JP7222565B2 - dye composition - Google Patents

Description

The present invention relates to a dye composition, a method for dyeing fibers, fibers dyed by the dyeing method, and compounds.

Polyolefin resins such as polypropylene resins and polyethylene resins are crystalline thermoplastic resins that are inexpensive, easy to process, have high strength, have high chemical resistance, high abrasion resistance, high bending resistance, light weight, low hygroscopicity, It has excellent properties such as low thermal conductivity and high antistatic properties.

On the other hand, polyolefin-based resins are high-molecular compounds composed of hydrocarbons in both the main chain and side chains, and have low affinity and compatibility with conventional dye compounds, and have functional groups that are effective in chemical reactions. It has been considered extremely difficult to achieve high density and high fastness dyeing for the following reasons.

For this reason, most colored polyolefin resins currently on the market are produced by adding a colored pigment in the production stage of polymer pellets, etc., and then spinning and molding into a desired shape.

In this coloring method, it is necessary to determine the color at the initial stage of the resin product manufacturing process. Also, considering profitability, it is necessary to produce more than a certain amount of one color, and as a result, the freedom of color selection is limited.

Furthermore, when changing the color of a resin product, a process of replacing the colored resin of the previous color remaining in the resin product manufacturing equipment with the colored resin of the next color is required, and a large amount of waste is generated at that time. Problems such as the generation of resin and wasted time and energy arise.

As described in Non-Patent Document 1, polypropylene resin and polyethylene resin are the four major general-purpose synthetic resins along with polyvinyl chloride resin and polystyrene resin, and are used in a wide range of fields.

However, the use of polypropylene resins and polyethylene resins as synthetic fibers is very limited.

The reason for this is that, as mentioned above, it is extremely difficult to dye polypropylene resin fibers and polyethylene resin fibers with high density and high fastness, and the only effective coloring method, the undiluted coloring method using colored pigments, inevitably results in a large single filament fineness. It is also considered that the freedom of color selection is restricted.

In the past, attempts have been made to change the molecular structure of dyes for water-based dyeing of polyolefin resin fibers, and patent documents 1 to 5 propose dyes for dyeing polyolefin resin fibers.

Patent Document 1 describes production examples of red dyes and purple dyes obtained by introducing a phenoxy group having an alkyl group or a cycloalkyl group having 3 to 12 carbon atoms or a cycloalkyl group as a substituent into an anthraquinone dye, and polypropylene resin fibers using them. staining examples are described.

However, with these anthraquinone red dyes or anthraquinone purple dyes, it is difficult to dye polyolefin resin fibers at a high density. Furthermore, regarding the form of the dyes used for dyeing, there is a description that these anthraquinone red dyes are used after dissolving them in an organic solvent such as alcohol or acetone, and it is difficult to say that they are environmentally friendly.

Patent Document 2 discloses production examples of blue dyes obtained by introducing a phenoxy group having an alkyl group having 1 to 9 carbon atoms, a cycloalkyl group or a halogeno group as a substituent into an anthraquinone dye, and polyester fibers using them, Examples of dyeing polyamide fibers and polyolefin resin fibers are described.

However, with these anthraquinone blue dyes, it is difficult to dye polyolefin resin fibers at a high density, and there is no specific description of the dyeing fastness of the obtained dyed products. Furthermore, regarding the form of the dyes used for dyeing, there is a description that these anthraquinone blue dyes are used after being dissolved in an organic solvent such as alcohol or acetone, and it is difficult to say that they are environmentally friendly.

Patent Document 3 describes production examples of blue dyes obtained by introducing a phenoxy group having an alkyl group having 1 to 9 carbon atoms or a halogeno group as a substituent into an anthraquinone dye, and dyeing examples of polyolefin resin fibers using them. is described.

However, with these anthraquinone blue dyes, it is difficult to dye polyolefin resin fibers at a high density, and there is no specific description of the dyeing fastness of the obtained dyed products. Furthermore, regarding the form of the dyes used for dyeing, it is described that these anthraquinone blue dyes are used after being pulverized with a suitable dispersant such as sodium dinaphthylmethanesulfonate, but the specific pulverization method is not specified. Not listed. As another form, there is a description of using after dissolving in an organic solvent such as alcohol or acetone, and it is difficult to say that this is environmentally friendly.

Patent Document 4 describes an example of dyeing a polyolefin resin fiber using a blue dye obtained by introducing an alkylamino group or a cycloalkylamino group at the α-position of an anthraquinone dye.

However, with these anthraquinone blue dyes, it is difficult to dye polyolefin resin fibers at a high density, and there is no specific description of the dyeing fastness of the obtained dyed products.

Patent Document 5 discloses production examples of red dyes obtained by introducing phenoxy groups having two substituents selected from sec-butyl group, sec-pentyl group and tert-pentyl group into anthraquinone dyes, and their use. Examples of dyeing polypropylene resin fibers are described.

However, with these anthraquinone red dyes, it is difficult to dye polyolefin resin fibers at a high density, and there is no specific description of the color fastness of the obtained dyed product. Furthermore, regarding the form of the dye used for dyeing, it is described that these anthraquinone red dyes are used in the form of a paste, but no specific method for producing the dye paste is described. As another form, there is a description of using after dissolving in dimethylformamide, which is an organic solvent, etc., and it is difficult to say that this is environmentally friendly.

Patent Document 6 describes production examples of monoazo dyes having long-chain alkyl groups and dyeing examples of fine denier polyester fibers using them. However, no examples of dyeing polyolefin fibers using them are described. Furthermore, regarding the form of the dye used for dyeing, it is described that these monoazo dyes are used in the form of a paste using a suitable dispersant, but no specific method for producing the dye paste is described. .

Further, in order to improve the dyeability of polyolefin resin fibers, various modifications of polyolefin resin fibers have been studied.

Modification techniques include blending of dyeable resin components such as polyester, copolymerization with vinyl monomers having dyeable groups, and blending of dye accelerators such as metal stearates. It has been known.

Although the dyeability of these modified polyolefin resin fibers has been improved, there is a problem that the strength of the yarn is reduced by the dyeing treatment, resulting in insufficient strength when used for clothes and the like.

When a method for dyeing polypropylene resin fibers and polyethylene resin fibers with high density and high fastness is put into practical use, it will be possible to color uncolored, small single filament fineness, inexpensive regular yarns without restrictions on the number of colors. It is expected to develop new applications in fields where high designability is required, such as clothing and vehicle interior materials, where resin fibers and polyethylene resin fibers have not been applied.

Japanese Patent Publication No. 38-10741 Japanese Patent Publication No. 40-1277 Japanese Patent Publication No. 41-3515 British Patent No. 872,882 U.S. Pat. No. 3,536,735 JP-A-55-152869

Hiroshi Yamamoto, Journal of the Society of Fiber Science and Technology, 61 (2005), 319-321.

Therefore, the present invention provides a dye composition, a method for dyeing fibers, and a method for dyeing fibers, which can dye fibers in various hues at high concentrations and has excellent color fastness such as light resistance, sublimation, and washing. The object is to provide dyed fibers and compounds.

The present invention is a dye composition containing at least one of the compounds represented by the following general formulas (A) to (G) and a nonionic dispersant.

[in formula (A),
X _A is a nitro group,
Y _A represents a halogen atom,
R _A1 , R _A2 and R _A3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms);
R _A4 represents an alkyl group having 1 to 4 carbon atoms. ]

[In the formula (B), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _B1 , R _B2 and R _B3 is a an alkyl group). ]

[In formula (C),
_X and _Y represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, a hydrogen atom and a hydrogen atom; R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms). ]

[In formula (D), X _D and Y _D each independently represent a hydrogen atom, a halogen atom, or a cyano group,
R _D1 represents an alkyl group having 1 to 14 carbon atoms,
R _D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (provided that at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms ). ]

[In formula (E), X _E and Y _E each independently represent a halogen atom, and R _E represents an alkyl group having 4 to 18 carbon atoms. ]

[In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms. ]

[In the formula (G), R _G represents an alkyl group having 7 or 10 to 18 carbon atoms. ]

The present invention also provides a method of dyeing fibers comprising the step of water-based dyeing the fibers using the dye composition of the present invention.

The present invention also provides fibers dyed by the dyeing method of the present invention.

The present invention also provides compounds represented by any one of the following general formulas (A) to (G).

[in formula (A),
X _A is a nitro group,
Y _A represents a halogen atom,
R _A1 , R _A2 and R _A3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms);
R _A4 represents an alkyl group having 1 to 4 carbon atoms. ]

[In the formula (B), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _B1 , R _B2 and R _B3 is a an alkyl group). ]

[In formula (C),
_X and _Y represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, a hydrogen atom and a hydrogen atom;
R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms). ]

[in formula (D),
X _D and Y _D each independently represent a hydrogen atom, a halogen atom, or a cyano group;
R _D1 represents an alkyl group having 1 to 14 carbon atoms,
R _D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (provided that at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms ). ]

[In formula (E), X _E and Y _E each independently represent a halogen atom, and R _E represents an alkyl group having 4 to 18 carbon atoms. ]

[In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms. ]

[In the formula (G), R _G represents an alkyl group having 7 or 10 to 18 carbon atoms. ]

The dye composition of the present invention is capable of dyeing fibers in various hues at a high density, and the dyed products are excellent in color fastness such as light fastness, sublimation and washing.

The inventors of the present invention have found that dyes containing the following specific compounds have improved affinity for fibers and can dye fibers in various hues at high density, thus completing the present invention.

<Compounds of general formulas (A) to (G)>
The compounds of general formulas (A) to (G) contained in the dye of the present invention are as follows.

[in formula (A),
X _A is a nitro group,
Y _A represents a halogen atom,
R _A1 , R _A2 and R _A3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms);
R _A4 represents an alkyl group having 1 to 4 carbon atoms. ]

[In the formula (B), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _B1 , R _B2 and R _B3 is a an alkyl group). ]

[In formula (C),
_X and _Y represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, a hydrogen atom and a hydrogen atom;
R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms). ]

[In formula (D), X _D and Y _D each independently represent a hydrogen atom, a halogen atom, or a cyano group,
R _D1 represents an alkyl group having 1 to 14 carbon atoms,
R _D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (provided that at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms ). ]

[In formula (E), X _E and Y _E each independently represent a halogen atom, and R _E represents an alkyl group having 4 to 18 carbon atoms. ]

[In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms. ]

[In the formula (G), R _G represents an alkyl group having 7 or 10 to 18 carbon atoms. ]

In formula (A), formula (C), formula (D), and formula (E), the halogen atom is a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Atom, bromine atom.

In the above formulas (A) to (D), the alkyl group having 1 to 14 carbon atoms includes, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, n-pentyl group, i-pentyl group, sec-pentyl group, t-pentyl group, 2-methylbutyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 1 A linear or branched alkyl group having 1 to 14 carbon atoms such as -ethyl-1-methylpropyl group can be mentioned. As the alkyl group having 1 to 14 carbon atoms, an alkyl group having 1 to 12 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms is more preferable.

In the above formula (A), the alkyl group having 1 to 4 carbon atoms means, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group. , t-butyl group, and other linear or branched alkyl groups having 1 to 4 carbon atoms. As the alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 2 carbon atoms is preferable, and an alkyl group having 1 carbon atom is more preferable.

In the above formulas (A) to (D) and (F), the alkyl group having 4 to 14 carbon atoms means, for example, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, n- pentyl group, i-pentyl group, sec-pentyl group, t-pentyl group, 2-methylbutyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl linear groups such as 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 1-ethyl-1-methylpropyl groups A straight or branched alkyl group having 4 to 14 carbon atoms can be mentioned. As the alkyl group having 4 to 14 carbon atoms, an alkyl group having 4 to 12 carbon atoms is preferable, and an alkyl group having 4 to 8 carbon atoms is more preferable.

In formula (E), the alkyl group having 4 to 18 carbon atoms includes, for example, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, n-pentyl group, i-pentyl group, sec-pentyl group, t-pentyl group, 2-methylbutyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2 - Linear or branched alkyl groups such as ethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 1-ethyl-1-methylpropyl can be mentioned. As the alkyl group having 4 to 18 carbon atoms, an alkyl group having 4 to 12 carbon atoms is preferable, and an alkyl group having 8 to 12 carbon atoms is more preferable.

In formula (G), the alkyl group having 7 to 18 carbon atoms includes, for example, n-heptyl group, 1-methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 1 -linear or branched alkyl having 7 to 18 carbon atoms such as ethylpentyl group, 2-ethylpentyl group, 1,1-dimethylpentyl group, 2,2-dimethylpentyl group and 3,3-dimethylpentyl group groups can be mentioned. As the alkyl group having 7 to 18 carbon atoms, an alkyl group having 11 to 18 carbon atoms is preferable, and an alkyl group having 15 to 18 carbon atoms is more preferable.

<Compound of general formula (A)>

The compound of general formula (A) is represented by:
X _A is a nitro group,
Y _A represents a halogen atom,
R _A1 , R _A2 and R _A3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms);
R _A4 represents an alkyl group having 1 to 4 carbon atoms.

The compound of formula (A) is a blue dye compound.

In the formula (A),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
Y _A is preferably a bromine atom.

Further, in the formula (A),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
R _A1 , R _A2 and R _A3 are each independently an alkyl group having 4 to 14 carbon atoms, or
R _A1 and R _A2 are each independently an alkyl group having 4 to 14 carbon atoms, and R _A3 is an alkyl group having 1 to 4 carbon atoms, or R _A3 is an alkyl group having 4 to 14 carbon atoms; and R _A1 and R _A2 are each independently preferably an alkyl group having 1 to 4 carbon atoms.

Further, in the formula (A),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
Y _A is a bromine atom;
R _A1 , R _A2 and R _A3 are each independently an alkyl group having 4 to 14 carbon atoms, or
R _A1 and R _A2 are each independently an alkyl group having 4 to 14 carbon atoms, and R _A3 is an alkyl group having 1 to 4 carbon atoms, or R _A3 is an alkyl group having 4 to 14 carbon atoms; and R _A1 and R _A2 are each independently preferably an alkyl group having 1 to 4 carbon atoms.

<Compound of general formula (B)>

The compound of general formula (B) is represented in formula (B) by
R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms. However, at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms.

The compound of formula (B) is a blue or purple dye compound.

In the formula (B),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
R _B1 , R _B2 and R _B3 are each independently an alkyl group having 4 to 14 carbon atoms, or R _B1 and R _B2 are each independently an alkyl group having 4 to 14 carbon atoms, and R _B3 is an alkyl group having 1 to 4 carbon atoms, or R _B3 is an alkyl group having 4 to 14 carbon atoms, and R _B1 and R _B2 are each independently an alkyl group having 1 to 4 carbon atoms is preferred.

<Compound of general formula (C)>

The compound of general formula (C) is represented in formula (C) by
_X and _Y represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, a hydrogen atom and a hydrogen atom;
R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms).

The compound of formula (C) is a red or purple dye compound.

In the formula (C),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
X _C and Y _C represent any combination of a hydrogen atom and a chlorine atom, a bromine atom and a nitro group, a bromine atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, a hydrogen atom and a hydrogen atom. is preferred.

In the formula (C),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
_X and _Y represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, a hydrogen atom and a hydrogen atom;
R _C1 , R _C2 and R _C3 are each independently an alkyl group having 4 to 14 carbon atoms, or
R _C1 and R _C2 are each independently an alkyl group having 4 to 14 carbon atoms, and R _C3 is an alkyl group having 1 to 4 carbon atoms, or R _C3 is an alkyl group having 4 to 14 carbon atoms. and R _C1 and R _C2 are each independently an alkyl group having 1 to 4 carbon atoms.

<Compound of general formula (D)>

In the compound of general formula (D), X _D and Y _D each independently represent a hydrogen atom, a halogen atom, or a cyano group,
R _D1 represents an alkyl group having 1 to 14 carbon atoms,
R _D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (provided that at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms ).

The compound of formula (D) is an orange or red dye compound.

In the formula (D),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
X _D represents a hydrogen atom, a chlorine atom or a bromine atom;
Y _D preferably represents a hydrogen atom, a chlorine atom, a bromine atom, or a cyano group.

Further, in the formula (D), X _D and Y _D each independently represent a hydrogen atom, a halogen atom, or a cyano group,
R _D1 represents an alkyl group having 4 to 14 carbon atoms,
R _D2 preferably represents an alkyl group having 4 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN.

<Compound of general formula (E)>

In the compound of general formula (E), X _E and Y _E each independently represent a halogen atom, and R _E represents an alkyl group having 4 to 18 carbon atoms.

The compound of formula (E) is an orange dye compound.

In the formula (E),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
X _E and Y _E preferably represent a chlorine atom.

In the formula (E),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
R _E is preferably an alkyl group having 4 to 12 carbon atoms.

In the formula (E),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
X _E and Y _E represent a chlorine atom,
R _E is preferably an alkyl group having 4 to 12 carbon atoms.

<Compound of general formula (F)>

In the compound of general formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms.

The compound of formula (F) is a violet dye compound.

In the formula (F),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
R _F1 and R _F2 preferably each independently represent an alkyl group having 4 to 12 carbon atoms.

<Compound of general formula (G)>

In the compound of general formula (G), R _G represents an alkyl group having 7 or 10 to 18 carbon atoms.

The compound of formula (G) is a yellow dye compound.

In the formula (G),
From the viewpoint of dye density, light fastness, sublimation fastness, etc.
R _G is preferably an alkyl group having 11 to 18 carbon atoms.

<Method for Producing Compound of Formula (A)>
A method for producing the compound represented by the formula (A) will be described.

The compound represented by the formula (A) is a 4-nitroaniline derivative represented by the formula (aD) (in formula (aD), _X represents a nitro group and _Y represents a halogen atom). and a compound represented by formula (aC) (wherein R _A1 , R _A2 and R _A3 each independently represent an alkyl group having 1 to 14 carbon atoms, provided that At least one of R _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms), and R _A4 represents an alkyl group having 1 to 4 carbon atoms).

(i) Diazotization of a compound of formula (aD) First, a compound of formula (aD) is treated in a mineral acid or organic carboxylic acid in the presence of optionally added water as a nitrosating agent or a nitrosyl. Diazotization using sulfuric acid gives the diazo compound. Organic carboxylic acids used include, for example, acetic acid and propionic acid. Mineral acids include, for example, hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is an alkali metal nitrite, such as sodium nitrite in solid or aqueous solution.

The diazotization reaction temperature is preferably -10 to 40°C, more preferably 0 to 40°C.

The compound represented by formula (aD) is generally and widely used as a starting material for azo disperse dyes.

(ii) Coupling with a Compound of Formula (aC) To a solution or suspension of a compound of formula (aC) in alcohol (e.g., methanol) is added the diazo compound of formula (aD). is added at a temperature of, for example, −5 to 10° C. to obtain the compound represented by the formula (A).

The pH of the compound solution or suspension of formula (aC) is preferably weakly acidic, and the addition of buffering agents such as triethylamine, sodium acetate, etc. may be advantageous in the coupling reaction.

The water content of the compound of general formula (A) may be within a range that allows production of an aqueous dispersion, for example, adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

(iii) Method for Producing Compound of Formula (aC) The compound of formula (aC), which is a starting material, can be produced as follows.

Using N,N-dimethylformamide (DMF) as a solvent, a compound represented by the formula (a-C1) (wherein R _A4 represents an alkyl group having 1 to 4 carbon atoms) is reacted with R _A3 A carboxylic acid halide represented by -COX (R _A3 represents an alkyl group having 1 to 14 carbon atoms and X represents a halogen atom) is reacted to obtain a compound represented by the formula (a-C2).

