CN113136114A - High-fastness disperse dye composition and dye product - Google Patents

High-fastness disperse dye composition and dye product Download PDF

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CN113136114A
CN113136114A CN202110306468.3A CN202110306468A CN113136114A CN 113136114 A CN113136114 A CN 113136114A CN 202110306468 A CN202110306468 A CN 202110306468A CN 113136114 A CN113136114 A CN 113136114A
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component
fastness
disperse dye
dye composition
fastness disperse
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王羽蘅
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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
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008Preparations of disperse dyes or solvent 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
    • C09B67/0033Blends 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/18Azo dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/6033Natural or regenerated cellulose using dispersed dyes

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

Abstract

The invention provides a high-fastness blue-to-black disperse dye composition and a dye product, wherein when the disperse dye composition and the dye product are applied to dyeing of hydrophobic fiber materials, the disperse dye composition and the dye product have good lifting power and excellent color fastness, and particularly have outstanding color fastness to washing.

Description

High-fastness disperse dye composition and dye product
Technical Field
The invention relates to a high-fastness disperse dye composition and a dye product, in particular to a high-fastness blue-to-black disperse dye composition and a dye product which are suitable for printing and dyeing hydrophobic fiber materials.
Background
In order to improve the additional performance of textiles, special after-finishing treatments such as heat setting, softening, moisture absorption and sweat releasing and the like are usually carried out on the textiles, and because the conventional disperse dyes have poor heat migration resistance, when deep-color polyester textiles are dyed, the dyes migrate to the surface layer of the fibers from the inside of the fibers through fiber capillaries in the after-finishing high-temperature tentering and shaping process, so that the dyes are accumulated on the surface of the fibers, other textiles are stained, the color fastness to friction and washing is obviously reduced, and the requirement of the textiles on the fastness cannot be met. For example: the AATCC test standard of the textile is the American dyers and chemists' association standard, has larger difference with the national standard (GB/T series) and the international standard (ISO series), and the color fastness to washing of the same product in the AATCC series test is obviously lower than that in the national standard.
With the continuous research and development of dye workers, high-fastness disperse dyes are not on the market, the fastness performance is improved, but unsatisfactory places exist frequently, the fastness, the lifting power, the color fastness and the cost are difficult to be considered, and especially the requirements of the fastness performance on high-grade fabrics cannot be completely met. Therefore, a new class of high-fastness disperse dyes is needed to be developed to meet the dyeing requirements of high-grade polyester fabrics or polyester spandex stretch fabrics. The prior document CN104987751B and the like provides a disperse blue-black dye composition with excellent fastness, but has room for further improvement.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a high-fastness disperse dye composition and a dye product, which have good lifting power and excellent color fastness when applied to dyeing of hydrophobic fiber materials, and particularly have outstanding color fastness to washing.
The technical scheme of the invention is as follows:
a high-fastness disperse dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of compounds (I) in a general formula, the component B is selected from at least one of compounds (II-1) to (II-7), the component C is selected from at least one of compounds (III-1) to (III-5), based on the component A, the component B and the component C, the mass fraction of the component A is 10-95%, the mass fraction of the component B is 1-45%, and the mass fraction of the component C is 1-45%;
Figure BDA0002987801860000011
in the formula (I), the compound is shown in the specification,
R1is hydrogen, methoxy or ethoxy;
R2is methyl or-NHCOR4Wherein R is4Is methyl or ethyl;
R3is methyl or ethyl;
Figure BDA0002987801860000021
Figure BDA0002987801860000031
Figure BDA0002987801860000041
further, the high-fastness disperse dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of compounds (I) in the general formula, the component B is selected from at least one of compounds (II-1) to (II-7), the component C is selected from at least one of compounds (III-1) to (III-5), and based on the component A, the component B and the component C, the mass fraction of the component A is 10-95% (preferably 20-90%), the mass fraction of the component B is 1-45% (preferably 5-40%), and the mass fraction of the component C is 1-45% (preferably 5-40%).
