CN114773877B - Disperse blue dye composition and product thereof - Google Patents

Disperse blue dye composition and product thereof Download PDF

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Publication number
CN114773877B
CN114773877B CN202210548106.XA CN202210548106A CN114773877B CN 114773877 B CN114773877 B CN 114773877B CN 202210548106 A CN202210548106 A CN 202210548106A CN 114773877 B CN114773877 B CN 114773877B
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component
blue dye
dye composition
disperse blue
alkyl
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CN114773877A (en
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朱鹏飞
何峰
陈立锋
朱炜
李海锋
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Shanghai Hongyuan Xinchuang Material Technology Co ltd
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Shanghai Hongyuan Xinchuang Material Technology Co ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046Mixtures of two or more azo dyes
    • C09B67/0051Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C09B67/0052Mixtures of two or more reactive monoazo dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008Preparations of disperse dyes or solvent dyes

Abstract

The invention provides an environment-friendly disperse blue 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 the following formulas (I), the component B is selected from at least one of the following formulas (II), and the component C is selected from at least one of the following formulas (III); further, the dye also comprises a component D, wherein the component D is at least one selected from compounds shown in the formula (IV) and/or the formula (V), and the dye and the product thereof have the characteristics of good lifting property, leveling property, compatibility, excellent washing fastness, friction fastness, perspiration fastness and the like when being applied to dyeing of hydrophobic fiber materials.