Next, the compound represented by formula (a-C2) is nitrated with concentrated nitric acid and concentrated sulfuric acid to obtain a compound represented by formula (a-C3).

A compound of formula (a-C3) is reduced with tin in a hydrochloric acid alcohol (eg, methanol) to give a compound of formula (a-C4).

R _A1 -X and R _A2 -X (R _A1 and R _A2 each independently represent an alkyl group having 1 to 14 carbon atoms, and X is (representing a halogen atom) is reacted to obtain the formula (aC).
Alternatively, a compound represented by formula (a-C4) is reacted with a halogenated hydrocarbon represented by R _A1 -X (R _A1 represents an alkyl group having 1 to 14 carbon atoms and X represents a halogen atom). After the reaction, R _A2 (R _A2 represents an alkyl group having 1 to 14 carbon atoms) may be introduced according to a known reaction. For example _, ( _RA2 ) _2SO4 can be used to introduce _RA2 .

<Method for producing compound of formula (B)>
A method for producing the compound represented by the formula (B) will be described.

The compound represented by the formula (B) includes a diazo compound of 3-amino-5-nitro-2,1-benzisothiazole represented by the formula (bD) and a diazo compound represented by the formula (bC). (In the formula (bC), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _B1 , R _B2 and R _B3 is carbon It is an alkyl group of numbers 4 to 14).).

(i) Diazotization of a compound of formula (bD) First, a compound of formula (bD) is treated with a nitrosating agent or nitrosyl in a mineral acid or organic carboxylic acid, optionally in the presence of additional water. Diazotization using sulfuric acid gives the diazo compound. Organic carboxylic acids used include, for example, acetic acid and propionic acid. Mineral acids include, for example, hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is an alkali metal nitrite, such as sodium nitrite in solid or aqueous solution.

The diazotization reaction temperature is preferably -10 to 15°C, more preferably -5 to 10°C.

The compound represented by formula (bD) is generally and widely used as a starting material for azo disperse dyes.

(ii) Coupling with a compound of formula (bC) To a solution or suspension of the compound of formula (bC) in alcohol (e.g., methanol) is added the diazo compound of formula (bD). is added at a temperature of, for example, −5 to 10° C. to obtain the compound represented by the formula (B).

The pH of the compound solution or suspension of formula (bC) is preferably weakly acidic, and the addition of buffering agents such as triethylamine, sodium acetate, etc. may be advantageous in the coupling reaction.

The water content of the compound of general formula (B) may be within a range that allows production of an aqueous dispersion, for example, adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

(iii) Method for Producing Compound of Formula (bC) The compound of formula (bC), which is a starting material, can be produced as follows.

Using DMF as a solvent, m-nitroaniline is reacted with a carboxylic acid halide represented by R _B3 —COX (where R _B3 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) to obtain the formula (b -C1) is obtained.

Compounds of formula (b-C1) are then reduced with tin in hydrochloric acid alcohol (eg, methanol) to give compounds of formula (b-C2).

R _B1 -X and R _B2 -X (R _B1 and R _B2 each independently represent an alkyl group having 1 to 14 carbon atoms, and X is (representing a halogen atom) is reacted to obtain the formula (bC).

Alternatively, a compound represented by formula (b-C2) is reacted with a halogenated hydrocarbon represented by R _B1 -X (R _B1 represents an alkyl group having 1 to 14 carbon atoms and X represents a halogen atom). After the reaction, R _B2 (R _B2 represents an alkyl group having 1 to 14 carbon atoms) may be introduced according to a known reaction. For example, (R _B2 ) ₂ SO ₄ can be used to introduce R _B2 .

<Method for producing compound of general formula (C)>
A method for producing the compound represented by the formula (C) will be described.

The compound represented by the formula (C) is a 4-nitroaniline derivative represented by the formula (cD) (in formula (cD), X _{and Y} are a hydrogen atom, a halogen atom, a halogen a diazo compound represented by the formula (cC), and a diazo compound represented by the formula (cC). (wherein R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _C1 , R _C2 and R _C3 has It is obtained by coupling )), which is an alkyl group of 4 or more.

(i) Diazotization of the compound of formula (cD) First, the compound of formula (cD) is nitrosated in a mineral acid or an organic carboxylic acid, optionally in the presence of additional water. diazotization using a reagent or nitrosylsulfuric acid to obtain the diazo compound. Organic carboxylic acids used include, for example, acetic acid and propionic acid. Mineral acids include, for example, hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is an alkali metal nitrite, such as sodium nitrite in solid or aqueous solution.

The diazotization temperature is preferably -10 to 40°C, more preferably 0 to 35°C.
The compound represented by formula (cD) is generally and widely used as a starting material for azo disperse dyes.

(ii) Coupling with a compound of formula (cC) To a solution or suspension of the compound of formula (cC) in alcohol (e.g., methanol) is added the diazo compound of formula (cD). is added at a temperature of, for example, −5 to 10° C. to obtain the compound represented by the formula (C).

The pH of the compound solution or suspension of formula (cC) is preferably weakly acidic and it may be advantageous to add a buffer such as triethylamine, sodium acetate and the like.
The water content of the compound of general formula (C) may be within a range that allows production of an aqueous dispersion, for example, adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

(iii) Method for Producing Compound of Formula (cC) The compound of formula (cC) as a starting material can be produced as follows.

Using DMF as a solvent, m-nitroaniline is reacted with a carboxylic acid halide represented by R _C3 —COX (R _C3 represents an alkyl group having 1 to 14 carbon atoms, and X is a halogen atom) to obtain the formula (c -C1) is obtained.

The compound of formula (c-C1) is then reduced with tin in a hydrochloric acid alcohol (eg methanol) to give the compound of formula (c-C2).

R _C1 -X and R _C2 -X (R _C1 and R _C2 each independently represent an alkyl group having 1 to 14 carbon atoms, and X is (which is a halogen atom) is reacted to obtain the formula (cC).

Alternatively, a compound represented by formula (c-C2) is reacted with a halogenated hydrocarbon represented by R _C1 -X (R _C1 represents an alkyl group having 1 to 14 carbon atoms and X represents a halogen atom). After the reaction, R _C2 (R _C2 represents an alkyl group having 1 to 14 carbon atoms) may be introduced according to a known reaction. For example, (R _C2 ) ₂ SO ₄ can be used to introduce R _C2 .

<Method for producing compound of formula (D)>
A method for producing the compound represented by the formula (D) will be described.

The compound represented by formula (D) is a 4-nitroaniline derivative represented by formula (dD) (in formula (dD), X _D and Y _D are each independently a hydrogen atom, a halogen atom , or represents a cyano group) and a compound represented by the formula (dC) (wherein R _D1 represents an alkyl group having 1 to 14 carbon atoms, and R _D2 is , represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN, provided that at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms. Obtained by coupling.

(i) Diazotization of the compound of formula (dD) First, the compound of formula (dD) is nitrosated in a mineral acid or an organic carboxylic acid, optionally in the presence of additional water. diazotization using a reagent or nitrosylsulfuric acid to obtain the diazo compound. Organic carboxylic acids used include, for example, acetic acid and propionic acid. Mineral acids include, for example, hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is an alkali metal nitrite, such as sodium nitrite in solid or aqueous solution.

The diazotization temperature is preferably -10 to 40°C, more preferably 0 to 30°C.
The compound represented by formula (dD) is generally and widely used as a starting material for azo disperse dyes.

(ii) Coupling with a compound of formula (dD) To a solution or suspension of the compound of formula (dC) in alcohol (e.g., methanol) is added the diazo compound of formula (dD). is added at a temperature of, for example, −5 to 10° C. to obtain the compound represented by the formula (D).

The pH of the compound solution or suspension of formula (dC) is preferably weakly acidic and it may be advantageous to add a buffer such as triethylamine, sodium acetate and the like.

The water content of the compound of general formula (D) may be within a range that allows production of an aqueous dispersion, for example, adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

(iii) Method for Producing Compound of Formula (dC) The compound of formula (dC), which is a starting material, can be produced as follows.

R _D1 -X and R _D2 -X (R _D1 represents an alkyl group having 1 to 14 carbon atoms and R _D2 represents an alkyl group having 1 to 14 carbon atoms or R D2 substituted with CN or represents an alkyl group having 1 to 14 carbon atoms, provided that at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms, and X is a halogen atom. to obtain the formula (dC).

Alternatively, aniline is reacted with a halogenated hydrocarbon represented by R _D1 -X (R _D1 represents an alkyl group having 1 to 14 carbon atoms and X represents a halogen atom), followed by a known reaction to obtain R _D2 (R _D2 represents an alkyl group having 1 to 14 carbon atoms) may be introduced. For example, (R _D2 ) ₂ SO ₄ can be used to introduce R _D2 .

<Method for producing compound of formula (E)>
A method for producing the compound represented by the formula (E) will be described.

The compound represented by the formula (E) is a diazo compound of a 4-nitroaniline derivative represented by the formula (eD) (in which X _E and Y _E represent a halogen atom). with a compound represented by formula (eC) (in formula (eC), R _E represents an alkyl group having 4 to 18 carbon atoms).

(i) Diazotization of the compound of formula (eD) First, the compound of formula (eD) is nitrosated in a mineral acid or an organic carboxylic acid, optionally in the presence of additional water. diazotization using a reagent or nitrosylsulfuric acid to obtain the diazo compound. Organic carboxylic acids used include, for example, acetic acid and propionic acid. Mineral acids also include, for example, hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is an alkali metal nitrite, such as sodium nitrite in solid or aqueous solution.

The diazotization temperature is preferably -10 to 40°C, more preferably 0 to 30°C.
The compound represented by formula (eD) is generally and widely used as a starting material for azo disperse dyes.

(ii) Coupling with a Compound of Formula (eC) To a solution or suspension of the compound of formula (eC) in alcohol (e.g., methanol) is added the diazo compound of formula (eD). is added at a temperature of, for example, −5 to 10° C. to obtain the compound represented by the formula (E).

The pH of the compound solution or suspension of formula (eC) is preferably weakly acidic and it may be advantageous to add a buffer such as triethylamine, sodium acetate and the like.

The water content of the compound of general formula (E) may be within a range that allows production of an aqueous dispersion, for example, adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

(iii) Method for Producing Compound of Formula (eC) The compound of formula (eC) as a starting material can be produced as follows.

Using DMF as a solvent, a 2-phenyl-1H-indole represented by the formula (e-C1) is reacted with R _E1 -X (R _E1 represents an alkyl group having 4 to 18 carbon atoms and X is a halogen atom). The represented alkyl halides are reacted to give formula (eC).

<Method for Producing Compound of Formula (F)>
A method for producing the compound represented by the formula (F) will be described.

The compound represented by the formula (F) includes a diazo compound of 3-amino-5-nitro-2,1-benzisothiazole represented by the formula (fD) and a diazo compound represented by the formula (fC). (In formula (fC), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms).

(i) Diazotization of the compound of formula (fD) First, the compound of formula (fD) is nitrosated in a mineral acid or an organic carboxylic acid, optionally in the presence of additional water. diazotization using a reagent or nitrosylsulfuric acid to obtain the diazo compound. Organic carboxylic acids used include, for example, acetic acid and propionic acid. Mineral acids include, for example, hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is an alkali metal nitrite, such as sodium nitrite in solid or aqueous solution.

The diazotization temperature is preferably -10 to 15°C, more preferably -5 to 10°C.
The compound represented by formula (fD) is generally and widely used as a starting material for azo disperse dyes.

(ii) Coupling with a Compound of Formula (fC) To a solution or suspension of a compound of formula (fC) in alcohol (e.g., methanol) is added the diazo compound of formula (fD). is added at a temperature of, for example, −5 to 10° C. to obtain the compound represented by the formula (F).

The pH of the compound solution or suspension of formula (fC) is preferably weakly acidic and it may be advantageous to add a buffering agent such as triethylamine, sodium acetate and the like.
The water content of the compound of general formula (F) may be within a range that allows production of an aqueous dispersion, for example, adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

(iii) Method for Producing Compound of Formula (fC) The compound of formula (fC) as a starting material can be produced as follows.

Halogens represented by R _F1 -X and R _F2 -X (R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms and X is a halogen atom) are added to aniline using DMF as a solvent. to give formula (fC).

Alternatively, aniline is reacted with a halogenated hydrocarbon represented by R _F1 -X (R _F1 represents an alkyl group having 1 to 14 carbon atoms and X represents a halogen atom), followed by a known reaction, followed by R _F2 (R _F2 represents an alkyl group having 1 to 14 carbon atoms) may be introduced. For example, (R _F2 ) ₂ SO ₄ can be used to introduce R _F2 .

<Method for producing compound of general formula (G)>
A method for producing the compound represented by the formula (G) will be described.

The compound represented by formula (G) is converted to 5-amino-anthra[9,1-cd]isothiazol-6-one represented by formula (g) in an inert solvent such as toluene, xylene or chlorobenzene. and a carboxylic acid halide represented by R _G -COX (R _G represents an alkyl group having 7 to 18 carbon atoms and X is a halogen atom).

The reaction temperature is preferably 80°C to 140°C, more preferably 110°C to 140°C.
The compound represented by formula (g) is generally and widely used as a raw material for polycyclic disperse dyes.

The water content of the compound of general formula (G) may be within a range that allows production of an aqueous dispersion, for example, adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

<Dye composition>
As described above, the dye composition of the present invention contains at least one of the compounds represented by formulas (A) to (G) and a nonionic dispersant.

Examples of the nonionic dispersant include polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene arylphenyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene aryl aryl ether, polyoxyethylene sorbitan fatty acid ester, poly Oxyethylene acetylene glycol, polyvinyl alcohol, polyvinylpyrrolidone, oxyethylene-oxypropylene copolymer and the like. Among these, at least one selected from polyoxyethylene alkylphenyl ethers, polyoxyethylene arylphenyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene aryl aryl ethers, and oxyethylene-oxypropylene copolymers should be used. is preferred, and it is more preferred to use at least one selected from polyoxyethylene aryl phenyl ether, polyoxyethylene aryl aryl ether, oxyethylene-oxypropylene copolymer, polyoxyethylene aryl phenyl ether, oxyethylene-oxy It is more preferable to use at least one selected from propylene copolymers.

The polymerization form of the oxyethylene-oxypropylene copolymer is not particularly limited, and may be a random polymer, a block polymer, or the like.
In addition, in order to use the dye composition in the form of a powder by spray drying or the like, instead of a liquid aqueous dispersion, the nonionic dispersant includes polyoxyethylene arylphenyl ether and oxyethylene-oxy Preferably both propylene copolymers are included.

The amount of the nonionic dispersant to be used is based on the mass of the compound represented by the formulas (A) to (G) for the purpose of maintaining good dispersion stability of the compounds represented by the formulas (A) to (G). 20 to 200% by mass, more preferably 20 to 100% by mass.

The dye composition of the present invention may contain a viscosity modifier, a surface tension modifier, a pH modifier, a humectant, a hydrotrope agent, a sequestering agent, a preservative, and a preservative, as long as they do not interfere with the achievement of the object of the invention. A mold agent, an antifoaming agent, etc. may be added as necessary.

The dye composition of the present invention may further contain additives. Examples of the additives include auxiliary colorants, dispersants, fillers, stabilizers, plasticizers, crystal nucleating agents, modifiers, foaming agents, ultraviolet absorbers, light stabilizers, antioxidants, antibacterial agents, Examples include antifungal agents, antistatic agents, flame retardants, inorganic fillers, and elastomers for improving impact resistance.

The dye composition of the present invention is desirably an aqueous dispersion from the viewpoint of ease of handling, safety and the like. Since the compounds represented by the formulas (A) to (G) have high lipophilicity, in order to obtain a dye composition in the form of an aqueous dispersion, the dispersant is used in combination, and fine particles are obtained using a dispersing machine such as a bead mill. Decentralized processing is required.

The dye composition of the present invention is a liquid aqueous dispersion in which the compounds represented by formulas (A) to (G) are finely dispersed in an aqueous dispersion medium using a nonionic dispersant, or the above It may be in the form of powder obtained by removing the dispersion medium of the liquid aqueous dispersion by spray drying or the like, but it is preferably in the form of powder from the viewpoint of product life.

The content of the compounds represented by formulas (A) to (G) in the dye composition of the present invention may be within a range that maintains ease of handling during dyeing, preferably 5 to 40% by mass, more preferably is 10 to 30% by mass.

The method for producing the dye composition of the invention preferably includes the following methods.
(1) A nonionic dispersant and, if necessary, various additives such as a viscosity modifier are added to water and stirred to prepare a dispersant solution.
(2) Add the compounds represented by the formulas (A) to (G) to the dispersant solution of (1) and stir to prepare an aqueous slurry.
(3) Using a wet dispersing machine such as a bead mill, the fine particle dispersion treatment of the aqueous slurry of (2) is performed so that the volume median particle size of the compounds represented by formulas (A) to (G) is 1.0 μm or less, preferably This is continued until the thickness becomes 0.5 μm or less.
(4) Water is added to the fine particle-dispersed product of (3) to adjust the concentration to obtain a liquid aqueous dispersion.
(5) Various additives such as a dispersant are added to the liquid aqueous dispersion of (4), if necessary, and the mixture is stirred, and the dispersion medium is removed by spray drying or the like to obtain a powdery dye composition.
Using the obtained (4) liquid aqueous dispersion or (5) powdery dye composition, fibers can be subjected to aqueous dyeing by a dip dyeing method, a textile printing method, or the like.

The compounds of general formulas (A) to (G) contained in the dye composition for dyeing the fibers of the invention have a blue, violet, red, orange or yellow color. The dye composition may contain one or more of the compounds of formulas (A) to (G). When the dye composition contains two or more compounds of general formulas (A) to (G), dyes for dyeing fibers in various shades or black can be obtained.

The dye composition for dyeing fibers black is selected from the group consisting of compounds of general formula (A), compounds of general formula (B), compounds of general formula (C), and compounds of general formula (F). At least one purple or blue compound containing one or more and at least one red compound containing one or more selected from the group consisting of compounds of general formula (C) and compounds of general formula (D) and at least one yellow or orange compound selected from the compound of general formula (D), the compound of general formula (E) and the compound of general formula (G), and the compound of general formula (A) at least one purple or blue compound containing one or more selected from the group consisting of a compound, a compound of general formula (B) and a compound of general formula (F), and a red compound of the compound of general formula (C) and at least one orange compound including one or more selected from the group consisting of the compound of general formula (D) and the compound of general formula (E), and the compound of general formula (A) and a red compound of the compound of general formula (C) and an orange compound of the compound of general formula (D).

The composition of the compounds in the dye composition for dyeing fibers black is such that the mixing ratio of the purple or blue compound is 30 to 70% by mass, the mixing ratio of the red compound is 5 to 25% by mass, and the yellow Alternatively, the mixing ratio of the orange compound is preferably in the range of 15 to 55% by mass, the mixing ratio of the purple or blue compound is 40 to 60% by mass, and the mixing ratio of the red compound is 5 to 25% by mass. , the mixing ratio of the yellow or orange compound is more preferably in the range of 25 to 45% by mass.

Examples of fibers to be dyed in the present invention include polyester fibers, polyolefin fibers, and acrylic fibers, and polyolefin fibers are preferred.

