CN112322067A - Plastic colorant purple B and preparation method thereof - Google Patents
Plastic colorant purple B and preparation method thereof Download PDFInfo
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- CN112322067A CN112322067A CN202011219119.XA CN202011219119A CN112322067A CN 112322067 A CN112322067 A CN 112322067A CN 202011219119 A CN202011219119 A CN 202011219119A CN 112322067 A CN112322067 A CN 112322067A
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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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
- C09B1/5145—N-aryl derivatives only amino and hydroxy groups
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- C—CHEMISTRY; METALLURGY
- 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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Abstract
The invention provides a plastic colorant purple B and a preparation method thereof, wherein the purple B is prepared from a purple B crude product and methanol; wherein the crude product of the purple B is prepared from 250 parts of 25-35% butanol 200-; the methanol and the crude product of the purple B are in an equal weight part ratio of 2-4: 1; the methanol is 30-40% methanol. The plastic colorant purple B and the preparation method thereof have the advantages of quick and complete reaction, almost no side reaction, high product purity, needle-shaped crystal form of the prepared purple B, stable hue, beautiful appearance, high coloring rate, light resistance, solvent resistance and other properties.
Description
Technical Field
The invention relates to a plastic colorant and a preparation method thereof, in particular to a plastic colorant purple B and a preparation method thereof.
Background
The plastic colorant is used as a raw and auxiliary material in the plastic processing technology, and has the effects of beautifying, decorating, facilitating identification, improving weather resistance, mechanical property, optical property and the like. And are classified into inorganic pigments, organic pigments and dyes.
The pigment has excellent performance in the aspects of coloring plastic cement, sol, paper products, color paste, printing ink, paint, coating, color master batch, chemical fiber, textile and the like. Violet B is a solvent pigment of formula C21H15NO3Molecular weight is 329.35, the chinese alias: solvent violet 13; english alias: solvent violet 13. Shape: black purple needle crystal. When it meets concentrated sulfuric acid, it is green, and becomes purple with the decrease of acidity. Is soluble in acetone, ethyl acetate, benzene and hot acetic acid, slightly soluble in ethanol and insoluble in water. The application method of the purple B in the plastic product mainly comprises the following steps: injection molding, extrusion, blow molding, kneading, etc., the main principle is to melt, disperse (dissolve) the thermoplastic fluorescent pigment in the plastic product at high temperature. The structural formula is shown as (I):
at present, the purple B on the market has the defects of large excess of p-toluidine, poor properties such as light resistance, solvent resistance and the like, the coloring rate is generally 70-80%, materials are easy to become thick and difficult to stir in the reaction process in the preparation process, the 1, 4-diaminoanthraquinone leuco body serving as the raw material is wrapped in the materials and is difficult to react completely, and the reaction is difficult to reach the end point; the reaction temperature is too high, side reactions are increased, and the product purity is reduced. Therefore, it is necessary to develop a plastic colorant violet B with high coloring rate, good light resistance, good solvent resistance and the like, and capable of overcoming the above problems, and a preparation method thereof.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a plastic colorant purple B and a preparation method thereof, wherein the prepared purple B adopts p-toluidine and 1, 4-dihydroxy anthraquinone to perform equimolar reaction, the reaction is rapid and complete with micro-positive pressure of 0.04-0.08MPa, almost no side reaction exists, the product purity is high, the crystal form is needle-shaped, the hue is stable, and the appearance is beautiful. High coloring rate, high light resistance and high solvent resistance.
The technical scheme of the invention is realized as follows:
a plastic colorant violet B, said violet B being prepared from a crude product of violet B and methanol; wherein the crude product of the purple B is prepared by 250 parts by weight of 25-35 percent butanol 200-; the ratio of the methanol to the crude product of the purple B is 2-4:1 in parts by weight; the methanol is 30-40% methanol.
Preferably, the molar ratio of the 1, 4-dihydroxyanthraquinone to the p-toluidine is 1: 1.
Preferably, the ratio of the methanol to the crude product of the purple B is 3:1 in parts by weight; the methanol is 35% methanol.
Preferably, the catalyst is copper oxide.
