CN111363379A - Pigment violet 23 composition and preparation method and application thereof - Google Patents
Pigment violet 23 composition and preparation method and application thereof Download PDFInfo
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- CN111363379A CN111363379A CN202010196428.3A CN202010196428A CN111363379A CN 111363379 A CN111363379 A CN 111363379A CN 202010196428 A CN202010196428 A CN 202010196428A CN 111363379 A CN111363379 A CN 111363379A
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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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
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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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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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
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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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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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
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Abstract
The invention provides a pigment violet 23 composition, a preparation method and application thereof, comprising the following steps: (1) weighing a certain mass of aromatic amine, adding a hydrochloric acid solution into the aromatic amine to dissolve the aromatic amine, and adding sodium nitrite into the aromatic amine under ice bath to perform diazotization reaction to obtain diazonium salt; (2) mixing the diazonium salt solution obtained in the step (1) with the pigment violet 23 filter cake after pigmentation, stirring for a period of time, adjusting the pH to 5-6 until the diazonium salt is completely reacted, and adjusting the pH to 7; (3) and (3) filtering and rinsing the product obtained in the step (2), drying at 50-80 ℃, and pulverizing to obtain the pigment violet 23 composition. The pigment derivative is generated in situ by directly pigmenting on the basis of the pigment violet 23 filter cake, the pigment derivative is not required to be separated and can be used as a product after being treated, the process steps are simplified, and the obtained pigment product has higher color strength and stability.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, and particularly relates to a pigment violet 23 composition, and a preparation method and application thereof.
Background
The pigment violet 23 has pure color and excellent application performance, and is widely used in the fields of paint, plastics, printing ink, textile printing and dyeing and the like. The synthesized pigment violet 23 crude product has disordered crystal form, large particle size, low tinting strength and no industrial application value, and the composition and the preparation treatment of the pigment crude product are required. The essence of the composition and the preparation treatment thereof is the process of reconstructing crystal forms of the crude pigment violet 23. The usual methods are kneading, ball milling, solvent methods. Modification of the derivatives and treatment with surfactants are often accompanied by the composition and its preparation; or adding water, pulping and mixing with derivatives or surface treating agent after the composition and its preparation treatment are finished; even surface treating agent, the composition and the dry powder obtained after the preparation are mixed. Among them, the modification of pigment derivatives can effectively change the polarity of the surface of the pigment particles, thereby purposefully improving some properties of the organic pigment, such as dispersibility, viscosity, anti-emulsification and the like, and is the most common and most effective means for producing different formulations of the same pigment. Such as hydrophilic surface treatments, render the pigments suitable for use in a variety of aqueous systems.
As early as 1994, Sumitomo chemical company of Japan (European patent EP0606632A1) disclosed a method for modifying pigment Violet 23 with a pigment derivative by subjecting pigment Violet 23 to a chlorosulfonation reaction with chlorosulfonic acid to produce a sulfonyl chloride, reacting with a fatty amine to produce a partially sulfonated and sulfonylaminated pigment Violet 23 derivative by adjusting the raw material ratio and the reaction conditions, and confirming the structure thereof by elemental analysis. The derivative and the pigment violet 23 are mixed according to a certain proportion to prepare the pigment composition, and compared with pure pigment violet 23, the pigment composition has better flocculation resistance, higher tinting strength and glossiness when being dispersed in amino alkyd resin.
Pigment violet 23 is first chlorosulfonated to form a carboxyl-bearing pigment derivative with β -alanine, which on average is 2.1 substitutions are determined by elemental analysis, calcium ions are added for laking, the mixture is mixed with a commercial pigment violet 23 kneaded mass cake and heated to boiling, and after filtration and drying, a new pigment preparation is obtained which, in PUR varnish, gives a transparent, strongly colored coating and is excellent in overcoating fastness.
Pigment violet 23 and sulfanilic acid are mixed by American Sun chemical company (US 2004/0200387A1), the pigment violet 23 derivative containing sulfonic acid group is generated in situ after diazotization, and then end capping is carried out by utilizing surfamine MNPA-1000 to generate ammonium salt. Compared with the conventional product, the product obtained by the method has higher color strength, transparency and better fluidity in NC ink.
