CN109486238B - Disperse red dye composition - Google Patents
Disperse red dye composition Download PDFInfo
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- CN109486238B CN109486238B CN201811493105.XA CN201811493105A CN109486238B CN 109486238 B CN109486238 B CN 109486238B CN 201811493105 A CN201811493105 A CN 201811493105A CN 109486238 B CN109486238 B CN 109486238B
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- component
- dye composition
- disperse red
- red dye
- auxiliary agent
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- 239000000203 mixture Substances 0.000 title claims abstract description 36
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 239000001044 red dye Substances 0.000 title claims abstract description 30
- 238000004043 dyeing Methods 0.000 claims abstract description 24
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000004744 fabric Substances 0.000 claims description 13
- 229920000728 polyester Polymers 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 claims description 3
- NMDKWAQVRNUKQH-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid formaldehyde Chemical compound C=O.C(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NMDKWAQVRNUKQH-UHFFFAOYSA-N 0.000 claims description 2
- 229920001732 Lignosulfonate Polymers 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 claims 1
- 239000002657 fibrous material Substances 0.000 abstract description 8
- 230000002209 hydrophobic effect Effects 0.000 abstract description 8
- 238000005406 washing Methods 0.000 abstract description 6
- 238000000859 sublimation Methods 0.000 abstract description 4
- 230000008022 sublimation Effects 0.000 abstract description 4
- 239000000975 dye Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 229920002334 Spandex Polymers 0.000 description 3
- 239000000986 disperse dye Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000004759 spandex Substances 0.000 description 3
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 2
- 229920004933 Terylene® Polymers 0.000 description 2
- 238000010017 direct printing Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- WQHQCQSAAOGHQP-UHFFFAOYSA-N formaldehyde;2-methylnaphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WQHQCQSAAOGHQP-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- 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
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- 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
- D06P1/16—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
- D06P1/20—Anthraquinone 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- 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
- D06P3/8214—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups
Landscapes
- 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 red dye composition, which consists of a component A, a component B and an auxiliary agent, wherein the component A is selected from one or more compounds shown in a formula (I), and the component B is selected from one or more compounds shown in a formula (II). When the disperse red dye composition is applied to dyeing of hydrophobic fiber materials, the disperse red dye composition has the characteristics of good lifting force, sublimation resistance, friction resistance, washing resistance, light fastness and the like.
Description
(I) technical field
The invention relates to a disperse red dye composition, in particular to a disperse red dye composition suitable for printing and dyeing hydrophobic fiber materials.
(II) background of the invention
The dye C.I. disperse red 60 has bright color, good level-dyeing property and lifting power, but the dye has poor light fastness and sublimation fastness, and is easy to have problems in textile printing and dyeing processing, such as sensitivity to metal ions in water, poor acid-base adaptability of a dyeing solution, low dye utilization rate and the like. For this reason, studies have been made in the art on alternatives to disperse red 60, for example, patent CN106189360A discloses a disperse red dye composition which, although excellent in color fastness when dyeing polyester fabrics, is unsatisfactory in dyeing properties when dyeing polyester/spandex blended fabrics.
Disclosure of the invention
In order to solve the problems, the invention provides a disperse red dye composition which has the characteristics of excellent fastness, good lifting force and the like when being applied to dyeing of hydrophobic fiber materials, particularly terylene/spandex blended fabrics.
