CN111454589B - Disperse yellow dye composition and preparation method thereof - Google Patents
Disperse yellow dye composition and preparation method thereof Download PDFInfo
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- CN111454589B CN111454589B CN202010398145.7A CN202010398145A CN111454589B CN 111454589 B CN111454589 B CN 111454589B CN 202010398145 A CN202010398145 A CN 202010398145A CN 111454589 B CN111454589 B CN 111454589B
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- disperse yellow
- component
- yellow dye
- dye composition
- disperse
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- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 239000001043 yellow dye Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000000975 dye Substances 0.000 claims abstract description 20
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 13
- 238000004043 dyeing Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002002 slurry Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 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 4
- NMDKWAQVRNUKQH-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid formaldehyde Chemical compound C=O.C(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NMDKWAQVRNUKQH-UHFFFAOYSA-N 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
- 238000002156 mixing Methods 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 239000004117 Lignosulphonate Substances 0.000 claims 1
- 235000019357 lignosulphonate Nutrition 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- 238000000859 sublimation Methods 0.000 abstract description 13
- 230000008022 sublimation Effects 0.000 abstract description 13
- RTZYVAQWQXPIAC-UHFFFAOYSA-N 4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C(N=NC=2C=CC=CC=2)C=C1 RTZYVAQWQXPIAC-UHFFFAOYSA-N 0.000 abstract description 6
- 230000007547 defect Effects 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract description 2
- 239000000986 disperse dye Substances 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000004744 fabric Substances 0.000 description 4
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 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
- 238000001035 drying Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method 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
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
Abstract
The invention belongs to the technical field of dyes, and particularly relates to a disperse yellow dye composition which comprises a component A, a component B and an auxiliary agent, wherein the component A is represented by a formula (I)The component B is selected from one or more compounds shown in a formula (II):
Description
Technical Field
The invention belongs to the technical field of dyes, and particularly relates to a disperse yellow dye composition, a preparation method and application thereof.
Background
Traditionally, disperse yellow 23# is widely used, and although the disperse yellow 23# is economical and excellent in performance, since the disperse yellow 23# contains p-aminoazobenzene and does not meet the OKO-TEX 100 standard, various companies successively put forward a plurality of alternative products. For example, disperse yellow E-GL produced by Zhejiang Gongsheng GmbH and disperse yellow ERGFL produced by Zhejiang valley company are environment-friendly products, but have poor compatibility with other two-primary-color disperse blue 2BLN and disperse red 3B, which mainly shows yellow running and easy color running during shaping after dyeing, and the dye has poor sublimation fastness.
The development of a disperse yellow dye which is bright in color, excellent in performance, good in color matching compatibility with disperse blue 2BLN and disperse red 3B and environment-friendly, is used for replacing disperse yellow E-GL and disperse yellow ERGFL, and is a subject of urgent research in the dye industry.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a disperse yellow dye composition and a preparation method thereof, solves the defects of alkali resistance and sublimation fastness of the existing substitute disperse yellow 23# product, has the advantages of bright color light, good compatibility and wider pH value application range, and has obvious advantages of light fastness and sublimation fastness, low price, economy and environmental protection.
In order to achieve the purpose, the invention adopts the technical scheme that:
a disperse yellow dye composition comprises a component A, a component B and an auxiliary agent, wherein the component A is a compound shown as a formula (I), and the component B is one or more selected from compounds shown as a formula (II):
in the formula (II), X is selected from hydrogen and cyanoalkyl.
Preferably, X is selected from hydrogen or cyanoethyl, i.e., a compound represented by the formula (II-1) and a compound represented by the formula (II-2):
preferably, the component B contains at least one of a compound represented by the formula (II-1) and a compound represented by the formula (II-2).
More preferably, the above-mentioned component B is composed of one or both of a compound represented by the formula (II-1) and a compound represented by the formula (II-2).
When the dye compound consists of a component A and a component B, the mass percent of the component A is 40-99%, and the mass percent of the component B is 1-60%.
Preferably, the mass percent of the component A is 60-95%, and the mass percent of the component B is 5-40%.
The mass ratio of the auxiliary agent to the dye compound in the composition is 0.5-4: 1.
