CN114517021A - Novel gray vat dye and preparation method and application thereof - Google Patents
Novel gray vat dye and preparation method and application thereof Download PDFInfo
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- CN114517021A CN114517021A CN202210225532.XA CN202210225532A CN114517021A CN 114517021 A CN114517021 A CN 114517021A CN 202210225532 A CN202210225532 A CN 202210225532A CN 114517021 A CN114517021 A CN 114517021A
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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
- C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo dyes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
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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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/78—Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
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Abstract
The invention discloses a novel gray vat dye and a preparation method and application thereof, wherein the raw materials comprise 3-bromobenzanthracene ketone and 1, 5-diaminoanthraquinone; has the advantages that: 1. the novel gray vat dye provides a new color matching scheme for commercial dyes, and enriches the selectable range of gray dyes and brown dyes; 2. the process method for preparing the novel gray vat dye is simple, the production period is short, and the product quality is high; 3. after the novel gray vat dye prepared by the invention is commercially processed, the commercial dye has small color difference, the dye uptake can reach 98 percent, the color fastness is good, and the light fastness can reach 6 grades; 4. the novel gray vat dye prepared by the invention has low sensitivity to heat, and no obvious color difference can be generated after heating, thereby overcoming the defect that the existing vat gray M dye is sensitive to heat; 5. the novel gray vat dye prepared by the invention has no obvious mottle phenomenon and good level-dyeing property after being used for dyeing.
Description
The technical field is as follows:
the invention relates to the technical field of dye preparation, in particular to a novel gray vat dye and a preparation method and application thereof.
The background art comprises the following steps:
vat dyes are excellent dyes, have the characteristics of bright color light, complete color spectrum, excellent dyeing effect fastness and high light fastness, and are extremely important dye varieties in dyeing of various textiles requiring high dyeing quality. The vat dyes mainly comprise anthraquinone vat dyes, indigoid vat dyes and heterocyclic vat dyes, wherein the anthraquinone vat dyes are the most important ones of the vat dyes. The grey is a common color, and the currently common grey vat dye has a reduction grey M (reduction black 8), but the reduction grey M has certain sensitivity to heat, the color light is green after being heated, and the color light is red after being cooled, so that color difference is easily caused; in addition, the reduced grey M has poor level dyeing effect when dyed in light color, and is not suitable for dyeing light color.
The invention content is as follows:
the first object of the present invention is to provide a novel gray vat dye.
The second purpose of the invention is to provide a preparation method of a novel gray vat dye.
The third purpose of the invention is to provide the application of the novel gray vat dye.
The first purpose of the invention is implemented by the following technical scheme: a novel gray vat dye of the formula:
The second object of the invention is implemented by the following technical solution: a preparation method of a novel gray vat dye comprises the following steps:
(1) preparation of an imine intermediate: fully mixing 3-bromobenzanthracene ketone, 1, 5-diaminoanthraquinone, a condensation catalyst and an acid-binding agent, heating to 170-260 ℃, carrying out condensation reaction for 2-6 h, cooling, filtering, washing a filter cake to be neutral, and drying to obtain an imine intermediate: 1-amino-5- (3-iminobenzanthrone) anthraquinone;
(2) imine intermediate ring-closing reaction to prepare novel gray vat dye: dissolving the imine intermediate prepared in the step (1) in an organic solvent, heating to 130-150 ℃, carrying out ring-closure reaction for 2-6 h under the action of a ring-closure catalyst, cooling, filtering, washing a filter cake to be neutral, and drying to obtain the novel gray vat dye.
Further, in the step (1), the molar ratio of the 3-bromobenzanthracene ketone to the 1, 5-diaminoanthraquinone is 1: 1.2-1.2: 1.
Further, the condensation catalyst in the step (1) is copper oxide, and the addition mass of the condensation catalyst is 0.2-1% of the total mass of the 3-bromobenzanthracene ketone and the 1, 5-diaminoanthraquinone.
Further, the acid-binding agent in the step (1) is sodium bicarbonate, and the addition mass of the acid-binding agent is 20-50% of the mass of the 3-bromobenzanthrone.
Further, the temperature reduction step in the step (1) is to naturally reduce the temperature to below 100 ℃.
Further, the organic solvent in the step (2) is n-octanol, and the addition mass of the organic solvent is 300-500% of the mass of the imine intermediate.
Further, the ring-closing catalyst in the step (2) is potassium hydroxide, and the addition mass of the ring-closing catalyst is 100-300% of the mass of the imine intermediate.
Further, the heating modes in the step (1) and the step (2) are constant temperature rise, and the temperature rise rate is 20 ℃/30 min.
Further, the temperature reduction step in the step (2) is as follows: adding water into the reaction system for dilution, introducing 0.125MPa of compressed air, cooling to 60-80 ℃, and keeping the temperature for 2-5 hours.
