CN113156782A - Fluorescent ink powder with uniform charge amount and application thereof - Google Patents
Fluorescent ink powder with uniform charge amount and application thereof Download PDFInfo
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- CN113156782A CN113156782A CN202110408029.3A CN202110408029A CN113156782A CN 113156782 A CN113156782 A CN 113156782A CN 202110408029 A CN202110408029 A CN 202110408029A CN 113156782 A CN113156782 A CN 113156782A
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
- G03G9/0975—Organic compounds anionic
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
- G03G9/09741—Organic compounds cationic
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- Inks, Pencil-Leads, Or Crayons (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
The invention relates to the field of ink powder, in particular to fluorescent ink powder with uniform charge amount, fluorescent ink powder and application thereof. The fluorescent ink powder with uniform charge amount comprises fluorescent microspheres, wherein the fluorescent microspheres have a chemical structural formula as shown in formula (1) or formula (2):
Description
Technical Field
The invention relates to the field of ink powder, in particular to fluorescent ink powder with uniform charge amount, fluorescent ink powder and application thereof.
Background
With the rapid development of science and technology, people gradually realize the importance of information authenticity and safe storage, and the demand for developing novel anti-counterfeiting materials and anti-counterfeiting technology is more urgent. The fluorescent carbon powder can show color change under the irradiation of ultraviolet rays, namely, the printed characters or patterns can only display information under special excitation conditions, so that the effect of 'visible and invisible' is achieved, and the information leakage can be effectively avoided.
Laser printing is as novel printing technique, it is effectual to have the printing, print fast, advantage that the noise is little, laser printing compares in inkjet printing, has high-speed, high efficiency, economy, environmental protection's advantage, but because laser printing requires its powdered ink to need the charge, consequently, the powdered ink that is applied to in laser printing at present all prepares through the method of adding the charge regulator in the powdered ink that prepares through physics mixing method, thereby makes the production technology of powdered ink complicated, and the charge homogeneity of powdered ink is poor, leads to the powdered ink to adsorb incompletely, and then influences the printing quality.
Disclosure of Invention
Therefore, the technical problem to be solved by the present invention is to overcome the defect of poor uniformity of the charge amount of the fluorescent toner in the prior art, thereby providing a fluorescent toner with uniform charge amount and application thereof.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
the fluorescent toner with uniform charge amount comprises fluorescent microspheres, wherein the fluorescent microspheres have a chemical structural formula as shown in formula (1) or formula (2):
further, the fluorescent group includes at least one of a blue fluorescent group, a red fluorescent group, and a green fluorescent group.
Further, the fluorescent microsphere is prepared according to the following steps:
mixing 0.01-1% of fluorescent monomer, 20-40% of styrene, 5-10% of butyl acrylate, 0.1-0.8% of divinylbenzene, 0.5-2.5% of dodecyl mercaptan, 3-18% of wax, 1-15% of initiator, 0.5-5% of monomer with positive/negative charge groups and 40-50% of first dispersing agent for polymerization reaction.
Further, the positively/negatively charged group-bearing monomer includes at least one of formulas (3) - (6):
wherein m and n are 1-10.
Further, the initiator comprises at least one of potassium persulfate, azobisisobutyronitrile, dibenzoyl peroxide, lauroyl peroxide, tert-butyl peroxypivalate, isopropyl peroxydicarbonate and dicyclohexyl peroxydicarbonate; and/or the first dispersing agent comprises at least one of sodium dodecyl benzene sulfonate, polyether surface active group and colloid of magnesium hydroxide, magnesium carbonate, calcium phosphate, talcum powder and the like.
Further, the polymerization is emulsion polymerization or suspension polymerization.
Further, the fluorescent toner also comprises a second dispersing agent.
Further, the mass ratio of the fluorescent microspheres to the second dispersing agent is 0.1-1.5%.
Further, the second dispersing agent comprises at least one of nano silicon dioxide, aluminum oxide, titanium dioxide, magnesium silicate, calcium stearate and calcium laurate.
The invention also provides application of the fluorescent toner in laser printing.
