CN113736284A - Disperse red dye composition - Google Patents
Disperse red dye composition Download PDFInfo
- Publication number
- CN113736284A CN113736284A CN202111233356.6A CN202111233356A CN113736284A CN 113736284 A CN113736284 A CN 113736284A CN 202111233356 A CN202111233356 A CN 202111233356A CN 113736284 A CN113736284 A CN 113736284A
- Authority
- CN
- China
- Prior art keywords
- disperse red
- component
- dye composition
- red dye
- auxiliary agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 239000001044 red dye Substances 0.000 title claims abstract description 35
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 239000000975 dye Substances 0.000 claims abstract description 38
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 238000004043 dyeing Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000002270 dispersing agent Substances 0.000 claims description 8
- 238000000227 grinding Methods 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 8
- 238000001694 spray drying Methods 0.000 claims description 7
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 claims description 6
- WQHQCQSAAOGHQP-UHFFFAOYSA-N formaldehyde;2-methylnaphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WQHQCQSAAOGHQP-UHFFFAOYSA-N 0.000 claims description 4
- 229920005552 sodium lignosulfonate Polymers 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 229920001732 Lignosulfonate Polymers 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- 230000007547 defect Effects 0.000 abstract description 4
- 230000000052 comparative effect Effects 0.000 description 7
- 239000004744 fabric Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- 239000000986 disperse dye Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 238000010016 exhaust dyeing Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 1
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
- C09B67/0082—Preparations of disperse dyes or solvent dyes in liquid form
-
- 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
- D06P1/16—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 using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
The invention belongs to the technical field of disperse red dyes, and relates to a disperse red dye composition which comprises a dye and an auxiliary agent, wherein the dye comprises a component A and a component B, the component A is a compound shown in a formula (I),
the component B at least comprises a compound shown as a formula (II),
wherein: r is selected from C1‑C4Alkyl group of (1). The disperse red dye composition provided by the invention overcomes the defects of poor leveling property and low lifting power of the existing disperse red 356 product, has the obvious advantages of bright color, good leveling property and high lifting power, and is low in price, economic and environment-friendly.
Description
Technical Field
The invention belongs to the technical field of disperse red dyes, and relates to a disperse red dye composition.
Background
Disperse red 356 is a dye with wide application range, and although the performance is excellent, disperse red 356 has poor leveling property and low lifting power, and is not suitable for dyeing superfine fibers. Mainly characterized in that the dyeing is easy to generate colored flowers and can not dye dark color, thereby limiting the application range of the product.
At present, a plurality of disperse scarps formed by combining benzodifuran dyes with disperse yellow 114 and other high-fastness dyes appear in the market, for example, CN101899229A/CN201610813195 is a high-fastness disperse scarp. Although disperse red 356 is also a dye of the benzodifuran class, it does not disperse a bright red, but rather a relatively bright blue red. Despite the efforts of the skilled artisan, there has been no success in developing an alternate product over disperse red 356.
Therefore, the development of a blue-disperse red having a bright color and excellent performance and a color close to that of the red 356 is an urgent subject to be studied in the dye industry.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a disperse red dye composition, which solves the defects of poor leveling property and low lifting force of the existing disperse red 356 product, has the obvious advantages of bright color, good leveling property and high lifting force, and is low in price, economic and environment-friendly.
In order to solve the above technical problems, the object of the present invention is achieved by the following technical solutions:
a disperse red dye composition comprises a dye and an auxiliary agent, wherein the dye comprises a component A and a component B,
the component A is a compound shown in a formula (I),
the component B at least comprises a compound shown as a formula (II),
wherein:
r is selected from C1-C4Alkyl group of (1).
In one of the above-mentioned disperse red dye compositions, it is preferred that said component B is composed of one or both of the compounds represented by the formulae (II-1) and (II-2),
in the disperse red dye composition, the mass percent of the component A in the dye is 30-95%, and the mass percent of the component B in the dye is 5-70%.
