CN106700647B - Orange-red disperse dye composition and dye product - Google Patents

Orange-red disperse dye composition and dye product Download PDF

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Publication number
CN106700647B
CN106700647B CN201611113384.3A CN201611113384A CN106700647B CN 106700647 B CN106700647 B CN 106700647B CN 201611113384 A CN201611113384 A CN 201611113384A CN 106700647 B CN106700647 B CN 106700647B
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component
dye composition
orange
dye
red
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CN106700647A (en
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高怀庆
陈佳蕾
张友珍
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH 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
    • C09B67/0033—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
    • 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
    • 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
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/46—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing natural macromolecular substances or derivatives thereof
    • 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)
  • 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 orange-red dye composition and a dye product, wherein the disperse orange-red dye composition comprises a component A and a component B, 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 percentage of the component A is 1-99%, and the mass percentage of the component B is 1-99%. The disperse orange-red dye product contains the disperse orange-red dye composition and an auxiliary agent, and the weight ratio of the auxiliary agent to the disperse orange-red dye composition is 0.2-5: 1. The orange-red disperse dye composition and the dye product provided by the invention have excellent fastness to soaping, perspiration and rubbing when being applied to dyeing of hydrophobic fiber materials.

Description

Orange-red disperse dye composition and dye product
(I) technical field
The invention relates to a disperse orange to red dye composition and a dye product, in particular to a disperse orange to red dye composition and a dye product which are suitable for printing and dyeing hydrophobic fiber materials.
(II) background of the invention
After the polyester-ammonia fabric is dyed by the disperse dye, when high-temperature treatment (such as heat setting) is carried out, because the auxiliary agent on the outer layer of the fiber generates a dissolving effect on the dye at high temperature, the dye is widened and migrated to the surface layer of the fiber from the inside of the fiber through a fiber capillary at high temperature, so that the dye is accumulated on the surface layer of the fiber, and a series of influences, such as color fastness reduction and the like, are caused.
The present applicant has provided in CN101215245A a monoazo compound having excellent lifting power, reproducibility and excellent wet-processing fastness, high color strength. To date, the applicant has found that the use of such monoazo compounds for color matching makes it possible to solve the above-mentioned problems and to obtain a group of disperse orange to red dye compositions having excellent properties.
Disclosure of the invention
The invention provides an orange-red to red disperse dye composition and a dye product, which have excellent soaping resistance, perspiration resistance and rubbing fastness when applied to dyeing of hydrophobic fiber materials.
The technical scheme adopted by the invention is as follows:
the orange-red 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 1-99%, and the mass percent of the component B is 1-99%:
Figure BDA0001171590140000011
in formula (I):
n is 1 or 2;
R1、R2each independently is methyl or ethyl;
X4when it is nitro, X5、X6Each independently is chlorine, bromine or hydrogen; x4When it is chlorine or bromine, X5、X6One is nitro and the other is hydrogen.
Y is hydroxy, C1～C4Alkyl or C1～C4An alkoxy group.
In formula (II):
m is 1 or 2;
R3、R4each independently is methyl or ethyl;
X1when it is nitro, X2、X3Each independently is chlorine, bromine or hydrogen; x1When it is chlorine or bromine, X2、X3One is nitro and the other is hydrogen.
Preferably, the orange-red dye composition comprises a component A and a component B, wherein the component A accounts for 30-80% by mass and the component B accounts for 20-70% by mass based on the component A and the component B.
More preferably, the orange-red dye composition comprises a component A and a component B, wherein the mass percentage of the component A is 1-99% (preferably 30-80%), and the mass percentage of the component B is 1-99% (preferably 20-70%).
Further, the dye component A is preferably at least one of dye compounds represented by the formulae (I-1) to (I-13);
Figure BDA0001171590140000021
Figure BDA0001171590140000031
Figure BDA0001171590140000041
further, the dye component B is preferably at least one of dye compounds represented by the formulae (II-1) to (II-9):
Figure BDA0001171590140000042
Figure BDA0001171590140000051
the disperse orange to red dye composition according to the invention preferably comprises a component a and a component B, wherein:
the component A is at least one selected from formulas (I-1) to (I-3);
the component B is selected from at least one of formulas (II-1) to (II-3);
based on the component A and the component B, the mass percentage of the component A is 1-99%, and the mass percentage of the component B is 1-99%.
Alternatively, the disperse orange to red dye composition according to the invention preferably consists of component a and component B, wherein:
the component A is at least one selected from formulas (I-1) to (I-3);
the component B is selected from at least one of formulas (II-1) to (II-3);
based on the component A and the component B, the mass percentage of the component A is 1-99%, and the mass percentage of the component B is 1-99%.
The orange-to-red disperse dye composition of the invention can optionally be added with a certain amount of toning components, such as C.I. disperse violet 93, C.I. disperse blue 366, C.I. disperse blue 165, C.I. disperse orange 288, C.I. disperse yellow 118 and the like.
