CN110845864B - Disperse dark blue-to-black dye composition, dye product and application thereof - Google Patents
Disperse dark blue-to-black dye composition, dye product and application thereof Download PDFInfo
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- CN110845864B CN110845864B CN201911161478.1A CN201911161478A CN110845864B CN 110845864 B CN110845864 B CN 110845864B CN 201911161478 A CN201911161478 A CN 201911161478A CN 110845864 B CN110845864 B CN 110845864B
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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
- C09B67/0033—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
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- 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
-
- 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
- D06P1/19—Nitro dyes
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- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- 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
- D06P3/82—Textiles which contain different kinds of fibres
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention discloses a disperse dark blue to black dye composition, which comprises a component A, a component B and a component C, wherein the component A is selected from at least one compound shown in a formula (I), the component B is selected from at least one compound shown in a formula (II), and the component C is selected from at least one compound shown in a formula (III). The disperse dark blue to black dye composition provided by the invention has the characteristics of excellent friction resistance, washing resistance, sublimation fastness and the like when being applied to dyeing of hydrophobic fiber materials.
Description
(I) technical field
The invention relates to a disperse dark blue-black dye composition, a dye product thereof and application of the dye product to hydrophobic fiber materials, in particular to application to dyeing of polyester and blended fabrics thereof.
(II) background of the invention
With the development of polyester and blended fabrics thereof, particularly in recent years, spandex-containing elastic fabrics are very popular in domestic and foreign markets, the products have excellent resilience, soft hand feeling and comfortable wearing, are easy to absorb sweat and can not generate static electricity, the fabrics are mainly dyed by disperse dyes, but the general disperse dyes have high affinity and good dyeability to spandex, so that the disperse dyes are seriously stained to the spandex. During the fastness test, disperse dyes stained on spandex are easy to migrate out of the fiber, and the wet treatment fastness of the terylene/spandex textile is influenced. Many disperse dyes have good fastness to rubbing, washing and light on terylene, but the fastness on spandex can only reach a medium level, so that products with high requirements on the fastness have a great problem in dyeing processing.
The disperse dyes containing heterocyclic rings are a direction of more researches in the field in recent years, because the dyes have better dark color effect and higher molar extinction coefficient, Kelaien develops a group of disperse dyes (ZL200880013404.7) taking benzyl substituted pyridone as a coupling component in 2008, the dyes are mainly used for optical recording data, are used for dyeing textile materials with poor dyeing effect and are difficult to color, the applicant finds that the dyes can be used for dyeing textile materials after being improved, and have outstanding performance.
Disclosure of the invention
The invention aims to provide a disperse dark blue-black dye composition and a dye product thereof, which have comprehensive excellent color fastness performance when being applied to dyeing or printing of hydrophobic fibers, particularly polyester and blend fiber materials thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a disperse dark blue to black dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one compound shown in a formula (I), the component B is selected from at least one compound shown in a formula (II), the component C is selected from at least one compound shown in a formula (III), and based on the total weight of the component A, the component B and the component C, the mass percent of the component A is 30-90%, the mass percent of the component B is 1-50%, and the mass percent of the component C is 1-50%:
in formula (I):
X1is NO2Or CN, X2Is Cl, Br or CN;
R1、R2each independently is C1～C4An alkyl group;
R3、R4each independently is C1～C4Alkyl, -CH2COOK1or-C2H4COOK2In which K is1、K2Each independently is C1～C4An alkyl group.
In formula (II):
X3is Cl, Br, NO2Or CN, X4H, Cl or Br;
R5is C1～C4Alkyl radical, C1～C4Alkoxyalkyl or benzyl.
In the formula (III):
X5is H, NO2CN or-OCH3，X6Is H, NO2、-OCH3Cl or Br;
R6is benzyl or phenethyl.
In the above formulae (I) to (III), said C1～C4The alkyl group can be methyl, ethyl, linear or branched propyl, linear or branched butyl; said C1～C4The alkoxyalkyl group can be methoxyethyl, methoxypropyl, ethoxyethyl, ethoxypropyl, and the like.
