CN114591514A - Environment-friendly lignin-based dispersant for azo pigment and preparation method thereof - Google Patents
Environment-friendly lignin-based dispersant for azo pigment and preparation method thereof Download PDFInfo
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- CN114591514A CN114591514A CN202210313098.0A CN202210313098A CN114591514A CN 114591514 A CN114591514 A CN 114591514A CN 202210313098 A CN202210313098 A CN 202210313098A CN 114591514 A CN114591514 A CN 114591514A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0066—Aqueous dispersions of pigments containing only dispersing agents
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0091—Process features in the making of dispersions, e.g. ultrasonics
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Abstract
The invention discloses an environment-friendly lignin-based dispersing agent for azo pigments and a preparation method thereof, wherein enzymatic hydrolysis lignin is dissolved in a sodium hydroxide aqueous solution, histidine and formaldehyde with different proportions are added, after a reaction is carried out for a period of time under stirring at a certain temperature, the pH of a reaction solution is adjusted to be neutral, dialysis and freeze drying are carried out to obtain brown histidine modified lignin, a certain mass of histidine modified lignin and a certain mass of azo pigments are weighed, added into a container, water is added to fully wet the organic pigments, then a certain amount of histidine modified lignin is added, and after the pH value is adjusted, a cell crusher is utilized to carry out ultrasonic dispersion for a certain period of time under a certain power to obtain the final pigment dispersion liquid. The biomass resource lignin with rich sources and low price is used as the raw material, so that the production cost is reduced, the resource utilization of the lignin is realized, the waste is changed into valuable, and the biomass resource lignin has important social, economic and ecological significance.
Description
Technical Field
The invention belongs to the field of fine chemical engineering, and particularly relates to an environment-friendly lignin-based dispersing agent for azo pigments and a preparation method thereof.
Background
With the development of industry and the improvement of living standard, pigments are increasingly applied to the fields of coatings, inks, rubbers, plastics, printing and the like to impart better appearance effects. Among them, organic pigments are widely used in high-grade paints in the automotive and construction industries because of their more vivid colors, high tinting strength, and good light and weather resistance. However, organic pigment molecules generally have low polarity and strong hydrophobicity, are difficult to dissolve in water and other media, and are extremely prone to agglomeration between particles, which may cause defects such as pigment flocculation, light loss, color shift, flooding/blooming, precipitation, and the like. Therefore, designing to prepare highly efficient dispersants has been a focus of research in the pigment industry.
The traditional pigment dispersing agents are divided into inorganic dispersing agents and organic small molecule dispersing agents, and the effective dispersing and stabilizing effects are achieved mainly through an electrostatic repulsion stabilizing mechanism. However, they have low adsorptive strength on the surface of the pigment particles and are easily detached from the surface of the pigment, resulting in re-flocculation or agglomeration of the pigment particles. In recent years, a polymeric dispersant, also called a hyperdispersant, provides a high steric hindrance effect, so that pigment particles form an effective dispersion stable state, and the system has low sensitivity to temperature, pH value and the like, and is an ideal dispersant. At present, the commercial polymeric dispersants mainly include Solsperse series of ICI company in UK, Disperse-AYD series of Daniel company in America, Disperse BYK series of Bick chemical company in Germany, Hyersol series of KVK company in Denmark, NBZ-3 in China, and the like. Although they exhibit good dispersion, their raw materials are all derived from non-renewable fossil-based raw materials, and do not meet today's green sustainable development strategy. Therefore, the preparation of the efficient and green hyper-dispersant by taking renewable biomass resources as raw materials becomes a research hotspot of the pigment industry.
Lignin is the most abundant renewable aromatic polymer on earth, second only to cellulose. Compared with other biomass molecules, lignin molecules have a plurality of carboxyl groups, hydroxyl groups, benzene rings and the like, can be used as anchoring groups, and form close adsorption on the surface of the pigment through Van der Waals force, hydrogen bonds, pi-pi bonds and the like; secondly, the specific three-dimensional network structure of the lignin molecule can provide stronger steric hindrance effect, and can effectively prevent secondary aggregation of the pigment; in addition, the polyphenol structure and the aromatic skeleton in the lignin molecules can endow the pigment with good ultraviolet oxidation resistance. Therefore, the efficient and green biomass-based hyperdispersant prepared by taking the industrial lignin as the raw material has wide market prospect.