Further, the drying method in the step (1) and the step (2) is to use an oven to preserve heat for 4-12 hours at 105-120 ℃ or a rake dryer to preserve heat for 14-28 hours at 100-105 ℃.
The third object of the invention is implemented by the following technical scheme: an application of a novel gray vat dye in preparing a commercial dye.
The invention has the advantages that: 1. the novel gray vat dye provides a new color matching scheme for commercial dyes, and enriches the selectable range of gray dyes and brown dyes; 2. the process method for preparing the novel gray vat dye is simple, the raw materials are easy to obtain, the production period is short, and the product quality is high; 3. after the novel gray vat dye prepared by the invention is commercially processed, the commercial dye has small color difference, the dye uptake can reach 98 percent, the color fastness is good, and the light fastness can reach 6 grades; 4. the novel gray vat dye prepared by the invention has low sensitivity to heat, and no obvious color difference can be generated after heating, thereby overcoming the defect that the existing vat gray M dye is sensitive to heat; 5. after the novel grey vat dye prepared by the method is used for dyeing, no obvious mottle phenomenon can occur, and the level dyeing effect is obviously improved compared with the existing vat grey M dye.
Description of the drawings:
in order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a graph showing the effect of cloth dyed with the reduced gray M of comparative example 1 and the novel gray vat dye prepared in example 2;
FIG. 2 is a graph showing the effect of ironing a cloth dyed with the vat ash M and the novel gray vat dye prepared in example 2 in comparative example 1;
the specific implementation mode is as follows:
the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1:
a novel gray vat dye comprises 3-bromobenzoanthrone and 1, 5-diaminoanthraquinone, wherein the molar ratio of the 3-bromobenzoanthrone to the 1, 5-diaminoanthraquinone is 1: 1. The structural formula of the obtained novel gray vat dye is represented as follows:
the main chemical reactions involved in the preparation of the novel grey vat dyes are as follows:
example 2:
the preparation of the novel gray vat dye comprises the following steps:
(1) putting 140g of 3-bromobenzanthracene ketone, 120g of 1, 5-diaminoanthraquinone, 2g of copper oxide and 50g of sodium bicarbonate into a 3000ml solid phase reactor, starting the solid phase reactor, fully mixing the components, heating to 220 ℃ at the heating rate of 20 ℃/30min, carrying out condensation reaction for 6h at constant temperature, naturally cooling the obtained product to below 100 ℃, filtering, washing a filter cake to be neutral, putting the filter cake into an oven, and drying for 8h at 105 ℃ to obtain 220g of yellowish black imine intermediate: 1-amino-5- (3-iminobenzanthrone) anthraquinone;
(2) 220g of yellow-black imine intermediate, 1100g of n-octanol and 600g of potassium hydroxide are put into a 2000ml four-mouth bottle, fully stirred and mixed, heated to 130 ℃ at the heating rate of 20 ℃/30min, and subjected to ring closure reaction for 3 h; and adding 500ml of water into the four-mouth bottle, introducing 0.125MPa of compressed air, cooling the reaction system to 80 ℃, preserving the temperature for 3 hours, filtering, washing a filter cake to be neutral, placing the filter cake in a drying oven, and drying the filter cake for 8 hours at 105 ℃ to obtain the gray vat dye.
Example 3:
the preparation of a novel gray vat dye comprises the following steps:
(1) adding 140g of 3-bromobenzanthrone, 98g of 1, 5-diaminoanthraquinone, 0.48g of copper oxide and 45g of sodium bicarbonate into a 3000ml solid phase reactor, starting the solid phase reactor, fully mixing the components, heating to 170 ℃ at the heating rate of 20 ℃/30min, carrying out condensation reaction for 6h at constant temperature, naturally cooling the obtained product to below 100 ℃, filtering, washing a filter cake to be neutral, placing the filter cake in an oven, and drying for 8h at 105 ℃ to obtain 200g of yellow-black imine intermediate: 1-amino-5- (3-iminobenzanthrone) anthraquinone;
(2) 200g of yellow-black imine intermediate, 600g of n-octanol and 200g of potassium hydroxide are put into a 2000ml four-mouth bottle, fully stirred and mixed, heated to 130 ℃ at the heating rate of 20 ℃/30min, and subjected to ring closure reaction for 3 h; and adding 400ml of water into the four-mouth bottle, introducing 0.125MPa of compressed air, cooling the reaction system to 80 ℃, preserving the temperature for 3 hours, filtering, washing a filter cake to be neutral, placing the filter cake into a drying oven, and drying the filter cake for 8 hours at 105 ℃ to obtain the gray vat dye.
