CN110835473A - Disperse dye composition, dye product and application thereof - Google Patents

Disperse dye composition, dye product and application thereof Download PDF

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Publication number
CN110835473A
CN110835473A CN201911164453.7A CN201911164453A CN110835473A CN 110835473 A CN110835473 A CN 110835473A CN 201911164453 A CN201911164453 A CN 201911164453A CN 110835473 A CN110835473 A CN 110835473A
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component
disperse dye
dye composition
formula
dye
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CN110835473B (en
Inventor
朱敬鑫
陈东
杨日升
陈佳蕾
陈晓晓
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SHANGHAI HONGYUAN XINCHUANG MATERIAL TECHNOLOGY Co.,Ltd.
SHAOXING SHANGYU JINGUAN CHEMICAL CO.,LTD.
ZHEJIANG LONGSHENG CHEMICAL RESEARCH Co.,Ltd.
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Shangyu Shaoxing Golden Crown Chemical Co Ltd
ZHEJIANG LONGSHENG CHEMICALS CO Ltd
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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
    • C09B67/008—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
    • 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
    • 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
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)

Abstract

The invention discloses a 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 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) and/or (IV). When the disperse dye composition is applied to printing and dyeing of polyester and polyester blended fiber materials, the disperse dye composition has the characteristics of sublimation resistance, friction resistance, excellent color fastness to washing and the like.

