CN112679985B - Blue-to-black disperse dye composition and dye product - Google Patents
Blue-to-black disperse dye composition and dye product Download PDFInfo
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Abstract
The invention discloses a blue-to-black disperse dye composition, which comprises a component A, a component B and a component C, wherein the component A is selected from at least one of compounds shown in a formula (I), the component B is selected from at least one of compounds shown in a formula (II), and the component C is selected from at least one of compounds shown in a formula (III). The blue-to-black disperse dye composition provided by the invention has excellent fastness, especially washing staining fastness, when being applied to dyeing of hydrophobic fiber materials such as polyester and blended fabrics thereof:
Description
field of the art
The invention relates to a blue-to-black dye composition and a dye product, in particular to an environment-friendly blue-to-black disperse dye composition and a dye product which are suitable for dyeing and printing hydrophobic fiber materials.
(II) background art
The maximum amount of blue-black series dye is used in disperse dyes, and the traditional dye composition of blue-black by C.I. disperse blue 291:1, C.I. disperse violet 93 and C.I. disperse orange 76 is classified as forbidden dye by European countries such as Germany because the C.I. disperse orange 76 can be cracked under certain specific conditions to generate aromatic amine harmful to human body, generate allergy to human body. In recent years, many disperse blue-black dye compositions have emerged as alternatives to c.i. disperse orange 76, such as documents CN1230575A, CN101798472a and CN 105111785.
However, it has recently been found that c.i. disperse violet 93 is also ecologically unsafe, and it is an urgent issue to find a novel disperse blue-black series dye which is environmentally friendly and excellent in various color fastness.
(III) summary of the invention
The invention provides a blue-to-black disperse dye composition and a dye product, which have excellent color fastness and are environment-friendly novel blue-black series dye compositions.
The technical scheme adopted by the invention is as follows:
a blue-to-black disperse dye composition comprises a component A, a component B and a component C, wherein the component A is selected from one or more of compounds shown in a formula (I), the component B is selected from one or more of compounds shown in a formula (II), the component C is selected from one or more of compounds shown in a formula (III), the mass percent of the component A is 30-85%, the mass percent of the component B is 5-40%, and the mass percent of the component C is 10-60% based on the components A-C:
in formula (I):
X 1 is hydrogen or halogen, R 1 、R 2 Each independently is C 1 ～C 4 Alkyl, R 3 、R 4 Each independently cyanoethyl or allyl.
In formula (II):
R 5 is hydrogen or C 1 ～C 4 Alkoxy, R 5’ Is C 1 ～C 4 Alkyl, R 6 、R 7 Each independently is C 1 ～C 4 Alkyl, benzyl, -CH 2 CH 2 COOCH 3 or-CH 2 COOCH 3 。
In formula (III):
R 8 is hydrogen, halogen or C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy, R 9 Is cyanoethyl, C 1 ～C 4 Alkyl, -CH 2 -CH＝CH 2 N is 1 or 2.
In the above formulae (I) to (III), the above formula C 1 ～C 4 The alkyl group may be methyl, ethyl, straight or branched propyl, straight or branched butyl, said C 1 ～C 4 The alkoxy group may be methoxy, ethoxy, straight or branched propoxy, straight or branched butoxy, halogen being preferably Cl or Br.
Preferably, the blue-to-black disperse dye composition is based on the components A to C, wherein the mass percentage of the component A is 30 to 80%, the mass percentage of the component B is 5 to 35%, and the mass percentage of the component C is 10 to 50%.
Preferably, the component A is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
preferably, the component B is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
preferably, the component C is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
as a further preferred aspect, the blue to black disperse dye composition comprises:
the component A is at least one selected from the formulas (I-1) to (I-4);
component B is selected from formula (II-1) and/or formula (II-6);
the component C is selected from at least one of the formulas (III-1) to (III-3).
Based on the components A to C, the mass percentage of the component A is 30 to 85 percent, the mass percentage of the component B is 5 to 40 percent, and the mass percentage of the component C is 10 to 60 percent.
Further, the blue-to-black disperse dye composition consists of a component A, a component B and a component C, wherein the mass percent of the component A is 30-85%, the mass percent of the component B is 5-40% and the mass percent of the component C is 10-60% based on the components A-C.
Still further, the blue to black disperse dye composition of the present invention is composed of a component a, a component B and a component C, wherein:
the component A is at least one selected from the formulas (I-1) to (I-4);
component B is selected from formula (II-1) and/or formula (II-6);
the component C is selected from at least one of the formulas (III-1) to (III-3).
Based on the components A to C, the mass percentage of the component A is 30 to 80 percent, the mass percentage of the component B is 10 to 40 percent, and the mass percentage of the component C is 10 to 60 percent.