Preferably, the component A is selected from one of the following formulas (I-1) to (I-5) or a mixture of two or more of the following formulas in any proportion:
Figure BDA0002987801860000042
Figure BDA0002987801860000051
further preferably, the component A is selected from one of the following formulas (I-1), (I-3) or a mixture of two in any ratio:
Figure BDA0002987801860000052
preferably, the component B is selected from compounds represented by the formula (II-1):
Figure BDA0002987801860000053
preferably, the component C is selected from compounds represented by the formula (III-1):
Figure BDA0002987801860000054
when the high-fastness disperse dye composition is sold as a commodity or applied to textile material coloring, an auxiliary agent is usually added for post-treatment. Therefore, the invention also provides a high-fastness disperse dye product which contains the high-fastness 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, the high-fastness disperse dye product consists of the high-fastness 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 preferably one or a mixture of more than two of the following materials: lignosulfonates, such as sodium lignosulfonate (lignin 85A, lignin 83A); alkyl naphthalene sulfonic acid formaldehyde condensates, such as methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF); naphthalenesulfonic acid formaldehyde condensates (diffuser NNO); a benzylnaphthalenesulfonic acid formaldehyde condensate (diffusing agent CNF), and the like.
The preparation method of the high-fastness disperse dye product comprises the following steps:
mixing the dye monomer compounds (crude dyes) which form the high-fastness disperse 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 high-fastness disperse dye product is liquid after being ground by a sand mill or a grinding machine, and can be powdery and granular after being spray-dried, which is a preparation method well known by the technical personnel in the field.
In the present invention, the dye compounds represented by the formulae (I-1) to (I-5), (II-1) to (II-7), (III-1) to (III-5) can be conveniently synthesized in a manner known to those skilled in the art, and can be prepared by a method described in patents CN104059377A, CN1208057A, GB1326124A, JPS58152056A and CN 101081838A or a similar method, and commercially available products can be used.
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. Among them, the common dip dyeing method is, for example: pretreating a 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, carrying out reduction washing, and drying; direct printing is for example: the method comprises the steps of carrying out dyeing pretreatment on the fabric, drying, setting, printing disperse dye color paste on a printing machine, carrying out steaming, fixing the color of the dye on the fabric by using a steaming mode, finally washing, and tentering and setting.
The invention has the beneficial effects that:
the component A adopts a cyanide-structured high-fastness compound, has higher molar extinction coefficient, better fastness and longer absorption wavelength, and is favorable for preparing dark blue and black with higher strength and better deep color;
and (II) compared with other high-fastness compounds with cyanide structures, the selected component A not only has the characteristic of high washing fastness, but also has better stability of a dye bath, so that the comprehensive performance is more outstanding. The blue-black product has good compound synergistic effect, so that the blue-black product has good deep dyeing property, light fastness, sublimation fastness and washing fastness for dyeing and printing of terylene and blended fabrics thereof, especially terylene-ammonia blended fabrics.
And (III) the dye product of the invention is also suitable for being compounded and mixed with other disperse dyes, for example, the dye product can be mixed with high-fastness dark blue and black which are compounded with non-cyanide blue components, the color fastness is better, and the economy is very good.
The blue-to-black disperse dye composition and the dye product provided by the invention have the characteristics of good lifting force, excellent friction resistance and washing fastness and the like when being applied to dyeing of hydrophobic fiber materials.
Detailed Description
The invention is further described below by means of specific examples, without the scope of protection of the invention being limited thereto.
Example 1:
50 g of a compound shown as a formula (I-1), 35 g of a compound shown as a formula (I-3), 2g of a compound shown as a formula (II-2), 8 g of a compound shown as a formula (II-4), 5 g of a compound shown as a formula (III-1) and 200 g of a dispersing agent 85A 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 dark blue with excellent fastness properties for fabrics:
Figure BDA0002987801860000061
Figure BDA0002987801860000071
example 2:
40 g of a compound of a formula (I-1), 30 g of a compound of a formula (II-1), 30 g of a compound of a formula (III-1) and 200 g of a dispersing agent 85A 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 black with excellent fastness properties to fabrics:
