CN109851800B - Dispersing agent based on rosin derivatives and preparation method thereof - Google Patents
Dispersing agent based on rosin derivatives and preparation method thereof Download PDFInfo
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- CN109851800B CN109851800B CN201811620272.6A CN201811620272A CN109851800B CN 109851800 B CN109851800 B CN 109851800B CN 201811620272 A CN201811620272 A CN 201811620272A CN 109851800 B CN109851800 B CN 109851800B
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Abstract
The invention relates to a dispersing agent based on rosin derivatives and a preparation method thereof, wherein the dispersing agent based on rosin derivatives has a structure represented by the following formula (I), wherein R is1Independently at each occurrence, represents a polyether residue containing a repeating-C-O-structure in the backbone or a polyester residue containing a repeating structure; r2Each occurrence independently represents an amino residue containing an-NH-structure in the backbone. The invention also relates to the branched polymer dispersing assistant and a preparation method thereof, and the application of the dispersing assistant in dispersing granular solids. The branched polymer dispersing aids of the present invention, when dispersing particulate solids, can provide excellent overall dispersing properties to the resulting dispersion.
Description
Technical Field
The invention relates to a dispersant and a preparation method thereof, in particular to a dispersant of a coating ink system containing solid particles and a preparation method thereof, and particularly relates to a dispersant based on rosin derivatives and a preparation method thereof.
Background
The method is widely applied to solid particles as coloring or filling materials in the industries of coatings, adhesives, printing ink, paint, pigments and the like. In particular, particulate solids (e.g., pigments and fillers) are an important component of coatings. They not only impart good hiding power, rich color to the coating, but also provide additional improved physical and chemical properties to the coating composition, including increased chemical resistance and thermal stability. High mechanical forces are required to stabilize the solids for incorporation into the liquid medium. Therefore, dispersants are often used to reduce these dispersing forces, thereby minimizing not only the total energy required to enter the system, but also the dispersing time. Known dispersants are generally surface-active substances which are added in small amounts to the liquid medium and serve to disperse the solid particles.
Patent CN105295500A discloses a paint dispersant, which is prepared from acrylic acid, methyl methacrylate, ethylene glycol, modified diatomite, initiator, sodium sulfite and neutralizing agent, the prepared dispersant can reduce the surface tension of water-based paint, enhance the wetting effect of pigment particles, and make the pigment particles disperse in a liquid phase in a total stable manner, and can be rapidly and firmly combined with the surface groups of the paint, so that the pigment particles are stably suspended in an aqueous solvent, so that the pigment can obtain better dispersion, thereby achieving the best dispersion effect. However, the dispersant has complex reaction in the preparation process, needs to treat diatomite in advance, and has poor dispersibility on certain solid particles. That is, in the present context of large-scale industrial application, the narrow range of existing wetting dispersants has been an obstacle to poor dispersion into solid particle-containing coating ink systems, resulting in coating inks with too high a viscosity, too low a gloss and too high a haze, reducing product quality.
Thus, there is a great need to develop wetting dispersants that exhibit high compatibility with common resin and solvent systems.
Disclosure of Invention
In order to solve the above problems, it is an object of the present invention to provide a rosin derivative-based dispersant for reducing viscosity without adversely affecting glossiness and haze of a coating ink system comprising the wetting dispersant, and a method for preparing the same, particularly a wetting dispersant showing high compatibility with common resin and solvent systems.
One technical scheme of the invention is to provide a rosin derivative-based wetting dispersant which is suitable for use as a wetting dispersant, wherein the wetting dispersant is an addition compound, and the addition compound has the following general formula:
wherein R is1Independently at each occurrence, represents a polyether residue containing a repeating-C-O-structure in the backbone or a polyester residue containing a repeating-COO-structure; r2Each occurrence independently represents an amino residue containing an-NH-structure in the backbone.
Wherein the residue R1And a polyether having a structure represented by the following formula:
wherein R is1Independently at each occurrence, represents C1-C18Alkyl radical, C2-C18Alkenylene radical, C6-C18Aralkyl group; - (CH)2CH2O)m-, wherein m is in the range of 0 to 100; - (CH)2CH2CH2O)n-, wherein n is in the range of 0 to 100; p independently represents an active hydrogen-containing group such as a hydroxyl group, a hydroxymethyl group, a primary amino group, a secondary amino group or the like at each occurrence.
