CN108816152B - Polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant, and preparation method and application thereof - Google Patents
Polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant, and preparation method and application thereof Download PDFInfo
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- CN108816152B CN108816152B CN201810322269.XA CN201810322269A CN108816152B CN 108816152 B CN108816152 B CN 108816152B CN 201810322269 A CN201810322269 A CN 201810322269A CN 108816152 B CN108816152 B CN 108816152B
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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
- C09K23/16—Amines or polyamines
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/182—Graphene
- C01B32/194—After-treatment
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
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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
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/0009—Pigments for ceramics
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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
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/10—Treatment with macromolecular organic compounds
Abstract
The invention discloses a polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant, and a preparation method and application thereof. The dispersant has both polyether side chain and carboxylate side group in the molecular chain of polyethyleneimine, and is prepared with polyethyleneimine, alpha, beta-unsaturated acid salt and polyether alpha, beta-unsaturated acid ester through Michael addition reaction of the primary amino group and secondary amino group in polyethyleneimine and the double bond in alpha, beta-unsaturated acid salt and polyether alpha, beta-unsaturated acid ester. Wherein the polyethyleneimine endows the dispersant with good anchoring effect on the inorganic powder; polyether is a solvation chain, and a three-dimensional blocking effect is given to the dispersing agent; the carboxylic acid is an ionic group that imparts electrostatic repulsion to the dispersant. And the latter two jointly inhibit and prevent agglomeration of dispersed particles, and excellent dispersing performance can be obtained by combining the three aspects. The aqueous dispersant has excellent dispersing performance when applied to aqueous dispersion systems of inorganic powders such as inorganic pigments, silicon carbon powder, graphene and the like.
Description
Technical Field
The invention belongs to the technical field of aqueous dispersants. More particularly, relates to a polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant, and a preparation method and application thereof.
Background
A Dispersant (Dispersant) is a surfactant that has both lipophilic and hydrophilic properties in opposite directions within a molecule. The amphiphilic agent is capable of uniformly dispersing solid and liquid particles of inorganic and organic pigments which are difficult to dissolve in liquids, and also preventing settling and agglomeration of the particles to form stable suspensions. When water-insoluble inorganic powder is ground into an inorganic powder water dispersion system by taking water as a medium, a dispersant is required to be added, wherein the dispersant has the following main functions: (1) the surface of the inorganic powder is modified, and the surface of the particles is quickly and fully wetted, so that the grinding time for reaching the qualified particle fineness is shortened, and the energy loss is reduced; (2) stabilizing the dispersed inorganic powder to prevent aggregation and sedimentation; (3) reduce the viscosity and improve the content of inorganic powder in the powder dispersion system.
In order to achieve good dispersion effect, the dispersant must first form a strong adsorption effect with the surface of inorganic powder particles, and is not easy to desorb, so a certain number of anchoring groups must be introduced into the dispersant molecules. To prevent the aggregation of powder particles, there are two basic methods: firstly, ionic groups are introduced into dispersant molecules, so that electric double layers are formed around powder particles, and the agglomeration of the powder particles is inhibited due to the electrostatic repulsion; secondly, a solvation chain is introduced into the dispersant molecule, and for the aqueous dispersant, a hydrophilic long chain is introduced into the dispersant molecule, and the hydrophilic long chain has good compatibility with water and takes a stretching conformation in the water, so that a protective layer with a certain thickness is formed on the surface of the powder particles, an effective three-dimensional blocking effect is achieved, and the particles are prevented from agglomerating.
The polyethyleneimine is usually a branched polymer, and the molecule contains primary amino, secondary amino and tertiary amino, so that the polyethyleneimine has very unique performance and extremely high chemical reaction activity, various amino contained in the polyethyleneimine can form strong adsorption with various surfaces, and due to the high content of the amino, multi-point anchoring can be formed on the particle surface, and the adsorption fastness is high; the high reactivity of primary and secondary amino groups simultaneously offers a multiplicity of modification possibilities. For example, patent US 20130342593 and WO 2017140538 report that an oil-soluble polyester chain is grafted onto polyethyleneimine by amidation reaction between amino groups of polyethyleneimine molecular chain and carboxyl end groups of carboxyl end group polyester, and the polyester chain acts as a solvating chain to form steric hindrance, thereby obtaining an oil-based pigment dispersant with good performance. With the increasing awareness of environmental protection, the problem of environmental pollution caused by organic substances contained in oily systems is increasingly limited, and thus research and development of aqueous dispersants with excellent performance are receiving great attention. The polyester-modified polyethyleneimine oily dispersants as described above introduce only anchor groups and solvating chains, which may not be sufficient to provide adequate dispersing performance for some applications.