Figure BDA0002987801860000072
Figure BDA0002987801860000081
example 3:
adding 650 g of water into 40 g of a compound of a formula (I-1), 12 g of a compound of a formula (II-6), 12 g of a compound of a formula (II-4), 6 g of a compound of a formula (II-5), 30 g of a compound of a formula (III-1) and 200 g of a dispersing agent 85A, mixing, grinding, dispersing and drying to obtain a finished product, wherein the dye can provide black with excellent fastness properties to fabrics:
Figure BDA0002987801860000082
Figure BDA0002987801860000091
examples 4 to 11:
according to the method described in the example 1 or 2, except that the structures and the weights of the components A-C in the table 2 and the auxiliary agents are adopted, 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 blue to black tones with excellent fastness performance for fabrics.
Compounds in which component a employs different substituent groups are shown in table 1:
Figure BDA0002987801860000092
in the formula (I), the compound is shown in the specification,
R1is hydrogen, methoxy or ethoxy;
R2is methyl or-NHCOR4Wherein R is4Is methyl or ethyl;
R3is methyl or ethyl.
TABLE 1
Component A R1 R2 R3
Formula (I-1) OCH3 NHCOCH3 CH3
Formula (I-2) OCH3 NHCOCH3 C2H5
Formula (I-3) H NHCOCH3 CH3
Formula (I-4) H NHCOCH3 C2H5
Formula (I-5) OCH3 CH3 CH3
Formula (I-6) H CH3 CH3
Formula (I-7) OCH3 NHCOC2H5 CH3
Formula (I-8) H NHCOC2H5 CH3
TABLE 2 (Unit: gram)
Figure BDA0002987801860000093
Figure BDA0002987801860000101
Comparative example:
example 1 in patent CN104987751B was taken as comparative example 1;
example 4 in patent CN104987751B was taken as comparative example 2;
example 1 in patent CN102153890A was taken as comparative example 3.
Dyeing example 1:
the specific test method is as follows:
according to a method similar to GB/T2394-2006, 0.5 g of the finished dyes of examples 1-11 and comparative examples 1-3 are respectively weighed into 500ml of water to prepare a disperse dye suspension, wherein the content of the filter cake of comparative example 3 is 33.3%. Sucking 50ml of the dispersed suspension, mixing with 50ml of water, adjusting the pH value of a dye bath to 4.0 by using acetic acid, then heating to 60 ℃, simultaneously adding 2g of polyester/ammonia (80/20, T75/72) fiber cloth to carry out high-temperature high-pressure dyeing, heating to 130 ℃ within 35min, keeping the temperature for 60min, cooling to 80 ℃, sampling and drying. The cloth-like color was observed to be blue to black.
Then carrying out reduction washing under the following conditions: NaOH 2g/l, sodium hydrosulfite 3g/l, 85 ℃ 15 min.
The light fastness, sublimation fastness and color fastness to washing of the fabric are tested by GB/T8427-1998, GB/T5718-1997 and GB/T3921-2008, and the test results are shown in Table 3:
TABLE 3 (Unit: grade)
Figure BDA0002987801860000102
Figure BDA0002987801860000111
From the above table 3, it can be seen that the high-fastness disperse dye composition disclosed by the invention has the fastness properties such as sublimation, washing resistance and staining resistance which are better than those of comparative examples 1-2 after the dyed fabric is subjected to after-finishing and high-temperature heat setting, and can better meet the printing and dyeing requirements of the fabric with high fastness.
Dyeing example 2:
the specific test method is as follows:
according to a method similar to GB/T2394-2006, 0.5 g of the finished dyes of examples 1-11 and comparative example 3 are respectively weighed into 500ml of water to prepare a disperse dye suspension, wherein the filter cake content of comparative example 3 is 33.3%. And (2) respectively sucking 20ml of the dispersed suspension in each sample cup, mixing the dispersed suspension with 50ml of water, respectively adjusting the pH value of a dye bath to 3.5, 4.0, 4.3, 4.5 and 5.0 by using an acetic acid and sodium acetate buffer system, then heating to 60 ℃, simultaneously respectively adding 2g of polyester/ammonia (80/20, T75/72) fiber cloth for high-temperature high-pressure dyeing, heating to 130 ℃ within 35min, keeping the temperature for 60min, cooling to 80 ℃, sampling and drying. The cloth-like color was observed to be blue to black.
The ratio of pH: the fabric samples dyed at 4.0 were used as standards and the strength of the dyed fabric samples was measured separately at different pH baths, see table 4:
table 4 (unit:%)
Name (R) pH 4.0 pH 3.5 pH 4.3 pH 4.5 pH 5.0
Example 1 100 100 100 100 89
Example 2 100 100 100 100 90
Example 3 100 100 100 100 91
Example 4 100 100 100 100 88
Examples5 100 100 100 100 89
Example 6 100 100 100 100 92
Example 7 100 100 100 100 91
Example 8 100 100 100 100 92
Example 9 100 100 100 100 91
Example 10 100 100 100 100 89
Example 11 100 100 100 100 92
Comparative example 3 100 100 100 95 87
As can be seen from Table 4, the pH dependency of examples 1 to 11 was 3.5 to 4.5, while that of comparative example 3 was 3.5 to 4.3, indicating that the bath stability of comparative example 3 was insufficient, and although the present invention was of the same level as that of the dye described in CN102153890A in terms of washing fastness, the pH dependency was improved, the control during dyeing was easier, and the practical use was very advantageous.

