CN113087834A - Fluorescent ink powder and application thereof - Google Patents
Fluorescent ink powder and application thereof Download PDFInfo
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- CN113087834A CN113087834A CN202110407998.7A CN202110407998A CN113087834A CN 113087834 A CN113087834 A CN 113087834A CN 202110407998 A CN202110407998 A CN 202110407998A CN 113087834 A CN113087834 A CN 113087834A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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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
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Abstract
The invention relates to the field of ink powder, in particular to fluorescent ink powder and application thereof. The fluorescent ink powder is prepared by the following steps: mixing a fluorescent monomer, butyl acrylate, styrene, divinylbenzene, dodecyl mercaptan, wax, an initiator, a charge regulator and a first dispersing agent, carrying out polymerization reaction to obtain fluorescent microspheres, and mixing the fluorescent microspheres and a second dispersing agent to obtain the fluorescent toner. The fluorescent ink powder provided by the invention is prepared by taking the polymer microsphere prepared by a chemical copolymerization method as a core, wrapping the charge regulator in the polymer microsphere and assisting with the dispersant, and the fluorescent ink powder is uniform and stable in intensity, narrow in emission half-peak width and stable in photophysical and photochemical properties of the fluorescent group and can be suitable for laser printing.
Description
Technical Field
The invention relates to the field of ink powder, in particular to 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.
At present, fluorescence printing is almost all realized through inkjet printing, but inkjet printing exists that the printing speed is slow, the boundary definition of printing the handwriting is low, batch printing ability is relatively poor, be difficult to satisfy the shortcoming of the heavier print job of load, laser printing is as novel printing technique, it is effectual to have a printing, printing speed is fast, advantage that the noise is little, laser printing compares in inkjet printing, high speed, high efficiency, economy, the advantage of environmental protection has, but because laser printing requires its powdered ink to need the charge, the fluorescence powdered ink that can be applicable to laser printing at present is less, therefore, it has great meaning to promoting the application of fluorescence printing in anti-fake technology to develop a fluorescence powdered ink that can adapt to laser printing.
Disclosure of Invention
Therefore, the technical problem to be solved by the present invention is to overcome the defect of the prior art that the fluorescent toner suitable for laser printing is lacked, and thus, the fluorescent toner and the application thereof are provided.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
the fluorescent ink powder is prepared by the following steps:
mixing a fluorescent monomer, butyl acrylate, styrene, divinylbenzene, dodecyl mercaptan, wax, an initiator, a charge regulator and a first dispersing agent, carrying out polymerization reaction to obtain fluorescent microspheres, and mixing the fluorescent microspheres and a second dispersing agent to obtain the fluorescent toner.
Optionally, the fluorescent microspheres comprise the following raw materials in percentage by mass:
0.01-1% of fluorescent monomer, 5-10% of butyl acrylate, 20-40% of styrene, 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 charge regulator and 40-50% of first dispersant.
Optionally, the mass ratio of the fluorescent microspheres to the second dispersing agent is 0.1-1.5%.
Optionally, the fluorescent monomer includes at least one of a red fluorescent monomer, a blue fluorescent monomer, and a green fluorescent monomer.
Optionally, the initiator comprises at least one of potassium persulfate, azobisisobutyronitrile, dibenzoyl peroxide, lauroyl peroxide, tert-butyl peroxypivalate, isopropyl peroxydicarbonate, and dicyclohexyl peroxydicarbonate.
Optionally, the charge regulator comprises at least one of quaternary ammonium salt and tert-butyl salicylic acid metal complex.
Optionally, the first dispersant comprises at least one of sodium dodecyl sulfate, polyether surface active group, and colloid of magnesium hydroxide, magnesium carbonate, calcium phosphate, talcum powder, etc.
Optionally, the second dispersant includes at least one of nano-silica, alumina, titanium dioxide, magnesium silicate, calcium stearate, and calcium laurate.
Optionally, the polymerization reaction is emulsion polymerization or suspension polymerization.
The invention also provides application of the fluorescent toner in laser printing.
The technical scheme of the invention has the following advantages:
1. the fluorescent ink powder provided by the invention is prepared by taking the polymer microsphere prepared by a chemical copolymerization method as a core, wrapping the charge regulator in the polymer microsphere and assisting with the dispersant, and the fluorescent ink powder is uniform and stable in intensity, narrow in emission half-peak width and stable in photophysical and photochemical properties of the fluorescent group, and can be suitable for laser printing.
2. According to the fluorescent toner provided by the invention, the particle size, the glass transition temperature and the charged amount of the fluorescent microspheres are adjusted by limiting the mass ratio of the fluorescent monomer, the butyl acrylate, the styrene, the divinylbenzene, the dodecyl mercaptan, the wax, the initiator, the charge regulator and the first dispersing agent, so that the printing effect of the fluorescent toner is favorably presented.
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 all the reagents or instruments are conventional reagent products which can be purchased from the market.
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) 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 sodium dodecylsulfate (80g) in deionized water (500mL) 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 blue fluorescence, and drying in a drying oven at 30-50 ℃.
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 toner applied to laser printing, which is prepared according to the following steps of 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: green 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-butyl salicylic acid metal complex (2.1g) and sodium dodecylsulfate (80g) were reacted in deionized water (500mL) by emulsion polymerization with heating and stirring at 85 ℃ for 8 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 ℃.