In the disperse dark blue to black dye composition of the present invention, component A is preferably at least one selected from the following formulas (I-1) to (I-10):
the component B is preferably at least one selected from the following formulas (II-1) to (II-10):
the component C is preferably at least one selected from the following formulas (III-1) to (III-10), wherein Ph is a phenyl group:
further preferably, the disperse dark blue to black dye composition comprises component a, component B and component C, wherein:
the component A is at least one of formulas (I-1) to (I-6);
the component B is at least one of formulas (II-1) to (II-6);
the component C is at least one of formulas (III-1) to (III-7).
Based on the total weight of the dye component A, B, C, the mass percentage of the dye component A is 50-90%, the mass percentage of the component B is 5-40%, and the mass percentage of the component C is 1-40%.
Or further preferably, the disperse dark blue to black dye composition consists of a component A, a component B and a component C, wherein the mass percentage of the component A is 35-90%, the mass percentage of the component B is 1-45%, and the mass percentage of the component C is 1-45%.
Furthermore, the disperse dark blue to black dye composition provided by the invention is composed of a component A, a component B and a component C, wherein:
the component A is at least one of formulas (I-1) to (I-6);
the component B is at least one of formulas (II-1) to (II-6);
the component C is at least one of formulas (III-1) to (III-7).
Based on the total weight of the dye component A, B, C, the mass percentage of the dye component A is 50-90%, the mass percentage of the component B is 5-40%, and the mass percentage of the component C is 1-40%.
It should be emphasized that the disperse dye compounds of the present invention, the dyes coupled at the ortho position of pyridone or quinolinone hydroxyl group, generally exist in the form of quinone hydrazone, that is, the dyes of general formulas (ii), (iii) substantially have the quinone hydrazone structures shown in the following formulas (IIa), (iiia), and in consideration of the writing habit of those skilled in the art, the written form of azo is still adopted in the summary and the examples of the invention, which does not affect the essence of the present invention:
wherein R is5、R6、X3、X4、X5、X6The same as defined above for the compounds of the formulae (II) and (III).
The disperse dark blue to black dye composition of the invention usually needs to be added with conventional auxiliary agents in the commercial process. Therefore, the invention also provides a disperse dye product which contains the disperse dark blue-black dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dark blue-black dye composition is (0.2-5): 1, and preferably (0.5-2): 1. Preferably, the disperse dye product consists of the disperse dark blue to black dye composition and an auxiliary agent. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in the process of compounding disperse dyes, and is particularly preferably selected from one or a mixture of more than two of the following components: lignosulfonate (e.g., commercially available dispersant Reax 83A, Reax 8A), methyl naphthalenesulfonic acid formaldehyde condensate (dispersant MF), naphthalenesulfonic acid formaldehyde condensate (dispersant NNO), benzylnaphthalenesulfonic acid formaldehyde condensate (dispersant CNF), anhydrous sodium sulfate, polycarboxylic acid polymer dispersant, and the like.
The disperse dye product can be obtained by the following method: mixing A, B, C monomer compound (crude dye) at a certain ratio, and micronizing with a grinder such as a sand mill or a grinder in the presence of adjuvant and water; alternatively, the monomeric dye compounds of component A, B, C 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 disperse dye preparations according to the invention, which are liquid after grinding with a sand mill or a grinding mill and can be in the form of powder or granules after spray drying, are known to the person skilled in the art and, since 100% removal of water is not possible during spray drying, even in the case of pulverulent or granular dye preparations, a certain amount of water is still permitted, preferably not more than 10% of the total weight of the dye preparation.
In addition, when the dye product is applied to printing and dyeing of textile fibers, the technical characteristics which contribute to the improvement of the dyeing effect are the components and the proportion of the dye contained in the product.
The disperse dark blue to black dye composition provided by the invention is also allowed to be further compounded with other dyes to synergically prepare a new blue or black dye composition. The dye compounds of the formula (I), (II) and (III) according to the invention can be conveniently synthesized in a manner known to the person skilled in the art, and commercially available products can also be used.