When the orange to red disperse dye composition is sold as a commodity or applied to coloring textile materials, an auxiliary agent is usually added for post-treatment. Therefore, the invention also provides a disperse orange-red dye product, which contains the disperse orange-red 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, the disperse orange to red dye product consists of the disperse orange to red 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 preferably selected from one or a mixture of more than two of the following components: lignosulfonates (e.g., sodium lignosulfonate (lignin 85A, lignin 83A)), alkylnaphthalenesulfonic acid-formaldehyde condensates (e.g., methylnaphthalenesulfonic acid-formaldehyde condensate (dispersant MF)), naphthalenesulfonic acid-formaldehyde condensate (dispersant NNO), benzylnaphthalenesulfonic acid-formaldehyde condensate (dispersant CNF)), and the like.
The preparation method of the disperse orange to red dye product comprises the following steps:
mixing dye monomer compounds (crude dyes) for forming the disperse orange to red dye composition according to a ratio, and then carrying out microparticulation by a grinder such as a sand mill or a grinding machine in the presence of an auxiliary agent and water; alternatively, the dye monomer compound 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 orange to red disperse dye product of the present invention is liquid after being ground in a sand mill or a grinder, and may be in the form of powder or granules after being spray-dried, which is a well-known preparation method for those skilled in the art.
In the present invention, the dye compounds of formula (I) can be conveniently synthesized in a manner well known to those skilled in the art, and can be prepared by a method described in patent CN101215245 or a similar method, or can be commercially available. The dye compound shown in the formula (II) is preferably prepared by adopting the raw materials, diazo process and coupling process in the patent CN101215245, and the dye mixture shown in the formula (I) and the formula (II) is directly synthesized without refining a dye filter cake; or refining the dye of formula (I) according to a conventional DMF purification process, and refining the mother liquor with DMF for the second time to obtain the dye compound of formula (II).
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 orange-red disperse dye composition and the dye product provided by the invention have the characteristics of excellent soaping resistance, sweat resistance, rubbing fastness and the like 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
Adding 21.8g of m-aminophenol, 108g of methyl acrylate, 25g of acetic acid and 5g of sodium bromide into a three-neck flask, heating to 90-95 ℃, reacting for 19 hours, then decompressing and distilling out redundant methyl acrylate and acetic acid at the temperature, and cooling to 30-35 ℃ to obtain the 3-hydroxy-N, N-dimethoxycarbonyl ethylaniline solution.
Adding 80g of sulfuric acid (98%) and 80g of 20% nitrosyl sulfuric acid into a three-neck flask, stirring for 30-60min, controlling the temperature to be 10-30 ℃, adding 0.2mol (41.4 g) of 2, 6-dichloro-4-nitroaniline into the three-neck flask within 2 hours under stirring, keeping the temperature for reaction for about 5 hours, and diazotizing to finish.
Taking the 3-hydroxy-N, N-dimethoxycarbonylethylaniline solution prepared in the example 1, pulping at 10 ℃, controlling the temperature below 10 ℃, adding a small amount of sulfamic acid and an emulsifier, dropwise adding the diazo liquid for about 2 hours, preserving the temperature for 2 hours after the addition, and performing suction filtration to obtain a red dye mixture of the following formulas (I-1) and (II-1).
Taking 100 g of the dye mixture, wherein the weight ratio of the formula (I-1) to the formula (II-1) is about 65:35, respectively adding 225 g of dispersing agent MF and 800 g of pure water, uniformly grinding, drying and dehydrating to obtain the corresponding commercial dye.
Figure BDA0001171590140000071
Alternatively, the mixture may be isolated by several DMF purifications, usually without isolation, as follows.
Example 2
60 g of a compound of a formula (I-2), 40 g of a compound of a formula (II-2) and 200 g of a dispersing agent MF are mixed with 650 g of water, and then the mixture is ground, dispersed and dried to obtain a finished product, and the dye can provide red with excellent fastness properties for fabrics.
Figure BDA0001171590140000081
Example 3:
50 g of a compound shown in a formula (I-3), 50 g of a compound shown in a formula (II-1) and 200 g of a dispersing agent MF are mixed with 650 g of water, and then the mixture is ground, dispersed and dried to obtain a finished product, wherein the dye can provide red with excellent fastness properties for fabrics.
Figure BDA0001171590140000082
Examples 4 to 21:
according to the method described in example 1 or 2, except that the structure and weight of the component A, B in Table 1 are adopted, 200 g of auxiliary agent (150 g of dispersing agent MF and 50 g of lignin 85A) are added, 650 g of water is added for blending to prepare slurry, and the slurry is ground, dispersed and dried to prepare the finished product, and the dye can provide orange or red with excellent fastness performance to fabrics.
TABLE 1
Figure BDA0001171590140000083
Figure BDA0001171590140000091
Dyeing example:
respectively selecting the disperse dyes prepared in the embodiments 1-21 and the dye prepared in the embodiment 5 (comparative example 1) in the patent CN101215245, and adopting a conventional high-temperature high-pressure dyeing method and heat setting to process the terylene/spandex mixed fabric, wherein in the processing process, the dyeing depth (o.w.f) is controlled to be 1.0 percent, the bath ratio is 1: 20, the pH value of a dyeing bath is adjusted to be 4-5, the terylene/spandex mixed fabric is dyed at room temperature, the temperature is raised to 130 ℃ at the rate of 1 ℃/min, the temperature is kept for 45min, the terylene/spandex mixed fabric is reduced, cleaned, washed and dried according to the conventional method, and is heat set at the temperature of 180 ℃ for. The soaping resistance, the friction resistance and the perspiration fastness were tested according to GB/T3921, GB/T3920 and GB/T3922 respectively, and the results are shown in the following table 2:
TABLE 2
Figure BDA0001171590140000101
Figure BDA0001171590140000111
From the above, the mixed dye of the present invention has more excellent color fastness to perspiration than the prior art.