The blue to black disperse dye composition of the invention generally requires the addition of conventional auxiliaries during commercialization. The invention therefore also provides a disperse dye preparation comprising the blue-to-black disperse dye composition and an auxiliary agent, the weight ratio of the auxiliary agent to the blue-to-black disperse dye composition being (0.2-5): 1, preferably (0.5-2): 1. Preferably, the disperse dye product consists of a blue-to-black disperse dye composition and an auxiliary agent. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in disperse dye compounding, and is particularly preferably one or a mixture of more than two of the following: lignin sulfonate (such as commercial dispersant Reax 83A, reax a), methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF), naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), benzyl naphthalene sulfonic 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 the component A, B, C monomer compound (raw dye) according to a proportion, and then carrying out micropellet formation by using a grinder such as a sand grinder or a grinding machine in the presence of an auxiliary agent and water; alternatively, the dye monomer compound of component A, B, C may be subjected to a micropellet treatment with a pulverizer such as a sand mill or a grinding machine in the presence of an auxiliary agent and water, respectively, and then mixed in a ratio. The disperse dye preparation according to the invention is liquid after grinding by a sand mill or a grinding machine and can be in powder or granule form after spray drying, which is a preparation method known to the person skilled in the art, since 100% removal of moisture is not possible during spray drying, a certain amount of moisture is allowed to be present even in the powder or granule form of the dye preparation, preferably not more than 10% of the total weight of the dye preparation.
In addition, when the dye product is applied to dyeing of textile fibers, the technical feature contributing to the improvement of dyeing effect is the dye component and the proportion contained in the product.
The blue-to-black disperse dye composition provided by the invention also allows the blue-to-black disperse dye composition to be compounded with other dyes to be synergistic to prepare new blue or black dyes. The dye compounds of the formulae (I), (II), (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 the use of the blue to black disperse dye composition and dye article in dyeing hydrophobic fiber materials. The dye prepared by the dye composition can be used for dyeing hydrophobic fiber materials (such as polyester and blended fabrics thereof) in a manner conventional in industry, such as 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 pretreated hydrophobic fiber material into a dye vat for dip dyeing, washing the dyed hydrophobic fiber material to be neutral by cold water, wringing the hydrophobic fiber material, carrying out reduction washing and drying the hydrophobic fiber material; and (3) directly printing, namely, carrying out dyeing pretreatment on the fabric, drying, setting, printing disperse dye color paste on a printing machine, steaming, fixing the dye on the fabric by utilizing a steaming mode, washing with water, and tentering and setting.
The blue-to-black disperse dye composition and the dye product provided by the invention have the characteristics of excellent color fastness, especially excellent washing color fastness, environmental protection, safety and the like when being applied to dyeing of hydrophobic fiber materials, and the ecological environment-friendly performance meets the requirements of Oeko-tex 100 on textiles.
4. Detailed description of the preferred embodiments
The invention will be further described with reference to the following specific examples, but the scope of the invention is not limited thereto:
example 1
55 g of dye compound of formula (I-7), 30 g of dye compound of formula (II-1), 15 g of dye compound of formula (III-1) and 200 g of dispersing agent MF are mixed together by adding 1450 g of water, and then the mixture is ground, dispersed and spray-dried, so that a finished product is obtained, and the finished product can provide blue color tone for polyester and blended fabrics thereof.
Example 2
35 g of dye compound of formula (I-1), 20 g of dye compound of formula (II-2), 45 g of dye compound of formula (III-1) and 200 g of dispersing agent MF are mixed together by adding 1800 g of water, and then are ground, dispersed and spray-dried, so that a finished product is obtained, and the finished product can provide black color tone for polyester and blended fabrics thereof.
Example 3
35 g of dye compound of formula (I-7), 35 g of dye compound of formula (II-2), 20 g of dye compound of formula (III-3), 150 g of dispersing agent NNO and 50 g of sodium lignin sulfonate are mixed together by adding 2000 g of water, and then the mixture is ground, dispersed and spray-dried, so that a finished product is obtained, and the finished product can provide deep blue color tone for polyester and blended fabrics thereof.
Examples 4 to 28
The method of examples 1-3 was followed except that 165 g of an auxiliary agent (150 g of dispersant MF, 15 g of sodium lignin sulfonate) was added to the structure and weight of component A, component B and component C in Table 1, and 2500 g of water was added to the mixture to prepare a slurry, which was then ground, dispersed and dried to obtain a finished product, which was able to give a blue-black hue excellent in various fastness properties to polyester and its blend fabrics.
TABLE 1
Example 29
40 g of a compound of formula (I-1), 25 g of a compound of formula (II-1), 30 g of a dye compound of formula (III-3), 5 g of C.I. dispersing orange 73, 150 g of dispersing agent CNF and 30 g of sodium lignin sulfonate are mixed together by adding water, and then are ground and dispersed by a grinder and dried to obtain a finished dye which can provide black with uniform polyester and blended fabric thereof and good fastness.