The technical scheme of the invention has the following advantages:
1. according to the fluorescent toner provided by the invention, the macromolecular fluorescent microspheres with charges are introduced, the negative charge groups in the fluorescent microspheres are directly connected with the molecular weight of the macromolecular fluorescent microspheres, and the whole fluorescent microspheres are of a molecular chain structure, so that the charge quantity of the obtained fluorescent toner is more uniform and stable, and the fluorescent toner is suitable for laser printing with higher quality.
2. According to the fluorescent toner provided by the invention, the tert-butyl salicylic acid metal complex monomer with negative charges is used as a raw material for preparing the fluorescent microspheres, so that the negative charges can be directly introduced in the preparation process of the fluorescent microspheres, a physical mixing method is not needed for adding a charge regulator, the preparation process is simple and efficient, and the fluorescent toner with uniform charge is obtained.
Detailed Description
The following examples are provided to further understand the present invention, not to limit the scope of the present invention, but to provide the best mode, not to limit the content and the protection scope of the present invention, and any product similar or similar to the present invention, which is obtained by combining the present invention with other prior art features, falls within the protection scope of the present invention.
The examples do not show the specific experimental steps or conditions, and can be performed according to the conventional experimental steps described in the literature in the field. The reagents or instruments used are not indicated by manufacturers, and are all conventional reagent products which can be obtained commercially.
Example 1
The embodiment relates to blue fluorescent toner applied to laser printing, which is prepared according to the following steps:
s1, synthesis of blue fluorescent monomer: 4-Diethylaminosalicylaldehyde (19.3g) and diethyl malonate (18.0g) were heated under reflux in dry acetonitrile (200mL) with morpholine (20mL) as a catalyst. Ester coumarin (26.5g) was obtained by column chromatography. Hydrolyzing ester coumarin (10.0g) in 10% sodium hydroxide water/ethanol (V/V: 1/2, 200mL) mixed solution, adding dilute hydrochloric acid to adjust pH to 4-5, filtering, and recrystallizing to obtain solid carboxyl-containing coumarin (7.9 g). Coumarin (5.2g) containing carboxyl and ethylene glycol (50mL) are catalyzed by concentrated sulfuric acid (0.5mL), and the reaction is heated and stirred at 85 ℃. And (2) adding saturated sodium carbonate aqueous solution to neutralize sulfuric acid, adjusting the pH value to 7-9, extracting with dichloromethane, drying, and performing column chromatography to obtain hydroxyl-containing coumarin (4.8 g). Finally, coumarin (3.0g) containing hydroxyl and acryloyl chloride (1.0g) were dissolved in dichloromethane (100mL), triethylamine (5mL) was added to the solution in an ice-water bath, the mixture was reacted overnight at room temperature, and a blue fluorescent monomer (3.2g) of an acrylate was obtained by column chromatography.
S2, synthesizing blue fluorescent microspheres: blue fluorescent monomer (0.05g), butyl acrylate (19.0g), styrene (81.0g), divinylbenzene (0.5g), dodecylmercaptan (1.5g), wax (10.5g), dibenzoyl peroxide (5.1g), tert-butylsalicylic acid metal complex monomer (2.2g), and 20% magnesium hydroxide colloidal aqueous solution (400mL) were reacted by emulsion polymerization with heating and stirring at 85 ℃ for 9 hours. After the reaction is finished, filtering and washing to obtain the polymer microsphere with blue fluorescence, and drying in a drying oven at 30-50 ℃. The technical characteristics are shown in table 1.
S3, synthetic blue fluorescent toner: uniformly mixing the blue fluorescent microspheres (100.0g) and the nano silicon dioxide (1.0g), and then filtering through screens of 200 meshes and 300 meshes respectively to remove large particles and impurities to obtain the blue fluorescent toner.
Example 2
The embodiment relates to green fluorescent ink powder applied to laser printing, which is prepared according to the following steps:
s1, synthesizing a green fluorescent monomer: 2, 4-dimethylpyrrole (4.0g) and 4-bromobutyryl chloride (3.7g) were reacted with stirring in dry dichloromethane (100mL) at room temperature for 5 hours, triethylamine (15mL) and boron trifluoride ether (20mL) were added in this order, and the reaction was continued with stirring at room temperature for 12 hours. A precursor (3.3g) of a green fluorescent monomer was obtained by column chromatography. Finally, a precursor of the green fluorescent monomer (3.1g) and acryloyl chloride (1.0g) were dissolved in dichloromethane (100mL), triethylamine (5mL) was added to an ice-water bath, and the mixture was reacted at room temperature overnight to obtain a green fluorescent monomer (3.1g) by column chromatography.