Description

Disperse blue dye composition and product thereof
Field of the art
The invention relates to a disperse blue dye composition, in particular to an environment-friendly disperse blue dye composition suitable for dyeing and printing hydrophobic fiber materials and a product thereof.
(II) background art
Along with the continuous improvement of living standard, the requirements of people on the quality of textiles are higher, correspondingly, the color fastness of dyed dyes is also higher, and the environment-friendly blue disperse dyes with excellent color fastness are not more in the market.
(III) summary of the invention
In order to solve the problems, the invention provides an environment-friendly disperse blue dye composition which has the characteristics of good lifting property, leveling property, reproducibility, washing fastness, friction resistance, perspiration fastness and the like when being applied to dyeing of hydrophobic fiber materials.
The technical scheme adopted by the invention is as follows:
a disperse blue dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), the component C is selected from at least one of the following formulas (III), the mass percent of the component A is 10-85%, the mass percent of the component B is 10-85%, and the mass percent of the component C is 1-50% based on the components A, B and C:
in formula (I):
R 1 is hydrogen or-NHCOK 1 Wherein K is 1 Is C 1 ~C 4 An alkyl group;
R 2 、R 3 each independently is C 1 ~C 4 Alkyl being optionally-OK 2 、-OCOK 3 、-COOK 4 Substituted C 1 ~C 4 Alkyl, where K 2 ~K 4 Each independently is C 1 ~C 4 An alkyl group;
in formula (II):
R 4 is hydrogen, C 1 ~C 4 Alkyl or-NHCOK 5 Wherein K is 5 Is C 1 ~C 4 An alkyl group;
R 5 、R 6 each independently is C 1 ~C 4 Alkyl being substituted by cyano, -OK 6 、-OCOK 7 、-COOK 8 Substituted C 1 ~C 4 Alkyl, where K 6 ~K 8 Each independently is C 1 ~C 4 An alkyl group;
in formula (III):
R 7 is C 1 ~C 4 Alkyl or-NHCOK 9 Wherein K is 9 Is C 1 ~C 4 An alkyl group;
R 8 、R 9 each independently ofStanding as C 1 ~C 4 Alkyl being optionally substituted by cyano, -CH=CH 2 、-OK 10 、-OCOK 11 、-COOK 12 Substituted C 1 ~C 4 Alkyl, where K 10 ~K 12 Each independently is C 1 ~C 4 An alkyl group.
In the invention, the C 1 ~C 4 The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.
Further, R 1 Preferably hydrogen or-NHCOCH 3
Further, R 2 、R 3 Each independently is preferably ethyl, -C 2 H 4 COOCH 3 、-C 2 H 4 OCOCH 3 or-C 2 H 4 O CH 3
Further, R 4 Preferably hydrogen, methyl or-NHCOCH 3
Further, R 5 、R 6 Each independently is preferably ethyl, -C 2 H 4 CN、-C 2 H 4 COOCH 3 、-C 2 H 4 OCOCH 3 or-C 2 H 4 OCH 3
Further, R 7 Preferably methyl or-NHCOCH 3
Further, R 8 、R 9 Each independently is preferably ethyl, -C 2 H 4 CN、-C 2 H 4 COOCH 3 、-C 2 H 4 OCOCH 3 、-C 2 H 4 OCH 3 or-CH 2 CH=CH 2
As another embodiment, the blue disperse dye composition according to the present invention may further comprise a component D selected from at least one of the compounds represented by formula (iv) and/or formula (v), wherein the mass of the component D is greater than 0 and not more than 50% of the total mass of the components a, B and C:
in formula (IV):
R 10 is halogen or-Ph-K 13 Wherein Ph is phenyl, K 13 Is hydroxy or C 1 ~C 4 Alkoxy, R 10 Preferably Br, -Ph-OH or-Ph-OCH 3
In formula (V):
R 11 is C 1 ~C 4 Alkyl, preferably methyl or ethyl.
R 12 、R 13 Each independently is C 1 ~C 4 Alkyl being substituted by hydroxy, cyano, -OCOK 14 、-COOK 15 Substituted C 1 ~C 4 Alkyl, where K 14 、K 15 Each independently is C 1 ~C 4 Alkyl, R 12 、R 13 Each independently is preferably ethyl, -C 2 H 4 OH、-C 2 H 4 CN、-C 2 H 4 OCOCH 3 or-C 2 H 4 COOCH 3
Further, the component A is preferably selected from one of the following formulas or a mixture of two or more of them in any proportion:
further, the component B is preferably selected from one of the following formulas or a mixture of two or more of them in any proportion:
further, the component C is preferably selected from one of the following formulas or a mixture of two or more of them in any proportion:
further, the component D is preferably selected from one of the following formulas or a mixture of two or more of them in any proportion:
preferably, the blue disperse dye composition comprises 20-75% of a component A, 20-75% of a component B and 5-40% of a component C.
Preferably, the blue disperse dye composition comprises 20-75% of a component A, 20-75% of a component B, 5-40% of a component C and not more than 40% of the total mass of the components A-C, wherein the mass of the component D is greater than 0.
As a further preferred aspect, the blue disperse dye composition comprises a component a, a component B and a component C, wherein the mass percentage of the component a is 20-75%, the mass percentage of the component B is 20-75%, and the mass percentage of the component C is 5-40%.
As a further preferred aspect, the blue disperse dye composition comprises a component a, a component B, a component C and a component D, wherein the component a accounts for 20-75% by mass, the component B accounts for 20-75% by mass, the component C accounts for 5-40% by mass, and the component D accounts for more than 0 and not more than 40% by mass of the total mass of the components a-C.
A particularly preferred embodiment 1 of the present invention is: the blue disperse dye composition comprises a component A, a component B and a component C, wherein:
component A is selected from at least one of the formulae (I-1) to (I-3),
the component B is at least one selected from the formulas (II-1) to (II-4),
the component C is at least one selected from the formulas (III-1) to (III-3),
in the composition, the mass percentage of the component A is 20-75%, the mass percentage of the component B is 20-75%, and the mass percentage of the component C is 5-40%.
A particularly preferred embodiment 2 of the present invention is: the blue-to-black disperse dye composition comprises a component A, a component B, a component C and a component D, wherein:
