dropwise dropwise into above-mentioned solution a, 0.5~1h is added dropwise, at 70~90 DEG C after
Continuous reaction 1h~2h, obtains solution b；
(c) 10~15 parts of vinylpyridine network alkanones are dissolved in 20~30 parts of water, obtain vinylpyridine network alkanone solution；To above-mentioned
Vinylpyridine network alkanone solution is added dropwise in solution b dropwise, 0.5~1h is added dropwise, then the reaction was continued at 70~90 DEG C 1h
~2h, natural cooling are added after sodium hydroxide solution is neutralized to pH=7 and stop stirring, the copolymerization of phosphate type tri-block is made
Object dispersant solution is added after precipitating reagent precipitating, dry, washing, re-dry granulation up to institute into copolymer dispersant solution
The phosphate type ternary block polymer dispersing agent stated；
Wherein, the ligand is N, N, N ', N '-tetramethylethylenediamine, N, N, N ', N ', N "-pentamethyl methyl acrylate base two
Vinyl triamine, N, N, N ', N ', N ", N "-hexamethyl n-butyl acrylate base triethylene tetraamine, 2,2 '-bipyridyls, N, N,
N ', N ', N "-pentamethyldivinyltriamine, N, N, N ', N ', N ", in N "-hexamethyl methyl acrylate base triethylene tetraamine
At least one.
2. a kind of preparation method of phosphate type ternary block polymer dispersing agent according to claim 1, feature exist
In: the catalyst is at least one of cuprous bromide, stannous chloride, cuprous bromide, copper bromide.
3. a kind of preparation method of phosphate type ternary block polymer dispersing agent according to claim 2, feature exist
In: the surfactant is double dodecylphenyl ether sodium disulfonates, odium stearate, sodium laurate, OP-10, phenethyl
Phenol polyethenoxy ether, tween, fatty alcohol polyethenoxy ether class, octadecyldimethyl vinyl phenyl ammonium chloride, dodecyl two
At least one of ethylene methacrylic Phenyl chloride.
4. a kind of preparation method of phosphate type ternary block polymer dispersing agent according to claim 1, feature exist
In: the initiator is 4- [2- (the bromo- 2- methylpropionyloxy of 2-) ethyoxyl] -4- oxo -2- sulfonic group butyric acid disodium, 4-
[10- (the bromo- 2- methylpropionyloxy of 2-) decyloxy] -4- oxo -2- sulfonic group butyric acid disodium, 4- [6- (the bromo- 2- methyl-prop of 2-
Acyloxy) hexyloxy] -4- oxo -2- sulfonic group butyric acid disodium, 4- [10- (the bromo- 2- methylpropionyloxy of 2-) octyloxy] -4-
Oxo -2- sulfonic group butyric acid disodium, 2- chlorine propionamide, 2- bromine propionamide, 2- iodo methyl acrylate, 2- chloro propionitrile, 2- bromine
Ethyl acrylate, 2- bromopropene acid methyl esters, propylene bromide acetoacetic ester, 1- bromoacetonitrile, 2- methyl -2- bromoacrylic acid ethyl ester,
2- isobutyl ethyl bromide, 2- bromopropene acetoacetic ester, N, at least one of N- diethyl -2- bromo acrylamide.
5. a kind of preparation method of phosphate type ternary block polymer dispersing agent according to claim 1, feature exist
In: the methacryloxypropyl alkylol mono phosphoric acid ester esters monomer is methylacryoyloxyethyl alcohol phosplate, methyl-prop
Alkene monomethacryloxypropyl alcohol phosplate, methacryloxypropyl butyl alcohol phosplate, methacryloxypropyl amyl alcohol phosplate, first
At least one of base acryloyl-oxy hexyl alcohol phosplate, methacryloxypropyl heptyl alcohol phosplate.
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| CN109370346B (en) * | 2018-09-27 | 2020-08-25 | 合众（佛山）化工有限公司 | Multifunctional ultrathin steel structure fireproof and anticorrosive water-based paint and construction method |
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| 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 |
| CN116284622B (en) * | 2023-03-15 | 2024-01-23 | 上海宇昂水性新材料科技股份有限公司 | Phosphate type copolymer dispersing agent and preparation method thereof |
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