CN109679398B - Hyper-dispersant for polyurethane-based water-based paint and preparation method thereof - Google Patents

Hyper-dispersant for polyurethane-based water-based paint and preparation method thereof Download PDF

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CN109679398B
CN109679398B CN201811539902.7A CN201811539902A CN109679398B CN 109679398 B CN109679398 B CN 109679398B CN 201811539902 A CN201811539902 A CN 201811539902A CN 109679398 B CN109679398 B CN 109679398B
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朱祥
郁金华
张晓明
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LIWANG (JIANGSU) Co.,Ltd.
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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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/65—Additives macromolecular
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3857—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur

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Abstract

The invention discloses a hyper-dispersant for polyurethane-based water-based paint and a preparation method thereof, wherein the preparation method of the hyper-dispersant for the water-based paint comprises the following steps: cyanuric chloride is first reacted with sulfamic acid compound or hydroxy sulfonic acid compound, then reacted with dihydric alcohol or alcohol ammonia compound to produce dihydric alcohol intermediate containing sulfonic acid group, and finally reacted with diisocyanate and dihydric alcohol compound in solvent to produce polyurethane base hyperdispersant. The polyurethane-based hyper-dispersant prepared by the invention can be used for high-solid-content water-based paint, and has good fluidity, high stability and bright color; the hyper-dispersant of the invention has cheap and easily obtained raw materials, simple preparation process, reaction which can be carried out at lower temperature and no waste water and gas emission.

Description

Hyper-dispersant for polyurethane-based water-based paint and preparation method thereof
Technical Field
The invention belongs to the field of coating chemical industry, and particularly relates to a hyperdispersant for a polyurethane-based water-based coating and a preparation method thereof.
Background
The coating is a fine chemical product which is coated on the surface of an object by a specific construction method and then is cured to form a continuous protective film with certain strength on the surface of the object or form a coating film with a certain special function.
The coating generally consists of a film-forming material, a solvent, a pigment and an auxiliary agent. The film forming material is also called as base material, and is the main material which can make the paint firmly adhere to the surface of the coated object to form a continuous film; the solvent is a volatile component and mainly comprises an organic solvent and water; pigments are insoluble fine particles dispersed in paints and can be classified into coloring pigments and extender pigments, mainly used for coloring, providing protection, decoration and reducing cost; the proportion of auxiliaries in the coating formulation is small, but plays a critical role. The storage, construction, film forming and tolerance performance of the auxiliary coating play the most important roles. Common auxiliaries in coatings are: leveling agent, thickening agent, surfactant, pigment dispersing agent, plasticizer, drier, curing agent, bactericide, mildew preventive and the like.
Pigment dispersants also serve as wetting dispersants, and the commonly used pigment dispersants mainly include inorganic dispersants, surfactants and polymers, and preferably polymers, so the polymer dispersants are also called as hyperdispersants. The polymer comprises natural polymer, and is mainly used for solvent paint; examples of the synthetic polymer include polycarboxylate, polyacrylate, polymethacrylate, maleic acid-isobutylene (or styrene) copolymer salt, polyvinylpyrrolidone, polyether derivative, and the like.
In patent CN2008102009611, a dispersant for pigment based on salicylic acid derivative and a preparation method and application thereof are introduced; patent CN201110235613X introduces a dispersing agent and a preparation method thereof, the method adopts cardanol and styrene oxide to open ring and polymerize under the action of sodium alkoxide, an intermediate product is obtained and then polymerized with ethylene oxide, and the hyper-dispersing agent for pigment is prepared; patent CN2012105602412 discloses an aqueous pigment dispersant obtained by further polycondensation based on a product of reaction of malic acid with polyethylene oxide. Patent CN2007100241525 introduces a hyperbranched non-ionic water-based dispersant which takes methyl n-butanone as a solvent and various diisocyanates, branched polyester and polyether as raw materials; patent CN2005800303658 describes a dispersant prepared by radical copolymerization of itaconic acid, polyoxyethylene ester of citric acid and (meth) acrylic acid as raw materials, but the dispersant is mainly used in the fields of cement dispersion and concrete water reducing agent; patent CN2007100241525 introduces a preparation method of hyperbranched non-ionic dispersant, and the raw materials used in the preparation method are hyperbranched polyester, diisocyanate compound, polyether and the like;
CN201080054508 introduces a preparation method of a cationic water-based paint dispersant. The concrete method is that polyacrylic acid-maleic acid copolymer reacts with hydrophilic primary amine to prepare the acrylic acid-maleic acid copolymer; CN201110119702.8 reports a preparation method of a water-based paint dispersion obtained by copolymerizing monomers such as acrylic acid, methacrylic acid, sodium methacrylate, 2-acrylamide-2-methylpropanesulfonic acid and the like; CN2007800190165 reports the use of various unsaturated monomers, such as: the nonionic water-based paint dispersant is obtained by free radical copolymerization of maleic polyether monoester, acrylic acid, maleic anhydride and the like.