The crude product of the purple B is prepared by the following method: adding butanol, 1.4-dihydroxyanthraquinone, p-toluidine, hydrochloric acid, boric acid and a catalyst into a condensation reaction kettle, starting stirring for 50-90r/min, heating to 120 ℃ for 100 plus materials, keeping the temperature for 4-6 hours, adjusting the micro-positive pressure in the reaction kettle to 0.04-0.08MPa to ensure that the 1.4-dihydroxyanthraquinone and the p-toluidine are subjected to condensation reaction to the end point, cooling the materials in the reaction kettle to 30-40 ℃ after the condensation reaction is completed, carrying out filter pressing, carrying out solid-liquid separation on the materials in the reaction kettle, and washing the solid materials to be neutral by using water at 75-85 ℃ after the filter pressing to obtain a purple B crude product.
Preferably, the butanol, the dihydroxy anthraquinone and the p-toluidine are firstly sucked into a condensation reaction kettle, the stirring speed is 50-60r/min, the stirring time is 5-10min, then the hydrochloric acid, the boric acid and the catalyst are added, the stirring speed is 80-90r/min, the stirring time is 5-10min, the temperature is raised to 105 ℃, the temperature is kept for 5 hours, and the condensation reaction of the 1, 4-dihydroxy anthraquinone and the p-toluidine is carried out to the end point.
Preferably, the heat preservation stage is divided into three stages, namely heating to 100 ℃, preserving heat for 1 hour, heating to 110 ℃, preserving heat for 1 hour, heating to 120 ℃, and preserving heat for 2-4 hours.
The plastic colorant purple B is prepared by the following method: and (3) putting the crude product of the purple B and methanol into a refining kettle, heating to 55-65 ℃, preserving heat for 2-3 hours, carrying out pressure filtration to obtain a filter cake, washing the filter cake to be neutral by using water at the temperature of 75-85 ℃, and then putting the filter cake into a vacuum drying oven for drying to obtain the plastic colorant purple B.
Preferably, the temperature is raised to 60 ℃.
Preferably, the filter cake is washed to neutrality with water at 80 ℃.
The preparation process mainly comprises the following chemical reactions:
the invention has the following beneficial effects: the invention relates to a plastic colorant purple B and a preparation method thereof, wherein 1, 4-dihydroxy anthraquinone, p-toluidine, hydrochloric acid, boric acid and a catalyst are adopted to carry out a configuration reaction according to an equal molar ratio, the process is controlled by micro positive pressure of 0.04MPa, segmented stirring is adopted, and the stirring speed and time are controlled, so that heat is uniformly and rapidly diffused, reactants are uniformly reacted, aggregation is not easy to generate, the consistency is moderate, the reaction is rapid and complete, side reactions are less, and the product purity is high; meanwhile, the washing temperature is controlled, so that the product is not damaged, and the product performance is not influenced; the coloring rate of the plastic colorant purple B prepared according to the invention reaches 89-91% and is more than 70-80% coloring rate on the market, and the main content of the product obtained by high performance liquid chromatography reaches more than 99%, which indicates that the product has high purity. The reaction is rapid and complete, almost no side reaction exists, the product purity is high, the crystal form is needle-shaped, the hue is stable, and the appearance is beautiful. High coloring rate, high light resistance and high solvent resistance.
Detailed Description
For a more clear understanding of the technical features, objects and advantages of the present invention, reference is now made to the following detailed description of the embodiments of the present invention taken in conjunction with the accompanying drawings, which are included to illustrate and not to limit the scope of the present invention.
Example 1
A plastic colorant violet B, said violet B being prepared from a crude product of violet B and methanol; the crude product of the purple B is prepared from 213 parts of 30% butanol, 240 parts of 1, 4-dihydroxy anthraquinone, 107 parts of p-toluidine, 122 parts of 30% hydrochloric acid, 63 parts of boric acid and 80 parts of catalyst in parts by weight; the methanol and the crude product of the purple B are in a weight part ratio of 3: 1; the methanol is 35% methanol.