The auxiliary agent is a dispersing agent, a surfactant thereof and the like which are commonly used in the process of compounding disperse dyes, and is preferably one or more of the following compounds: naphthalene sulfonic acid formaldehyde condensate, lignosulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate. Examples of the dispersant include a methyl naphthalene sulfonic acid-formaldehyde condensate (dispersant MF), a naphthalene sulfonic acid-formaldehyde condensate (dispersant NNO), a benzyl naphthalene sulfonic acid-formaldehyde condensate (dispersant CNF), and sodium lignosulfonates (lignin 85A and 83A).
The invention also provides a preparation method of the disperse yellow dye composition, which comprises the steps of mixing the dye monomer compounds forming the disperse yellow dye composition according to a ratio, and carrying out microparticulation by a pulverizer in the presence of an auxiliary agent and water; or the dye monomer compound is subjected to microparticulation treatment by a pulverizer in the presence of an auxiliary agent and water respectively and then mixed in proportion.
The pulverizer is selected from a sand mill or a grinder.
The dye monomer compound and the auxiliary agent are mixed with water to prepare slurry, and the solid content of the slurry is 35-45%.
The composition of the disperse yellow dye of the invention can disperse dye products into liquid after being ground by a sand mill or a grinding mill, and can be powder and granular after being spray-dried, which is a preparation method known by the technical personnel in the field, and because 100 percent of water can not be removed in the spray-drying process, a certain amount of water can still be allowed to exist in the powder or granular dye products.
In addition, due to the particularity of the dye industry, the dye product is difficult to prepare into a pure product, and usually has impurities in the preparation process, and the dye product of the invention also allows the existence of trace impurities.
The disperse yellow dye composition provided by the invention is mainly applied to dyeing or printing of hydrophobic fiber materials.
Compared with the prior art, the invention provides a novel disperse yellow dye composition, which has the following beneficial effects: the yellow disperse dye composition provided by the invention overcomes the defects of alkali resistance and sublimation fastness of a product replacing disperse yellow 23#, and has the advantages of bright color light, good compatibility, wider pH value application range, obvious advantages of light fastness and sublimation fastness, low price, economy and environmental friendliness. Is an rare disperse yellow dye composition.
Detailed Description
The present invention is further described in the following description of the specific embodiments, which is not intended to limit the invention, but various modifications and improvements can be made by those skilled in the art based on the basic idea of the invention, but the scope of the invention is within the scope of the invention as long as they do not depart from the basic idea of the invention.
The various starting materials and reagents used in the examples of the present invention were all commercially available unless otherwise specified.
Example 1:
40 g of a compound of formula (I), 10 g of a compound of formula (II-1), 1 g of a compound of formula (II-2) and 53 g of a dispersing agent MF are mixed with 160 g of water, ground, dispersed and spray-dried to obtain a finished product, and the finished product can provide yellow color tone of fabrics.
Example 2
Disperse dyes of examples 2 to 17 were prepared as described in example 1, except that the following components A, B and auxiliaries were used in the following table, and the mixtures were blended with water to make a slurry, the solids content of the slurry was controlled to be preferably 35 to 45%, and the resulting slurry was ground, dispersed and spray dried to give a yellow shade of uniform and good fastness to fabrics. The auxiliaries in the following table are indicated in short form and are: dispersant MF i.e. methyl naphthalene sulfonic acid formaldehyde condensate, diffuser NNO i.e. naphthalene sulfonic acid formaldehyde condensate, diffuser CNF i.e. benzyl naphthalene sulfonic acid formaldehyde condensate, lignin 85A, 83A i.e. sodium lignosulfonate, to different specifications.