The polyolefin fibers are, for example, homopolymers of α-olefins such as propylene, ethylene, 1-butene, 3-methyl-1-butene, 4-methyl-1-pentene and 1-octene, and copolymers of these α-olefins. polymers, or copolymers of these α-olefins with other unsaturated monomers copolymerizable with them. Further, examples of the types of copolymers include block copolymers, random copolymers, graft copolymers, and the like. Specific examples of the polymer include polypropylene resins such as propylene homopolymer, propylene-ethylene block copolymer, propylene-ethylene random copolymer, propylene-ethylene-(1-butene) copolymer, etc., low density Polyethylene resins such as polyethylene, medium density polyethylene, high density polyethylene, linear low density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, poly 1-butene, poly 4-methyl-1 - includes pentene and the like.

The above polymers may be used singly or in combination of two or more to form polyolefin fibers.

The polyolefin fibers are preferably made of polypropylene-based resin and/or polyethylene-based resin, and more preferably made of polypropylene-based resin.

The shape of the polyolefin fiber is, for example, block-like (molded article, etc.), film-like, fibrous (cloth-like (woven fabric, knitted fabric, non-woven fabric, etc.), thread-like (filament yarn, spun yarn, slit yarn, split yarn, etc.), etc.). etc., preferably fibrous.

The polyolefin fibers may be fibers formed by mixing polypropylene resin and/or polyethylene resin with other polymer components, bonding, or the like. The polyolefin fibers may be obtained by blending or blending polypropylene fibers with other fibers such as polyester.

<Fiber dyeing method>
The present invention, as described above, provides a method of dyeing fibers comprising the step of water-based dyeing the fibers using the dye composition of the present invention.

The dyeing step is preferably at least one selected from the group consisting of dyeing, textile printing, inkjet dyeing, transfer dyeing, and continuous dyeing, and at least one selected from dyeing and textile printing. Printing is more preferred, and printing is even more preferred. When the dyeing step is dip dyeing, the dyeing step is performed, for example, by applying the dye composition of the present invention under pressure, preferably at 80° C. to 130° C., more preferably 90° C. to 120° C., preferably It is performed by soaking for 30 to 60 minutes.

When the fiber is polyolefin, the dyeing process is preferably carried out at 80°C to 130°C. The dyeing process is preferably performed for 30 to 60 minutes.

When the fiber is polypropylene, the dyeing process is preferably carried out at 110°C to 130°C. The dyeing process is preferably performed for 30 to 60 minutes.

When the fiber is polyethylene, the dyeing process is preferably carried out at 90°C to 110°C. The dyeing process is preferably performed for 30 to 60 minutes.

When the dyeing step is textile printing, the dyeing step includes, for example, mixing the dye composition of the present invention with a sizing agent such as a natural sizing agent (e.g., guar gum, etc.) or a processed sizing agent (e.g., carboxymethylcellulose, etc.). After printing the prepared printing paste on the material to be dyed, for example, it is subjected to steaming treatment at 90° C. to 200° C. for 1 minute to 20 minutes or dry heat treatment for 20 seconds to 5 minutes.

When the fiber is polyolefin, it is preferable that the dyeing process is performed at 80° C. to 130° C. and the steaming treatment is performed for 1 minute to 10 minutes.

When the fiber is polypropylene, the dyeing step is preferably performed at 110° C. to 130° C. and the steaming treatment is performed for 1 minute to 10 minutes.

When the fiber is polyethylene, the dyeing step is preferably performed at 90° C. to 110° C. and the steaming treatment is performed for 1 minute to 10 minutes.

When the dyeing step is inkjet dyeing, the dyeing step includes, for example, adding a low-volatile water-soluble organic solvent such as glycerin and diethylene glycol to the liquid dye composition of the present invention to prepare an ink for inkjet printing, After printing with an inkjet printer on a cloth or fiber to which a sizing agent or the like has been applied in advance by padding or the like, or on a formed fiber, for example, steaming treatment at 90 ° C. to 200 ° C. for 1 minute to 20 minutes, Alternatively, dry heat treatment is performed for 20 seconds to 5 minutes.

In the case of exhaust dyeing, the concentration of the dyes of the invention on said fibers is, for example, 0.001% o.d. m. f. to 10% o.d. m. f. and preferably 0.001% o.d. m. f. to 5% o.o. m. f. is. It should be noted that o. m. f. means on the mass of fiber.

In the case of printing, the concentration of the dyes of the present invention to said printing paste is, for example, 0.001% o.d. m. p. to 5% o.d. m. p. and preferably 0.001% o.d. m. p. to 2% o.o. m. p. is. It should be noted that o. m. p. means on the mass of paste.

The present invention provides fibers dyed by the dyeing method of the present invention. Applications of the fibers include, for example, clothing such as clothing, underwear, hats, socks, gloves, and sports clothing, vehicle interior materials such as seat sheets, and interior goods such as carpets, curtains, mats, sofa covers, and cushion covers. etc.

EXAMPLES The present invention will be described in more detail below with reference to Examples, but the aspects of the present invention are not limited to these.
[Example]

(Synthesis example 1)
[Synthesis of blue dye compound (A-1)]
A blue dye compound (A-1) was produced according to the following scheme.

1-A. Synthesis of coupler compound (C1) and preparation of coupler component solution (step 1)
p-Anisidine (purchased commercially) (24.6 g) was dissolved in DMF (35 g) and pyridine (19 g) was added dropwise. After dropping n-octanoyl chloride (purchased as a commercial product) (34.2 g), the mixture was heated to 110° C. and stirred for 1 hour. After cooling to room temperature, 2M hydrochloric acid (150 ml) was added to precipitate a precipitate. The mixture was filtered, washed with water and dried to obtain N-(4-methoxyphenyl)octanamide (53.1 g, yield 106.5%) represented by the following formula (C1a) as a crude product.

(Step 2)
To concentrated sulfuric acid (30 g) cooled to 5°C, the N-(4-methoxyphenyl)octanamide (12.5 g) obtained in step 1 above was slowly added in the range of 5 to 10°C. Concentrated nitric acid (4.57 g) was added dropwise to the mixture at 5 to 10°C over 1 hour, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was purged into ice water (150 g) and ethyl acetate (100 g) was added to extract the organic phase. This extract was washed with saturated brine, and the solvent was distilled off under reduced pressure to obtain N-(3-nitro-4-methoxyphenyl)octanamide represented by the following formula (C1b) (16.9 g, yield 114). .8%) was obtained as a crude product.

(Step 3)
A mixture of N-(3-nitro-4-methoxyphenyl)octanamide (16.9 g) obtained in Step 2 above, tin (8.9 g) and methanol (7.5 g) was cooled to 5°C. After concentrated hydrochloric acid (31.4 g) was added dropwise to this mixture over 1 hour, the temperature was raised to 75 to 80° C. and stirred for 40 minutes. After cooling the reaction mixture to 10°C, 48% aqueous sodium hydroxide solution (55.2 ml) was slowly added in the range of 10 to 20°C. The mixture was filtered, washed with water and dried to obtain N-(3-amino-4-methoxyphenyl)octanamide (9.19 g, yield 69.5%) represented by the following formula (C1c).

(Step 4)
N-(3-Amino-4-methoxyphenyl)octanamide (13.2 g) obtained in Step 3 above, triethylamine (15 g), DMF (15 g) and 1-bromooctane (purchased commercially) (38. 6g) was heated to 120° C. and stirred at the same temperature for 3 hours to give N-[3-(N,N-dioctylamino)-4-methoxyphenyl]octane represented by the following formula (C1). amide was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C1).

1-B. Preparation of diazo component solution (Step 5)
To a mixture of concentrated sulfuric acid (16 g) and 43% nitrosylsulfuric acid (12.8 g), 2-bromo-4,6-dinitroaniline (13.1 g) represented by the following formula (D1) was added at 25 to 30°C. added slowly. The mixture was stirred at 30 to 40°C for 2 hours to obtain a diazo component solution.

1-C. Synthesis of blue dye compound (A-1) by coupling reaction (step 6)
The diazo component solution obtained in the step 5 is added dropwise to the coupler component solution obtained in the step 4 over 2 hours while adding triethylamine (84 g) appropriately within the range of 0 to 10° C. to effect coupling. reacted. After stirring the mixture for 30 minutes between 0 and 10° C., the product is filtered off from the reaction mixture, washed with methanol, then water and heated at 60° C. until the water content is below 1.0% by weight. After drying, a blue dye compound (5.93 g, yield 15.5%) represented by the following formula (A-1) was obtained. The structure of the blue-stained compound was confirmed by LCMS analysis (m/z 761 (M ⁺ )).

(Synthesis example 2)
[Synthesis of blue dye compound (A-2)]
A blue dye compound (A-2) was produced according to the following scheme.

2-A. Synthesis of coupler compound (C2) and preparation of coupler component solution (Step 1)
In the same manner as in steps 1 to 4 of Synthesis Example 1, except that valeryl chloride (25.3 g) is used instead of n-octanoyl chloride in Step 1 of Synthesis Example 1, the compound represented by the following formula (C2) N-[3-(N,N-dioctylamino)-4-methoxyphenyl]pentanamide was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C2).

2-B. Synthesis of blue dye compound (A-2) by coupling reaction (step 2)
The following formula (A-2 ) was obtained (8.03 g, yield 22.3%). This blue-stained compound confirmed its structure by LCMS analysis (m/z 719 (M ⁺ )).

(Synthesis Example 3)
[Synthesis of blue dye compound (A-3)]
A blue dye compound (A-3) was produced according to the following scheme.

3-A. Synthesis of coupler compound (C3) and preparation of coupler component solution (Step 1)
N represented by the following formula (C3) in the same manner as in steps 1 to 4 of Synthesis Example 1, except that propionyl chloride (19.4 g) is used instead of n-octanoyl chloride in Step 1 of Synthesis Example 1. -[3-(N,N-dioctylamino)-4-methoxyphenyl]propanamide was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C3).

3-B. Synthesis of blue dye compound (A-3) by coupling reaction (step 2)
The following formula (A-3 ) was obtained (5.85 g, yield 16.9%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 691 (M ⁺ )).

(Synthesis Example 4)
[Synthesis of blue dye compound (A-4)]
A blue dye compound (A-4) was produced according to the following scheme.

4-A. Synthesis of coupler compound C4 and preparation of coupler component solution (step 1)
In Step 1 of Synthesis Example 1, except for using 2-ethylhexanoyl chloride (34.2 g) instead of n-octanoyl chloride, in the same manner as in Steps 1 to 4 of Synthesis Example 1, the following formula (C4) N-[3-(N,N-dioctylamino)-4-methoxyphenyl]-2-ethylhexanamide of the formula was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C4).

4-B. Synthesis of blue dye compound (A-4) by coupling reaction (step 2)
The following formula (A-4 ) was obtained (9.63 g, yield 25.3%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 761 (M ⁺ )).

(Synthesis Example 5)
[Synthesis of blue dye compound (A-5)]
A blue dye compound (A-5) was produced according to the following scheme.

5-A. Synthesis of coupler compound C5 and preparation of coupler component solution (Step 1)
In step 4 of Synthesis Example 1, N-(3-amino-4-methoxyphenyl)acetamide (purchased commercially) (9.0 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide. N-[3-(N,N-dioctylamino)-4-methoxyphenyl]acetamide represented by the following formula (C5) was obtained in the same manner as in Step 4 of Synthesis Example 1, except that N-[3-(N,N-dioctylamino)-4-methoxyphenyl]acetamide was used. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C5).

5-B. Synthesis of blue dye compound (A-5) by coupling reaction (step 2)
The following formula (A-5 ) was obtained (20.3 g, yield 60.0%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 677 (M ⁺ )).

(Synthesis Example 6)
[Synthesis of blue dye compound (A-6)]
A blue dye compound (A-6) was produced according to the following scheme.

6-A. Synthesis of coupler compound (C6) and preparation of coupler component solution (Step 1)
In step 4 of Synthesis Example 1, 1-bromododecane (49.8 g) was used in place of 1-bromooctane, N-(3- N-[3-(N,N-didodecylamino )-4-methoxyphenyl]acetamide. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C6).

6-B. Synthesis of blue dye compound (A-6) by coupling reaction (step 2)
The following formula (A-6 ) was obtained (19.3 g, yield 48.9%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 789 (M ⁺ )).

(Synthesis Example 7)
[Synthesis of blue dye compound (A-7)]
A blue dye compound (A-7) was produced according to the following scheme.

7-A. Synthesis of Coupler Compound C7 and Preparation of Coupler Component Solution (Step 1)
In step 4 of Synthesis Example 1, N-[ 3-(N,N-diethylamino)-4-methoxyphenyl]octanamide was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C7).

7-B. Synthesis of blue dye compound (A-7) by coupling reaction (step 2)
The following formula (A-7 ) was obtained (7.71 g, yield 26.0%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 593 (M ⁺ )).

(Synthesis Example 8)
[Synthesis of blue dye compound (A-8)]
A blue dye compound (A-8) was produced according to the following scheme.

8-A. Synthesis of coupler compound C8 and preparation of coupler component solution (step 1)
In Step 1 of Synthesis Example 1, N represented by the following formula (C8) was prepared in the same manner as in Steps 1 to 4 of Synthesis Example 1, except that 4-ethoxyaniline (27.4 g) was used instead of p-anisidine. -[3-(N,N-dioctylamino)-4-ethoxyphenyl]octanamide was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C8).

8-B. Synthesis of blue dye compound (A-8) by coupling reaction (step 2)
The following formula (A-8 ) was obtained (4.50 g, yield 11.6%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 775 (M ⁺ )).

(Synthesis Example 9)
[Synthesis of blue dye compound (B-1)]
A blue dye compound (B-1) was produced according to the following scheme.

9-A. Synthesis of coupler compound C9 and preparation of coupler component solution (Step 1)
N-(3-nitrophenyl)octanamide ( 53.6 g, 101.4% yield) was obtained as a crude product.

(Step 2)
In the same manner as in Step 3 of Synthesis Example 1, except for using N-(3-nitrophenyl)octanamide (13.2 g) instead of N-(3-nitro-4-methoxyphenyl)octanamide, the following formula N-(3-aminophenyl)octanamide (9.48 g, yield 80.9%) represented by (C9b) was obtained.

(Step 3)
In the same manner as in Step 4 of Synthesis Example 1, except for using N-(3-aminophenyl)octanamide (11.7 g) instead of N-(3-amino-4-methoxyphenyl)octanamide, the following formula N-[3-(N,N-dioctylamino)phenyl]octanamide of (C9) was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C9).

9-B. Preparation of diazo component solution (step 4)
To a mixture of concentrated sulfuric acid (29 g) and 43% nitrosylsulfuric acid (12.7 g), 3-amino-5-nitro-2,1-benzisothiazole (8.15 g) represented by the following formula (D2) was added from 0 to Add slowly within 5°C. To this mixture, 80% acetic acid (10 g) was slowly added dropwise within the range of 0 to 5°C, followed by stirring at the same temperature for 2 hours to obtain a diazo component solution.

9-C. Synthesis of blue dye compound (B-1) by coupling reaction (step 5)
The diazo component solution (D2) was added dropwise to the coupler component solution (C9) at a temperature within the range of 0 to 10° C. over 2 hours while appropriately adding triethylamine (43 g) to carry out a coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. A blue dye compound (20.9 g, yield 62.9%) represented by the following formula (B-1) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 665 (M ⁺ )).

(Synthesis Example 10)
[Synthesis of blue dye compound (B-2)]
A blue dye compound (B-2) was produced according to the following scheme.

10-A. Synthesis of coupler compound C10 and preparation of coupler component solution (Step 1)
In Step 1 of Synthesis Example 9, in the same manner as in Steps 1 to 3 of Synthesis Example 9 except that valeryl chloride (25.3 g) is used instead of n-octanoyl chloride, a compound represented by the following formula (C10) N-[3-(N,N-dioctylamino)phenyl]pentanamide was obtained. Methanol (30 g) was added to the reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C10).

10-B. Synthesis of blue dye compound (B-2) by coupling reaction (step 2)
Formula (B-2) below was prepared in the same manner as in Steps 4 and 5 of Synthesis Example 9, except that the compound of Formula (C10) obtained in Step 1 was used as the coupler component solution instead of the compound of Formula (C9). A blue dye compound (9.47 g, yield 30.4%) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 623 (M ⁺ )).

(Synthesis Example 11)
[Synthesis of blue dye compound (B-3)]
A blue dye compound (B-3) was produced according to the following scheme.

11-A. Synthesis of coupler compound C11 and preparation of coupler component solution (Step 1)
N represented by the following formula (C11) in the same manner as in steps 1 to 3 of Synthesis Example 9, except that propionyl chloride (19.4 g) is used instead of n-octanoyl chloride in Step 1 of Synthesis Example 9. -[3-(N,N-dioctylamino)phenyl]propanamide was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C11).

11-B. Synthesis of blue dye compound (B-3) by coupling reaction (step 2)
The following formula (B-3 ) was obtained (13.4 g, yield 45.0%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 595 (M ⁺ )).

(Synthesis Example 12)
[Synthesis of blue dye compound (B-4)]
A blue dye compound (B-4) was produced according to the following scheme.

12-A. Synthesis of coupler compound C12 and preparation of coupler component solution (Step 1)
In the same manner as in Step 3 of Synthesis Example 9, except for using 3′-aminoacetanilide (7.50 g) instead of N-(3-aminophenyl)octanamide in Step 3 of Synthesis Example 9, the following formula ( N-[3-(N,N-dioctylamino)phenyl]acetamide of C12) was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C12).

12-B. Synthesis of blue dye compound (B-4) by coupling reaction (step 2)
A blue dye compound represented by the following formula (B-4) was prepared in the same manner as in steps 4 and 5 of Synthesis Example 9, except that the compound of formula (C12) was used instead of the compound of formula (C9) as the coupler component solution. (20.3 g, 69.9% yield). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 581 (M ⁺ )).

(Synthesis Example 13)
[Synthesis of blue dye compound (B-5)]
A blue dye compound (B-5) was produced according to the following scheme.

13-A. Synthesis of coupler compound C13 and preparation of coupler component solution (Step 1)
In step 3 of Synthesis Example 9, 1-bromododecane (49.8 g) was substituted for 1-bromooctane, 3′-aminoacetanilide (7.50 g) was substituted for N-(3-aminophenyl)octanamide ) in the same manner as in Step 3 of Synthesis Example 9, to obtain N-[3-(N,N-didodecylamino)phenyl]acetamide represented by the following formula (C13). Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C13).

13-B. Synthesis of blue dye compound (B-5) by coupling reaction (step 2)
The following formula (B-5 ) was obtained (9.81 g, yield 28.3%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 693 (M ⁺ )).

(Synthesis Example 14)
[Synthesis of blue dye compound (B-6)]
A blue dye compound (B-6) was produced according to the following scheme.

14-A. Synthesis of Coupler Compound C14 and Preparation of Coupler Component Solution (Step 1)
Using propionyl chloride (19.4 g) in place of n-octanoyl chloride in step 1 of Synthesis Example 9, and 1-bromododecane (49.8 g) in place of 1-bromooctane in step 3 of Synthesis Example 9. N-[3-(N,N-didodecylamino)phenyl]propanamide represented by the following formula (C14) was obtained in the same manner as in Steps 1 to 3 of Synthesis Example 9 except for using . Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C14).

14-B. Synthesis of blue dye compound (B-6) by coupling reaction (step 2)
A blue dye represented by the following formula (B-6) was prepared in the same manner as in steps 4 and 5 of Synthesis Example 9, except that the compound of formula (C14) was used instead of the compound of formula (C9) as the coupler component solution. The compound (5.73 g, 16.2% yield) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 707 (M ⁺ )).

(Synthesis Example 15)
[Synthesis of blue dye compound (B-7)]
A blue dye compound (B-7) was produced according to the following scheme.

