Dye composition

Abstract

An object of the present invention is to provide a dye composition capable of highly concentrating and dyeing fibers into various hues and having excellent dye fastness such as light fastness, sublimation fastness, and washing fastness of the dyed product, a method for dyeing fibers, fibers dyed by the dyeing method, and compounds. There are provided a dye composition containing at least one of the compounds represented by general formulas (A) to (G) and a nonionic dispersant, a method for dyeing fibers, fibers dyed by the dyeing method, and compounds.

Description

Technical Field

[0001] The present invention relates to a dye composition, a method for dyeing a fiber, a fiber dyed by the dyeing method, and a compound. Background Art

[0002] Polyolefin resins such as polypropylene resin and polyethylene resin are crystalline thermoplastic resins, and have excellent properties such as being inexpensive, easy to process, high strength, high chemical resistance, high abrasion resistance, high flexural resistance, lightweight, low hygroscopicity, low thermal conductivity, and high antistatic property.

[0003] On the other hand, polyolefin resins are high molecular compounds in which both the main chain and the side chain are composed of hydrocarbons, and due to reasons such as low affinity and compatibility with conventional dye compounds and the absence of functional groups effective for chemical reactions, high-concentration and high-fastness dyeing is considered extremely difficult.

[0004] Therefore, most of the colored polyolefin resins available in the market at present are resins that add colored pigments at the manufacturing stage of polymer pellets or the like, and then are spun into a desired shape and formed.

[0005] In this coloring method, it is necessary to determine the color at the initial stage of the resin product manufacturing process. In addition, considering cost accounting, it is necessary to produce a certain amount or more of one color, and as a result, the freedom of color selection is restricted.

[0006] Furthermore, when changing the color of the resin product, it is necessary to replace the colored resin of the previous color remaining in the resin product manufacturing apparatus with the colored resin of the next color. At this time, a large amount of waste resin is generated, and problems such as waste of time and energy occur.

[0007] As described in Non-Patent Document 1, polypropylene resin and polyethylene resin are among the four major general-purpose synthetic resins along with polyvinyl chloride resin and polystyrene resin, and are used in a wide range of fields.

[0008] However, the uses of polypropylene resin and polyethylene resin as synthetic fibers are very limited.

[0009] The reason is considered to be that, as described above, high-concentration and high-fastness dyeing of polypropylene resin fibers and polyethylene resin fibers is extremely difficult, the monofilament fineness has to be increased in the only effective coloring method, i.e., the masterbatch coloring method using colored pigments, and in addition, the freedom of color selection is restricted.

[0010] To date, in order to perform aqueous dyeing of polyolefin resin fibers, attempts have been made to change the molecular structure of dyes, and dyes for dyeing polyolefin resin fibers have been proposed in Patent Documents 1 to 5.

[0011] In Patent Document 1, production examples of red dyes and purple dyes obtained by introducing a phenoxy group having an alkyl or cycloalkyl group with 3 to 12 carbon atoms as a substituent into an anthraquinone-based dye and dyeing examples of polypropylene resin fibers using them are described.

[0012] However, with respect to these anthraquinone-based red dyes or anthraquinone-based purple dyes, high-concentration dyeing of polyolefin-based resin fibers is difficult. Furthermore, regarding the form of the dye when used in dyeing, there are descriptions such as dissolving these anthraquinone-based red dyes in alcohols or acetones as organic solvents and then using them, and it is difficult to say that they are environmentally friendly.

[0013] In Patent Document 2, production examples of blue dyes obtained by introducing a phenoxy group having an alkyl, cycloalkyl, or halogen group with 1 to 9 carbon atoms as a substituent into an anthraquinone-based dye and dyeing examples of polyester fibers, polyamide fibers, and polyolefin-based resin fibers using them are described.

[0014] However, with respect to these anthraquinone-based blue dyes, high-concentration dyeing of polyolefin-based resin fibers is difficult, and in addition, there are no specific descriptions regarding the dyeing fastness of the obtained dyed products. Furthermore, regarding the form of the dye when used in dyeing, there are descriptions such as dissolving these anthraquinone-based blue dyes in alcohols or acetones as organic solvents and then using them, and it is difficult to say that they are environmentally friendly.

[0015] In Patent Document 3, production examples of blue dyes obtained by introducing a phenoxy group having an alkyl or halogen group with 1 to 9 carbon atoms as a substituent into an anthraquinone-based dye and dyeing examples of polyolefin-based resin fibers using them are described.

[0016] However, with respect to these anthraquinone-based blue dyes, high-concentration dyeing of polyolefin-based resin fibers is difficult, and in addition, there are no specific descriptions regarding the dyeing fastness of the obtained dyed products. Furthermore, regarding the form of the dye when used in dyeing, there are descriptions such as crushing these anthraquinone-based blue dyes together with a suitable dispersant such as sodium dinaphthylmethanesulfonate and then using them, but no specific crushing method is described. In addition, as other forms, there are descriptions such as dissolving them in alcohols or acetones as organic solvents and then using them, and it is difficult to say that they are environmentally friendly.

[0017] In Patent Document 4, dyeing examples of polyolefin-based resin fibers using blue dyes obtained by introducing an alkylamino or cycloalkylamino group at the α-position of an anthraquinone-based dye are described.

[0018] However, with respect to these anthraquinone-based blue dyes, high-concentration dyeing of polyolefin-based resin fibers is difficult, and in addition, there are no specific descriptions regarding the dyeing fastness of the obtained dyed products.

[0019] In Patent Document 5, production examples of red dyes obtained by introducing a phenoxy group having two substituents selected from sec-butyl, sec-pentyl, and tert-pentyl into an anthraquinone-based dye and dyeing examples of polypropylene resin fibers using them are described.

[0020] However, with respect to these anthraquinone-based red dyes, high-concentration dyeing of polyolefin-based resin fibers is difficult, and moreover, there is no specific description of the dyeing fastness of the obtained dyed products. Furthermore, regarding the form of the dyes when used in dyeing, there is a description of using these anthraquinone-based red dyes in a paste state, but no specific production method of the dye paste is described. In addition, as other forms, there are descriptions such as using them after dissolving in dimethylformamide as an organic solvent, and it is difficult to say that they are environmentally friendly.

[0021] In Patent Document 6, production examples of monoazo-based dyes having long-chain alkyl groups and dyeing examples of fine denier polyester fibers using them are described. However, dyeing examples in polyolefin-based fibers using them are not described. Furthermore, regarding the form of the dyes when used in dyeing, there is a description of using these monoazo-based dyes in a paste state using an appropriate dispersant, but no specific production method of the dye paste is described.

[0022] In addition, in order to improve the dyeability of polyolefin-based resin fibers, various studies have been conducted on the modification of polyolefin-based resin fibers.

[0023] As modification techniques, various techniques are known, such as the blending of a dyeable resin component such as polyester, copolymerization with a vinyl-based monomer having a dyeable group, and the blending of a dyeing accelerator such as a metal salt of stearic acid.

[0024] Although the dyeability of these modified polyolefin-based resin fibers is improved, there is a problem that the strength of the yarn is reduced by the dyeing treatment, and in the case of using it for clothes, etc., the strength becomes insufficient.

[0025] If a method for highly concentrated and highly fast dyeing of polypropylene resin fibers and polyethylene resin fibers is put into practical use, it will be possible to color inexpensive ordinary yarns with a small monofilament fineness without color number limitation, and new uses are expected to be developed in fields such as clothing and vehicle interior materials that have not been applicable to polypropylene resin fibers and polyethylene resin fibers and require high designability.

[0026] Prior Art Documents

[0027] Patent Documents

[0028] Patent Document 1: Japanese Patent Publication No. 38-10741

[0029] Patent Document 2: Japanese Patent Publication No. 40-1277

[0030] Patent Document 3: Japanese Patent Publication No. 41-3515

[0031] Patent Document 4: British Patent Specification No. 872,882

[0032] Patent Document 5: US Patent No. 3,536,735

[0033] Patent Document 6: Japanese Unexamined Patent Application Publication No. 55-152869

[0034] Non-Patent Document

[0035] Non-Patent Document 1: Hiroshi Yamamoto, Journal of the Fiber Society, 61(2005), 319 - 321. Summary of the Invention

[0036] Problems to be Solved by the Invention

[0037] Accordingly, an object of the present invention is to provide a dye composition, a method for dyeing fibers, fibers dyed by the dyeing method, and a compound, which can dye fibers at a high concentration into various hues and have excellent dye fastness such as light fastness, sublimation fastness, and washing fastness of the dyed product.

[0038] Means for Solving the Problems

[0039] The present invention relates to a dye composition comprising at least one compound represented by the following general formulas (A) to (G) and a nonionic dispersant.

[0040] [Chemical Formula 1]

[0041]

[0042] [In formula (A),

[0043] X A is nitro,

[0044] Y A represents a halogen atom,

[0045] R A1 、R A2 and R A3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R A1 、R A2 and R A3 is an alkyl group having 4 to 14 carbon atoms),

[0046] R A4 represents an alkyl group having 1 to 4 carbon atoms.]

[0047] [Chemical Formula 2]

[0048]

[0049] [In formula (B), R B1 , R B2 and R B3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms).]

[0050] [Chemical formula 3]

[0051]

[0052] [In formula (C),

[0053] X C and Y C represent any one 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, and 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 (wherein at least one of R C1 , R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms).]

[0054] [Chemical formula 4]

[0055]

[0056] [In formula (D), X D and Y D each independently represent a hydrogen atom, a halogen atom or a cyano group,

[0057] R D1 represents an alkyl group having 1 to 14 carbon atoms,

[0058] R D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms obtained by being substituted with CN (wherein at least one of R D1 and R D2 is an alkyl group having 4 to 14 carbon atoms).]

[0059] [Chemical formula 5]

[0060]

[0061] [In formula (E), X E and Y E each independently represent a halogen atom, R Erepresents an alkyl group having 4 to 18 carbon atoms.]

[0062] [Chemical formula 6]

[0063]

[0064] [In formula (F), R F1 and R F2 each independently represent an alkyl group having 4 to 14 carbon atoms.]

[0065] [Chemical formula 7]

[0066]

[0067] [In formula (G), R G represents an alkyl group having 7 or 10 to 18 carbon atoms.]

[0068] Furthermore, the present invention provides a method, which is a method for dyeing fibers, comprising a step of subjecting the fibers to aqueous dyeing using the dye composition of the present invention.

[0069] Furthermore, the present invention provides a fiber which is dyed by the dyeing method of the present invention.

[0070] Furthermore, the present invention provides any one of the compounds represented by the following general formulas (A) to (G).

[0071] [Chemical formula 8]

[0072]

[0073] [In formula (A),

[0074] X A is nitro,

[0075] Y A represents a halogen atom,

[0076] R A1 , R A2 and R A3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R A1 , R A2 and R A3 is an alkyl group having 4 to 14 carbon atoms),

[0077] R A4 represents an alkyl group having 1 to 4 carbon atoms.]

[0078] [Chemical formula 9]

[0079]

[0080] [In formula (B), RB1 , R B2 and R B3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein, at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms).]

[0081] [Chemical Formula 10]

[0082]

[0083] [In formula (C),

[0084] X C and Y C each independently 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, and a hydrogen atom and a hydrogen atom,

[0085] R C1 , R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein, at least one of R C1 , R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms).]

[0086] [Chemical Formula 11]

[0087]

[0088] [In formula (D),

[0089] X D and Y D each independently represents a hydrogen atom, a halogen atom or a cyano group,

[0090] R D1 represents an alkyl group having 1 to 14 carbon atoms,

[0091] R D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms obtained by being substituted with CN (wherein, at least one of R D1 and R D2 is an alkyl group having 4 to 14 carbon atoms).]

[0092] [Chemical Formula 12]

[0093]

[0094] [In formula (E), X E and Y E each independently represents a halogen atom, RE represents an alkyl group having 4 to 18 carbon atoms.

[0095] [Chemical formula 13]

[0096]

[0097] [In formula (F), R F1 and R F2 each independently represent an alkyl group having 4 to 14 carbon atoms.

[0098] [Chemical formula 14]

[0099]

[0100] [In formula (G), R G represents an alkyl group having 7 or 10 to 18 carbon atoms.

[0101] Advantages of the Invention

[0102] The dye composition of the present invention can dye fibers at a high concentration into various hues, and the dye fastness of the dyed product, such as light fastness, sublimation fastness, and washing fastness, is excellent. Detailed Embodiments

[0103] The inventors of the present invention found that: dyes containing the following specific compounds have improved affinity for fibers and can dye fibers at a high concentration into various hues, thus completing the present invention.

[0104] <Compounds of general formulas (A) to (G)>

[0105] The compounds of general formulas (A) to (G) contained in the dyes of the present invention are as described below.

[0106] [Chemical formula 15]

[0107]

[0108] [In formula (A),

[0109] X A is nitro,

[0110] Y A represents a halogen atom,

[0111] R A1 , R A2 and R A3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R A1 , R A2 and R A3 is an alkyl group having 4 to 14 carbon atoms),

[0112] RA4 represents an alkyl group having 1 to 4 carbon atoms.

[0113] [Chemical Formula 16]

[0114]

[0115] [In formula (B), R B1 , R B2 and R B3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein, at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms).

[0116] [Chemical Formula 17]

[0117]

[0118] [In formula (C),

[0119] X C and Y C represent any one 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, and a hydrogen atom and a hydrogen atom,

[0120] R C1 , R C2 and R C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein, at least one of R C1 , R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms).

[0121] [Chemical Formula 18]

[0122]

[0123] [In formula (D), X D and Y D each independently represent a hydrogen atom, a halogen atom or a cyano group,

[0124] R D1 represents an alkyl group having 1 to 14 carbon atoms,

[0125] R D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted by CN (wherein, at least one of R D1 and R D2 is an alkyl group having 4 to 14 carbon atoms).

[0126] [Chemical Formula 19]

[0127]

[0128] [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.]

[0129] [Chemical formula 20]

[0130]

[0131] [In formula (F), R F1 and R F2 each independently represent an alkyl group having 4 to 14 carbon atoms.]

[0132] [Chemical formula 21]

[0133]

[0134] [In formula (G), R G represents an alkyl group having 7 or 10 to 18 carbon atoms.]

[0135] In the above formulas (A), (C), (D), and (E), the halogen atom means a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. As preferred examples, a fluorine atom, a chlorine atom, and a bromine atom can be cited.

[0136] In the above formulas (A) to (D), examples of the alkyl group having 1 to 14 carbon atoms include linear or branched alkyl groups having 1 to 14 carbon atoms such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a 2-methylbutyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a 1-ethylbutyl group, a 2-ethylbutyl group, a 1,1-dimethylbutyl group, a 2,2-dimethylbutyl group, a 3,3-dimethylbutyl group, and a 1-ethyl-1-methylpropyl group. As the alkyl group having 1 to 14 carbon atoms, an alkyl group having 1 to 12 carbon atoms is preferred, and an alkyl group having 1 to 8 carbon atoms is more preferred.

[0137] In the above formula (A), examples of the alkyl group having 1 to 4 carbon atoms include linear or branched alkyl groups having 1 to 4 carbon atoms such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. As the alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 2 carbon atoms is preferred, and an alkyl group having 1 carbon atom is more preferred.

[0138] In the above formulas (A) to (D) and (F), examples of the alkyl group having 4 to 14 carbon atoms include linear or branched alkyl groups having 4 to 14 carbon atoms such as n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 1-ethyl-1-methylpropyl. As the alkyl group having 4 to 14 carbon atoms, an alkyl group having 4 to 12 carbon atoms is preferred, and an alkyl group having 4 to 8 carbon atoms is more preferred.

[0139] In the above formula (E), examples of the alkyl group having 4 to 18 carbon atoms include linear or branched alkyl groups such as n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 1-ethyl-1-methylpropyl. As the alkyl group having 4 to 18 carbon atoms, an alkyl group having 4 to 12 carbon atoms is preferred, and an alkyl group having 8 to 12 carbon atoms is more preferred.

[0140] In the above formula (G), examples of the alkyl group having 7 to 18 carbon atoms include linear or branched alkyl groups having 7 to 18 carbon atoms such as n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, 3,3-dimethylpentyl. As the alkyl group having 7 to 18 carbon atoms, an alkyl group having 11 to 18 carbon atoms is preferred, and an alkyl group having 15 to 18 carbon atoms is more preferred.

[0141] <Compound of General Formula (A)>

[0142] [Chemical Formula 22]

[0143]

[0144] For the compound of general formula (A), in formula (A),

[0145] X A is nitro,

[0146] Y A represents a halogen atom,

[0147] R A1 、R A2 and R A3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein R A1 、RA2 and R A3 at least one of which is an alkyl group having 4 to 14 carbon atoms),

[0148] R A4 represents an alkyl group having 1 to 4 carbon atoms.