According to the technical scheme adopted by the invention, the disperse red dye composition is characterized by comprising a component A, a component B and an auxiliary agent, wherein the component A is selected from one or more compounds shown in a formula (I), the component B is selected from one or more compounds shown in a formula (II), based on the component A, the component B and the auxiliary agent, the mass percentage of the component A is 5-45%, the mass percentage of the component B is 5-45%, and the balance is the auxiliary agent:
in the formula (I), the compound is shown in the specification,
R1is hydrogen, halogen or cyano;
R2is hydrogen or C1～C4An acetylamino group;
R3is-C2H4CN or-C2H4OCOCH3；
In the formula (II), the compound is shown in the specification,
R4is-H, -SO2NHC2H4OC2H5or-OCH3。
Preferably, based on the component A, the component B and the auxiliary agent, the mass percentage of the component A is 10-45%, the mass percentage of the component B is 10-45%, and the balance is the 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: naphthalenesulfonic acid-formaldehyde condensates, lignosulfonates, alkylnaphthalenesulfonic acid-formaldehyde condensates (e.g., methylnaphthalenesulfonic acid-formaldehyde condensate (dispersant MF)), naphthalenesulfonic acid-formaldehyde condensate (dispersant NNO), benzylnaphthalenesulfonic acid-formaldehyde condensate (dispersant CNF), sodium lignosulfonates (lignin 85A, lignin 83A), and the like.
Further, the component a is preferably selected from one of the following formulae or a mixture of two or more thereof:
the component B is preferably selected from one or a mixture of two or more of the following formulae:
furthermore, the disperse red dye composition consists of a component A, a component B and an auxiliary agent,
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-2).
Based on the component A and the component B, the mass percentage of the component A is 10-45%, the mass percentage of the component B is 10-45%, and the balance is an auxiliary agent.
Or, the disperse red dye composition of the invention comprises a component A, a component B and an auxiliary agent, wherein: the component A is shown as a formula (I-1), and the component B is shown as a formula (II-1).
It should be noted that, due to the particularity of the dye industry, the component a and the component B are difficult to be made into pure products and usually contain a small amount of moisture and a small amount of physical impurities, and the presence of the moisture and the physical impurities is also within the tolerance range of the present invention.
The preparation method of the disperse red dye composition comprises the following steps:
mixing the dye monomer compounds (crude dyes) which form the disperse 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 disperse red dye composition of the present invention is liquid after being ground by a sand mill or a grinder, and may be in the form of powder or granules after being spray-dried, which is a preparation method well known to those skilled in the art.
In the present invention, the dye compounds represented by the formulae (I) and (II) can be conveniently synthesized by a method known to those skilled in the art, and can be prepared by a method described in patents CN1183438A and CN101182390A or a similar method, or by a commercially available method.
The disperse red dye composition can be used for dyeing hydrophobic fiber materials (such as polyester and blended fabrics thereof) in a conventional mode in the industry, such as a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be used for direct printing. Wherein, the common dip-dyeing method comprises the steps of pretreating the hydrophobic fiber material, putting the 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 red dye composition provided by the invention has the characteristics of good lifting force, excellent sublimation resistance, friction resistance, washing resistance, light 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:
30 g of a compound of a formula (I-1), 10 g of a compound of a formula (II-1) and 60 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.
Example 2:
the dye can provide red with excellent fastness performance to fabrics, and is prepared by mixing 5 g of a compound shown as a formula (I-1), 15 g of a compound shown as a formula (I-2), 45 g of a compound shown as a formula (II-1) and 35 g of a dispersing agent MF with 800 g of water, grinding, dispersing and drying.
Examples 3 to 15:
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, the auxiliary agent is added, 800 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 red with excellent fastness performance to fabrics.
TABLE 1
Comparative example 1
The dye compositions prepared in example 2 and example 8 described in patent CN106189360 were respectively used as comparative example 1 and comparative example 2.
Dyeing example:
selecting the disperse dyes prepared in the embodiments 1-15, the comparative examples 1 and the comparative examples 2, treating the terylene/spandex fabric by adopting a conventional high-temperature high-pressure dyeing method, controlling the dyeing depth (o.w.f) to be 4.0 percent in the treatment process, controlling the bath ratio to be 1: 25, adjusting the pH value of a dyeing bath to be 4.5-5, dyeing at room temperature, heating to 125 ℃ at the rate of 1 ℃/min, preserving the temperature for 35min, reducing, cleaning, washing and drying according to a conventional method to obtain the red dyed fabric. Sublimation resistance, rubbing resistance, color fastness to washing and light fastness were tested according to ISO 105-P01, ISO 105-X12, AATCC 61-2A, GB/T8427, respectively, and the results are shown in Table 2 below:
TABLE 2
Therefore, when the disperse red dye composition is used for printing and dyeing polyester blended fabrics, compared with the existing disperse red dye, the disperse red dye composition has outstanding color fastness performance.
