JP2001164143A - Disperse dye composition and method of dyeing hydrophobic fiber using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain products dyed in dark blue or black which excel in a variety of fastness such as fastness to light, fastness to sublimation, and fastness to water after post-processing treatment not only in normal polyester fibers but also in superfine polyester fibers. SOLUTION: Disperse dye compositions comprise dyes represented by formulae (1) and (2) (wherein X1 is a hydrogen atom or a nitro group; R1 is a hydrogen atom, a methyl group, an ethyl group, a propyl group or an allyl group; X2 is a chlorine atom or a bromine atom; Y1 is a hydrogen atom, a methoxy group, an ethoxy group or a methoxyethoxy group; R2 is a methyl group or an ethyl group; R3 is a methyl group, an ethyl group, a propyl group or an ally group).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a dye composition and a dyeing method. More specifically, the present invention has a specific structure 2
The present invention relates to a disperse dye composition containing three or three kinds of disperse dyes and a method for dyeing hydrophobic fibers using the same.

[0002]

2. Description of the Related Art Hydrophobic fibers, for example, polyester fibers are indispensable as materials for clothing due to their excellent fiber properties. Recently, in these hydrophobic fibers, in order to improve the texture of the fibers, the development of differentiated products such as ultra-fine fibers (called micro-fibers) having extremely thin fibers has been actively conducted. Have been done.
Disperse dyes are usually used for dyeing hydrophobic fibers such as polyester fibers in dark blue or black. However, since it is difficult to obtain black with a single dye, a compound of a plurality of dyes (eg, yellow, red) is used. And a blue dye). However, polyester fibers, especially microfibers, are gaining market acceptance due to their excellent texture.However, the surface area per unit weight is several times higher than that of ordinary polyester fibers. Light fastness is inferior due to the effect of total reflection, and it is difficult to obtain dyed products with deep color tone. Also, since a large amount of dye is used, various fastnesses (sublimation fastness) and after post-processing At present, it is difficult to obtain a combination having no defect in the fastness of water (such as water fastness). In a hydrophobic fiber product called a microfiber, a disperse dye composition for obtaining a deep dark blue or black dyed product has already been disclosed as a dyeing method by blending several dyes. However, in these conventional dye compositions and dyeing methods, polyester fibers, especially hydrophobic fibers composed of ultrafine fibers, dyeing properties, especially light fastness, sublimation fastness, water fastness after post-processing, etc. It has not yet been possible to give a dark blue or black dyeing which is satisfactory in its fastness.

[0003]

Problems to be Solved by the Invention Navy blue or black, which is excellent in light fastness, sublimation fastness, water fastness after post-processing, etc. among hydrophobic fibers represented by polyester fiber ultrafine fiber products. It is desired to develop a dye composition that gives a dyed product.

[0004]

Means for Solving the Problems The inventor of the present invention has made intensive studies to solve the above-mentioned problems, and as a result, dyeing is carried out by using a composition containing a disperse dye represented by a specific structure. The inventors have found that the above-mentioned problems can be solved, and have completed the present invention.

That is, the present invention provides (1) a disperse dye composition comprising a dye represented by the following formulas (1) and (2):

[0006]

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(In the formula (1), X ₁ represents a hydrogen atom or a nitro group, and R ₁ represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, or an allyl group.)

[0008]

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(In the formula (2), X ₂ represents a chlorine atom or a bromine atom, Y ₁ represents a hydrogen atom, a methoxy group, an ethoxy group or a methoxyethoxy group, R ₂ represents a methyl group or an ethyl group, R ₃ represents a methyl group, an ethyl group, a propyl group, or an allyl group.) (2) Dyes represented by the formulas (1) and (2) described in the above (1) and a dye represented by the following formula (3). Dye composition characterized by containing a dye to be prepared

[0010]

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(In the formula (3), X ₃ represents a chlorine atom or a bromine atom, Y ₂ represents a hydrogen atom, a methoxy group, an ethoxy group or a methoxyethoxy group, and R ₄ represents a methyl group or an ethyl group, respectively. (3) The dye represented by the formula (1) described in the above item (1) is
0 to 90% by weight of the dye represented by the formula (2)
(4) a dye represented by the formula (1) described in (1) above,
0 to 90% by weight, 5 to 35% by weight of the dye represented by the formula (2), 5 to 35% by weight of the dye represented by the formula (3) according to claim 2.
Disperse dye composition characterized by containing 35% by weight (5) Hydrophobic fiber characterized by using the disperse dye composition described in the above (1), (2), (3) or (4) About the staining method.