In the disperse red dye composition, the mass ratio of the dye to the auxiliary agent is 0.5-7: 1.
in the disperse red dye composition, an auxiliary agent is generally required to be added during application, the auxiliary agent is a dispersing agent, a surfactant thereof and the like which are commonly used during the compounding of disperse dyes, and the auxiliary agent is selected from one or more of lignosulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate and naphthalene sulfonic acid formaldehyde condensate. Examples of the organic solvent include a methyl naphthalenesulfonic acid-formaldehyde condensate (dispersant MF), a naphthalenesulfonic acid-formaldehyde condensate (dispersant NNO), and sodium lignosulfonates (lignin NA, 83A).
The invention also provides a preparation method of the disperse red dye composition, which comprises the following steps: mixing the dye monomer compounds (crude dyes) of the composition for forming the disperse red dye according to a ratio, and then carrying out microparticulation by a grinder such as a sand mill or a grinding machine in the presence of an auxiliary agent and water; alternatively, the dye monomer compound may be subjected to a pulverization treatment using a pulverizer such as a sand mill or a grinder in the presence of an auxiliary agent or water, and then mixed in a certain proportion. The composition of the disperse red dye of the invention disperses the dye product into liquid after being ground by a sand mill or a grinding mill, and can be powder and granular after being spray-dried, and because 100 percent of water cannot be removed in the spray-drying process, a certain amount of water is still allowed to exist in the powder or granular dye product.
Due to the particularity of the dye industry, the dye product is difficult to prepare into a pure product, usually has impurities in the preparation process, and the dye product of the invention also allows the existence of trace impurities.
Specifically, the disperse red dye composition of the present invention can be prepared using the following two methods:
in the above-mentioned disperse red dye composition, the disperse red dye composition is prepared by the following method: and adding water into the component A, the component B and the dispersant MF, mixing, grinding, dispersing, and spray drying to obtain the finished product.
Alternatively, in the above-mentioned one disperse red dye composition, the disperse red dye composition is prepared by the following method: and adding water into the component A, the component B and an auxiliary agent, mixing and blending to prepare slurry, controlling the solid content of the slurry to be 35-45%, grinding and dispersing the slurry, and performing spray drying to obtain a finished product, wherein the auxiliary agent is one or more of a methyl naphthalene sulfonic acid formaldehyde condensate, a naphthalene sulfonic acid formaldehyde condensate and sodium lignosulfonate.
The disperse red dye composition provided by the invention is mainly applied to dyeing or printing of hydrophobic fiber materials.
Compared with the prior art, the invention has the following beneficial effects:
the disperse red dye composition provided by the invention has disperse blue light red which is close to disperse red 356, simultaneously solves the defects of poor leveling property and low lifting power of a disperse red 356 product, has the obvious advantages of bright color, good leveling property and high lifting power, is low in price, economical and environment-friendly, and is an rare disperse red dye composition.
Detailed Description
The present invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. Further, modifications to the invention, as would be obvious to those of ordinary skill in the art, are intended to be included within the scope of the present invention as defined by the following claims and their equivalents.
Example 1:
a finished product is obtained by mixing 7.8 g of a compound of formula (I), 1.1 g of a compound of formula (II-1), 1.1 g of a compound of formula (II-2) and 53 g of a dispersing agent MF with 62 g of water, grinding, dispersing and spray drying, and the finished product can provide a red color tone for fabrics.
Examples 2 to 11
The weight ratio of the component A to the component B in the table 1 and the auxiliary agent are adopted, water is added for blending to prepare slurry, the solid content of the slurry is controlled to be 35-45%, grinding and dispersing are carried out, spray drying are carried out, and the finished product is prepared and can provide uniform red color tone with good fastness performance for fabrics. The auxiliary agent is a methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF), a naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), sodium lignin sulfonate (lignin NA, 83A) or the like.