S2, synthesizing green fluorescent microspheres: a green fluorescent monomer (0.05g) was reacted with butyl acrylate (19.0g), styrene (81.0g), divinylbenzene (0.5g), dodecylmercaptan (1.5g), wax (10.5g), dibenzoyl peroxide (5.1g), a monomer of a t-butylsalicylic acid metal complex (2.2g), and a 20% magnesium hydroxide colloidal aqueous solution (400mL) by emulsion polymerization under heating and stirring at 85 ℃ for 9 hours. After the reaction is finished, the polymer microspheres with green fluorescence are obtained by filtering and washing, and are dried in a drying oven at the temperature of 30-50 ℃. The technical characteristics are shown in table 1.
S3, synthesizing green fluorescent toner: uniformly mixing the green fluorescent microspheres (100.0g) and the nano silicon dioxide (1.0g), and then filtering through screens of 200 meshes and 300 meshes respectively to remove large particles and impurities to obtain the green fluorescent ink powder.
Example 3
The embodiment relates to a red fluorescent toner applied to laser printing, which is prepared according to the following steps:
s1, synthesis of red fluorescent monomer: piperidine (2mL) was added to a precursor of a green fluorescent monomer (3.1g) and 3, 4-dimethoxybenzaldehyde (4.0g) in dry acetonitrile (150mL) at room temperature, and the mixture was stirred under reflux for 12 hours to obtain a precursor of a red fluorescent monomer (5.1g) by column chromatography. Finally, a precursor of the red fluorescent monomer (3.0g) and acryloyl chloride (0.8g) were dissolved in dichloromethane (100mL), triethylamine (5mL) was added to an ice-water bath, and the mixture was reacted at room temperature overnight to obtain a red fluorescent monomer (3.1g) by column chromatography.
S2, synthesizing red fluorescent microspheres: a red fluorescent monomer (0.10g) was reacted with butyl acrylate (19.0g), styrene (81.0g), divinylbenzene (0.5g), dodecylmercaptan (1.5g), wax (10.5g), dibenzoyl peroxide (5.1g), a monomer of a t-butylsalicylic acid metal complex (2.2g), and a 20% magnesium hydroxide colloidal aqueous solution (400mL) by emulsion polymerization under heating and stirring at 85 ℃ for 9 hours. After the reaction is finished, filtering and washing to obtain the polymer microsphere with red fluorescence, and drying in a drying oven at 30-50 ℃. The technical characteristics are shown in table 1.
S3, synthesizing red fluorescent toner: uniformly mixing red fluorescent microspheres (100.0g) and nano silicon dioxide (1.0g), and then filtering through screens of 200 meshes and 300 meshes respectively to remove large particles and impurities to obtain the red fluorescent toner.
Comparative example 1
The comparative example relates to blue fluorescent toner applied to laser printing, namely toner prepared by a physical mixing and copolymerization method of a charge regulator, and the blue fluorescent toner is prepared by the following steps:
s1, synthesizing a blue fluorescent microsphere of a comparative example: hydroxy-containing coumarin (0.05g), butyl acrylate (19.0g), styrene (81.0g), divinylbenzene (0.5g), dodecylmercaptan (1.5g), wax (10.5g), dibenzoyl peroxide (5.1g), t-butylsalicylic acid metal complex (2.1g), and a 20% magnesium hydroxide colloidal aqueous solution (400mL) were reacted by emulsion polymerization with heating and stirring at 85 ℃ for 8 hours. After the reaction is finished, filtering and washing to obtain the blue fluorescent polymer microspheres of the comparative example, and drying in a drying oven at 30-50 ℃. The technical characteristics are shown in table 1.
S2, Synthesis of comparative example blue fluorescent toner: the comparative example blue fluorescent microspheres (100.0g) and the nano silica (1.0g) were uniformly mixed, and then filtered through 200 mesh and 300 mesh sieves, respectively, to remove large particles and impurities, to obtain the comparative example blue fluorescent toner.