15-A. Synthesis of coupler compound C15 and preparation of coupler component solution (step 1)
Substituting 3′-aminoacetanilide (7.50 g) for N-(3-aminophenyl)octanamide and 1-bromo-2-ethylhexane for 1-bromooctane in step 3 of Synthetic Example 9 N-[3-[N,N-di(2-ethylhexyl)amino]phenyl]propane represented by the following formula (C15) in the same manner as in Step 3 of Synthesis Example 9, except for using (38.6 g). amide was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C15).

15-B. Synthesis of blue dye compound (B-7) by coupling reaction (step 2)
A blue dye represented by the following formula (B-7) was prepared in the same manner as in steps 4 and 5 of Synthesis Example 9, except that the compound of formula (C15) was used instead of the compound of formula (C9) as the coupler component solution. The compound (4.72 g, 16.2% yield) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 581 (M ⁺ )).

(Synthesis Example 16)
[Synthesis of blue dye compound (B-8)]
A blue dye compound (B-8) was produced according to the following scheme.

16-A. Synthesis of coupler compound C16 and preparation of coupler component solution (step 1)
N represented by the following formula (C16) in the same manner as in steps 1 to 3 of Synthesis Example 9, except that 1-bromoethane (27.3 g) is used instead of 1-bromooctane in Step 3 of Synthesis Example 9. -[3-(N,N-diethylamino)phenyl]octanamide was obtained. Methanol (30 g) was added to the reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C16).

16-B. Synthesis of blue dye compound (B-8) by coupling reaction (step 2)
The following formula (B-8 ) was obtained (23.2 g, yield 93.4%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 497 (M ⁺ )).

(Synthesis Example 17)
[Synthesis of red dye compound (C-1)]
A red dye compound (C-1) was produced according to the following scheme.

17-A. Preparation of diazo component solution (step 1)
2-Chloro-4-nitroaniline (8.65 g) represented by the following formula (D3) was added to a mixture of concentrated sulfuric acid (16 g) and 43% nitrosylsulfuric acid (15.6 g) within the range of 30 to 35°C. , and stirred at the same temperature for 2 hours to obtain a diazo component solution.

17-B. Synthesis of red dye compound (C-1) by coupling reaction (step 2)
A coupler component solution comprising the compound of formula (C9) was prepared in the same manner as steps 1 to 3 of Synthesis Example 9. The diazo component solution obtained in step 1 was added dropwise to the coupler component solution at a temperature within the range of 0 to 10°C over 2 hours while appropriately adding triethylamine (28 g) to carry out a coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. A red dye compound (24.3 g, yield 75.7%) represented by the following formula (C-1) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 642 (M ⁺ )).

(Synthesis Example 18)
[Synthesis of red dye compound (C-2)]
A red dye compound (C-2) was produced according to the following scheme.

A red dye represented by the following formula (C-2) was prepared in the same manner as in steps 1 and 2 of Synthesis Example 17, except that the compound of formula (C10) was used instead of the compound of formula (C9) as the coupler component solution. The compound (10.4 g, 34.7% yield) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 600 (M ⁺ )).

(Synthesis Example 19)
[Synthesis of red dye compound (C-3)]
A red dye compound (C-3) was produced according to the following scheme.

A red dye represented by the following formula (C-3) was prepared in the same manner as in steps 1 and 2 of Synthesis Example 17, except that the compound of formula (C11) was used instead of the compound of formula (C9) as the coupler component solution. A compound (12.9 g, 45.1% yield) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 572 (M ⁺ )).

(Synthesis Example 20)
[Synthesis of red dye compound (C-4)]
A red dye compound (C-4) was produced according to the following scheme.

A red dye represented by the following formula (C-4) was prepared in the same manner as in steps 1 and 2 of Synthesis Example 17, except that the compound of formula (C12) was used instead of the compound of formula (C9) as the coupler component solution. A compound (23.4 g, yield 83.9%) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 558 (M ⁺ )).

(Synthesis Example 21)
[Synthesis of red dye compound (C-5)]
A red dye compound (C-5) was produced according to the following scheme.

A red dye represented by the following formula (C-5) was prepared in the same manner as in steps 1 and 2 of Synthesis Example 17, except that the compound of formula (C13) was used instead of the compound of formula (C9) as the coupler component solution. The compound (25.3 g, yield 75.5%) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 670 (M ⁺ )).

(Synthesis Example 22)
[Synthesis of red dye compound (C-6)]
A red dye compound (C-6) was produced according to the following scheme.

22-A. Synthesis of coupler compound C17 and preparation of coupler component solution (step 1)
Substituting 3′-aminoacetanilide (7.50 g) for N-(3-aminophenyl)octanamide and 1-bromobutane (27.4 g) for 1-bromooctane in step 3 of Synthetic Example 9 N-[3-(N,N-dibutylamino)phenyl]acetamide represented by the following formula (C17) was obtained in the same manner as in Step 3 of Synthesis Example 9 except for using . Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C17).

22-B. Synthesis of red dye compound (C-6) by coupling reaction (step 2)
A red dye represented by the following formula (C-6) was prepared in the same manner as in steps 1 and 2 of Synthesis Example 17, except that the compound of formula (C17) was used instead of the compound of formula (C9) as the coupler component solution. A compound (19.6 g, yield 87.9%) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 446 (M ⁺ )).

(Synthesis Example 23)
[Synthesis of red dye compound (C-7)]
A red dye compound (C-7) was produced according to the following scheme.

A red dye represented by the following formula (C-7) was prepared in the same manner as in steps 1 and 2 of Synthesis Example 17, except that the compound of formula (C16) was used instead of the compound of formula (C9) as the coupler component solution. A compound (16.6 g, yield 70.0%) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 474 (M ⁺ )).

(Synthesis Example 24)
[Synthesis of orange dye compound (D-1)]
Orange dye compound (D-1) was produced according to the following scheme.

24-A. Synthesis of coupler compound C18 and preparation of coupler component solution (Step 1)
In the same manner as in Step 4 of Synthesis Example 1, except for using aniline (4.66 g) instead of N-(3-amino-4-methoxyphenyl)octanamide, N,N represented by the following formula (C18) - Dioctylaniline was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C18).

24-B. Preparation of diazo component solution (step 2)
To a mixture of concentrated sulfuric acid (17 g) and 43% nitrosylsulfuric acid (14.7 g), 2,6-dichloro-4-nitroaniline (10.4 g) represented by the following formula (D4) was added at 25 to 30°C. and stirred at the same temperature for 2 hours to obtain a diazo component solution.

24-C. Synthesis of orange dye compound (D-1) by coupling reaction (step 3)
The diazo component solution obtained in step 2 was added to the coupler component solution comprising the compound of formula (C18) obtained in step 1, and triethylamine (20 g) was added appropriately within the range of 0 to 10°C over 2 hours. was added dropwise to carry out the coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. An orange dye compound (23.1 g, yield 86.4%) represented by the following formula (D-1) was obtained. The structure of the orange dye compound was confirmed by LCMS analysis (m/z 535 (M ⁺ )).

(Synthesis Example 25)
[Synthesis of orange dye compound (D-2)]
An orange dye compound (D-2) was produced according to the scheme below.

25-A. Synthesis of coupler compound C19 and preparation of coupler component solution (Step 1)
Synthetic example except using aniline (4.66 g) in place of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromododecane (49.8 g) in place of 1-bromooctane. N,N-didodecylaniline represented by the following formula (C19) was obtained in the same manner as in step 4 of 1. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C19).

25-B. Synthesis of orange dye compound (D-2) by coupling reaction (step 2)
An orange dye represented by the following formula (D-2) was prepared in the same manner as in steps 2 and 3 of Synthesis Example 24, except that the compound of formula (C19) was used instead of the compound of formula (C18) as the coupler component solution. A compound (14.1 g, yield 43.6%) was obtained. The structure of the orange dye compound was confirmed by LCMS analysis (m/z 647 (M ⁺ )).

(Synthesis Example 26)
[Synthesis of orange dye compound (D-3)]
An orange dye compound (D-3) was produced according to the scheme below.

26-A. Synthesis of coupler compound C20 and preparation of coupler component solution (step 1)
Synthesis Example 1 except that aniline (4.66 g) is used instead of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromobutane (27.4 g) is used instead of 1-bromooctane. N,N-dibutylaniline represented by the following formula (C20) was obtained in the same manner as in Step 4 of . Methanol (30 g) was added to the reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C20).

26-B. Synthesis of orange dye compound (D-3) by coupling reaction (step 2)
An orange dye represented by the following formula (D-3) was prepared in the same manner as in steps 2 and 3 of Synthesis Example 24, except that the compound of formula (C20) was used instead of the compound of formula (C18) as the coupler component solution. The compound (10.2 g, 48.2% yield) was obtained. The structure of the orange dye compound was confirmed by LCMS analysis (m/z 423 (M ⁺ )).

(Synthesis Example 27)
[Synthesis of yellow dye compound (G-1)]
A yellow dye compound (G-1) was produced according to the following scheme.

A mixture of 2-hexyldecanoic acid (30.8 g) and toluene (30 g) was added dropwise with a mixture of thionyl chloride (14.3 g) and toluene (20 g). After a mixture of pyridine (9.49 g) and toluene (30 g) was slowly added dropwise to this mixture over 1 hour, the temperature was raised to 110° C. and stirred for 1 hour. After cooling to room temperature, a mixture of 5-amino-anthra[9,1-cd]isothiazol-6-one (25.2 g) and toluene (30 g) was added dropwise. After heating to 110° C. and stirring for 2 hours, the solvent was distilled off under reduced pressure, and methanol (100 g) was added to precipitate a precipitate. This mixture was separated by filtration, washed with methanol and then with water, dried at 60° C. until the water content became 1.0% by mass or less, and a yellow dye compound (36.7 g, Yield 74.7%) was obtained. The structure of the yellow dye compound was confirmed by LCMS analysis (m/z 491 (M ⁺ )).

(Synthesis Example 28)
[Synthesis of yellow dye compound (G-2)]
A yellow dye compound (G-2) was produced according to the following scheme.

n-octanoyl chloride (19.5 g) was added dropwise to a mixture of 5-amino-anthra[9,1-cd]isothiazol-6-one (25.2 g), toluene (120 g) and pyridine (9.49 g) After that, the temperature was raised to 110° C. and the mixture was stirred for 1 hour. After cooling the mixture to room temperature, methanol (150 g) was added to precipitate a precipitate. This mixture was filtered, washed with methanol and dried to obtain a yellow dye compound (31.8 g, yield 83.9%) represented by the following formula (G-2). The structure of the yellow dye compound was confirmed by LCMS analysis (m/z 379 (M ⁺ )).

(Synthesis Example 29)
[Synthesis of purple dye compound (F-1)]
A purple dye compound (F-1) was produced according to the following scheme.

A coupler component solution composed of the compound of formula (C18) is prepared in the same manner as in step 1 of Synthesis Example 24, and a diazo component solution derived from the compound of formula (D2) is prepared in the same manner as in step 4 of Synthesis Example 9. gone. The diazo component solution was added dropwise to the coupler component solution at 0 to 10° C. over 2 hours while appropriately adding triethylamine (35 g) to carry out a coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. A purple dye compound (13.0 g, yield 49.6%) represented by the following formula (F-1) was obtained. The structure of the purple dye compound was confirmed by LCMS analysis (m/z 524 (M ⁺ )).

(Synthesis Example 30)
[Synthesis of orange dye compound (D-4)]
An orange dye compound (D-4) was produced according to the scheme below.

30-A. Preparation of diazo component solution (step 1)
To a mixture of concentrated sulfuric acid (17 g) and 43% nitrosylsulfuric acid (14.7 g), 4-nitroaniline (6.91 g) represented by the following formula (D5) was added within the range of 30 to 35°C, and the mixture was heated at the same temperature. and stirred for 2 hours to obtain a diazo component solution.

30-B. Synthesis of orange dye compound (D-4) by coupling reaction (step 2)
A coupler component solution comprising the compound of formula (C18) was prepared in the same manner as in Step 1 of Synthesis Example 24. The diazo component solution obtained in step 1 was added dropwise to the coupler component solution at a temperature within the range of 0 to 10° C. while adding triethylamine (20 g) appropriately over 1 hour to carry out a coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. An orange dye compound (12.5 g, yield 53.5%) represented by the following formula (D-4) was obtained. The structure of the orange dye compound was confirmed by LCMS analysis (m/z 467 (M ⁺ )).

(Synthesis Example 31)
[Synthesis of orange dye compound (D-5)]
An orange dye compound (D-5) was produced according to the scheme below.

31-A. Preparation of diazo component solution (step 1)
To a mixture of concentrated sulfuric acid (17 g) and 43% nitrosylsulfuric acid (14.7 g), 2,6-dibromo-4-nitroaniline (14.8 g) represented by the following formula (D6) was added at 25 to 30°C. and stirred at the same temperature for 2 hours to obtain a diazo component solution.

31-B. Synthesis of orange dye compound (D-5) by coupling reaction (step 2)
A coupler component solution comprising the compound of formula (C18) was prepared in the same manner as in Step 1 of Synthesis Example 24. The diazo component solution obtained in step 1 was added dropwise to the coupler component solution at a temperature within the range of 0 to 10° C. while adding triethylamine (25 g) appropriately over 1 hour to carry out a coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. An orange dye compound (27.6 g, yield 88.6%) represented by the following formula (D-5) was obtained. The orange dye compound was confirmed to have the following formula (D-5) by LCMS analysis (m/z 623 (M ⁺ )).

(Synthesis Example 32)
[Synthesis of orange dye compound (D-6)]
An orange dye compound (D-6) was produced according to the scheme below.

An orange dye represented by the following formula (D-6) was prepared in the same manner as in steps 1 and 2 of Synthesis Example 31, except that the compound of formula (C20) was used instead of the compound of formula (C18) as the coupler component solution. A compound (22.8 g, yield 89.2%) was obtained. The structure of the orange dye compound was confirmed by LCMS analysis (m/z 511 (M ⁺ )).

(Synthesis Example 33)
[Synthesis of orange dye compound (E-1)]
Orange dye compound (E-1) was produced according to the following scheme.

33-A. Synthesis of Coupler Compound C21 and Preparation of Coupler Component Solution (Step 1)
A mixture of 2-phenyl-1H-indole (9.67 g), triethylamine (7.5 g), DMF (15 g) and 1-bromooctane (11.6 g) was heated to 120°C and kept at the same temperature for 3 hours. By stirring, N-octyl-2-phenylindole represented by the following formula (C21) was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C21).

33-B. Synthesis of orange dye compound (E-1) by coupling reaction (step 2)
A diazo component solution derived from the compound of formula (D4) was prepared in the same manner as in Synthesis Example 24. The diazo component solution was added dropwise to the coupler component solution obtained in step 1 over 1 hour while appropriately adding triethylamine (20 g) within the range of 0 to 10° C. to carry out a coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. An orange dye compound (11.3 g, yield 43.2%) represented by the following formula (E-1) was obtained. The structure of the orange dye compound was confirmed by LCMS analysis (m/z 523 (M ⁺ )).

(Synthesis Example 34)
[Synthesis of orange dye compound (E-2)]
An orange dye compound (E-2) was produced according to the scheme below.

34-A. Synthesis of Coupler Compound C22 and Preparation of Coupler Component Solution (Step 1)
N-butyl-2-phenylindole represented by the following formula (C22) was obtained in the same manner as in Step 1 of Synthesis Example 33, except for using 1-bromobutane (7.53 g) instead of 1-bromooctane. . Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C22).

34-B. Synthesis of orange dye compound (E-2) by coupling reaction (step 2)
An orange dye represented by the following formula (E-2) was prepared in the same manner as in steps 1 and 2 of Synthesis Example 33, except that the compound of formula (C22) was used instead of the compound of formula (C21) as the coupler component solution. A compound (14.5 g, yield 62.1%) was obtained. The structure of the orange dye compound was confirmed by LCMS analysis (m/z 467 (M ⁺ )).

(Synthesis Example 35)
[Synthesis of red dye compound (D-7)]
Red dye compound (D-7) was produced according to the following scheme.

35-A. Preparation of diazo component solution (step 1)
To a mixture of concentrated sulfuric acid (7.5 g), acetic acid (15 g) and 43% nitrosylsulfuric acid (14.9 g), 2-cyano-4-nitroaniline (8.15 g) represented by the following formula (D7) was added 20 to 25 times. C. and stirred for 2 hours at the same temperature to obtain a diazo component solution.

35-B. Synthesis of red dye compound (D-7) by coupling reaction (step 2)
A coupler component solution comprising the compound of formula (C18) was prepared in the same manner as in Synthesis Example 24. The diazo component solution obtained in step 1 was added dropwise to the coupler component solution at a temperature within the range of 0 to 10° C. while adding triethylamine (30 g) appropriately over 1 hour to carry out a coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. A red dye compound (16.9 g, yield 68.9%) represented by the following formula (D-7) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 492 (M ⁺ )).

(Synthesis Example 36)
[Synthesis of purple dye compound (C-8)]
A purple dye compound (C-8) was produced according to the following scheme.

A coupler component solution comprising the compound of formula (C16) is prepared in the same manner as in step 1 of Synthesis Example 16, and a diazo component solution derived from the compound of formula (D1) is prepared in the same manner as in step 5 of Synthesis Example 1. gone. The diazo component solution was added dropwise to the coupler component solution at a temperature within the range of 0 to 10° C. over 2 hours while appropriately adding triethylamine (32 g) to carry out a coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. A purple dye compound (6.14 g, yield 21.8%) represented by the following formula (C-8) was obtained. The structure of the purple dye compound was confirmed to have the following formula (C-8) by LCMS analysis molecular weight (m/z 563 (M ⁺ )).

(Synthesis Example 37)
[Synthesis of purple dye compound (C-9)]
A purple dye compound (C-9) was produced according to the following scheme.

A purple dye compound represented by the following formula (C-9) (12.1 g ). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 731 (M ⁺ )).

(Synthesis Example 38)
[Synthesis of purple dye compound (C-10)]
A purple dye compound (C-10) was produced according to the following scheme.

A mixture of sodium bromide (5.92 g), triethylamine (0.50 g) and DMF (80 g) was stirred for 15 minutes within the range of 35-40°C, cuprous cyanide (5.0 g) was added and the same It was stirred for 15 minutes under warm conditions. Purple dye compound (C-9) (34.3 g) was added to this mixture, and the mixture was heated to 110° C. and stirred for 1 hour. After cooling to 80° C., a mixture of water (190 g) and sodium hypochlorite (18 g) was added, stirred at 70-80° C. for 1 hour, and cooled to room temperature. The product was filtered off from the reaction mixture, washed with water, dried at 60° C. until the water content was 1.0% by mass or less, and a purple dye compound (20.4 g) represented by the following formula (C-10) was obtained. , yield 64.2%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 678 (M ⁺ )).

(Synthesis Example 39)
[Synthesis of purple dye compound (C-11)]
A purple dye compound (C-11) was produced according to the following scheme.

39-A. Preparation of diazo component solution (step 1)
2-bromo-6-cyano-4-nitroaniline (11.1 g) represented by the following formula (D8) was added to a mixture of concentrated sulfuric acid (10.7 g) and acetic acid (28.8 g) within the range of 20 to 25 ° C. added with To this mixture, 43% nitrosylsulfuric acid (15.6 g) was added within the range of 20 to 25°C, and the mixture was stirred at the same temperature for 2 hours to obtain a diazo component solution.