[0012]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. In the present invention, by mixing the dye of the formula (1) with the dye of the formula (2) and, if desired, the dye of the formula (3), the polyester fiber, especially the hydrophobic fiber such as the ultrafine fiber, is used. It gives a dark blue or black dyed article having excellent fastnesses such as light fastness, sublimation fastness and water fastness after post-processing.

The proportion of the dye used in preparing the disperse dye composition of the present invention is usually 30 to 90% by weight, preferably 40 to 80% by weight of the dye represented by the formula (1).
It is prepared by blending the dye represented by the formula (2) at a ratio of 10 to 70% by weight, preferably 20 to 60% by weight. When the disperse dye composition of the present invention contains the dye represented by the formula (3), the dye represented by the formula (1) is usually used in an amount of 3%.
0 to 90% by weight, preferably 40 to 80% by weight, and 5 to 35% by weight, preferably 1 to 35% by weight of the dye represented by the formula (2).
It is prepared by mixing 0 to 30% by weight of the dye represented by the formula (3) in a ratio of 5 to 35% by weight, preferably 10 to 30% by weight. In preparing the disperse dye composition of the present invention, a dye other than the above may be blended, for example, for adjusting the hue, as long as the gist of the present invention is not impaired.

Specific examples of the dye represented by the formula (1) used in the present invention include the following formulas (4) and (5)

[0015]

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And mixtures thereof. Specific examples of the dye represented by the formula (2) include the following formulas (6), (7), and (8).

[0017]

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And mixtures thereof. As specific examples of the dye represented by the formula (3), the following formula (9)

[0019]

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A mixture of this with another dye represented by the formula (3) can also be used.

Next, the dyes represented by the formulas (1), (2) and (3) used in preparing the dye composition of the present invention are all known or can be prepared by known methods. It can be easily obtained in accordance with it. For example, dyes represented by the formula (1) are described in JP-A-49-47680 and JP-A-63-6
3595, the dye represented by formula (2) is
2035, JP-B-57-49583, and the dyes represented by the formula (3) can be easily produced by using the method described in JP-A-57-49583.

The disperse dye composition of the present invention is obtained by mixing the respective powders of the dyes represented by the formulas (1), (2) and (3) and then forming a fine-particle sand grinder in the presence of a dispersant and water. A fine particle treatment (usually about 0.2 to 1.0 μm) is performed using a device for fine particle formation such as a mill or a crusher to obtain a paste of the dye composition of the present invention. If desired, the paste product can be dried by a spray drying method or the like to obtain a dried product of the dye composition of the present invention. Here, as the dispersant, formalin condensate of naphthalenesulfonic acid, sodium ligninsulfonate and the like can be used. Water used in the micronization treatment is used at a ratio of about 1.5 parts by weight with respect to 1 of solid content (dye powder + dispersant).
In the dye composition of the present invention, a dust inhibitor and a granulating aid can be used as necessary. Further, after each of these raw dye powders is subjected to the above-mentioned fine particle dispersing (dispersing) treatment, they may be mixed in the above-described ratio. In the latter case, a dye which has been individually made fine (dispersed) may be added to the dye bath to form the same composition as the dye composition of the present invention in the dye bath.

