CN110591411A - Preparation method of carbazole di-dumb-oxazine organic pigment - Google Patents
Preparation method of carbazole di-dumb-oxazine organic pigment Download PDFInfo
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- CN110591411A CN110591411A CN201910976339.8A CN201910976339A CN110591411A CN 110591411 A CN110591411 A CN 110591411A CN 201910976339 A CN201910976339 A CN 201910976339A CN 110591411 A CN110591411 A CN 110591411A
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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
- C09B19/00—Oxazine 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
- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0002—Grinding; Milling with solid grinding or milling assistants
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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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
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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
- C09B67/008—Preparations of disperse dyes or solvent dyes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paints Or Removers (AREA)
Abstract
A preparation method of carbazole di-dumb-oxazine organic pigment comprises the following steps: adding the pigment violet P.V.23 crude product into grinding equipment, and crushing and grinding at a certain temperature; putting the ground crude pigment into a kneader, adding an inorganic salt grinding aid and a binder into the kneader, and grinding for a certain time at a certain temperature to obtain a pigment mixture; adding water, pulping, washing the adhesive and the inorganic salt grinding aid with water to remove, drying and crushing to obtain dark purple powder; and adding a pigment dispersant into the prepared dark purple powder, and uniformly mixing to obtain the final required product. The pigment violet P.V.23 prepared by the invention has high pigment tinting strength and red phase, and when the pigment violet P.V.23 is applied to a solvent-based ink system, the viscosity of the ink system is low, the fluidity is good, and the stability is high.
Description
Technical Field
The invention relates to a preparation method of a high-grade purple organic pigment composition, in particular to a preparation method of a carbazole di-dumb-oxazine (P.V.23) organic pigment.
Background
The pigment purple P.V.23 is a blue-violet high-grade organic pigment, has high tinting strength, good heat resistance, solvent resistance, light resistance, weather resistance and other excellent performances, and can be applied to the coloring of high-grade ink, paint, plastic and the like. In the past, pigment violet P.V.23 is mainly used for toning due to high price, and the application of the pigment violet P.V.23 is more and more extensive along with the reduction of production cost.
When the pigment violet P.V.23 prepared by the traditional process method is applied to solvent-based ink, flocculation occurs, the viscosity of a system is increased, the fluidity is deteriorated, and the use of the pigment violet P.V.23 in the field is seriously influenced.
On the other hand, p.v.23 has a larger blue color and more application fields prefer a redder purple hue than the traditional color, so that improvement in the manufacturing method and improvement of the red phase are required.
Disclosure of Invention
The invention provides a preparation method of carbazole di-dumb-oxazine organic pigment for overcoming the defects of the prior art, the prepared pigment purple P.V.23 has high pigment tinting strength and red phase, and when the pigment purple P.V.23 is applied to a solvent type ink system, the viscosity of the ink system is low, the fluidity is good, and the stability is high.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a preparation method of carbazole di-dumb-oxazine organic pigment comprises the following steps:
a. adding the pigment violet P.V.23 crude product into grinding equipment, and crushing and grinding at a certain temperature to ensure that the particle size of the pigment violet P.V.23 crude product is less than 50 nm; at this time, the crystal surface is incomplete, and the surface energy is high, so that the crystal is agglomerated together and is difficult to disperse;
b. b, putting the ground crude pigment product obtained in the step a into a kneader, adding an inorganic salt grinding aid and a binder into the kneader, and grinding for a certain time at a certain temperature to obtain a pigment mixture;
c. treating the kneaded pigment mixture with water, washing the binder and the inorganic salt grinding aid with water to remove, drying and crushing to obtain dark purple powder;
d. and adding a pigment dispersant into the prepared dark purple powder, and uniformly mixing to obtain the final required product.
In the step b, the inorganic salt grinding aid is sodium chloride, sodium sulfate or calcium chloride, and the addition amount of the inorganic salt grinding aid is 4-10 times of the mass of the pigment mixture; the further increase in the amount of salt has no more significant advantage for the milling but only an increase in the cost.
