CN110540639B - Parallel-connection type high-molecular water-based organic pigment dispersant, and preparation and application thereof - Google Patents

Parallel-connection type high-molecular water-based organic pigment dispersant, and preparation and application thereof Download PDF

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CN110540639B
CN110540639B CN201910844629.7A CN201910844629A CN110540639B CN 110540639 B CN110540639 B CN 110540639B CN 201910844629 A CN201910844629 A CN 201910844629A CN 110540639 B CN110540639 B CN 110540639B
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刘敏
潘琦
任凡
付远波
王亮
万浩轩
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Wuhan Oxiran Specialty Chemicals Co
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
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    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
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    • 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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    • C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
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    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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Abstract

The invention provides a parallel-connection type high-molecular water-based pigment dispersant, which has a comb-shaped branched structure and comprises naphthalene rings and a peripheral ethylene oxide/propylene oxide polymer long chain, wherein the structural formula of the parallel-connection type high-molecular water-based pigment dispersant is as follows:
Figure DDA0003205508840000011
in the structural formula, in the formula,
Figure DDA0003205508840000012
wherein n is 26-38, x is 15-22, and y is 44-63. The invention also provides a preparation method and application of the parallel-connection type high-molecular water-based pigment dispersant. The parallel-connection type high-molecular water-based pigment dispersing agent has excellent dispersion stability, storage stability and redissolution property on organic pigments, high grinding efficiency, strong viscosity reduction property and good color development property; the pigment has strong universality, is suitable for various inorganic, organic and mixed pigments, and is particularly suitable for the fields of high-solid pigment-containing color paste, water-based paint systems, printing ink, electronic ink jet and the like; the method can maintain that the water-based color paste does not flocculate and deposit for a long time (as long as 30 days), and ensures the good stability of the system.

Description

Parallel-connection type high-molecular water-based organic pigment dispersant, and preparation and application thereof
Technical Field
The invention relates to the technical field of pigment dispersants, and particularly relates to a parallel-connection type high-molecular water-based organic pigment dispersant, and preparation and application thereof.
Background
In the fields of applications such as paints, inks, etc., the dispersion of pigments is an important part of the manufacturing technology. To obtain a uniform stable dispersion, it is often necessary to use a dispersing agent. The dispersing agent is a surfactant which has two opposite properties of lipophilicity and hydrophilicity in a molecule, is adsorbed on the surface of pigment particles, enables the surface of the agglomerated pigment particles to be easily wetted, forms an adsorption layer on the surface, increases the charge on the surface of the pigment particles, and improves the reaction force between the particles forming steric hindrance, so that solid particles of inorganic and organic pigments which are difficult to dissolve in liquid can be uniformly dispersed, and simultaneously, the sedimentation and agglomeration of the solid particles can be prevented, and stable suspension liquid is formed. The excellent wetting dispersant can reduce the time and energy required for completing the dispersion process, stabilize the dispersed pigment dispersion, modify the surface properties of the pigment particles, and adjust the mobility of the pigment particles, thereby achieving the following effects: shorten dispersion time, improve luster, improve tinting strength and hiding power, improve color development and color tone, prevent floating color and floating flower, prevent flocculation and prevent sedimentation.
Chinese patent application CN 106220799A discloses a novel modified polyether dispersant, which is prepared by copolymerizing acrylic acid-maleic anhydride-styrene copolymer with polyether containing functional groups under the action of a catalyst, introducing block polyether, and obtaining the modified polyether dispersant which not only has a plurality of carboxylic acid groups, but also contains aromatic rings and amphiphilic EO/PO block structures, thereby greatly improving the stability and compatibility of the pigment.
Chinese patent application CN 102974267 a discloses a pigment auxiliary agent, which comprises fatty alcohol-polyoxyethylene ether, fatty alcohol-polyoxyethylene ether monoester, fatty alcohol-polyoxyethylene ether diester, carboxylated fatty alcohol-polyoxyethylene ether monoester, and carboxylated fatty alcohol-polyoxyethylene ether diester. The dispersing agent is suitable for dispersing pigments, and has good dispersing performance and high stability.
Chinese patent CN 101056932B discloses a water-soluble product obtained by reacting monofunctional amine based polyethers with condensed glycerol ethers of polyols, which product can be used in end-use dispersants and formulations known to use dispersants. And a process comprising reacting a monofunctional amine-terminated polyether with a glycidyl ether of a polyol is provided.
