CN114685810A - Preparation method and application of carboxyl lignin derivative for dispersing phthalocyanine pigment - Google Patents
Preparation method and application of carboxyl lignin derivative for dispersing phthalocyanine pigment Download PDFInfo
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- CN114685810A CN114685810A CN202210485008.6A CN202210485008A CN114685810A CN 114685810 A CN114685810 A CN 114685810A CN 202210485008 A CN202210485008 A CN 202210485008A CN 114685810 A CN114685810 A CN 114685810A
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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
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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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
- C09D7/41—Organic pigments; Organic dyes
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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
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Abstract
The invention belongs to the field of phthalocyanine pigment application, and particularly relates to a preparation method and application of carboxyl lignin derivatives of dispersed phthalocyanine pigments, which are obtained by esterification reaction of acid anhydride and lignin, namely dissolving lignin, acid anhydride, 4-dimethylaminopyridine and pyridine in water, and stirring and concentrating; then the obtained product is precipitated in hydrochloric acid solution, filtered and dried. The carboxyl lignin derivative can also be obtained by carboxymethylation reaction of lignin and sodium chloroacetate, namely dissolving lignin and NaOH in water, adding sodium chloroacetate for heating reaction, adding the obtained product into HCI, performing centrifugal separation, washing, precipitating and performing suction filtration to obtain the target product. The invention has the characteristics of small particle size of the dispersed pigment, stable dispersion system, high color and high chroma of the coating and the like.
Description
Technical Field
The invention belongs to the field of phthalocyanine pigment application, and particularly relates to a preparation method and application of a carboxyl lignin derivative for dispersing phthalocyanine pigments.
Background
The phthalocyanine pigment is an important blue and green organic pigment, has bright color, strong tinting strength and high chemical stability, and is widely applied to the coloring fields of printing ink, coating, plastic rubber, color master batch, printing paste, liquid crystal display, cultural and educational products, building materials, seed fertilizers and the like. The phthalocyanine blue pigment has low surface polarity, small particles and strong hydrophobicity, is not easy to disperse in water, and influences the application effect of the phthalocyanine such as the color power of the color. Phthalocyanine pigments can be dispersed in organic solvents, but organic solvents and Volatile Organic Compounds (VOCs) can be environmentally polluting and the use of solvent systems is limited. There is also a need to develop more efficient and environmentally friendly dispersant dispersants for water.
The surface treatment of the copper phthalocyanine pigment improves the surface properties thereof to make it easily dispersible in water. For example, the method is realized by taking copper phthalocyanine as a parent body, performing hydroxymethylation, sulfonation, chlorosulfonation and chlorination, and then grafting molecular groups with different polarities; surface polarity can also be changed by coating the pigment surface for dispersion in aqueous solution.
The added dispersant can improve the wetting of the pigment for pigment dispersion, coat pigment particles, reduce and improve the agglomeration phenomenon of pigment particles and effectively improve the stable dispersion effect of the pigment. During the dispersion, the aggregate state of the pigment is mainly formed into a uniform and stable dispersion state by the action of external forces (impact and shear force). Surfactants are a commonly used dispersant, and include nonionic surfactants and ionic surfactants, for example, U.S. Pat. No. 6056814 discloses an aromatic ring-containing nonionic surfactant and a water-soluble resin as a dispersant, and U.S. Pat. No. 6379451 discloses an alkynol bond-containing nonionic surfactant and a water-soluble resin as a dispersant. The other dispersant is a high-molecular hyperdispersant, the hyperdispersant is composed of an anchoring end (dye-philic end) and a solvation chain (hydrophilic end), and the dye-philic group mainly comprises: aryl, hydrocarbon chain and other nonpolar groups, which are connected with the dye particles through ionic bonds, hydrogen bonds and van der waals force, so that the desorption phenomenon is difficult to occur; the hydrophilic groups are mainly: carboxyl, sulfonic group, amino, hydroxyl, polyether chain and the like have good compatibility with the dispersion medium, can greatly reduce the surface tension between dye particles and the dispersion medium, and can also form a space barrier on the surface of the pigment to keep the stability of a dispersion system. US patent (US7329315) discloses a polydialkylsuccinic acid and amine based derivatives for use as supramolecular dispersants for water-based inks and coatings. There is also a need to develop more efficient and environmentally friendly dispersants.
Disclosure of Invention
An object of the present invention is to provide a method for preparing a carboxylignin derivative of a dispersed phthalocyanine pigment, which can disperse the pigment with a small particle size, a stable dispersion system, and a high color tone of a coating layer.
Another object of the present invention is to provide a use of the carboxylignin derivative for dispersing phthalocyanine pigments.