In the preparation method of the carbazole di-dumb-azine organic pigment, the adhesive is a water-soluble organic solvent of condensation products or condensation products of alcohols and alcohols.
In the preparation method of the carbazole di-dumb-azine organic pigment, the adhesive is diethylene glycol or polyethylene glycol, and the addition amount of the adhesive is 1-3 times of the weight of the pigment. The adhesive is prepared from a water-soluble organic solvent, has no solubility to an inorganic salt grinding aid, and is convenient to separate from pigment molecules in later washing.
In the preparation method of the carbazole di-dumb-azine organic pigment, in the step b, the kneading temperature is 80-120 ℃.
In the step a, an inorganic salt grinding aid is added in the process of grinding the crude product of the pigment violet P.V.23, and the addition amount of the inorganic salt grinding aid is 10-200% of the weight of the crude product of the pigment violet P.V.23.
In the preparation method of the carbazole di-dumb-azine organic pigment, in the step a, the grinding temperature is 80-120 ℃. Preventing overheating from causing burning or destruction of the pigment.
In the preparation method of the carbazole di-dumb-azine organic pigment, in the step d, the pigment dispersant is a sulfonated derivative of pigment violet P.V.23, and the addition amount of the pigment dispersant is 5-20% of the weight of the dark purple powder.
The invention has the beneficial effects that:
1. the pigment violet P.V.23 crude product ground by the grinding equipment is further ground by a kneader, grinding aids and adhesives are added in the process of secondary grinding, the materials are adjusted to be in a proper state by the adhesives, so that the materials have the best kneading effect, the size of pigment particles obtained by final kneading is properly grown, the crystal surface is relatively perfect, the surface energy is reduced, the particles are mainly in a corner or edge contact mode when being coagulated again, and the pigment violet P.V.23 crude product can be easily opened and dispersed in a medium when being applied, so that the tinting strength is improved.
2. According to the invention, the pigment dispersing agent is added into the kneaded and washed dark purple pigment powder or at the later stage of kneading, a sulfonic acid group is introduced on the pigment molecule to modify the surface of the pigment, and when the modified pigment is added into a solvent type ink (such as solvent type nitrocellulose gravure ink and polyamide ink) system, the dispersing agent promotes the compatibility of the pigment and a solvent type ink medium, so that the viscosity of the ink medium is reduced, and the ink can be stably stored for a long time without viscosity increase.
Detailed Description
The present invention will be further described with reference to the following examples.
The crude pigment purple P.V.23 has coarse particles, the particle size is dozens to hundreds of microns, and the crude pigment purple P.V.23 cannot be used as a pigment, and the crude pigment purple P.V.23 has to be crushed by a certain means to reduce the particle size to hundreds of nanometers to dozens of nanometers. The crushing means includes mechanical grinding methods such as ball milling, kneading and the like; also included are acid processes, such as acid dissolution, acid swelling.
The grinding equipment adopted in the grinding process of the crude pigment purple P.V.23 product is a ball mill or a vibration grinder, has strong impact and grinding capacity, and can input energy required by pigment crushing to the pigment to enhance the grinding effect. The grinding media filled in the grinding device can be steel balls, steel bars and the like, and the density and the size of the grinding media are proper so as to obtain enough impact and grinding effects and have enough grinding surface area.
Example 1
a. In a 10-square horizontal ball mill, 1/2-volume steel balls with the diameter of 20-30mm are filled. 1000kg of crude pigment violet P.V.23 and 500kg of sodium sulphate were added. Milling at 25rpm for 24 hours.
b. 100kg (pigment content) of the above millbase was charged into a 1500L kneader, 400kg of sodium chloride powder and 100kg of diethylene glycol were added, and kneaded at 110 ℃ for 10 hours at 100 ℃. The kneaded mixture was pulped with 10 times of water, the salt and the solvent were washed off with the filtered water, and then dried and pulverized to obtain 98kg of a pigment.
c. And adding 10kg of pigment sulfonic acid derivative into the obtained pigment powder, and uniformly mixing to obtain a final product.