The invention provides an application of the disperse dark blue-black dye composition and a dye product in dyeing of hydrophobic fiber materials. The dye prepared by the dye composition can dye hydrophobic fiber materials (such as polyester and blended fabrics thereof) in a conventional mode in the industry, such as dyeing by a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be used for direct printing. Wherein, the common dip-dyeing method comprises the steps of pretreating the hydrophobic fiber material, putting the hydrophobic fiber material into a dye vat for dip-dyeing, washing the hydrophobic fiber material to be neutral by cold water after dyeing, wringing, reducing, washing and drying; the direct printing is to carry out dyeing pretreatment, drying and setting on the fabric, print disperse dye color paste on a printing machine, then carry out steaming, fix the color of the dye on the fabric by using a steaming mode, finally wash and tenter setting.
The disperse dark blue to black dye composition and the dye product provided by the invention have the characteristics of excellent fastness to rubbing, washing and sublimation when being applied to dyeing of hydrophobic fiber materials.
(IV) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1
50 g of dye compound shown in formula (I-1), 25 g of dye compound shown in formula (I-2), 20 g of dye compound shown in formula (II-1), 5 g of dye compound shown in formula (III-2) and 150 g of dispersing agent MF, 500 g of water are mixed and blended, and then the mixture is ground, dispersed and spray-dried to obtain the finished product, wherein the finished product can provide navy color tone of polyester and blended fabrics thereof.
Example 2
45 g of dye compound of formula (I-1), 25 g of dye compound of formula (II-1), 30 g of dye compound of formula (III-1), 165 g of dispersing agent MF, 600 g of water are mixed, ground, dispersed and spray-dried to obtain the finished product, and the finished product can provide black tone for polyester and blended fabric thereof.
Example 3
45 g of dye compound of formula (I-1), 20 g of dye compound of formula (II-1), 10 g of dye compound of formula (III-3) and 25 g of dye compound of formula (III-4), 150 g of dispersing agent MF, 30 g of dispersing agent NNO, 650 g of water are mixed, ground, dispersed and spray-dried to obtain the finished product, and the finished product can provide black tone for polyester and blended fabric thereof.
Examples 4 to 40
According to the method described in the example 3, except that the structures and the weights of the component A, the component B and the component C in the table 1 are adopted, 165 g of the auxiliary agent (150 g of the dispersing agent MF and 15 g of the sodium lignosulfonate) is added, 650 g of water is added to be mixed to prepare slurry, and the slurry is ground, dispersed and dried to prepare the finished product, wherein the dye can provide deep color tone with excellent fastness performance for polyester and blended fabrics thereof.
TABLE 1
EXAMPLE 41
50 g of dye compound shown in formula (I-1), 25 g of dye compound shown in formula (II-1), 20 g of dye compound shown in formula (III-1), 5 g of dye compound shown in formula (IV) and 150 g of dispersant CNF are mixed with water, ground and dispersed by a grinding machine and dried to obtain the finished dye, and the dye can provide uniform black with good fastness performance for polyester and blended fabrics thereof.
Example 42
50 g of a compound of a formula (I-1), 10 g of a compound of a formula (II-2), 20 g of a dye compound of a formula (III-4), 5 g of C.I. disperse orange 288, 15 g of a dye compound shown in a formula (V) below and 150 g of a dispersant CNF are mixed and spliced by adding water, and then ground, dispersed and dried by a grinding machine to obtain the finished dye, wherein the dye can provide uniform black with good fastness for polyester and blended fabrics thereof.
Dyeing examples
Respectively weighing 2 g of the disperse dyes prepared in the embodiments 1-42, treating the polyester/ammonia mixed fabric by adopting a conventional high-temperature high-pressure dyeing method, controlling the dyeing depth (o.w.f) to be 6.0% in the treatment process, regulating the pH value of a dyeing bath to be 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 carrying out heat setting at 180 ℃ for 30 seconds according to the conventional method to obtain the dyed fabric. The color fastness to rubbing, washing and sublimation is respectively tested by adopting international standards ISO 105-X12 and AATCC 61-2A, ISO 105-P01, and the color fastness to rubbing, washing and sublimation is specifically shown in the table 2:
TABLE 2
Therefore, the disperse dark blue-black dye disclosed by the invention is excellent in color fastness, is particularly suitable for dyeing polyester and blended fabrics thereof, and can be popularized and applied in a large scale.