A preparation method of a plastic colorant purple B comprises the following specific steps:
(1) condensation of
Absorbing butanol, 1, 4-dihydroxyanthraquinone and p-toluidine into a condensation reaction kettle, stirring at a speed of 55r/min for 7min, adding hydrochloric acid, boric acid and a catalyst at a stirring speed of 85r/min for 7min, adjusting the micro-positive pressure in the reaction kettle to 0.04MPa, heating to 100 plus materials and 120 ℃, and preserving heat for 5 hours (the heat preservation stage is divided into three stages, namely heating to 100 ℃, preserving heat for 1 hour, heating to 105 ℃, preserving heat for 1 hour, heating to 120 ℃, and preserving heat for 3 hours) to ensure that the 1, 4-dihydroxyanthraquinone and p-toluidine are subjected to condensation reaction to the end point;
(2) filter pressing and water washing
After the condensation reaction is completed, cooling the materials in the reaction kettle to 35 ℃ for plate-frame filter pressing, carrying out solid-liquid separation on the materials in the reaction kettle, and washing the solid materials to be neutral by using water at 80 ℃ after filter pressing to obtain a crude product of the purple B;
(3) refining and washing with water
Putting the crude product of the purple B and methanol into a refining kettle, heating to 60 ℃, preserving heat for 2 hours, then performing pressure filtration to obtain a filter cake, and washing the filter cake to be neutral by using water at the temperature of 80 ℃;
(4) drying and mixing
And (4) drying the product containing a small amount of water after washing in the step (3) by using a vacuum drying oven to obtain the plastic colorant purple B.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Example 2
A plastic colorant violet B, said violet B being prepared from a crude product of violet B and methanol; the crude product of the purple B is prepared from 250 parts of 25% butanol, 230 parts of 1, 4-dihydroxy anthraquinone, 108 parts of p-toluidine, 125 parts of 25% hydrochloric acid, 60 parts of boric acid and 81 parts of catalyst by weight; the ratio of the methanol to the crude product of the purple B is 2:1 in parts by weight; the methanol is 30% methanol.
A preparation method of a plastic colorant purple B comprises the following specific steps:
(1) condensation of
Absorbing butanol, 1, 4-dihydroxyanthraquinone and p-toluidine into a condensation reaction kettle, stirring at a speed of 50r/min for 10min, adding hydrochloric acid, boric acid and a catalyst at a speed of 80r/min for 10min, adjusting the micro-positive pressure in the reaction kettle to 0.06MPa, heating to 100 plus materials at 120 ℃, and preserving heat for 4 hours (the heat preservation stage is divided into three stages, namely heating to 100 ℃, preserving heat for 1 hour, heating to 110 ℃, preserving heat for 1 hour, heating to 120 ℃, preserving heat for 2 hours), so that the 1, 4-dihydroxyanthraquinone and p-toluidine are subjected to condensation reaction to the end point;
(2) filter pressing and water washing
After the condensation reaction is completed, cooling the materials in the reaction kettle to 30 ℃ for plate-frame filter pressing, carrying out solid-liquid separation on the materials in the reaction kettle, and washing the solid materials to be neutral by using water at 85 ℃ after filter pressing to obtain a crude product of the purple B;
(3) refining and washing with water
Putting the crude product of the purple B and methanol into a refining kettle, heating to 55 ℃, preserving heat for 3 hours, then carrying out pressure filtration to obtain a filter cake, and washing the filter cake to be neutral by using water at the temperature of 75 ℃;
(4) drying and mixing
And (4) drying the product containing a small amount of water after washing in the step (3) by using a vacuum drying oven to obtain the plastic colorant purple B.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Example 3
A plastic colorant violet B, said violet B being prepared from a crude product of violet B and methanol; the purple B crude product is prepared from 200 parts of 35% butanol, 250 parts of 1, 4-dihydroxy anthraquinone, 106 parts of p-toluidine, 120 parts of 35% hydrochloric acid, 65 parts of boric acid and 79 parts of catalyst in parts by weight; the ratio of the methanol to the crude product of the purple B is 4:1 in parts by weight; the methanol is 40% methanol.