Example 2
a. In a 10-square horizontal ball mill, 2/3-volume steel balls with the diameter of 20-30mm are filled. 1000kg of crude pigment violet P.V.23 and 500kg of sodium sulphate were added. Milling at 25rpm for 24 hours.
b. 100kg (pigment content) of the above millbase was charged into a 1500L kneader, 400kg of sodium chloride powder and 100kg of diethylene glycol were added, and kneaded at 110 ℃ for 10 hours at 100 ℃. 10kg of a pigment sulfonic acid derivative was added and kneading was continued for 1 hour. The kneaded mixture was pulped with 10 times of water, the salt and the solvent were washed off with the filtered water, and then dried and pulverized to obtain 108kg of a pigment.
Example 3
a. In a 10-square horizontal ball mill, 2/3-volume steel balls with a diameter of 25mm were charged. 1000kg of crude pigment violet P.V.23 and 500kg of sodium sulphate were added. Milling at 25rpm for 24 hours.
b. 50kg (pigment content) of the above millbase was charged into a 1500L kneader, 500kg of sodium chloride powder and 90kg of diethylene glycol were added, and kneaded at 100 ℃ and 110 ℃ for 10 hours. The kneaded mixture was pulped with 10 times of water, the salt and the solvent were washed off with the filtered water, and then dried and pulverized to obtain 98kg of a pigment.
c. And adding 10kg of pigment sulfonic acid derivative into the obtained pigment powder, and uniformly mixing to obtain a final product.
Example 4
a. In a 10-square horizontal ball mill, 2/3-volume steel balls with a diameter of 25mm were charged. 1000kg of crude pigment violet P.V.23 and 200kg of sodium sulphate were added. Milling at 25rpm for 24 hours.
b. 100kg (pigment content) of the above millbase was charged into a 1500L kneader, 400kg of sodium chloride powder and 100kg of diethylene glycol were added, and kneaded at 110 ℃ for 10 hours at 100 ℃. The kneaded mixture was pulped with 10 times of water, the salt and the solvent were washed off with the filtered water, and then dried and pulverized to obtain 98kg of a pigment.
c. And adding 10kg of pigment sulfonic acid derivative into the obtained pigment powder, and uniformly mixing to obtain a final product.
Comparative example
The traditional kneading process comprises the following steps:
100kg of crude PV23 was fed into a 1500L kneader, 450kg of sodium chloride powder and 100kg of diethylene glycol were added, and kneaded at 110 ℃ for 10 hours. The kneaded mixture was pulped with 10 times of water, the salt and the solvent were washed off with the filtered water, and then dried and pulverized to obtain 98kg of a pigment.
Comparison results
The pigments obtained in the above examples were dispersed by milling in an NC type solvent ink in a laboratory facility for comparison, and the results of the comparison are shown in Table 1.
TABLE 1 comparison of Properties
| Test specimen | Viscosity of the oil | Gloss of | Coloured light | Color strength% |
| Comparative example | 1200cp | Standard of merit | Standard of merit | 100 |
| Example 1 | 56cp | Is obviously higher than the standard | +3 grade red | 135 |
| Example 2 | 50cp | Is obviously higher than the standard | +3.5 grade Red | 140 |
| Example 3 | 40cp | Apparent high and standard | +3 grade red | 130 |
| Example 4 | 50cp | Is obviously higher than the standard | +2.5 grade red | 130 |
As can be seen from Table 1, the gloss, shade and chroma of the pigments of the examples of the present invention are higher than those of the comparative examples.
Claims (8)
1. A preparation method of carbazole di-dumb-oxazine organic pigment is characterized by comprising the following steps: the preparation method comprises the following steps:
a. adding the pigment violet P.V.23 crude product into grinding equipment, and crushing and grinding at a certain temperature to control the particle size of the pigment violet P.V.23 crude product to be below 50 nanometers;
b. b, putting the ground crude pigment product obtained in the step a into a kneader, adding an inorganic salt grinding aid and a binder into the kneader, and grinding for a certain time at a certain temperature to obtain a pigment mixture;
c. treating the kneaded pigment mixture with water, washing the binder and the inorganic salt grinding aid with water to remove, drying and crushing to obtain dark purple powder;
d. and adding a pigment dispersant into the prepared dark purple powder, and uniformly mixing to obtain the final required product.