Disclosure of Invention
The invention aims to solve the technical problem of overcoming the defects and shortcomings of the existing water-based dispersant, and simultaneously introduces an ionic group and a water-soluble polyether side chain into a molecular chain of polyethyleneimine, wherein the polyethyleneimine provides an anchoring group, the ionic group provides electrostatic repulsion, and the water-soluble polyether side chain provides a steric hindrance effect, so that the water-based dispersant with excellent performance is obtained.
The invention aims to provide a polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant and a preparation method thereof.
The invention further aims to provide application of the polyether and carboxylic acid double-modified polyethyleneimine aqueous dispersant.
The above purpose of the invention is realized by the following technical scheme:
a polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant comprises a polyethyleneimine molecular chain which simultaneously has polyether side chains and carboxylate side groups.
Specifically, the polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant is prepared by carrying out Michael addition reaction on polyethyleneimine and A and B; that is, polyether side chains and carboxylate pendant groups on the aqueous dispersant are introduced from the Michael addition reaction of primary and secondary amino groups contained in polyethyleneimine with double bonds contained in A and B, by polyethyleneimine with A and B; wherein A is alpha, beta-unsaturated acid salt, and B is alpha, beta-unsaturated acid ester of polyether.
Preferably, the molar ratio of A to B is 3:1 to 6: 1.
Preferably, the polyethyleneimine is a branched polyethyleneimine.
Preferably, the molecular weight of the polyethyleneimine is 500-25000. The molecular weight is too low, and the anchoring effect of the polyethyleneimine on the surface of the inorganic powder is not firm enough; too high a molecular weight may cause handling and solubility problems due to too high a viscosity.
More preferably, the molecular weight of the polyethyleneimine is 1300-10000.
Further, preferably, the α, β -unsaturated acid salt is an acrylate salt, a methacrylate salt, a maleate salt, or a fumarate salt.
More preferably, the α, β -unsaturated acid salt is an acrylate salt, more preferably sodium acrylate.
Preferably, the α, β -unsaturated acid ester of the polyether is an α, β -unsaturated acid ester of polyethylene glycol monomethyl ether.
Preferably, the molecular weight of a polyethylene glycol monomethyl ether chain in the alpha, beta-unsaturated acid ester of the polyethylene glycol monomethyl ether is 500-3000. The molecular weight is too low, the steric hindrance effect of the polyethylene glycol chain is not obvious, and the sufficient steric hindrance effect is difficult to generate; if the molecular weight is too high, the affinity of the dispersant for water may be too high, which not only easily causes the desorption of dispersant molecules from the particle surface, but also may cause overlong molecular chains to fold on the particle surface, thereby compressing the steric hindrance effect, and even may cause entanglement of polyethylene glycol chains on different particles, finally causing agglomeration of the particles.
More preferably, the molecular weight of the polyethylene glycol monomethyl ether chain in the alpha, beta-unsaturated acid ester of the polyethylene glycol monomethyl ether is 1000-2000.
More preferably, the alpha, beta-unsaturated acid ester of the polyethylene glycol monomethyl ether is one or a mixture of polyethylene glycol monomethyl ether acrylate, polyethylene glycol monomethyl ether methacrylate and polyethylene glycol monomethyl ether maleic acid monoester sodium. Polyethylene glycol monomethyl ether acrylate is most preferred.
The invention also provides a specific alternative scheme, and the preparation method of the aqueous dispersant comprises the following steps: adding water and polyethyleneimine into a reaction container, stirring and dissolving uniformly, heating to 50-60 ℃, dropwise adding a mixed aqueous solution of an alpha, beta-unsaturated acid salt and a polyether alpha, beta-unsaturated acid ester under stirring, completing dropwise addition within 0.5-1.5 h (preferably 1 h), and continuing to react for 2.5-3.5 h (preferably 3 h) after completing dropwise addition.
The polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant disclosed by the invention shows an excellent dispersing effect in an aqueous dispersion system of an inorganic pigment, silicon carbon powder (Si-C) and graphene.
Therefore, the application of the polyether and carboxylic acid double-modified polyethyleneimine aqueous dispersant in an inorganic powder aqueous dispersion system also falls within the protection scope of the invention.
Preferably, the inorganic powder includes inorganic pigment, silicon carbon powder (Si-C), graphene, and the like.