The residue R1In the case of polyester, it has a structure represented by the following formula:
wherein R is2Independently at each occurrence, represents C1-C18Alkyl radical, C2-C18Alkenylene radical, C6-C18Aralkyl group; wherein R is3Independently at each occurrence, represents C1-C18Alkyl radical, C2-C18Alkenylene radical, C6-C18Aralkyl group; wherein m is in the range of 0 to 100.
In another aspect of the invention, a process for preparing the wetting and dispersing agent is provided, wherein polyether or polyester and rosin derivative are subjected to esterification reaction to generate a compound containing dicarboxyl, and then the compound containing amine active hydrogen is subjected to amidation reaction, and the polymer can be used as pigment and filler.
Specifically, the method comprises the following steps:
(i) at least one polyether containing active hydrogen represented by the following formula is provided
Wherein R is1Independently at each occurrence, represents C1-C18Alkyl radical, C2-C18Alkenylene radical, C6-C18Aralkyl group; - (CH)2CH2O)m-, wherein m is in the range of 0 to 100; - (CH)2CH2CH2O)n-, wherein n is in the range of 0 to 100; p independently represents hydroxyl, hydroxymethyl, primary amino, secondary amino and other groups containing active hydrogen at each occurrence;
(ii) or at least one active hydrogen-containing polyester represented by the following formula
Wherein R is2Independently at each occurrence, represents C1-C18Alkyl radical, C2-C18Alkenylene radical, C6-C18Aralkyl group;
wherein R is3Independently at each occurrence, represents C1-C18Alkyl radical, C2-C18Alkenylene radical, C6-C18Aralkyl group;
wherein m is in the range of 0 to 100;
(iii) providing at least one compound containing amine active hydrogen;
(iV) subjecting the polyether or polyester and a rosin derivative to esterification to produce a compound containing a dicarboxyl group, and subjecting the compound containing an amine active hydrogen to amidation to form the dispersant.
In the embodiment of the invention, a catalyst, such as p-toluenesulfonic acid, dibutyltin dilaurate, tetrabutyl titanate, and tetraisobutyl titanate, is required in the esterification reaction process of the polyether or polyester and the rosin derivative.
In an embodiment of the invention, e.g. R1Is polymerized intoEthers in which the polyether residue R1The polyether compound is selected from one of polyethylene glycol monomethyl ether, polyethylene glycol monoethyl ether or polyethylene glycol monobutyl ether with the number average molecular weight of 200-3000 g/mol, also can be selected from one of polypropylene glycol monomethyl ether, polypropylene glycol monoethyl ether or polypropylene glycol monobutyl ether with the number average molecular weight of 200-3000 g/mol, or is selected from random polyether with the number average molecular weight of 200-3000 g/mol, or is selected from monoalkyl polyether amine with the number average molecular weight of 200-2000 g/mol.
In an embodiment of the invention, e.g. R1Is a polyester in which the polyester residue R1The preparation method uses alcohol and lactone as starting materials, and the number average molecular weight of the synthesized polyester is 200-3000 g/mol.
As examples of alcohols, one or more of n-propanol, isopropanol, n-butanol, n-pentanol, n-hexanol, isohexanol, n-heptanol, n-octanol, isooctanol, n-nonanol, or dodecanol may be used. Preferably, n-octanol or dodecanol is used.
As examples of lactones, propiolactone, butyrolactone, delta-valerolactone, epsilon-caprolactone, or C may be used1-8One or more of alkyl substituted epsilon-caprolactone. Preferably, epsilon-caprolactone is used as the lactone.
The esterification reaction of the alcohol and lactone may be carried out under reaction conditions known in the art, for example, may be carried out in the presence of p-toluenesulfonic acid, dibutyltin dilaurate, or tetrabutyl titanate catalyst at a temperature of about 80 ℃ to 180 ℃.