Claims (8)
1. A disperse red dye composition comprises a component A, a component B and an auxiliary agent, wherein the component A is selected from one or more compounds shown in a formula (I), the component B is selected from one or more compounds shown in a formula (II), based on the component A, the component B and the auxiliary agent, the mass percent of the component A is 5-45%, the mass percent of the component B is 5-45%, and the balance is the auxiliary agent:
in the formula (I), the compound is shown in the specification,
R1is hydrogen or cyano;
R2is hydrogen or acetylamino;
R3is-C2H4CN or-C2H4OCOCH3；
In the formula (II), the compound is shown in the specification,
R4is-H, -SO2NHC2H4OC2H5or-OCH3。
2. A disperse red dye composition according to claim 1 wherein: based on the component A, the component B and the auxiliary agent, the mass percentage of the component A is 10-45%, the mass percentage of the component B is 10-45%, and the balance is the auxiliary agent.
3. A disperse red dye composition according to claim 1 wherein: the component A is selected from one of the following formulas or a mixture of more than two of the following formulas:
4. a disperse red dye composition according to claim 1 wherein: the component B is selected from one of the following formulas or a mixture of the two formulas:
5. a disperse red dye composition according to claim 1 wherein: the disperse red dye composition is composed of a component A, a component B and an auxiliary agent, wherein:
component A is selected from the group consisting of formula (I-1) or (I-2) or (I-3) or combinations thereof,
component B is selected from formula (II-1) or (II-2) or a combination thereof,
based on the component A and the component B, the mass percentage of the component A is 10-45%, the mass percentage of the component B is 10-45%, and the balance is an auxiliary agent.
6. A disperse red dye composition according to claim 5 wherein: the disperse red dye composition is composed of a component A, a component B and an auxiliary agent, wherein:
the component A is shown as a formula (I-1);
the component B is a formula (II-1);
based on the component A and the component B, the mass percentage of the component A is 10-45%, the mass percentage of the component B is 10-45%, and the balance is an auxiliary agent.
7. The disperse red dye composition according to claim 1, wherein the auxiliary agent is selected from one or a combination of two or more of the following: naphthalene sulfonic acid formaldehyde condensate, lignosulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate and benzyl naphthalene sulfonic acid formaldehyde condensate.
8. Use of the disperse red dye composition according to claim 1 for dyeing polyester and polyester blended fabrics.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811493105.XA CN109486238B (en) | 2018-12-10 | 2018-12-10 | Disperse red dye composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811493105.XA CN109486238B (en) | 2018-12-10 | 2018-12-10 | Disperse red dye composition |
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| Publication Number | Publication Date |
|---|---|
| CN109486238A CN109486238A (en) | 2019-03-19 |
| CN109486238B true CN109486238B (en) | 2020-10-27 |
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|---|---|---|---|
| CN201811493105.XA Active CN109486238B (en) | 2018-12-10 | 2018-12-10 | Disperse red dye composition |
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| CN111518414B (en) * | 2020-04-29 | 2021-07-16 | 约克夏(浙江)染化有限公司 | Red disperse dye composition, red disperse dye and preparation method and application thereof |
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| JPH09176509A (en) * | 1995-12-25 | 1997-07-08 | Sumitomo Chem Co Ltd | Colored composition high in light resistance and coloring of hydrophobic material using the same |
| JPH11158402A (en) * | 1997-11-28 | 1999-06-15 | Sumitomo Chem Co Ltd | Disperse dye composition and method for coloring hydrophobic material therewith |
| CN108395732B (en) * | 2018-04-09 | 2019-11-08 | 九江富达实业有限公司 | A kind of black disperse dye composition and black disperse dye |
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