Comparative example 2
The comparative example relates to a green fluorescent toner applied to laser printing, namely a toner prepared by a physical mixing and non-copolymerization method of a charge regulator, and the green fluorescent toner of the comparative example is prepared by the following steps:
s1, synthesizing green fluorescent microspheres of comparative example: a precursor of a green fluorescent monomer (0.05g) was reacted with butyl acrylate (19.0g), styrene (81.0g), divinylbenzene (0.5g), dodecylmercaptan (1.5g), wax (10.5g), dibenzoyl peroxide (5.1g), t-butylsalicylic acid metal complex (2.1g), and a 20% magnesium hydroxide colloidal aqueous solution (400mL) by emulsion polymerization under heating and stirring at 85 ℃ for 8 hours. After the reaction is finished, filtering and washing to obtain the green fluorescent polymer microsphere of the comparative example, and drying in a drying oven at 30-50 ℃. The technical characteristics are shown in table 1.
S2, Synthesis of comparative example Green fluorescent toner: the green fluorescent microspheres (100.0g) and the nano-silica (1.0g) are uniformly mixed, and then are filtered through screens of 200 meshes and 300 meshes respectively to remove large particles and impurities, so that the green fluorescent toner for the comparative example is obtained.
Comparative example 3
The comparative example relates to a red fluorescent toner applied to laser printing, namely a toner prepared by a physical mixing and non-copolymerization method of a charge regulator, and the red fluorescent toner is prepared by the following steps:
s1, synthesizing a red fluorescent microsphere of a comparative example: a precursor of a red fluorescent monomer (0.10g) was reacted with butyl acrylate (19.0g), styrene (81.0g), divinylbenzene (0.5g), dodecylmercaptan (1.5g), wax (10.5g), dibenzoyl peroxide (5.1g), t-butylsalicylic acid metal complex (2.1g), and a 20% magnesium hydroxide colloidal aqueous solution (400mL) by emulsion polymerization under heating and stirring at 85 ℃ for 8 hours. After the reaction is finished, filtering and washing to obtain the polymer microsphere with the red fluorescence of the comparative example, and drying in a drying oven at 30-50 ℃. The technical characteristics are shown in table 1.
S2, Synthesis of comparative example Red fluorescent toner: the comparative example red fluorescent microspheres (100.0g) and the nano silica (1.0g) are uniformly mixed, and then filtered through screens of 200 meshes and 300 meshes respectively to remove large particles and impurities, so that the comparative example red fluorescent toner is obtained.
Test examples
The fluorescent toner of three primary colors of blue, green and red of the examples and comparative examples was charged into a laser printer, and patterns and characters of different fluorescent colors could be printed as desired, and the technical characteristics thereof are shown in table 1.
TABLE 1 technical characteristics of fluorescent toners of examples and comparative examples
As can be seen from table 1, when the fluorescent toners of three primary colors of blue, green and red are used alone, the printed patterns and characters are almost colorless in sunlight, and show strong blue, green and red fluorescence respectively under 365nm ultraviolet light irradiation. After the fluorescent toner with the three primary colors of blue, green and red is used in combination, printed patterns and characters are almost colorless under sunlight, and can also display colorful fluorescence under the irradiation of 365nm ultraviolet light, but compared with the printed patterns and characters of the comparative examples 1, 2 and 3, the fluorescent display of the printed patterns and characters of the examples 1, 2 and 3 is better and clearer, and the printed display is more uniform.
It is to be understood that the above examples are illustrative only for the purpose of clarity of description and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. The fluorescent ink powder with uniform charge quantity is characterized by comprising fluorescent microspheres, wherein the fluorescent microspheres have a chemical structural formula as shown in formula (1) or formula (2):
2. the fluorescent toner of claim 1, wherein the fluorophores include at least one of blue fluorophores, red fluorophores, and green fluorophores.
3. The fluorescent toner according to claim 1 or 2, wherein the fluorescent microspheres are prepared by the following steps:
mixing 0.01-1% of fluorescent monomer, 20-40% of styrene, 5-10% of butyl acrylate, 0.1-0.8% of divinylbenzene, 0.5-2.5% of dodecyl mercaptan, 3-18% of wax, 1-15% of initiator, 0.5-5% of monomer with positive/negative charge groups and 40-50% of first dispersing agent for polymerization reaction.
