CN112176738A - Plastic colorant 2N blue and preparation method thereof - Google Patents
Plastic colorant 2N blue and preparation method thereof Download PDFInfo
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- CN112176738A CN112176738A CN202011217933.8A CN202011217933A CN112176738A CN 112176738 A CN112176738 A CN 112176738A CN 202011217933 A CN202011217933 A CN 202011217933A CN 112176738 A CN112176738 A CN 112176738A
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- 239000003086 colorant Substances 0.000 title claims abstract description 33
- 239000004033 plastic Substances 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 42
- 239000012043 crude product Substances 0.000 claims abstract description 41
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 claims abstract description 39
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 32
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims description 40
- 238000006482 condensation reaction Methods 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 15
- 230000007935 neutral effect Effects 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 13
- 238000005406 washing Methods 0.000 claims description 12
- 238000007670 refining Methods 0.000 claims description 11
- 239000012065 filter cake Substances 0.000 claims description 7
- 238000003828 vacuum filtration Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 238000007086 side reaction Methods 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- OCQDPIXQTSYZJL-UHFFFAOYSA-N 1,4-bis(butylamino)anthracene-9,10-dione Chemical group O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCCC)=CC=C2NCCCC OCQDPIXQTSYZJL-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229930182559 Natural dye Natural products 0.000 description 1
- 101100137008 Streptomyces hygroscopicus Pmms gene Proteins 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- 229920000434 poly[(mercaptopropyl)methylsiloxane] polymer Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2300/00—Characterised by the use of unspecified polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a plastic colorant 2N blue, wherein the plastic colorant 2N blue is prepared from a 2N blue crude product, an auxiliary agent and water; wherein the 2N blue crude product is prepared from 215 parts by weight of 15-25% methanol 210-one, 4-6 parts by weight of 25-35% sodium hydroxide liquid alkali, 42-44 parts by weight of 1, 4-dihydroxy anthraquinone, 84-86 parts by weight of N-butylamine and 1-2 parts by weight of catalyst; the auxiliary agent and the 2N blue crude product are 2:3-5 in parts by weight; the auxiliary agent is 20-30% of butanol. Preferably, the molar ratio of the 1, 4-dihydroxyanthraquinone to the n-butylamine is 1: 2. The yield of the 2N blue prepared by the method reaches more than 96 percent, the side reaction is less, and the purity is more than 98 percent.
Description
Technical Field
The invention relates to the technical field of plastic colorants and preparation methods thereof, in particular to a plastic colorant 2N blue and a preparation method thereof.
Background
Dyes are substances that can color fibers and other materials, and are classified into two broad categories, natural dyes and synthetic dyes. When dyeing, the dye is first prepared into water solution, organic solution, suspension and other dye liquid, and when the dye liquid is used in dyeing fiber, dye molecule is first transferred from the dye liquid to the fiber and other dyed matter via adsorption, diffusion and other chemical or physical chemical effect to color the fiber.
The 2N blue is solvent blue 35, which is named as solvent blue 2N, is a dye with a chemical name of 1, 4-di (1-butylamino) anthraquinone, is a solvent dye with excellent performance, and is mainly suitable for coloring various resins such as ABS, PC, HIPS, PMMS and the like. The molecular formula is C22H26N2O2And the molecular weight is 350.454. The structural formula of the solvent blue 35 is shown as (I):
the existing production process has the problems of low reaction speed in the condensation stage, low yield, difficult temperature rise and the like, the main content of the 2N blue product on the market is 70-80%, the purity is general, the yield is low, more byproducts are generated, and the quality of the product is difficult to ensure.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a plastic colorant 2N blue and a preparation method thereof, and the prepared 2N blue has high yield, few byproducts and high purity.