Disclosure of Invention
Based on the problems, different numbers of histidine molecules are controllably grafted on the ortho position of the phenolic hydroxyl group through a Mannich reaction, more carboxyl groups and nitrogen-containing heterocycles are introduced while the water solubility of the histidine molecules is regulated, the interaction between the lignin-based dispersing agent and the pigment is further improved, the key technical problem of poor dispersibility of the industrial lignin due to low water solubility is solved, and the pigment is endowed with excellent ultraviolet oxidation resistance.
The invention provides a preparation method of an environment-friendly lignin-based dispersing agent for azo pigments, which is characterized by comprising the following steps: dissolving enzymatic hydrolysis lignin in sodium hydroxide aqueous solution, adding histidine and formaldehyde in different proportions, stirring and reacting for a period of time at a certain temperature, adjusting the pH of the reaction solution to be neutral, dialyzing, and freeze-drying to obtain brown histidine modified lignin.
Preferably, the mass feed ratio of the lignin, the histidine and the formaldehyde is 1: 0.5-2: 0.5-2.
Preferably, the concentration of the sodium hydroxide aqueous solution is 0.5-1.5 mol/mL.
Preferably, the concentration of the enzymatic hydrolysis lignin solution is 5-15 wt%.
Preferably, the reaction temperature is 40-80 ℃, and the reaction time is 2-6 h.
Preferably, the concentration of the enzymatic hydrolysis lignin solution is preferably 5 wt%, 10 wt% and 15 wt%, the concentration of the sodium hydroxide aqueous solution is preferably 0.5mol/mL, 1mol/mL and 1.5mol/mL, the mass feed ratio of the lignin, the histidine and the formaldehyde is preferably 1: 0.5: 0.5, 1: 1.0: 1.0, 1: 1.5: 1.5, 1: 2.0: 2.0, the reaction temperature is preferably 40 ℃, 60 ℃ and 80 ℃, and the reaction time is preferably 2h, 4h and 6 h.
An environmentally friendly lignin-based dispersant for azo pigments, prepared according to any one of the methods.
Preferably, the use method is as follows: weighing a certain mass of the histidine-modified lignin and a certain mass of azo pigment, adding the azo pigment into a container, adding water to fully wet the organic pigment, then adding a certain amount of histidine-modified lignin, adjusting the pH value, and performing ultrasonic dispersion for a certain time by using a cell crusher under a certain power to obtain the final pigment dispersion liquid.
Preferably, the mass ratio of the histidine modified lignin for wetting to the azo pigment is 1: 2-16.
Preferably, the organic pigment wetting method comprises one or more of magnetic stirring, constant temperature oscillation, high speed shearing and cell crusher ultrasound.
Preferably, the mass ratio of the histidine-modified lignin to the azo pigment added after the pigment is wetted is 0.05-0.6: 1.
Preferably, the mass of the histidine modified lignin for wetting is preferably 50mg, 60mg, 70mg and 80mg, the mass of the azo pigment is preferably 200mg, 300mg, 500mg and 800mg, the organic pigment wetting method comprises magnetic stirring, constant temperature oscillation, high speed shearing and cell crusher ultrasound, the magnetic stirring speed is preferably 500rpm,800rpm and 1000rpm, the magnetic stirring wetting time is preferably 6h, 12h, 18h and 24h, the constant temperature oscillation speed is preferably 90rpm, 150rpm and 210rpm, the constant temperature oscillation temperature is preferably 25 ℃, 40 ℃ and 60 ℃, the constant temperature oscillation wetting time is preferably 12h, 18h and 24h, the high speed shearing speed is preferably 10000rpm, 16000rpm and 22000rpm, the high speed shearing speed wetting time is preferably 1min, 2min and 4min, and the cell crusher ultrasound power is preferably 100W, 170W, 340W and 510W, and the ultrasonic wetting time of the cell crusher is preferably 5min, 8min and 12 min.
Preferably, the mass of the histidine-modified lignin added after wetting is preferably 40mg, 60mg, 80mg, 100mg and 120mg, the pH value is preferably 4, 5, 6 and 7, the ultrasonic power of the cell crusher is preferably 340W, 510W and 680W, and the ultrasonic wetting time of the cell crusher is preferably 10min, 15min and 20 min.