However, the above-disclosed dispersants are not satisfactory in combination of pigment wetting dispersion, viscosity reduction, dispersion efficiency, storage temperature properties, color developability, and the like.
Disclosure of Invention
Based on the defects of the prior art, the invention aims to provide a parallel-connection type high-molecular water-based pigment dispersant which has strong pigment wetting and dispersing effects, good viscosity reduction performance, high dispersing efficiency, stronger storage stability and excellent color development performance and ensures good application of the pigment in a paint and ink system.
The invention provides a parallel-connection type high-molecular water-based pigment dispersant, which has a comb-shaped branched structure and comprises parallel naphthalene rings and a peripheral ethylene oxide/propylene oxide polymer long chain, wherein the structural formula of the parallel-connection type high-molecular water-based pigment dispersant is as follows:
Figure GDA0003205508830000021
in the structural formula, in the formula,
Figure GDA0003205508830000022
wherein n is 26-38, x is 15-22, and y is 44-63.
The invention also provides a preparation method of the parallel-connection type high-molecular water-based pigment dispersant, which comprises the following steps:
putting alpha-naphthol, a phenolic aldehyde catalyst and an aldehyde substance aqueous solution into a reaction kettle for polycondensation reaction, wherein the temperature of the polycondensation reaction is 90-105 ℃, and the time of the polycondensation reaction is 3-6 h;
dehydrating the polycondensation reaction product to obtain naphthol phenolic resin;
putting the naphthol phenolic resin and the graft polymerization catalyst into a reaction kettle, and sequentially adding propylene oxide and ethylene oxide according to a proportion to carry out graft polymerization reaction at the temperature of 120-160 ℃ and the pressure of 0.2-0.45 MPa;
and adding a neutralizing agent for neutralization to obtain the parallel-connection type high-molecular water-based pigment dispersing agent.
Preferably, the molar ratio of the alpha-naphthol to the aqueous solution of aldehyde substances is 1: 0.9-1.1, and the charging amount of the phenolic aldehyde catalyst is 0.5-2.5% of the mass fraction of the charging amount of the alpha-naphthol.
As a preferable scheme, the aqueous solution of the aldehyde substance is dripped into the reaction kettle, and the dripping temperature of the aqueous solution of the aldehyde substance is 30-40 ℃.
Preferably, the phenolic aldehyde catalyst is one or more of hydrochloric acid, oxalic acid, sulfuric acid and p-toluenesulfonic acid, and the graft polymerization catalyst is one or more of potassium hydroxide, sodium methoxide, potassium methoxide and sodium hydride.
As a preferable mode, the step of dehydrating the polycondensation reaction product to obtain the naphthol phenol resin comprises: and adding a dehydrating agent, heating to 135-150 ℃, refluxing, dehydrating and distilling under reduced pressure to obtain the naphthol phenolic resin.
Preferably, the dehydrating agent is xylene, and the feeding amount of the xylene is 0.9-1.6 times of the mass of the feeding amount of the aldehyde substance aqueous solution.
As a preferable scheme, the mass ratio of the naphthol phenolic resin to the propylene oxide to the ethylene oxide is 1: 6-9: 13-20, wherein the feeding amount of the graft polymerization catalyst is 0.1-1% of the total feeding amount by mass fraction.
As a preferable scheme, the step of putting the naphthol phenolic resin and the graft polymerization catalyst into a reaction kettle, and sequentially adding propylene oxide and ethylene oxide in proportion to perform graft polymerization reaction at the temperature of 120-160 ℃ and the pressure of 0.2-0.45 MPa comprises the following steps: slowly adding propylene oxide at the temperature of 130-145 ℃ and under the reaction pressure of 0.25-0.45 MPa until the pressure of the reaction kettle is not reduced any more; slowly adding ethylene oxide at the temperature of 140-155 ℃ and the reaction pressure of 0.25-0.45 MPa until the pressure of the reaction kettle is not reduced; and continuously curing for 0.5-1 h.
The parallel-connection type high-molecular water-based pigment dispersant provided by the invention is applied to the fields of color paste, coating, printing ink and electronic ink jet.
The parallel-connection type high-molecular water-based pigment dispersing agent provided by the invention has excellent dispersion stability, storage stability and redissolution property on organic pigments, high grinding efficiency, strong viscosity reduction property and good color development property; the pigment has strong universality, is suitable for various inorganic, organic and mixed pigments, and is particularly suitable for the fields of high-solid pigment-containing color paste, water-based paint systems, printing ink, electronic ink jet and the like; tests show that the waterborne color paste can maintain the flocculation-free deposition of the waterborne color paste for a long time (up to 30 days), and ensure the good stability of the system.