[0149] The compound of the above formula (A) is a blue dye compound.

[0150] In the above formula (A), from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., Y A is preferably a bromine atom.

[0151] In addition, in the above formula (A),

[0152] from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., preferably:

[0153] R A1 、R A2 and R A3 are each independently an alkyl group having 4 to 14 carbon atoms, or

[0154] 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

[0155] R A3 is an alkyl group having 4 to 14 carbon atoms and R A1 and R A2 are each independently an alkyl group having 1 to 4 carbon atoms.

[0156] In addition, in the above formula (A),

[0157] from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., preferably:

[0158] Y A is a bromine atom,

[0159] and R A1 、R A2 and R A3 are each independently an alkyl group having 4 to 14 carbon atoms, or

[0160] 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

[0161] R A3 is an alkyl group having 4 to 14 carbon atoms and R A1 and R A2Each is independently an alkyl group having 1 to 4 carbon atoms.

[0162] <Compound of general formula (B)>

[0163] [Chemical formula 23]

[0164]

[0165] For the compound of general formula (B), in formula (B),

[0166] R B1 、R B2 and R B3 each independently represents an alkyl group having 1 to 14 carbon atoms. Among them, R B1 、R B2 and R B3 at least one of them is an alkyl group having 4 to 14 carbon atoms.

[0167] The compound of the above formula (B) is a blue or purple dye compound.

[0168] In the above formula (B),

[0169] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., preferably:

[0170] 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

[0171] 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.

[0172] <Compound of general formula (C)>

[0173] [Chemical formula 24]

[0174]

[0175] For the compound of general formula (C), in formula (C),

[0176] X C and Y C 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,

[0177] R C1 , R C2 and R C3 Each independently represents an alkyl group having 1 to 14 carbon atoms (wherein R C1 , R C2 and R C3 At least one of them is an alkyl group having 4 to 14 carbon atoms).

[0178] The compound of the above formula (C) is a red or purple dye compound.

[0179] In the above formula (C),

[0180] From the perspectives of dyeing concentration, light fastness, sublimation fastness, etc.

[0181] X C and Y C Preferably, it represents 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, and a hydrogen atom and a hydrogen atom.

[0182] In the above formula (C),

[0183] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., preferred are:

[0184] X C and Y C represents 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, and a hydrogen atom and a hydrogen atom,

[0185] And R C1 , R C2 and R C3 are independently an alkyl group having 4 to 14 carbon atoms, or

[0186] R C1 and R C2 are independently an alkyl group having 4 to 14 carbon atoms and R C3 is an alkyl group having 1 to 4 carbon atoms, or

[0187] R C3 is an alkyl group having 4 to 14 carbon atoms and R C1 and R C2 Each independently represents an alkyl group having 1 to 4 carbon atoms.

[0188] <Compound of Formula (D)>

[0189] [Chemical formula 25]

[0190]

[0191] For the compound of general formula (D), in formula (D), X D and Y D each independently represents a hydrogen atom, a halogen atom or a cyano group,

[0192] R D1 represents an alkyl group having 1 to 14 carbon atoms,

[0193] R D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted by CN (wherein at least one of R D1 and R D2 is an alkyl group having 4 to 14 carbon atoms).

[0194] The compound of the above formula (D) is an orange or red dye compound.

[0195] In the above formula (D),

[0196] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., preferably:

[0197] X D represents a hydrogen atom, a chlorine atom or a bromine atom,

[0198] Y D represents a hydrogen atom, a chlorine atom, a bromine atom or a cyano group.

[0199] In addition, in the above formula (D), preferably:

[0200] X D and Y D each independently represents a hydrogen atom, a halogen atom or a cyano group,

[0201] R D1 represents an alkyl group having 4 to 14 carbon atoms,

[0202] R D2 represents an alkyl group having 4 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted by CN.

[0203] <Compound of general formula (E)>

[0204] [Chemical formula 26]

[0205]

[0206] For the compound of general formula (E), in formula (E), X E and Y E each independently represents a halogen atom, and R E represents an alkyl group having 4 to 18 carbon atoms.

[0207] The compound of the above formula (E) is an orange dye compound.

[0208] In the above formula (E),

[0209] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc.,

[0210] X E and Y E preferably represent a chlorine atom.

[0211] In the above formula (E),

[0212] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc.,

[0213] R E is preferably an alkyl group having 4 to 12 carbon atoms.

[0214] In the above formula (E),

[0215] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., preferably:

[0216] X E and Y E represent a chlorine atom,

[0217] R E is an alkyl group having 4 to 12 carbon atoms.

[0218] <Compound of general formula (F)>

[0219] [Chemical formula 27]

[0220]

[0221] For the compound of general formula (F), in formula (F), R F1 and R F2 each independently represent an alkyl group having 4 to 14 carbon atoms.

[0222] The compound of the above formula (F) is a purple dye compound.

[0223] In the above formula (F),

[0224] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., preferably:

[0225] R F1 and R F2 each independently represent an alkyl group having 4 to 12 carbon atoms.

[0226] <Compound of general formula (G)>

[0227] [Chemical formula 28]

[0228]

[0229] For the compound of general formula (G), in formula (G), R G represents an alkyl group having 7 carbon atoms or 10 to 18 carbon atoms.

[0230] The compound of the above formula (G) is a yellow dye compound.

[0231] In the above formula (G),

[0232] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc.,

[0233] R G is preferably an alkyl group having 11 to 18 carbon atoms.

[0234] <Method for Producing Compound of General Formula (A)>

[0235] The method for producing the compound represented by the above formula (A) will be described.

[0236] [Chemical Formula 29]

[0237]

[0238] The compound represented by the above formula (A) is obtained by coupling a diazo compound of a 4-nitroaniline derivative represented by formula (a-D) (in formula (a-D), X A is nitro, Y A represents a halogen atom) with a compound represented by formula (a-C) (in formula (a-C), R A1 , R A2 and R A3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein 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).

[0239] (i) Diazotization of the compound of formula (a-D)

[0240] First, the compound of formula (a-D) is diazotized with a nitrosating agent or nitrosyl sulfuric acid in an inorganic acid or organic carboxylic acid and in the presence of water added as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. In addition, examples of the inorganic acid include hydrochloric acid, phosphoric acid, and sulfuric acid, with sulfuric acid being preferred. The nitrosating agent used is a nitrite of an alkali metal, such as sodium nitrite in solid state or aqueous solution state.

[0241] The reaction temperature of diazotization is preferably -10 to 40 °C, more preferably 0 to 40 °C.

[0242] It should be noted that the compound represented by formula (a-D) is generally widely used as a raw material for azo disperse dyes.

[0243] (ii) Coupling with the compound of formula (a-C)

[0244] In a solution or suspension of the compound represented by formula (a-C) in an alcohol (such as methanol), for example, a solution of the diazo compound of the above formula (a-D) is added in the temperature range of -5 to 10 °C to obtain the compound represented by the above formula (A).

[0245] The pH of the solution or suspension of the compound represented by formula (a-C) is preferably weakly acidic, and sometimes it is advantageous to add a buffer such as triethylamine or sodium acetate in the coupling reaction.

[0246] The water content of the compound of general formula (A) is only required to be within the range where an aqueous dispersion can be prepared, for example, adjusted to 60% by mass or less, preferably 40% by mass or less for use in dyeing.

[0247] (iii) Manufacturing method of the compound of formula (a-C)

[0248] The compound of formula (a-C) as a raw material can be manufactured as follows.

[0249] [Chemical formula 30]

[0250]

[0251] Using N,N-dimethylformamide (DMF) as a solvent, make R A3 -COX (R A3 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) react with the compound represented by formula (a-C1) (in formula (a-C1), R A4 represents an alkyl group having 1 to 4 carbon atoms) to obtain the compound represented by formula (a-C2).

[0252] Then, the compound represented by formula (a-C2) is nitrated with concentrated nitric acid and concentrated sulfuric acid to obtain the compound represented by formula (a-C3).

[0253] The compound represented by formula (a-C3) is reduced with tin in hydrochloric acid-acidic alcohol (such as methanol) to obtain the compound represented by formula (a-C4).

[0254] Using DMF as a solvent, make R A1 -X and R A2 -X (R A1and R A2 The reaction of a haloalkyl represented by (each independently represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) with the compound represented by formula (a-C4) gives formula (a-C).

[0255] Alternatively, R A1 -X (R A1 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) can be reacted with the compound represented by formula (a-C4), and then R A2 (R A2 represents an alkyl group having 1 to 14 carbon atoms) can be introduced according to a known reaction. For example, (R A2 )2SO4 can also be used to introduce R A2 .

[0256] <Method for producing the compound of general formula (B)>

[0257] The method for producing the compound represented by the above formula (B) will be described.

[0258] [Chemical formula 31]

[0259]

[0260] The compound represented by the above formula (B) is obtained by coupling a diazo compound of 3-amino-5-nitro-2,1-benzisothiazole represented by formula (b-D) with a compound represented by formula (b-C) (in formula (b-C), R B1 , R B2 and R B3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms).).

[0261] (i) Diazotization of the compound of formula (b-D)

[0262] First, the compound of formula (b-D) is diazotized with a nitrosating agent or nitrosyl sulfuric acid in an inorganic acid or organic carboxylic acid and in the presence of water added as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. In addition, examples of the inorganic acid include hydrochloric acid, phosphoric acid, and sulfuric acid, with sulfuric acid being preferred. Examples of the nitrosating agent used are nitrites of alkali metals, such as sodium nitrite in solid state or aqueous solution state.

[0263] The reaction temperature for diazotization is preferably -10 to 15 °C, more preferably -5 to 10 °C.

[0264] It should be noted that the compound represented by formula (b-D) is generally widely used as a raw material for azo disperse dyes.

[0265] (ii) Coupling with the compound of formula (b-C)

[0266] In a solution or suspension of the compound represented by formula (b-C) in an alcohol (such as methanol), for example, a solution of the diazo compound of the above formula (b-D) is added within a temperature range of -5 to 10 °C to obtain the compound represented by the above formula (B).

[0267] The pH of the solution or suspension of the compound represented by formula (b-C) is preferably weakly acidic, and it is sometimes advantageous to add a buffer such as triethylamine or sodium acetate in the coupling reaction.

[0268] The water content of the compound of general formula (B) is within the range where an aqueous dispersion can be produced, for example, adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

[0269] (iii) Method for producing the compound of formula (b-C)

[0270] The compound of formula (b-C) as a raw material can be produced as follows.

[0271] [Chemical formula 32]

[0272]

[0273] Using DMF as a solvent, reacting R B3 -COX (where R B3 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) with m-nitroaniline to obtain the compound represented by formula (b-C1).

[0274] Next, the compound represented by formula (b-C1) is reduced by tin in hydrochloric acid-acidic alcohol (such as methanol) to obtain the compound represented by formula (b-C2).

[0275] Using DMF as a solvent, reacting R B1 -X and R B2 -X (where R B1 and R B2 each independently represent an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) with the compound represented by formula (b-C2) to obtain formula (b-C).

[0276] Alternatively, it is also possible to use R B1 -X (where R B1A halogenated hydrocarbon represented by (wherein the alkyl group has 1 to 14 carbon atoms and X represents a halogen atom) is reacted with a compound represented by formula (b-C2), and then R is introduced according to a known reaction. B2 (R B2 represents an alkyl group having 1 to 14 carbon atoms). For example, (R B2 )2SO4 can also be used to introduce R. B2 .

[0277] <Method for producing the compound of general formula (C)>

[0278] The method for producing the compound represented by the above formula (C) will be described.

[0279] [Chemical formula 33]

[0280]

[0281] The compound represented by the above formula (C) is obtained by coupling a diazo compound of a 4-nitroaniline derivative represented by formula (c-D) (in formula (c-D), X C and Y C 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, and a hydrogen atom and a hydrogen atom) with a compound represented by formula (c-C) (in formula (c-C), R C1 , R C2 and R C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 , R C2 and R C3 is an alkyl group having 4 or more carbon atoms)).

[0282] (i) Diazotization of the compound of formula (c-D)

[0283] First, the compound represented by formula (c-D) is diazotized with a nitrosating agent or nitrosylsulfuric acid in an inorganic acid or organic carboxylic acid and in the presence of water added as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. Examples of the inorganic acid include hydrochloric acid, phosphoric acid, and sulfuric acid, with sulfuric acid being preferred. Examples of the nitrosating agent used are nitrites of alkali metals, such as sodium nitrite in solid state or aqueous solution state.

[0284] The diazotization temperature is preferably -10 to 40 °C, more preferably 0 to 35 °C.

[0285] It should be noted that the compound represented by formula (c-D) is generally widely used as a raw material for azo disperse dyes.

[0286] (ii) Coupling with the compound of formula (c-C)

[0287] In a solution or suspension of the compound represented by formula (c-C) in an alcohol (such as methanol), for example, a solution of the diazo compound of the above formula (c-D) is added in the temperature range of -5 to 10 °C to obtain the compound represented by the above formula (C).

[0288] The pH of the solution or suspension of the compound represented by formula (c-C) is preferably weakly acidic, and it is sometimes advantageous to add a buffer such as triethylamine or sodium acetate.

[0289] The water content of the compound of general formula (C) is only required to be in the range where an aqueous dispersion can be produced. For example, it is adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

[0290] (iii) Method for producing the compound of formula (c-C)

[0291] The compound of formula (c-C) as a raw material can be produced as follows.

[0292] [Chemical formula 34]

[0293]

[0294] Using DMF as a solvent, reacting R C3 -COX (R C3 represents an alkyl group having 1 to 14 carbon atoms, and X is a halogen atom) with m-nitroaniline to obtain the compound represented by formula (c-C1).

[0295] Then, the compound represented by formula (c-C1) is reduced by tin in hydrochloric acid-containing alcohol (such as methanol) to obtain the compound represented by formula (c-C2).

[0296] Using DMF as a solvent, reacting R C1 -X and R C2 -X (R C1 and R C2 each independently represents an alkyl group having 1 to 14 carbon atoms, and X is a halogen atom) with the compound represented by formula (c-C2) to obtain formula (c-C).

[0297] Alternatively, R C1 -X (R C1 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) can be reacted with the compound represented by formula (c-C2), and then, according to a known reaction, R C2 (R C2 represents an alkyl group having 1 to 14 carbon atoms) can be introduced. For example, (R C2) Introduce R with 2SO4 C2 .

[0298] <Method for manufacturing the compound of general formula (D)>

[0299] The method for manufacturing the compound represented by the above formula (D) will be described.

[0300] [Chemical formula 35]

[0301]

[0302] The compound represented by formula (D) is obtained by coupling a diazo compound of a 4-nitroaniline derivative represented by formula (d-D) (in formula (d-D), X D and Y D each independently represent a hydrogen atom, a halogen atom or a cyano group) with a compound represented by formula (d-C) (in formula (d-C), 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 an alkyl group having 1 to 14 carbon atoms obtained by being substituted with CN. Among them, at least one of R D1 and R D2 is an alkyl group having 4 to 14 carbon atoms.).

[0303] (i) Diazotization of the compound of formula (d-D)

[0304] First, the compound represented by formula (d-D) is diazotized with a nitrosating agent or nitrosylsulfuric acid in an inorganic acid or an organic carboxylic acid and in the presence of water added as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. In addition, examples of the inorganic acid include hydrochloric acid, phosphoric acid and sulfuric acid, and sulfuric acid is preferred. Examples of the nitrosating agent used are nitrites of alkali metals, such as sodium nitrite in solid state or aqueous solution state.

[0305] The diazotization temperature is preferably -10 to 40 °C, more preferably 0 to 30 °C.

[0306] The compound represented by formula (d-D) is generally widely used as a raw material for azo disperse dyes.

[0307] (ii) Coupling with the compound of formula (d-D)

[0308] In a solution or suspension of the compound represented by formula (d-C) in an alcohol (such as methanol), for example, a solution of the diazo compound of formula (d-D) is added in the temperature range of -5 to 10 °C to obtain the compound represented by the above formula (D).

[0309] The pH of the compound solution or suspension represented by formula (d-C) is preferably weakly acidic, and it is sometimes advantageous to add a buffer such as triethylamine or sodium acetate.

[0310] The water content of the compound of general formula (D) only needs to be in the range where an aqueous dispersion can be produced, and for example, it is adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

[0311] (iii) Method for producing the compound of formula (d-C)

[0312] The compound of formula (d-C) as a raw material can be produced as follows.