Example 4:
the preparation of a novel gray vat dye comprises the following steps:
(1) Adding 140g of 3-bromobenzanthrone, 108g of 1, 5-diaminoanthraquinone, 2.48g of copper oxide and 50g of sodium bicarbonate into a 3000ml solid phase reactor, starting the solid phase reactor, fully mixing the components, heating to 260 ℃ at the heating rate of 20 ℃/30min, carrying out condensation reaction for 2h at constant temperature, naturally cooling the obtained product to below 100 ℃, filtering, washing a filter cake to be neutral, placing the filter cake in an oven, and drying at 105 ℃ for 8h to obtain 210g of yellowish black imine intermediate: 1-amino-5- (3-iminobenzanthrone) anthraquinone;
(2) adding 210g of yellow-black imine intermediate, 840g of n-octanol and 420g of potassium hydroxide into a 2000ml four-mouth bottle, fully stirring and mixing, heating to 130 ℃ at the heating rate of 20 ℃/30min, and carrying out ring closure reaction for 3 h; adding 420ml of water into the four-mouth bottle, introducing 0.125MPa of compressed air, cooling the reaction system to 80 ℃, preserving the temperature for 3 hours, filtering, washing a filter cake to be neutral, placing the filter cake in a drying oven, and drying the filter cake for 8 hours at 105 ℃ to obtain the gray vat dye.
Example 5:
the novel grey vat dyes prepared in examples 2 to 4 were used to prepare commercial dyes, respectively, the processing steps being: 300g of vat dye, 150g of vat black, 25 g of vat green, 50g of vat green, 3 g of auxiliary agent MF and 600g of water are mixed to adjust the solid content to 40%, the mixture is put into a sand mill for sanding for 12 hours, the dispersibility reaches over 4 levels, and the mixture is sprayed and dried by a spray tower to obtain the commercial dye. Since the vat dyes used were the novel gray vat dyes prepared in examples 2 to 4, respectively, three commercial dyes were obtained from this example for 3 different vat dyes, respectively, and the performance of the three commercial dyes was compared with that of the vat gray M, and the comparison results are shown in table 1.
TABLE 1 comparison of the Performance of commercial dyes prepared according to the invention with that of commercial dyes of reduced grey M
The results in Table 1 show that the novel gray vat dyes prepared in examples 2 to 4 of the invention have properties comparable to those of conventional vat dyes.
Comparative example 1:
in order to further verify the level dyeing effect and the heat sensitivity of the novel gray vat dye of the invention, in the comparative example, the novel gray vat dye and the reduced ash M prepared in example 2 are respectively dyed on the cloth of the same material by the same dyeing process, the dyeing effect is shown in fig. 1, the left side in fig. 1 is the cloth dyed by the reduced ash M, and the right side is the cloth dyed by the novel gray vat dye prepared in example 2. As can be seen from fig. 1, the cloth on the right side has no noticeable mottling, is dyed more uniformly, and therefore has better level-dyeing properties, compared with the cloth on the left side.
After the two fabrics shown in fig. 1 were ironed at the same ironing temperature and ironing time, the result is shown in fig. 2, and the left side of fig. 2 shows the fabric dyed with vat dust M, and the right side shows the fabric dyed with the novel gray vat dye prepared in example 2. As can be seen from fig. 2 and fig. 1, the color of the cloth on the right side hardly changes after ironing, while the color of the cloth on the left side changes obviously, and as can be seen, compared with the vat grey M, the novel grey vat dye of the invention has low sensitivity to heat, and is not easy to generate color difference after being heated.
In addition, the production period of the traditional reduced ash M is as long as more than 40 hours, while the whole process of the novel gray reduced dye from the production to the preparation of the commercial dye only needs 15 to 18 hours, so that the production period of the invention is shorter, and the production efficiency can be greatly improved.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that are within the spirit of the present invention are intended to be included within the scope of the present invention.
Claims (12)
1. A novel grey vat dye is characterized in that the molecular formula is as follows:
2. a process for the preparation of a novel grey vat dye according to claim 1, comprising the steps of:
(1) preparation of an imine intermediate: fully mixing 3-bromobenzanthracene ketone, 1, 5-diaminoanthraquinone, a condensation catalyst and an acid-binding agent, heating to 170-260 ℃, carrying out condensation reaction for 2-6 h, cooling, filtering, washing a filter cake to be neutral, and drying to obtain an imine intermediate: 1-amino-5- (3-iminobenzanthrone) anthraquinone;
(2) imine intermediate ring-closing reaction to prepare novel gray vat dye: dissolving the imine intermediate prepared in the step (1) in an organic solvent, heating to 130-150 ℃, carrying out ring-closure reaction for 2-6 h under the action of a ring-closure catalyst, cooling, filtering, washing a filter cake to be neutral, and drying to obtain the novel gray vat dye.