Drawings
FIG. 1 is a comparison graph of color development of a black paste sample milled by using the parallel-type polymeric aqueous organic pigment dispersant prepared in examples 1 to 3 and a carbon black M310 color paste sample milled by using a market pigment dispersant (market samples 1 and 2).
FIG. 2 is a comparison graph of color development of a red paste sample milled with the parallel-type polymeric aqueous organic pigment dispersant prepared in examples 1-3 and a pigment Red F5RK color paste sample milled with the commercial pigment dispersant (market sample 1, 2).
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the accompanying drawings and the embodiments, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. The embodiments described below and the features of the embodiments can be combined with each other without conflict.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
The invention provides a parallel-connection type high-molecular water-based pigment dispersant, which has a comb-shaped branched structure and comprises parallel naphthalene rings and a peripheral ethylene oxide/propylene oxide polymer long chain, wherein the structural formula of the parallel-connection type high-molecular water-based pigment dispersant is as follows:
Figure GDA0003205508830000041
in the structural formula, in the formula,
Figure GDA0003205508830000042
wherein n is 26-38, x is 15-22, and y is 44-63. The parallel-connection type high-molecular water-based pigment dispersant is applied to the fields of color paste, paint printing ink, electronic ink jet and the like.
The parallel rigid naphthalene ring skeleton in the parallel high-molecular water-based pigment dispersant is an anchoring group, has a structure similar to that of an organic pigment, has a good affinity effect on the organic pigment, and forms anchoring adsorption with the surface of the organic pigment; the ethylene oxide/propylene oxide polymer long chains positioned at the periphery are used as solvating chain segments and are uniformly distributed outside the pigment in a dispersing way, so that an effective steric hindrance effect is formed on pigment particles, the dispersed pigment particles are prevented from adsorbing and flocculating again, good stereo stability is provided, the pigment particles can be well dissolved in an aqueous system, the wetting of the surface of the organic pigment is accelerated, and the grinding efficiency is improved; meanwhile, the length of the ethylene oxide/propylene oxide hydrophilic and hydrophobic groups of the side chains and the polymerization degree of the skeleton naphthalene ring parallel groups are adjusted and optimized, so that the dispersibility of the synthesized polymer can achieve the optimal application effect; thereby comprehensively improving the pigment grinding dispersion efficiency, viscosity reduction, stability, color development and wide applicability of the water-based pigment dispersant.
The parallel-connection type high-molecular water-based pigment dispersing agent provided by the invention has excellent dispersion stability, storage stability and redissolution property on organic pigments, high grinding efficiency, strong viscosity reduction property and good color development property; the pigment has strong universality, is suitable for various inorganic, organic and mixed pigments, and is particularly suitable for the fields of high-solid pigment-containing color paste, water-based paint systems, printing ink, electronic ink jet and the like; tests show that the waterborne color paste can maintain the flocculation-free deposition of the waterborne color paste for a long time (up to 30 days), and ensure the good stability of the system.
The invention also provides a preparation method of the parallel-connection type high-molecular water-based pigment dispersant, which comprises the following steps:
s1: putting alpha-naphthol, a phenolic aldehyde catalyst and an aldehyde substance aqueous solution into a reaction kettle for polycondensation reaction. Wherein the temperature of the polycondensation reaction is 90-105 ℃, and the time of the polycondensation reaction is 3-6 h. The molar ratio of the alpha-naphthol to the aqueous solution of the aldehyde substances is 1: 0.9-1.1, and the feeding amount of the phenolic aldehyde catalyst is 0.5-2.5% of the mass fraction of the feeding amount of the alpha-naphthol.
The aldehyde substance is one of formaldehyde, acetaldehyde and butyraldehyde. Preferably, the aqueous solution of the aldehyde substance is a formaldehyde aqueous solution with the mass fraction of 37%. The phenolic aldehyde catalyst is one or more of hydrochloric acid, oxalic acid, sulfuric acid and p-toluenesulfonic acid.
Preferably, the aqueous solution of the aldehyde substance is dripped into the reaction kettle, and the dripping temperature of the aqueous solution of the aldehyde substance is 30-40 ℃.
S2: and dehydrating the polycondensation reaction product to obtain the naphthol phenolic resin.
