CN114773876A - Disperse red dye composition and product thereof - Google Patents
Disperse red dye composition and product thereof Download PDFInfo
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- CN114773876A CN114773876A CN202210543228.XA CN202210543228A CN114773876A CN 114773876 A CN114773876 A CN 114773876A CN 202210543228 A CN202210543228 A CN 202210543228A CN 114773876 A CN114773876 A CN 114773876A
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- disperse red
- red dye
- dye composition
- following formulas
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- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 239000001044 red dye Substances 0.000 title claims abstract description 37
- 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 36
- 238000004043 dyeing Methods 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000012752 auxiliary agent Substances 0.000 claims description 11
- 239000002270 dispersing agent Substances 0.000 claims description 9
- 239000004744 fabric Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 239000000986 disperse dye Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000013329 compounding Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- -1 phenyl Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 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 8
- 239000000975 dye Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000007639 printing Methods 0.000 description 5
- 239000004576 sand Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 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 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- QLRDACXDRLGLOC-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 QLRDACXDRLGLOC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ZSPPPAFDNHYXNW-UHFFFAOYSA-N 3-[n-ethyl-4-[(4-nitrophenyl)diazenyl]anilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 ZSPPPAFDNHYXNW-UHFFFAOYSA-N 0.000 description 1
- PWUVCFDFTBWAFJ-UHFFFAOYSA-N 3-[n-ethyl-4-[(6-nitro-1,3-benzothiazol-2-yl)diazenyl]anilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=NC2=CC=C([N+]([O-])=O)C=C2S1 PWUVCFDFTBWAFJ-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010017 direct printing 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
- 238000000227 grinding Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000000080 wetting agent 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention provides an environment-friendly disperse red dye composition, which comprises a component A, a component B, a component C and a component D, 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), and the component D is selected from at least one of the following formulas (IV), so that when the composition is applied to dyeing of hydrophobic fiber materials, the composition has good promotion, level dyeing property, compatibility, washing fastness, rubbing fastness and perspiration fastnessExcellent fastness and the like.
Description
(I) the technical field
The invention relates to a disperse red dye composition, in particular to an environment-friendly disperse red dye composition suitable for printing and dyeing hydrophobic fiber materials and a product thereof.
(II) background of the invention
Along with the improvement of society and living standard of people, people pay more and more attention to the environment and self health condition, higher requirements are put forward on the economy and ecological environment protection of textile chemicals, for the dye industry, the development of pollution-free dyes, dyes with high color development strength and dyes with high fastness is particularly important for saving the dye consumption and reducing the waste water discharge, the disperse red dyes are a kind of widely applied color types, namely, the disperse red dyes can be applied in a single color and can also be used for the compound synergy of blue and black, and the red dyes with excellent color fastness on the market are very limited.
Disclosure of the invention
In order to solve the problems, the invention provides an environment-friendly disperse red dye composition which has the characteristics of good promotion, level dyeing property, compatibility, washing fastness, rubbing fastness, 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 red dye composition comprises a component A, a component B, a component C and a component D, 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 component D is selected from at least one of the following formulas (IV), based on the component A, the component B, the component C and the component D, the mass percent of the component A is 5-85%, the mass percent of the component B is 5-85%, the mass percent of the component C is 5-85%, and the mass percent of the component D is 1-50%:
in the formula (I):
R1is hydrogen or-NHCOR11Wherein R is11Is C1～C4An alkyl group;
R2、R3each independently is C1～C4Alkyl or by-CN, -OCOR12-OH substituted C1～C4Alkyl radical, wherein R12Is C1～C4An alkyl group;
in formula (II):
R4is hydrogen or-NHCOR13Wherein R is13Is C1～C4An alkyl group;
R5、R6each independently is C1～C4Alkyl or by-CN, -OCOR14、-COOR15Substituted C1～C4Alkyl radical, wherein R14、R15Each independently is C1～C4An alkyl group;
in the formula (III):
R7is C1～C4An alkyl group;
R8、R9each independently of the other is-OCOR16or-COOR17Substituted C1～C4Alkyl radical, wherein R16、R17Each independently is C1～C4An alkyl group;
in the formula (IV):
x is hydrogen or halogen;
R10is C1～C4Alkyl, C substituted by-CN or phenyl1～C4An alkyl group.
In the present invention, said C1～C4The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.
Further, the component A is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any ratio:
further, the component B is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any ratio:
further, the component C is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any ratio:
further, the component D is preferably selected from one of the following formulas or a mixture of two or more thereof in any ratio:
preferably, the disperse red dye composition consists of a component A, a component B, a component C and a component D, wherein based on the component A, the component B, the component C and the component D, the mass percentage of the component A is 20-70%, the mass percentage of the component B is 20-70%, the mass percentage of the component C is 10-50%, and the mass percentage of the component D is 1-40%.
Still further, the disperse red dye composition of the present invention preferably consists of component a, component B, component C and component D, wherein:
the component A is selected from at least one of formulas (I-1) to (I-4);
the component B is selected from at least one of formulas (II-1) to (II-4);
component C is at least one selected from the formulas (III-1) and (III-2);
the component D is selected from at least one of formulas (IV-1) to (IV-4);
based on the component A, the component B, the component C and the component D, the mass percentage of the component A is 20-70%, the mass percentage of the component B is 20-70%, the mass percentage of the component C is 10-50%, and the mass percentage of the component D is 1-40%.
The disperse red dye composition can also further comprise an orange or red toning component which does not exceed 20 percent of the total weight of the components A to D, such as C.I. disperse orange 25, C.I. disperse orange 31, C.I. disperse red 145 and the like.