It is well known that aqueous system inks or coatings will gradually develop into mainstream systems due to their environmental protection. In the literature of the past, it was found that most pigment derivatives used in aqueous systems are usually anionic or cationic and are highly susceptible to the pH of the system.
Disclosure of Invention
In view of the above, the invention provides a pigment violet 23 composition, a preparation method and an application thereof, and aims to solve the problem of low color strength of the existing pigment violet 23.
In a first aspect, the invention provides a pigment violet 23 composition comprising: pigment violet 23 and derivatives of pigment violet 23; wherein the content of the first and second substances,
the weight ratio of the derivative of the pigment violet 23 in the composition is 5-20%; the derivative of pigment violet 23 comprises the following structural formula II:
The pigment violet 23 composition provided by the first aspect of the invention is a composition of pigment violet 23 and its derivatives obtained by modifying pigment violet 23 with a diazonium salt of a non-ionic aromatic amine, and the composition has greatly improved stability and color strength compared with the pigment violet 23 in the prior art, and is beneficial to large-scale application in water-based ink and water-based paint systems.
In a second aspect, the invention provides a method of making a pigment violet 23 composition comprising the steps of: (1) weighing a certain mass of aromatic amine, adding a hydrochloric acid solution into the aromatic amine to dissolve the aromatic amine, and adding sodium nitrite into the aromatic amine under ice bath to perform diazotization reaction to obtain diazonium salt; the structural formula of the aromatic amine is shown as the following formula
I：
n is any integer between 4 and 44.
(2) Mixing the diazonium salt solution obtained in the step (1) with the pigment violet 23 filter cake after pigmentation, stirring for a period of time, adjusting the pH to 5-6 until the diazonium salt is completely reacted, and adjusting the pH to 7;
(3) and (3) filtering and rinsing the suspension obtained in the step (2), drying at 50-80 ℃, and pulverizing to obtain the pigment violet 23 composition.
Further, in the preparation method of the pigment violet 23 composition, the adding amount of the aromatic amine is 5-20% of the mass of the pigment violet 23, the mass concentration of the hydrochloric acid is 0.5-0.8%, the molar ratio of the hydrochloric acid to the aromatic amine is 2.5-3, and the molar ratio of the sodium nitrite to the aromatic amine is 1.05-1.2.
Further, the preparation method of the pigment violet 23 composition further comprises a filter cake pulping step before the step (2): weighing a certain mass of pigment violet 23 filter cake which is pigmented, adding the pigment violet 23 filter cake into a reaction kettle, pouring distilled water into the reaction kettle, and stirring and pulping the mixture to be pasty.
Further, in the preparation method of the pigment violet 23 composition, the solid content of the pigment violet 23 filter cake is 30-40%.
Further, in the above method for producing the pigment violet 23 composition, the mass of the distilled water is 5 to 10 times the mass of the pigment violet 23.
Further, in the preparation method of the pigment violet 23 composition, in the step of pulping the filter cake, one or more of quinacridone, pyrrolopyrrole dione, anthraquinone and phthalocyanine organic pigments are added to adjust the color of the pigment violet 23.
Further, in the above method for producing the pigment violet 23 composition, the amount of the organic pigment added for adjusting the color of the pigment violet 23 is 0 to 5% of the pigment violet 23.
According to the preparation method of the pigment violet 23 composition provided by the second aspect of the invention, the pigment is directly pigmented on the basis of the pigment violet 23 filter cake to generate the nonionic pigment derivative in situ, separation and purification are not needed, the pigment violet 23 composition can be used as a product after treatment, the process steps are simplified, and the obtained pigment product has high color strength and stability.
The third aspect of the invention also provides an application of the pigment violet 23 composition in water-based ink and water-based paint systems, compared with a pigment sample which is not treated by the modification method, the pigment violet 23 composition has the advantages that the nonionic pigment derivative is generated in situ, the pH value of the application system cannot be influenced, the performance cannot be influenced by the pH value of the application system, the pigment violet 23 composition can be compounded with most of auxiliary agents, the application is wider, and the color strength and the stability are better.