Next, the dyeing method of the present invention will be described.
As long as the dyeing method of the present invention uses the dye composition of the present invention,
No particular limitation is imposed on the dyeing method, and the dyeing method under ordinary high temperature and high pressure, the carrier dyeing method, the printing method, and the
A mosol method, a pad steam method, or the like can be employed. Dyeing method under high temperature and high pressure In the dyeing method, the dyeing temperature is 100 ° C to 14 ° C.
It is advantageous to dye at 0 ° C., preferably at 110 ° C. to 130 ° C. Dyeing can also be carried out at a relatively high temperature, for example, in the boiling state of water, in the presence of a carrier such as O-phenylphenol or chlorobenzene. Alternatively, the dispersion of the dye composition of the present invention is put on a cloth, and
A so-called server for drying at 30 ° C. for 30 seconds to 1 minute.
Dyeing by the mozole method is also possible. On the other hand, the dye composition of the present invention and a natural paste (eg, sodium alginate, starch, casein, gelatin, etc.), a synthetic paste (eg, polyvinyl alcohol, polyvinyl acetate, etc.), a reducing inhibitor, p
The printing paste may be adjusted together with an H adjuster, a deep dyeing agent, and the like, and dyeing may be performed by a printing method according to a conventional method. It is also possible to dye from a dye bath mainly containing an organic solvent such as trichlorethylene or perchloroethylene. (Solvent dyeing)
In these dyeing methods, commonly used dyeing auxiliaries such as leveling agents and dispersants are appropriately used as needed. The amount used when dyeing with the disperse dye composition of the present invention is arbitrary, but in a preferred embodiment, for example, in the case of 3 denier fiber, 4 to 10% o. w. f (based on fiber weight).

The fibers to which the dyeing method of the present invention is applied include hydrophobic fibers. Specific examples of applicable hydrophobic fibers include polyester fibers, particularly fibers constituting a product called microfiber (microfiber), and other synthetic fibers other than polyester fiber. The thickness of the hydrophobic fiber is usually 1.
When dyeing hydrophobic fibers of about 0 to 5.0 d (denier) and further microfibers (fibers of usually 1.0 d or less are referred to as microfibers), favorable dyeing results can be obtained. The preferred fiber thickness of the microfiber is 0.01 to 1.0 d.

Hereinafter, in order to show that the disperse dye composition of the present invention is extremely excellent in improving various fastnesses,
A mixture of the formulas (1) and (2) and the formulas (1) and (2)
Comparison of the fastness of a mixture of formula (3) and a disperse dye composition for comparison with a dyed dark blue or black dyeing a normal polyester fiber (3 denier) and a fine polyester fiber (0.3 denier). And the results are shown in Tables 1 and 2.

Table 1 Normal polyester fiber: Comparison of fastness at 3 deniers (Note 4) Light fastness (Note 1) Sublimation (Note 2) Water test (Note 3) Comparative example 1 4-5 3-4 3-4 Comparative example 25 4 1-2 Comparative example 3 5 4 2-3 Example 1 6-7 44 Example 2 6-7 44 Example 3 6-7 4 4 Example 4 5-6 4 4 Example 5 6 −7 4 4 Example 6 6−7 4 4

(Note 1) Light fastness test: JIS L0
842 (carbon arc 40 80 hours irradiation), judged by gray scale for discoloration and fading (Note 2) Sublimation fastness test: JIS L0879 (18)
(0 ° C, 30 seconds) Judge polyester contamination by gray scale for contamination (Note 3) Water fastness test: JIS L0846 (37
(C, 4 hours) Judgment of silk contamination by gray scale for contamination The criteria for the above (Note 1) to (Note 3) are as follows. Judgment criteria Display symbol 5: No difference 4: Slight difference 3: Slight difference 2: Slight difference 1: Slight difference

(Note 4) 8 parts (8.0% owf (weight ratio to fiber)) of the disperse dye compositions obtained in Examples 1 to 6 and Comparative Examples 1 to 3 (mixed dyes) 30 parts of the bulk powder were subjected to microparticulation treatment using 70 parts of a formalin condensate of naphthalenesulfonic acid and dried by a vacuum drying method using a sand grinder, and water adjusted to pH 4.5 was added thereto.
000 parts of a dyeing bath was prepared (bath ratio: 1:30), and 10 parts of a polyester fiber fabric (3 denier) was immersed in the dye bath.
After dyeing at 0 ° C. for 60 minutes, the dyed product was treated with 6 parts of 45% caustic soda, 6 parts of hydrosulfite, and Sunmol RC-
700 parts (anionic surfactant manufactured by Kao Corporation) was subjected to reduction washing at 80 ° C. for 10 minutes in a bath prepared by adding water to 3,000 parts by adding water, washing with water, drying and heat setting at 180 ° C. for 30 seconds. To obtain a dyed product.