The invention has the following beneficial effects:
the invention provides a polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant, which simultaneously has a polyether side chain and a carboxylate side group on a polyethyleneimine molecular chain and is prepared by Michael addition reaction of primary amino groups and secondary amino groups contained in polyethyleneimine, alpha, beta-unsaturated acid salts and alpha, beta-unsaturated acid esters of polyether, and double bonds contained in the alpha, beta-unsaturated acid salts and the alpha, beta-unsaturated acid esters of polyether.
In the dispersant, polyethyleneimine endows the dispersant with a good anchoring effect on inorganic powder; polyether is a solvation chain, and a three-dimensional blocking effect is given to the dispersing agent; the carboxylic acid is an ionic group that imparts electrostatic repulsion to the dispersant. And the latter two jointly inhibit and prevent agglomeration of dispersed particles, and excellent dispersing performance can be obtained by combining the three aspects. The aqueous dispersant has excellent dispersing performance when applied to aqueous dispersion systems of inorganic powders such as inorganic pigments, silicon carbon powder, graphene and the like.
Detailed Description
The present invention is further illustrated by the following specific examples, which are not intended to limit the invention in any way. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated. Unless otherwise indicated, reagents and materials used in the present invention are commercially available.
In the following examples, sodium acrylate was dissolved in acrylic acid with water, and then neutralized with an aqueous NaOH solution under cooling to prepare a 40% aqueous sodium acrylate solution for use.
The particle size of the dispersion system is measured by a laser particle sizer Mastersizer 2000; the viscosity was measured with a rotational viscometer; conditions for measuring centrifugal sedimentation rate: the centrifugal speed is 3000 r/min; centrifuging for 5 min.
Example 1
Adding 43g of polyethyleneimine (MW 1300) and 64.5g of water into a reaction bottle, stirring and dissolving, heating to 50-60 ℃, dropwise adding a mixed solution prepared from 105.8g of 40% sodium acrylate solution, 300g of polyethylene glycol monomethyl ether (2000) acrylate and 450g of water (the molar ratio of sodium acrylate to polyethylene glycol monomethyl ether acrylic acid is 3: 1), continuously reacting for about 3 hours after dropwise adding, and cooling to obtain the aqueous dispersant with the solid content of 40%.
Example 2
Adding 43g of polyethyleneimine (MW 10000) and 64.5g of water into a reaction bottle, stirring and dissolving, heating to 50-60 ℃, dropwise adding a mixed solution prepared from 140 g of 40% sodium acrylate solution, 100 g of polyethylene glycol monomethyl ether (1000) acrylate and 150 g of water (the molar ratio of sodium acrylate to polyethylene glycol monomethyl ether acrylate is 6: 1), continuously reacting for about 3 hours after dropwise adding, and cooling to obtain the aqueous dispersant with the solid content of 40%.
Example 3
Adding 43g of polyethyleneimine (MW 15000) and 64.5g of water into a reaction bottle, stirring for dissolving, heating to 50-60 ℃, dropwise adding a mixed solution prepared from 105.8g of 40% sodium methacrylate solution, 300g of polyethylene glycol monomethyl ether (500) acrylate and 450g of water (the molar ratio of sodium acrylate to polyethylene glycol monomethyl ether acrylate is 4: 1), dropwise adding for about 1 hour, continuing to react for about 3 hours after dropwise adding, and cooling to obtain the aqueous dispersant, wherein the solid content of the aqueous dispersant is 40%.
Example 4
Adding 43g of polyethyleneimine (MW 20000) and 64.5g of water into a reaction bottle, stirring for dissolving, heating to 50-60 ℃, dropwise adding a mixed solution prepared from 140 g of 40% sodium maleate solution, 100 g of polyethylene glycol monomethyl ether (3000) acrylate and 150 g of water (the molar ratio of sodium acrylate to polyethylene glycol monomethyl ether acrylate is 5: 1), continuously reacting for about 3 hours after dropwise adding, and cooling to obtain the aqueous dispersant with the solid content of 40%.
Example 5
The dispersing effect of the dispersant of the invention on inorganic pigments in aqueous media was experimentally studied on the representative of ceramic color glaze (praseodymium yellow, brown red, cobalt blue; metal glaze, glitter glaze).
The ceramic color glaze material is added with water and the dispersant of the embodiment 1 to prepare a grinding material with the pigment content of 45 percent and the dispersant dosage of 12 percent of the total amount, and the grinding material is ground for 1 hour by a rod-tip type sand mill. The results of the dispersion property test are shown in Table 1.