Detailed Description
While the preferred embodiments of the present invention are described below, it should be understood that various changes and modifications can be made by one skilled in the art without departing from the principles of the invention, and such changes and modifications are also considered to be within the scope of the invention.
The present invention provides a pigment violet 23 composition comprising: pigment violet 23 and derivatives of pigment violet 23; wherein the content of the first and second substances,
the weight ratio of the derivative of the pigment violet 23 in the composition is 5-20%; the derivative of pigment violet 23 comprises the following structural formula II:
the invention provides a preparation method of a pigment violet 23 composition, which comprises the following steps:
(1) weighing a certain mass of aromatic amine, adding a hydrochloric acid solution to dissolve the aromatic amine, and adding sodium nitrite to carry out diazotization reaction under ice bath to obtain diazonium salt.
Specifically, the structural formula of the aromatic amine in this example is formula I below:
n is any integer between 4 and 44, namely the methoxy polyethylene glycol chain segment is MPEG 400-2000.
When the molecular weight of the methoxy polyethylene glycol segment is 360-440, the structural formula of the corresponding aromatic amine is as follows:
when the molecular weight of the methoxy polyethylene glycol segment is 1000-1200, the structural formula of the corresponding aromatic amine is as follows:
when the molecular weight of the methoxy polyethylene glycol segment is 1800-2200, the structural formula of the corresponding aromatic amine is as follows:
in this step, the aromatic amine is involved in the diazotization reaction as shown in formula VI below:
the material ratio required by the reaction is as follows: the mass concentration of the hydrochloric acid is 0.5-0.8%, the molar ratio of the hydrochloric acid to the aromatic amine is 2.5-3, and the molar ratio of the sodium nitrite to the aromatic amine is 1.05-1.2; the addition amount of the aromatic amine is determined according to the mass of the pigment violet 23 to be modified, and in the embodiment, the addition amount of the aromatic amine is 5-20% of the mass of the pigment violet 23; preferably 5 to 15%.
(2) And (2) mixing the diazonium salt solution obtained in the step (1) with the pigment violet 23 filter cake after pigmentation, stirring for a period of time, adjusting the pH to 5-6 until the diazonium salt is completely reacted, and adjusting the pH to 7.
In the step, the solid content of the selected pigment violet 23 filter cake can be 30-40%, the reaction of grafting the diazonium salt onto the benzene ring of the pigment violet 23 molecule is more favorable for forming a target product under an acidic condition, but the reaction is too slow when the pH value is too low, so the pH value is controlled to be 5-6 in the step. After the reaction is complete, the pH is returned to neutral to ensure that the product is neutral.
The reaction of the diazonium salt solution with pigment Violet 23 is as follows
It should be noted that, since pigment violet 23 is very difficult to dissolve in most solvents or strong acids and bases, a cake beating step is also included before step (2): weighing a certain mass of pigment violet 23 filter cake which is subjected to pigmentation, adding the filter cake into a reaction kettle, pouring distilled water, stirring and pulping to be pasty so as to promote the subsequent reaction. During pulping, the mass of the distilled water can be determined according to the solid content of the pigment violet 23 filter cake, and is preferably 5-10 times of the mass of the pigment violet 23; preferably 6 to 8 times. The pigment press cake can be subjected to a pulping treatment before the step (1), or a press cake pulping step can be performed after the step (1) and before the step (2).
In the cake beating step, one or more of quinacridone, pyrrolopyrrole dione, anthraquinone and phthalocyanine organic pigments are added to adjust the color of the pigment violet 23. Preferably, phthalocyanine-based organic pigments are added. The addition amount of the organic pigment for adjusting the color of the pigment violet 23 is 0-5 percent of the pigment violet 23; preferably 2 to 3%.
(3) And (3) filtering the product obtained in the step (2), rinsing, drying at 50-80 ℃, and pulverizing to obtain the pigment violet 23 composition.
In specific implementation, the product prepared in the step (2) can be filtered, rinsed with distilled water for multiple times, and the solid product is dried and powdered at 80 ℃ to obtain a pigment sample.
From the above, the preparation method of the pigment violet 23 composition provided by the invention has the advantages that the pigment derivative is generated in situ by directly pigmenting on the basis of the pigment violet 23 filter cake, the separation is not needed, the pigment violet 23 composition can be used as a product after being processed, the process steps are simplified, and the obtained pigment product has high color strength and stability.