component A is selected from at least one of the formulae (I-1) to (I-3),
the component B is at least one selected from the formulas (II-1) to (II-4),
the component C is at least one selected from the formulas (III-1) to (III-3),
the component D is at least one selected from the formulas (IV-1) to (IV-3) and (V-1) to (V-4),
in the composition, the mass percentage of the component A is 20-75%, the mass percentage of the component B is 20-75%, the mass percentage of the component C is 5-40%, and the mass percentage of the component D is more than 0 and not more than 40% of the total mass of the components A-C.
The disperse blue dye composition can be directly sold as a commodity or can be sold as a commodity after adding a conventional auxiliary agent or applied to coloring textile materials. Therefore, the invention also provides a disperse blue dye product which mainly comprises the disperse blue dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse blue dye composition is 0.2-5:1. Preferably, the disperse blue dye product consists of the disperse blue 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 preferably one or a mixture of more than two of the following components in any proportion: naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate [ such as methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF) ], naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), benzyl naphthalene sulfonic acid formaldehyde condensate (dispersant CNF), sodium lignin sulfonate (lignin 85A, lignin 83A), sodium sulfate (sodium sulfate), and the like.
The preparation method of the disperse blue dye product provided by the invention comprises the following steps: mixing dye monomer compounds (raw dyes) forming a disperse blue dye composition according to a proportion, and then carrying out micropellet formation by using a grinder such as a sand grinder or a grinder in the presence of an auxiliary agent, water or other wetting agents; alternatively, the dye monomer compounds may be subjected to a fine particle formation treatment by 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 proportion. The disperse blue dye product is liquid after grinding by a sand mill or a grinding machine, and can be powder or granule after spray drying, which is a preparation method known to a person skilled in the art.
In the present invention, the dye compounds represented by the formulae (I) to (V) can be conveniently synthesized in a manner well known to those skilled in the art, and commercially available products can also be used.
The dye product prepared by the dye composition can be used for dyeing hydrophobic fiber materials (such as polyester and blended fabrics thereof) in a conventional manner in industry, such as dyeing by a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be directly used for printing. Among them, common dip dyeing methods are as follows: pretreating a hydrophobic fiber material, putting the pretreated hydrophobic fiber material into a dye vat for dip dyeing, washing the dye vat with cold water until the dye vat is neutral, wringing the dye vat to dryness, and then carrying out reduction washing and drying; direct printing such as: and (3) carrying out dyeing pretreatment on the fabric, drying, shaping, printing disperse dye color paste on a printing machine, steaming, fixing the color of the dye on the fabric by utilizing a steaming mode, washing with water, and tentering and shaping.
The disperse blue dye composition and the dye product provided by the invention have the characteristics of good lifting property, leveling property, reproducibility, washing fastness, friction resistance, perspiration fastness and the like when being applied to dyeing of hydrophobic fiber materials, and meet the requirements of Oeko-Tex standard 100 after dyeing.
(IV) detailed description of the invention
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:
50 g of component A of the compound of the formula (I-1), 40 g of component B of the compound of the formula (II-1), 10 g of component C of the compound of the formula (III-1) and 250 g of dispersing agent MF are added with 650 g of water for blending, and then the mixture is ground, dispersed and dried to obtain a finished product, and the dye can provide blue with excellent fastness properties for fabrics.
Example 2:
50 g of a component A of a compound of a formula (I-1), 30 g of a component B of a compound of a formula (II-1), 5 g of a component C of a compound of a formula (III-1), 3 g of a formula (IV-2), 3 g of a formula (IV-3) and 6 g of a formula (V-1) and 250 g of a dispersing agent MF are mixed together by adding 650 g of water, and then the mixture is ground, dispersed and dried to obtain a finished product, wherein the dye can provide blue with excellent fastness properties for fabrics.
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Examples 3 to 30:
according to the method described in example 1, except that the structures and weights of components A to D in Table 1 are adopted, 250 g of auxiliary agent (200 g of dispersing agent MF and 50 g of sodium lignin sulfonate) is added, 800 g of water is added and mixed to prepare slurry, grinding and dispersing are carried out, and drying are carried out, so that a finished product is obtained, and the dye can provide blue color tone with excellent fastness properties for fabrics:
TABLE 1
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Dyeing examples:
the disperse dyes prepared in examples 1 to 30 were selected and tested for their respective fastness to washing, perspiration and rubbing according to the standards ISO 105-C10, ISO 105-E04, ISO 105-X12, with the results given in Table 3 below:
TABLE 3 Table 3
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In conclusion, the disperse blue dye composition provided by the invention has good washing fastness, perspiration fastness and rubbing fastness, and can meet the printing and dyeing requirements of fabrics with high fastness.