[0313] [Chemical formula 36]

[0314]

[0315] Using DMF as a solvent, make R D1 -X and R D2 -X (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 obtained by being substituted with CN. Among them, at least one of R D1 and R D2 is an alkyl group having 4 to 14 carbon atoms. X is a halogen atom.) The represented haloalkyl reacts with aniline to obtain formula (d-C).

[0316] Alternatively, it is also possible to make R D1 -X (R D1 represents an alkyl group having 1 to 14 carbon atoms, X represents a halogen atom) The represented halogenated hydrocarbon reacts with aniline, and then according to a known reaction, R D2 (R D2 represents an alkyl group having 1 to 14 carbon atoms) is introduced. For example, (R D2 )2SO4 can be used to introduce R D2 .

[0317] <Method for producing the compound of general formula (E)>

[0318] The method for producing the compound represented by the above formula (E) will be described.

[0319] [Chemical formula 37]

[0320]

[0321] The compound represented by the above formula (E) is obtained by using a 4-nitroaniline derivative represented by formula (e-D) (in formula (e-D), X E and Y EA diazo compound (wherein X represents a halogen atom) is obtained by coupling with a compound represented by formula (e-C) (in formula (e-C), R E represents an alkyl group having 4 to 18 carbon atoms).

[0322] (i) Diazotization of the compound of formula (e-D)

[0323] First, the compound represented by formula (e-D) is diazotized with a nitrosating agent or nitrosylsulfuric acid in an inorganic acid or organic carboxylic acid and in the presence of water added as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. In addition, examples of the inorganic acid include hydrochloric acid, phosphoric acid, and sulfuric acid, with sulfuric acid being preferred. Examples of the nitrosating agent used are nitrites of alkali metals, such as sodium nitrite in solid state or aqueous solution state.

[0324] The diazotization temperature is preferably -10 to 40 °C, more preferably 0 to 30 °C.

[0325] It should be noted that the compound represented by formula (e-D) is generally widely used as a raw material for azo disperse dyes.

[0326] (ii) Coupling with the compound of formula (e-C)

[0327] In a solution or suspension of the compound represented by formula (e-C) in an alcohol (such as methanol), for example, a solution of the above-mentioned diazo compound of formula (e-D) is added in the temperature range of -5 to 10 °C to obtain the compound represented by the above formula (E).

[0328] The pH of the solution or suspension of the compound represented by formula (e-C) is preferably weakly acidic, and it is sometimes advantageous to add a buffer such as triethylamine or sodium acetate.

[0329] The water content of the compound of general formula (E) may be within the range where an aqueous dispersion can be produced, and for example, it is adjusted to 60% by mass or less, preferably 40% by mass or less, for use in dyeing.

[0330] (iii) Method for producing the compound of formula (e-C)

[0331] The compound of formula (e-C) as a raw material can be produced as follows.

[0332] [Chemical formula 38]

[0333]

[0334] Using DMF as a solvent, R E1 -X (R E1A haloalkyl represented by (alkyl having 4 to 18 carbon atoms, and X is a halogen atom) reacts with 2-phenyl-1H-indole represented by formula (e-C1) to obtain formula (e-C).

[0335] <Method for producing a compound of general formula (F)>

[0336] The method for producing the compound represented by the above formula (F) will be described.

[0337] [Chemical formula 39]

[0338]

[0339] The compound represented by the above formula (F) is obtained by coupling a diazo compound of 3-amino-5-nitro-2,1-benzisothiazole represented by formula (f-D) with a compound represented by formula (f-C) (in formula (f-C), R F1 and R F2 each independently represents an alkyl group having 4 to 14 carbon atoms).

[0340] (i) Diazotization of the compound of formula (f-D)

[0341] First, the compound represented by formula (f-D) is diazotized with a nitrosating agent or nitrosylsulfuric acid in an inorganic acid or organic carboxylic acid and in the presence of water added as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. In addition, examples of the inorganic acid include hydrochloric acid, phosphoric acid, and sulfuric acid, with sulfuric acid being preferred. The nitrosating agent used is a nitrite of an alkali metal, such as sodium nitrite in solid state or aqueous solution state.

[0342] The diazotization temperature is preferably -10 to 15 °C, more preferably -5 to 10 °C.

[0343] The compound represented by formula (f-D) is generally widely used as a raw material for azo disperse dyes.

[0344] (ii) Coupling with the compound of formula (f-C)

[0345] In a solution or suspension of an alcohol (such as methanol) of the compound represented by formula (f-C), a solution of the above diazo compound of formula (f-D) is added, for example, in the temperature range of -5 to 10 °C, to obtain the compound represented by the above formula (F).

[0346] The pH of the solution or suspension of the compound represented by formula (f-C) is preferably weakly acidic, and it is sometimes advantageous to add a buffer such as triethylamine or sodium acetate.

[0347] The water content of the compound of the general formula (F) only needs to be within the range where an aqueous dispersion can be produced, and for example, it is adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

[0348] (iii) Method for producing the compound of formula (f-C)

[0349] The compound of formula (f-C) as a raw material can be produced as follows.

[0350] [Chemical formula 40]

[0351]

[0352] Using DMF as a solvent, make R F1 -X and R F2 -X (R F1 and R F2 each independently represents an alkyl group having 4 to 14 carbon atoms, and X is a halogen atom) react with aniline to obtain formula (f-C).

[0353] Alternatively, it is also possible to make R F1 -X (R F1 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) react with aniline, and then, according to a known reaction, introduce R F2 (R F2 represents an alkyl group having 1 to 14 carbon atoms). For example, (R F2 )2SO4 can be used to introduce R F2 .

[0354] <Method for producing the compound of general formula (G)>

[0355] The method for producing the compound represented by the above formula (G) will be described.

[0356] [Chemical formula 41]

[0357]

[0358] The compound represented by formula (G) is obtained by reacting 5-amino-anthra[9,1-cd]isothiazol-6-one represented by formula (g) with R G -COX (R G represents an alkyl group having 7 to 18 carbon atoms, and X is a halogen atom) in an inert solvent such as toluene, xylene, or chlorobenzene.

[0359] The reaction temperature is preferably 80 °C to 140 °C, more preferably 110 to 140 °C.

[0360] The compound represented by formula (g) is generally widely used as a raw material for polycyclic disperse dyes.

[0361] The water content of the compound of the general formula (G) only needs to be within the range where an aqueous dispersion can be produced, and for example, it is adjusted to 60% by mass or less, preferably 40% by mass or less, and used for dyeing.

[0362] <Dye composition>

[0363] The dye composition of the present invention contains at least one of the compounds of the general formulas (A) to (G) and a nonionic dispersant as described above.

[0364] Examples of the nonionic dispersant include polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene aryl phenyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene aryl aryl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene acetylenic glycol, polyvinyl alcohol, polyvinylpyrrolidone, ethylene oxide-propylene oxide copolymer, etc. Among them, it is preferable to use at least one selected from polyoxyethylene alkyl phenyl ether, polyoxyethylene aryl phenyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene aryl aryl ether, and ethylene oxide-propylene oxide copolymer, more preferably at least one selected from polyoxyethylene aryl phenyl ether, polyoxyethylene aryl aryl ether, and ethylene oxide-propylene oxide copolymer, and still more preferably at least one selected from polyoxyethylene aryl phenyl ether and ethylene oxide-propylene oxide copolymer.

[0365] There is no limitation on the polymerization form of the above ethylene oxide-propylene oxide copolymer, and it can be any of a random polymer, a block polymer, etc.

[0366] It should be noted that in order to use the dye composition not as a liquid aqueous dispersion but as a powder form by spray drying or the like through a nonionic dispersant, it is preferable to contain both polyoxyethylene aryl phenyl ether and ethylene oxide-propylene oxide copolymer in the nonionic dispersant.

[0367] For the purpose of maintaining good dispersion stability of the compound represented by the formulas (A) to (G), the amount of the nonionic dispersant used is preferably 20 to 200% by mass, more preferably 20 to 100% by mass, based on the mass of the compound represented by the formulas (A) to (G).

[0368] In the dye composition of the present invention, within the range that does not prevent the achievement of the object of the present invention, a viscosity modifier, a surface tension modifier, a pH modifier, a humectant, a solubilizer, a chelating agent, a preservative, a mildew preventive, an antifoaming agent, etc. may be added as needed.

[0369] The dye composition of the present invention may further contain additives. Examples of the above additives include color formers, dispersants, fillers, stabilizers, plasticizers, nucleating agents, modifiers, foaming agents, ultraviolet absorbers, light stabilizers, antioxidants, antibacterial agents, mildewproofing agents, antistatic agents, flame retardants, inorganic fillers, and elastomers for improving impact resistance, etc.

[0370] From the viewpoints of ease of handling, safety, etc., the dye composition of the present invention is preferably an aqueous dispersion. Since the compounds represented by formulas (A) to (G) have high lipophilicity, in order to obtain a dye composition in the form of an aqueous dispersion, it is necessary to use the above dispersant in combination and perform fine particle dispersion treatment with a dispersing machine such as a bead mill.

[0371] It should be noted that the dye composition of the present invention may be either a liquid aqueous dispersion in a state obtained by finely dispersing the compounds represented by formulas (A) to (G) in an aqueous dispersion medium using a nonionic dispersant, or a powder form in which the dispersion medium of the above liquid aqueous dispersion is removed by spray drying or the like, but from the viewpoint of the product life, it is preferably in powder form.

[0372] The content of the compounds represented by formulas (A) to (G) in the dye composition of the present invention is within a range that ensures ease of handling during dyeing, preferably 5 to 40% by mass, more preferably 10 to 30% by mass.

[0373] The following methods are preferably listed as the manufacturing method of the dye composition of the invention.

[0374] (1) A dispersant solution is prepared by adding a nonionic dispersant, various additives such as a viscosity modifier as required, to water and stirring.

[0375] (2) The compounds represented by formulas (A) to (G) are added to the dispersant solution in (1) and stirred to prepare an aqueous slurry.

[0376] (3) The fine particle dispersion treatment of the aqueous slurry in (2) is carried out with a wet dispersing machine such as a bead mill until the volume median diameter of the compounds represented by formulas (A) to (G) becomes 1.0 μm or less, preferably 0.5 μm or less.

[0377] (4) Water is added to the fine particle dispersion treatment product in (3) to adjust the concentration, and a liquid aqueous dispersion is obtained.

[0378] (5) Various additives such as a dispersant are added to the liquid aqueous dispersion in (4) as required and stirred, and the dispersion medium is removed by spray drying or the like to obtain a powder-form dye composition.

[0379] The obtained (4) liquid aqueous dispersion or (5) powdery dye composition can be used to perform aqueous dyeing of fibers by methods such as the dipping method or the printing method.

[0380] The compounds of general formulas (A) to (G) contained in the dye composition for dyeing the fibers of the present invention have blue, purple, red, orange, or yellow. The above dye composition may also contain a single compound or two or more compounds of general formulas (A) to (G). When the above dye composition contains two or more compounds of general formulas (A) to (G), dyes for dyeing fibers into various hues or black can be obtained.

[0381] For the dye composition for dyeing fibers black, it is preferably to contain: at least one purple or blue compound containing one or more 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 containing one or more selected from the group consisting of the compound of general formula (C) and the compound 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); more preferably to contain: at least one purple or blue compound containing one or more 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), the red compound of general formula (C), and at least one orange compound containing one or more selected from the group consisting of the compound of general formula (D) and the compound of general formula (E); further preferably to contain: the blue compound of general formula (A), the red compound of general formula (C), and the orange compound of general formula (D).

[0382] Table 1

[0383] Dye composition for dyeing fibers black

[0384]

[0385] As the composition of the compounds in the above dye composition for dyeing fibers black, it is preferred that: the mixing ratio of the above purple or blue compound is in the range of 30 to 70% by mass, the mixing ratio of the above red compound is in the range of 5 to 25% by mass, and the mixing ratio of the above yellow or orange compound is in the range of 15 to 55% by mass; more preferably, the mixing ratio of the above purple or blue compound is in the range of 40 to 60% by mass, the mixing ratio of the above red compound is in the range of 5 to 25% by mass, and the mixing ratio of the above yellow or orange compound is in the range of 25 to 45% by mass.

[0386] Table 2

[0387] Regarding the mixing ratio

[0388]

[0389] Examples of the fiber as the material to be dyed in the present invention include polyester fiber, polyolefin fiber, acrylonitrile-based fiber, etc., and polyolefin fiber is preferred.

[0390] Examples of the above polyolefin fiber include fibers formed from polymers selected from homopolymers of α-olefins such as propylene, ethylene, 1-butene, 3-methyl-1-butene, 4-methyl-1-pentene, 1-octene, copolymers of these α-olefins, or copolymers with other unsaturated monomers copolymerizable with these α-olefins. In addition, examples of the copolymer types include block copolymers, random copolymers, graft copolymers, etc. Specific examples of the above polymers include polypropylene-based resins such as propylene homopolymer, propylene-ethylene block copolymer, propylene-ethylene random copolymer, propylene-ethylene-(1-butene) copolymer, polyethylene-based resins such as low-density 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-pentene, etc.

[0391] The above polymers can also be used alone or in combination of two or more to form polyolefin fibers.

[0392] As the above polyolefin fiber, it is preferably formed from a polypropylene-based resin and / or a polyethylene-based resin, and more preferably formed from a polypropylene-based resin.

[0393] The shape of the above polyolefin fiber can be any of block (molded product, etc.), film, fiber (fabric (woven fabric, knitted fabric, non-woven fabric, etc.), yarn (filament yarn, fine yarn, slit film yarn, split film yarn, etc.)), etc., and fiber shape is preferred.

[0394] The above polyolefin fiber can also be a fiber formed by blending, joining, etc. other polymer components with a polypropylene resin and / or a polyethylene resin. The above polyolefin fiber can also be a fiber obtained by blending, mixing, etc. other fibers such as polyester in polypropylene fiber.

[0395] <Dyeing method of fiber>

[0396] As described above, the present invention provides a method, which is a dyeing method of fiber, comprising a step of subjecting the fiber to aqueous dyeing using the dye composition of the present invention.

[0397] In addition, the above dyeing process is preferably at least one selected from the group consisting of dip dyeing, printing and dyeing, inkjet dyeing, transfer dyeing, and continuous dyeing, more preferably at least one selected from dip dyeing and printing and dyeing, and still more preferably printing and dyeing. When the above dyeing process is dip dyeing, the above dyeing process is carried out, for example, by immersing the object to be dyed in the dye composition of the present invention under pressure, preferably at 80°C to 130°C, more preferably at 90°C to 120°C, and preferably for 30 minutes to 60 minutes.

[0398] When the above fiber is polyolefin, the above dyeing process is preferably carried out at 80°C to 130°C. The above dyeing process is preferably carried out for 30 minutes to 60 minutes.

[0399] When the above fiber is polypropylene, the above dyeing process is preferably carried out at 110°C to 130°C. The above dyeing process is preferably carried out for 30 minutes to 60 minutes.

[0400] When the above fiber is polyethylene, the above dyeing process is preferably carried out at 90°C to 110°C. The above dyeing process is preferably carried out for 30 minutes to 60 minutes.

[0401] When the above dyeing process is printing and dyeing, the above dyeing process is carried out, for example, by printing a printing and dyeing paste prepared by mixing the dye composition of the present invention in a paste such as a natural paste (such as guar gum, etc.) or a processing paste (such as carboxymethyl cellulose, etc.) onto the object to be dyed, and then, for example, performing steam treatment at 90°C to 200°C for 1 minute to 20 minutes, or dry heat treatment for 20 seconds to 5 minutes.

[0402] When the above fiber is polyolefin, the above dyeing process is preferably carried out at 80°C to 130°C for 1 minute to 10 minutes of steam treatment.

[0403] When the above fiber is polypropylene, the above dyeing process is preferably carried out at 110°C to 130°C for 1 minute to 10 minutes of steam treatment.

[0404] When the above fiber is polyethylene, the above dyeing process is preferably carried out at 90°C to 110°C for 1 minute to 10 minutes of steam treatment.

[0405] When the above dyeing process is inkjet dyeing, the above dyeing process is carried out, for example, by adding a low-volatility water-soluble organic solvent such as glycerol or diethylene glycol to the liquid dye composition of the present invention to prepare an ink for inkjet printing, printing it onto a cloth, fiber, or the formed fiber that has been previously given a paste, etc. by padding, etc. using an inkjet printer, and then, for example, performing steam treatment at 90°C to 200°C for 1 minute to 20 minutes, or dry heat treatment for 20 seconds to 5 minutes.