The technical scheme of the invention is realized as follows:
a plastic colorant 2N blue, wherein the plastic colorant 2N blue is prepared from a 2N blue crude product, an auxiliary agent and water; wherein,
the 2N blue crude product is prepared from 215 parts by weight of 15-25% methanol 210-one, 4-6 parts by weight of 25-35% sodium hydroxide liquid alkali, 42-44 parts by weight of 1, 4-dihydroxy anthraquinone, 84-86 parts by weight of N-butylamine and 1-2 parts by weight of catalyst; the auxiliary agent and the 2N blue crude product are 2:3-5 in parts by weight; the auxiliary agent is 20-30% of butanol.
Preferably, the catalyst is an aromatic acid.
Preferably, the molar ratio of the 1, 4-dihydroxyanthraquinone to the n-butylamine is 1: 2.
A preparation method of a plastic colorant 2N blue comprises the following specific steps:
the plastic colorant 2N blue is prepared by refining a 2N blue crude product and butanol at 90-100 ℃, performing suction filtration, washing with hot water at 75-85 ℃ until the pH value is neutral, and drying to obtain a finished product.
The 2N blue crude product is prepared by the following method: sucking methanol and liquid caustic soda into a condensation reaction kettle, stirring at the stirring speed of 60-70r/min, adding 1, 4-dihydroxy anthraquinone, N-butylamine and a catalyst, adjusting the micro-positive pressure in the reaction kettle to be 0.04-0.08MPa, heating to 60-70 ℃, keeping the temperature and stirring for 9-11 hours, cooling to 25-40 ℃ after the condensation reaction is completed, carrying out vacuum filtration, and washing a filter cake to be neutral by using hot water at the temperature of 75-85 ℃ to obtain a 2N blue crude product.
Preferably, the methanol and the liquid caustic soda are sucked into a condensation reaction kettle, then the 1, 4-dihydroxy anthraquinone, the N-butylamine and the catalyst are added, the micro-positive pressure in the reaction kettle is adjusted to be 0.04MPa, the temperature is raised to about 65 ℃, the temperature is kept for 10 hours, after the condensation reaction is completed, the reaction kettle is cooled to below 40 ℃ for vacuum filtration, and a filter cake is washed to be neutral by hot water at about 80 ℃ to obtain a 2N blue crude product.
Preferably, the temperature is raised to 60-70 ℃, the stirring speed is 80-100r/min, the stirring time is 4 hours, the stirring speed is increased to 150-.
Preferably, the 2N blue crude product is put into a refining kettle, refined by butanol at 95 ℃, filtered, washed by hot water at 80 ℃ to be neutral, and dried by a vacuum drying oven to obtain a finished product.
Preferably, the weight part ratio of the auxiliary agent to the 2N blue crude product is 1: 2.
Preferably, the adjuvant is 25% butanol.
The chemical reaction in the preparation process is as follows: condensation of
The invention has the following beneficial effects: the invention relates to a plastic colorant 2N blue and a preparation method thereof, wherein 1, 4-dihydroxy anthraquinone, N-butylamine and a catalyst are simultaneously added in a condensation stage, and the molar ratio of the 1, 4-dihydroxy anthraquinone to the N-butylamine is 1: 2; the micro-positive pressure in the reaction kettle is adjusted to be 0.04-0.08MPa, the temperature is raised to 60-70 ℃ in the heat preservation reaction stage, the stirring speed is 80-100r/min, the stirring time is 4 hours, the stirring speed is increased to 150-200r/min, and the stirring is carried out for 6 hours, so that the yield of the prepared 2N blue can reach more than 96%, the side reaction is less, and the purity is more than 98%.
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 2N blue, wherein the plastic colorant 2N blue is prepared from a 2N blue crude product, an auxiliary agent and water; wherein,
preferably, the 2N blue crude product is prepared by 212 parts of 20% methanol, 5 parts of 30% sodium hydroxide liquid alkali, 43 parts of 1, 4-dihydroxy anthraquinone, the adding amount of N-butylamine and 1, 4-dihydroxy anthraquinone according to the molar ratio of 2:1 and 1.5 parts of catalyst aromatic acid according to parts by weight; the auxiliary agent and the 2N blue crude product are 1:2 in parts by weight; the auxiliary agent is 25% of butanol.