Table 1:
performance testing
The disperse dyes prepared in the above examples 1 to 11 and the disperse red 356 disperse dye of the comparative example 1 are treated on the polyester fabric by a conventional high-temperature high-pressure dyeing method, wherein in the treatment process, the dyeing depth (o.w.f) is controlled to be 3.0%, and the bath ratio is 1: 40, adjusting the pH value of the dyeing bath to 4-5, dyeing at room temperature, heating to 130 ℃ at the speed of 1 ℃/min, keeping the temperature for 45min, reducing, cleaning, washing, drying and cooling to 70 ℃ according to a conventional method, and taking out.
The migration dye value was tested using the national standard GB10663-89 migration dye test method.
The lifting force test, on the basis of this dyeing method, with superfine fiber's cloth, respectively dye 2%, 4%, 8% degree of depth, the test dyestuff uses 2% degree of depth as the standard, tests the rate of dyeing condition of 4%, 8% degree of depth, judges the height of dyestuff lifting force, specifically see table 2:
TABLE 2
As can be seen from the color one of Table 2, comparative example 1 and examples 1-11 are both disperse blue Red, indicating that the products of examples 1-11 can be a good replacement for disperse Red 356.
As can be seen from the one-item exhaust dyeing values of table 2, the exhaust dyeing value of comparative example 1 is only 15%. The dye transfer values of the cloth samples of the dyes of the examples 1 to 11 after dyeing reach 40 percent or more, so the dye of the examples 1 to 11 has the leveling property which is greatly higher than that of the dye of the comparative example 1, and the dyeing is not easy to generate the color.
As can be seen from the lifting force items in Table 2, the dyes of comparative example 1 exhibited 137% dyeing degree at 4% depth and 170% dyeing degree at 8% depth, whereas the dyes of examples 1 to 11 exhibited about 200% dyeing degree at 4% depth and about 350% dyeing degree at 8% depth, both of the dyes of comparative examples 1 to 11 exhibited a much higher lifting force than the dyes of comparative example 1.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (8)
1. A disperse red dye composition comprises a dye and an auxiliary agent, wherein the dye comprises a component A and a component B,
the component A is a compound shown in a formula (I),
the component B at least comprises a compound shown as a formula (II),
wherein:
r is selectedFrom C1-C4Alkyl group of (1).
2. A disperse red dye composition according to claim 1, wherein said component B is composed of one or both of the compounds represented by the formulae (II-1) and (II-2),
3. a disperse red dye composition according to claim 2, wherein the mass percent of component A in the dye is 30-95%, and the mass percent of component B is 5-70%.
4. A disperse red dye composition according to claim 2, wherein the mass ratio of the dye to the auxiliary agent is 0.5-7: 1.
5. a disperse red dye composition according to claim 2, wherein said auxiliary agent is selected from one or more of lignosulfonate, alkylnaphthalenesulfonic acid-formaldehyde condensate and naphthalenesulfonic acid-formaldehyde condensate.
6. A disperse red dye composition according to any one of claims 1 to 5, wherein said disperse red dye composition is prepared by the following method: and adding water into the component A, the component B and the dispersant MF, mixing, grinding, dispersing, and spray drying to obtain the finished product.
7. A disperse red dye composition according to any one of claims 1 to 5, wherein said disperse red dye composition is prepared by the following method: and adding water into the component A, the component B and an auxiliary agent, mixing and blending to prepare slurry, controlling the solid content of the slurry to be 35-45%, grinding and dispersing the slurry, and performing spray drying to obtain a finished product, wherein the auxiliary agent is one or more of a methyl naphthalene sulfonic acid formaldehyde condensate, a naphthalene sulfonic acid formaldehyde condensate and sodium lignosulfonate.