Claims (9)

1. The orange-red 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 1-99%, and the mass percent of the component B is 1-99%:
Figure FDA0002717040920000011
in formula (I):
n is 1 or 2;
R1、R2each independently is methyl or ethyl;
X1when it is nitro, X2、X3Each independently is chlorine, bromine or hydrogen; x1When it is chlorine or bromine, X2、X3One is nitro and the other is hydrogen;
y is hydroxy, C1～C4Alkyl or C1～C4An alkoxy group;
in formula (II):
m is 1 or 2;
R3、R4each independently is methyl or ethyl;
X4when it is nitro, X5、X6Each independently is chlorine, bromine or hydrogen; x4When it is chlorine or bromine, X5、X6One is nitro and the other is hydrogen.
2. The disperse orange to red dye composition of claim 1, wherein: y is a hydroxyl group.
3. The disperse orange to red dye composition according to claim 1, wherein said component a is at least one selected from the group consisting of dye compounds represented by formulae (i-1) to (i-13);
Figure FDA0002717040920000012
Figure FDA0002717040920000021
Figure FDA0002717040920000031
4. the orange-to-red disperse dye composition according to claim 1, wherein said component B is at least one selected from the group consisting of dye compounds represented by formulae (ii-1) to (ii-9):
Figure FDA0002717040920000032
Figure FDA0002717040920000041
Figure FDA0002717040920000051
5. the disperse orange to red dye composition according to claim 1, wherein the disperse orange to red dye composition comprises component A and component B, wherein the mass percent of component A is 30-80% and the mass percent of component B is 20-70% based on the component A and the component B.
6. The disperse orange to red dye composition of claim 5, wherein:
the component A is at least one selected from formulas (I-1) to (I-3);
the component B is at least one selected from formulas (II-1) to (II-3).
7. A disperse orange to red dye product comprising the disperse orange to red dye composition of claim 1 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse orange to red dye composition is 0.2-5: 1.
8. Use of a disperse orange to red dye composition according to claim 1 in printing hydrophobic fibre materials.
9. Use of a disperse orange to red dye preparation according to claim 7 in printing hydrophobic fibre materials.
CN201611113384.3A 2016-12-06 2016-12-06 Orange-red disperse dye composition and dye product Active CN106700647B (en)

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