Step S2 specifically includes the following steps: and adding a dehydrating agent, heating to 135-150 ℃, refluxing, dehydrating and distilling under reduced pressure to obtain the naphthol phenolic resin. Preferably, the dehydrating agent is xylene, and the feeding amount of the xylene is 0.9-1.6 times of the mass of the feeding amount of the aldehyde substance aqueous solution.
S3: putting the naphthol phenolic resin and the graft polymerization catalyst into a reaction kettle, sequentially adding a certain proportion of propylene oxide and ethylene oxide at the temperature of 120-160 ℃ and the pressure of 0.2-0.45 MPa, and carrying out graft polymerization reaction at high temperature and high pressure. Wherein the mass ratio of the naphthol phenolic resin to the propylene oxide to the ethylene oxide is 1: 6-9: 13-20, wherein the feeding amount of the graft polymerization catalyst is 0.1-1% of the total feeding amount by mass fraction.
The graft polymerization catalyst is one or more of potassium hydroxide, sodium methoxide, potassium methoxide and sodium hydride.
Preferably, step S3 includes: slowly adding propylene oxide at the temperature of 130-145 ℃ and under the reaction pressure of 0.25-0.45 MPa until the pressure of the reaction kettle is not reduced any more; slowly adding ethylene oxide at the temperature of 140-155 ℃ and the reaction pressure of 0.25-0.45 MPa until the pressure of the reaction kettle is not reduced; and continuously curing for 0.5-1 h.
S4: and adding a neutralizing agent for neutralization to obtain the parallel-connection type high-molecular water-based pigment dispersing agent. Preferably, the neutralizing agent is acetic acid.
Example 1
Alpha-naphthol is used as a raw material, oxalic acid is used as a catalyst, formaldehyde aqueous solution with the mass fraction of 37% is dripped, the dripping temperature is 30 ℃, and the reaction is carried out for 6 hours at the temperature of 90 ℃. The mol ratio of the alpha-naphthol to the formaldehyde aqueous solution is 1:0.9, and the feeding amount of the oxalic acid is 0.5 percent of the mass of the feeding amount of the alpha-naphthol. After the reaction is finished, adding a dehydrating agent xylene with the mass 0.9 time that of the formaldehyde aqueous solution, heating to 135 ℃, refluxing and dehydrating, and carrying out reduced pressure distillation to obtain the naphthol phenolic resin.
Using naphthol phenolic resin as an initiator and 0.1 percent of potassium hydroxide as a catalyst, slowly adding Propylene Oxide (PO) at the temperature of 145 ℃ and the reaction pressure of 0.45MPa until the pressure of a reaction kettle is not reduced; slowly adding Ethylene Oxide (EO) at the temperature of 155 ℃ and the reaction pressure of 0.45MPa until the pressure of the reaction kettle is not reduced any more, and continuously curing for 1 hour. Wherein the mass ratio m (initiator) of the naphthol phenolic resin to the propylene oxide to the ethylene oxide is as follows: m (PO): m (EO) is 1: 9: 20. and finally adding acetic acid for neutralization to obtain the parallel-connection type high-molecular water-based organic pigment dispersant with the structure meeting the design requirement.
Example 2
Alpha-naphthol is used as a raw material, oxalic acid is used as a catalyst, formaldehyde aqueous solution with the mass fraction of 37% is dripped, the dripping temperature is 35 ℃, and the reaction is carried out for 3 hours at the temperature of 105 ℃. The mol ratio of the alpha-naphthol to the formaldehyde aqueous solution is 1:1.0, and the feeding amount of the oxalic acid is 1.5 percent of the mass of the feeding amount of the alpha-naphthol. After the reaction is finished, adding a dehydrating agent xylene with the mass 1.2 times that of the formaldehyde aqueous solution, heating to 142 ℃, refluxing and dehydrating, and carrying out reduced pressure distillation to obtain the naphthol phenolic resin.
Using naphthol phenolic resin as an initiator and 0.5 percent of potassium methoxide as a catalyst, slowly adding Propylene Oxide (PO) at the temperature of 140 ℃ and the reaction pressure of 0.35MPa until the pressure of a reaction kettle is not reduced; slowly adding Ethylene Oxide (EO) at the temperature of 145 ℃ and the reaction pressure of 0.4MPa until the pressure of the reaction kettle is not reduced any more, and continuously curing for 0.5 h. Wherein the mass ratio m (initiator) of the naphthol phenolic resin to the propylene oxide to the ethylene oxide is as follows: m (PO): m (EO) is 1: 8: 16. and finally adding acetic acid for neutralization to obtain the parallel-connection type high-molecular water-based organic pigment dispersant with the structure meeting the design requirement.