In an embodiment of the invention, the compound containing amine active hydrogen is selected from one or more of monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, polyethylenepolyamine, polyethyleneimine, N-pyrrolidone, 1- (2-hydroxyethyl) piperazine, 2-aminopyridine, 4-aminopyridine, 2-aminoimidazole, 4-aminoimidazole, 1- (3-aminopropyl) imidazole, 1, 3-cyclohexyldimethylamine, diaminodicyclohexylmethane or isophoronediamine.
In an embodiment of the present invention, the rosin derivative refers to maleated rosin or fumaric acid rosin.
In an embodiment of the present invention, the molar equivalent ratio of the polyether or polyester to the rosin derivative is in the range of 1 to 1.2: 1, in the above range.
In an embodiment of the present invention, the molar equivalent ratio of the amine-active hydrogen compound to the rosin derivative is 1 to 1.2: 1, in the above range.
Compared with the prior art, the invention has the advantages that:
the polymer synthesized by the invention takes rosin derivatives as intermediates, long-chain polyether or polyester chain segments are grafted to the intermediates to serve as wetting and steric hindrance chain segments by utilizing the excellent compatibility of the rosin derivatives, meanwhile, the dicarboxyl groups on the rosin derivatives react with amine active hydrogen compounds, and the amino residues and the carboxyl groups are combined and anchored on the surfaces of solid particles after the reaction.
Detailed Description
The present invention provides a polymer prepared by esterification and amidation of a monomer mixture, which is useful as a method for preparing a wetting dispersant for pigments and fillers, and in order to facilitate understanding of the present invention, the present invention will be more fully described with reference to the following examples, of which preferred examples are set forth below. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Optional components not contemplated by the present invention are not contemplated to be excluded from the composition where the composition is described as including or comprising specific components, and the composition is contemplated to be comprised of or consisting of the recited components, or optional process steps not contemplated by the present invention are contemplated to be excluded from the method where the method is described as including or comprising specific process steps, and the method is contemplated to be comprised of or consisting of the recited process steps.
The terms "preferred" and "preferably" refer to embodiments of the invention that may provide certain benefits under certain circumstances. However, other embodiments may be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.
As used herein, "a," "an," "the," "at least one," and "one or more" are used interchangeably. Thus, for example, a dispersion containing "a" particulate solid can be interpreted to mean that the dispersion contains "one or more" particulate solids.
For the sake of brevity, only some numerical ranges are explicitly disclosed herein. However, any lower limit may be combined with any upper limit to form ranges not explicitly recited; and any lower limit may be combined with any other lower limit to form a range not explicitly recited, and similarly any upper limit may be combined with any other upper limit to form a range not explicitly recited. Also, although not explicitly recited, each point or individual value between endpoints of a range is encompassed within the range. Thus, each point or individual value can form a range not explicitly recited as its own lower or upper limit in combination with any other point or individual value or in combination with other lower or upper limits.
The above summary of the present invention is not intended to describe each disclosed embodiment or every implementation of the present invention. The following description more particularly exemplifies illustrative embodiments. At various points throughout this application, guidance is provided through a list of embodiments that can be used in various combinations. In each instance, the list serves only as a representative group and should not be construed as exhaustive.
Examples
The present disclosure is more particularly described in the following examples that are intended as illustrative only since numerous modifications and variations within the scope of the present disclosure will be apparent to those skilled in the art. Unless otherwise stated, all parts, percentages, and ratios reported in the following examples are on a weight basis, and all reagents used in the examples are commercially available and can be used directly without further treatment.
Example 1
Synthesis of polyester segment
Polyester Compound 1
186.33 parts of dodecanol, 1710 parts of epsilon-caprolactone monomer, 1.9 parts of tetrabutyl titanate were added at room temperature to a four-necked flask equipped with a thermometer, overhead stirrer, gas inlet and condenser tube under nitrogen protection and homogenized. The temperature raising means was turned on to set the reaction temperature at 160 ℃ while the stirring was turned on at a stirring speed of 100rpm, and when the reaction mixture reached about 160 ℃, the temperature was maintained and the reaction was terminated after 18 hours, thereby obtaining a polyester compound 1. The number average molecular weight was calculated to be about 1896 g/mol.