39-B. Synthesis of purple dye compound (C-11) by coupling reaction (step 2)
A coupler component solution comprising the compound of formula (C9) was prepared in the same manner as steps 1 to 3 of Synthesis Example 9. The diazo component solution obtained in step 1 was added dropwise to the coupler component solution at a temperature within the range of 0 to 10° C. while adding triethylamine (20 g) appropriately over 2 hours to carry out a coupling reaction. After stirring for 20 minutes in the range of 0-10°C, the product is filtered off from the reaction mixture, washed with methanol, then water and dried at 60°C until the water content is below 1.0% by weight. A purple dye compound (16.0 g, yield 45.0%) represented by the following formula (C-11) was obtained. The structure of the purple dye compound was confirmed by LCMS analysis (m/z 711 (M ⁺ )).

(Synthesis Example 40)
[Synthesis of purple dye compound (C-12)]
A purple dye compound (C-12) was produced according to the following scheme.

40-A. Synthesis of coupler compound C23 and preparation of coupler component solution (Step 1)
N represented by the following formula (C23) in the same manner as in steps 1 to 3 of Synthesis Example 9, except that 1-bromobutane (27.4 g) is used instead of 1-bromooctane in Step 3 of Synthesis Example 9. -[3-(N,N-dibutylamino)phenyl]octanamide was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C23).

40-B. Synthesis of purple dye compound (C-12) by coupling reaction (step 2)
A purple dye compound represented by the following formula (C-12) ( 5.99 g, 20.0% yield). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 599 (M ⁺ )).

(Synthesis Example 41)
[Synthesis of purple dye compound (C-13)]
A purple dye compound (C-13) was produced according to the following scheme.

A purple dye compound represented by the following formula (C-13) ( 23.5 g, yield 75.0%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 627 (M ⁺ )).

(Synthesis Example 42)
[Synthesis of purple dye compound (C-14)]
A purple dye compound (C-14) was produced according to the following scheme.

A purple dye compound represented by the following formula (C-14) ( 10.8 g, yield 39.8%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 543 (M ⁺ )).

(Synthesis Example 43)
[Synthesis of purple dye compound (C-15)]
A purple dye compound (C-15) was produced according to the following scheme.

In Synthesis Example 38, the following formula (C -15) to obtain a purple dye compound (26.9 g, yield 93.7%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 574 (M ⁺ )).

(Synthesis Example 44)
[Synthesis of purple dye compound (C-16)]
A purple dye compound (C-16) was produced according to the following scheme.

In Synthesis Example 38, the following formula (C -16) was obtained (22.0 g, yield 89.8%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 490 (M ⁺ )).

(Synthesis Example 45)
[Synthesis of yellow dye compound (G-3)]
A yellow dye compound (G-3) was produced according to the following scheme.

In Synthesis Example 28, in the same manner as in Synthesis Example 28 except for using 2-ethylhexanoyl chloride (19.5 g) instead of n-octanoyl chloride, a yellow dye compound represented by the following formula (G-3) (33.1 g, 87.3% yield). The structure of the yellow dye compound was confirmed by LCMS analysis (m/z 379 (M ⁺ )).

(Synthesis Example 46)
[Synthesis of yellow dye compound (G-4)]
A yellow dye compound (G-4) was produced according to the following scheme.

A yellow dye compound represented by the following formula (G-4) (31. 0 g, yield 78.9%). The structure of the yellow dye compound was confirmed by LCMS analysis (m/z 393 (M ⁺ )).

(Synthesis Example 47)
[Synthesis of blue dye compound (B-9)]
A blue dye compound (B-9) was produced according to the following scheme.

A blue dye compound represented by the following formula (B-9) ( 9.12 g, yield 33.0%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 553 (M ⁺ )).

(Synthesis Example 48)
[Synthesis of blue dye compound (B-10)]
A blue dye compound (B-10) was produced according to the following scheme.

48-A. Synthesis of coupler compound C24 and preparation of coupler component solution (Step 1)
In Step 1 of Synthesis Example 9, in the same manner as in Steps 1 to 3 of Synthesis Example 9 except that 2-ethylhexanoyl chloride (34.2 g) is used instead of n-octanoyl chloride, the following formula (C24) N-[3-(N,N-dioctylamino)phenyl]-2-ethylhexanamide represented by was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C24).

48-B. Synthesis of blue dye compound (B-10) by coupling reaction (step 2)
A blue dye represented by the following formula (B-10) was prepared in the same manner as in steps 4 and 5 of Synthesis Example 9, except that the compound of formula (C24) was used instead of the compound of formula (C9) as the coupler component solution. A compound (19.0 g, yield 57.1%) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 665 (M ⁺ )).

(Synthesis Example 49)
[Synthesis of orange dye compound (D-8)]
An orange dye compound (D-8) was produced according to the scheme below.

An orange dye compound represented by the following formula (D-8) was prepared in the same manner as in Synthesis Example 24 except that N,N-diethylaniline (7.45 g) was used instead of the compound of formula (C18) as the coupler compound. (15.2 g, 82.8% yield). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 367 (M ⁺ )).

(Synthesis Example 50)
[Synthesis of orange dye compound (D-9)]
An orange dye compound (D-9) was produced according to the scheme below.

An orange dye compound represented by the following formula (D-9) was prepared in the same manner as in Synthesis Example 31 except that N,N-diethylaniline (7.45 g) was used instead of the compound of formula (C18) as the coupler compound. (18.2 g, 80.0% yield). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 455 (M ⁺ )).

(Synthesis Example 51)
[Synthesis of orange dye compound (D-10)]
An orange dye compound (D-10) was produced according to the scheme below.

An orange dye compound represented by the following formula (D-10) was prepared in the same manner as in Synthesis Example 30, except that N,N-diethylaniline (7.45 g) was used instead of the compound of formula (C18) as the coupler compound. (9.35 g, 62.5% yield). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 299 (M ⁺ )).

(Synthesis Example 52)
[Synthesis of orange dye compound (D-11)]
An orange dye compound (D-11) was produced according to the scheme below.

52-A. Synthesis of Coupler Compound C25 and Preparation of Coupler Component Solution (Step 1)
A mixture of aniline (18.6 g), acetic acid (50 g), cuprous chloride (1.3 g) and acrylonitrile (20 g) was heated to 110° C. and stirred for 3 hours. After cooling to room temperature, toluene (100 g) and 10% aqueous sodium carbonate solution (150 g) were added to extract the organic layer. The extract was washed with saturated brine, and the solvent was distilled off under reduced pressure to obtain N-cyanoethylaniline represented by the following formula (C25a) (28.7 g, yield 98.2%) as a crude product. rice field.

(Step 2)
A mixture of N-cyanoethylaniline (28.7 g) obtained in the above step, triethylamine (15 g), DMF (15 g) and 1-bromooctane (14.5 g) was heated to 120° C. and By stirring for hours, N-cyanoethyl-N-octylaniline represented by the following formula (C25) was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C25).

52-B. Synthesis of orange dye compound (D-11) by coupling reaction (step 3)
An orange dye compound represented by the following formula (D-11) (10.6 g , yield 52.0%). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 408 (M ⁺ )).

(Synthesis Example 53)
[Synthesis of red dye compound (C-17)]
A red dye compound (C-17) was produced according to the following scheme.

53-A. Synthesis of Coupler Compound C26 and Preparation of Coupler Component Solution (Step 1)
except using 3′-aminoacetanilide (7.50 g) instead of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromoethane (27.3 g) instead of 1-bromooctane was carried out in the same manner as in Step 4 of Synthesis Example 1 to obtain N-[3-(N,N-diethylamino)phenyl]acetamide represented by the following formula (C26). Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C26).

53-B. Synthesis of red dye compound (C-17) by coupling reaction (step 2)
A red dye compound represented by the following formula (C-17) (11.8 g, Yield 60.5%) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 390 (M ⁺ )).

(Synthesis Example 54)
[Synthesis of purple dye compound (F-2)]
A purple dye compound (F-2) was produced according to the following scheme.

A purple dye compound represented by the following formula (F-2) was prepared in the same manner as in Synthesis Example 29, except that N,N-diethylaniline (7.45 g) was used instead of the compound of formula (C18) as the coupler compound. (10.6 g, 59.6% yield) was obtained. The structure of the purple dye compound was confirmed by LCMS analysis (m/z 356 (M ⁺ )).

(Synthesis Example 55)
[Synthesis of blue dye compound (B-11)]
A blue dye compound (B-11) was produced according to the following scheme.

A blue dye compound represented by the following formula (B-11) was prepared in the same manner as in steps 4 and 5 of Synthesis Example 9, except that the compound of formula (C26) was used instead of the compound of formula (C9) as the coupler compound. (11.9 g, 57.6% yield). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 413 (M ⁺ )).

(Synthesis Example 56)
[Synthesis of blue dye compound (A-9)]
A blue dye compound (A-9) was produced according to the following scheme.

56-A. Synthesis of Coupler Compound C27 and Preparation of Coupler Component Solution (Step 1)
N-(3-amino-4-methoxyphenyl)octanamide (13.2 g) obtained in Step 3 of Synthesis Example 1, acetic acid (15 g), cuprous chloride (0.32 g), acrylonitrile (5.0 g) ) was heated to 110° C. and stirred for 3 hours. After cooling to room temperature, toluene (50 g) and 10% aqueous sodium carbonate solution (75 g) were added to extract the organic layer. This extract was washed with saturated brine, and the solvent was evaporated under reduced pressure to give N-(3-cyanoethylamino-4-methoxyphenyl)octanamide (9.05 g, yield) represented by the following formula (C27a): 57.0%) was obtained as a crude product.

(Step 2)
A mixture of N-(3-cyanoethylamino-4-methoxyphenyl)octanamide (15.9 g) obtained in the above step, DMF (15 g) and diethyl sulfate (11.6 g) was heated to 90° C. and By stirring at room temperature for 2 hours, N-(3-N-ethyl-N-cyanoethylamino-4-methoxyphenyl)octanamide represented by the following formula (C27) was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C27).

56-B. Synthesis of blue dye compound (A-9) by coupling reaction (step 3)
A blue dye represented by the following formula (A-9) was prepared in the same manner as in steps 5 and 6 of Synthesis Example 1, except that the compound of formula (C27) was used instead of the compound of formula (C1) as the coupler component solution. The compound (9.70 g, 31.4% yield) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 618 (M ⁺ )).

(Synthesis Example 57)
[Synthesis of blue dye compound (A-10)]
A blue dye compound (A-10) was produced according to the following scheme.

57-A. Synthesis of coupler compound C28 and preparation of coupler component solution (Step 1)
N-(3-cyanoethylamino-4-methoxyphenyl)octanamide (15.9 g) obtained in Step 1 of Synthesis Example 56, DMF (20 g), triethylamine (12.6 g) and 1-bromooctane (29. 0 g) was heated to 120° C. and stirred for 8 hours to obtain N-(3-N-octyl-N-cyanoethylamino-4-methoxyphenyl) octanamide represented by the following formula (C28). . Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution represented by formula (C28).

57-B. Synthesis of blue dye compound (A-10) by coupling reaction (step 2)
A blue dye represented by the following formula (A-10) was prepared in the same manner as in steps 5 and 6 of Synthesis Example 1, except that the compound of formula (C28) was used instead of the compound of formula (C1) as the coupler component solution. The compound (5.52 g, 15.7% yield) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 702 (M ⁺ )).

(Synthesis Example 58)
[Synthesis of blue dye compound (A-11)]
A blue dye compound (A-11) was produced according to the following scheme.

58-A. Synthesis of coupler compound C29 and preparation of coupler component solution (Step 1)
N-(3-amino-4-methoxyphenyl)octanamide (13.2 g) obtained in Step 3 of Synthesis Example 1, DMF (15 g), triethylamine (15 g) and 2-bromoethyl methyl ether (27.8 g) ) was heated to 110° C. and stirred for 8 hours to give N-[3-N,N-(2-dimethoxyethyl)amino-4-methoxyphenyl]octanamide represented by the following formula (C29). Obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution represented by formula (C29).

(Step 2)
A blue dye represented by the following formula (A-11) was prepared in the same manner as in steps 5 and 6 of Synthesis Example 1, except that the compound of formula (C29) was used instead of the compound of formula (C1) as the coupler component solution. The compound (6.58 g, 20.2% yield) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 653 (M ⁺ )).

(Synthesis Example 59)
[Synthesis of blue dye compound (A-12)]
A blue dye compound (A-12) was produced according to the following scheme.

59-A. Synthesis of coupler compound C30 and preparation of coupler component solution (Step 1)
N-(3-amino-4-methoxyphenyl)acetamide (purchased commercially) (9.0 g) instead of N-(3-amino-4-methoxyphenyl)octanamide, 1-bromooctane N-[3-(N,N-dihexylamino)-4- represented by the following formula (C30) was prepared in the same manner as in Step 4 of Synthesis Example 1, except that 1-bromobutane (27.4 g) was used instead. Methoxyphenyl]acetamide was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution represented by the formula (C30).

59-B. Synthesis of blue dye compound (A-12) by coupling reaction (step 2)
A blue dye represented by the following formula (A-12) was prepared in the same manner as in steps 5 and 6 of Synthesis Example 1, except that the compound of formula (C30) was used instead of the compound of formula (C1) as the coupler component solution. A compound (14.1 g, yield 49.9%) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 565 (M ⁺ )).

(Synthesis Example 60)
[Synthesis of blue dye compound (A-13)]
A blue dye compound (A-13) was produced according to the following scheme.

60-A. Synthesis of Coupler Compound C31 and Preparation of Coupler Component Solution (Step 1)
N-(3-amino-4-methoxyphenyl)acetamide (purchased commercially) (9.0 g) instead of N-(3-amino-4-methoxyphenyl)octanamide, 1-bromooctane N-[3-(N,N-dihexylamino)-4 represented by the following formula (C31) was prepared in the same manner as in Step 4 of Synthesis Example 1, except that 1-bromohexane (33.0 g) was used instead. -Methoxyphenyl]acetamide. Methanol (30 g) was added to the reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C31).

60-B. Synthesis of blue dye compound (A-13) by coupling reaction (step 2)
A blue dye represented by the following formula (A-13) was prepared in the same manner as in steps 5 and 6 of Synthesis Example 1, except that the compound of formula (C31) was used instead of the compound of formula (C1) as the coupler component solution. The compound (10.7 g, 34.5% yield) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 621 (M ⁺ )).

(Synthesis Example 61)
[Synthesis of blue dye compound (A-14)]
A blue dye compound (A-14) was produced according to the following scheme.

61-A. Synthesis of coupler compound C32 and preparation of coupler component solution (Step 1)
Except for using valeryl chloride (25.3 g) instead of n-octanoyl chloride in step 1 of Synthesis Example 1 and using 1-bromoethane (27.3 g) instead of 1-bromooctane in step 4. was carried out in the same manner as in steps 1 to 4 of Synthesis Example 1 to obtain N-[3-(N,N-diethylamino)-4-methoxyphenyl]pentanamide represented by the following formula (C32). Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C32).

61-B. Synthesis of blue dye compound (A-14) by coupling reaction (step 2)
A blue dye represented by the following formula (A-14) was prepared in the same manner as in steps 5 and 6 of Synthesis Example 1, except that the compound of formula (C32) was used instead of the compound of formula (C1) as the coupler component solution. A compound (24.1 g, yield 87.5%) was obtained. The structure of the blue dye compound was confirmed by LCMS analysis (m/z 551 (M ⁺ )).

(Synthesis Example 62)
[Synthesis of blue dye compound (A-15)]
A blue dye compound (A-15) was produced according to the following scheme.

62-A. Synthesis of coupler compound C33 and preparation of coupler component solution (Step 1)
In Step 1 of Synthesis Example 1, lauroyl chloride (45.9 g) is used instead of n-octanoyl chloride, and 1-bromoethane (27.3 g) is used instead of 1-bromooctane in Step 4. In the same manner as in steps 1 to 4 of Synthesis Example 1, N-[3-(N,N-diethylamino)-4-methoxyphenyl]dodecanamide represented by the following formula (C33) was obtained. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C33).

62-B. Synthesis of blue dye compound (A-15) by coupling reaction (step 2)
A blue dye compound represented by the following formula (A-15) (26. 8 g, yield 82.6%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 649 (M ⁺ )).

(Synthesis Example 63)
[Synthesis of red dye compound (C-18)]
A red dye compound (C-18) was produced according to the following scheme.

63-A. Synthesis of Coupler Compound C34 and Preparation of Coupler Component Solution (Step 1)
In step 3 of Synthesis Example 9, 1-bromohexane (33.0 g) was substituted for 1-bromooctane, 3′-aminoacetanilide (7.50 g) was substituted for N-(3-aminophenyl)octanamide, ) to obtain N-[3-(N,N-dihexylamino)phenyl]acetamide represented by the following formula (C34) in the same manner as in Step 3 of Synthesis Example 9, except that ) was used. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C34).

63-B. Synthesis of red dye compound (C-18) by coupling reaction (step 2)
A red dye compound represented by the following formula (C-18) (20.1 g , yield 80.1%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 502 (M ⁺ )).

(Synthesis Example 64)
[Synthesis of orange dye compound (D-12)]
An orange dye compound (D-12) was produced according to the scheme below.

64-A. Synthesis of coupler compound C35 and preparation of coupler component solution (Step 1)
Synthetic example except using aniline (4.66 g) instead of N-(3-amino-4-methoxyphenyl)octanamide and using 1-bromohexane (33.0 g) instead of 1-bromooctane N,N-dihexylaniline represented by the following formula (C35) was obtained in the same manner as in step 4 of 1. Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C35).

64-B. Synthesis of orange dye compound (D-12) by coupling reaction (step 2)
An orange dye compound represented by the following formula (D-12) (13.5 g , yield 56.4%). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 479 (M ⁺ )).

(Synthesis Example 65)
[Synthesis of orange dye compound (D-13)]
An orange dye compound (D-13) was produced according to the scheme below.

An orange dye compound represented by the following formula (D-13) (16.4 g , yield 79.8%). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 411 (M ⁺ )).

(Synthesis Example 66)
[Synthesis of blue dye compound (A-16)]
A blue dye compound (A-16) was produced according to the following scheme.

66-A. Synthesis of coupler compound C8 and preparation of coupler component solution (step 1)
Synthesis Example 1 except that in step 1 of Synthesis Example 1, 4-butoxyaniline (33.0 g) is used instead of p-anisidine and propionyl chloride (19.4 g) is used instead of n-octanoyl chloride. N-[3-(N,N-dioctylamino)-4-butoxyphenyl]propanamide represented by the following formula (C36) was obtained in the same manner as in steps 1 to 4 of . Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution consisting of the compound of formula (C36).

66-B. Synthesis of blue dye compound (A-16) by coupling reaction (step 2)
The following formula (A-16 ) was obtained (6.45 g, yield 17.6%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 733 (M ⁺ )).

(Synthesis Example 67)
[Synthesis of red dye compound (C-19)]
A red dye compound (C-19) was produced according to the following scheme.

67-A. Synthesis of Coupler Compound C37 and Preparation of Coupler Component Solution (Step 1)
Using propionyl chloride (19.4 g) in place of n-octanoyl chloride in Step 1 of Synthesis Example 9, and 1-bromohexane (33.0 g) in place of 1-bromooctane in Step 3 of Synthesis Example 9. N-[3-(N,N-dihexylamino)phenyl]propanamide represented by the following formula (C37) was obtained in the same manner as in Steps 1 to 3 of Synthesis Example 9 except for using . Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C37).

67-B. Synthesis of red dye compound (C-19) by coupling reaction (step 2)
The following formula (C-19 ) was obtained (17.6 g, yield 68.2%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 516 (M ⁺ )).

(Synthesis Example 68)
[Synthesis of red dye compound (C-20)]
A red dye compound (C-20) was produced according to the following scheme.