Claims (10)
1. A disperse dark blue to black dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one compound shown in a formula (I), the component B is selected from at least one compound shown in a formula (II), the component C is selected from at least one compound shown in a formula (III), and based on the total weight of the component A, the component B and the component C, the mass percent of the component A is 30-90%, the mass percent of the component B is 1-50%, and the mass percent of the component C is 1-50%:
in formula (I):
X1is NO2Or CN, X2Is Cl, Br or CN;
R1、R2each independently is C1～C4An alkyl group;
R3、R4each independently is C1～C4Alkyl, -CH2COOK1or-C2H4COOK2In which K is1、K2Each independently is C1～C4An alkyl group;
in formula (II):
X3is Cl, Br, NO2Or CN, X4H, Cl or Br;
R5is C1～C4Alkyl radical, C1～C4Alkoxyalkyl or benzyl;
in the formula (III):
X5is H, NO2CN or-OCH3，X6Is H, NO2、-OCH3Cl or Br;
R6is benzyl or phenethyl.
2. The disperse dark blue-to-black dye set according to claim 1Compound C of1～C4The alkyl group can be methyl, ethyl, linear or branched propyl, linear or branched butyl; said C1～C4The alkoxyalkyl group may be methoxyethyl, methoxypropyl, ethoxyethyl, ethoxypropyl.
3. A disperse dark blue to black dye composition according to claim 1, wherein: the component A is selected from at least one of the following formulas,
4. a disperse dark blue to black dye composition according to claim 1, wherein: the component B is selected from at least one of the following formulas:
5. a disperse dark blue to black dye composition according to claim 1, said component C being selected from at least one of the following formulae, wherein Ph is phenyl:
6. the disperse dark blue to black dye composition according to claim 1, comprising component a, component B and component C, wherein:
the component A is at least one of formulas (I-1) to (I-6);
the component B is at least one of formulas (II-1) to (II-6);
the component C is at least one of formulas (III-1) to (III-7).
7. The disperse dark blue to black dye composition according to claim 1, which is composed of component a, component B, and component C, wherein:
the component A is at least one of formulas (I-1) to (I-7);
the component B is at least one of formulas (II-1) to (II-6);
the component C is at least one of formulas (III-1) to (III-7);
based on the total weight of the dye component A, B, C, the mass percentage of the component A is 50-90%, the mass percentage of the component B is 5-40%, and the mass percentage of the component C is 1-40%.
8. A disperse dye product comprises the disperse dark blue-black dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dark blue-black dye composition is 0.2-5: 1.
9. A disperse dye preparation according to claim 8, wherein the auxiliaries are one or a combination of any of the following: naphthalene sulfonic acid formaldehyde condensate, methyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonate formaldehyde condensate, anhydrous sodium sulphate and polycarboxylic acid polymer dispersant.
10. Use of the disperse dye preparation according to claim 9 for dyeing polyester and polyester blend fabrics.
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| CN1322227A (en) * | 1999-07-29 | 2001-11-14 | 三井化学株式会社 | Yellow compound and water-based ink-jet recording ink containing compound |
| CN106479221A (en) * | 2015-08-24 | 2017-03-08 | 杭州福莱蒽特精细化工有限公司 | A kind of dark blue to black disperse dye mixture |
| WO2019068443A1 (en) * | 2017-10-02 | 2019-04-11 | Dystar Colours Distribution Gmbh | High wet fast disperse dye mixtures |
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| JP2612294B2 (en) * | 1988-03-11 | 1997-05-21 | 三井東圧化学株式会社 | Yellow color toner composition |
| CN107815141B (en) * | 2017-09-30 | 2021-10-08 | 浙江龙盛集团股份有限公司 | Disperse blue-to-black dye composition and dye product |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1322227A (en) * | 1999-07-29 | 2001-11-14 | 三井化学株式会社 | Yellow compound and water-based ink-jet recording ink containing compound |
| CN106479221A (en) * | 2015-08-24 | 2017-03-08 | 杭州福莱蒽特精细化工有限公司 | A kind of dark blue to black disperse dye mixture |
| WO2019068443A1 (en) * | 2017-10-02 | 2019-04-11 | Dystar Colours Distribution Gmbh | High wet fast disperse dye mixtures |
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