4. The fluorescent toner of claim 3, wherein the positively/negatively charged group-bearing monomer comprises at least one of formulas (3) - (6):
wherein m and n are 1-10.
5. The fluorescent toner according to claim 3 or 4, wherein the initiator comprises at least one of potassium persulfate, azobisisobutyronitrile, dibenzoyl peroxide, lauroyl peroxide, t-butyl peroxypivalate, isopropyl peroxydicarbonate, dicyclohexyl peroxydicarbonate; and/or the first dispersing agent comprises at least one of sodium dodecyl benzene sulfonate, polyether surface active group and colloid of magnesium hydroxide, magnesium carbonate, calcium phosphate, talcum powder and the like.
6. The fluorescent toner according to any one of claims 3 to 5, wherein the polymerization is emulsion polymerization or suspension polymerization.
7. The fluorescent toner of any one of claims 1-6, further comprising a second dispersant.
8. The fluorescent toner according to claim 7, wherein the mass ratio of the fluorescent microspheres to the second dispersant is 0.1% to 1.5%.
9. The fluorescent toner of claim 7 or 8, wherein the second dispersant comprises at least one of nano-silica, alumina, titanium dioxide, magnesium silicate, calcium stearate, calcium laurate.
10. Use of a fluorescent toner according to any one of claims 1 to 9 in laser printing.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5783346A (en) * | 1996-03-06 | 1998-07-21 | Eastman Kodak Company | Toner compositions including polymer binders with adhesion promoting and charge control monomers |
| WO2005026225A1 (en) * | 2003-09-15 | 2005-03-24 | Hans-Joachim Metz | Process of making monodisperse, spherical, controlled-size micrometer polymer particles |
| US20130295500A1 (en) * | 2012-05-02 | 2013-11-07 | Dinesh Tyagi | Use of fluorescing toners for imaging |
| CN108129594A (en) * | 2017-12-20 | 2018-06-08 | 英德科迪颜料技术有限公司 | A kind of fluorescent copolymer microballoon and preparation method thereof |
| CN108129595A (en) * | 2017-12-28 | 2018-06-08 | 湖南辰砾新材料有限公司 | A kind of fluorescent copolymer microballoon and preparation method thereof |
| CN111234080A (en) * | 2020-02-11 | 2020-06-05 | 浙江理工大学 | AIE polymer nanoparticles, their preparation and use as colorants for ink-jet printing inks |
-
2021
- 2021-04-15 CN CN202110408029.3A patent/CN113156782B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5783346A (en) * | 1996-03-06 | 1998-07-21 | Eastman Kodak Company | Toner compositions including polymer binders with adhesion promoting and charge control monomers |
| WO2005026225A1 (en) * | 2003-09-15 | 2005-03-24 | Hans-Joachim Metz | Process of making monodisperse, spherical, controlled-size micrometer polymer particles |
| US20130295500A1 (en) * | 2012-05-02 | 2013-11-07 | Dinesh Tyagi | Use of fluorescing toners for imaging |
| CN108129594A (en) * | 2017-12-20 | 2018-06-08 | 英德科迪颜料技术有限公司 | A kind of fluorescent copolymer microballoon and preparation method thereof |
| CN108129595A (en) * | 2017-12-28 | 2018-06-08 | 湖南辰砾新材料有限公司 | A kind of fluorescent copolymer microballoon and preparation method thereof |
| CN111234080A (en) * | 2020-02-11 | 2020-06-05 | 浙江理工大学 | AIE polymer nanoparticles, their preparation and use as colorants for ink-jet printing inks |
Non-Patent Citations (2)
| Title |
|---|
| ZHIYUAN TIAN等: "Photoswitchable Fluorescent Nanoparticles: Preparation, Properties and Applications", 《CHEMPHYSCHEM》 * |
| ZHIYUAN TIAN等: "Twisted perylene dyes enable highly fluorescent and photostable nanoparticles", 《CHEMICAL COMMUNICATIONS》 * |
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