Patent 201511016207.9 describes a hyperdispersant for aqueous pigment pastes prepared with epoxy resins, alkylol amines and phosphorus oxychloride.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the hyperdispersant for the polyurethane-based water-based paint and the preparation method thereof, and the water-based paint prepared by adopting the hyperdispersant has high solid content, good fluidity, high stability and bright color; the raw materials of the product are cheap and easy to obtain, the preparation process is simple, the reaction can be carried out at a lower temperature, and no waste water or waste gas is basically discharged.
The invention is realized by the following technical scheme:
a hyperdispersant for polyurethane-based waterborne coatings is prepared from the following raw materials: the composition comprises trichloro-sym-triazine, a sulfonic acid compound, a diisocyanate compound, a diol compound and an alcohol amine compound, wherein the molar ratio of the trichloro-sym-triazine to the sulfonic acid compound is 1.
Further, the sulfonic acid compound is an aminosulfonic acid compound or a hydroxysulfonic acid compound; the sulfamic acid compound comprises aminoethyl sulfonic acid and 3-aminopropanesulfonic acid; the hydroxysulfonic acid compound comprises hydroxyethanesulfonic acid and 3-hydroxypropanesulfonic acid.
Further, the diisocyanate compound is toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate or hexamethylene diisocyanate.
Further, the diol compound is ethylene glycol, 1, 3-propanediol, 1, 2-propanediol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 4-cyclohexanedimethanol, or neopentyl glycol.
Further, the alcohol amine compound is methanolamine, ethanolamine, n-propanolamine or n-butanolamine.
A preparation method of a hyperdispersant for a polyurethane-based water-based paint comprises the following steps:
step 1) reacting trichloro-s-triazine with a sulfonic acid compound in a solvent to prepare a 2-substituted-4, 6-dichloro-s-triazine compound serving as an intermediate I;
step 2) reacting the intermediate I in the step 1) with a dihydric alcohol compound or an alcohol amine compound in a solvent to prepare a dihydroxy compound serving as an intermediate II;
and 3) reacting the intermediate II in the step 2) with a diisocyanate compound and a diol compound in a solvent by using dibutyltin dilaurate, and finally generating the hyper-dispersant for the polyurethane-based water-based paint.
Further, the solvent in the step 1) is water, acetonitrile, acetone, 1, 4-dioxane, N-dimethylformamide, tetrahydrofuran or N, N-dimethylacetamide; the solvent in the step 2) is acetonitrile, acetone, 1, 4-dioxane, N-dimethylformamide, tetrahydrofuran or N, N-dimethylacetamide; the solvent in the step 3) is acetonitrile, acetone, 1, 4-dioxane, ethyl acetate, N-dimethylformamide, tetrahydrofuran or N, N-dimethylacetamide.
Further, in the step 2), the molar ratio of the intermediate I to the diol compound or the alcohol amine compound is 1; amount of substance of diisocyanate compound in step 3): (amount of substance of intermediate ii + amount of substance of diol compound) =1 to 1.
Further, the reaction temperature of the step 1) is 0-5 ℃; the reaction temperature of the step 2) is 30-95 ℃.