In order to solve the technical problems, the invention is realized as follows:
the preparation method of the carboxyl lignin derivative of the dispersed phthalocyanine pigment is obtained by esterification reaction of acid anhydride and lignin, and comprises the following steps:
(1) dissolving lignin, acid anhydride, 4-dimethylaminopyridine and pyridine in water, and stirring and concentrating;
(2) precipitating the product obtained in the step (1) in a solution, and filtering and drying to obtain the target product carboxyl lignin derivative.
Further, the acid anhydride is succinic anhydride.
The product obtained by the preparation method of the carboxyl lignin derivative for dispersing the phthalocyanine pigment is applied to dispersing the phthalocyanine pigment, and a dispersing system is formed by the phthalocyanine pigment and the carboxyl lignin derivative; wherein the mass concentration of the carboxyl lignin derivative is 0.5-25% of that of the phthalocyanine pigment.
The application of the product obtained by the preparation method of the carboxyl lignin derivative of the dispersed phthalocyanine pigment in dispersing the phthalocyanine pigment is that the carboxyl lignin derivative, the phthalocyanine pigment and resin are mixed to prepare water-based paint; wherein the mass concentration of the carboxyl lignin derivative is 0.5-25% of that of the phthalocyanine pigment.
The product obtained by the preparation method of the carboxyl lignin derivative for dispersing the phthalocyanine pigment is applied to dispersing the phthalocyanine pigment, and a dispersing system is composed of the phthalocyanine pigment, the carboxyl lignin derivative and a wetting agent; wherein the mass concentration of the carboxylated lignin derivative is 0.5-25% of that of the phthalocyanine pigment.
Further, the wetting agent is a nonionic surfactant or an anionic surfactant; the addition amount of the anionic surfactant is 0.1-1%.
Further, the anionic surfactant is alkyl sulfate, alkyl sulfonate, alkylbenzene sulfonate, alkyl alcohol polyether sulfosuccinate monoester salt; the nonionic surfactant is alkyl fatty alcohol polyoxyethylene ether; wherein the alkyl is a C6-12 straight chain or branched chain, saturated or unsaturated alkyl.
The other preparation method of the carboxyl lignin derivative for dispersing the phthalocyanine pigment is obtained by performing carboxymethylation reaction on lignin and sodium chloroacetate, and specifically comprises the following steps:
(1) dissolving lignin and NaOH in water, and adding sodium chloroacetate for heating reaction;
(2) and (2) adding HCI into the product obtained in the step (1), carrying out centrifugal separation, washing, precipitating and carrying out suction filtration to obtain the target product carboxyl lignin derivative.
Further, the product obtained by the preparation method of the carboxyl lignin derivative of the dispersed phthalocyanine pigment is applied to the dispersed phthalocyanine pigment, and a dispersion system is formed by the phthalocyanine pigment and the carboxyl lignin derivative; wherein the mass concentration of the carboxylated lignin derivative is 0.5-25% of that of the phthalocyanine pigment.
Further, the application of the product obtained by the preparation method of the carboxyl lignin derivative of the dispersed phthalocyanine pigment in dispersing the phthalocyanine pigment is that the carboxyl lignin derivative, the phthalocyanine pigment and resin are mixed to prepare a water-based coating; wherein the mass concentration of the carboxyl lignin derivative is 0.5-25% of that of the phthalocyanine pigment.
Lignin is an oligomer containing aromatic phenol, a major byproduct of the cellulose industry, and can be derived from biomass such as roots, stems, leaves, bark, or trees of mature plants. The unmodified lignin has poor dispersibility and poor pigment dispersing effect.
The novel carboxyl lignin derivative dispersing agent prepared by the invention can be obtained by esterification reaction of acid anhydride and lignin, as shown in (I).
Wherein R may be diethyl (-CH)2CH2-, divinyl (-CH-) or aromatic group, etc.
Carboxylignins can also be obtained from carboxymethylation reactions of lignin with sodium chloroacetate (II), as shown in (II).
Lignin-OH + ClCH2COONa → Lignin-OCH2COONa (II)
The lignin may be obtained as an alkaline or dealkalized derivative.
The dispersion system comprises phthalocyanine pigment and carboxyl lignin, and can also comprise wetting agent, resin, water and the like. Specifically, the components of the dispersion system comprise, based on the total weight of the dispersion system:
the proportion of the carboxyl lignin dispersant in the phthalocyanine pigment is 0.5-25%; the system can be further dispersed in a resin and water, the resin comprising an acrylic acid carboxylic acid, and the wetting agent comprising a nonionic or ionic surfactant.
The dispersing agent can be further compounded with other wetting agents in a relatively small proportion to improve the dispersing effect, wherein the wetting agent is one or more of the following anionic surfactants: alkyl sulfates, alkyl sulfonates, alkylbenzene sulfonates, alkyl alcohol polyether sulfosuccinate monoesters; the nonionic surfactant is alkyl fatty alcohol polyoxyethylene ether and the like, wherein the alkyl is a straight chain or branched chain, saturated or unsaturated alkyl with 6-12 carbon atoms; the addition amount of the anionic surfactant is 0.1-1%.