Table 1:
the disperse dyes prepared in the examples 1-17, the disperse yellow E-GL in the comparative example 1 and the disperse dye in the disperse yellow ERGFL in the comparative example 2 are used for treating 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 2.0%, the bath ratio is 1: and 40, adjusting the pH value of the dyeing bath to 4-5, dyeing at room temperature, heating to 130 ℃ at a 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 sample cloth color IS observed and the sublimation color fastness IS adopted by the international standard IS 0105-X11. On the basis of the dyeing method, the pH value of the dyeing bath is respectively adjusted to be 4, 5, 6, 7, 8, 9, 10, 11 and 12, the dyeing rate of the dye under different pH values is tested, and the pH value of normal dyeing is judged, and the specific table is shown in table 2:
TABLE 2
As is apparent from the test data in Table 2, the disperse dyes prepared in examples 1 to 17 can be normally dyed at a pH value in the range of 4 to 11, while the disperse dyes in comparative examples 1 and 2 can be normally dyed only at a pH value in the range of 4 to 10. The disperse dyes prepared in examples 1 to 17 have sublimation fastness of grade 3 or 3 to 4 in comparison with the dyeing on the polyester material, while the disperse dyes in comparative examples 1 and 2 have sublimation fastness of grade 2 to 3; the disperse dyes prepared in examples 1 to 17 have sublimation fastness on the comparison cotton material of grade 3 to 4 or 4, while the disperse dyes in comparative examples 1 and 2 have sublimation fastness of grade 3 only. It can be seen that the pH values at which the disperse dyes prepared in examples 1 to 17 can be normally dyed are larger than those of the disperse dyes in comparative examples 1 and 2, and the sublimation fastness of the disperse dyes prepared in examples 1 to 17 is significantly better than that of the disperse dyes in comparative examples 1 and 2. The disperse yellow dye composition provided by the invention can better replace disperse yellow E-GL and disperse yellow ERGFL.
Claims (8)
1. A disperse yellow dye composition comprises a component A, a component B and an auxiliary agent, and is characterized in that the component A is a compound shown in a formula (I), and the component B is composed of one or two of a compound shown in a formula (II-1) and a compound shown in a formula (II-2):
2. the disperse yellow dye composition according to claim 1, wherein the composition comprises 40 to 99 mass percent of the component A and 1 to 60 mass percent of the component B, based on the dye compound.
3. The disperse yellow dye composition according to claim 2, wherein the composition comprises 60 to 95 mass percent of the component A and 5 to 40 mass percent of the component B, based on the dye compound.
4. The disperse yellow dye composition according to claim 1, wherein the mass ratio of the auxiliary agent to the dye compound in the composition is 0.5-4: 1.
5. A disperse yellow dye composition according to claim 1, wherein the auxiliary agent is selected from one or more of lignosulphonates, alkylnaphthalene sulphonic acid formaldehyde condensates, naphthalene sulphonic acid formaldehyde condensates and benzylnaphthalene sulphonic acid formaldehyde condensates.
6. A method for preparing the disperse yellow dye composition according to any one of claims 1 to 5, which comprises mixing the dye monomer compounds constituting the disperse yellow dye composition according to a certain ratio, and then carrying out microparticulation by a pulverizer in the presence of an auxiliary agent and water; or the dye monomer compound is subjected to microparticulation treatment by a pulverizer in the presence of an auxiliary agent and water respectively and then mixed in proportion.
7. The preparation method of the disperse yellow dye composition according to claim 6, wherein the dye monomer compound and the auxiliary agent are blended with water to prepare a slurry, and the solid content of the slurry is 35-45%.
8. A disperse yellow dye composition according to any one of claims 1 to 5, wherein the disperse yellow dye composition is used for dyeing or printing hydrophobic fiber materials.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010398145.7A CN111454589B (en) | 2020-05-12 | 2020-05-12 | Disperse yellow dye composition and preparation method thereof |
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| CN202010398145.7A CN111454589B (en) | 2020-05-12 | 2020-05-12 | Disperse yellow dye composition and preparation method thereof |
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| Publication Number | Publication Date |
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| CN111454589A CN111454589A (en) | 2020-07-28 |
| CN111454589B true CN111454589B (en) | 2022-02-15 |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111875983B (en) * | 2020-08-24 | 2022-05-31 | 苏州市吴江区绿洲染料有限公司 | Light fastness improved disperse yellow dye mixture |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2864816A (en) * | 1956-06-21 | 1958-12-16 | Sandoz Ag | Water-insoluble monoazo dyestuffs |
| CN1257235C (en) * | 2004-05-21 | 2006-05-24 | 浙江龙盛集团股份有限公司 | Low-temperature environmentally friendly disperse dye |
| CN103205139B (en) * | 2012-01-16 | 2014-10-22 | 清华大学 | Polymerizable dye monomers, color polymer emulsion and preparation methods thereof |
| CN107057403B (en) * | 2017-05-10 | 2018-08-17 | 浙江山峪科技股份有限公司 | A kind of golden yellow disperse dye composition, disperse dyes product and its application |
| CN109370257B (en) * | 2018-12-14 | 2020-05-19 | 苏州市吴江区绿洲染料有限公司 | Alkali-resistant disperse grey dye mixture |
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