3. A method for preparing a novel gray vat dye according to claim 2, wherein in step (1), the molar ratio of 3-bromobenzoanthracenone to 1, 5-diaminoanthraquinone is 1:1.2 to 1.2: 1.
4. The method for preparing a novel gray vat dye according to claim 2, wherein the condensation catalyst in step (1) is copper oxide, and the mass of the condensation catalyst is 0.2-1% of the total mass of 3-bromobenzanthrone and 1, 5-diaminoanthraquinone.
5. The method for preparing a novel gray vat dye according to claim 2, wherein the acid-binding agent in step (1) is sodium bicarbonate, and the mass of the acid-binding agent is 20-50% of the mass of 3-bromobenzanthrone.
6. The method for preparing a novel gray vat dye according to claim 2, wherein the temperature reduction step of step (1) is a natural temperature reduction to below 100 ℃.
7. The method for preparing a novel gray vat dye according to claim 2, wherein the organic solvent in step (2) is n-octanol, and the mass of the added organic solvent is 300-500% of the mass of the imine intermediate.
8. A novel gray vat dye preparation method according to claim 2, wherein the ring closure catalyst in step (2) is potassium hydroxide, and the addition mass of the ring closure catalyst is 100-300% of the mass of the imine intermediate.
9. The method for preparing a novel gray vat dye according to claim 2, wherein the heating modes in step (1) and step (2) are constant temperature rise, and the temperature rise rate is 20 ℃/30 min.
10. The method for preparing a novel gray vat dye according to claim 2, wherein the temperature reduction step in step (2) is as follows: adding water into the reaction system for dilution, introducing 0.125MPa of compressed air, cooling to 60-80 ℃, and keeping the temperature for 2-5 hours.
11. The method for preparing a novel gray vat dye according to claim 2, wherein the drying method in step (1) and step (2) is to keep the temperature at 105-120 ℃ for 4-12 h by using an oven or keep the temperature at 100-105 ℃ for 14-28 h by using a rake dryer.
12. Use of a novel grey vat dye according to claim 1 for the preparation of commercial dyes.
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| CN202210225532.XA CN114517021A (en) | 2022-03-07 | 2022-03-07 | Novel gray vat dye and preparation method and application thereof |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2530010A (en) * | 1944-09-25 | 1950-11-14 | Ciba Ltd | Vat dyestuffs |
| US2547044A (en) * | 1949-02-17 | 1951-04-03 | Gen Aniline & Film Corp | Production of benzanthrone vat dyes methylated in 9-position |
| GB852517A (en) * | 1955-11-26 | 1960-10-26 | Hoechst Ag | New vat dyestuffs of the anthraquinone series and a process for their manufacture |
| GB987372A (en) * | 1962-03-30 | 1965-03-31 | Bayer Ag | New benzanthrone dyestuffs |
| GB989747A (en) * | 1961-06-12 | 1965-04-22 | Ciba Ltd | New vat dyestuffs and process for their manufacture |
| JPS5213524A (en) * | 1975-07-22 | 1977-02-01 | Ciba Geigy Ag | Vat dyes and process for producing same and applications thereof |
| CN1100444A (en) * | 1993-08-10 | 1995-03-22 | Basf公司 | Polycyclic vat dyes |
| CN104448888A (en) * | 2014-11-29 | 2015-03-25 | 萧县凯奇化工科技有限公司 | Preparation method of vat olive green B |
-
2022
- 2022-03-07 CN CN202210225532.XA patent/CN114517021A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2530010A (en) * | 1944-09-25 | 1950-11-14 | Ciba Ltd | Vat dyestuffs |
| US2547044A (en) * | 1949-02-17 | 1951-04-03 | Gen Aniline & Film Corp | Production of benzanthrone vat dyes methylated in 9-position |
| GB852517A (en) * | 1955-11-26 | 1960-10-26 | Hoechst Ag | New vat dyestuffs of the anthraquinone series and a process for their manufacture |
| GB989747A (en) * | 1961-06-12 | 1965-04-22 | Ciba Ltd | New vat dyestuffs and process for their manufacture |
| GB987372A (en) * | 1962-03-30 | 1965-03-31 | Bayer Ag | New benzanthrone dyestuffs |
| JPS5213524A (en) * | 1975-07-22 | 1977-02-01 | Ciba Geigy Ag | Vat dyes and process for producing same and applications thereof |
| CN1100444A (en) * | 1993-08-10 | 1995-03-22 | Basf公司 | Polycyclic vat dyes |
| CN104448888A (en) * | 2014-11-29 | 2015-03-25 | 萧县凯奇化工科技有限公司 | Preparation method of vat olive green B |
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Application publication date: 20220520 |