Example 3
Alpha-naphthol is used as a raw material, p-toluenesulfonic acid is used as a catalyst, formaldehyde aqueous solution with the mass fraction of 37% is dripped, the dripping temperature is 40 ℃, and the reaction is carried out for 5 hours at the temperature of 100 ℃. The mol ratio of the alpha-naphthol to the formaldehyde aqueous solution is 1:1.1, and the feeding amount of the p-toluenesulfonic acid is 2.5 percent of the mass of the alpha-naphthol feeding amount. After the reaction is finished, adding a dehydrating agent xylene with the mass 1.6 times that of the formaldehyde aqueous solution, heating to 150 ℃, refluxing and dehydrating, and carrying out reduced pressure distillation to obtain the naphthol phenolic resin.
Using naphthol phenolic resin as an initiator and 1.0 percent of potassium hydroxide as a catalyst, slowly adding Propylene Oxide (PO) at the temperature of 130 ℃ and the reaction pressure of 0.25MPa until the pressure of a reaction kettle is not reduced; slowly adding Ethylene Oxide (EO) at the temperature of 140 ℃ and the reaction pressure of 0.25MPa until the pressure of the reaction kettle is not reduced any more, and continuously curing for 1 hour. Wherein the mass ratio m (initiator) of the naphthol phenolic resin to the propylene oxide to the ethylene oxide is as follows: m (PO): m (EO) is 1: 6: 13. and finally adding acetic acid for neutralization to obtain the parallel-connection type high-molecular water-based organic pigment dispersant with the structure meeting the design requirement.
The parallel-connection type high-molecular water-based organic pigment dispersing agent and the market dispersing agent prepared in the above examples 1 to 3 are respectively prepared into water-based color paste, and the dispersing performance of the dispersing agent samples prepared in the examples 1 to 3 and the market dispersing agent comparative samples in different types of organic pigments is tested under the same conditions. The formula of the water-based color paste is shown in the table 1, and the test result is shown in the table 2. In Table 2, (M310) pigment is carbon black pigment, (BGS) pigment is phthalocyanine blue pigment, (F5RK) pigment is pigment red pigment, and (G) is phthalocyanine green pigment.
TABLE 1 aqueous color paste formulation
Figure GDA0003205508830000081
Table 2 results of different dispersant samples on pigment dispersion test
Figure GDA0003205508830000082
Figure GDA0003205508830000091
It can be seen from table 2 that the dispersant samples prepared in examples 1-3 have significantly better grinding, dispersing and viscosity reducing effects on organic pigments than the comparative samples (market samples 1 and 2) of the market dispersants; the pigment can be uniformly dispersed for a long time without flocculation and deposition, and stable color paste is formed, thereby ensuring the good stability of the system.
As can be seen from FIGS. 1 and 2, the color developability of the carbon black M310 color paste and the pigment Red F5RK color paste milled by using the parallel-type polymer aqueous organic pigment dispersant prepared in examples 1-3 is better than the blackness of the color pastes milled by using the market samples 1 and 2.
In addition, other modifications within the spirit of the invention will occur to those skilled in the art, and it is understood that such modifications are included within the scope of the invention as claimed.

Claims (10)

1. A parallel-connection type high-molecular water-based pigment dispersant is characterized in that: the parallel high-molecular water-based pigment dispersant has a comb-shaped branch structure, comprises parallel naphthalene rings and a peripheral ethylene oxide/propylene oxide polymer long chain, and has the following structural formula:
Figure FDA0003205508820000011
in the structural formula, in the formula,
Figure FDA0003205508820000012
wherein n is 26-38, x is 15-22, and y is 44-63.
2. A method for preparing the parallel-connection type high molecular water-based pigment dispersant of claim 1, which comprises the following steps:
putting alpha-naphthol, a phenolic aldehyde catalyst and an aldehyde substance aqueous solution into a reaction kettle for polycondensation reaction, wherein the temperature of the polycondensation reaction is 90-105 ℃, and the time of the polycondensation reaction is 3-6 h;
dehydrating the polycondensation reaction product to obtain naphthol phenolic resin;
putting the naphthol phenolic resin and the graft polymerization catalyst into a reaction kettle, and sequentially adding propylene oxide and ethylene oxide according to a proportion to carry out graft polymerization reaction at the temperature of 120-160 ℃ and the pressure of 0.2-0.45 MPa;
and adding a neutralizing agent for neutralization to obtain the parallel-connection type high-molecular water-based pigment dispersing agent.