Table 2 Ultrafine polyester fiber: Comparison of fastness at 0.3 denier (Note 5) Lightfastness (Note 1) Sublimation (Note 2) Water test (Note 3) Comparative Example 1 3-4 3 3 Comparative Example 2 4 3-4 1 Comparative Example 3 4 3-4 2 Example 1 5-6 3-4 3-4 Example 2 5-6 3-4 3-4 Example 3 5-6 3-4 3-4 Example 4 5 3-4 3-4 Example 5 5-6 3-4 3-4 Example 6 5-6 3-4 3-4

(Note 5) 24 parts (24.0% owf) of the disperse dye compositions obtained in Examples 1 to 6 and Comparative Examples 1 to 3
(Weight ratio to fiber)) (30 parts of the mixed dye base powder and 70 parts of a formalin condensate of naphthalenesulfonic acid were subjected to micronization treatment using a sand grinder and dried by a vacuum drying method) to pH 4.5. A dye bath was prepared by adding water adjusted to the above to 3000 parts (bath ratio: 1:30).
After immersing 10 parts of ultrafine polyester fiber fabric (0.3 denier) and dyeing at 130 ° C. for 60 minutes,
% Caustic soda, 6 parts of hydrosulfite, and 3 parts of sunmole RC-700, to which 3 parts of water was added to make a total amount of 3000 parts.
After drying and heat setting at 180 ° C. for 30 seconds, a dyed product was obtained.

As is clear from the results of Tables 1 and 2, the disperse dye compositions containing the dyes of the formulas (1) and (2) and the dyes of the formulas (1), (2) and (3) The disperse dye composition containing is a normal polyester fiber (3 denier)
The light fastness, the sublimation fastness, and the water fastness of the ultrafine polyester fiber (0.3 denier) are all at a good level in the fastness items. Conventionally, a dye composition having an excellent water test had poor light fastness, and a dye composition having an excellent light resistance test and sublimation test had an inferior water test. This is also confirmed from the fact that the dye compositions of Comparative Examples 1 to 3 have weaknesses in any of the fastness items. As shown in Tables 1 and 2, the disperse dye composition of the present invention is excellent in any of the light resistance test, the sublimation test, and the water test, and shows that the fastness is excellent overall.

[0032]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. In the examples, "parts" and "%" mean parts by weight and% by weight, respectively.

Example 1 30 parts of a mixture of 24 parts of the bulk of the dye of the formula (4) and 6 parts of the bulk of the dye of the formula (6) were treated with 70 parts of a formalin condensate of naphthalenesulfonic acid into fine particles, and then dried. A dye composition of the present invention was obtained. Add 8 parts (in the case of 3 denier) or 24 parts (in the case of 0.3 denier) of the dye composition to pH
Pure water adjusted to 4.5 was added to prepare a dyeing bath of 3000 parts, and a polyester fiber woven fabric (using 3 denier yarn, manufactured by Toyobo) and an ultrafine polyester fiber woven fabric (using 0.3 denier yarn, manufactured by Toyobo) ) 100 parts soaked at 130 ° C
After dyeing for 6 minutes, the dyed product is treated with 45% caustic soda 6
Parts, hydrosulfite 6 parts, Sunmole RC-70
0 In a bath, add 3 parts of water to make a total of 3000 parts.
The resultant was subjected to reduction washing at 10 ° C. for 10 minutes, washed with water and dried to obtain a dyed product. The lightfastness, sublimation, water and other fastnesses of the dyed product were good for both the fabrics using 3 denier yarn and the fabric using 0.3 denier yarn.

Example 2 30 parts of a mixture of 24 parts of the bulk of the dye of the formula (4), 3 parts of the bulk of the dye of the formula (6) and 3 parts of the bulk of the dye of the formula (9) were mixed with 30 parts of formalin of naphthalenesulfonic acid. After the fine particles were treated together with 70 parts of the condensate, they were dried to obtain the dye composition of the present invention. 8 parts (in the case of 3 deniers) or 24 parts (0.
3 deniers), pure water adjusted to pH 4.5 was added to prepare a dyeing bath of 3000 parts, and a polyester fiber woven fabric (using 3 denier yarn, manufactured by Toyobo Co., Ltd.) and an ultrafine polyester fiber woven fabric (0.3 Using denier yarn, manufactured by Toyobo)
100 parts were immersed and dyed at 130 ° C. for 6 minutes, and then the dyed product was treated with 6 parts of 45% caustic soda and hydrosulfite 6
Part, Sunmole RC-700 3 parts, add water to 3 parts
The resultant was subjected to reduction washing at 80 ° C. for 10 minutes in a bath of 000 parts, washed with water and dried to obtain a dyed product. The lightfastness, sublimation, water and other fastnesses of the dyed fabric are 3 denier yarn woven fabric, 0.3
The fabrics using denier yarn were also good.