Table 1 example 1 dispersing effect of dispersant on ceramic colored glaze
The results in Table 1 show that the dispersant of the present invention has excellent dispersing performance for inorganic pigments in an aqueous medium.
Example 6
The dispersant of example 1 was replaced with the dispersant of example 2, and the other conditions were the same as in example 5. The results of the dispersion property test are shown in Table 2.
Table 2 example 2 dispersing effect of dispersant on ceramic colored glaze
As can be seen from tables 1 and 2, the dispersant of the present invention has excellent dispersion effect on ceramic color glaze, small particle size of milled color paste, short milling time, high color glaze content, small viscosity of color paste, and low centrifugal sedimentation rate.
Example 7
Silicon carbon powder (with the initial particle size of about 30 microns), the dispersant in example 1 and water are mixed to prepare a grinding material with the silicon carbon powder content of 10% and the dispersant addition amount of 10% of the total amount, and the grinding material is ground, sampled at certain intervals and subjected to particle size analysis. The results are shown in Table 3.
Table 3 example 1 dispersing effect of dispersant on silicon carbon powder
As can be seen from Table 3, the dispersant of the present invention has a good dispersing effect on the silicon carbon powder, and the particle size of the silicon carbon is reduced with the extension of the grinding time, and no coarsening phenomenon occurs.
Example 8
Graphene (with an initial particle size of about 50 μm), the dispersant of example 1 and water were mixed to prepare a mill base with a graphene content of 6% and a dispersant addition of 40% of the graphene, which was ground, and samples were taken at regular intervals to perform particle size analysis. The results are shown in Table 4.
Table 4 example 1 dispersing effect of dispersant on graphene
As can be seen from table 4, the aqueous dispersant of the present invention can grind graphene to a particle size of 100 nm in a short time, demonstrating that the dispersant has an excellent dispersing effect on graphene.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (5)
1. A polyether and carboxylic acid double-modified polyethyleneimine water-based dispersant is characterized in that a polyethyleneimine molecular chain simultaneously has a polyether side chain and a carboxylate side group;
wherein the aqueous dispersant is prepared by a Michael addition reaction of polyethyleneimine and A and B;
a is an alpha, beta-unsaturated acid salt, and the alpha, beta-unsaturated acid salt is acrylate, methacrylate, maleate or fumarate; b is alpha, beta-unsaturated acid ester of polyether, the alpha, beta-unsaturated acid ester of polyether is one or a mixture of polyethylene glycol monomethyl ether acrylate, polyethylene glycol monomethyl ether methacrylate and polyethylene glycol monomethyl ether maleic acid monoester sodium;
the polyethyleneimine is branched polyethyleneimine, and the molecular weight of the polyethyleneimine is 500-25000.
2. The aqueous dispersant of claim 1, wherein the molar ratio of A to B is 3:1 to 6: 1.
3. The aqueous dispersant according to claim 1, wherein the molecular weight of the polyethylene glycol monomethyl ether chain in the α, β -unsaturated acid ester of the polyether is 500 to 3000.
4. The aqueous dispersant of claim 1, wherein the michael addition reaction is carried out by: adding water and polyethyleneimine into a reaction container, stirring and dissolving uniformly, heating to 50-60 ℃, dropwise adding a mixed aqueous solution of an alpha, beta-unsaturated acid salt and a polyether alpha, beta-unsaturated acid ester under stirring, completing dropwise addition within 0.5-1.5 h, and continuing to react for 2.5-3.5 h after completing dropwise addition.
5. The use of the polyether and carboxylic acid double modified polyethyleneimine aqueous dispersant of any one of claims 1 to 4 in an inorganic powder aqueous dispersion system.
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| CN110903438B (en) * | 2019-12-19 | 2022-05-17 | 上海晨光文具股份有限公司 | Water-based dispersant for ink system and preparation method thereof |
| CN112048335B (en) * | 2020-07-10 | 2022-05-10 | 天津海润金科科技有限公司 | Synchronous demulsification water purifier for petroleum produced liquid |
| CN112144122A (en) * | 2020-10-21 | 2020-12-29 | 常州时创能源股份有限公司 | Texturing additive and texturing liquid suitable for large-size monocrystalline silicon wafers and application |
| CN113174017B (en) * | 2021-03-23 | 2023-12-22 | 黄山万丽美油墨科技有限公司 | Water-based dispersing agent for ceramic glaze as well as preparation method and application thereof |
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