[0406] In the case of impregnation, the concentration of the dye of the present invention relative to the above-mentioned fiber is, for example, 0.001% o.m.f. to 10% o.m.f., preferably 0.001% o.m.f. to 5% o.m.f. It should be noted that o.m.f. means on the mass of fiber (relative to the fiber mass).

[0407] In the case of printing and dyeing, the concentration of the dye of the present invention relative to the above-mentioned printing paste is, for example, 0.001% o.m.p. to 5% o.m.p., preferably 0.001% o.m.p. to 2% o.m.p. It should be noted that o.m.p. means on the mass of paste (relative to the paste mass).

[0408] The present invention provides a fiber dyed by the dyeing method of the present invention. As uses of the above-mentioned fiber, for example, clothing items such as clothes, underwear, hats, socks, gloves, sportswear, etc., vehicle interior materials such as seat covers, carpets, curtains, floor mats, sofa covers, cushion covers, etc. for interior decoration can be cited.

[0409] Hereinafter, examples will be given to further specifically illustrate the present invention, but the solutions of the present invention are not limited to these.

[0410] [Examples]

[0411] (Synthesis Example 1)

[0412] [Synthesis of Blue Dye Compound (A-1)]

[0413] The blue dye compound (A-1) is produced according to the following scheme.

[0414] [Chemical Formula 42]

[0415]

[0416] 1-A. Synthesis of Coupling Agent Compound (C1) and Preparation of Coupling Agent Component Solution

[0417] (Step 1)

[0418] Dissolve p-anisidine (purchased as a commercial product) (24.6 g) in DMF (35 g), and add pyridine (19 g) dropwise. After adding n-octanoyl chloride (purchased as a commercial product) (34.2 g) dropwise, heat to 110°C and stir for 1 hour. After cooling to room temperature, add 2M hydrochloric acid (150 ml) to precipitate. Filter out this mixture, wash with water, and dry to obtain N-(4-methoxyphenyl)octanamide (53.1 g, yield 106.5%) represented by the following formula (C1a) as a crude product.

[0419] [Chemical Formula 43]

[0420]

[0421] (Step 2)

[0422] To concentrated sulfuric acid (30 g) cooled to 5 °C, N-(4-methoxyphenyl)octanamide (12.5 g) obtained in the above Step 1 was slowly added in the range of 5 to 10 °C. After concentrated nitric acid (4.57 g) was added dropwise to this mixture over 1 hour in the range of 5 to 10 °C, the mixture was stirred at the same temperature for 1 hour. The reaction mixture was purified in ice water (150 g), and ethyl acetate (100 g) was added to extract the organic phase. After the extract was washed with saturated brine, the solvent was removed by distillation under reduced pressure, whereby N-(3-nitro-4-methoxyphenyl)octanamide (16.9 g, yield 114.8%) represented by the following formula (C1b) was obtained as a crude product.

[0423] [Chemical formula 44]

[0424]

[0425] (Step 3)

[0426] A mixture of N-(3-nitro-4-methoxyphenyl)octanamide (16.9 g) obtained in the above Step 2, 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 the reaction mixture was cooled 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, whereby N-(3-amino-4-methoxyphenyl)octanamide (9.19 g, yield 69.5%) represented by the following formula (C1c) was obtained.

[0427] [Chemical formula 45]

[0428]

[0429] (Step 4)

[0430] The mixture of N-(3-amino-4-methoxyphenyl)octanamide (13.2 g), triethylamine (15 g), DMF (15 g), and 1-bromooctane (purchased as a commercial product) (38.6 g) obtained in the above step 3 was heated to 120 °C and stirred at the same temperature for 3 hours to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]octanamide represented by the following formula (C1). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C1) was obtained.

[0431] [Chemical formula 46]

[0432]

[0433] 1-B. Preparation of diazo component solution

[0434] (Step 5)

[0435] 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 slowly added in the range of 25 to 30 °C. By stirring the mixture at 30 to 40 °C for 2 hours, a diazo component solution was obtained.

[0436] [Chemical formula 47]

[0437]

[0438] 1-C. Synthesis of blue dye compound (A-1) by coupling reaction

[0439] (Step 6)

[0440] In the range of 0 to 10 °C, the diazo component solution obtained in the above step 5 was added dropwise to the coupling agent component solution obtained in the above step 4 over 2 hours, and triethylamine (84 g) was appropriately added to the coupling agent component solution to carry out a coupling reaction. After stirring the mixture in the range of 0 to 10 °C for 30 minutes, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less to obtain the blue dye compound represented by the following formula (A-1) (5.93 g, yield 15.5%). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 761 (M + )).

[0441] [Chemical formula 48]

[0442]

[0443] (Synthesis Example 2)

[0444] [Synthesis of Blue Dye Compound (A-2)]

[0445] The blue dye compound (A-2) is produced according to the following scheme.

[0446] [Chemical Formula 49]

[0447]

[0448] 2-A. Synthesis of Coupling Agent Compound (C2) and Preparation of Coupling Agent Component Solution

[0449] (Step 1)

[0450] In Step 1 of Synthesis Example 1, valeryl chloride (25.3 g) was used instead of n-octanoyl chloride, and otherwise, the same operations as in Steps 1 to 4 of Synthesis Example 1 were carried out to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]pentanamide represented by the following formula (C2). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C2) was obtained.

[0451] [Chemical Formula 50]

[0452]

[0453] 2-B. Synthesis of Blue Dye Compound (A-2) by Coupling Reaction

[0454] (Step 2)

[0455] As the coupling agent component solution, the compound of formula (C2) obtained in Step 1 was used instead of the compound of formula (C1), and otherwise, the same operations as in Steps 5 and 6 of Synthesis Example 1 were carried out to obtain the blue dye compound represented by the following formula (A-2) (8.03 g, yield 22.3%). The structure of this blue dye compound was confirmed by LCMS analysis (m / z 719 (M + ))

[0456] [Chemical Formula 51]

[0457]

[0458] (Synthesis Example 3)

[0459] [Synthesis of Blue Dye Compound (A-3)]

[0460] The blue dye compound (A-3) is produced according to the following scheme.

[0461] [Chemical Formula 52]

[0462]

[0463] 3-A. Synthesis of Coupling Agent Compound (C3) and Preparation of Coupling Agent Component Solution

[0464] (Step 1)

[0465] In Step 1 of Synthesis Example 1, propionyl chloride (19.4 g) was used instead of n-octanoyl chloride, and the same operations as in Steps 1 to 4 of Synthesis Example 1 were carried out to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]propanamide represented by the following formula (C3). By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C3) was obtained.

[0466] [Chemical Formula 53]

[0467]

[0468] 3-B. Synthesis of Blue Dye Compound (A-3) by Coupling Reaction

[0469] (Step 2)

[0470] As the coupling agent component solution, the compound of formula (C3) obtained in Step 1 was used instead of the compound of formula (C1), and the same operations as in Steps 5 and 6 of Synthesis Example 1 were carried out to obtain a blue dye compound (5.85 g, yield 16.9%) represented by the following formula (A-3). The structure of the above blue dye compound was confirmed by LCMS analysis (m / z 691 (M + ))

[0471] [Chemical Formula 54]

[0472]

[0473] (Synthesis Example 4)

[0474] [Synthesis of Blue Dye Compound (A-4)]

[0475] The blue dye compound (A-4) was manufactured according to the following scheme.

[0476] [Chemical Formula 55]

[0477]

[0478] 4-A. Synthesis of Coupling Agent Compound C4 and Preparation of Coupling Agent Component Solution

[0479] (Step 1)

[0480] In Step 1 of Synthesis Example 1, 2-ethylhexanoyl chloride (34.2 g) was used instead of n-octanoyl chloride, and the same operations as in Steps 1 to 4 of Synthesis Example 1 were carried out to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]-2-ethylhexanamide represented by the following formula (C4). By adding methanol (30 g) to this reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C4) was obtained.

[0481] [Chemical Formula 56]

[0482]

[0483] 4-B. Synthesis of Blue Dye Compound (A-4) by Coupling Reaction

[0484] (Step 2)

[0485] As the coupling agent component solution, the compound of formula (C4) obtained in Step 1 was used instead of the compound of formula (C1), and the same operations as in Steps 5 and 6 of Synthesis Example 1 were carried out to obtain the blue dye compound (9.63 g, yield 25.3%) represented by the following formula (A-4). The structure of the above blue dye compound was confirmed by LCMS analysis (m / z 761 (M + )).

[0486] [Chemical Formula 57]

[0487]

[0488] (Synthesis Example 5)

[0489] [Synthesis of Blue Dye Compound (A-5)]

[0490] The blue dye compound (A-5) was produced according to the following scheme.

[0491] [Chemical Formula 58]

[0492]

[0493] 5-A. Synthesis of Coupling Agent Compound C5 and Preparation of Coupling Agent Component Solution

[0494] (Step 1)

[0495] In Step 4 of Synthesis Example 1, N-(3-amino-4-methoxyphenyl)acetamide (purchased as a commercial product) (9.0 g) was used in place of N-(3-amino-4-methoxyphenyl)octanamide, and the operation was the same as in Step 4 of Synthesis Example 1 except for this, to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]acetamide represented by the following formula (C5). By adding methanol (30 g) to this reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C5) was obtained.

[0496] [Chemical Formula 59]

[0497]

[0498] 5-B. Synthesis of Blue Dye Compound (A-5) by Coupling Reaction

[0499] (Step 2)

[0500] As the coupling agent component solution, the compound of formula (C5) obtained in Step 1 was used in place of the compound of formula (C1), and the operation was the same as in Steps 5 and 6 of Synthesis Example 1 except for this, to obtain the blue dye compound represented by the following formula (A-5) (20.3 g, yield 60.0%). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 677 (M + )).

[0501] [Chemical Formula 60]

[0502]

[0503] (Synthesis Example 6)

[0504] [Synthesis of Blue Dye Compound (A-6)]

[0505] The blue dye compound (A-6) was produced according to the following scheme.

[0506] [Chemical Formula 61]

[0507]

[0508] 6-A. Synthesis of Coupling Agent Compound (C6) and Preparation of Coupling Agent Component Solution

[0509] (Step 1)

[0510] In Step 4 of Synthesis Example 1, 1-bromododecane (49.8 g) was used instead of 1-bromooctane, and N-(3-amino-4-methoxyphenyl)acetamide (9.0 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide. Otherwise, the operation was the same as in Step 4 of Synthesis Example 1 to obtain N-[3-(N,N-didodecylamino)-4-methoxyphenyl]acetamide represented by the following formula (C6). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C6) was obtained.

[0511] [Chemical Formula 62]

[0512]

[0513] 6-B. Synthesis of Blue Dye Compound (A-6) by Coupling Reaction

[0514] (Step 2)

[0515] As the coupling agent component solution, the compound of formula (C6) obtained in Step 1 was used instead of the compound of formula (C1). Otherwise, the operation was the same as in Steps 5 and 6 of Synthesis Example 1 to obtain the blue dye compound (19.3 g, yield 48.9%) represented by the following formula (A-6). The structure of the above blue dye compound was confirmed by LCMS analysis (m / z 789 (M + )).

[0516] [Chemical Formula 63]

[0517]

[0518] (Synthesis Example 7)

[0519] [Synthesis of Blue Dye Compound (A-7)]

[0520] The blue dye compound (A-7) was manufactured according to the following scheme.

[0521] [Chemical Formula 64]

[0522]

[0523] 7-A. Synthesis of Coupling Agent Compound C7 and Preparation of Coupling Agent Component Solution

[0524] (Step 1)

[0525] In Step 4 of Synthesis Example 1, 1-bromoethane (27.3 g) was used in place of 1-bromooctane, and otherwise, the operation was the same as in Step 4 of Synthesis Example 1 to obtain N-[3-(N,N-diethylamino)-4-methoxyphenyl]octanamide represented by the following formula (C7). By adding methanol (30 g) to this reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C7) was obtained.

[0526] [Chemical formula 65]

[0527]

[0528] 7-B. Synthesis of blue dye compound (A-7) using a coupling reaction

[0529] (Step 2)

[0530] As the coupling agent component solution, the compound of formula (C7) obtained in Step 1 was used in place of the compound of formula (C1), and otherwise, the operation was the same as in Steps 5 and 6 of Synthesis Example 1 to obtain the blue dye compound represented by the following formula (A-7) (7.71 g, yield 26.0%). The structure of the above blue dye compound was confirmed by LCMS analysis (m / z 593 (M + )).

[0531] [Chemical formula 66]

[0532]

[0533] (Synthesis Example 8)

[0534] [Synthesis of blue dye compound (A-8)]

[0535] The blue dye compound (A-8) was produced according to the following scheme.

[0536] [Chemical formula 67]

[0537]

[0538] 8-A. Synthesis of coupling agent compound C8 and preparation of coupling agent component solution

[0539] (Step 1)

[0540] In Step 1 of Synthesis Example 1, 4-ethoxyaniline (27.4 g) was used in place of p-anisidine, and otherwise, the operation was the same as in Steps 1 to 4 of Synthesis Example 1 to obtain N-[3-(N,N-dioctylamino)-4-ethoxyphenyl]octanamide represented by the following formula (C8). By adding methanol (30 g) to this reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C8) was obtained.

[0541] [Chemical Formula 68]

[0542]

[0543] 8-B. Synthesis of Blue Dye Compound (A-8) Using Coupling Reaction

[0544] (Step 2)

[0545] As the coupling agent component solution, the compound of formula (C8) obtained in Step 1 was used instead of the compound of formula (C1), and the same operations as in Steps 5 and 6 of Synthesis Example 1 were carried out to obtain the blue dye compound shown by the following formula (A-8) (4.50 g, yield 11.6%). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 775 (M + ))

[0546] [Chemical Formula 69]

[0547]

[0548] (Synthesis Example 9)

[0549] [Synthesis of Blue Dye Compound (B-1)]

[0550] The blue dye compound (B-1) was manufactured according to the following scheme

[0551] [Chemical Formula 70]

[0552]

[0553] 9-A. Synthesis of Coupling Agent Compound C9 and Preparation of Coupling Agent Component Solution

[0554] (Step 1)

[0555] 3-Nitroaniline (27.6 g) was used instead of p-anisidine, and the same operations as in Step 1 of Synthesis Example 1 were carried out to obtain N-(3-nitrophenyl)octanamide shown by the following formula (C9a) as a crude product (53.6 g, yield 101.4%).

[0556] [Chemical Formula 71]

[0557]

[0558] (Step 2)

[0559] Using N-(3-nitrophenyl)octanamide (13.2 g) to replace N-(3-nitro-4-methoxyphenyl)octanamide, and otherwise operating in the same manner as in Step 3 of Synthesis Example 1, N-(3-aminophenyl)octanamide represented by the following formula (C9b) was obtained (9.48 g, yield 80.9%).

[0560] [Chemical formula 72]

[0561]

[0562] (Step 3)

[0563] Using N-(3-aminophenyl)octanamide (11.7 g) to replace N-(3-amino-4-methoxyphenyl)octanamide, and otherwise operating in the same manner as in Step 4 of Synthesis Example 1, N-[3-(N,N-dioctylamino)phenyl]octanamide represented by the following formula (C9) was obtained. By adding methanol (30 g) to this reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C9) was obtained.

[0564] [Chemical formula 73]

[0565]

[0566] 9-B. Preparation of the diazo component solution

[0567] (Step 4)

[0568] To a mixture of concentrated sulfuric acid (29 g) and 43% nitrosylsulfuric acid (12.7 g), 3-amino-5-nitro-2,1-benzisothiazole represented by the following formula (D2) (8.15 g) was slowly added in the range of 0 to 5°C. After slowly dropping 80% acetic acid (10 g) into this mixture in the range of 0 to 5°C and then stirring at the same temperature for 2 hours, a diazo component solution was obtained.

[0569] [Chemical formula 74]

[0570]

[0571] 9-C. Synthesis of the blue dye compound (B-1) by coupling reaction

[0572] (Step 5)

[0573] In the range of 0 to 10 °C, the above diazo component solution (D2) was added dropwise to the above coupling agent component solution (C9) over 2 hours, and at the same time, triethylamine (43 g) was appropriately added to the coupling agent component solution (C9) to carry out a coupling reaction. After stirring for 20 minutes in the range of 0 to 10 °C, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less, thereby obtaining the blue dye compound (20.9 g, yield 62.9%) represented by the following formula (B-1). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 665 (M + ))

[0574] [Chemical formula 75]

[0575]

[0576] (Synthesis Example 10)

[0577] [Synthesis of blue dye compound (B-2)]

[0578] The blue dye compound (B-2) was produced according to the following scheme.