The invention also carries out the dispersion performance test of the histidine modified lignin, which comprises the following steps:
and (3) diluting the color paste by about 10,000 times through the nanometer granularity, and placing a certain amount of diluent in a cuvette to test the particle size and the particle size distribution of the pigment. The measurement results are the average particle size based on light intensity, and each sample was measured 3 times to calculate the average particle size and polydispersity index. And further characterizing the dispersion degree of the particles by a TEM (transmission electron microscope), diluting the color paste by about 5 times, taking a small amount of diluted liquid to drop on the surface of a copper mesh for testing, wherein the magnification times are 15000, 25000 and 50000 times respectively.
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. the biomass resource lignin with rich sources and low price is used as the raw material, so that the production cost is reduced, the resource utilization of the lignin is realized, the waste is changed into valuable, and the biomass resource lignin has important social, economic and ecological significance.
2. Histidine molecules are controllably grafted on the ortho position of the phenolic hydroxyl, more carboxyl groups and nitrogen-containing heterocycles are introduced while the water solubility of the histidine molecules is regulated, and the dispersion activity of the lignin molecules is further improved.
3. Due to the ultraviolet resistance, oxidation resistance and other properties of the lignin, the pigment can be endowed with certain sun resistance and oxidation stability, and the service durability of the pigment is improved.
4. The lignin-based pigment dispersant is derived from plants, is green, safe and nontoxic, and can be widely popularized in multifunctional green additives.
Drawings
FIG. 1 is a graph showing the appearance of dispersed pigments;
FIG. 2 is a scheme of histidine-modified lignin synthesis;
FIG. 3 is a distribution diagram of the particle size of the dispersed pigment;
FIG. 4 is a TEM image of a dispersed pigment.
Detailed Description
It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, 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.
According to the invention, through a Mannich reaction, different numbers of histidine molecules are controllably grafted on the ortho position of the phenolic hydroxyl group, more carboxyl groups and nitrogen-containing heterocycles are introduced while the water solubility of the histidine molecules is regulated, the interaction between the lignin-based dispersing agent and the pigment is further improved, the key technical problem of poor dispersibility of the industrial lignin due to low water solubility is solved, and the pigment is endowed with excellent ultraviolet oxidation resistance.
The materials referred to in the following examples are commercially available.
Example 1
Dissolving enzymatic hydrolysis lignin in a sodium hydroxide aqueous solution according to the proportion of 1: 0.5: 0.5, 1: 1.0: 1.0, 1: 1.5: 1.5 and 1: 2.0: adding lignin, histidine and formaldehyde at a feed ratio of 2.0, stirring at 60 ℃ for reaction for 4h, adjusting the pH of the reaction solution to be neutral by using hydrochloric acid, dialyzing, and freeze-drying to obtain brown histidine-modified lignin.
Example 2
Dissolving enzymatic hydrolysis lignin in a sodium hydroxide aqueous solution according to the proportion of 1: 1.5: adding lignin, histidine and formaldehyde according to the feeding ratio of 1.5, stirring and reacting at 40 ℃, 60 ℃ and 80 ℃ for 4 hours, adjusting the pH of the reaction solution to be neutral by using hydrochloric acid, dialyzing, and freeze-drying to obtain brown histidine modified lignin.
Example 3
Dissolving enzymatic hydrolysis lignin in a sodium hydroxide aqueous solution according to the proportion of 1: 1.5: adding histidine and formaldehyde according to the feeding ratio of 1.5, stirring and reacting at 60 ℃ for 2h, 4h and 6h, adjusting the pH of the reaction solution to be neutral by using hydrochloric acid, dialyzing, and freeze-drying to obtain brown histidine modified lignin.
Example 4
50mg of histidine-modified lignin modified in example 1, 500mg of azo pigment and 10mL of water were weighed into a 20mL sample bottle, and the organic pigment was thoroughly wetted with ultrasound by a cell disruptor under 340W for 5min for further use.
Example 5
60mg of the histidine-modified lignin modified in example 1, 500mg of azo pigment and 10mL of water were weighed into a 20mL sample bottle, and the organic pigment was thoroughly wetted with ultrasound by a cell disruptor under 340W for 5min for further use.