Polyester Compound 2
130 parts of isooctanol, 1710 parts of epsilon-caprolactone monomer, and 1.7 parts of tetrabutyltitanate were added at room temperature to a four-necked flask equipped with a thermometer, overhead stirrer, gas inlet, and condenser tube under nitrogen protection and homogenized. The temperature raising means was turned on to set the reaction temperature at 160 ℃ while the stirring was turned on at a stirring speed of 100rpm, and when the reaction mixture reached about 160 ℃, the temperature was maintained and the reaction was terminated after 18 hours, thereby obtaining a polyester compound 2. The number average molecular weight was calculated to be about 1840 g/mol.
Polyester compound 3
130 parts of isooctanol, 2850 parts of epsilon-caprolactone monomer, and 3 parts of tetrabutyltitanate were added at room temperature to a four-necked flask equipped with a thermometer, an overhead stirrer, a gas inlet, and a condenser tube under nitrogen protection and homogenized. The temperature raising means was turned on to set the reaction temperature at 160 ℃ while the stirring was turned on at a stirring speed of 100rpm, and when the reaction mixture reached about 160 ℃, the reaction was maintained at the temperature for 18 hours and then terminated, thereby obtaining a polyester compound 3. The number average molecular weight was calculated to be approximately 2980 g/mol.
Synthesis of rosin derivative-polyether/polyester chain segment
Rosin derivative-polyether/polyester segment 1
Under nitrogen protection, 400 parts of maleated rosin, 1991 parts of polyester compound 1, 4.8 parts of dibutyltin dilaurate were added at room temperature to a four-necked flask equipped with a thermometer, overhead stirrer, gas inlet and condenser tube and homogenized. Starting a temperature raising device, setting the reaction temperature to be 120 ℃, simultaneously starting stirring, setting the stirring speed to be 100rpm, and when the reaction mixture reaches about 120 ℃, maintaining the temperature for reaction for 6 hours, and then terminating the reaction, thereby obtaining the rosin derivative-polyether/polyester chain segment 1. The number average molecular weight was calculated to be about 2296 g/mol.
Rosin derivative-polyether/polyester segment 2
The synthesis of the rosin derivative-polyether/polyester segment 2 was similar to that of the rosin derivative-polyether/polyester segment 1, except that 3129 parts of the polyester compound 3 was used in place of the polyester compound 1, and the number average molecular weight was calculated to be about 3380 g/mol.
Rosin derivative-polyether/polyester segment 3
The synthesis of the rosin derivative-polyether/polyester segment 3 was similar to that of the rosin derivative-polyether/polyester segment 1, except that 1050 parts of polyethylene glycol monomethyl ether (Mn 1000) was used instead of the polyester compound 1, and the number average molecular weight was calculated to be about 1400 g/mol.
Rosin derivative-polyether/polyester segment 4
The synthesis of the rosin derivative-polyether/polyester segment 4 was similar to that of the rosin derivative-polyether/polyester segment 1, except that 2100 parts of polyetheramine M2070(Mn 2000) was used instead of the polyester compound 1, and the number average molecular weight was calculated to be about 2470 g/mol.
Rosin derivative-polyether/polyester segment 5
The synthesis of the rosin derivative-polyether/polyester segment 5 was similar to that of the rosin derivative-polyether/polyester segment 1, except that 420 parts of polypropylene glycol monomethyl ether (Mn ═ 400) was used instead of the polyester compound 1, and the number average molecular weight was calculated to be about 800 g/mol.
Synthesis of dispersants
Dispersant 1
2296 parts of rosin derivative-polyether/polyester segment 1 and 146 parts of triethylenetetramine were added to a four-necked flask equipped with a thermometer, an overhead stirrer, a gas inlet, and a condenser tube with a fractionating device under nitrogen protection, and homogenized. The temperature raising device was started, the reaction temperature was set to 150 ℃, the stirring was started simultaneously, the stirring speed was set to 100rpm, and when the reaction mixture reached about 150 ℃, the reaction was stopped after maintaining the reaction temperature for 4h, thereby obtaining dispersant 1.