In addition, the synthesis method of the aromatic amine molecule used in the embodiment of the present invention includes the following steps:
the two-step acylation-reduction reaction is carried out according to the formula X shown in the following formula, and the specific operation is as follows: reacting p-nitrobenzoic acid in thionyl chloride to generate acyl chloride, dropwise adding N, N-dimethylformamide as a catalyst during the reaction, performing rotary evaporation to remove excessive thionyl chloride, dissolving the acyl chloride in dichloromethane, weighing methoxy polyethylene glycol (MPEG400-2000) (purchased from Jiangsu Haian petrochemical plant) with a certain mass as a nonionic surfactant, dissolving the methoxy polyethylene glycol in dichloromethane, adding triethylamine as an acid-binding agent, slowly dropwise adding an acyl chloride solution into the methoxy polyethylene glycol solution in an ice water bath, reacting at room temperature for 1-3h after dropwise adding is finished, washing with distilled water to remove inorganic salt, drying an organic phase by adopting anhydrous magnesium sulfate, and performing rotary evaporation to obtain an acylated product; dissolving the acylation product in water, adding reduced iron powder and ammonium chloride, reacting for 1-3 hours at 40-60 ℃, adding a proper amount of sodium carbonate for neutralization, filtering to remove iron powder, extracting for multiple times by using dichloromethane, combining organic phases, drying by using anhydrous magnesium sulfate, and removing the solvent by rotary evaporation to obtain the target product aromatic amine.
More specifically, the synthesis of three aromatic amines used in the examples of the present invention was as follows: weighing 16.7 parts by weight of p-nitrobenzoic acid, 29.75 parts by weight of thionyl chloride and 0.02 part by weight of N, N-dimethylformamide, mixing, carrying out reflux reaction for 2 hours under the protection of nitrogen, carrying out rotary evaporation to remove excessive thionyl chloride, dissolving acyl chloride in 200 parts of dichloromethane, weighing methyl polyethylene glycol (40 parts of MPEG400, 100 parts of MPEG1000 and 200 parts of MPEG 2000) in corresponding parts by weight, dissolving in 300 parts of dichloromethane, adding 15.15 parts by weight of triethylamine as an acid-binding agent, slowly dripping the acyl chloride solution into the MPEG solution in an ice water bath, reacting for 2 hours at room temperature after dripping is finished, washing for 3 times with distilled water to remove inorganic salt, drying an organic phase with anhydrous magnesium sulfate, and carrying out rotary evaporation to obtain an acylation product; dissolving the acylation product in 500 parts by weight of water, adding 22.4 parts by weight of reduced iron powder and 26.5 parts by weight of ammonium chloride, reacting for 3 hours at 60 ℃, adding sodium carbonate to neutralize until the pH value is 8, filtering to remove the iron powder, extracting for three times by using dichloromethane, combining organic phases, drying by using anhydrous magnesium sulfate, and removing the solvent by rotary evaporation to obtain the target product aromatic amine with the yield of 95-98%.
The invention also provides a pigment violet 23 composition prepared by the preparation method.
The invention also provides an application of the pigment violet 23 composition in water-based ink and water-based paint systems, and compared with a pigment violet 23 sample in the prior art, the pigment violet 23 composition has the advantages of higher color strength, better stability and better application performance.
The preparation of the pigment violet 23 composition of the present invention is described in detail in several specific examples below:
example 1
Synthesis of a pigment Violet 23 composition utilizing an aromatic amine of the formula (formula III): 200 parts by weight of a conventionally pigmented pigment violet 23 filter cake having a solid content of 30% was weighed, and 300 parts by weight of distilled water was added thereto for beating. And weighing 3 parts by weight of aromatic amine shown in the formula III in another small beaker, adding 100 parts by weight of 0.53% hydrochloric acid solution (the molar ratio of hydrochloric acid to aromatic amine is 2.5), adding 0.42 part by weight of sodium nitrite (the molar ratio of sodium nitrite to aromatic amine is 1.05) in an ice-water bath, diazotizing for 20min, and detecting the excessive nitrous acid condition by KI starch test paper. And pouring the diazo liquid into the pigment slurry, reacting for 30min, adjusting the pH to 5-6, keeping for 30min, heating to 50 ℃, and continuing to react until no diazonium salt exists in the system. Adjusting pH to 7, filtering, rinsing with distilled water until the conductivity of the filtrate is less than 30uS/cm, drying at 80 ℃, and powdering to obtain 58 parts by weight of the pigment composition 23.