Claims (10)

1. The high-fastness disperse dye composition is characterized by comprising a component A, a component B and a component C, wherein the component A is selected from at least one of compounds (I) in a general formula, the component B is selected from at least one of compounds (II-1) to (II-7), the component C is selected from at least one of compounds (III-1) to (III-5), and based on the component A, the component B and the component C, the mass fraction of the component A is 10-95%, the mass fraction of the component B is 1-45%, and the mass fraction of the component C is 1-45%;
Figure FDA0002987801850000011
in the formula (I), the compound is shown in the specification,
R1is hydrogen, methoxy or ethoxy;
R2is methyl or-NHCOR4Wherein R is4Is methyl or ethyl;
R3is methyl or ethyl;
Figure FDA0002987801850000012
Figure FDA0002987801850000021
Figure FDA0002987801850000031
2. the high-fastness disperse dye composition according to claim 1, wherein the mass fraction of the component A is 20 to 90%, the mass fraction of the component B is 5 to 40%, and the mass fraction of the component C is 5 to 40% based on the component A, the component B and the component C.
3. The high-fastness disperse dye composition according to claim 1, wherein the component A is selected from one of the following formulas (I-1) to (I-5) or a mixture of two or more of them in any proportion:
Figure FDA0002987801850000032
Figure FDA0002987801850000041
4. the high-fastness disperse dye composition according to claim 1, wherein the component A is selected from one of the following formulas (I-1), (I-3) or a mixture of the two in any proportion:
Figure FDA0002987801850000042
5. the high-fastness disperse dye composition according to claim 1, wherein the component B is selected from compounds represented by the formula (II-1):
Figure FDA0002987801850000043
6. the high-fastness disperse dye composition according to claim 1, wherein the component C is selected from compounds represented by the formula (III-1):
Figure FDA0002987801850000051
7. the high-fastness disperse dye composition according to any one of claims 1 to 6, wherein the high-fastness disperse dye composition consists of a component A, a component B and a component C.
8. A high-fastness disperse dye product is characterized by comprising the high-fastness disperse dye composition as defined in claim 1 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5: 1.
9. The high-fastness disperse dye preparation according to claim 8, wherein the auxiliary agent is one of the following or a mixture of two or more thereof: lignosulfonate, alkylnaphthalenesulfonic acid-formaldehyde condensate, naphthalenesulfonic acid-formaldehyde condensate, and benzylnaphthalenesulfonic acid-formaldehyde condensate.
10. Use of a high-fastness disperse dye composition according to claim 1 or of a high-fastness disperse dye preparation according to claim 8 for dyeing hydrophobic fibre materials.
CN202110306468.3A 2021-03-23 2021-03-23 High-fastness disperse dye composition and dye product Pending CN113136114A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105038315A (en) * 2015-07-31 2015-11-11 杭州福莱蒽特精细化工有限公司 Compound scattered black dye high in color fastness
CN105838109A (en) * 2016-04-29 2016-08-10 浙江龙盛集团股份有限公司 High-fastness blue to black disperse dye composition and dye product
CN106833019A (en) * 2016-12-31 2017-06-13 浙江龙盛化工研究有限公司 A kind of fastness high is blue to black disperse dye composition and dye preparations
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105038315A (en) * 2015-07-31 2015-11-11 杭州福莱蒽特精细化工有限公司 Compound scattered black dye high in color fastness
CN105838109A (en) * 2016-04-29 2016-08-10 浙江龙盛集团股份有限公司 High-fastness blue to black disperse dye composition and dye product
CN106833019A (en) * 2016-12-31 2017-06-13 浙江龙盛化工研究有限公司 A kind of fastness high is blue to black disperse dye composition and dye preparations
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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