Example 6
60mg of the histidine-modified lignin modified in example 2, 500mg of the azo pigment and 10mL of water were weighed into a 20mL sample bottle, and stirred by magnetic stirring at 500rpm,800rpm and 1000rpm for 12 hours to thoroughly wet the organic pigment for further use.
Example 7
60mg of the histidine-modified lignin modified in example 2, 500mg of the azo pigment and 10mL of water were weighed into a 20mL sample bottle, and stirred by magnetic stirring at 800rpm for 6 hours to thoroughly wet the organic pigment for further use.
Example 8
60mg of the histidine-modified lignin modified in example 3, 500mg of the azo pigment and 10mL of water were weighed into a 20mL sample bottle, and the organic pigment was thoroughly wetted for use by shaking and wetting at 40 ℃ for 24 hours at 210rpm in a constant temperature shaking manner.
Example 9
60mg of histidine-modified lignin modified in example 3, 500mg of azo pigment and 10mL of water were weighed into a 20mL sample bottle, and the organic pigment was thoroughly wetted by shaking and wetting at a constant temperature and a speed of 150rpm and at 25 ℃ for 24 hours in a constant-temperature shaking manner.
Example 10
60mg of the histidine-modified lignin modified in example 1, 500mg of the azo pigment and 10mL of water were weighed into a 20mL sample bottle, and the organic pigment was thoroughly wetted by shaking and wetting at 150rpm and 40 ℃ for 18h in a constant temperature shaking manner for further use.
Example 11
60mg of the histidine-modified lignin modified in example 2, 500mg of the azo pigment and 10mL of water were weighed into a 20mL sample bottle, and the mixture was subjected to high-speed shearing at 16000rpm for 2min to sufficiently wet the organic pigment for further use.
Example 12
60mg of the histidine-modified lignin modified in example 3, 500mg of the azo pigment and 10mL of water were weighed into a 20mL sample bottle, and high-speed shearing was carried out at 16000rpm for 4min in a high-speed shearing manner to sufficiently wet the organic pigment for use.
Example 13
60mg of histidine-modified lignin modified in example 3, 500mg of azo pigment and 10mL of water were weighed into a 20mL sample bottle, and the organic pigment was thoroughly wetted with ultrasound using a cell disruptor under a power of 510W for 5min for use.
Example 14
60mg of histidine-modified lignin modified in example 2, 500mg of azo pigment and 10mL of water were weighed into a 20mL sample bottle, and the organic pigment was thoroughly wetted with ultrasound using a cell disruptor under 340W power for 8min for further use.
Example 15
40mg of histidine-modified lignin was added to the azo pigment suspension thoroughly wetted in example 4, the pH was adjusted to 6, and the mixture was ultrasonically dispersed for 15min at a power of 510W using a cell crusher to obtain a final pigment dispersion.
Example 16
60mg of histidine-modified lignin was added to the fully wetted azo pigment suspension of example 5, the pH was adjusted to 7, and the mixture was ultrasonically dispersed for 15min at a power of 510W using a cell crusher to obtain a final pigment dispersion.
Example 17
60mg of histidine-modified lignin was added to the azo pigment suspension sufficiently wetted in example 6, the pH was adjusted to 6, and the mixture was ultrasonically dispersed for 15min at 680W using a cell disruptor to obtain the final pigment dispersion.
Example 18
60mg of histidine-modified lignin was added to the azo pigment suspension thoroughly wetted in example 7, the pH was adjusted to 6, and the mixture was ultrasonically dispersed for 10min at a power of 510W using a cell crusher to obtain a final pigment dispersion.
Example 19
40mg, 60mg, 80mg, 100mg and 120mg of histidine-modified lignin were added to a fully wetted azo pigment suspension (60mg of histidine-modified lignin, 500mg of azo pigment and 10mL of water were added to a 20mL sample bottle, and ultrasonically wetted for 5min at a power of 340W using a cell disruptor), and after adjusting the pH to 6, the pigment dispersion was ultrasonically dispersed for 15min at a power of 510W using the cell disruptor.
Example 20
After adding 60mg of histidine-modified lignin to a fully wetted azo pigment suspension (60mg of histidine-modified lignin, 500mg of azo pigment and 10mL of water in a 20mL sample bottle, ultrasonically wetting for 5min at 340W by using a cell crusher, adjusting the pH value to 4, 5, 6 and 7, and ultrasonically dispersing for 15min at 510W by using the cell crusher to obtain the final pigment dispersion.