The invention has the following beneficial effects:
the polyurethane resin is used as a hydrophobic part, and the structures of polyaminomethyl ester and s-triazine in the polyurethane resin can provide enough anchor points to be combined with pigment particles, so that sulfonic groups on side chains are further used as water-soluble groups to improve the hydrophilic capability of macromolecules, and in addition, the sulfonic groups are used as hydrophilic groups to improve the pH value resistance of the dispersing agent. The water-based paint prepared by adopting the dispersant has high solid content, good fluidity, high stability and bright color; the product has the advantages of cheap and easily obtained raw materials, simple preparation process, reaction at a lower temperature and basically no waste water and waste gas emission.
Detailed Description
The invention will be further illustrated with reference to the following examples, but the invention is not limited thereto.
The raw materials of the hyperdispersant for the polyurethane-based water-based paint comprise trichloro-s-triazine, a sulfonic acid compound (a sulfamic acid compound or a hydroxysulfonic acid compound), a diisocyanate compound, a diol compound and an alcohol amine compound.
The preparation method comprises the following steps:
the first step is as follows: in a solvent, trichloro-sym-triazine (cyanuric chloride) reacts with sulfamic acid compound or hydroxysulfonic acid compound and the like to prepare 2-substituted-4, 6-dichloro-sym-triazine compound serving as an intermediate I, and the reaction formula is as follows:
Figure GDA0004021705570000041
in the formula: m is O or NH; n is 2 or 3.
The second step is that: the intermediate I reacts with methanolamine, ethanolamine, n-propanolamine, ethylene glycol, propylene glycol, 1, 4-cyclohexanedimethanol and the like in a solvent at the temperature of 30-90 ℃ to generate a dihydroxy compound serving as an intermediate II, and the reaction formula is as follows:
Figure GDA0004021705570000042
in the formula: m is O or NH; m is 1,2, 3 or 4; n is 2 or 3;
r is-OCH 2 CH 2 -，-OCH 2 CH 2 CH 2 -，
Figure GDA0004021705570000043
-NHCH 2 -，-NHCH 2 CH 2 -，-NHCH 2 CH 2 CH 2 -。
The third step: intermediate II and diisocyanate compound (OCN-R) 2 -NCO), diol compound (HO-R) 3 -OH) or the like in a solvent with dibutyltin dilaurate to form a polyurethane-based hyperdispersant, according to the following reaction scheme:
Figure GDA0004021705570000044
Figure GDA0004021705570000051
in the formula: m is O or NH; m is 1,2, 3 or 4; n is 2 or 3;
r is-OCH 2 CH 2 -，-OCH 2 CH 2 CH 2 -，
Figure GDA0004021705570000052
-NHCH 2 -，-NHCH 2 CH 2 -，-NHCH 2 CH 2 CH 2 -；
OCN-R 2 -NCO is: toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate;
HO-R 3 -OH is: ethylene glycol, 1, 3-propanediol, 1, 2-propanediol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 4-cyclohexanedimethanol, neopentyl glycol.
In the first reaction, the solvent may be water, acetonitrile, acetone, 1, 4-dioxane, N-Dimethylformamide (DMF), tetrahydrofuran (THF), N-Dimethylacetamide (DMAC), or the like.
The temperature of the first step reaction is 0-5 ℃.
The molar ratio of the trichloro-s-triazine to the sulfamic acid compound or the hydroxysulfonic acid compound in the first-step reaction is 1.
In the second reaction, the solvent may be acetonitrile, acetone, 1, 4-dioxane, N-Dimethylformamide (DMF), tetrahydrofuran (THF), N-Dimethylacetamide (DMAC), or the like.
The temperature of the second step reaction is 30-95 ℃.
In the second step of reaction, the molar ratio of the intermediate I to methanolamine, ethanolamine, n-propanolamine, ethylene glycol, propylene glycol and 1, 4-cyclohexanedimethanol is 1.
In the third reaction, the solvent may be acetonitrile, acetone, 1, 4-dioxane, ethyl acetate, N-Dimethylformamide (DMF), tetrahydrofuran (THF), N-Dimethylacetamide (DMAC), or the like.
In the third reaction step, the amount of diisocyanate compound: (amount of substance of intermediate ii + amount of substance of diol compound) =1 to 1.