A preparation method of a plastic colorant 2N blue comprises the following specific steps:
(1) the 2N blue crude product is prepared by the following method: sucking methanol and liquid caustic soda into a condensation reaction kettle, starting stirring at the stirring speed of 65r/min, simultaneously adding 1, 4-dihydroxy anthraquinone, n-butylamine and a catalyst, adjusting the micro-positive pressure in the reaction kettle to be 0.04MPa, heating to 65 ℃, stirring at the stirring speed of 90r/min for 4 hours, increasing the stirring speed to be 180r/min, and stirring for 6 hours. After the condensation reaction is completed, cooling to 40 ℃ for vacuum filtration, and washing a filter cake to be neutral by using hot water at 80 ℃ to obtain a 2N blue crude product.
(2) And (2) putting the 2N blue crude product prepared in the step (1) into a refining kettle, refining with butanol at 95 ℃, carrying out suction filtration, washing with hot water at 80 ℃ to be neutral, and drying the washed product by using a vacuum drying oven to obtain a finished product. The content was found to be 98.8%, the yield was 96.9%.
Example 2
A plastic colorant 2N blue, wherein the plastic colorant 2N blue is prepared from a 2N blue crude product, an auxiliary agent and water; wherein,
the 2N blue crude product is prepared from 210 parts of 25% methanol, 4 parts of 35% sodium hydroxide liquid alkali, 44 parts of 1, 4-dihydroxy anthraquinone, 84 parts of N-butylamine and 2 parts of catalyst aromatic acid in parts by weight; the auxiliary agent and the 2N blue crude product are in a weight part ratio of 2: 3; the auxiliary agent is 30% butanol.
A preparation method of a plastic colorant 2N blue comprises the following specific steps:
(1) the 2N blue crude product is prepared by the following method: sucking methanol and liquid caustic soda into a condensation reaction kettle, starting stirring at the stirring speed of 70r/min, simultaneously adding 1, 4-dihydroxy anthraquinone, n-butylamine and a catalyst, adjusting the micro-positive pressure in the reaction kettle to be 0.06MPa, heating to 60 ℃, stirring at the stirring speed of 100r/min for 6 hours, increasing the stirring speed to be 150r/min, and stirring for 3 hours. After the condensation reaction is completed, cooling to 35 ℃ for vacuum filtration, and washing a filter cake to be neutral by using 75 hot water to obtain a 2N blue crude product.
(2) And (2) putting the 2N blue crude product prepared in the step (1) into a refining kettle, refining the crude product by using butanol at 100 ℃, performing suction filtration, washing the refined product to be neutral by using hot water at 75 ℃, and drying the washed product by using a vacuum drying oven to obtain a finished product, wherein the measured content is 98.6%, and the yield is 96.3%.
Example 3
A plastic colorant 2N blue, wherein the plastic colorant 2N blue is prepared from a 2N blue crude product, an auxiliary agent and water; wherein,
the 2N blue crude product is prepared from 215 parts by weight of 15% methanol, 6 parts by weight of 25% sodium hydroxide liquid alkali, 42 parts by weight of 1, 4-dihydroxy anthraquinone, 86 parts by weight of N-butylamine and 1 part by weight of aromatic acid serving as a catalyst; the auxiliary agent and the 2N blue crude product are in a weight part ratio of 2: 5; the auxiliary agent is 20% butanol.
A preparation method of a plastic colorant 2N blue comprises the following specific steps:
(1) the 2N blue crude product is prepared by the following method: sucking methanol and liquid caustic soda into a condensation reaction kettle, starting stirring at the stirring speed of 60r/min, simultaneously adding 1, 4-dihydroxy anthraquinone, n-butylamine and a catalyst, adjusting the micro-positive pressure in the reaction kettle to be 0.08MPa, heating to 70 ℃, stirring at the stirring speed of 80r/min for 5 hours, increasing the stirring speed to be 200r/min, and stirring for 6 hours. After the condensation reaction is completed, cooling to 25 ℃ for vacuum filtration, and washing a filter cake to be neutral by using hot water at 85 ℃ to obtain a 2N blue crude product.