A red dye represented by the following formula (C-20) was prepared in the same manner as in steps 1 and 2 of Synthesis Example 30, except that the compound of formula (C12) was used instead of the compound of formula (C18) as the coupler component solution. A compound (23.0 g, yield 87.7%) was obtained. The structure of the red dye compound was confirmed by LCMS analysis (m/z 524 (M ⁺ )).

(Synthesis Example 69)
[Synthesis of blue dye compound (A-17)]
A blue dye compound (A-17) was produced according to the following scheme.

69-A. Synthesis of coupler compound C38 and preparation of coupler component solution (Step 1)
Using valeryl chloride (25.3 g) instead of n-octanoyl chloride in step 1 of Synthesis Example 1, and using 1-bromohexane (33.0 g) instead of 1-bromooctane in step 4 N-[3-(N,N-dihexylamino)-4-methoxyphenyl]pentanamide represented by the following formula (C38) was obtained in the same manner as in Steps 1 to 4 of Synthesis Example 1, except that: Methanol (30 g) was added to this reaction mixture and cooled to 5° C. to obtain a coupler component solution comprising the compound of formula (C38).

69-B. Synthesis of blue dye compound (A-17) by coupling reaction (step 2)
The following formula (A-17 ) was obtained (15.3 g, yield 48.4%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 663 (M ⁺ )).

Structural formulas of the dye compounds described in Synthesis Examples and conventional dye compounds are shown in Tables 3-9.

<Production example of dye composition>
Dye compositions of the compounds listed in Tables 3-9 were prepared for waterborne dyeing. A production example is shown below. In this production example, the dye composition is in the form of liquid aqueous dispersion or powder. Specifically, Dye Composition Production Examples 1 to 105 are production examples of liquid dye compositions, and Dye Composition Production Examples 106 to 141 are production examples of powder dye compositions. The volume median particle size of the compound in the dye composition was measured using a dynamic light scattering particle size distribution analyzer LB-500 manufactured by Horiba, Ltd.

(Dye composition production example 1)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -5 dye composition was obtained.

(Dye composition production example 2)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 76 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and a compound A having a volume median particle diameter of 0.20 μm and a concentration of 20% by mass is obtained. A -5 dye composition was obtained.

(Dye composition production example 3)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.16 μm and a concentration of 20% by mass is obtained. A -5 dye composition was obtained.

(Dye Composition Production Example 4)
30 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 50 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.19 μm and a concentration of 20% by mass is obtained. A -5 dye composition was obtained.

(Dye composition production example 5)
Dissolve 20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant in 50 g of water, then dissolve 10 g of propylene glycol. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.19 μm and a concentration of 20% by mass is obtained. A -5 dye composition was obtained.

(Dye composition production example 6)
20 g of tristyrenated phenol-ethylene oxide 50 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.19 μm and a concentration of 20% by mass is obtained. A -5 dye composition was obtained.

(Dye Composition Production Example 7)
20 g of tribenzylphenol-ethylene oxide 23 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.15 μm and a concentration of 20% by mass is obtained. A -5 dye composition was obtained.

(Dye Composition Production Example 8)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.12 μm and a concentration of 20% by mass is obtained. A -3 dye composition was obtained.

(Dye composition production example 9)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct and 10 g of a tristyrenated phenol-ethylene oxide 50 mol adduct as dispersants are dissolved in 60 g of water. 20 g of the compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 10)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct and 10 g of tribenzylphenol-ethylene oxide 23 mol adduct as dispersants are dissolved in 60 g of water. 20 g of the compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.12 μm and a concentration of 20% by mass is obtained. A -3 dye composition was obtained.

(Dye Composition Production Example 11)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of sodium lignosulfonate are dissolved in 60 g of water. 20 g of the compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.16 μm and a concentration of 20% by mass is obtained. A -3 dye composition was obtained.

(Dye Composition Production Example 12)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct and 10 g of a tristyrenated phenol-ethylene oxide 29 mol adduct sulfate ester sodium salt are dissolved in 60 g of water. 20 g of the compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.15 μm and a concentration of 20% by mass is obtained. A -3 dye composition was obtained.

(Dye Composition Production Example 13)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound A-1 obtained in Synthesis Example 1 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.27 μm and a concentration of 20% by mass was obtained. A -1 dye composition was obtained.

(Dye Composition Production Example 14)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound B-4 obtained in Synthesis Example 12 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 15)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water, and then 10 g of propylene glycol is dissolved. 20 g of the compound B-4 obtained in Synthesis Example 12 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 16)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 17)
20 g of tristyrenated phenol-ethylene oxide 50 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 18)
20 g of tribenzylphenol-ethylene oxide 23 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm. 3 dye compositions were obtained.

(Dye Composition Production Example 19)
Dissolve 20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant in 50 g of water, then dissolve 10 g of propylene glycol. 20 g of the compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 20)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound B-1 obtained in Synthesis Example 9 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 21)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound B-10 obtained in Synthesis Example 48 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and the volume median particle diameter is 0.24 μm. 10 dye compositions were obtained.

(Dye Composition Production Example 22)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant are dissolved in 76 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 23)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 24)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and the volume median particle diameter is 0.22 μm. A four-dye composition was obtained.

(Dye Composition Production Example 25)
30 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 50 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and the volume median particle diameter is 0.24 μm. A four-dye composition was obtained.

(Dye Composition Production Example 26)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant are dissolved in 60 g of water, and then 10 g of diethylene glycol are dissolved. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and the volume median particle diameter is 0.20 μm. A four-dye composition was obtained.

(Dye Composition Production Example 27)
20 g of tristyrenated phenol-ethylene oxide 50 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 28)
20 g of tobenzylphenol-ethylene oxide 23 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 29)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 30)
20 g of tristyrenated phenol-ethylene oxide 50 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 31)
20 g of tobenzylphenol-ethylene oxide 23 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 32)
Dissolve 20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant in 50 g of water, then dissolve 10 g of ethylene glycol. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 33)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound C-1 obtained in Synthesis Example 17 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 34)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound D-3 obtained in Synthesis Example 26 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 35)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant are dissolved in 60 g of water, and then 10 g of dipropylene glycol are dissolved. 20 g of the compound D-3 obtained in Synthesis Example 26 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 36)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound D-1 obtained in Synthesis Example 24 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and the volume median particle diameter is 0.27 μm. 1 dye composition was obtained.

(Dye Composition Production Example 37)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound D-6 obtained in Synthesis Example 32 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -6 dye composition was obtained.

(Dye Composition Production Example 38)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water, and then 10 g of ethylene glycol is dissolved. 20 g of the compound D-6 obtained in Synthesis Example 32 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -6 dye composition was obtained.

(Dye Composition Production Example 39)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound D-5 obtained in Synthesis Example 31 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -5 dye composition was obtained.

(Dye Composition Production Example 40)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 41)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant are dissolved in 76 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 42)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 43)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water, and then 10 g of propylene glycol is dissolved. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 44)
10 g of a distyrenated phenol-ethylene oxide 58 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 45)
10 g of tristyrenated phenol-ethylene oxide 50 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 46)
10 g of tribenzylphenol-ethylene oxide 23 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 47)
10 g of tribenzylphenol-ethylene oxide 40 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 48)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 70 g of water. 20 g of the compound G-1 obtained in Synthesis Example 27 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 49)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant is dissolved in 60 g of water, and then 10 g of polyethylene glycol (average molecular weight: 400) is dissolved. 20 g of the compound G-1 obtained in Synthesis Example 27 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 50)
20 g of a formalin condensate of sodium naphthalenesulfonate as a dispersant is dissolved in 60 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 51)
20 g of sodium lignosulfonate as a dispersant are dissolved in 60 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 52)
20 g of sulfate ester sodium salt of tristyrenated phenol-ethylene oxide 29 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 53)
20 g of a formalin condensate of sodium naphthalenesulfonate as a dispersant is dissolved in 60 g of water. 20 g of the compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 54)
20 g of sodium lignosulfonate as a dispersant are dissolved in 60 g of water. 20 g of the compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 55)
20 g of sulfate ester sodium salt of tristyrenated phenol-ethylene oxide 29 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 56)
20 g of a formalin condensate of sodium naphthalenesulfonate as a dispersant is dissolved in 60 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, it was not possible to disperse fine particles.

(Dye Composition Production Example 57)
20 g of a formalin condensate of sodium creosote oil sulfonate as a dispersant is dissolved in 60 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, it was not possible to disperse fine particles.

(Dye Composition Production Example 58)
20 g of sodium lignosulfonate as a dispersant are dissolved in 60 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 59)
20 g of a formalin condensate of sodium naphthalenesulfonate as a dispersant is dissolved in 60 g of water. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, it was not possible to disperse fine particles.

(Dye Composition Production Example 60)
20 g of a formalin condensate of sodium creosote oil sulfonate as a dispersant is dissolved in 60 g of water. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, it was not possible to disperse fine particles.

(Dye Composition Production Example 61)
20 g of sodium lignosulfonate as a dispersant are dissolved in 60 g of water. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 62)
20 g of sulfate ester sodium salt of tristyrenated phenol-ethylene oxide 29 mol adduct as a dispersant is dissolved in 60 g of water. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 63)
10 g of formalin condensate of sodium creosote oil sulfonate as a dispersant and 10 g of sodium lignin sulfonate are dissolved in 60 g of water. 20 g of the compound D-1 obtained in Synthesis Example 24 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 64)
20 g of a formalin condensate of sodium naphthalenesulfonate as a dispersant is dissolved in 60 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, it was not possible to disperse fine particles.

(Dye Composition Production Example 65)
20 g of a formalin condensate of sodium methylnaphthalenesulfonate as a dispersant is dissolved in 60 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, it was not possible to disperse fine particles.

(Dye Composition Production Example 66)
20 g of sodium lignosulfonate as a dispersant are dissolved in 60 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, it was not possible to disperse fine particles.

(Dye Composition Production Example 67)
10 g of formalin condensate of sodium naphthalenesulfonate as a dispersant and 10 g of sodium lignosulfonate are dissolved in 60 g of water. 20 g of the compound G-1 obtained in Synthesis Example 27 was added thereto and stirred to prepare an aqueous slurry. Using 200 g of glass beads with a diameter of 0.3 mm, fine particle dispersion treatment was attempted on this water-based slurry by a vertical bead mill. However, the dye composition could not be obtained because it could not be dispersed into fine particles.

(Dye Composition Production Example 68)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of the compound A-13 obtained in Synthesis Example 60 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.15 μm and a concentration of 20% by mass is obtained. A -13 dye composition was obtained.

(Dye Composition Production Example 69)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of the compound A-17 obtained in Synthesis Example 69 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -17 dye composition was obtained.

(Dye Composition Production Example 70)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of the compound A-2 obtained in Synthesis Example 2 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.19 μm and a concentration of 20% by mass is obtained. A -2 dye composition was obtained.

(Dye Composition Production Example 71)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of the compound A-16 obtained in Synthesis Example 66 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -16 dye composition was obtained.

(Dye Composition Production Example 72)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of the compound B-2 obtained in Synthesis Example 10 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -2 dye composition was obtained.

(Dye Composition Production Example 73)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of the compound C-19 obtained in Synthesis Example 67 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -19 dye composition was obtained.

(Dye Composition Production Example 74)
20 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of the compound C-20 obtained in Synthesis Example 68 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -20 dye composition was obtained.

(Dye Composition Production Example 75)
10 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant was dissolved in 70 g of water. 20 g of the compound D-13 obtained in Synthesis Example 65 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 20 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -13 dye composition was obtained.

(Dye Composition Production Example 76)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound A-13 obtained in Synthesis Example 60 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.16 μm and a concentration of 20% by mass was obtained. A -13 dye composition was obtained.

(Dye Composition Production Example 77)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -5 dye composition was obtained.

(Dye Composition Production Example 78)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.15 μm and a concentration of 20% by mass was obtained. A -5 dye composition was obtained.

(Dye Composition Production Example 79)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.15 μm and a concentration of 20% by mass was obtained. A -3 dye composition was obtained.

(Dye Composition Production Example 80)
4 g of a distyrenated phenol-ethylene oxide 58 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.15 μm and a concentration of 20% by mass was obtained. A -3 dye composition was obtained.

(Dye Composition Production Example 81)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound A-2 obtained in Synthesis Example 2 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours using a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -2 dye composition was obtained.

(Dye Composition Production Example 82)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (360 mol)-oxypropylene (70 mol) copolymer were dissolved in 64 g of water. 20 g of the compound A-4 obtained in Synthesis Example 4 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours using a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 83)
8 g of a distyrenated phenol-ethylene oxide 58 mol adduct as a dispersant and 8 g of an oxyethylene (360 mol)-oxypropylene (70 mol) copolymer were dissolved in 64 g of water. 20 g of the compound A-1 obtained in Synthesis Example 1 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound A having a volume median particle diameter of 0.20 μm and a concentration of 20% by mass is obtained. A -1 dye composition was obtained.

(Dye Composition Production Example 84)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound B-4 obtained in Synthesis Example 12 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 85)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 86)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound B-2 obtained in Synthesis Example 10 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -2 dye composition was obtained.

(Dye Composition Production Example 87)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound B-2 obtained in Synthesis Example 10 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -2 dye composition was obtained.

(Dye Composition Production Example 88)
8 g of a distyrenated phenol-ethylene oxide 58 mol adduct as a dispersant and 8 g of an oxyethylene (360 mol)-oxypropylene (70 mol) copolymer were dissolved in 64 g of water. 20 g of the compound B-1 obtained in Synthesis Example 9 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 89)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound B-10 obtained in Synthesis Example 48 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -10 dye composition was obtained.

(Dye Composition Production Example 90)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours using a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 91)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -4 dye composition was obtained.

(Dye Composition Production Example 92)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 93)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -3 dye composition was obtained.

(Dye Composition Production Example 94)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound C-2 obtained in Synthesis Example 18 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours using a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -2 dye composition was obtained.

(Dye Composition Production Example 95)
8 g of tristyrenated phenol-ethylene oxide 50 mol adduct and 8 g of oxyethylene (300 mol)-oxypropylene (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of the compound C-1 obtained in Synthesis Example 17 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 96)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound C-20 obtained in Synthesis Example 68 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -20 dye composition was obtained.

(Dye Composition Production Example 97)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (160 mol)-oxypropylene (60 mol) copolymer were dissolved in 64 g of water. 20 g of the compound D-3 obtained in Synthesis Example 26 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and a compound D having a volume median particle diameter of 0.14 μm and a concentration of 20% by mass is obtained. A -3 dye composition was obtained.

(Dye Composition Production Example 98)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound D-1 obtained in Synthesis Example 24 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 99)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (160 mol)-oxypropylene (60 mol) copolymer were dissolved in 64 g of water. 20 g of the compound D-6 obtained in Synthesis Example 32 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and a compound D having a volume median particle diameter of 0.14 μm and a concentration of 20% by mass is obtained. A -6 dye composition was obtained.

(Dye Composition Production Example 100)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound D-5 obtained in Synthesis Example 31 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound D having a volume median particle diameter of 0.24 μm and a concentration of 20% by mass is obtained. A -5 dye composition was obtained.

(Dye Composition Production Example 101)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound D-13 obtained in Synthesis Example 65 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound D having a volume median particle diameter of 0.18 μm and a concentration of 20% by mass is obtained. A -13 dye composition was obtained.

(Dye Composition Production Example 102)
4 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 10 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 66 g of water. 20 g of the compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry is subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm, and compound D having a volume median particle diameter of 0.20 μm and a concentration of 20% by mass is obtained. A -4 dye composition was obtained.

(Dye Composition Production Example 103)
8 g of tribenzylphenol-ethylene oxide 40 mol adduct and 8 g of oxyethylene (300 mol)-oxypropylene (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of the compound E-1 obtained in Synthesis Example 33 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 104)
8 g of tribenzylphenol-ethylene oxide 23 mol adduct and 8 g of oxyethylene (300 mol)-oxypropylene (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of Compound F-1 obtained in Synthesis Example 29 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours using a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 105)
8 g of a distyrenated phenol-ethylene oxide 24 mol adduct as a dispersant and 8 g of an oxyethylene (300 mol)-oxypropylene (55 mol) copolymer were dissolved in 64 g of water. 20 g of the compound G-1 obtained in Synthesis Example 27 was added thereto and stirred to prepare an aqueous slurry. This water-based slurry was subjected to fine particle dispersion treatment for 24 hours in a vertical bead mill using 200 g of glass beads having a diameter of 0.3 mm. A -1 dye composition was obtained.

(Dye Composition Production Example 106)
33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound A-13 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 76 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound A-13 having a concentration of 20% by mass.

(Dye Composition Production Example 107)
33 g of a formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound A-5 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 77 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound A-5 having a concentration of 20% by mass.

(Dye Composition Production Example 108)
33 g of a formalin condensate of sodium methylnaphthalenesulfonate and 17 g of water were added to 50 g of the compound A-5 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 77 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound A-5 having a concentration of 20% by mass.

(Dye Composition Production Example 109)
33 g of a formalin condensate of sodium creosote oil sulfonate and 17 g of water were added to 50 g of the compound A-5 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 77 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound A-5 having a concentration of 20% by mass.

(Dye Composition Production Example 110)
33 g of sodium ligninsulfonate and 17 g of water were added to 50 g of the compound A-5 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 77 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound A-5 having a concentration of 20% by mass.

(Dye Composition Production Example 111)
33 g of a formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound A-3 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 79, and the mixture was stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound A-3 having a concentration of 20% by mass.

(Dye Composition Production Example 112)
33 g of a formalin condensate of sodium methylnaphthalenesulfonate and 17 g of water were added to 50 g of the compound A-3 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 79, and the mixture was stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound A-3 having a concentration of 20% by mass.

(Dye Composition Production Example 113)
33 g of a formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound A-2 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 81 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound A-2 having a concentration of 20% by mass.

(Dye Composition Production Example 114)
32 g of a formalin condensate of sodium naphthalenesulfonate and 18 g of water were added to 50 g of the compound B-3 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 85 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound B-3 having a concentration of 20% by mass.

(Dye Composition Production Example 115)
32 g of a formalin condensate of sodium naphthalenesulfonate and 18 g of water were added to 50 g of the compound B-2 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 87 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound B-2 having a concentration of 20% by mass.

(Dye Composition Production Example 116)
32 g of a formalin condensate of sodium methylnaphthalenesulfonate and 18 g of water were added to 50 g of the compound B-2 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 87 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound B-2 having a concentration of 20% by mass.

(Dye Composition Production Example 117)
To 50 g of the compound B-2 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 87, 32 g of sodium ligninsulfonate and 18 g of water were added and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound B-2 having a concentration of 20% by mass.

(Dye Composition Production Example 118)
32 g of a formalin condensate of sodium naphthalenesulfonate and 18 g of water were added to 50 g of the compound B-1 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 88, and the mixture was stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound B-1 having a concentration of 20% by mass.

(Dye Composition Production Example 119)
32 g of formalin condensate of sodium naphthalenesulfonate and 18 g of water were added to 50 g of the compound B-10 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 89 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound B-10 having a concentration of 20% by mass.

(Dye Composition Production Example 120)
33 g of a formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound C-4 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 90 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound C-4 having a concentration of 20% by mass.

(Dye Composition Production Example 121)
33 g of a formalin condensate of sodium methylnaphthalenesulfonate and 17 g of water were added to 50 g of the compound C-4 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 90 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound C-4 having a concentration of 20% by mass.