Example 3 21.6 parts of the dye base of the formula (4), 2.7 parts of the dye base of the formula (7), 2.7 parts of the dye base of the formula (9) and the following formula (1)
30 parts obtained by mixing 3 parts of the dye bulk powder of 0) with 70 parts of a formalin condensate of naphthalenesulfonic acid were subjected to fine-particle treatment, followed by drying to obtain a dye composition of the present invention. To 8 parts (in the case of 3 deniers) or 24 parts (in the case of 0.3 deniers) of this dye composition, pure water adjusted to pH 4.5 was added to prepare 3000 parts of a dyeing bath. Using 3 denier yarn, manufactured by Toyobo) and extra-fine polyester fiber fabric (using 0.3 denier yarn, manufactured by Toyobo) 10
0 parts were immersed and dyed at 130 ° C. for 6 minutes, and the dyed product was treated with 6 parts of 45% caustic soda, 6 parts of hydrosulfite,
Add water to 3 parts of Sun Mall RC-700 for a total volume of 300
The resultant was subjected to reduction washing at 80 ° C. for 10 minutes in a bath of 0 parts, washed with water and dried to obtain a dyed product. The lightfastness, sublimation, water and other fastnesses of the dyed product were good for both the fabrics using 3 denier yarn and the fabric using 0.3 denier yarn.

[0036]

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Example 4 Formalin condensation of naphthalenesulfonic acid was conducted by mixing 30 parts of a mixture of 24 parts of the bulk powder of the formula (5), 3 parts of the bulk powder of the formula (6) and 3 parts of the bulk powder of the formula (9). The mixture was subjected to a fine particle treatment together with 70 parts of the product, and then dried to obtain a dye composition of the present invention. 8 parts (for 3 deniers) or 24 parts (0.3 parts) of this dye composition
(In the case of denier), pure water adjusted to pH 4.5 was added to prepare a dyeing bath of 3000 parts, and a polyester fiber woven fabric (using 3 denier yarn, manufactured by Toyobo Co., Ltd.) and an ultrafine polyester fiber woven fabric (0.3 denier) Using yarn, manufactured by Toyobo) 1
After immersion in 00 parts and dyeing at 130 ° C. for 6 minutes, the dyed product was treated with 6 parts of 45% caustic soda and hydrosulfite 6
Parts, Sun Mall RC-7003 parts, water is added, and the total amount is 30
Performing reduction washing at 80 ° C. for 10 minutes in a bath containing 00 parts,
After washing with water and drying, a dyed product was obtained. The lightfastness, sublimation, water and other fastnesses of the dyed product were good for both the fabrics using 3 denier yarn and the fabric using 0.3 denier yarn.

Example 5 Formalin condensation of naphthalenesulfonic acid was carried out by mixing 30 parts of a mixture of 24 parts of the bulk powder of the formula (4), 3 parts of the bulk powder of the formula (7) and 3 parts of the bulk powder of the formula (9). The mixture was subjected to a fine particle treatment together with 70 parts of the product, and then dried to obtain a dye composition of the present invention. 8 parts (for 3 deniers) or 24 parts (0.3 parts) of this dye composition
(In the case of denier), pure water adjusted to pH 4.5 was added to prepare a dyeing bath of 3000 parts, and a polyester fiber woven fabric (using 3 denier yarn, manufactured by Toyobo Co., Ltd.) and an ultrafine polyester fiber woven fabric (0.3 denier) Using yarn, manufactured by Toyobo) 1
After immersion in 00 parts and dyeing at 130 ° C. for 6 minutes, the dyed product was treated with 6 parts of 45% caustic soda and hydrosulfite 6
Parts, Sun Mall RC-7003 parts, water is added, and the total amount is 30
Performing reduction washing at 80 ° C. for 10 minutes in a bath containing 00 parts,
After washing with water and drying, a dyed product was obtained. The lightfastness, sublimation, water and other fastnesses of the dyed product were good for both the fabrics using 3 denier yarn and the fabric using 0.3 denier yarn.