Example 1
(1) 0.1mol of 3-hydroxypropanesulfonic acid was neutralized with sodium hydroxide to prepare sodium 3-hydroxypropanesulfonate solid powder. Adding 300mL of acetonitrile and 0.1mol of cyanuric chloride into a four-neck flask, cooling an ice salt bath to 5 ℃, stirring while slowly adding 3-hydroxypropanesulfonic acid sodium in batches, controlling the pH of a reaction system to be =9 by using a small amount of acetonitrile solution of triethylamine, and finishing the reaction after 3 hours to obtain the acetonitrile solution of an intermediate I. The intermediate I (1) has the following structural formula:
Figure GDA0004021705570000061
(2) Adding 0.2mol of ethanolamine into acetonitrile solution (30 mL) containing 0.1mol of the intermediate I (1), heating to 30 ℃, reacting for 2h, continuously heating to 80 ℃, and reacting for 3h to obtain the acetonitrile solution of the intermediate II. The intermediate II (1) has the following structural formula:
Figure GDA0004021705570000062
(3) Adding 0.15mol of isophorone diisocyanate and 0.1mol of ethylene glycol into an acetonitrile solution (60 mL) containing 0.05mol of the intermediate II (1), adding a few drops of dibutyltin dilaurate, stirring, heating to 80 ℃, reacting for 3 hours, and then removing acetonitrile by rotary evaporation to obtain solid powder of the polyurethane-based hyper-dispersant 1, wherein the structural formula is as follows:
Figure GDA0004021705570000063
example 2
(1) 0.1mol of isethionic acid was neutralized with sodium hydroxide to prepare sodium isethionate solid powder. Adding 100ml of DMF and 0.1mol of cyanuric chloride into a four-neck flask, cooling to 5 ℃ in an ice salt bath, slowly adding sodium hydroxyethanesulfonate in batches while stirring, controlling the pH of a reaction system to be =9 by using a small amount of DMF solution of triethylamine, and finishing the reaction after 3 hours to obtain the DMF solution of the intermediate I. The intermediate I (2) has the following structural formula:
Figure GDA0004021705570000071
(2) Adding 0.2mol of n-propanolamine into the DMF solution containing 0.1mol of the intermediate I (2), heating to 20 ℃, reacting for 2 hours, continuously heating to 90 ℃, and reacting for 3 hours to obtain the DMF solution of the intermediate II (2). Intermediate II (2) has the following structural formula:
Figure GDA0004021705570000072
(3) Adding 0.15mol of diphenylmethane diisocyanate and 0.1mol of 1, 3-propanediol into a DMF solution (60 mL) containing 0.2mol of the intermediate II (2), adding a few drops of dibutyltin dilaurate, stirring, heating to 80 ℃, reacting for 3 hours, and performing rotary evaporation to remove DMF to obtain solid powder of the polyurethane-based hyperdispersant 2, wherein the structural formula is as follows:
Figure GDA0004021705570000073
example 3
The procedure was as in example 2. The first step adopts 3-aminopropanesulfonic acid as a raw material and 1, 4-dioxane as a reaction solvent to obtain an intermediate I (3), wherein the reaction temperature is 0 ℃; the second step reaction medicine is 1, 4-cyclohexanedimethanol, the reaction solvent is 1, 4-dioxane, the molar ratio of the intermediate I (3) to the 1, 4-cyclohexanedimethanol is 1; the third step reaction medicine is hexamethylene diisocyanate (0.5 mol), the second step reaction product intermediate II (3) (0.3 mol) and 1, 4-cyclohexanedimethanol (0.3 mol), the reaction solvent is 1, 4-dioxane (500 mL), the reaction temperature is 80 ℃, and the final product is polyurethane-based hyperdispersant 3, and the structural formula is as follows:
Figure GDA0004021705570000081
example 4
The procedure was as in example 2. The first step adopts 3-hydroxy propanesulfonic acid as raw material, acetone as reaction solvent and intermediate I (1) as reaction product; the second step is that 1, 2-propylene glycol is used as a reaction medicine, acetone is used as a reaction solvent, the molar ratio of the intermediate I (1) to the 1, 2-propylene glycol is 1; in the third step, the reaction chemicals are toluene diisocyanate (1 mol), intermediate II (4) (1 mol) and 1, 2-propylene glycol (0.7 mol), the reaction solvent is acetone, the reaction temperature is 80 ℃, and the final product is polyurethane-based hyper-dispersant 4, and the structural formula is as follows:
Figure GDA0004021705570000082
example 5
The procedure was as in example 2. The first step adopts 3-aminopropanesulfonic acid as a raw material, water as a reaction solvent, the reaction temperature is 0 ℃, and after the first step reaction is finished, water is removed by reduced pressure evaporation to obtain an intermediate I (3); in the second step, 1, 3-propylene glycol is used as a reaction medicine, and DMAC is used as a reaction solvent to obtain an intermediate II (5); in the third step, the reactants are isophorone diisocyanate (0.2 mol), intermediate II (5) (0.15 mol) and neopentyl glycol (0.15 mol), the reaction solvent is DMAC (200 mL), and the final product is polyurethane-based hyperdispersant 5.