(Dye Composition Production Example 122)
33 g of a formalin condensate of sodium creosote oil sulfonate and 17 g of water were added to 50 g of the compound C-4 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 90 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound C-4 having a concentration of 20% by mass.

(Dye Composition Production Example 123)
To 50 g of the compound C-4 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 90, 33 g of sodium ligninsulfonate and 17 g of water were added and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound C-4 having a concentration of 20% by mass.

(Dye Composition Production Example 124)
33 g of a formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound C-3 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 92 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound C-3 having a concentration of 20% by mass.

(Dye Composition Production Example 125)
33 g of a formalin condensate of sodium methylnaphthalenesulfonate and 17 g of water were added to 50 g of the compound C-3 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 92 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound C-3 having a concentration of 20% by mass.

(Dye Composition Production Example 126)
33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound C-20 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 96 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound C-20 having a concentration of 20% by mass.

(Dye Composition Production Example 127)
33 g of a formalin condensate of sodium creosote oil sulfonate and 17 g of water were added to 50 g of the compound C-20 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 96 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound C-20 having a concentration of 20% by mass.

(Dye Composition Production Example 128)
32 g of a formalin condensate of sodium naphthalenesulfonate and 18 g of water were added to 50 g of the compound D-1 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 98 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound D-1 having a concentration of 20% by mass.

(Dye Composition Production Example 129)
32 g of a formalin condensate of sodium methylnaphthalenesulfonate and 18 g of water were added to 50 g of the compound D-1 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 98, and the mixture was stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound D-1 having a concentration of 20% by mass.

(Dye Composition Production Example 130)
32 g of sodium ligninsulfonate and 18 g of water were added to 50 g of the compound D-1 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 98 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound D-1 having a concentration of 20% by mass.

(Dye Composition Production Example 131)
32 g of a formalin condensate of sodium naphthalenesulfonate and 18 g of water were added to 50 g of the compound D-5 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 100 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound D-5 having a concentration of 20% by mass.

(Dye Composition Production Example 132)
32 g of a formalin condensate of sodium methylnaphthalenesulfonate and 18 g of water were added to 50 g of the compound D-5 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 100 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound D-5 having a concentration of 20% by mass.

(Dye Composition Production Example 133)
32 g of sodium ligninsulfonate and 18 g of water were added to 50 g of the compound D-5 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 100 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound D-5 having a concentration of 20% by mass.

(Dye Composition Production Example 134)
33 g of a formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound D-13 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 101 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound D-13 having a concentration of 20% by mass.

(Dye Composition Production Example 135)
33 g of a formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound D-4 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 102 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound D-4 having a concentration of 20% by mass.

(Dye Composition Production Example 136)
33 g of a formalin condensate of sodium naphthalenesulfonate and 17 g of water were added to 50 g of the compound D-4 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 102 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound D-4 having a concentration of 20% by mass.

(Dye Composition Production Example 137)
33 g of sodium ligninsulfonate and 17 g of water were added to 50 g of the compound D-4 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 102 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound D-4 having a concentration of 20% by mass.

(Dye Composition Production Example 138)
32 g of sodium ligninsulfonate and 18 g of water were added to 50 g of the compound E-1 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 103 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound E-1 having a concentration of 20% by mass.

(Dye Composition Production Example 139)
32 g of a formalin condensate of sodium naphthalenesulfonate and 18 g of water were added to 50 g of the compound F-1 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 104, and the mixture was stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of Compound F-1 having a concentration of 20% by mass.

(Dye Composition Production Example 140)
32 g of a formalin condensate of sodium naphthalenesulfonate and 18 g of water were added to 50 g of the compound G-1 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 105, and the mixture was stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound G-1 having a concentration of 20% by mass.

(Dye Composition Production Example 141)
32 g of a formalin condensate of sodium creosote oil sulfonate and 18 g of water were added to 50 g of the compound G-1 dye composition having a concentration of 20% by mass described in Dye Composition Production Example 105 and stirred for 20 minutes. This dye dispersion was spray-dried to obtain a powdery dye composition of compound G-1 having a concentration of 20% by mass.

Dispersants for making the compounds of the present invention into dye compositions are the distyrenated phenol-ethylene oxide adducts and tristyrenated phenol-ethylene oxide adducts described in Dye Composition Production Examples 1 to 49 and 68 to 105. , tribenzylphenol-ethylene oxide adducts, oxyethylene-oxypropylene copolymers, and other nonionic dispersants were effective.

On the other hand, anionic dispersants such as formalin condensates of sodium naphthalene sulfonate, formalin condensates of sodium creosote oil sulfonate, and sodium lignin sulfonate, which are described in Dye Composition Production Examples 50 to 67, are the compounds of the present invention. could not be made into a dye composition having a desired particle size (volume median particle size of 1.0 μm or less).

<Dyeing example>
(Dyeing of polypropylene fiber 1)
Dye compositions of the compounds described in Tables 3 to 9, or dye compositions such as disperse dye compounds conventionally used for dyeing polyester fibers etc. shown in Tables 3 to 9. Dyeing method using only one type Dyeing of polypropylene fibers was carried out by

(Staining example P1)
Water and acetic acid were added to 1.5 g of the dye composition of blue compound A-5 obtained in Dye Composition Production Example 1 (dye concentration: 20% by mass) to prepare a dye bath with a total amount of 2000 g and a pH of 4.5. . 100 g of polypropylene fiber was immersed in the above dye bath, dyed at 120° C. for 40 minutes (0.3% o.m.f.), washed thoroughly with water and dried to obtain a dyed blue polypropylene fiber.

(Staining examples P2 to P22)
A dyed polypropylene fiber dyed product was obtained by the same dyeing procedure as in Dyeing Example P1, except that the dye composition of the blue compound A-5 described in Dyeing Example P1 was changed to the dye composition of the compounds in Tables 10 to 14. .

(Staining example P26)
95 g of water was added to 5.0 g of the powdery dye composition of blue compound A-13 (dye concentration: 20% by mass) obtained in Dye Composition Production Example 106, and the mixture was stirred to prepare a dye dispersion. Water and acetic acid were added to this dye dispersion to prepare a dye bath with a total weight of 2000 g and a pH of 4.5. 100 g of polypropylene fiber was immersed in the above dye bath, dyed at 130° C. for 60 minutes (1.0% o.m.f.), then reduced, washed with water and dried to obtain a dyed blue polypropylene fiber.

(Staining examples P27 to P37)
Except for changing the powdery dye composition of the blue compound A-13 described in Dyeing Example P26 to the powdery dye composition of the compounds in Tables 10 to 14, by the same dyeing procedure as in Dyeing Example P26. A dyed polypropylene fiber dyeing was obtained.

The compounds used in Dyeing Examples P1 to P22 and Dyeing Examples P26 to P37 are shown in Tables 10 to 14.

Dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, sweat fastness test, rub fastness test, and hot pressing fastness test were performed on the polypropylene fiber dyed products obtained in Dyeing Examples. .

(1) Dyeability evaluation Dyeability was evaluated by the Total K/S value obtained by colorimetry of the dyed fabric. Colorimetry of the dyed cloth was performed using an integrating sphere spectrophotometer Color-Eye 5 (manufactured by Gretag Macbeth), pasting the dyed cloth on white paper, observing light source D65, and visual field of 2 degrees.

(2) Light Fastness Test The light fastness test was performed by an ultraviolet carbon arc lamp method according to JIS L0842:2004. The outline of the test method is as follows. Using an ultraviolet fade meter U48 (manufactured by Suga Test Instruments Co., Ltd.), the dyed cloth was exposed to light for 20 hours at a black panel temperature of 63±3° C., and then the discoloration was determined.

(3) Sublimation Fastness Test The sublimation fastness test was performed by a method according to JIS L0854:2013. The outline of the test method is as follows. The dyed cloth was sandwiched between nylon cloths and held at 120±2° C. for 80 minutes under a load of 12.5 kPa.

(4) Washing Fastness Test The washing fastness test was performed by a method according to JIS L0844:2011 (A-2). The outline of the test method is as follows. Attach the multi-weave fabric to the dyed fabric, wash for 30 minutes at 50±2°C in the presence of soap, and judge discoloration and contamination of the cotton and nylon parts of the multi-weave fabric. rice field. Also, the contamination of the residual liquid after washing was determined.

(5) Sweat Fastness Test The sweat fastness test was performed according to JIS L0848:2004. The outline of the test method is as follows. After attaching the multi-woven cloth to the dyed cloth and immersing it in an acidic artificial perspiration solution or alkaline artificial perspiration for 30 minutes, after holding at 37 ± 2 ° C. for 4 hours under a load of 12.5 kPa, drying at 60 ° C. or less, Discoloration and fading and contamination of the cotton portion and nylon portion of the multi-weave fabric were evaluated.

(6) Rubbing Fastness Test The rubbing fastness test was performed according to JIS L0849:2013. The outline of the test method is as follows. Rubbing fastness tester RT-300 (manufactured by Daiei Kagaku Seiki Seisakusho Co., Ltd.)
, the dyed cloth was reciprocally rubbed 100 times with a dry cotton cloth or wet cotton cloth under a load of 2 N, and the coloring of the cotton cloth was determined.

(7) Fastness Test to Hot Pressing Fastness test to hot pressing was performed by a method according to JIS L0850:2015 (A-2 drying). The outline of the test method is as follows. The dyed cloth was placed on top of the cotton cloth, and after being held for 15 seconds under a load of 4±1 kPa on a hot plate at 150° C., discoloration and contamination of the cotton cloth were evaluated.

Table 15 shows the evaluation results of dyeing examples of the compound of formula (A).

Regarding the dyeability of the compound of formula (A), R _A1 , R _A2 and R _A3 used in Dyeing Examples P1, P2 and P26 to P28 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _A1 , At least one of R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms). The compound in which all of R _A1 , R _A2 and R _A3 are alkyl groups having 3 or less carbon atoms, which is a disperse dye conventionally used for dyeing polyester fibers and the like used in Dyeing Example P3, has poor dyeability. there were.

Regarding each fastness of the compound of formula (A), R _A1 , R A2 and _{R A3 used} in Dyeing Examples P1, P2 and P26 to P28 are each independently an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms). Met.

Table 16 shows the evaluation results of dyeing examples of the compound of formula (B).

Regarding the dyeability of the compound of formula (B), R _B1 and R _B2 used in Dyeing Examples P4 to P5 and P29 to P31 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _B1 , At least one of R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms). The dyeability of the disperse dye used in Dyeing Example P8, which is a disperse dye conventionally used for dyeing polyester fibers and the like and in which R _B1 or R _B2 is not an alkyl group having 1 to 14 carbon atoms, was poor.
Regarding each fastness of the compound of formula (B), R _B1 and R _B2 used in Dyeing Examples P4 to P5 and P29 to P31 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms). there were.

Table 17 shows the evaluation results of staining examples of the compound of formula (C).

Regarding the dyeability of the compound of formula (C), R _C1 , R _C2 and R _C3 used in Dyeing Examples P10 and P32 to P34 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _C1 At least one of , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms). The compound in which at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 3 or less carbon atoms, which is a disperse dye used in Dyeing Example P12 and which has been conventionally used for dyeing polyester fibers, has poor dyeability. Met.

Regarding each fastness of the compound of formula (C), R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) was generally good.

Regarding each fastness of the compound of formula (C), R _C1 , R _C2 and R _C3 used in Dyeing Examples P10 and P32 to P34 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms), each fastness was good.

Table 18 shows the evaluation results of dyeing examples of the compound of formula (D).

Regarding the dyeability of the compound of formula (D), R _D1 and R _D2 used in Dyeing Examples P13 to P17, P35 and P36 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _D1 to and R _D2 is an alkyl group having 4 to 14 carbon atoms). However, in the case of the disperse dyes used in Dyeing Examples P18 to P20, which have been conventionally used for dyeing polyester fibers, each of the alkyl groups R _D1 and R _D2 has 1 to 3 carbon atoms. and its stainability was poor.

Further, each fastness of the compound of the formula (D) was better as the number of carbon atoms of R _D1 and R _D2 was larger.

Table 19 shows the evaluation results of staining examples of the compound of formula (G).

As for the dyeability of the compound of formula (G), the dyeability of the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples P21 and P37 was good. The dyeability of the compound in which R _G is an alkyl group having 3 carbon atoms, which is a disperse dye used in dyeing of polyester fibers and the like and used in Dyeing Example P22, was poor.

Regarding each fastness of the compound of the formula (G), the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples P21 and P37 were good.

(Polypropylene fiber dip dyeing 2)
Using a dye composition in which two or more of the compounds listed in Tables 3 to 9 are mixed and used, the polypropylene fiber is dyed in the same manner according to Dyeing Example P1, and the obtained polypropylene fiber dyed product is evaluated for dyeability, Fastness to light, fastness to sublimation, fastness to washing, fastness to perspiration, fastness to rubbing and fastness to hot pressing were conducted. The dyeability was evaluated by the Total K/S value and the L ^* , a ^* and b ^* values obtained by colorimetry of the dyed fabric. Color measurement of the dyed cloth was performed using an integrating sphere spectrophotometer Color-Eye 5 (manufactured by Gretag Macbeth), pasting the dyed cloth on white paper, observing light source D65, and visual field of 2 degrees.

Table 20 shows the evaluation results of dyeing examples using dye compositions in which two or more of the compounds listed in Tables 3 to 9 are mixed and used.

As shown in Table 20, when the orange dye, red dye, and blue dye obtained in the present invention were used in combination, a black dyed cloth with good dyeability and generally good fastness was obtained.

(Polyethylene fiber dip dyeing 1)
Dye compositions of the compounds described in Tables 3 to 9, or dye compositions such as disperse dye compounds conventionally used for dyeing polyester fibers etc. shown in Tables 3 to 9. Dyeing method using only one type Dyeing of polyethylene fibers was carried out by

(Staining example E1)
Water and acetic acid were added to 1.5 g of the dye composition of blue compound A-5 obtained in Dye Composition Production Example 1 (dye concentration: 20% by mass) to prepare a dye bath with a total amount of 2000 g and a pH of 4.5. . 100 g of polyethylene fiber was immersed in the dye bath, dyed at 100° C. for 40 minutes (0.3% o.m.f.), washed thoroughly with water and dried to obtain a blue polyethylene fiber dyed product.

(Staining examples E2 to E22)
A polyethylene fiber dyed product was obtained by the same dyeing procedure as in Dyeing Example E1, except that the dye composition of Blue Compound A-5 described in Dyeing Example E1 was changed to the dye composition of the compounds in Tables 21 to 25.

(Staining example E26)
95 g of water was added to 5.0 g of the powdery dye composition of blue compound A-13 (dye concentration: 20% by mass) obtained in Dye Composition Production Example 106, and the mixture was stirred to prepare a dye dispersion. Water and acetic acid were added to this dye dispersion to prepare a dye bath with a total weight of 2000 g and a pH of 4.5. 100 g of polyethylene fiber was immersed in the above dye bath and dyed at 110° C. for 60 minutes (1.0% o.m.f.), then thoroughly washed with water and dried to obtain a dyed blue polypropylene fiber.

(Staining examples E27 to E37)
Except for changing the powdery dye composition of the blue compound A-13 described in Dyeing Example E26 to the powdery dye composition of the compounds in Tables 21 to 25, by the same dyeing procedure as in Dyeing Example E26 A dyed polyethylene fiber dyeing was obtained.

The compounds used in Dyeing Examples E1 to E22 and Dyeing Examples E26 to E37 are shown in Tables 10 to 14.

Regarding the polyethylene fiber dyed product obtained in Dyeing Example, in the same manner as the polypropylene fiber dyed product obtained in (Polypropylene fiber dyeing 1) described above, dyeability evaluation, light fastness test, washing fastness test, sweat fastness A test and a rub fastness test were performed.

Table 26 shows the evaluation results of dyeing examples of the compound of formula (A).

Regarding the dyeability of the compound of formula (A), R _A1 , R A2 and R _A3 used in Dyeing Examples E1, E2 and _E26 to E28 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms), and the dyeability of the compound was good. The compound in which all of R _A1 , R _A2 and R _A3 are alkyl groups having 3 or less carbon atoms, which is a disperse dye used in Dyeing Example E3 and which has been conventionally used for dyeing polyester fibers, has poor dyeability. there were.

Regarding each fastness of the compound of formula (A), R _A1 , R A2 and _{R A3 used} in Dyeing Examples E1, E2 and E26 to E28 are each independently an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms.

Table 27 shows the evaluation results of staining examples of the compound of formula (B).

Regarding the dyeability of the compound of formula (B), R _B1 and R _B2 used in Dyeing Examples E4 to E5 and E29 to E31 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _B1 , At least one of R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms), and the dyeability of the compound was good. The dyeability of the disperse dye used in Dyeing Example E8, which is a disperse dye conventionally used for dyeing polyester fibers and the like and in which R _B1 or R _B2 is not an alkyl group having 1 to 14 carbon atoms, was poor.

Regarding each fastness of the compound of formula (B), R _B1 and R _B2 used in Dyeing Examples E4 to E5 and E29 to E31 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms.

Table 28 shows the evaluation results of staining examples of the compound of formula (C).

Regarding the dyeability of the compound of formula (C), R _C1 , R _C2 and R _C3 used in Dyeing Examples E10 and E32 to E34 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _C1 At least one of , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms). The compound in which at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 3 or less carbon atoms, which is a disperse dye used in Dyeing Example E12 and which has been conventionally used for dyeing polyester fibers, has poor dyeability. Met.

Regarding each fastness of the compound of formula (C), R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms).

Regarding each fastness of the compound of formula (C), R _C1 , R _C2 and R _C3 used in Dyeing Examples E10 and E32 to E34 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms), each fastness was good.

Table 29 shows the evaluation results of dyeing examples of the compound of formula (D).

Regarding the dyeability of the compound of formula (D), R _D1 and R _D2 used in Dyeing Examples E13 to E17, E35 and E36 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _D1 to and R _D2 is an alkyl group having 4 to 14 carbon atoms). However, in the case of disperse dyes conventionally used for dyeing polyester fibers and the like used in Dyeing Examples E18 to E20, each of the alkyl groups R _D1 and R _D2 has 1 to 3 carbon atoms. and its stainability was poor.

Further, each fastness of the compound of the formula (D) was better as the number of carbon atoms of R _D1 and R _D2 was larger.

Table 30 shows the evaluation results of staining examples of the compound of formula (G).

As for the dyeability of the compound of formula (G), the dyeability of the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples E21 and E37 was good. The dyeability of the compound in which R _G is an alkyl group having 3 carbon atoms, which is a disperse dye used in Dyeing Example E22 and which has been conventionally used for dyeing polyester fibers, was poor.

Regarding each fastness of the compound of the formula (G), the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples E21 and E37 were good.

(Polyethylene fiber dip dyeing 2)
Using a dye composition in which two or more of the compounds listed in Tables 3 to 9 are mixed and used, polyethylene fibers are dyed in the same manner according to Dyeing Example E1, and the obtained polyethylene fiber dyed product is treated with the above-mentioned (polypropylene Dyeability evaluation, light fastness test, wash fastness test, sweat fastness test, and rub fastness test were performed in the same manner as the polypropylene fiber dyed product obtained in dyeing of fibers 2).

Table 31 shows the evaluation results of dyeing examples using dye compositions in which two or more of the compounds listed in Tables 3 to 9 are mixed and used.

As shown in Table 31, when the orange dye, red dye, and blue dye obtained in the present invention were mixed and used, a black dyed cloth with good dyeability and generally good fastness was obtained.