Description

Disperse dye composition, dye product and application thereof
(I) technical field
The invention relates to a disperse dye composition, a dye product thereof and application of the dye product to hydrophobic fiber materials, in particular to application of polyester and blended fabrics thereof in dyeing or printing.
(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.
Unexpectedly, the heterocyclic disperse dye prepared from tetrahydroquinoline and derivatives thereof has good compatibility and cooperativity with the existing disperse blue, disperse yellow and disperse orange dyes, obvious compounding effect, high color development strength and good practicability, comprehensively improves the comprehensive fastness performance of the dye, and has wide development prospect.
Disclosure of the invention
The invention aims to provide a disperse dye composition and a dye product thereof, which have overall 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 dye composition comprises a component A and a component B, 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), based on the component A and the component B, the mass percent of the component A is 5-95%, the mass percent of the component B is 5-95%,
Figure BDA0002288369380000011
Figure BDA0002288369380000021
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 NO2Or CN, X4Is H, Cl, Br or CN;
R5is C1～C4Alkyl radical, C1～C4Alkoxyalkyl or benzyl.
In the above formulas (I) and (II), C1～C4The alkyl group may be methyl, ethyl, linear or branched propyl, linear or branched butyl, preferably methyl or ethyl. Said C1～C4The alkoxyalkyl group may be methoxyethyl, methoxypropyl, ethoxyethyl, ethoxypropyl.
In the disperse dye composition of the present invention, component A is preferably at least one selected from the following formulas (I-1) to (I-10):
Figure BDA0002288369380000022
Figure BDA0002288369380000031
Figure BDA0002288369380000041
the component B is preferably at least one selected from the following formulas (II-1) to (II-10):
Figure BDA0002288369380000042
Figure BDA0002288369380000051
preferably, the disperse dye composition comprises a component A and a component B, 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), based on the component A and the component B, the mass percentage of the component A is 5-95%, and the mass percentage of the component B is 5-95%.
Further preferably, the disperse dye composition consists of a component A and a component B, wherein the mass percentage of the component A is 5-95%, and the mass percentage of the component B is 5-95%.
The disperse dye composition can further comprise a component C of the following formula (III) and/or (IV), wherein based on 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 5-50%, and the mass percent of the component C is 1-50%:
Figure BDA0002288369380000061
in the formula (III):
X5is NO2Or H, X6Is Cl, H, C1～C4Alkoxy or-OCH of2-Ph, Ph being phenyl;
R6is C1～C4Preferably methyl or ethyl.
In the formula (IV):
X7is NO2Or CN;
R7is C1～C4Alkyl radical, R8、R9Each independently is C1～C4Alkyl, -CH2COOK3or-C2H4COOK4Wherein, K is3、K4Each independently is C1～C4An alkyl group.
In the above formulas (III) and (IV), C is1～C4The alkyl group may be methyl, ethyl, linear or branched propyl, or linear or branched butyl. Said C1～C4Alkoxy can be methoxy, ethoxy, linear or branched propoxy, linear or branched butoxy.
The component C is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
Figure BDA0002288369380000071
Figure BDA0002288369380000081
preferably, in the disperse dye composition, 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%.
Further, the disperse dye composition is composed of a component A, a component B and a component C.
Furthermore, the disperse 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-5);
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:
Figure BDA0002288369380000091
wherein R is5、R6、X3、X4、X5、X6The same as defined above for the compounds of the formulae (II) and (III).
The disperse 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 dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is (0.2-5): 1, preferably (0.5-2): 1. Preferably, the disperse dye product consists of a disperse 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: lignosulfonates (e.g., commercially available dispersants Reax83A, Reax8A), 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-based polymer dispersants, 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 dye composition provided by the invention can be further compounded with other dyes to be synergistic to prepare a novel blue or black dye composition. The dye compounds of the formulae (I), (II), (III) and (IV) according to the invention can be synthesized conveniently in a manner known to the person skilled in the art, and commercially available products can also be used.
The invention provides the application of the disperse dye composition and the dye product in dyeing or printing 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 dye composition and the dye product provided by the invention have the characteristics of excellent friction resistance, washing resistance, sublimation fastness and the like when being applied to dyeing or printing 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 of formula (I-1), 25 g of dye compound of formula (I-2), 20 g of dye compound of formula (II-1), 5 g of dye compound of formula (II-2) and 150 g of dispersing agent MF, and 500 g of water are mixed, ground, dispersed and spray-dried to obtain the finished product, and the finished product can provide navy-blue color tone of polyester and blended fabrics thereof.
Figure BDA0002288369380000111
Example 2
40 g of dye compound shown in formula (I-1), 25 g of dye compound shown in formula (II-1), 35 g of dye compound shown in formula (III-1) and 165 g of dispersing agent MF are mixed with 600 g of water, and then the mixture is ground, dispersed and spray-dried to obtain the finished product, wherein the finished product can provide black tone of polyester and blended fabrics thereof.
Figure BDA0002288369380000112
Figure BDA0002288369380000121
Example 3
45 g of dye compound of formula (I-1), 20 g of dye compound of formula (II-1), 35 g of dye compound of formula (IV-1), 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 of polyester and blended fabric thereof.
Figure BDA0002288369380000122
Examples 4 to 45
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
Figure BDA0002288369380000131
Figure BDA0002288369380000141
Example 46
75 g of dye compound of formula (I-2), 20 g of dye compound of formula (II-1), 5 g of C.I. disperse red 152 dye 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 blue with good fastness for polyester and blended fabrics thereof.
Example 47
50 g of a compound of a formula (I-1), 25 g of a compound of a formula (II-2), 5 g of a C.I. disperse orange 288 dye, 20 g of a C.I. disperse blue 291 dye and 150 g of a dispersant CNF are mixed with water, ground and dispersed by a grinding machine and dried to obtain a finished dye, and the dye can provide a navy blue with good fastness performance to polyester and blended fabrics thereof.
Dyeing examples
Respectively weighing 2 g of the disperse dyes prepared in the embodiments 1-47, 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 cooling to 70 ℃ according to the conventional method, and taking out. Observing the color of the sample cloth, and respectively testing the fastness to rubbing, washing and sublimation by adopting international standards ISO 105-X12 and AATCC 61-2A, ISO 105-P01, wherein the color is shown in Table 2:
TABLE 2
Figure BDA0002288369380000151
Figure BDA0002288369380000161
Therefore, the disperse 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 dye composition comprises a component A and a component B, 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), based on the component A and the component B, the mass percent of the component A is 5-95%, the mass percent of the component B is 5-95%,
Figure FDA0002288369370000011
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 NO2Or CN, X4Is H, Cl, Br or CN;
R5is C1～C4Alkyl radical, C1～C4Alkoxyalkyl or benzyl.
2. A disperse dye composition according to claim 1, wherein: the component A is selected from at least one of the following formulas,
Figure FDA0002288369370000012
Figure FDA0002288369370000021
Figure FDA0002288369370000031
3. a disperse dye composition according to claim 1, wherein: the component B is selected from at least one of the following formulas:
Figure FDA0002288369370000032
Figure FDA0002288369370000041
Figure FDA0002288369370000051
4. the disperse dye composition according to claim 1, further comprising a component C of the following formulae (III) and/or (IV), wherein based on the component A, the component B and the component C, the mass percent of A is 30-90%, the mass percent of the component B is 5-50%, and the mass percent of the component C is 1-50%,
Figure FDA0002288369370000052
in the formula (III):
X5is NO2Or H, X6Is Cl, H, C1～C4Alkoxy or-OCH of2-Ph，Ph is phenyl;
R6is C1～C4Alkyl group of (1).
In the formula (IV):
X7is NO2Or CN;
R7is C1～C4Alkyl radical, R8、R9Each independently is C1～C4Alkyl, -CH2COOK3or-C2H4COOK4Wherein, K is3、K4Each independently is C1～C4An alkyl group.
5. A disperse dye composition according to claim 4, wherein: the component C is selected from at least one of the following formulas:
Figure FDA0002288369370000061
Figure FDA0002288369370000071
6. a disperse dye composition according to claim 4, 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-5).
7. The disperse dye composition according to claim 4, which consists 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-4);
the component C is at least one of formulas (III-1) to (III-5);
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, which comprises the disperse dye composition as claimed in claim 1 or 4 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5: 1.
9. A disperse dye composition according to claim 8 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 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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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104087010A (en) * 2013-05-16 2014-10-08 上海安诺其纺织化工股份有限公司 Disperse dye mixture
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
CN107075268A (en) * 2014-09-15 2017-08-18 德司达染料分销有限公司 High humidity rapid dispersion dyestuff and its mixture
TW201915102A (en) * 2017-10-02 2019-04-16 德商德司達染料分銷有限公司 High wet fast disperse dye mixtures

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104087010A (en) * 2013-05-16 2014-10-08 上海安诺其纺织化工股份有限公司 Disperse dye mixture
CN107075268A (en) * 2014-09-15 2017-08-18 德司达染料分销有限公司 High humidity rapid dispersion dyestuff and its mixture
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
TW201915102A (en) * 2017-10-02 2019-04-16 德商德司達染料分銷有限公司 High wet fast disperse dye mixtures

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