A preparation method of a plastic colorant purple B comprises the following specific steps:
(1) condensation of
Absorbing butanol, 1, 4-dihydroxyanthraquinone and p-toluidine into a condensation reaction kettle, stirring at a speed of 60r/min for 5min, adding hydrochloric acid, boric acid and a catalyst, stirring at a speed of 90r/min for 5min, adjusting the micro-positive pressure in the reaction kettle to 0.08MPa, heating to 100 plus materials and 120 ℃, and preserving heat for 6 hours (the heat preservation stage is divided into three stages, namely heating to 100 ℃, preserving heat for 1 hour, heating to 110 ℃, preserving heat for 1 hour, heating to 120 ℃, and preserving heat for 4 hours), so that the 1, 4-dihydroxyanthraquinone and p-toluidine are subjected to condensation reaction to the end point;
(2) filter pressing and water washing
After the condensation reaction is completed, cooling the materials in the reaction kettle to 40 ℃ for plate-frame filter pressing, carrying out solid-liquid separation on the materials in the reaction kettle, and washing the solid materials to be neutral by using water at 75 ℃ after filter pressing to obtain a purple B crude product;
(3) refining and washing with water
Putting the crude product of the purple B and methanol into a refining kettle, heating to 65 ℃, preserving heat for 2 hours, then performing pressure filtration to obtain a filter cake, and washing the filter cake to be neutral by using water at 85 ℃;
(4) drying and mixing
And (4) drying the product containing a small amount of water after washing in the step (3) by using a vacuum drying oven to obtain the plastic colorant purple B.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Comparative example 1
The raw material ratio and the preparation method of the embodiment 1 are selected, the only difference in the preparation method is that the step (1) is not stirred, and other preparation steps are the same.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Comparative example 2
The raw material proportion and the preparation method of the embodiment 1 are selected, and the only difference in the preparation method is that the butanol, the 1, 4-dihydroxy anthraquinone and the p-toluidine in the step (1) are sucked into a condensation reaction kettle, the stirring speed is 95r/min, the stirring time is 7min, and then the hydrochloric acid, the boric acid and the catalyst are added, the stirring speed is 125r/min, and the stirring time is 7 min. The other preparation steps are the same.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Comparative example 3
The raw material proportion and the preparation method of the embodiment 1 are selected, and the only difference in the preparation method is that the butanol, the 1, 4-dihydroxy anthraquinone and the p-toluidine in the step (1) are sucked into a condensation reaction kettle, the stirring speed is 55r/min, the stirring time is 7min, and then the hydrochloric acid, the boric acid and the catalyst are added, the stirring speed is 85r/min, and the stirring time is 7 min. The other preparation steps are the same.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Comparative example 4
The raw material ratio and the preparation method of the embodiment 1 are selected, and the only difference in the preparation method is that the temperature rise range of the step (1) is changed from 120 ℃ in the range of 100-. The other preparation steps are the same.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Comparative example 5
The raw material proportion and the preparation method of the embodiment 1 are selected, and the only difference in the preparation method is that the heat preservation stage in the step (1) is changed from low to high, namely the heat preservation stage is changed from high to high, and then the heat preservation stage is changed from high to low, and the method specifically comprises the following steps: and (4) preserving heat for 5 hours (the heat preservation stage is divided into three stages, namely heating to 120 ℃, preserving heat for 1 hour, heating to 105 ℃, preserving heat for 1 hour, heating to 100 ℃, and preserving heat for 3 hours). The other preparation steps are the same.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Comparative example 6
The raw material ratio and the preparation method of the embodiment 1 are selected, and the only difference in the preparation method is that the crude product of the purple B and the methanol in the step (2) are put into a refining kettle, and the temperature is increased from 60 ℃ to 90 ℃. The other preparation steps are the same.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Comparative example 7
The raw material proportion and the preparation method of the embodiment 1 are selected, and the only difference in the preparation method is that the heat preservation time of the step (2) is shortened from 2 hours to 1 hour, and then the filter cake is obtained by pressure filtration. The other preparation steps are the same.
And carrying out performance index inspection on the product. The test results are listed in table 1.
Comparative example 8
The raw material ratio and the preparation method of the embodiment 1 are selected, and the only difference in the preparation method is that the filter cake in the step (2) is washed to be neutral by using water at 80 ℃ and water at 100 ℃. The other preparation steps are the same.
And carrying out performance index inspection on the product. The test results are listed in table 1.
First, performance detection
The coloring ratios and the data on high performance liquid chromatography of the plastic colorants violet B obtained in examples 1 to 3 and comparative examples 1 to 8 are shown in table 1 below.
Solvent resistance: one of the application properties of the pigment is the property of the pigment to resist solvent staining caused by dissolution of the solvent. According to GB/T5211.9-85 pigment solvent resistance test method.
Optical rotation resistance: one of the application properties of the pigment refers to the resistance of the pigment to color change upon exposure to sunlight. According to GB/T1710-79 pigment polarimetry.