Example 2
Synthesis of pigment violet 23 compositions using aromatic amines of the formula (formula IV): 200 parts by weight of a conventionally pigmented pigment violet 23 filter cake, having a solids content of 40%, are weighed out and beaten with 800 parts by weight of distilled water. And weighing 8 parts by weight of aromatic amine shown in the formula V in another small beaker, adding 100 parts by weight of 0.78% hydrochloric acid solution (the molar ratio of hydrochloric acid to aromatic amine is 3), adding 0.6 part by weight of sodium nitrite (the molar ratio of sodium nitrite to aromatic amine is 1.2) in an ice water bath, diazotizing, reacting for 20min, and detecting the excess nitrous acid condition by using KI starch test paper. And pouring the diazo liquid into the pigment slurry, reacting for 30min, adjusting the pH to 5-6, keeping for 30min, heating to 50 ℃, and continuing to react until no diazonium salt exists in the system. Adjusting the pH value to 7, filtering, rinsing with distilled water until the conductivity of the filtrate is less than 30uS/cm, drying at 80 ℃, and powdering to obtain 74 parts by weight of the pigment violet 23 composition.
Example 3
A pigment Violet 23 composition was synthesized using the following formula (formula V): 200 parts by weight of a conventionally pigmented pigment violet 23 filter cake having a solid content of 35% was weighed out and beaten with 300 parts by weight of distilled water. And taking another small beaker, weighing 14 parts by weight of aromatic amine shown in the formula VI, adding 100 parts by weight of 0.72% hydrochloric acid solution (the molar ratio of hydrochloric acid to aromatic amine is 3), adding 0.5 part by weight of sodium nitrite (the molar ratio of sodium nitrite to aromatic amine is 1.1) in an ice water bath, diazotizing, reacting for 20min, and detecting the excessive nitrous acid condition by KI starch test paper. And pouring the diazo liquid into the pigment slurry, reacting for 30min, adjusting the pH to 5-6, keeping for 30min, heating to 50 ℃, and continuing to react until no diazonium salt exists in the system. Adjusting the pH value to 7, filtering, rinsing with distilled water until the conductivity of the filtrate is less than 30uS/cm, drying at 80 ℃, and pulverizing to obtain 68 parts by weight of the pigment composition.
Example 4:
modification of pigment violet 23 with an aromatic amine of formula IV: weighing 200 parts by weight of a conventionally pigmented pigment violet 23 filter cake, wherein the solid content is 40%; 4 parts by weight of pigment blue 15:3, wherein the solid content is 35%, adding 800 parts by weight of distilled water, and pulping. And weighing 8 parts by weight of aromatic amine shown in the formula IV in another small beaker, adding 100 parts by weight of 0.78% hydrochloric acid solution (the molar ratio of hydrochloric acid to aromatic amine is 3), adding 0.56 part by weight of sodium nitrite (the molar ratio of sodium nitrite to aromatic amine is 1.1) in an ice water bath, diazotizing, reacting for 20min, and detecting the excess nitrous acid condition by using KI starch test paper. And pouring the diazo liquid into the pigment slurry, reacting for 30min, adjusting the pH to 5-6, keeping for 30min, heating to 50 ℃, and continuing to react until no diazonium salt exists in the system. Adjusting pH to 7, filtering, rinsing with distilled water until the conductivity of the filtrate is less than 30uS/cm, drying at 80 ℃, and powdering to obtain 82 parts by weight of the pigment composition.