[0579] [Chemical formula 76]

[0580]

[0581] 10-A. Synthesis of coupling agent compound C10 and preparation of coupling agent component solution

[0582] (Step 1)

[0583] In Step 1 of Synthesis Example 9, valeryl chloride (25.3 g) was used instead of n-octanoyl chloride, and otherwise, the same operations as in Steps 1 to 3 of Synthesis Example 9 were carried out to obtain N-[3-(N,N-dioctylamino)phenyl]pentanamide represented by the following formula (C10). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C10) was obtained.

[0584] [Chemical formula 77]

[0585]

[0586] 10-B. Synthesis of blue dye compound (B-2) by coupling reaction

[0587] (Step 2)

[0588] As a coupling agent component solution, the compound of formula (C10) obtained in Step 1 was used in place of the compound of formula (C9), and otherwise, the same operations as in Steps 4 and 5 of Synthesis Example 9 were carried out to obtain the blue dye compound represented by the following formula (B-2) (9.47 g, yield 30.4%). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 623 (M + ))

[0589] [Chemical formula 78]

[0590]

[0591] (Synthesis Example 11)

[0592] [Synthesis of Blue Dye Compound (B-3)]

[0593] The blue dye compound (B-3) was produced according to the following scheme.

[0594] [Chemical formula 79]

[0595]

[0596] 11-A. Synthesis of Coupling Agent Compound C11 and Preparation of Coupling Agent Component Solution

[0597] (Step 1)

[0598] In Step 1 of Synthesis Example 9, propionyl chloride (19.4 g) was used in place of n-octanoyl chloride, and otherwise, the same operations as in Steps 1 to 3 of Synthesis Example 9 were carried out to obtain N-[3-(N,N-dioctylamino)phenyl]propanamide represented by the following formula (C11). By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C11) was obtained.

[0599] [Chemical formula 80]

[0600]

[0601] 11-B. Synthesis of Blue Dye Compound (B-3) by Coupling Reaction

[0602] (Step 2)

[0603] As a coupling agent component solution, the compound of formula (C11) obtained in Step 1 was used in place of the compound of formula (C9), and otherwise, the same operations as in Steps 4 and 5 of Synthesis Example 9 were carried out to obtain the blue dye compound represented by the following formula (B-3) (13.4 g, yield 45.0%). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 595 (M + ))

[0604] [Chemical Formula 81]

[0605]

[0606] (Synthesis Example 12)

[0607] [Synthesis of Blue Dye Compound (B-4)]

[0608] The blue dye compound (B-4) is produced according to the following scheme.

[0609] [Chemical Formula 82]

[0610]

[0611] 12-A. Synthesis of Coupling Agent Compound C12 and Preparation of Coupling Agent Component Solution

[0612] (Step 1)

[0613] In Step 3 of Synthesis Example 9, 3'-aminoacetanilide (7.50 g) was used instead of N-(3-aminophenyl)octanamide, and the operation was the same as in Step 3 of Synthesis Example 9 to obtain N-[3-(N,N-dioctylamino)phenyl]acetamide represented by the following formula (C12). By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C12) was obtained.

[0614] [Chemical Formula 83]

[0615]

[0616] 12-B. Synthesis of Blue Dye Compound (B-4) by Coupling Reaction

[0617] (Step 2)

[0618] As the coupling agent component solution, the compound of formula (C12) was used instead of the compound of formula (C9), and the operation was the same as in Steps 4 and 5 of Synthesis Example 9 to obtain the blue dye compound (20.3 g, yield 69.9%) represented by the following formula (B-4). The above blue dye compound was confirmed by LCMS analysis (m / z 581 (M + )) to confirm its structure.

[0619] [Chemical Formula 84]

[0620]

[0621] (Synthesis Example 13)

[0622] [Synthesis of Blue Dye Compound (B-5)]

[0623] The blue dye compound (B-5) is manufactured according to the following scheme.

[0624] [Chemical Formula 85]

[0625]

[0626] 13-A. Synthesis of Coupling Agent Compound C13 and Preparation of Coupling Agent Component Solution

[0627] (Step 1)

[0628] In Step 3 of Synthesis Example 9, 1-bromododecane (49.8 g) was used instead of 1-bromooctane, and 3'-aminoacetanilide (7.50 g) was used instead of N-(3-aminophenyl)octanamide. Otherwise, the same operations as in Step 3 of Synthesis Example 9 were carried out to obtain N-[3-(N,N-didodecylamino)phenyl]acetamide represented by the following formula (C13). By adding methanol (30 g) to this reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C13) was obtained.

[0629] [Chemical Formula 86]

[0630]

[0631] 13-B. Synthesis of Blue Dye Compound (B-5) by Coupling Reaction

[0632] (Step 2)

[0633] As the coupling agent component solution, the compound of formula (C13) obtained in Step 1 was used instead of the compound of formula (C9). Otherwise, the same operations as in Steps 4 and 5 of Synthesis Example 9 were carried out to obtain the blue dye compound represented by the following formula (B-5) (9.81 g, yield 28.3%). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 693 (M + ))).

[0634] [Chemical Formula 87]

[0635]

[0636] (Synthesis Example 14)

[0637] [Synthesis of Blue Dye Compound (B-6)]

[0638] The blue dye compound (B-6) is manufactured according to the following scheme.

[0639] [Chemical Formula 88]

[0640]

[0641] 14-A. Synthesis of Coupling Agent Compound C14 and Preparation of Coupling Agent Component Solution

[0642] (Step 1)

[0643] In Step 1 of Synthesis Example 9, propionyl chloride (19.4 g) was used instead of n-octanoyl chloride, and 1-bromododecane (49.8 g) was used instead of 1-bromooctane in Step 3 of Synthesis Example 9. Otherwise, the same operations as in Steps 1 to 3 of Synthesis Example 9 were carried out to obtain N-[3-(N,N-didodecylamino)phenyl]propanamide represented by the following formula (C14). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C14) was obtained.

[0644] [Chemical Formula 89]

[0645]

[0646] 14-B. Synthesis of Blue Dye Compound (B-6) by Coupling Reaction

[0647] (Step 2)

[0648] As the coupling agent component solution, the compound of formula (C14) was used instead of the compound of formula (C9). Otherwise, the same operations as in Steps 4 and 5 of Synthesis Example 9 were carried out to obtain the blue dye compound represented by the following formula (B-6) (5.73 g, yield 16.2%). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 707 (M + ))

[0649] [Chemical Formula 90]

[0650]

[0651] (Synthesis Example 15)

[0652] [Synthesis of Blue Dye Compound (B-7)]

[0653] The blue dye compound (B-7) was manufactured according to the following scheme.

[0654] [Chemical Formula 91]

[0655]

[0656] 15-A. Synthesis of Coupling Agent Compound C15 and Preparation of Coupling Agent Component Solution

[0657] (Step 1)

[0658] In Step 3 of Synthesis Example 9, 3'-aminoacetanilide (7.50 g) was used instead of N-(3-aminophenyl)octanamide, and 1-bromo-2-ethylhexane (38.6 g) was used instead of 1-bromooctane. Otherwise, the operation was the same as in Step 3 of Synthesis Example 9 to obtain N-[3-[N,N-bis(2-ethylhexyl)amino]phenyl]propanamide represented by the following formula (C15). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C15) was obtained.

[0659] [Chemical formula 92]

[0660]

[0661] 15-B. Synthesis of Blue Dye Compound (B-7) Using a Coupling Reaction

[0662] (Step 2)

[0663] As the coupling agent component solution, the compound of formula (C15) was used instead of the compound of formula (C9). Otherwise, the operation was the same as in Steps 4 and 5 of Synthesis Example 9 to obtain the blue dye compound (4.72 g, yield 16.2%) represented by the following formula (B-7). The structure of the above blue dye compound was confirmed by LCMS analysis (m / z 581 (M + ))

[0664] [Chemical formula 93]

[0665]

[0666] (Synthesis Example 16)

[0667] [Synthesis of Blue Dye Compound (B-8)]

[0668] The blue dye compound (B-8) was produced according to the following scheme.

[0669] [Chemical formula 94]

[0670]

[0671] 16-A. Synthesis of Coupling Agent Compound C16 and Preparation of Coupling Agent Component Solution

[0672] (Step 1)

[0673] In Step 3 of Synthesis Example 9, 1-bromoethane (27.3 g) was used in place of 1-bromooctane, and otherwise, the same operations as in Steps 1 to 3 of Synthesis Example 9 were carried out to obtain N-[3-(N,N-diethylamino)phenyl]octanamide represented by the following formula (C16). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C16) was obtained.

[0674] [Chemical formula 95]

[0675]

[0676] 16-B. Synthesis of blue dye compound (B-8) using a coupling reaction

[0677] (Step 2)

[0678] As the coupling agent component solution, the compound of formula (C16) obtained in Step 1 was used in place of the compound of formula (C9), and otherwise, the same operations as in Steps 4 and 5 of Synthesis Example 9 were carried out to obtain the blue dye compound represented by the following formula (B-8) (23.2 g, yield 93.4%). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 497 (M + ))

[0679] [Chemical formula 96]

[0680]

[0681] (Synthesis Example 17)

[0682] [Synthesis of red dye compound (C-1)]

[0683] The red dye compound (C-1) was produced according to the following scheme.

[0684] [Chemical formula 97]

[0685]

[0686] 17-A. Preparation of diazo component solution

[0687] (Step 1)

[0688] To a mixture of concentrated sulfuric acid (16 g) and 43% nitrosylsulfuric acid (15.6 g), 2-chloro-4-nitroaniline (8.65 g) represented by the following formula (D3) was added in the range of 30 to 35 °C, and the mixture was stirred at the same temperature for 2 hours to obtain a diazo component solution.

[0689] [Chemical formula 98]

[0690]

[0691] 17-B. Synthesis of Red Dye Compound (C-1) Using Coupling Reaction

[0692] (Step 2)

[0693] The preparation of the coupling agent component solution containing the compound of formula (C9) was carried out in the same manner as in Steps 1 to 3 of Synthesis Example 9. In the range of 0 to 10 °C, the above diazo component solution obtained in Step 1 was added dropwise to the above coupling agent component solution over 2 hours, and at the same time, triethylamine (28 g) was appropriately added to the coupling agent component solution to carry out the coupling reaction. After stirring for 20 minutes in the range of 0 to 10 °C, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less, thereby obtaining the red dye compound represented by the following formula (C-1) (24.3 g, yield 75.7%). The above red dye compound was confirmed for its structure by LCMS analysis (m / z 642 (M + ))

[0694] [Chemical Formula 99]

[0695]

[0696] (Synthesis Example 18)

[0697] [Synthesis of Red Dye Compound (C-2)]

[0698] The red dye compound (C-2) was produced according to the following scheme.

[0699] [Chemical Formula 100]

[0700]

[0701] As the coupling agent component solution, the compound of formula (C10) was used instead of the compound of formula (C9), and otherwise, the same operations as in Steps 1 and 2 of Synthesis Example 17 were carried out to obtain the red dye compound represented by the following formula (C-2) (10.4 g, yield 34.7%). The above red dye compound was confirmed for its structure by LCMS analysis (m / z 600 (M + ))

[0702] [Chemical Formula 101]

[0703]

[0704] (Synthesis Example 19)

[0705] [Synthesis of Red Dye Compound (C-3)]

[0706] The red dye compound (C-3) is produced according to the following scheme.

[0707] [Chemical formula 102]

[0708]

[0709] As the coupling agent component solution, the compound of formula (C11) is used instead of the compound of formula (C9), and otherwise, the same operations as in Steps 1 and 2 of Synthesis Example 17 are carried out to obtain the red dye compound represented by the following formula (C-3) (12.9 g, yield 45.1%). The above red dye compound is confirmed for its structure by LCMS analysis (m / z 572 (M + ))

[0710] [Chemical formula 103]

[0711]

[0712] (Synthesis Example 20)

[0713] [Synthesis of red dye compound (C-4)]

[0714] The red dye compound (C-4) is produced according to the following scheme.

[0715] [Chemical formula 104]

[0716]

[0717] As the coupling agent component solution, the compound of formula (C12) is used instead of the compound of formula (C9), and otherwise, the same operations as in Steps 1 and 2 of Synthesis Example 17 are carried out to obtain the red dye compound represented by the following formula (C-4) (23.4 g, yield 83.9%). The above red dye compound is confirmed for its structure by LCMS analysis (m / z 558 (M + ))

[0718] [Chemical formula 105]

[0719]

[0720] (Synthesis Example 21)

[0721] [Synthesis of red dye compound (C-5)]

[0722] The red dye compound (C-5) is produced according to the following scheme.

[0723] [Chemical formula 106]

[0724]

[0725] As a coupling agent component solution, the compound of formula (C13) was used in place of the compound of formula (C9), and otherwise, the same operations as in Steps 1 and 2 of Synthesis Example 17 were carried out to obtain the red dye compound represented by the following formula (C-5) (25.3 g, yield 75.5%). The above red dye compound was confirmed for its structure by LCMS analysis (m / z 670 (M + ))

[0726] [Chemical formula 107]

[0727]

[0728] (Synthesis Example 22)

[0729] [Synthesis of Red Dye Compound (C-6)]

[0730] The red dye compound (C-6) was produced according to the following scheme.

[0731] [Chemical formula 108]

[0732]

[0733] 22-A. Synthesis of Coupling Agent Compound C17 and Preparation of Coupling Agent Component Solution

[0734] (Step 1)

[0735] In Step 3 of Synthesis Example 9, 3'-aminoacetanilide (7.50 g) was used in place of N-(3-aminophenyl)octanamide, and 1-bromobutane (27.4 g) was used in place of 1-bromooctane, and otherwise, the same operations as in Step 3 of Synthesis Example 9 were carried out to obtain N-[3-(N,N-dibutylamino)phenyl]acetamide represented by the following formula (C17). By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C17) was obtained.

[0736] [Chemical formula 109]

[0737]

[0738] 22-B. Synthesis of Red Dye Compound (C-6) by Coupling Reaction

[0739] (Step 2)

[0740] As a coupling agent component solution, a compound of formula (C17) was used in place of the compound of formula (C9), and otherwise, the same operations as in Steps 1 and 2 of Synthesis Example 17 were carried out to obtain a red dye compound represented by the following formula (C-6) (19.6 g, yield 87.9%). The above red dye compound was confirmed for its structure by LCMS analysis (m / z 446 (M + ))

[0741] [Chemical Formula 110]

[0742]

[0743] (Synthesis Example 23)

[0744] [Synthesis of Red Dye Compound (C-7)]

[0745] The red dye compound (C-7) was produced according to the following scheme.

[0746] [Chemical Formula 111]

[0747]

[0748] As a coupling agent component solution, a compound of formula (C16) was used in place of the compound of formula (C9), and otherwise, the same operations as in Steps 1 and 2 of Synthesis Example 17 were carried out to obtain a red dye compound represented by the following formula (C-7) (16.6 g, yield 70.0%). The above red dye compound was confirmed for its structure by LCMS analysis (m / z 474 (M + ))

[0749] [Chemical Formula 112]

[0750]

[0751] (Synthesis Example 24)

[0752] [Synthesis of Orange Dye Compound (D-1)]

[0753] The orange dye compound (D-1) was produced according to the following scheme.

[0754] [Chemical Formula 113]

[0755]

[0756] 24-A. Synthesis of Coupling Agent Compound C18 and Preparation of Coupling Agent Component Solution

[0757] (Step 1)

[0758] Aniline (4.66 g) was used in place of N-(3-amino-4-methoxyphenyl)octanamide, and the same procedure as in Step 4 of Synthesis Example 1 was carried out to obtain N,N-dioctylaniline represented by the following formula (C18). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C18) was obtained.

[0759] [Chemical formula 114]

[0760]

[0761] 24-B. Preparation of diazo component solution

[0762] (Step 2)

[0763] 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 in the range of 25 to 30 °C, and the mixture was stirred at the same temperature for 2 hours to obtain a diazo component solution.

[0764] [Chemical formula 115]

[0765]

[0766] 24-C. Synthesis of orange dye compound (D-1) by coupling reaction

[0767] (Step 3)

[0768] In the range of 0 to 10 °C, the above diazo component solution obtained in Step 2 was added dropwise to the above coupling agent component solution containing the compound of formula (C18) obtained in Step 1 over 2 hours, and triethylamine (20 g) was appropriately added to the coupling agent component solution to carry out a coupling reaction. After stirring at 0 to 10 °C for 20 minutes, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less to obtain an orange dye compound (23.1 g, yield 86.4%) represented by the following formula (D-1). The above orange dye compound was confirmed by LCMS analysis (m / z 535 (M + )) to confirm its structure.