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: 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 sodium dodecylsulfate (80g) in deionized water (500mL) 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 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 the toner prepared by a physical mixing rather than copolymerization method of fluorescent materials, 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 green fluorescent toner applied to laser printing, namely the toner prepared by a physical mixing rather than copolymerization method of fluorescent materials, 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 red fluorescent toner applied to laser printing, namely the toner prepared by a physical mixing rather than copolymerization method of fluorescent materials, 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 the three primary colors of blue, green and red of the examples and the comparative examples is loaded into a laser printer, and patterns and characters with different fluorescent colors can be printed according to requirements, and the technical characteristics 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 ink powder with the three primary colors of blue, green and red is used in combination, printed patterns and characters are almost colorless under sunlight, and colorful fluorescence can be displayed under 365nm ultraviolet light irradiation. Compared with each comparative example, the fluorescent display effect of each example is better and clearer.
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. It will be apparent to those skilled in the art that other proportions or types of fluorescent toners can be prepared by varying the fluorescent monomers, butyl acrylate, styrene, divinylbenzene, dodecylmercaptan, wax, initiator, charge control agent, first dispersant, and second dispersant as described in the above examples. And other variations and modifications may be made on the basis of the foregoing 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 is characterized by being prepared by the following steps:
mixing a fluorescent monomer, butyl acrylate, styrene, divinylbenzene, dodecyl mercaptan, wax, an initiator, a charge regulator and a first dispersing agent, carrying out polymerization reaction to obtain fluorescent microspheres, and mixing the fluorescent microspheres and a second dispersing agent to obtain the fluorescent toner.
2. The fluorescent toner according to claim 1, wherein the fluorescent microspheres comprise the following raw materials in percentage by mass:
0.01-1% of fluorescent monomer, 5-10% of butyl acrylate, 20-40% of styrene, 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 charge regulator and 40-50% of first dispersant.
3. The fluorescent toner according to claim 1 or 2, wherein the mass ratio of the fluorescent microspheres to the second dispersant is 0.1 to 1.5%.
4. The fluorescent toner of any one of claims 1-3, wherein the fluorescent monomers include at least one of red fluorescent monomers, blue fluorescent monomers, and green fluorescent monomers.
5. The fluorescent toner of any one of claims 1-4, wherein the initiator comprises at least one of potassium persulfate, azobisisobutyronitrile, dibenzoyl peroxide, lauroyl peroxide, t-butyl peroxypivalate, isopropyl peroxydicarbonate, dicyclohexyl peroxydicarbonate.
6. The fluorescent toner of any of claims 1-5, wherein the charge control agent comprises at least one of a quaternary ammonium salt, a tertiary butyl salicylic acid metal complex.
7. The fluorescent toner according to any one of claims 1 to 6, wherein the first dispersant comprises at least one of sodium lauryl sulfate, polyether type surface active groups, and colloids of magnesium hydroxide, magnesium carbonate, calcium phosphate, talc, and the like.
8. The fluorescent toner of any one of claims 1-7, wherein the second dispersant comprises at least one of nano-silica, alumina, titanium dioxide, magnesium silicate, calcium stearate, calcium laurate.
9. The fluorescent toner according to any one of claims 1 to 8, wherein the polymerization reaction is emulsion polymerization or suspension polymerization.
10. Use of the fluorescent toner according to any one of claims 1 to 9 in laser printing.
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| CN202110407998.7A CN113087834B (en) | 2021-04-15 | 2021-04-15 | Fluorescent ink powder and application thereof |
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|---|---|---|---|---|
| CN103319909A (en) * | 2013-06-19 | 2013-09-25 | 大连福思达专用化学有限公司 | Dyestuff with polymerizable group and preparation of microspheres containing dyestuff |
| CN105086629A (en) * | 2015-09-10 | 2015-11-25 | 中国科学院化学研究所 | Preparation method and application of ultraviolet fluorescent powdered ink |
| CN106873321A (en) * | 2017-04-25 | 2017-06-20 | 大连福思达专用化学有限公司 | A kind of preparation method of color toner |
| 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 |
| CN110361943A (en) * | 2019-06-12 | 2019-10-22 | 大连福思达专用化学有限公司 | A kind of preparation process of laser printer color toner |
-
2021
- 2021-04-15 CN CN202110407998.7A patent/CN113087834B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103319909A (en) * | 2013-06-19 | 2013-09-25 | 大连福思达专用化学有限公司 | Dyestuff with polymerizable group and preparation of microspheres containing dyestuff |
| CN105086629A (en) * | 2015-09-10 | 2015-11-25 | 中国科学院化学研究所 | Preparation method and application of ultraviolet fluorescent powdered ink |
| CN106873321A (en) * | 2017-04-25 | 2017-06-20 | 大连福思达专用化学有限公司 | A kind of preparation method of color toner |
| 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 |
| CN110361943A (en) * | 2019-06-12 | 2019-10-22 | 大连福思达专用化学有限公司 | A kind of preparation process of laser printer color toner |
Non-Patent Citations (1)
| Title |
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| 李医明: "《中药化学》", 31 August 2018 * |
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