(2) And (2) putting the 2N blue crude product prepared in the step (1) into a refining kettle, refining the crude product by using butanol at 90 ℃, performing suction filtration, washing the refined product to be neutral by using hot water at 85 ℃, and drying the washed product by using a vacuum drying oven to obtain a finished product, wherein the measured content is 98.7%, and the yield is 96.4%.
Comparative example 1
The raw material proportion and the preparation method of the embodiment 1 are selected, and the only difference is that in the step (1), methanol and liquid caustic soda are sucked into a condensation reaction kettle and stirred at the stirring speed of 100 r/min; the other preparation steps are the same, the content is 97.9 percent, and the yield is 75.9 percent.
Comparative example 2
The raw material proportion and the preparation method of the embodiment 1 are selected, and the only difference is that the temperature in the step (1) is raised to 70 ℃, the stirring speed is 200r/min, the stirring time is 5 hours, the stirring speed is reduced to 80r/min, and the stirring is carried out for 6 hours; the other preparation steps are the same, the content is measured to be 98.1%, and the yield is 75.8%.
Comparative example 3
The raw material proportion and the preparation method of the embodiment 1 are selected, the only difference is that the 1, 4-dihydroxy anthraquinone and the n-butylamine in the raw materials are added according to the mol ratio of 1:3, the other preparation steps are the same, the content is 97.0 percent, and the yield is 76.1 percent.
Comparative example 4
Selecting the raw material proportion and the preparation method of the embodiment 1, wherein the only difference is that the micro-positive pressure in the reaction kettle in the step (2) is adjusted to be 0.1 MPa; the other preparation steps are the same, and the content is 96.8 percent, and the yield is 75.6 percent.
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 2N blue, characterized by: the plastic colorant 2N blue is prepared from a 2N blue crude product, an auxiliary agent and water; wherein,
the 2N blue crude product is prepared from 215 parts by weight of 15-25% methanol 210-one, 4-6 parts by weight of 25-35% sodium hydroxide liquid alkali, 42-44 parts by weight of 1, 4-dihydroxy anthraquinone, 84-86 parts by weight of N-butylamine and 1-2 parts by weight of catalyst;
the auxiliary agent and the 2N blue crude product are 2:3-5 in parts by weight;
the auxiliary agent is 20-30% of butanol.
2. A plastic colorant 2N blue according to claim 1, characterized in that: the catalyst is aromatic acid.
3. A plastic colorant 2N blue according to claim 1, characterized in that: the molar ratio of the 1, 4-dihydroxy anthraquinone to the n-butylamine is 1: 2.
4. A plastic colorant 2N blue according to claim 1, characterized in that: the plastic colorant 2N blue is prepared by refining a 2N blue crude product and butanol at 90-100 ℃, performing suction filtration, washing with hot water at 75-85 ℃ until the pH value is neutral, and drying to obtain a finished product.
5. A plastic colorant 2N blue according to claim 1, characterized in that: the 2N blue crude product is prepared by the following method: sucking methanol and liquid caustic soda into a condensation reaction kettle, stirring at the stirring speed of 60-70r/min, adding 1, 4-dihydroxy anthraquinone, N-butylamine and a catalyst into the reaction kettle, adjusting the micro-positive pressure in the reaction kettle to be 0.04-0.08MPa, heating to 60-70 ℃, keeping the temperature and stirring for 9-11 hours, cooling to 25-40 ℃ after the condensation reaction is completed, carrying out vacuum filtration, and washing a filter cake to be neutral by using hot water at 75-85 ℃ to obtain a 2N blue crude product.
6. A plastic colorant 2N blue according to claim 5, characterized in that: sucking methanol and liquid caustic soda into a condensation reaction kettle, adding 1, 4-dihydroxy anthraquinone, N-butylamine and a catalyst, adjusting the micro-positive pressure in the reaction kettle to be 0.04MPa, heating to about 65 ℃, preserving heat for 10 hours, cooling to below 40 ℃ after the condensation reaction is completed, carrying out vacuum filtration, and washing a filter cake to be neutral by hot water at about 80 ℃ to obtain a 2N blue crude product.