On the other hand, the invention also provides the application of the product obtained by the preparation method of the carboxyl lignin derivative of the dispersed phthalocyanine pigment in dispersing the phthalocyanine pigment, and the carboxyl lignin derivative, the phthalocyanine pigment and resin are mixed to prepare the water-based paint, wherein the resin comprises acrylic resin, latex and the like.
The dispersing agent has good dispersion stability for phthalocyanine pigments, can enable the phthalocyanine pigments to form a stable dispersion system in water, reduces pigment agglomeration, reduces particle size and has high tinting strength.
Drawings
FIG. 1 is an infrared spectrum of a modified lignin (lower) and an unmodified lignin (upper) according to the present invention.
Detailed Description
The following detailed description is provided for the purpose of illustrating the technical solutions and the advantages of the present invention through specific embodiments, and is intended to help readers better understand the essence and features of the present invention, and not to limit the implementable scope of the present invention.
Example 1
2g of dealkalized lignin (TCI Co.), 3.6g of succinic anhydride, 0.22g of 4-dimethylaminopyridine and 18mL of pyridine were put in a 100mL flask and stirred at room temperature for 12 hours. The reaction liquid was then concentrated by a vacuum rotary evaporator. The concentrate was precipitated in 1N cold hydrochloric acid solution. The precipitated dark brown slurry was collected by vacuum filtration and dried in a vacuum oven at 60 ℃ for 3 hours to give a light brown powder product.
The synthesized product is characterized by infrared spectrum as shown in figure 1, wherein the upper part of the figure is unmodified lignin, and the lower part of the figure is the product after carboxylation. After carboxylation, the product is 3350cm-1the-OH stretching vibration peak at (A) was decreased as compared with that of the original lignin, and 2940cm of the modified product was observed-1The peak of the stretching vibration of the carboxyl CO-OH is increased. The product after carboxylation is 1740cm-1The peak of C ═ O stretching vibration appears and is 915cm-1The peak of flexural vibration was observed, and it was confirmed that a lignin derivative containing a carboxyl group was synthesized.
Example 2
55g of water, 5g of dealkalized lignin (TCI Co., Ltd.), and 20% NaOH5g were sequentially added to the reaction flask, and mixed and stirred at 40 ℃ for 30 minutes until all the components were dissolved. 10g of sodium chloroacetate were slowly added dropwise and the temperature was raised to 60 ℃ for 2 hours. After the reaction, 2n hcl was added to adjust pH to 5, and the mixture was centrifuged. Centrifuging, washing the supernatant with ethanol, vacuum filtering, and oven drying at 50 deg.C to obtain light brown product.
The infrared spectrum of the synthesized product shows. After carboxylation, the product is 3350cm-1the-OH stretching vibration peak at the position is reduced compared with that of the original lignin, and 2940cm of the modified product-1The peak of the stretching vibration of the carboxyl CO-OH is increased. The product after carboxylation is 1740cm-1Has C ═ O stretching vibration peak and reaches 915cm-1The bending vibration peak was observed, and it was confirmed that a lignin derivative containing a carboxyl group was synthesized.
Example 3
1 percent of copper phthalocyanine pigment is prepared and added into the solution containing the dispersant with different concentrations, and the solution of the copper phthalocyanine pigment dispersion system is obtained after ultrasonic oscillation for 30 min. The particle size distribution of the copper phthalocyanine pigment dispersion was measured using a NanoZS90 type nanometer laser particle sizer, and the results are shown in Table 1 below.
TABLE 1
As can be seen from Table 1 above, the carboxylignin dispersible pigment has a smaller particle size.
Example 4
The test experiment for improving the pigment color strength by the dispersant is as follows:
40mL of water and 5g of filter cake (solid content: 50%) of copper phthalocyanine pigment are weighed, dispersed for 30 minutes under high-speed stirring at 300rpm until no filter cake particles exist, then stirred for 1 hour by common stirring, heated to 65 ℃, added with 0.1g (4%) of dispersing agent, and stirred for 1 hour. After stirring, suction filtration was carried out, and the filtrate was blue without bleeding of phthalocyanine pigment (contrasting with bleeding of lignosulfonate pigment). The phthalocyanine pigment adsorbed with the dispersant is dried at 80 ℃ for 6 hours.
Tinting strength test
10g of a polyacrylic resin solution (effective content: 17.5%) was weighed, the solution was adjusted to pH 9 with ammonia, 0.5g of a copper phthalocyanine pigment and 5g of titanium dioxide were added, and the mixture was put into a ball mill pot, about 200g of zirconium beads were added, and ball-milled at 1000rpm for 2 hours. After the ball milling was completed, the dispersion was coated on a standard color plate to form an 8-micron film, dried for 30 minutes, and the coloring power was measured. The measurement wavelength range is 400-700 nm, and the wavelength interval of the wave spectrum is 10 nm. The data of the measured tinting strength are shown in table 2 below.