8. A disperse red dye composition according to any one of claims 1 to 5, wherein said disperse red dye composition is used for dyeing or printing hydrophobic fiber materials.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111233356.6A CN113736284B (en) | 2021-10-22 | 2021-10-22 | Disperse red dye composition |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111233356.6A CN113736284B (en) | 2021-10-22 | 2021-10-22 | Disperse red dye composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113736284A true CN113736284A (en) | 2021-12-03 |
| CN113736284B CN113736284B (en) | 2023-09-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111233356.6A Active CN113736284B (en) | 2021-10-22 | 2021-10-22 | Disperse red dye composition |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113736284B (en) |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07157682A (en) * | 1993-12-09 | 1995-06-20 | Mitsubishi Kasei Hoechst Kk | Disperse dye mixture |
| US5529586A (en) * | 1993-08-26 | 1996-06-25 | Sumitomo Chemical Company, Limited | Compositions containing a benzodifuranone compound and methods for coloring hydrophobic materials using the same |
| CN1631990A (en) * | 2004-11-10 | 2005-06-29 | 浙江龙盛集团股份有限公司 | Disperse red dye composition |
| CN101899229A (en) * | 2010-06-29 | 2010-12-01 | 浙江龙盛染料化工有限公司 | Disperse red dye composition |
| CN102471996A (en) * | 2009-08-21 | 2012-05-23 | 德司达染料德国有限责任公司 | Disperse dye mixtures, their preparation and use |
| CN106433213A (en) * | 2016-09-09 | 2017-02-22 | 浙江山峪染料化工有限公司 | Disperse red dye composition and dye product |
| CN108165051A (en) * | 2018-02-05 | 2018-06-15 | 浙江山峪科技股份有限公司 | A kind of high distillation is high to wash yellowish-brown disperse dye composition, dye preparations and application |
| KR20190096125A (en) * | 2018-02-08 | 2019-08-19 | (주)경인양행 | Disperse dyes composites and methods of dyeing fiber using the same |
| CN110791119A (en) * | 2019-11-08 | 2020-02-14 | 江苏海洋大学 | Method for preparing disperse red SBWF |
| CN111117291A (en) * | 2019-03-21 | 2020-05-08 | 浙江龙盛集团股份有限公司 | Disperse red dye composition and dye product |
-
2021
- 2021-10-22 CN CN202111233356.6A patent/CN113736284B/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5529586A (en) * | 1993-08-26 | 1996-06-25 | Sumitomo Chemical Company, Limited | Compositions containing a benzodifuranone compound and methods for coloring hydrophobic materials using the same |
| JPH07157682A (en) * | 1993-12-09 | 1995-06-20 | Mitsubishi Kasei Hoechst Kk | Disperse dye mixture |
| CN1631990A (en) * | 2004-11-10 | 2005-06-29 | 浙江龙盛集团股份有限公司 | Disperse red dye composition |
| CN102471996A (en) * | 2009-08-21 | 2012-05-23 | 德司达染料德国有限责任公司 | Disperse dye mixtures, their preparation and use |
| CN101899229A (en) * | 2010-06-29 | 2010-12-01 | 浙江龙盛染料化工有限公司 | Disperse red dye composition |
| CN106433213A (en) * | 2016-09-09 | 2017-02-22 | 浙江山峪染料化工有限公司 | Disperse red dye composition and dye product |
| CN108165051A (en) * | 2018-02-05 | 2018-06-15 | 浙江山峪科技股份有限公司 | A kind of high distillation is high to wash yellowish-brown disperse dye composition, dye preparations and application |
| KR20190096125A (en) * | 2018-02-08 | 2019-08-19 | (주)경인양행 | Disperse dyes composites and methods of dyeing fiber using the same |
| CN111117291A (en) * | 2019-03-21 | 2020-05-08 | 浙江龙盛集团股份有限公司 | Disperse red dye composition and dye product |
| CN110791119A (en) * | 2019-11-08 | 2020-02-14 | 江苏海洋大学 | Method for preparing disperse red SBWF |
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Effective date of registration: 20231017 Address after: 333300 Tashan Industrial Zone, Leping Industrial Park, Jingdezhen City, Jiangxi Province Patentee after: LEPING SAFELY PHARMACEUTICAL Co.,Ltd. Address before: 318000 three mountain village, Jiaojiang District, Taizhou, Zhejiang Patentee before: Zhejiang Shanyu Group Co.,Ltd. |
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