TABLE 1
As can be seen from Table 1, the coloring ratio (130 ℃, 60min) (mass fraction of dye uptake) of the plastic colorant purple B prepared by the method of the present invention is more than 89%, and the plastic colorant purple B has higher light resistance and solvent resistance and higher purity than the quality specification and the industrial standard. As can be seen from comparative examples 1 to 3, the stirring speed, the stirring time and the stirring manner in step (1) of the production process have an important effect on the improvement of the properties of the finished product. As can be seen from comparative examples 4 to 5, the control of the temperature rise range (100 to 20 ℃) and the temperature rise first low and then high in step (1) of the preparation method plays an important role in the improvement of the properties of the finished product. As can be seen from comparative examples 6 to 8, the temperature, the holding time and the washing temperature in step (2) of the preparation method have an important effect on the improvement of the properties of the finished product. Meanwhile, the reaction process can be controlled when the micro-positive pressure is 0.04MPa in the reaction process, and high-temperature reaction is not needed.
The above embodiments are merely provided to help understand the method and core principle of the present invention, and the main steps and embodiments of the present invention are described in detail by using specific examples. To those skilled in the art, the various conditions and parameters may be varied as desired in a particular implementation in accordance with the principles of the invention, and in view of the foregoing, the description is not to be taken as limiting the invention.
Claims (10)
1. A plastic colorant violet B characterized by: the purple B is prepared from a purple B crude product and methanol; wherein the content of the first and second substances,
the crude product of the purple B is prepared from 250 parts by weight of 25-35% butanol 200-;
the ratio of the methanol to the crude product of the purple B is 2-4:1 in parts by weight; the methanol is 30-40% methanol.
2. A plastic colorant violet B according to claim 1, characterized in that: the molar ratio of the 1, 4-dihydroxyanthraquinone to the p-toluidine is 1: 1.
3. A plastic colorant violet B according to claim 1, characterized in that: the methanol and the crude product of the purple B are in a weight part ratio of 3: 1; the methanol is 35% methanol.
4. A plastic colorant violet B according to claim 1, characterized in that: the catalyst is copper oxide.
5. A plastic colorant violet B according to claim 1, characterized in that: the crude product of the purple B is prepared by the following method: adding butanol, 1.4-dihydroxyanthraquinone, p-toluidine, hydrochloric acid, boric acid and a catalyst into a condensation reaction kettle, starting stirring for 50-90r/min, heating to 120 ℃ for 100 plus materials, keeping the temperature for 4-6 hours, adjusting the micro-positive pressure in the reaction kettle to 0.04-0.08MPa to ensure that the 1.4-dihydroxyanthraquinone and the p-toluidine are subjected to condensation reaction to the end point, cooling the materials in the reaction kettle to 30-40 ℃ after the condensation reaction is completed, carrying out filter pressing, carrying out solid-liquid separation on the materials in the reaction kettle, and washing the solid materials to be neutral by using water at 75-85 ℃ after the filter pressing to obtain a purple B crude product.
6. A plastic colorant Violet B according to claim 5, wherein: firstly, the butanol, the dihydroxy anthraquinone and the p-toluidine are sucked into a condensation reaction kettle, the stirring speed is 50-60r/min, the stirring time is 5-10min, then the hydrochloric acid, the boric acid and the catalyst are added, the stirring speed is 80-90r/min, the stirring time is 5-10min, the temperature is increased to 105 ℃, the temperature is kept for 5 hours, and the condensation reaction of the 1, 4-dihydroxy anthraquinone and the p-toluidine is carried out to the end point.
7. A plastic colorant Violet B according to claim 5, wherein: the heat preservation stage is divided into three stages, namely, the temperature is firstly raised to 100 ℃, the heat preservation is carried out for 1 hour, then the temperature is raised to 110 ℃, the heat preservation is carried out for 1 hour, then the temperature is raised to 120 ℃, and the heat preservation is carried out for 2-4 hours.
8. A plastic colorant violet B according to claim 1, characterized in that: the plastic colorant purple B is prepared by the following method: and (3) putting the crude product of the purple B and methanol into a refining kettle, heating to 55-65 ℃, preserving heat for 2-3 hours, carrying out pressure filtration to obtain a filter cake, washing the filter cake to be neutral by using water at the temperature of 75-85 ℃, and then putting the filter cake into a vacuum drying oven for drying to obtain the plastic colorant purple B.
9. A plastic colorant Violet B according to claim 5, wherein: the temperature was raised to 60 ℃.
10. A plastic colorant Violet B according to claim 5, wherein: the filter cake is washed to neutrality with water at 80 ℃.
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| CN117024986A (en) * | 2023-06-28 | 2023-11-10 | 甘肃金缘泰新材料有限公司 | Environment-friendly solvent violet 13 and one-pot production process thereof |
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