The disperse red dye composition can be directly sold as a commodity, or can be sold as a commodity after being added with a conventional auxiliary agent or applied to coloring textile materials. Therefore, the invention also provides a disperse red dye product which mainly comprises the disperse 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 red dye product consists of the disperse 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 of the following or a mixture of two or more of the following in any proportion: 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), anhydrous sodium sulfate (sodium sulfate), and the like.
The preparation method of the disperse red dye product 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, water or other wetting agents; alternatively, each of the dye monomer compounds may be subjected to a pulverization treatment in the presence of an auxiliary agent and water by a pulverizer such as a sand mill or a grinder and then mixed in a ratio. The disperse red dye product of the present invention is liquid after being ground by a sand mill or a grinder, and may be powder or granule 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) to (IV) can be conveniently synthesized in a manner known to those skilled in the art, and can be prepared by a method described in patents CN106752081A, US3956270A, CN108047751A and CN106800798A or a similar method, or by a commercially available method.
The dye product 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 a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be directly used for printing. Wherein, the common dip dyeing method comprises the following steps: 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 as follows: 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.
When the disperse red dye composition and the dye product provided by the invention are applied to dyeing of hydrophobic fiber materials, the disperse red dye composition and the dye product have the characteristics of good promotion, leveling property, compatibility, excellent fastness to washing, friction resistance, excellent fastness to perspiration and the like, and can meet the requirements of the Oeko-Tex standard 100.
(IV) detailed description of the invention
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto.
Example 1:
35 g of component A of the compound of the formula (I-1), 35 g of component B of the compound of the formula (II-1), 25 g of component C of the compound of the formula (III-1), 5 g of component D of the compound of the formula (IV-1) and 250 g of 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 performance for polyester fabrics.
Example 2
30 g of component A of a compound shown in formula (I-1), 30 g of component B of a compound shown in formula (II-1), 25 g of component C of the compound shown in formula (III-1), 5 g of component D of the compound shown in formula (IV-1), 10 g of formula (V) and 250 g of dispersing agent MF are mixed with 850 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 performance for polyester fabrics.
Examples 3 to 30:
according to the method described in example 1, except that the components A-D in Table 1 are adopted in structure and weight, 250 g of auxiliary agent (200 g of dispersant MF and 50 g of sodium lignosulfonate) is added, 800 g of water is added to be mixed to prepare slurry, and the slurry is ground, dispersed and dried to prepare the finished product, and the dye can provide red tones with excellent fastness performance for polyester fabrics:
TABLE 1
Dyeing example:
the disperse dyes prepared in the above examples 1-30 are respectively selected, and the color fastness to washing, perspiration and rubbing is respectively tested according to the standards ISO 105-C10, ISO 105-E04 and ISO105-X12, and the results are shown in the following table 3:
TABLE 3
In conclusion, the disperse red dye composition has good fastness to washing, sweat stain and rubbing, and can meet the printing and dyeing requirements of fabrics with high fastness.
Claims (10)
1. A disperse red dye composition comprises a component A, a component B, a component C and a component D, 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 component D is selected from at least one of the following formulas (IV), based on the component A, the component B, the component C and the component D, the mass percent of the component A is 5-85%, the mass percent of the component B is 5-85%, the mass percent of the component C is 5-85%, and the mass percent of the component D is 1-50%:
in the formula (I):
R1is hydrogen or-NHCOR11Wherein R is11Is C1～C4An alkyl group; r is2、R3Each independently is C1～C4Alkyl or by-CN, -OCOR12-OH substituted C1～C4Alkyl radical, wherein R12Is C1～C4An alkyl group;
in formula (II):
R4is hydrogen or-NHCOR13Wherein R is13Is C1～C4An alkyl group; r5、R6Each independently is C1～C4Alkyl or by-CN, -OCOR14、-COOR15Substituted C1～C4Alkyl radical, wherein R14、R15Each independently is C1～C4An alkyl group;
in the formula (III):
R7is C1～C4An alkyl group; r is8、R9Each independently is-OCOR16or-COOR17Substituted C1～C4Alkyl radical, wherein R16、R17Each independently is C1～C4An alkyl group;
in the formula (IV):
x is hydrogen or halogen; r10Is C1～C4Alkyl, C substituted by-CN or phenyl1～C4An alkyl group.
2. The disperse red dye composition according to claim 1, wherein C is1～C4Alkyl is methyl or ethyl.
3. The disperse red dye composition according to claim 1, wherein the component A is selected from one of the following formulas or a mixture of two or more thereof in any ratio:
4. the disperse red dye composition according to claim 1 wherein the component B is selected from one of the following formulas or a mixture of two or more thereof in any ratio:
5. the disperse red dye composition according to claim 1 wherein the component C is selected from one of the following formulas or a mixture of two or more thereof in any ratio:
6. the disperse red dye composition according to claim 1 wherein the component D is selected from one of the following formulas or a mixture of two or more thereof in any ratio:
7. a disperse red dye composition according to claim 1, consisting of component A, component B, component C and component D.
8. A disperse red dye composition according to claim 7 wherein:
the component A is selected from at least one of formulas (I-1) to (I-4);
the component B is at least one selected from formulas (II-1) to (II-4);
the component C is at least one selected from the formulas (III-1) and (III-2);
the component D is at least one selected from formulas (IV-1) to (IV-4).
9. A disperse red dye product comprises an auxiliary agent and the disperse red dye composition as defined in claim 1, wherein the weight ratio of the auxiliary agent to the disperse red dye composition is 0.2-5: 1, and the auxiliary agent is a dispersing agent, a dispersing agent or other surfactants commonly used in the compounding of disperse dyes.
10. Use of the disperse red dye composition according to claim 1 or the disperse red dye product according to claim 9 for dyeing polyester and polyester blended fabrics.
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