7. A plastic colorant 2N blue according to claim 6, characterized in that: the temperature is increased to 60-70 ℃, the stirring speed is 80-100r/min, the stirring time is 4 hours, the stirring speed is increased to 150-200r/min, and the stirring time is 6 hours.
8. A plastic colorant 2N blue according to claim 4, characterized in that: and (2) putting the 2N blue crude product into a refining kettle, refining with butanol at 95 ℃, performing suction filtration, washing with hot water at 80 ℃ to be neutral, and drying the washed product by using a vacuum drying oven to obtain a finished product.
9. A plastic colorant 2N blue according to claim 1, characterized in that: the auxiliary agent and the 2N blue crude product are 1:2 in parts by weight; the auxiliary agent is 25% of butanol.
10. A plastic colorant 2N blue according to claim 1, characterized in that: the auxiliary agent is 25% of butanol.
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| CN202011217933.8A CN112176738A (en) | 2020-11-04 | 2020-11-04 | Plastic colorant 2N blue and preparation method thereof |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB461428A (en) * | 1935-07-09 | 1937-02-09 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of n-substitution products of 1.4-diaminoanthraquinones |
| CN101063002A (en) * | 2006-04-26 | 2007-10-31 | 沈阳化工研究院 | Anthraquinone type solvent dye and preparation and application thereof |
| CN104341790A (en) * | 2014-09-25 | 2015-02-11 | 宁波龙欣精细化工有限公司 | Purified 1-hydroxy-4-arylamino-anthraquinone product and preparation method thereof |
| CN104725252A (en) * | 2013-12-21 | 2015-06-24 | 江苏道博化工有限公司 | Method for preparing solvent blue 35 |
| CN104725251A (en) * | 2013-12-21 | 2015-06-24 | 江苏道博化工有限公司 | Method for preparing solvent blue 78 |
| CN106008239A (en) * | 2016-05-20 | 2016-10-12 | 盐城工学院 | Production method of solvent blue 35 |
| CN108624078A (en) * | 2018-07-04 | 2018-10-09 | 安徽清科瑞洁新材料有限公司 | A kind of single bath process production method of 22 dyestuff of solvent blue 19 |
| CN111087831A (en) * | 2019-12-20 | 2020-05-01 | 南京金浩医药科技有限公司 | Preparation method of novel anthraquinone solvent blue dye |
-
2020
- 2020-11-04 CN CN202011217933.8A patent/CN112176738A/en not_active Withdrawn
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB461428A (en) * | 1935-07-09 | 1937-02-09 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of n-substitution products of 1.4-diaminoanthraquinones |
| CN101063002A (en) * | 2006-04-26 | 2007-10-31 | 沈阳化工研究院 | Anthraquinone type solvent dye and preparation and application thereof |
| CN104725252A (en) * | 2013-12-21 | 2015-06-24 | 江苏道博化工有限公司 | Method for preparing solvent blue 35 |
| CN104725251A (en) * | 2013-12-21 | 2015-06-24 | 江苏道博化工有限公司 | Method for preparing solvent blue 78 |
| CN104341790A (en) * | 2014-09-25 | 2015-02-11 | 宁波龙欣精细化工有限公司 | Purified 1-hydroxy-4-arylamino-anthraquinone product and preparation method thereof |
| CN106008239A (en) * | 2016-05-20 | 2016-10-12 | 盐城工学院 | Production method of solvent blue 35 |
| CN108624078A (en) * | 2018-07-04 | 2018-10-09 | 安徽清科瑞洁新材料有限公司 | A kind of single bath process production method of 22 dyestuff of solvent blue 19 |
| CN111087831A (en) * | 2019-12-20 | 2020-05-01 | 南京金浩医药科技有限公司 | Preparation method of novel anthraquinone solvent blue dye |
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Application publication date: 20210105 |