Comparative example 1
The dye composition closest to example 1 of patent CN101798472a was taken as comparative example 1 as follows:
comparative example 2
As comparative example 2, comparative example 9, which is more similar to that of patent CN101798472a, has the following dye composition:
dyeing examples
2 g of the disperse dye prepared in examples 1-29 and the disperse dye prepared in comparative examples 1-2 are respectively weighed, polyester/spandex mixed fabrics are treated by a conventional high-temperature high-pressure dyeing method and heat setting, in the treatment process, the dyeing depth (o.w.f) is controlled to be 6.0%, the bath ratio is 1:25, the pH value of a dyeing bath is regulated to be 4-5, the dyeing is carried out at room temperature, the temperature is increased to 125 ℃ at 1 ℃/min, the temperature is kept for 45min, the reduction cleaning, the washing and the drying are carried out according to the conventional method, and the heat setting is carried out at 180 ℃ for 30 seconds, so that blue to black dyed fabrics are obtained. The fastness to rubbing, washing and sublimation was measured according to ISO 105-X12, AATCC 61-2A, ISO 105X 11P 01, respectively, and the results are given in Table 2 below:
TABLE 2
In conclusion, the blue-to-black disperse dye composition provided by the invention has excellent color fastness when applied to dyeing of terylene and blended fabrics thereof, and is an environment-friendly novel blue-black series dye composition.
Claims (10)
1. A blue-to-black disperse dye composition comprises a component A, a component B and a component C, wherein the component A is selected from one or more of compounds shown in a formula (I), the component B is selected from one or more of compounds shown in a formula (II), the component C is selected from one or more of compounds shown in a formula (III), the mass percent of the component A is 30-85%, the mass percent of the component B is 5-40%, and the mass percent of the component C is 10-60% based on the components A-C:
in formula (I):
X 1 is hydrogen or halogen, R 1 、R 2 Each independently is C 1 ～C 4 Alkyl, R 3 、R 4 Each independently cyanoethyl or allyl;
in formula (II):
R 5 is hydrogen or C 1 ～C 4 Alkoxy, R 5’ Is C 1 ～C 4 Alkyl, R 6 、R 7 Each independently is C 1 ～C 4 Alkyl, benzyl, -CH 2 CH 2 COOCH 3 or-CH 2 COOCH 3 ；
In formula (III):
R 8 is hydrogen, halogen or C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy, R 9 Is cyanoethyl, C 1 ～C 4 Alkyl, -CH 2 -CH＝CH 2 N is 1 or 2.
2. A blue to black disperse dye composition according to claim 1, wherein R 1 、R 2 Each independently is methyl or ethyl, R 5 Is H or methoxy, said R 5’ Is methyl or ethyl, said R 6 、R 7 Each independently is C 1 ～C 4 Alkyl or benzyl.
3. A blue to black disperse dye composition according to claim 1, wherein component a is selected from one or a mixture of two or more of the following formulas in any proportion:
4. a blue to black disperse dye composition according to claim 1, wherein component B is selected from one of the following formulas or a mixture of two or more of them in any proportion:
5. a blue to black disperse dye composition according to claim 1, wherein component C is selected from one or a mixture of two or more of the following formulas in any proportion:
6. the blue-to-black disperse dye composition according to claim 1, which comprises a component A, a component B and a component C, wherein the mass percentage of the component A is 30-85%, the mass percentage of the component B is 5-40% and the mass percentage of the component C is 10-60% based on the total weight of the components A-C.
7. A blue to black disperse dye composition according to claim 3, wherein component a is selected from at least one of formulae (I-1) to (I-4).
8. A blue to black disperse dye composition according to claim 4, wherein component B is selected from the group consisting of formula (II-1) and/or formula (II-6).
9. A blue to black disperse dye composition according to claim 5, wherein component C is selected from at least one of formulae (III-1) to (III-3).
10. A disperse dye preparation comprising a blue to black disperse dye composition according to any one of claims 1 to 9 and an auxiliary agent in a weight ratio of 0.2 to 5:1, wherein the auxiliary agent is 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 sulfate and polycarboxylic acid polymer dispersant.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2516302A (en) * | 1945-11-28 | 1950-07-25 | Eastman Kodak Co | Fluorine-containing azo compounds |
| ES452451A1 (en) * | 1975-10-17 | 1977-11-01 | Bayer Ag | Monoazo dyes derived from 2-substituted-4-nitro-1-naphthylamines |
| FR2379833A1 (en) * | 1977-02-07 | 1978-09-01 | Eastman Kodak Co | THERMODEVELOPABLE PHOTOGRAPHIC PRODUCT |
| CN111117289A (en) * | 2019-11-29 | 2020-05-08 | 浙江龙盛染料化工有限公司 | Blue-to-black disperse dye composition and dye product |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2516302A (en) * | 1945-11-28 | 1950-07-25 | Eastman Kodak Co | Fluorine-containing azo compounds |
| ES452451A1 (en) * | 1975-10-17 | 1977-11-01 | Bayer Ag | Monoazo dyes derived from 2-substituted-4-nitro-1-naphthylamines |
| FR2379833A1 (en) * | 1977-02-07 | 1978-09-01 | Eastman Kodak Co | THERMODEVELOPABLE PHOTOGRAPHIC PRODUCT |
| CN111117289A (en) * | 2019-11-29 | 2020-05-08 | 浙江龙盛染料化工有限公司 | Blue-to-black disperse dye composition and dye product |
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