Example 21
After adding 60mg of histidine-modified lignin to a fully wetted azo pigment suspension (60mg of histidine-modified lignin, 500mg of azo pigment and 10mL of water in a 20mL sample bottle, ultrasonically wetting for 5min at 340W by using a cell crusher, adjusting the pH value to 6, and ultrasonically dispersing for 15min at 340W, 510W and 680W by using the cell crusher to obtain a final pigment dispersion.
Example 22
Adding 60mg of histidine-modified lignin into a fully wetted azo pigment suspension (60mg of histidine-modified lignin, 500mg of azo pigment and 10mL of water are added into a 20mL sample bottle, ultrasonically wetting for 5min under the condition that the power is 340W by using a cell crusher), adjusting the pH value to 6, and ultrasonically dispersing for 10min, 15min and 20min under the power of 510W by using the cell crusher to obtain the final pigment dispersion liquid.
When in test, the color paste is diluted by about 10,000 times through the nanometer granularity, and a certain amount of diluent is put into a cuvette to test the pigment grain diameter and the grain diameter distribution. The measurement results are the average particle size based on light intensity, and each sample was measured 3 times to calculate the average particle size and polydispersity index. And further characterizing the dispersion degree of the particles by a TEM (transmission electron microscope), diluting the color paste by about 5 times, taking a small amount of diluted liquid to drop on the surface of a copper mesh for testing, wherein the magnification times are 15000, 25000 and 50000 times respectively.
As shown in the attached drawings 1-4, the dispersant has good dispersibility to the dye, the particle size of the dye is uniformly distributed, and the prepared pulverizer has good effect.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments or portions thereof without departing from the spirit and scope of the invention.
Claims (10)
1. A preparation method of an environment-friendly lignin-based dispersant for azo pigments is characterized by comprising the following steps: dissolving enzymatic hydrolysis lignin in sodium hydroxide aqueous solution, adding histidine and formaldehyde in different proportions, stirring and reacting for a period of time at a certain temperature, adjusting the pH of the reaction solution to be neutral, dialyzing, and freeze-drying to obtain brown histidine modified lignin.
2. The method for preparing the environmentally friendly lignin-based dispersant for azo pigments according to claim 1, wherein: the mass feed ratio of the lignin, the histidine and the formaldehyde is 1: 0.5-2: 0.5-2.
3. The method for preparing the environmentally friendly lignin-based dispersant for azo pigments according to claim 2, wherein: the concentration of the sodium hydroxide aqueous solution is 0.5-1.5 mol/mL.
4. The method for preparing the environmentally friendly lignin-based dispersant for azo pigments according to claim 3, wherein: the concentration of the enzymatic hydrolysis lignin solution is 5-15 wt%.
5. The method for preparing the environmentally friendly lignin-based dispersant for azo pigments according to any one of claims 1 to 4, wherein: the reaction temperature is 40-80 ℃, and the reaction time is 2-6 h.
6. An environment-friendly lignin-based dispersant for azo pigments, which is characterized in that: prepared by the process according to any one of claims 1 to 5.
7. The environmentally friendly lignin-based dispersant for azo pigments according to claim 6, wherein: the using method comprises the following steps: weighing a certain mass of the histidine-modified lignin and a certain mass of azo pigment, adding the azo pigment into a container, adding water to fully wet the organic pigment, then adding a certain amount of histidine-modified lignin, adjusting the pH value, and performing ultrasonic dispersion for a certain time by using a cell crusher under a certain power to obtain the final pigment dispersion liquid.
8. The environmentally friendly lignin-based dispersant for azo pigments according to claim 7, wherein: the mass ratio of the histidine modified lignin for wetting to the azo pigment is 1: 2-16.
9. The environmentally friendly lignin-based dispersant for azo pigments according to claim 8, wherein: the organic pigment wetting method comprises one or more of magnetic stirring, constant-temperature oscillation, high-speed shearing and cell crusher ultrasound.
10. The environmentally friendly lignin-based dispersant for azo pigments according to any one of claims 6 to 9, wherein: the mass ratio of the mass of the histidine modified lignin added after the pigment is wetted to the mass of the azo pigment is 0.05-0.6: 1.
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