[0769] [Chemical formula 116]

[0770]

[0771] (Synthesis Example 25)

[0772] [Synthesis of orange dye compound (D-2)]

[0773] The orange dye compound (D-2) is produced according to the following scheme.

[0774] [Chemical formula 117]

[0775]

[0776] 25-A. Synthesis of the coupling agent compound C19 and preparation of the coupling agent component solution

[0777] (Step 1)

[0778] Using aniline (4.66 g) instead of N-(3-amino-4-methoxyphenyl) octanamide and 1-bromododecane (49.8 g) instead of 1-bromooctane, and otherwise operating in the same manner as in Step 4 of Synthesis Example 1, N,N-didodecylaniline represented by the following formula (C19) was obtained. By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C19) was obtained.

[0779] [Chemical formula 118]

[0780]

[0781] 25-B. Synthesis of the orange dye compound (D-2) by a coupling reaction

[0782] (Step 2)

[0783] Using the compound of formula (C19) instead of the compound of formula (C18) as the coupling agent component solution, and otherwise operating in the same manner as in Steps 2 and 3 of Synthesis Example 24, the orange dye compound represented by the following formula (D-2) (14.1 g, yield 43.6%) was obtained. The above orange dye compound was confirmed for its structure by LCMS analysis (m / z 647 (M + ))

[0784] [Chemical formula 119]

[0785]

[0786] (Synthesis Example 26)

[0787] [Synthesis of orange dye compound (D-3)]

[0788] The orange dye compound (D-3) is produced according to the following scheme.

[0789] [Chemical formula 120]

[0790]

[0791] Synthesis of Coupling Agent Compound C20 and Preparation of Coupling Agent Component Solution

[0792] (Step 1)

[0793] Using aniline (4.66 g) instead of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromobutane (27.4 g) instead of 1-bromooctane, and otherwise operating in the same manner as in Step 4 of Synthesis Example 1, N,N-dibutylaniline represented by the following formula (C20) was obtained. By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C20) was obtained.

[0794] [Chemical Formula 121]

[0795]

[0796] 26-B. Synthesis of Orange Dye Compound (D-3) by Coupling Reaction

[0797] (Step 2)

[0798] As the coupling agent component solution, the compound of formula (C20) was used instead of the compound of formula (C18), and otherwise operating in the same manner as in Steps 2 and 3 of Synthesis Example 24, an orange dye compound represented by the following formula (D-3) (10.2 g, yield 48.2%) was obtained. The above orange dye compound was confirmed for its structure by LCMS analysis (m / z 423 (M + ))

[0799] [Chemical Formula 122]

[0800]

[0801] (Synthesis Example 27)

[0802] [Synthesis of Yellow Dye Compound (G-1)]

[0803] The yellow dye compound (G-1) was manufactured according to the following scheme.

[0804] [Chemical Formula 123]

[0805]

[0806] To a mixture of 2-hexyldecanoic acid (30.8 g) and toluene (30 g), a mixture of thionyl chloride (14.3 g) and toluene (20 g) was added dropwise. After slowly adding dropwise a mixture of pyridine (9.49 g) and toluene (30 g) 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 raising the temperature to 110 °C and stirring for 2 hours, the solvent was removed by distillation under reduced pressure, and precipitation was induced by adding methanol (100 g). The mixture was filtered, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less, to obtain a yellow dye compound represented by the following formula (G-1) (36.7 g, yield 74.7%). The above yellow dye compound was confirmed for its structure by LCMS analysis (m / z 491 (M + ))

[0807] [Chemical formula 124]

[0808]

[0809] (Synthesis Example 28)

[0810] [Synthesis of yellow dye compound (G-2)]

[0811] The yellow dye compound (G-2) was produced according to the following scheme.

[0812] [Chemical formula 125]

[0813]

[0814] To a mixture of 5-amino-anthra[9,1-cd]isothiazol-6-one (25.2 g), toluene (120 g) and pyridine (9.49 g), octanoyl chloride (19.5 g) was added dropwise, then the temperature was raised to 110 °C and stirred for 1 hour. After cooling this mixture to room temperature, precipitation was induced by adding methanol (150 g). The mixture was filtered, washed with methanol, and dried, to obtain a yellow dye compound represented by the following formula (G-2) (31.8 g, yield 83.9%). The above yellow dye compound was confirmed for its structure by LCMS analysis (m / z 379 (M + ))

[0815] [Chemical formula 126]

[0816]

[0817] (Synthesis Example 29)

[0818] [Synthesis of purple dye compound (F-1)]

[0819] The purple dye compound (F-1) is produced according to the following scheme.

[0820] [Chemical formula 127]

[0821]

[0822] The preparation of the coupling agent component solution containing the compound of formula (C18) was carried out in the same manner as in Step 1 of Synthesis Example 24, and the preparation of the diazo component solution derived from the compound of formula (D2) was carried out in the same manner as in Step 4 of Synthesis Example 9. In the range of 0 to 10 °C, the above diazo component solution was added dropwise to the above coupling agent component solution over 2 hours, and at the same time, triethylamine (35 g) was appropriately added to the coupling agent component solution to carry out the coupling reaction. After stirring for 20 minutes in the range of 0 to 10 °C, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less, thereby obtaining the purple dye compound shown by the following formula (F-1) (13.0 g, yield 49.6%). The above purple dye compound was confirmed by LCMS analysis (m / z 524 (M + )) to confirm its structure.

[0823] [Chemical formula 128]

[0824]

[0825] (Synthesis Example 30)

[0826] [Synthesis of orange dye compound (D-4)]

[0827] The orange dye compound (D-4) is produced according to the following scheme.

[0828] [Chemical formula 129]

[0829]

[0830] 30-A. Preparation of diazo component solution

[0831] (Step 1)

[0832] In a mixture of concentrated sulfuric acid (17 g) and 43% nitrosylsulfuric acid (14.7 g), 4-nitroaniline (6.91 g) shown by the following formula (D5) was added in the range of 30 to 35 °C and stirred at the same temperature for 2 hours to obtain a diazo component solution.

[0833] [Chemical formula 130]

[0834]

[0835] Synthesis of Orange Dye Compound (D-4) Using Coupling Reaction

[0836] (Step 2)

[0837] The preparation of the coupling agent component solution of the compound containing formula (C18) was carried out in the same manner as in Step 1 of Synthesis Example 24. In the range of 0 to 10 °C, the above diazo component solution obtained in Step 1 was added dropwise to the above coupling agent component solution over 1 hour, and at the same time, triethylamine (20 g) was appropriately added to the coupling agent component solution to carry out the coupling reaction. After stirring for 20 minutes in the range of 0 to 10 °C, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less, thereby obtaining the orange dye compound (12.5 g, yield 53.5%) represented by the following formula (D-4). The above orange dye compound was confirmed for its structure by LCMS analysis (m / z 467 (M + ))

[0838] [Chemical Formula 131]

[0839]

[0840] (Synthesis Example 31)

[0841] [Synthesis of Orange Dye Compound (D-5)]

[0842] The orange dye compound (D-5) was manufactured according to the following scheme.

[0843] [Chemical Formula 132]

[0844]

[0845] 31-A. Preparation of Diazo Component Solution

[0846] (Step 1)

[0847] In 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 in the range of 25 to 30 °C, and the mixture was stirred at the same temperature for 2 hours to obtain a diazo component solution.

[0848] [Chemical Formula 133]

[0849]

[0850] 31-B. Synthesis of Orange Dye Compound (D-5) Using Coupling Reaction

[0851] (Step 2)

[0852] The preparation of the coupling agent component solution of the compound of inclusion formula (C18) was carried out in the same manner as in Step 1 of Synthesis Example 24. In the range of 0 to 10 °C, the above diazo component solution obtained in Step 1 was added dropwise to the above coupling agent component solution over 1 hour, and at the same time, triethylamine (25 g) was appropriately added to the coupling agent component solution to carry out the coupling reaction. After stirring for 20 minutes in the range of 0 to 10 °C, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0% by mass or less, thereby obtaining the orange dye compound shown by the following formula (D-5) (27.6 g, yield 88.6%). The above orange dye compound was analyzed by LCMS (m / z 623 (M + )) and its structure was confirmed to be the following formula (D-5).

[0853] [Chemical formula 134]

[0854]

[0855] (Synthesis Example 32)

[0856] [Synthesis of Orange Dye Compound (D-6)]

[0857] The orange dye compound (D-6) was manufactured according to the following scheme.

[0858] [Chemical formula 135]

[0859]

[0860] As the coupling agent component solution, the compound of formula (C20) was used instead of the compound of formula (C18). Otherwise, the same operations as in Steps 1 and 2 of Synthesis Example 31 were carried out to obtain the orange dye compound shown by the following formula (D-6) (22.8 g, yield 89.2%). The above orange dye compound was analyzed by LCMS (m / z 511 (M + )) to confirm its structure.

[0861] [Chemical formula 136]

[0862]

[0863] (Synthesis Example 33)

[0864] [Synthesis of Orange Dye Compound (E-1)]

[0865] The orange dye compound (E-1) was manufactured according to the following scheme.

[0866] [Chemical formula 137]

[0867]

[0868] 33-A. Synthesis of Coupling Agent Compound C21 and Preparation of Coupling Agent Component Solution

[0869] (Step 1)

[0870] 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 stirred at the same temperature for 3 hours to obtain N-octyl-2-phenylindole represented by the following formula (C21). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C21) was obtained.

[0871] [Chemical Formula 138]

[0872]

[0873] 33-B. Synthesis of Orange Dye Compound (E-1) by Coupling Reaction

[0874] (Step 2)

[0875] The preparation of the diazo component solution derived from the compound of formula (D4) was carried out in the same manner as in Synthesis Example 24. In the range of 0 to 10 °C, the above diazo component solution was added dropwise to the above coupling agent component solution obtained in Step 1 over 1 hour, and triethylamine (20 g) was appropriately added to the coupling agent component solution to carry out a coupling reaction. After stirring for 20 minutes in the range of 0 to 10 °C, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less to obtain the orange dye compound represented by the following formula (E-1) (11.3 g, yield 43.2%). The above orange dye compound was confirmed for its structure by LCMS analysis (m / z 523 (M + ))

[0876] [Chemical Formula 139]

[0877]

[0878] (Synthesis Example 34)

[0879] [Synthesis of Orange Dye Compound (E-2)]

[0880] The orange dye compound (E-2) was produced according to the following scheme.

[0881] [Chemical Formula 140]

[0882]

[0883] 34-A. Synthesis of Coupling Agent Compound C22 and Preparation of Coupling Agent Component Solution

[0884] (Step 1)

[0885] Using 1-bromobutane (7.53 g) instead of 1-bromooctane, and otherwise operating in the same manner as in Step 1 of Synthesis Example 33, N-butyl-2-phenylindole represented by the following formula (C22) was obtained. By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C22) was obtained.

[0886] [Chemical Formula 141]

[0887]

[0888] 34-B. Synthesis of Orange Dye Compound (E-2) by Coupling Reaction

[0889] (Step 2)

[0890] Using the compound of formula (C22) as the coupling agent component solution instead of the compound of formula (C21), and otherwise operating in the same manner as in Steps 1 and 2 of Synthesis Example 33, an orange dye compound represented by the following formula (E-2) (14.5 g, yield 62.1%) was obtained. The structure of the above orange dye compound was confirmed by LCMS analysis (m / z 467 (M + ))

[0891] [Chemical Formula 142]

[0892]

[0893] (Synthesis Example 35)

[0894] [Synthesis of Red Dye Compound (D-7)]

[0895] The red dye compound (D-7) was manufactured according to the following scheme.

[0896] [Chemical Formula 143]

[0897]

[0898] 35-A. Preparation of Diazo Component Solution

[0899] (Step 1)

[0900] 2-Cyano-4-nitroaniline (8.15 g) represented by the following formula (D7) was added to a mixture of concentrated sulfuric acid (7.5 g), acetic acid (15 g), and 43% nitrosylsulfuric acid (14.9 g) 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.

[0901] [Chemical formula 144]

[0902]

[0903] 35-B. Synthesis of Red Dye Compound (D-7) Using Coupling Reaction

[0904] (Step 2)

[0905] The preparation of the coupling agent component solution containing the compound of formula (C18) was carried out in the same manner as in Synthesis Example 24. Within the range of 0 to 10 °C, the above diazo component solution obtained in Step 1 was added dropwise to the above coupling agent component solution over 1 hour, and triethylamine (30 g) was appropriately added to the coupling agent component solution to carry out the coupling reaction. After stirring for 20 minutes within the range of 0 to 10 °C, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less to obtain a red dye compound (16.9 g, yield 68.9%) represented by the following formula (D-7). The above red dye compound was confirmed for its structure by LCMS analysis (m / z 492 (M + )).

[0906] [Chemical formula 145]

[0907]

[0908] (Synthesis Example 36)

[0909] [Synthesis of Purple Dye Compound (C-8)]

[0910] The purple dye compound (C-8) was manufactured according to the following scheme.

[0911] [Chemical formula 146]

[0912]

[0913] The preparation of the coupling agent component solution of the compound of inclusion formula (C16) was carried out in the same manner as in Step 1 of Synthesis Example 16, and the preparation of the diazo component solution derived from the compound of formula (D1) was carried out in the same manner as in Step 5 of Synthesis Example 1. In the range of 0 to 10 °C, the above diazo component solution was added dropwise to the above coupling agent component solution over 2 hours, and at the same time, triethylamine (32 g) was appropriately added to the coupling agent component solution to carry out a coupling reaction. After stirring for 20 minutes in the range of 0 to 10 °C, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less, thereby obtaining the purple dye compound shown by the following formula (C-8) (6.14 g, yield 21.8%). The molecular weight of the above purple dye compound was analyzed by LCMS (m / z 563 (M + )) to confirm that its structure was the following formula (C-8).

[0914] [Chemical formula 147]

[0915]

[0916] (Synthesis Example 37)

[0917] [Synthesis of purple dye compound (C-9)]

[0918] The purple dye compound (C-9) was manufactured according to the following scheme.

[0919] [Chemical formula 148]

[0920]

[0921] As the coupling agent component solution, the compound of formula (C9) was used instead of the compound of formula (C16), and otherwise, the same operations as in Synthesis Example 36 were carried out to obtain the purple dye compound shown by the following formula (C-9) (12.1 g). The structure of the above purple dye compound was confirmed by LCMS analysis (m / z 731 (M + ).

[0922] [Chemical formula 149]

[0923]

[0924] (Synthesis Example 38)

[0925] [Synthesis of purple dye compound (C-10)]

[0926] The purple dye compound (C-10) was manufactured according to the following scheme.

[0927] [Chemical formula 150]

[0928]

[0929] A mixture of sodium bromide (5.92 g), triethylamine (0.50 g), and DMF (80 g) was stirred for 15 minutes in the range of 35 to 40 °C, copper(I) cyanide (5.0 g) was added, and the mixture was stirred for 15 minutes at the same temperature. A purple dye compound (C-9) (34.3 g) was added to the mixture, the temperature was raised to 110 °C, and the mixture was stirred for 1 hour. After cooling to 80 °C, a mixture of water (190 g) and sodium hypochlorite (18 g) was added, and the mixture was stirred at 70 to 80 °C for 1 hour and then cooled to room temperature. The product was filtered out from the reaction mixture, washed with water, and dried at 60 °C until the water content became 1.0 mass% or less, thereby obtaining the purple dye compound represented by the following formula (C-10) (20.4 g, yield 64.2%). The above purple dye compound was confirmed for its structure by LCMS analysis (m / z 678 (M + ))

[0930] [Chemical formula 151]

[0931]

[0932] (Synthesis Example 39)

[0933] [Synthesis of Purple Dye Compound (C-11)]

[0934] The purple dye compound (C-11) was produced according to the following scheme.

[0935] [Chemical formula 152]

[0936]

[0937] 39-A. Preparation of Diazo Component Solution

[0938] (Step 1)

[0939] 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) in the range of 20 to 25 °C. By adding 43% nitrosylsulfuric acid (15.6 g) to the mixture in the range of 20 to 25 °C and stirring the mixture at the same temperature for 2 hours, a diazo component solution was obtained.