(Printing of polypropylene fiber 1)
Printing method using only one type of dye composition such as a dye composition of the compounds described in Tables 3 to 9 or a disperse dye compound conventionally used for dyeing polyester fibers etc. shown in Tables 3 to 9 Dyeing of polypropylene fibers was carried out by

(Dyeing example PP1)
5.8 g of carboxymethyl cellulose, 0.3 g of sodium chlorate and 0.3 g of tartaric acid were added to 73.6 g of water and stirred until uniform to obtain a paste A. To the paste A was added a dye dispersion prepared by adding 18.5 g of water to 1.5 g of the dye composition (dye concentration: 20% by mass) of the blue compound A-13 obtained in Dye Composition Production Example 76 and stirring. and stirred until uniform to prepare a printing paste (0.3% o.m.p.). The printing paste was printed on a polypropylene fiber, dried by dry heat at 110°C for 3 minutes, and then printed by H.I. T. Color was developed with a steamer at 130° C. for 6 minutes, then reduced washing, washing with water and drying to obtain a blue dyed polypropylene fiber.

(Dyeing examples PP2 to PP12)
A dyed polypropylene fiber dyed product was obtained by the same dyeing procedure as in Dyeing Example PP1 except that the dye composition of the blue compound A-13 described in Dyeing Example PP1 was changed to the dye composition of the compounds in Tables 32 to 36. .

(Dyeing example PP13)
5.8 g of carboxymethyl cellulose, 0.3 g of sodium chlorate and 0.3 g of tartaric acid were added to 73.6 g of water and stirred until uniform to obtain a paste A. A dye obtained by adding 18.5 g of water to 1.5 g of the powdery dye composition (dye concentration: 20% by mass) of the blue compound A-5 obtained in Dye Composition Production Example 107 to the paste A and stirring. A printing paste was prepared by adding the dispersion and stirring until homogeneous (0.3% o.m.p.). The printing paste was printed on a polypropylene fiber, dried by dry heat at 110°C for 3 minutes, and then printed by H.I. T. Color was developed with a steamer at 130° C. for 6 minutes, then reduced washing, washing with water and drying to obtain a blue dyed polypropylene fiber.

(Dyeing examples PP14 to PP19)
Except for changing the powdery dye composition of the blue compound A-5 described in Dyeing Example PP13 to the powdery dye composition of the compounds in Tables 32 to 36, by the same dyeing procedure as in Dyeing Example PP13 A dyed polypropylene fiber dyeing was obtained.

Regarding the polypropylene fiber dyed product obtained in Dyeing Example, in the same manner as the polypropylene fiber dyed product obtained in (Polypropylene fiber dyeing 1) described above, dyeability evaluation, light fastness test, sublimation fastness test, washing fastness Tests, perspiration fastness tests, rub fastness tests and hot pressing fastness tests were carried out.

Table 37 shows the evaluation results of staining examples of the compound of formula (A).

Regarding the dyeability of the compound of formula (A), R _A1 , R A2 and R _A3 used in Dyeing Examples PP1 to PP3 and _PP13 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _A1 and R At least one of _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms).

Further, with respect to each fastness of the compound of formula (A), R _A1 , R _A2 and R _A3 used in Dyeing Examples PP1 to PP3 and PP13 are each independently an alkyl group having 1 to 14 carbon atoms (where R At least one of _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms). Met.

Table 38 shows the evaluation results of staining examples of the compound of formula (B).

Regarding the dyeability of the compound of formula (B), R _B1 and R _B2 used in Dyeing Examples PP4 to PP5 and PP14 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _B1 and R _B2 and at least one of R _B3 is an alkyl group having 4 to 14 carbon atoms).

Further, regarding each fastness of the compound of formula (B), R _B1 and R _B2 used in Dyeing Examples PP4 to PP5 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _B1 and R _B2 and at least one of R _B3 is an alkyl group having 4 to 14 carbon atoms), each fastness was good.

Table 39 shows the evaluation results of staining examples of the compound of formula (C).

Regarding the dyeability of the compound of formula (C), R _C1 , R _C2 and R _C3 used in Dyeing Examples PP7 to PP9, PP15 and PP16 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms).

Further, for each fastness of the compound of formula (C), R _C1 , R _C2 and R _C3 used in Dyeing Examples PP7 to PP9, PP15 and PP16 each independently represent an alkyl group having 1 to 14 carbon atoms. The compound (provided that at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) had good fastness.

Table 40 shows the evaluation results of dyeing examples of the compound of formula (D).

Regarding the dyeability of the compound of formula (D), R _D1 and R _D2 used in Dyeing Examples PP10, PP11, PP17 and PP18 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _D1 and R At least one of _D2 is an alkyl group having 4 to 14 carbon atoms).

Further, regarding each fastness of the compound of formula (D), R _D1 and R _D2 used in Dyeing Examples PP10, PP11, PP17 and PP18 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms), each fastness was good.

Table 41 shows the evaluation results of staining examples of the compound of formula (G).

As for the dyeability of the compound of formula (G), the dyeability of the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples PP12 and PP19 was good.

Regarding each fastness of the compound of the formula (G), the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples PP12 and PP19 were good.

(Printing of polypropylene fiber 2)
Using a dye composition in which two or more of the compounds listed in Tables 3 to 9 are mixed and used, 1.2% o.o. m. p. was used to dye polypropylene fibers.

Furthermore, using a dye composition in which two or more of the compounds listed in Tables 3 to 9 are mixed and used, 1.8% o.d. m. p. was used to dye polypropylene fibers.

Regarding the obtained polypropylene fiber dyed product, in the same manner as the polypropylene fiber dyed product obtained in (Polypropylene fiber impregnation 2), dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration A fastness test, a fastness to rubbing test and a fastness to hot pressing test were carried out.

The results are shown in Table 42.

As shown in Table 42, when the orange dye, red dye, and blue dye obtained in the present invention were mixed and used, a black dyed cloth with good dyeability and good fastness was obtained.

(Printing of polyethylene fiber 1)
Printing method using only one type of dye composition such as a dye composition of the compounds described in Tables 3 to 9 or a disperse dye compound conventionally used for dyeing polyester fibers etc. shown in Tables 3 to 9 Dyeing of polyethylene fibers was carried out by

(Dyeing example EP1)
5.8 g of carboxymethyl cellulose, 0.3 g of sodium chlorate and 0.3 g of tartaric acid were added to 73.6 g of water and stirred until uniform to obtain a paste A. To the paste A was added a dye dispersion prepared by adding 18.5 g of water to 1.5 g of the dye composition (dye concentration: 20% by mass) of the blue compound A-13 obtained in Dye Composition Production Example 76 and stirring. and stirred until uniform to prepare a printing paste (0.3% o.m.p.). The printing paste was printed on a polyethylene fiber, and after dry heat drying at 110°C for 3 minutes, H.I. T. Color was developed with a steamer at 110° C. for 6 minutes, then reduced, washed with water and dried to obtain a blue polyethylene fiber dyed product.

(Dyeing examples EP2 to EP12)
A dyed polyethylene fiber dyed product was obtained by the same dyeing procedure as in Dyeing Example EP1 except that the dye composition of the blue compound A-13 described in Dyeing Example EP1 was changed to the dye composition of the compounds in Tables 43 to 47. .

(Dyeing example EP13)
5.8 g of carboxymethyl cellulose, 0.3 g of sodium chlorate and 0.3 g of tartaric acid were added to 73.6 g of water and stirred until uniform to obtain a paste A. A dye obtained by adding 18.5 g of water to 1.5 g of the powdery dye composition (dye concentration: 20% by mass) of the blue compound A-5 obtained in Dye Composition Production Example 105, and stirring the mixture. A printing paste was prepared by adding the dispersion and stirring until homogeneous (0.3% o.m.p.). The printing paste was printed on a polyethylene fiber, and after dry heat drying at 110°C for 3 minutes, H.I. T. Color was developed with a steamer at 110° C. for 6 minutes, then reduced, washed with water and dried to obtain a blue polyethylene fiber dyed product.

(Dyeing examples EP14 to EP19)
Except for changing the powdery dye composition of the blue compound A-5 described in Dyeing Example EP13 to the powdery dye composition of the compounds in Tables 44 to 47, by the same dyeing procedure as in Dyeing Example EP13. A dyed polyethylene fiber dyeing was obtained.

Regarding the polyethylene fiber dyed product obtained in Dyeing Example, in the same manner as the polypropylene fiber dyed product obtained in (Polypropylene fiber dyeing 1) described above, dyeability evaluation, light fastness test, washing fastness test, sweat fastness Tests and rub fastness tests were performed.

Table 48 shows the evaluation results of staining examples of the compound of formula (A).

Regarding the dyeability of the compound of formula (A), R _A1 , R A2 and R _A3 used in Dyeing Examples EP1 to EP3 and _EP13 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _A1 and R At least one of _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms).

Further, with respect to each fastness of the compound of formula (A), R _A1 , R _A2 and R _A3 used in Dyeing Examples EP1 to EP3 and EP13 are each independently an alkyl group having 1 to 14 carbon atoms (where R At least one of _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms.

Table 49 shows the evaluation results of staining examples of the compound of formula (B).

Regarding the dyeability of the compound of formula (B), R _B1 and R _B2 used in Dyeing Examples EP4 to EP5 and EP14 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _B1 and R _B2 and at least one of R _B3 is an alkyl group having 4 to 14 carbon atoms).

Further, regarding each fastness of the compound of formula (B), R _B1 and R _B2 used in Dyeing Examples EP4 to EP5 and EP14 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _B1 , and at least one of R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms), each fastness was good.

Table 50 shows the evaluation results of dyeing examples of the compound of formula (C).

Regarding the dyeability of the compound of formula (C), R _C1 , R _C2 and R _C3 used in Dyeing Examples EP7 to EP9, EP15 and EP16 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms).

Further, for each fastness of the compound of formula (C), R _C1 , R _C2 and R _C3 used in Dyeing Examples EP7 to EP9, EP15 and EP16 each independently represent an alkyl group having 1 to 14 carbon atoms. (where at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) had good fastness.

Table 51 shows the evaluation results of dyeing examples of the compound of formula (D).

Regarding the dyeability of the compound of formula (D), R _D1 and R _D2 used in Dyeing Examples EP10, EP11, EP17 and EP18 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R _D1 and R At least one of _D2 is an alkyl group having 4 to 14 carbon atoms).

Further, regarding each fastness of the compound of formula (D), R _D1 and R _D2 used in Dyeing Examples EP10, EP11, EP17 and EP18 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that R At least one of _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms), each fastness was good.

Table 52 shows the evaluation results of staining examples of the compound of formula (G).

As for the dyeability of the compound of formula (G), the dyeability of the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples EP12 and EP19 was good.

Regarding each fastness of the compound of formula (G), the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples EP12 and EP19 were good.

(Printing of polyethylene fiber 2)
Using a dye composition obtained by mixing two or more of the compounds listed in Tables 3 to 9, 1.2% o.d. m. p. Dyeing of polyethylene fibers was carried out using the printing paste of

Furthermore, using a dye composition in which two or more of the compounds listed in Tables 3 to 9 are mixed and used, 1.8% o.d. m. p. Dyeing of polyethylene fibers was carried out using the printing paste of

Regarding the obtained polyethylene fiber dyed product, in the same manner as the polypropylene fiber dyed product obtained in the above (Polypropylene fiber dyeing 2), dyeability evaluation, light fastness test, washing fastness test, sweat fastness test and rubbing A fastness test was performed.

The results are shown in Table 53.

As shown in Table 53, when the orange dye, red dye, and blue dye obtained in the present invention were mixed and used, a black dyed cloth with good dyeability and good fastness was obtained.

As described above, the present invention is not limited to the above-described embodiments, and the present invention also includes suitable combinations or replacements of the configurations of the embodiments.

Further, it is also possible to appropriately rearrange the combinations and the order of steps in the embodiments based on the knowledge of a person skilled in the art, and to add modifications such as various design changes to the embodiments. Embodiments described may also fall within the scope of the present invention.

The present invention is a polyolefin fiber used for clothes, underwear, hats, socks, gloves, clothing such as sports clothing, vehicle interior materials such as seat seats, interior goods such as carpets, curtains, mats, sofa covers, cushion covers, etc. can be used to dye

Claims (31)

At least one of the compounds represented by the following general formulas (A) to (G) and at least two nonionic dispersants ,
One of the nonionic dispersants is an oxyethylene-oxypropylene copolymer,
dye composition.

[in formula (A),
X _A is a nitro group,
Y _A represents a halogen atom,
R _A1 , R _A2 and R _A3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms);
R _A4 represents an alkyl group having 1 to 4 carbon atoms. ]

[In the formula (B), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _B1 , R _B2 and R _B3 is a an alkyl group). ]

[In formula (C),
_X and _Y represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a nitro group and a cyano group, a hydrogen atom and a hydrogen atom;
R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms). ]

[In formula (D), X _D and Y _D each independently represent a hydrogen atom, a halogen atom, or a cyano group,
R _D1 represents an alkyl group having 1 to 14 carbon atoms,
R _D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (provided that at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms ). ]

[In formula (E), X _E and Y _E each independently represent a halogen atom, and R _E represents an alkyl group having 4 to 18 carbon atoms. ]

[In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms. ]

[In the formula (G), R _G represents an alkyl group having 7 or 10 to 18 carbon atoms. ] 2. The dye composition according to claim 1, wherein the oxyethylene-oxypropylene copolymer has 300 moles of oxyethylene and 55 moles of oxypropylene. The nonionic dispersant is at least one selected from the group consisting of polyoxyethylene alkylphenyl ethers, polyoxyethylene aryl phenyl ethers, polyoxyethylene alkyl aryl ethers, and polyoxyethylene aryl aryl ethers. 3. The dye composition according to 1 or 2. The dye composition according to any one of claims 1 to 3, wherein the nonionic dispersant is at least one selected from the group consisting of polyoxyethylene aryl phenyl ethers and polyoxyethylene aryl aryl ethers. . The dye composition according to any one of claims 1 to 4, wherein the nonionic dispersant is polyoxyethylene arylphenyl ether. A dye composition for dyeing black, comprising at least three compounds represented by the following general formulas (A) to (G) and a nonionic dispersant.

[in formula (A),
X _A is a nitro group,
Y _A represents a halogen atom,
R _A1 , R _A2 and R _A3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms);
R _A4 represents an alkyl group having 1 to 4 carbon atoms. ]

[In the formula (B), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _B1 , R _B2 and R _B3 is a an alkyl group). ]

[In formula (C),
X _and Y represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a nitro group and a cyano group, a hydrogen atom and a hydrogen atom _;
R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (provided that at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms). ]

[In formula (D), X _D and Y _D each independently represent a hydrogen atom, a halogen atom, or a cyano group,
R _D1 represents an alkyl group having 1 to 14 carbon atoms,
R _D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (provided that at least one of R D1 and R D2 is an alkyl group having 4 _to 14 _carbon atoms ). ]

[In formula (E), X _E and Y _E each independently represent a halogen atom, and R _E represents an alkyl group having 4 to 18 carbon atoms. ]

[In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms. ]

[In the formula (G), R _G represents an alkyl group having 7 or 10 to 18 carbon atoms. ] The dye composition for dyeing black is
a blue compound consisting of the compound of the general formula (A);
a blue compound consisting of the compound of the general formula (B);
and an orange compound consisting of the compound of general formula (D),
A dye composition according to claim 6 . The dye composition for dyeing black is
at least one purple or blue compound selected from the group consisting of the compound of general formula (A), the compound of general formula (B), the compound of general formula (C), and the compound of general formula (F);
at least one red compound selected from the group consisting of compounds of general formula (C) and compounds of general formula (D);
The dye composition according to claim 6, comprising at least one yellow or orange compound selected from the group consisting of the compound of general formula (D), the compound of general formula (E) and the compound of general formula (G). thing. The dye composition for dyeing black is
at least one purple or blue compound selected from the group consisting of the compound of general formula (A), the compound of general formula (B) and the compound of general formula (F);
a red compound of the compound of general formula (C);
9. The dye composition according to claim 8, comprising at least one orange compound selected from the group consisting of compounds of general formula (D) and compounds of general formula (E). The dye composition for dyeing black is
10. The dye according to claim 8 or 9, comprising a blue compound of the compound of general formula (A), a red compound of the compound of general formula (C), and an orange compound of the compound of general formula (D). Composition. The content of the compound in the dye composition for dyeing black is
For the sum of said purple or blue compound, said red compound, and said yellow or orange compound,
the ratio of the purple or blue compound is 30 to 70% by mass;
the ratio of the red compound is 5 to 25% by mass;
the proportion of said yellow or orange compound is in the range of 15 to 55% by weight;
A dye composition according to any one of claims 8 to 10. The content of the compound in the dye composition for dyeing black is
For the sum of said purple or blue compound, said red compound, and said yellow or orange compound,
the ratio of the purple or blue compound is 40 to 60% by mass;
the ratio of the red compound is 5 to 25% by mass;
the proportion of said yellow or orange compound is in the range of 25 to 45% by weight;
A dye composition according to any one of claims 8 to 11. The nonionic dispersant is selected from the group consisting of polyoxyethylene alkylphenyl ethers, polyoxyethylene aryl phenyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene aryl aryl ethers, and oxyethylene-oxypropylene copolymers. The dye composition according to any one of claims 6 to 12 , which is at least one. Any one of claims 6 to 13 , wherein the nonionic dispersant is at least one selected from the group consisting of polyoxyethylene aryl phenyl ethers, polyoxyethylene aryl aryl ethers, and oxyethylene-oxypropylene copolymers. The dye composition according to claim 1. The dye composition according to any one of claims 6 to 14 , wherein the nonionic dispersant is at least one selected from polyoxyethylene arylphenyl ethers and oxyethylene-oxypropylene copolymers. The dye composition according to any one of claims 6 to 15 , wherein the nonionic dispersant is a polyoxyethylene arylphenyl ether and an oxyethylene-oxypropylene copolymer. The dye composition according to any one of claims 1 to 16 , which is a dye composition for dyeing polyolefin fibers. The dye composition according to any one of claims 1 to 17 , which is a dye composition used in water-based dyeing. The dye composition according to any one of claims 1 to 18 , wherein the dye composition is powdery. 20. The dye composition of claim 19, wherein said powdery dye composition is produced by spray drying. A method for dyeing a fiber, comprising:
A method comprising water-based dyeing of fibers with the dye composition of any one of claims 1-20 . 22. The dyeing method according to claim 21, wherein the dyeing step is at least one selected from the group consisting of dip dyeing, textile printing, inkjet dyeing, transfer dyeing, and continuous dyeing. 23. The dyeing method according to claim 21 or 22 , wherein the dyeing step is at least one selected from dyeing and printing. The dyeing method according to any one of claims 21 to 23 , wherein the dyeing step is textile printing. The fiber is polyolefin,
The dyeing method according to any one of claims 21 to 24 , wherein the dyeing step is performed at 80°C to 130°C. The dyeing method according to any one of claims 21 to 24 , wherein the fiber is polypropylene and the dyeing step is performed at 110°C to 130°C. The fiber is polyethylene,
The dyeing method according to any one of claims 21 to 24 , wherein the dyeing step is performed at 90°C to 110°C. The dyeing method is printing, and the concentration of the dye to the printing paste is 0.001%o. m. p. to 5% o.d. m. p. (on the mass of paste), the staining method according to any one of claims 21 to 27 . The dyeing method is dip dyeing,
The concentration of said dye on said fiber is 0.001% o.d. m. f. to 10% o.d. m. f. (on the mass of fiber) . A fiber dyed by the dyeing method according to any one of claims 21-29 . A compound of the following general formula (F).

[In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms. ]