Figure GDA0004021705570000091
Example 6
The procedure was as in example 2. The first step adopts 3-hydroxypropanesulfonic acid as a raw material, DMAC as a reaction solvent, and the reaction temperature is 5 ℃ to obtain an intermediate I (1); in the second step, 1, 2-propylene glycol is used as a reaction medicine, acetone is used as a reaction solvent, and the reaction is carried out for 3 hours at the temperature of 90 ℃ to obtain an intermediate II (6); the third step is that the reaction medicine is toluene diisocyanate (0.7 mol), intermediate II (6) (0.3 mol) and 1, 4-cyclohexanedimethanol (0.4 mol), the reaction solvent is acetone (300 mL), and the final product is polyurethane-based hyper-dispersant 6.
Example 7
The procedure was as in example 2. The first step of operation adopts 2-hydroxyethanesulfonic acid as a raw material and THF as a reaction solvent to obtain an intermediate I (2); the second step is that 1, 4-cyclohexanedimethanol is used as a reaction medicine, and THF is used as a reaction solvent to obtain an intermediate II (7); in the third step, hexamethylene diisocyanate (1.2 mol), intermediate II (7) (1 mol) and 1, 5-pentanediol (1 mol) are used as reaction products, THF is used as a reaction solvent, and the final product is polyurethane-based hyper-dispersant 7.
Example 8
The procedure was as in example 2. The first step adopts 2-hydroxyethanesulfonic acid as a raw material and DMF as a reaction solvent to obtain an intermediate I (2); in the second step, n-propanolamine is used as a reaction medicine, DMF is used as a reaction solvent, and the reaction is carried out for 5 hours at 40 ℃ to obtain an intermediate II (2); in the third step, the reactants are toluene diisocyanate (1 mol), intermediate II (2) (0.8 mol) and 1, 6-hexanediol (0.6 mol), the reaction solvent is DMF (200 mL), the reaction temperature is 90 ℃, and the final product is polyurethane-based hyper-dispersant 8.
Example 9
The procedure was as in example 2. The first step adopts 2-aminoethanesulfonic acid as raw material, water as reaction solvent, the reaction is carried out for 2h at 0 ℃, and after the first step reaction is finished, water is removed by reduced pressure evaporation to obtain an intermediate I (9); secondly, reacting 2mol of methanolamine and 1mol of intermediate I (9) with acetone as a reaction solvent at 30 ℃ for 3 hours to obtain an intermediate II (9); in the third step, the reactants are diphenylmethane diisocyanate (0.1 mol), intermediate II (9) (0.05 mol) and 1, 3-propylene glycol (0.075 mol), the reaction solvent is acetone, the reaction temperature is 70 ℃, and the final product is polyurethane-based hyper-dispersant 9.
Example 10
The procedure was as in example 2. The first step adopts 3-hydroxy propanesulfonic acid as raw material and 1, 4-dioxane as reaction solvent; in the second step, ethanolamine is used as a reaction medicine, and DMAC is used as a reaction solvent; the third step is that the reaction medicine is isophorone diisocyanate (3 mol), the second step product (2.5 mol) and 1, 2-propylene glycol (1.5 mol), the reaction solvent is acetone (2000 mL), the reaction temperature is 75 ℃, and the final product is polyurethane-based hyper-dispersant 10.