TABLE 2
| Dispersing agent | Color strength | Δa | Δb |
| Blank space | 100.00％ | Standard of merit | Standard of merit |
| Unmodified lignin | 97.77％ | 0.23 | 0.37 |
| Carboxyllignin (example 1) | 103.56％ | -0.96 | -1.26 |
| Carboxylignin (example 2) | 106.51％ | -1.1 | -0.49 |
As can be seen from Table 2, the color tinting strength of the carboxyl group-containing lignin coating was significantly improved.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (10)
1. A preparation method of carboxyl lignin derivatives for dispersing phthalocyanine pigments is characterized by comprising the following steps:
(1) dissolving lignin, acid anhydride, 4-dimethylaminopyridine and pyridine in water, and stirring and concentrating;
(2) and (2) precipitating the product obtained in the step (1) in a hydrochloric acid solution, and filtering and drying to obtain the target product carboxyl lignin derivative.
2. The method for producing a carboxylignin derivative of a dispersed phthalocyanine pigment according to claim 1, wherein: the anhydride is succinic anhydride.
3. Use of the product of the process for the preparation of carboxylignin derivatives of dispersed phthalocyanine pigments according to claim 1 or 2 for the dispersion of phthalocyanine pigments, characterized in that: a dispersing system is composed of phthalocyanine pigment and carboxyl lignin derivative; wherein the mass concentration of the carboxylated lignin derivative is 0.5-25% of that of the phthalocyanine pigment.
4. Use of the product of the process for the preparation of carboxylignin derivatives of dispersed phthalocyanine pigments according to claim 1 or 2 for the dispersion of phthalocyanine pigments, characterized in that: mixing carboxyl lignin derivative, phthalocyanine pigment and resin to prepare water-based paint; wherein the mass concentration of the carboxyl lignin derivative is 0.5-25% of that of the phthalocyanine pigment.
5. Use of the product of the process for the preparation of carboxylignin derivatives of dispersed phthalocyanine pigments according to claim 1 or 2 for the dispersion of phthalocyanine pigments, characterized in that: a dispersion system is composed of phthalocyanine pigment, carboxyl lignin derivative and wetting agent; wherein the mass concentration of the carboxyl lignin derivative is 0.5-25% of that of the phthalocyanine pigment.
6. The use of the product of the process for the preparation of carboxylignin derivatives of dispersed phthalocyanine pigments according to claim 5 for the dispersion of phthalocyanine pigments, characterized in that: the wetting agent is a nonionic surfactant or an anionic surfactant; the addition amount of the anionic surfactant is 0.1-1%.
7. The use of the product obtained from the process for the preparation of carboxylignin derivatives of dispersed phthalocyanine pigments according to claim 6, wherein: the anionic surfactant is alkyl sulfate, alkyl sulfonate, alkylbenzene sulfonate, alkyl alcohol polyether sulfosuccinate monoester; the nonionic surfactant is alkyl fatty alcohol polyoxyethylene ether; wherein the alkyl is a C6-12 straight chain or branched chain, saturated or unsaturated alkyl.
8. A preparation method of carboxyl lignin derivatives of dispersed phthalocyanine pigments is characterized by comprising the following steps:
(1) dissolving lignin and NaOH in water, and adding sodium chloroacetate for heating reaction;
(2) and (2) adding HCl into the product obtained in the step (1), performing centrifugal separation, and then washing, precipitating and filtering to obtain the target product carboxyl lignin derivative.
9. Use of the product of the process for the preparation of carboxylignin derivatives of dispersed phthalocyanine pigments according to claim 8 for the dispersion of phthalocyanine pigments, characterized in that: a dispersing system is composed of phthalocyanine pigment and carboxyl lignin derivative; wherein the mass concentration of the carboxylated lignin derivatives is 0.5-25% of that of the phthalocyanine pigment.
10. Use of the product of the process for the preparation of carboxylignin derivatives of dispersed phthalocyanine pigments according to claim 8 for the dispersion of phthalocyanine pigments, characterized in that: mixing carboxyl lignin derivative, phthalocyanine pigment and resin to prepare water-based paint; wherein the mass concentration of the carboxyl lignin derivative is 0.5-25% of that of the phthalocyanine pigment.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115300416A (en) * | 2022-09-01 | 2022-11-08 | 明光科迪新材料有限公司 | Preparation method of high-concentration bio-based UV nail polish color paste |
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| CN115300416A (en) * | 2022-09-01 | 2022-11-08 | 明光科迪新材料有限公司 | Preparation method of high-concentration bio-based UV nail polish color paste |
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