Example 6 Formalin condensation of naphthalenesulfonic acid was carried out by mixing 30 parts of a mixture of 24 parts of the bulk powder of the formula (4), 3 parts of the bulk powder of the formula (8) and 3 parts of the bulk powder of the formula (9). The mixture was subjected to a fine particle treatment together with 70 parts of the product, and then dried to obtain a dye composition of the present invention. 8 parts (for 3 deniers) or 24 parts (0.3 parts) of this dye composition
(In the case of denier), pure water adjusted to pH 4.5 was added to prepare a dyeing bath of 3000 parts, and a polyester fiber woven fabric (using 3 denier yarn, manufactured by Toyobo Co., Ltd.) and an ultrafine polyester fiber woven fabric (0.3 denier) Using yarn, manufactured by Toyobo) 1
After immersion in 00 parts and dyeing at 130 ° C. for 6 minutes, the dyed product was treated with 6 parts of 45% caustic soda and hydrosulfite 6
Parts, Sun Mall RC-7003 parts, water is added, and the total amount is 30
Performing reduction washing at 80 ° C. for 10 minutes in a bath containing 00 parts,
After washing with water and drying, a dyed product was obtained. The lightfastness, sublimation, water and other fastnesses of the dyed product were good for both the fabrics using 3 denier yarn and the fabric using 0.3 denier yarn.

Comparative Examples 1 to 3 Comparative disperse dye compositions having the compositions shown in Table 3 were prepared in the same manner as in the Examples using the raw dye powders of the following formulas (11), (12) and (13). Then, the polyester fiber woven fabric (3 denier) and the ultrafine polyester fiber woven fabric (0.3 denier) were dyed in the same manner as in Example 1 to obtain a dyed product, and various fastnesses were measured.

Table 3: Comparative Examples 1 to 3 (In the table, the used amount of the bulk dye is expressed in parts by weight.) Formula (11) Formula (12) Formula (13) Comparative Example 1 50 50-Comparative Example 2- 40 60 Comparative Example 3 25 50 25

[0042]

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[0043]

According to the dyeing method using the dye composition of the present invention, not only ordinary polyester fibers but also ultrafine polyester fibers can be dyed in a dark blue or black color having good fastness and free from defects. Can be.

Claims (5)

[Claims] 1. A disperse dye composition comprising the dyes represented by the following formulas (1) and (2). Embedded image (In the formula (1), X ₁ represents a hydrogen atom or a nitro group, and R ₁ represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, or an allyl group.) (In the formula (2), X ₂ represents a chlorine atom or a bromine atom, Y ₁ represents a hydrogen atom, a methoxy group, an ethoxy group or a methoxyethoxy group, R ₂ represents a methyl group or an ethyl group, and R ₃ represents Represents a methyl group, an ethyl group, a propyl group, and an allyl group, respectively.) 2. A disperse dye composition comprising the dyes represented by the formulas (1) and (2) according to claim 1 and the dyes represented by the following formula (3). Embedded image (In the formula (3), X ₃ represents a chlorine atom or a bromine atom, Y ₂
Represents a hydrogen atom, a methoxy group, an ethoxy group or a methoxyethoxy group, and R ₄ represents a methyl group or an ethyl group, respectively. ) 3. The dye of the formula (1) according to claim 1 is contained in an amount of 30 to 90% by weight, and the dye of the formula (2) is added in an amount of 10 to 90% by weight.
A disperse dye composition comprising 70% by weight. 4. A dye represented by the formula (1) according to claim 1 in an amount of 30 to 90% by weight, and a dye represented by the formula (2) in an amount of 5 to 3%.
A disperse dye composition comprising 5% by weight of the dye represented by the formula (3) according to claim 2 and 5 to 35% by weight. 5. A method for dyeing hydrophobic fibers, comprising using the disperse dye composition according to claim 1, 2, 3, or 4.