Test example 1
The prepared waterborne polyurethane-based hyper-dispersant, organic pigment and water are weighed according to the proportion in the table 1, added into a shaking cup and mixed evenly, and shaken on a shaker for 3 hours at room temperature, and then the viscosity performance parameters of the sample are detected, and the test results are shown in the table 2.
TABLE 1 Hyperdispersant test formulation
Figure GDA0004021705570000101
TABLE 2 viscosity of the Wash pastes prepared from Hyperdispersants (25 ℃ C.)
Figure GDA0004021705570000102

Claims (5)

1. The hyperdispersant for the polyurethane-based water-based paint is characterized by being prepared from the following raw materials: the composition comprises trichloro-s-triazine, a sulfonic acid compound, a diisocyanate compound, a diol compound and an alcohol amine compound, wherein the molar ratio of the trichloro-s-triazine to the sulfonic acid compound is 1;
the sulfonic acid compound is an aminosulfonic acid compound or a hydroxysulfonic acid compound; the sulfamic acid compound comprises aminoethanesulfonic acid and 3-aminopropanesulfonic acid; the hydroxysulfonic acid compound comprises hydroxyethanesulfonic acid and 3-hydroxypropanesulfonic acid;
the diisocyanate compound is toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate or hexamethylene diisocyanate;
the diol compound is ethylene glycol, 1, 3-propylene glycol, 1, 2-propylene glycol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 4-cyclohexanedimethanol or neopentyl glycol;
the alcohol amine compound is methanolamine, ethanolamine, n-propanolamine or n-butanolamine.
2. The method for preparing a hyperdispersant for a polyurethane-based waterborne coating according to claim 1, comprising the steps of:
step 1): in a solvent, trichloro-sym-triazine reacts with a sulfonic acid compound to prepare a 2-substituted-4, 6-dichloro-sym-triazine compound serving as an intermediate I;
step 2): reacting the intermediate I in the step 1) with an alcohol amine compound in a solvent to prepare a dihydroxy compound serving as an intermediate II;
and step 3): and 2) adding dibutyltin dilaurate into the intermediate II, a diisocyanate compound and a diol compound in a solvent for reaction, and finally generating the hyper-dispersant for the polyurethane-based water-based paint.
3. The method for preparing a hyperdispersant for polyurethane-based waterborne coatings according to claim 2, wherein the solvent of step 1) is water, acetonitrile, acetone, 1, 4-dioxane, N-dimethylformamide, tetrahydrofuran or N, N-dimethylacetamide;
the solvent in the step 2) is acetonitrile, acetone, 1, 4-dioxane, N-dimethylformamide, tetrahydrofuran or N, N-dimethylacetamide;
the solvent in the step 3) is acetonitrile, acetone, 1, 4-dioxane, ethyl acetate, N-dimethylformamide, tetrahydrofuran or N, N-dimethylacetamide.
4. The process for preparing a hyperdispersant for polyurethane-based waterborne coatings according to claim 2, wherein in step 2), the amount of intermediate i material: the mass of the alcohol amine compound is 1; amount of diisocyanate compound in step 3): the mass of the intermediate II + the mass of the diol compound is 1 to 1.
5. The method of producing a hyperdispersant for a polyurethane-based water-based paint according to claim 2, wherein the reaction temperature in the step 1) is from 0 to 5 ℃; the reaction temperature in the step 2) is 30 to 95 ℃.
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CN1343666A (en) * 2000-09-21 2002-04-10 王建国 Monochloro-sym-triazine derivative and its application
CN105949349A (en) * 2016-05-11 2016-09-21 南京晓庄学院 Chitosan-based hyperdispersant and preparation method thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1310205A (en) * 2000-01-20 2001-08-29 大日精化工业株式会社 Pigment dispersing agent and pigment composition containing the same dispersing agent
CN1343666A (en) * 2000-09-21 2002-04-10 王建国 Monochloro-sym-triazine derivative and its application
CN105949349A (en) * 2016-05-11 2016-09-21 南京晓庄学院 Chitosan-based hyperdispersant and preparation method thereof

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