[0940] [Chemical formula 153]

[0941]

[0942] 39-B. Synthesis of Purple Dye Compound (C-11) by Coupling Reaction

[0943] (Step 2)

[0944] The preparation of the coupling agent component solution of the compound of inclusion formula (C9) was carried out in the same manner as in Steps 1 to 3 of Synthesis Example 9. In the range of 0 to 10 °C, the above diazo component solution obtained in Step 1 was added dropwise to the above coupling agent component solution over 2 hours, and at the same time, triethylamine (20 g) was appropriately added to the coupling agent component solution to carry out a coupling reaction. After stirring for 20 minutes in the range of 0 to 10 °C, the product was filtered out from the reaction mixture, washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 mass% or less, thereby obtaining the purple dye compound shown by the following formula (C-11) (16.0 g, yield 45.0%). The above purple dye compound was confirmed for its structure by LCMS analysis (m / z 711 (M + ))

[0945] [Chemical Formula 154]

[0946]

[0947] (Synthesis Example 40)

[0948] [Synthesis of Purple Dye Compound (C-12)]

[0949] The purple dye compound (C-12) was manufactured according to the following scheme.

[0950] [Chemical Formula 155]

[0951]

[0952] 40-A. Synthesis of Coupling Agent Compound C23 and Preparation of Coupling Agent Component Solution

[0953] (Step 1)

[0954] In Step 3 of Synthesis Example 9, 1-bromobutane (27.4 g) was used instead of 1-bromooctane, and otherwise, the same operations as in Steps 1 to 3 of Synthesis Example 9 were carried out to obtain N-[3-(N,N-dibutylamino)phenyl]octanamide shown by the following formula (C23). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C23) was obtained.

[0955] [Chemical Formula 156]

[0956]

[0957] 40-B. Synthesis of Purple Dye Compound (C-12) by Coupling Reaction

[0958] (Step 2)

[0959] As a coupling agent component solution, a compound of formula (C23) was used in place of the compound of formula (C9), and otherwise, the operation was carried out in the same manner as in Step 2 of Synthesis Example 39 to obtain a purple dye compound represented by the following formula (C-12) (5.99 g, yield 20.0%). The above purple dye compound was confirmed for its structure by LCMS analysis (m / z 599 (M + ))

[0960] [Chemical Formula 157]

[0961]

[0962] (Synthesis Example 41)

[0963] [Synthesis of Purple Dye Compound (C-13)]

[0964] The purple dye compound (C-13) was produced according to the following scheme.

[0965] [Chemical Formula 158]

[0966]

[0967] As a coupling agent component solution, a compound of formula (C12) was used in place of the compound of formula (C9), and otherwise, the operation was carried out in the same manner as in Step 2 of Synthesis Example 39 to obtain a purple dye compound represented by the following formula (C-13) (23.5 g, yield 75.0%). The above purple dye compound was confirmed for its structure by LCMS analysis (m / z 627 (M + ))

[0968] [Chemical Formula 159]

[0969]

[0970] (Synthesis Example 42)

[0971] [Synthesis of Purple Dye Compound (C-14)]

[0972] The purple dye compound (C-14) was produced according to the following scheme.

[0973] [Chemical Formula 160]

[0974]

[0975] As a coupling agent component solution, a compound of formula (C16) was used instead of the compound of formula (C9), and otherwise, the same operations as in Step 2 of Synthesis Example 39 were carried out to obtain a purple dye compound represented by the following formula (C-14) (10.8 g, yield 39.8%). The above purple dye compound was confirmed for its structure by LCMS analysis (m / z 543 (M + ))

[0976] [Chemical Formula 161]

[0977]

[0978] (Synthesis Example 43)

[0979] [Synthesis of Purple Dye Compound (C-15)]

[0980] The purple dye compound (C-15) was produced according to the following scheme.

[0981] [Chemical Formula 162]

[0982]

[0983] In Synthesis Example 38, a purple dye compound of formula (C-13) (31.4 g) was used instead of the purple dye compound of formula (C-9), and otherwise, the same operations as in Synthesis Example 38 were carried out to obtain a purple dye compound represented by the following formula (C-15) (26.9 g, yield 93.7%). The above purple dye compound was confirmed for its structure by LCMS analysis (m / z 574 (M + ))

[0984] [Chemical Formula 163]

[0985]

[0986] (Synthesis Example 44)

[0987] [Synthesis of Purple Dye Compound (C-16)]

[0988] The purple dye compound (C-16) was produced according to the following scheme.

[0989] [Chemical Formula 164]

[0990]

[0991] In Synthesis Example 38, the purple dye compound of formula (C-14) (27.2 g) was used instead of the purple dye compound of formula (C-9), and otherwise the same operations as in Synthesis Example 38 were carried out to obtain the purple dye compound shown by the following formula (C-16) (22.0 g, yield 89.8%). The above purple dye compound was confirmed for its structure by LCMS analysis (m / z 490 (M + ))

[0992] [Chemical Formula 165]

[0993]

[0994] (Synthesis Example 45)

[0995] [Synthesis of Yellow Dye Compound (G-3)]

[0996] The yellow dye compound (G-3) was produced according to the following scheme.

[0997] [Chemical Formula 166]

[0998]

[0999] In Synthesis Example 28, 2-ethylhexanoyl chloride (19.5 g) was used instead of n-octanoyl chloride, and otherwise the same operations as in Synthesis Example 28 were carried out to obtain the yellow dye compound shown by the following formula (G-3) (33.1 g, yield 87.3%). The above yellow dye compound was confirmed for its structure by LCMS analysis (m / z 379 (M + ))

[1000] [Chemical Formula 167]

[1001]

[1002] (Synthesis Example 46)

[1003] [Synthesis of Yellow Dye Compound (G-4)]

[1004] The yellow dye compound (G-4) was produced according to the following scheme.

[1005] [Chemical Formula 168]

[1006]

[1007] In Synthesis Example 28, nonanoyl chloride (21.2 g) was used instead of n-octanoyl chloride, and otherwise the same operations as in Synthesis Example 28 were carried out to obtain the yellow dye compound shown by the following formula (G-4) (31.0 g, yield 78.9%). The above yellow dye compound was confirmed for its structure by LCMS analysis (m / z 393 (M +))) to confirm its structure.

[1008] [Chemical Formula 169]

[1009]

[1010] (Synthesis Example 47)

[1011] [Synthesis of Blue Dye Compound (B-9)]

[1012] The blue dye compound (B-9) is produced according to the following scheme.

[1013] [Chemical Formula 170]

[1014]

[1015] As the coupling agent component solution, the compound of formula (C23) is used instead of the compound of formula (C9), and otherwise, the operation is the same as in Step 5 of Synthesis Example 9, to obtain the blue dye compound represented by the following formula (B-9) (9.12 g, yield 33.0%). The above blue dye compound is confirmed by LCMS analysis (m / z 553 (M + )) to confirm its structure.

[1016] [Chemical Formula 171]

[1017]

[1018] (Synthesis Example 48)

[1019] [Synthesis of Blue Dye Compound (B-10)]

[1020] The blue dye compound (B-10) is produced according to the following scheme.

[1021] [Chemical Formula 172]

[1022]

[1023] 48-A. Synthesis of Coupling Agent Compound C24 and Preparation of Coupling Agent Component Solution

[1024] (Step 1)

[1025] In Step 1 of Synthesis Example 9, 2-ethylhexanoyl chloride (34.2 g) is used instead of n-octanoyl chloride, and otherwise, the operation is the same as in Steps 1 to 3 of Synthesis Example 9, to obtain N-[3-(N,N-dioctylamino)phenyl]-2-ethylhexanamide represented by the following formula (C24). By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C24) is obtained.

[1026] [Chemical Formula 173]

[1027]

[1028] 48-B. Synthesis of Blue Dye Compound (B-10) Using Coupling Reaction

[1029] (Step 2)

[1030] As the coupling agent component solution, the compound of formula (C24) was used instead of the compound of formula (C9), and the same operations as in Steps 4 and 5 of Synthesis Example 9 were carried out to obtain the blue dye compound represented by the following formula (B-10) (19.0 g, yield 57.1%). The structure of the above blue dye compound was confirmed by LCMS analysis (m / z 665 (M + ))

[1031] [Chemical Formula 174]

[1032]

[1033] (Synthesis Example 49)

[1034] [Synthesis of Orange Dye Compound (D-8)]

[1035] The orange dye compound (D-8) was produced according to the following scheme.

[1036] [Chemical Formula 175]

[1037]

[1038] As the coupling agent compound, N,N-diethylaniline (7.45 g) was used instead of the compound of formula (C18), and the same operations as in Synthesis Example 24 were carried out to obtain the orange dye compound represented by the following formula (D-8) (15.2 g, yield 82.8%). The structure of the above orange dye compound was confirmed by LCMS analysis (m / z 367 (M + ))

[1039] [Chemical Formula 176]

[1040]

[1041] (Synthesis Example 50)

[1042] [Synthesis of Orange Dye Compound (D-9)]

[1043] The orange dye compound (D-9) was produced according to the following scheme.

[1044] [Chemical Formula 177]

[1045]

[1046] As a coupling agent compound, N,N - diethylaniline (7.45 g) was used in place of the compound of formula (C18), and otherwise, the same operations as in Synthesis Example 31 were carried out to obtain an orange dye compound represented by the following formula (D - 9) (18.2 g, yield 80.0%). The above orange dye compound was confirmed for its structure by LCMS analysis (m / z 455 (M + ))

[1047] [Chemical formula 178]

[1048]

[1049] (Synthesis Example 51)

[1050] [Synthesis of Orange Dye Compound (D - 10)]

[1051] The orange dye compound (D - 10) was manufactured according to the following scheme.

[1052] [Chemical formula 179]

[1053]

[1054] As a coupling agent compound, N,N - diethylaniline (7.45 g) was used in place of the compound of formula (C18), and otherwise, the same operations as in Synthesis Example 30 were carried out to obtain an orange dye compound represented by the following formula (D - 10) (9.35 g, yield 62.5%). The above orange dye compound was confirmed for its structure by LCMS analysis (m / z 299 (M + ))

[1055] [Chemical formula 180]

[1056]

[1057] (Synthesis Example 52)

[1058] [Synthesis of Orange Dye Compound (D - 11)]

[1059] The orange dye compound (D - 11) was manufactured according to the following scheme.

[1060] [Chemical formula 181]

[1061]

[1062] 52 - A. Synthesis of Coupling Agent Compound C25 and Preparation of Coupling Agent Component Solution

[1063] (Step 1)

[1064] 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. After washing the extract with saturated brine, the solvent was removed by distillation under reduced pressure to obtain N-cyanoethylaniline (28.7 g, yield 98.2%) represented by the following formula (C25a) as a crude product.

[1065] [Chemical formula 182]

[1066]

[1067] (Step 2)

[1068] A mixture of the 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 stirred at the same temperature for 3 hours to obtain N-cyanoethyl-N-octylaniline represented by the following formula (C25). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C25) was obtained.

[1069] [Chemical formula 183]

[1070]

[1071] 52-B. Synthesis of Orange Dye Compound (D-11) Using a Coupling Reaction

[1072] (Step 3)

[1073] As the coupling agent component solution, the compound of formula (C25) was used instead of the compound of formula (C18), and the same procedure as in Synthesis Example 30 was carried out to obtain an orange dye compound (10.6 g, yield 52.0%) represented by the following formula (D-11). The structure of the above orange dye compound was confirmed by LCMS analysis (m / z 408 (M + )).

[1074] [Chemical formula 184]

[1075]

[1076] (Synthesis Example 53)

[1077] [Synthesis of Red Dye Compound (C-17)]

[1078] The red dye compound (C-17) was produced according to the following scheme.

[1079] [Chemical Formula 185]

[1080]

[1081] 53-A. Synthesis of Coupling Agent Compound C26 and Preparation of Coupling Agent Component Solution

[1082] (Step 1)

[1083] Using 3'-aminoacetanilide (7.50 g) to replace N-(3-amino-4-methoxyphenyl)octanamide, and using bromoethane (27.3 g) to replace 1-bromooctane, and otherwise operating in the same manner as in Step 4 of Synthesis Example 1, N-[3-(N,N-diethylamino)phenyl]acetamide represented by the following formula (C26) was obtained. By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C26) was obtained.

[1084] [Chemical Formula 186]

[1085]

[1086] 53-B. Synthesis of Red Dye Compound (C-17) by Coupling Reaction

[1087] (Step 2)

[1088] As the coupling agent compound, the compound of formula (C26) was used to replace the compound of formula (C9), and otherwise operating in the same manner as in Synthesis Example 17, a red dye compound represented by the following formula (C-17) (11.8 g, yield 60.5%) was obtained. The above red dye compound was confirmed for its structure by LCMS analysis (m / z 390 (M + ))

[1089] [Chemical Formula 187]

[1090]

[1091] (Synthesis Example 54)

[1092] [Synthesis of Purple Dye Compound (F-2)]

[1093] The purple dye compound (F-2) was manufactured according to the following scheme.

[1094] [Chemical Formula 188]

[1095]

[1096] As a coupling agent compound, N,N-diethylaniline (7.45 g) was used in place of the compound of formula (C18), and otherwise, the same operations as in Synthesis Example 29 were carried out to obtain a purple dye compound (10.6 g, yield 59.6%) represented by the following formula (F-2). The above purple dye compound was confirmed for its structure by LCMS analysis (m / z 356 (M + ))

[1097] [Chemical formula 189]

[1098]

[1099] (Synthesis Example 55)

[1100] [Synthesis of blue dye compound (B-11)]

[1101] The blue dye compound (B-11) was produced according to the following scheme.

[1102] [Chemical formula 190]

[1103]

[1104] As a coupling agent compound, the compound of formula (C26) was used in place of the compound of formula (C9), and otherwise, the same operations as in Steps 4 and 5 of Synthesis Example 9 were carried out to obtain a blue dye compound (11.9 g, yield 57.6%) represented by the following formula (B-11). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 413 (M + ))

[1105] [Chemical formula 191]

[1106]

[1107] (Synthesis Example 56)

[1108] [Synthesis of blue dye compound (A-9)]

[1109] The blue dye compound (A-9) was produced according to the following scheme.

[1110] [Chemical formula 192]

[1111]

[1112] 56-A. Synthesis of coupling agent compound C27 and preparation of coupling agent component solution

[1113] (Step 1)

[1114] A mixture of N-(3-amino-4-methoxyphenyl)octanamide (13.2 g), acetic acid (15 g), copper(I) chloride (0.32 g), and acrylonitrile (5.0 g) obtained in Step 3 of Synthesis Example 1 was heated to 110 °C and stirred for 3 hours. After cooling to room temperature, toluene (50 g) and a 10% aqueous sodium carbonate solution (75 g) were added to extract the organic layer. The extract was washed with saturated brine, and then the solvent was removed by distillation under reduced pressure to obtain N-(3-cyanoethylamino-4-methoxyphenyl)octanamide (9.05 g, yield 57.0%) represented by the following formula (C27a) as a crude product.

[1115] [Chemical Formula 193]

[1116]

[1117] (Step 2)

[1118] A mixture of N-(3-cyanoethylamino-4-methoxyphenyl)octanamide (15.9 g), DMF (15 g), and diethyl sulfate (11.6 g) obtained in the above step was heated to 90 °C and stirred at the same temperature for 2 hours to obtain N-(3-N-ethyl-N-cyanoethylamino-4-methoxyphenyl)octanamide represented by the following formula (C27). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C27) was obtained.

[1119] [Chemical Formula 194]

[1120]

[1121] 56-B. Synthesis of Blue Dye Compound (A-9) by Coupling Reaction

[1122] (Step 3)

[1123] As the coupling agent component solution, the compound of formula (C27) was used instead of the compound of formula (C1), and otherwise, the same operations as in Steps 5 and 6 of Synthesis Example 1 were carried out to obtain the blue dye compound (9.70 g, yield 31.4%) represented by the following formula (A-9). The structure of the above blue dye compound was confirmed by LCMS analysis (m / z 618 (M + ))).

[1124] [Chemical Formula 195]

[1125]

[1126] (Synthesis Example 57)

[1127] [Synthesis of Blue Dye Compound (A-10)]

[1128] The blue dye compound (A-10) is produced according to the following scheme.

[1129] [Chemical Formula 196]

[1130]

[1131] 57-A. Synthesis of Coupling Agent Compound C28 and Preparation of Coupling Agent Component Solution

[1132] (Step 1)

[1133] By heating a mixture of 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) to 120°C and stirring for 8 hours, N-(3-N-octyl-N-cyanoethylamino-4-methoxyphenyl)octanamide represented by the following formula (C28) is obtained. By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C28) is obtained.

[1134] [Chemical Formula 197]

[1135]

[1136] 57-B. Synthesis of Blue Dye Compound (A-10) by Coupling Reaction

[1137] (Step 2)

[1138] As the coupling agent component solution, the compound of formula (C28) is used instead of the compound of formula (C1), and otherwise, the same operations as in Steps 5 and 6 of Synthesis Example 1 are carried out to obtain the blue dye compound represented by the following formula (A-10) (5.52 g, yield 15.7%). The above blue dye compound is confirmed for its structure by LCMS analysis (m / z 702 (M + ))

[1139] [Chemical Formula 198]

[1140]

[1141] (Synthesis Example 58)

[1142] [Synthesis of Blue Dye Compound (A-11)]

[1143] The blue dye compound (A-11) is produced according to the following scheme.