3. The preparation method of the parallel-connection type high molecular water-based pigment dispersant of claim 2, wherein the molar ratio of the alpha-naphthol to the aldehyde substance aqueous solution is 1: 0.9-1.1, and the charging amount of the phenolic aldehyde catalyst is 0.5-2.5% of the charging amount of the alpha-naphthol by mass fraction.
4. The method for preparing the parallel-connection type high molecular water-based pigment dispersant according to claim 2, wherein the aldehyde substance aqueous solution is dripped into the reaction kettle, and the dripping temperature of the aldehyde substance aqueous solution is 30 to 40 ℃.
5. The method for preparing a parallel-connection type high molecular water-based pigment dispersant according to claim 2, wherein the phenolic aldehyde catalyst is one or more of hydrochloric acid, oxalic acid, sulfuric acid and p-toluenesulfonic acid, and the graft polymerization catalyst is one or more of potassium hydroxide, sodium methoxide, potassium methoxide and sodium hydride.
6. The method for producing a parallel-connection type high molecular aqueous pigment dispersant according to claim 2, wherein the step of dehydrating the polycondensation reaction product to obtain a naphthol phenol resin comprises: and adding a dehydrating agent, heating to 135-150 ℃, refluxing, dehydrating and distilling under reduced pressure to obtain the naphthol phenolic resin.
7. The method for preparing a parallel-connection type high molecular water-based pigment dispersant according to claim 6, wherein the dehydrating agent is xylene, and the dosage of the xylene is 0.9 to 1.6 times of the mass of the aqueous solution of the aldehyde substance.
8. The preparation method of the parallel-connection type high molecular water-based pigment dispersant according to claim 2, wherein the mass ratio of the naphthol phenolic resin to the propylene oxide to the ethylene oxide is 1: 6-9: 13-20, wherein the feeding amount of the graft polymerization catalyst is 0.1-1% of the total feeding amount by mass fraction.
9. The preparation method of the parallel-connection type high molecular water-based pigment dispersant according to claim 2, wherein the step of putting the naphthol phenolic resin and the graft polymerization catalyst into a reaction kettle, and sequentially adding propylene oxide and ethylene oxide according to the proportion to perform graft polymerization reaction at the temperature of 120-160 ℃ and the pressure of 0.2-0.45 MPa comprises the following steps: slowly adding propylene oxide at the temperature of 130-145 ℃ and under the reaction pressure of 0.25-0.45 MPa until the pressure of the reaction kettle is not reduced any more; slowly adding ethylene oxide at the temperature of 140-155 ℃ and the reaction pressure of 0.25-0.45 MPa until the pressure of the reaction kettle is not reduced; and continuously curing for 0.5-1 h.
10. The use of the parallel-connection type polymeric aqueous pigment dispersant according to claim 1, wherein: the parallel-connection type high-molecular water-based pigment dispersant is applied to the fields of color paste, coating, printing ink and electronic ink jet.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5532346A (en) * 1994-10-21 1996-07-02 Milliken Research Corporation Hydroxynaphthalenecarboxylic acid compounds and azo colorants made therefrom
CN106432661A (en) * 2016-09-18 2017-02-22 江苏苏博特新材料股份有限公司 Modified naphthalene water reducer and preparation method thereof
CN106632930A (en) * 2016-09-18 2017-05-10 江苏苏博特新材料股份有限公司 Modified polycondensation type water reducing agent, and preparation method and application thereof
CN108276979A (en) * 2017-12-20 2018-07-13 武汉奥克特种化学有限公司 A kind of temperature-resistant and anti-salt type polyether sulfonate oil displacement agent and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5532346A (en) * 1994-10-21 1996-07-02 Milliken Research Corporation Hydroxynaphthalenecarboxylic acid compounds and azo colorants made therefrom
CN106432661A (en) * 2016-09-18 2017-02-22 江苏苏博特新材料股份有限公司 Modified naphthalene water reducer and preparation method thereof
CN106632930A (en) * 2016-09-18 2017-05-10 江苏苏博特新材料股份有限公司 Modified polycondensation type water reducing agent, and preparation method and application thereof
CN108276979A (en) * 2017-12-20 2018-07-13 武汉奥克特种化学有限公司 A kind of temperature-resistant and anti-salt type polyether sulfonate oil displacement agent and preparation method thereof

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Denomination of invention: A parallel polymer water-based organic pigment dispersant, its preparation and application

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