Dispersant 2-9
The dispersants 2-9 were prepared similarly to dispersant 1, except that the polyether-ethyl silicate branch and the amine-containing active hydrogen compound were used in different types and in different amounts, as shown in table 1 below.
TABLE 1
Example 2: dispersions of particulate solids and thixotropic properties thereof
The dispersion aids 1, 6, 8 of the present invention (solid content 30%) or the commercially available dispersion aid BYK161 (solid content 30%) in the amounts shown in table 2 below were mixed with a short oil alkyd resin (solid content 60%), colored carbon black FW200 in powder form, propylene glycol methyl ether acetate, respectively, and dispersed in Dispermat with glass beads at 40 ℃ for 1 hour to give dispersions 1,2,3 of particulate solids and a control dispersion.
TABLE 2
Note: the viscosity of the dispersion of particulate solids was measured using a Brookfield LVDV-I Prime viscometer using spindle number 3
The results show that the pigment particle solid dispersion containing the dispersant of the present invention exhibits lower viscosity and thixotropy, exhibiting more excellent dispersibility.
Example 3: dispersion of particulate solids and dispersion stability properties thereof
The 1,2,3 dispersion of example 2 was mixed with NC resin according to dispersion: NC ═ 1:10, mixed homogeneously and applied to BYK-Gardner comparative recording paper in a wet film thickness of 100 μm. After the coating material was dried at room temperature, the gloss of the coating film and the haze of the coating film were measured at a test angle of 60 ° using a gloss-haze tester by BYK-Gardner.
| Product source | Degree of gloss | Turbidity of water |
| Control | 89 | 124 |
| Dispersion 1 | 92 | 85 |
| Dispersion 2 | 93 | 89 |
| Dispersion 3 | 95 | 56 |
The results show that the pigment particle solid dispersion comprising the dispersant of the present invention exhibits higher gloss and lower turbidity, exhibiting more excellent dispersibility.
Claims (5)
1. A wetting and dispersing agent is characterized in that the wetting and dispersing agent is an addition compound and has the following general formula:
wherein R is1Independently at each occurrence, represents a polyether residue containing a repeating-C-O-structure in the backbone or a polyester residue containing a repeating-COO-structure; r2Each occurrence independently represents an amino residue containing an-NH-structure in the backbone;
the preparation method of the wetting dispersant comprises the following steps: firstly, polyether or polyester and rosin derivatives are subjected to esterification reaction to generate a compound containing dicarboxyl, and then the compound containing amine active hydrogen and the amidation reaction are carried out to obtain the modified polyester resin;
the rosin derivative refers to maleated rosin or fumaric acid rosin.
2. Wetting and dispersing agent according to claim 1, characterized in that the polyether residues have a number average molecular weight in the range from 200 to 3000g/mol or the polyester residues have a number average molecular weight in the range from 200 to 3000 g/mol.
3. The wetting and dispersing agent of claim 2, wherein the esterification reaction of the polyether or polyester and the rosin derivative requires a catalyst, and the catalyst is one or more selected from p-toluenesulfonic acid, dibutyltin dilaurate, tetrabutyl titanate and tetraisobutyl titanate.
4. The wetting and dispersing agent of claim 3, wherein the amine active hydrogen containing compound is selected from one or more of monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, polyethylenepolyamine, polyethyleneimine, 2-aminopyridine, 4-aminopyridine, 2-aminoimidazole, 4-aminoimidazole, 1- (3-aminopropyl) imidazole, 1, 3-cyclohexyldimethylamine, diaminodicyclohexylmethane or isophoronediamine.
5. The wetting and dispersing agent of any of claims 3 to 4, wherein the molar equivalent ratio of the polyether or polyester to the rosin derivative is 1 to 1.2: 1, the molar equivalent ratio of the amine-active hydrogen compound to the rosin derivative is 1-1.2: 1.
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| US5066331A (en) * | 1989-12-21 | 1991-11-19 | Westvaco Corporation | Water-soluble rosin polyamide resins |
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| JP2014005342A (en) * | 2012-06-22 | 2014-01-16 | Fujifilm Corp | Resin and process for producing the same, and toner using the same |
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