2. The method of preparing a carbazole di-dumb-azine organic pigment according to claim 1, characterised in that: in the step b, the inorganic salt grinding aid is sodium chloride, sodium sulfate or calcium chloride, and the addition amount of the inorganic salt grinding aid is 4-10 times of the mass of the pigment mixture.
3. The method of preparing a carbazole di-dumb-azine organic pigment according to claim 2, characterised in that: the adhesive is a water-soluble organic solvent of condensation polymers or condensation products of alcohols and alcohols.
4. The method of preparing a carbazole di-dumb-azine organic pigment according to claim 3, characterised in that: the adhesive is diethylene glycol or polyethylene glycol, and the addition amount of the adhesive is 1-3 times of the weight of the pigment.
5. The method of preparing a carbazole di-dumb-azine organic pigment according to claim 4, characterised in that: in the step b, the kneading temperature is 80-120 ℃.
6. The method of preparing a carbazole di-dumb-azine organic pigment according to claim 5, characterised in that: in the step a, an inorganic salt grinding aid is added in the process of grinding the crude pigment violet P.V.23, and the addition amount of the inorganic salt grinding aid is 10-200% of the weight of the crude pigment violet P.V.23.
7. The method of preparing a carbazole di-dumb-azine organic pigment according to claim 6, characterised in that: in the step a, the grinding temperature is 80-120 ℃.
8. The method of preparing a carbazole di-dumb-azine organic pigment according to claim 7, characterised in that: in the step d, the pigment dispersant is sulfonated derivative of pigment purple P.V.23, and the addition amount of the sulfonated derivative is 5-20% of the weight of the dark purple powder.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910976339.8A CN110591411A (en) | 2019-10-15 | 2019-10-15 | Preparation method of carbazole di-dumb-oxazine organic pigment |
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| CN201910976339.8A CN110591411A (en) | 2019-10-15 | 2019-10-15 | Preparation method of carbazole di-dumb-oxazine organic pigment |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111732840A (en) * | 2020-07-03 | 2020-10-02 | 山东凯瑞尔光电科技有限公司 | Modified yellow pigment for photoresist, preparation method and application thereof |
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| WO2010112427A1 (en) * | 2009-03-31 | 2010-10-07 | Solvay Sa | Process for the preparation of easily dispersible violet pigment |
| CN103740133A (en) * | 2013-12-30 | 2014-04-23 | 先尼科化工（上海）有限公司 | Grinding method for organic pigment salt |
| CN108795101A (en) * | 2017-06-02 | 2018-11-13 | 银川百泓新材料科技有限公司 | A kind of kneading method prepares the preparation process and permanent violet of permanent violet |
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2019
- 2019-10-15 CN CN201910976339.8A patent/CN110591411A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006091649A (en) * | 2004-09-27 | 2006-04-06 | Dainippon Ink & Chem Inc | Method for manufacturing pigment composition for blue-pixel portion of color filter, and the color filter |
| CN1958688A (en) * | 2006-11-24 | 2007-05-09 | 东华大学 | Nano pigment, preparation methd and application |
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| WO2010112427A1 (en) * | 2009-03-31 | 2010-10-07 | Solvay Sa | Process for the preparation of easily dispersible violet pigment |
| CN103740133A (en) * | 2013-12-30 | 2014-04-23 | 先尼科化工（上海）有限公司 | Grinding method for organic pigment salt |
| CN108795101A (en) * | 2017-06-02 | 2018-11-13 | 银川百泓新材料科技有限公司 | A kind of kneading method prepares the preparation process and permanent violet of permanent violet |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111732840A (en) * | 2020-07-03 | 2020-10-02 | 山东凯瑞尔光电科技有限公司 | Modified yellow pigment for photoresist, preparation method and application thereof |
| CN111732840B (en) * | 2020-07-03 | 2024-03-19 | 山东凯瑞尔光电科技有限公司 | Modified yellow pigment for photoresist, preparation method and application thereof |
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Application publication date: 20191220 |