Claims (14)

1. A disperse blue dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), the component C is selected from at least one of the following formulas (III), the mass percent of the component A is 10-85%, the mass percent of the component B is 10-85%, and the mass percent of the component C is 1-50% based on the component A, the component B and the component C:
in the formula (I), R 1 Is hydrogen or-NHCOK 1 Wherein K is 1 Is C 1 ~C 4 An alkyl group; r is R 2 、R 3 Each independently is C 1 ~C 4 Alkyl being optionally-OK 2 、-OCOK 3 、-COOK 4 Substituted C 1 ~C 4 Alkyl, where K 2 ~K 4 Each independently is C 1 ~C 4 An alkyl group;
in the formula (II), R 4 Is hydrogen, C 1 ~C 4 Alkyl or-NHCOK 5 Wherein K is 5 Is C 1 ~C 4 An alkyl group; r is R 5 、R 6 Each independently is C 1 ~C 4 Alkyl being substituted by cyano, -OK 6 、-OCOK 7 、-COOK 8 Substituted C 1 ~C 4 Alkyl, where K 6 ~K 8 Each independently is C 1 ~C 4 An alkyl group;
in the formula (III), R 7 Is C 1 ~C 4 Alkyl or-NHCOK 9 Wherein K is 9 Is C 1 ~C 4 An alkyl group; r is R 8 、R 9 Each independently is C 1 ~C 4 Alkyl being optionally substituted by cyano, -CH=CH 2 、-OK 10 、-OCOK 11 、-COOK 12 Substituted C 1 ~C 4 Alkyl, where K 10 ~K 12 Each independently is C 1 ~C 4 An alkyl group.
2. The disperse blue dye composition according to claim 1, wherein C 1 ~C 4 Alkyl is methyl or ethyl, R 1 Is hydrogen or-NHCOCH 3 ,R 2 、R 3 Each independently isEthyl, -C 2 H 4 COOCH 3 、-C 2 H 4 OCOCH 3 or-C 2 H 4 O CH 3 ,R 4 Is hydrogen, methyl or-NHCOCH 3 ,R 5 、R 6 Each independently is ethyl, -C 2 H 4 CN、-C 2 H 4 COOCH 3 、-C 2 H 4 OCOCH 3 or-C 2 H 4 OCH 3 ,R 7 Is methyl or-NHCOCH 3 ,R 8 、R 9 Each independently is ethyl, -C 2 H 4 CN、-C 2 H 4 COOCH 3 、-C 2 H 4 OCOCH 3 、-C 2 H 4 OCH 3 or-CH 2 CH=CH 2
3. The disperse blue dye composition according to claim 1, further comprising a component D selected from at least one of the compounds of formula (IV) and/or formula (V), wherein the mass of component D is greater than 0 and not more than 50% of the total mass of component A, component B and component C:
in the formula (IV), R 10 Is halogen or-Ph-K 13 Wherein Ph is phenyl, K 13 Is hydroxy or C 1 ~C 4 Alkoxy, R 10 Preferably Br, -Ph-OH or-Ph-OCH 3
In the formula (V), R 11 Is C 1 ~C 4 An alkyl group; r is R 12 、R 13 Each independently is C 1 ~C 4 Alkyl being substituted by hydroxy, cyano, -OCOK 14 、-COOK 15 Substituted C 1 ~C 4 Alkyl, where K 14 、K 15 Each independently is C 1 ~C 4 An alkyl group.
4. A partition as claimed in claim 3Disperse blue dye composition, in formula (V), R 11 Methyl or ethyl; r is R 12 、R 13 Each independently is ethyl, -C 2 H 4 OH、-C 2 H 4 CN、-C 2 H 4 OCOCH 3 or-C 2 H 4 COOCH 3
5. The disperse blue dye composition according to claim 1, wherein component a is selected from one of the following formulas or a mixture of two or more of them in any proportion:
6. the disperse blue 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:
7. the disperse blue dye composition according to claim 1, wherein component C is selected from one of the following formulas or a mixture of two or more of them in any proportion:
8. a disperse blue dye composition according to claim 3, wherein component D is selected from one or a mixture of two or more of the following formulae in any proportion:
9. the disperse blue dye composition according to claim 1, comprising component a, component B and component C, wherein:
component A is selected from at least one of the formulae (I-1) to (I-3),
the component B is at least one selected from the formulas (II-1) to (II-4),
the component C is at least one selected from the formulas (III-1) to (III-3),
in the composition, the mass percentage of the component A is 20-75%, the mass percentage of the component B is 20-75%, and the mass percentage of the component C is 5-40%;
10. the disperse blue dye composition according to claim 9, which consists of component a, component B and component C.
11. The disperse blue dye composition according to claim 9, further comprising component D, wherein:
component A is selected from at least one of the formulae (I-1) to (I-3),
the component B is at least one selected from the formulas (II-1) to (II-4),
the component C is at least one selected from the formulas (III-1) to (III-3),
the component D is at least one selected from the formulas (IV-1) to (IV-3) and (V-1) to (V-4),
in the composition, the mass percentage of the component A is 20-75%, the mass percentage of the component B is 20-75%, the mass percentage of the component C is 5-40%, and the mass of the component D is more than 0 and not more than 40% of the total mass of the components A-C;
12. the disperse blue dye composition according to claim 11, consisting of component a, component B, component C and component D.
13. A disperse blue dye product comprising an auxiliary agent and the disperse blue dye composition of claim 1, wherein the weight ratio of the auxiliary agent to the disperse blue dye composition is 0.2-5:1, and the auxiliary agent is a dispersing agent, a dispersing agent or other surfactants commonly used in disperse dye compounding: naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonic acid formaldehyde condensate, and anhydrous sodium sulfate.
14. A disperse blue dye product comprising an auxiliary agent and the disperse blue dye composition of claim 3, wherein the weight ratio of the auxiliary agent to the disperse blue dye composition is 0.2-5:1, and the auxiliary agent is a dispersing agent, a dispersing agent or other surfactants commonly used in disperse dye compounding: naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonic acid formaldehyde condensate, and anhydrous sodium sulfate.
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