Comparative example 1:
pigmentation without aromatic amine: to maintain the consistency of the conditions with the examples, and to exclude the influence of inorganic salts contained in the pigments on the experiments, the comparative example was conducted by subjecting the conventionally pigmented pigment violet 23 filter cake to the steps of beating and rinsing. Weighing 200 parts by weight of a conventional pigmented pigment violet 23 filter cake, wherein the solid content is 40%, adding 800 parts by weight of distilled water, pulping for 2 hours, filtering, rinsing with distilled water until the conductivity of the filtrate is less than 30uS/cm, drying at 80 ℃, and crushing to obtain 76 parts by weight of a pigment sample.
The pigment violet 23 pigment composition prepared in the embodiment of the invention and the comparative example is applied to water-based ink, and the performance of the obtained sample is detected, wherein the process comprises the following steps: weighing 45g pigment and acrylate resin emulsion (such as BASF)
61)60g, 0.75g of defoaming agent, 45g of deionized water and 180g of zirconium beads, and shaking for 1 hour. The zirconium beads were filtered off to obtain a dispersion. The dispersion can be prepared into water-based ink by adding different resins and additives. And (5) manufacturing a color card, and detecting the properties of the product, such as color, tinting strength, viscosity and the like.
The instrument equipment comprises: the shaker was model F & FM SO-450, the viscometer was model BROOKFIELD DE-V, the high speed mixer was model Speedmixer DAC 400 FVZ, and the colorimeter was model DATACOLOR SF-450X.
The results of the properties of the pigment of the present invention applied to water-based inks are shown in table 1 below:
| pigment sample | Colour(s) | Color strength | Viscosity (mpas) |
| Example 1 | Approximation | 108％ | 460 |
| Example 2 | Reddish colour | 112％ | 250 |
| Example 3 | Approximation | 105％ | 120 |
| Example 4 | Micro blue | 111％ | 240 |
| Comparative example 1 | Standard of merit | 100％ | 1260 |
As can be seen from table 1 above: pigment violet 23 prepared according to examples 1-4 of the present invention has a similar color (only example 4, slightly blue due to the addition of pigment blue 15: 3) and an increase in color strength of 5-12% when compared to the unmodified pigment violet 23 sample of comparative example 1, wherein: the highest tinctorial strength was obtained with the addition of 10% of the MPEG1000 substituted aromatic amine (example 2) and, in addition, the viscosity of the aqueous inks prepared from the pigments in the various examples of the invention were improved to varying degrees.
The pigment violet 23 pigment composition prepared in the embodiment of the invention and the comparative example is applied to water-based paint, and the performance of the obtained sample is detected, wherein the process comprises the following steps: weighing 40g pigment and acrylate resin emulsion (such as BASF)
77)25g, 0.75g of defoaming agent, 50g of deionized water and 150g of zirconium beads, and shaking for 1 hour. The zirconium beads were filtered off to obtain a dispersion. The dispersion can be prepared into a water-based coating by adding different resins and additives. And (5) manufacturing a color card, and detecting the properties of the product, such as color, tinting strength, viscosity and the like.
The results of the properties of the pigments of the invention applied to water-borne paints/lacquers are shown in table 2 below:
as can be seen from table 2 above: pigment violet 23 prepared according to examples 1-4 of the present invention has a similar color (only example 4, slightly blue due to the addition of pigment blue 15: 3) and an increase in color strength of 8-15% when compared to the unmodified pigment violet 23 sample of comparative example 1, wherein: the pigment compositions of the present invention have the highest tinctorial strength when 10% of the MPEG 1000-substituted aromatic amine (example 2) is added, and the viscosity and dispersibility of the aqueous coating compositions prepared using the pigments of the various examples of the present invention are improved to various degrees. In conclusion, when the pigment violet 23 composition provided by the invention is used in water-based ink and water-based paint systems, compared with a pigment sample which is not treated by the method, the pigment violet 23 composition has the advantages of higher color strength, better stability and better application performance.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (9)
1. A pigment violet 23 composition comprising: pigment violet 23 and derivatives of pigment violet 23; wherein the content of the first and second substances,
the weight ratio of the derivative of the pigment violet 23 in the composition is 5-20%; the derivative of pigment violet 23 comprises the following structural formula II:
2. A method of making the pigment violet 23 composition of claim 1, comprising the steps of:
(1) weighing a certain mass of aromatic amine, adding a hydrochloric acid solution into the aromatic amine to dissolve the aromatic amine, and adding sodium nitrite into the aromatic amine under ice bath to perform diazotization reaction to obtain diazonium salt; the structural formula of the aromatic amine is shown as the following formula I:
n is any integer between 4 and 44.
(2) Mixing the diazonium salt solution obtained in the step (1) with the pigment violet 23 filter cake after pigmentation, stirring for a period of time, adjusting the pH to 5-6 until the diazonium salt is completely reacted, and adjusting the pH to 7;
(3) and (3) filtering and rinsing the suspension obtained in the step (2), drying at 50-80 ℃, and pulverizing to obtain the pigment violet 23 composition.
3. The method of preparing a pigment violet 23 composition of claim 2, wherein the aromatic amine is added in an amount of 5 to 20% by mass of the pigment violet 23, the hydrochloric acid has a concentration of 0.5 to 0.8% by mass, the molar ratio of the hydrochloric acid to the aromatic amine is 2.5 to 3, and the molar ratio of the sodium nitrite to the aromatic amine is 1.05 to 1.2.
4. A process for preparing a pigment violet 23 composition according to claim 2 further comprising a cake beating step prior to step (2): weighing a certain mass of pigment violet 23 filter cake which is pigmented, adding the pigment violet 23 filter cake into a reaction kettle, pouring distilled water into the reaction kettle, and stirring and pulping the mixture to be pasty.
5. A process for preparing the pigment violet 23 composition of claim 2, wherein the pigment violet 23 press cake has a solids content of 30-40%.
6. A method of making the pigment violet 23 composition of claim 2, wherein the mass of the distilled water is 5-10 times the mass of the pigment violet 23.
7. A process for preparing a pigment Violet 23 composition according to claim 4, wherein in said cake beating step, one or more of quinacridones, pyrrolopyrrole diones, anthraquinones, phthalocyanines organic pigments are added to adjust the color of pigment Violet 23.
8. A process for preparing a pigment Violet 23 composition according to claim 7, wherein the organic pigment to adjust the color of pigment Violet 23 is added in an amount of 0 to 5% of pigment Violet 23.
9. Use of the pigment violet 23 composition of claim 8 in aqueous ink and aqueous paint systems.
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| CN202010196428.3A CN111363379B (en) | 2020-03-19 | 2020-03-19 | Pigment violet 23 composition and preparation method and application thereof |
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| CN202010196428.3A CN111363379B (en) | 2020-03-19 | 2020-03-19 | Pigment violet 23 composition and preparation method and application thereof |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0606632A1 (en) * | 1992-12-25 | 1994-07-20 | Sumitomo Chemical Company, Limited | Pigment compounds and application thereof |
| CN1360617A (en) * | 1999-07-09 | 2002-07-24 | 西巴特殊化学品控股有限公司 | Pigments having improved colouristic properties and process for their preparation |
| CN1484679A (en) * | 2001-02-10 | 2004-03-24 | Acid pigment dispersamts and pigment preparations | |
| US20040200387A1 (en) * | 2003-04-14 | 2004-10-14 | Arthur Kevin A. | Treatment of high performance pigments |
| CN102660400A (en) * | 2007-01-26 | 2012-09-12 | 荷兰联合利华有限公司 | Shading composition |
-
2020
- 2020-03-19 CN CN202010196428.3A patent/CN111363379B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0606632A1 (en) * | 1992-12-25 | 1994-07-20 | Sumitomo Chemical Company, Limited | Pigment compounds and application thereof |
| CN1360617A (en) * | 1999-07-09 | 2002-07-24 | 西巴特殊化学品控股有限公司 | Pigments having improved colouristic properties and process for their preparation |
| CN1484679A (en) * | 2001-02-10 | 2004-03-24 | Acid pigment dispersamts and pigment preparations | |
| US20040200387A1 (en) * | 2003-04-14 | 2004-10-14 | Arthur Kevin A. | Treatment of high performance pigments |
| CN102660400A (en) * | 2007-01-26 | 2012-09-12 | 荷兰联合利华有限公司 | Shading composition |
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| CN111363379B (en) | 2021-11-05 |
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