[1144] [Chemical Formula 199]

[1145]

[1146] 58-A. Synthesis of Coupling Agent Compound C29 and Preparation of Coupling Agent Component Solution

[1147] (Step 1)

[1148] By heating a mixture of 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) to 110 °C and stirring for 8 hours, N-[3-N,N-(2-dimethoxyethyl)amino-4-methoxyphenyl]octanamide represented by the following formula (C29) was obtained. By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C29) was obtained.

[1149] [Chemical Formula 200]

[1150]

[1151] (Step 2)

[1152] As the coupling agent component solution, the compound of formula (C29) was used instead of the compound of formula (C1), and otherwise, the same operations as in Steps 5 and 6 of Synthesis Example 1 were carried out to obtain a blue dye compound (6.58 g, yield 20.2%) represented by the following formula (A-11). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 653 (M + ))).

[1153] [Chemical Formula 201]

[1154]

[1155] (Synthesis Example 59)

[1156] [Synthesis of Blue Dye Compound (A-12)]

[1157] The blue dye compound (A-12) was manufactured according to the following scheme.

[1158] [Chemical Formula 202]

[1159]

[1160] 59-A. Synthesis of Coupling Agent Compound C30 and Preparation of Coupling Agent Component Solution

[1161] (Step 1)

[1162] N-(3-amino-4-methoxyphenyl)acetamide (purchased as a commercial product) (9.0 g) was used in place of N-(3-amino-4-methoxyphenyl)octanamide, and 1-bromobutane (27.4 g) was used in place of 1-bromooctane. Otherwise, the same operations as in Step 4 of Synthesis Example 1 were carried out to obtain N-[3-(N,N-dihexylamino)-4-methoxyphenyl]acetamide represented by the following formula (C30). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a solution containing the coupling agent component of formula (C30) was obtained.

[1163] [Chemical formula 203]

[1164]

[1165] 59-B. Synthesis of blue dye compound (A-12) using a coupling reaction

[1166] (Step 2)

[1167] As the coupling agent component solution, the compound of formula (C30) was used in place of the compound of formula (C1). Otherwise, the same operations as in Steps 5 and 6 of Synthesis Example 1 were carried out to obtain the blue dye compound (14.1 g, yield 49.9%) represented by the following formula (A-12). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 565 (M + ))

[1168] [Chemical formula 204]

[1169]

[1170] (Synthesis Example 60)

[1171] [Synthesis of blue dye compound (A-13)]

[1172] The blue dye compound (A-13) was manufactured according to the following scheme.

[1173] [Chemical formula 205]

[1174]

[1175] 60-A. Synthesis of coupling agent compound C31 and preparation of coupling agent component solution

[1176] (Step 1)

[1177] N-(3-Amino-4-methoxyphenyl)acetamide (purchased as a commercial product) (9.0 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide, and 1-bromohexane (33.0 g) was used instead of 1-bromooctane. Otherwise, the operation was the same as in Step 4 of Synthesis Example 1 to obtain N-[3-(N,N-dihexylamino)-4-methoxyphenyl]acetamide represented by the following formula (C31). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C31) was obtained.

[1178] [Chemical formula 206]

[1179]

[1180] 60-B. Synthesis of Blue Dye Compound (A-13) by Coupling Reaction

[1181] (Step 2)

[1182] As the coupling agent component solution, the compound of formula (C31) was used instead of the compound of formula (C1). Otherwise, the operation was the same as in Steps 5 and 6 of Synthesis Example 1 to obtain the blue dye compound represented by the following formula (A-13) (10.7 g, yield 34.5%). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 621 (M + )).

[1183] [Chemical formula 207]

[1184]

[1185] (Synthesis Example 61)

[1186] [Synthesis of Blue Dye Compound (A-14)]

[1187] The blue dye compound (A-14) was manufactured according to the following scheme.

[1188] [Chemical formula 208]

[1189]

[1190] 61-A. Synthesis of Coupling Agent Compound C32 and Preparation of Coupling Agent Component Solution

[1191] (Step 1)

[1192] In Step 1 of Synthesis Example 1, valeryl chloride (25.3 g) was used in place of n - octanoyl chloride, and in Step 4, 1 - bromoethane (27.3 g) was used in place of 1 - bromooctane. Otherwise, the operations were the same as in Steps 1 to 4 of Synthesis Example 1, and N - [3 - (N,N - diethylamino) - 4 - methoxyphenyl] pentanamide represented by the following formula (C32) was obtained. By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C32) was obtained.

[1193] [Chemical formula 209]

[1194]

[1195] 61 - B. Synthesis of blue dye compound (A - 14) using a coupling reaction

[1196] (Step 2)

[1197] As the coupling agent component solution, the compound of formula (C32) was used in place of the compound of formula (C1). Otherwise, the operations were the same as in Steps 5 and 6 of Synthesis Example 1, and the blue dye compound represented by the following formula (A - 14) (24.1 g, yield 87.5%) was obtained. The structure of the above blue dye compound was confirmed by LCMS analysis (m / z 551 (M + )).

[1198] [Chemical formula 210]

[1199]

[1200] (Synthesis Example 62)

[1201] [Synthesis of blue dye compound (A - 15)]

[1202] The blue dye compound (A - 15) was manufactured according to the following scheme.

[1203] [Chemical formula 211]

[1204]

[1205] 62 - A. Synthesis of coupling agent compound C33 and preparation of coupling agent component solution

[1206] (Step 1)

[1207] In Step 1 of Synthesis Example 1, lauroyl chloride (45.9 g) was used instead of octanoyl chloride, and in Step 4, 1-bromoethane (27.3 g) was used instead of 1-bromooctane. Otherwise, the operations were the same as those in Steps 1 to 4 of Synthesis Example 1 to obtain N-[3-(N,N-diethylamino)-4-methoxyphenyl]dodecanamide represented by the following formula (C33). By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C33) was obtained.

[1208] [Chemical formula 212]

[1209]

[1210] 62-B. Synthesis of Blue Dye Compound (A-15) by Coupling Reaction

[1211] (Step 2)

[1212] As the coupling agent component solution, formula (C33) was used instead of formula (C1). Otherwise, the operations were the same as those in Steps 5 and 6 of Synthesis Example 1 to obtain the blue dye compound (26.8 g, yield 82.6%) represented by the following formula (A-15). The above blue dye compound was confirmed for its structure by LCMS analysis (m / z 649 (M + ))).

[1213] [Chemical formula 213]

[1214]

[1215] (Synthesis Example 63)

[1216] [Synthesis of Red Dye Compound (C-18)]

[1217] The red dye compound (C-18) was manufactured according to the following scheme.

[1218] [Chemical formula 214]

[1219]

[1220] 63-A. Synthesis of Coupling Agent Compound C34 and Preparation of Coupling Agent Component Solution

[1221] (Step 1)

[1222] In Step 3 of Synthesis Example 9, 1-bromohexane (33.0 g) was used instead of 1-bromooctane, and 3'-aminoacetanilide (7.50 g) was used instead of N-(3-aminophenyl)octanamide. Otherwise, the operation was the same as in Step 3 of Synthesis Example 9 to obtain N-[3-(N,N-dihexylamino)phenyl]acetamide represented by the following formula (C34). By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C34) was obtained.

[1223] [Chemical formula 215]

[1224]

[1225] 63-B. Synthesis of Red Dye Compound (C-18) by Coupling Reaction

[1226] (Step 2)

[1227] As the coupling agent component solution, the compound of formula (C34) was used instead of the compound of formula (C9). Otherwise, the operation was the same as in Synthesis Example 17 to obtain the red dye compound (20.1 g, yield 80.1%) represented by the following formula (C-18). The above red dye compound was confirmed for its structure by LCMS analysis (m / z 502 (M + )).

[1228] [Chemical formula 216]

[1229]

[1230] (Synthesis Example 64)

[1231] [Synthesis of Orange Dye Compound (D-12)]

[1232] The orange dye compound (D-12) was manufactured according to the following scheme.

[1233] [Chemical formula 217]

[1234]

[1235] 64-A. Synthesis of Coupling Agent Compound C35 and Preparation of Coupling Agent Component Solution

[1236] (Step 1)

[1237] Aniline (4.66 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide, and 1-bromohexane (33.0 g) was used instead of 1-bromooctane. Otherwise, the same operation as in Step 4 of Synthesis Example 1 was carried out to obtain N,N-dihexylaniline represented by the following formula (C35). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C35) was obtained.

[1238] [Chemical formula 218]

[1239]

[1240] 64-B. Synthesis of Orange Dye Compound (D-12) by Coupling Reaction

[1241] (Step 2)

[1242] As the coupling agent component solution, the compound of formula (C35) was used instead of the compound of formula (C18). Otherwise, the same operation as in Synthesis Example 24 was carried out to obtain the orange dye compound represented by the following formula (D-12) (13.5 g, yield 56.4%). The above orange dye compound was confirmed by LCMS analysis (m / z 479 (M + )) to confirm its structure.

[1243] [Chemical formula 219]

[1244]

[1245] (Synthesis Example 65)

[1246] [Synthesis of Orange Dye Compound (D-13)]

[1247] The orange dye compound (D-13) was manufactured according to the following scheme.

[1248] [Chemical formula 220]

[1249]

[1250] As the coupling agent component solution, the compound of formula (C35) was used instead of the compound of formula (C18). Otherwise, the same operation as in Synthesis Example 30 was carried out to obtain the orange dye compound represented by the following formula (D-13) (16.4 g, yield 79.8%). The above orange dye compound was confirmed by LCMS analysis (m / z 411 (M + )) to confirm its structure.

[1251] [Chemical formula 221]

[1252]

[1253] (Synthesis Example 66)

[1254] [Synthesis of Blue Dye Compound (A-16)]

[1255] The blue dye compound (A-16) is produced according to the following scheme.

[1256] [Chemical Formula 222]

[1257]

[1258] 66-A. Synthesis of Coupling Agent Compound C8 and Preparation of Coupling Agent Component Solution

[1259] (Step 1)

[1260] 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. Otherwise, the same operations as in Steps 1 to 4 of Synthesis Example 1 are carried out to obtain N-[3-(N,N-dioctylamino)-4-butoxyphenyl]propanamide represented by the following formula (C36). By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C36) is obtained.

[1261] [Chemical Formula 223]

[1262]

[1263] 66-B. Synthesis of Blue Dye Compound (A-16) by Coupling Reaction

[1264] (Step 2)

[1265] As the coupling agent component solution, the compound of formula (C36) obtained in Step 1 is used instead of the compound of formula (C1). Otherwise, the same operations as in Steps 5 and 6 of Synthesis Example 1 are carried out to obtain the blue dye compound (6.45 g, yield 17.6%) represented by the following formula (A-16). The above blue dye compound is confirmed by LCMS analysis (m / z 733 (M + )) to confirm its structure.

[1266] [Chemical Formula 224]

[1267]

[1268] (Synthesis Example 67)

[1269] [Synthesis of Red Dye Compound (C-19)]

[1270] The red dye compound (C-19) is produced according to the following scheme.

[1271] [Chemical formula 225]

[1272]

[1273] 67-A. Synthesis of Coupling Agent Compound C37 and Preparation of Coupling Agent Component Solution

[1274] (Step 1)

[1275] In Step 1 of Synthesis Example 9, propionyl chloride (19.4 g) was used instead of n-octanoyl chloride, and 1-bromohexane (33.0 g) was used instead of 1-bromooctane in Step 3 of Synthesis Example 9. Otherwise, the same operations as in Steps 1 to 3 of Synthesis Example 9 were carried out to obtain N-[3-(N,N-dihexylamino)phenyl]propanamide represented by the following formula (C37). By adding methanol (30 g) to the reaction mixture and cooling to 5 °C, a coupling agent component solution containing the compound of formula (C37) was obtained.

[1276] [Chemical formula 226]

[1277]

[1278] 67-B. Synthesis of Red Dye Compound (C-19) by Coupling Reaction

[1279] (Step 2)

[1280] As the coupling agent component solution, the compound of formula (C37) obtained in Step 1 was used instead of the compound of formula (C9). Otherwise, the same operations as in Steps 1 and 2 of Synthesis Example 17 were carried out to obtain a red dye compound (17.6 g, yield 68.2%) represented by the following formula (C-19). The above red dye compound was confirmed for its structure by LCMS analysis (m / z 516 (M + ))

[1281] [Chemical formula 227]

[1282]

[1283] (Synthesis Example 68)

[1284] [Synthesis of Red Dye Compound (C-20)]

[1285] The red dye compound (C-20) was manufactured according to the following scheme.

[1286] [Chemical formula 228]

[1287]

[1288] As a coupling agent component solution, a compound of formula (C12) was used in place of the compound of formula (C18), and otherwise, the same operations as in Steps 1 and 2 of Synthesis Example 30 were carried out to obtain a red dye compound represented by the following formula (C-20) (23.0 g, yield 87.7%). The above red dye compound was confirmed for its structure by LCMS analysis (m / z 524 (M + ))

[1289] [Chemical formula 229]

[1290]

[1291] (Synthesis Example 69)

[1292] [Synthesis of blue dye compound (A-17)]

[1293] The blue dye compound (A-17) was produced according to the following scheme.

[1294] [Chemical formula 230]

[1295]

[1296] 69-A. Synthesis of coupling agent compound C38 and preparation of coupling agent component solution

[1297] (Step 1)

[1298] In Step 1 of Synthesis Example 1, valeryl chloride (25.3 g) was used in place of n-octanoyl chloride, and in Step 4, 1-bromohexane (33.0 g) was used in place of 1-bromooctane, and otherwise, the same operations as in Steps 1 to 4 of Synthesis Example 1 were carried out to obtain N-[3-(N,N-dihexylamino)-4-methoxyphenyl]pentanamide represented by the following formula (C38). By adding methanol (30 g) to the reaction mixture and cooling to 5°C, a coupling agent component solution containing the compound of formula (C38) was obtained.

[1299] [Chemical formula 231]

[1300]

[1301] 69-B. Synthesis of blue dye compound (A-17) by coupling reaction

[1302] (Step 2)

[1303] As a coupling agent component solution, the compound of formula (C38) obtained in Step 1 was used in place of the compound of formula (C1), and otherwise, the same operations as in Steps 5 and 6 of Synthesis Example 1 were carried out to obtain a blue dye compound (15.3 g, yield 48.4%) represented by the following formula (A-17). The structure of the above blue dye compound was confirmed by LCMS analysis (m / z 663 (M + ))

[1304] [Chemical formula 232]

[1305]

[1306] The structural formulas of the dye compounds described in the synthesis examples and conventional dye compounds are shown in Tables 3 to 9

[1307] Table 3

[1308]

[1309]

[1310] Table 4

[1311]

[1312]

[1313] Table 5

[1314]

[1315]

[1316] Table 6

[1317]

[1318] Synthesis Example Compound <![CDATA[X D > <![CDATA[Y D > <![CDATA[R D1 > <![CDATA[R D2 > 24 D-1 Cl Cl <![CDATA[C8H 17 > <![CDATA[C8H 17 > 25 D-2 Cl Cl <![CDATA[C 12 H 25 > <![CDATA[C 12 H 25 > 26 D-3 Cl Cl <![CDATA[C4H9]]> <![CDATA[C4H9]]> 30 D-4 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > 31 D-5 Br Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > 32 D-6 Br Br <![CDATA[C4H9]]> <![CDATA[C4H9 <!-- 89 -->]]> 35 D-7 H CN <![CDATA[C8H 17 > <![CDATA[C8H 17 > 49 D-8 Cl Cl <![CDATA[C2H5]]> <![CDATA[C2H5]]> 50 D-9 Br Br <![CDATA[C2H5]]> <![CDATA[C2H5]]> 51 D-10 H H <![CDATA[C2H5]]> <![CDATA[C2H5]]> 52 D-11 H H <![CDATA[C8H 17 > <![CDATA[C2H4CN]]> 64 D-12 Cl Cl <![CDATA[C6H 13 > <![CDATA[C6H 13 > 65 D-13 H H <![CDATA[C6H 13 > <![CDATA[C6H 13 >

[1319] Table 7

[1320]

[1321] Synthesis Example Compound <![CDATA[X E > <![CDATA[Y E > <![CDATA[R E > 33 E-1 Cl Cl <![CDATA[C8H 17 > 34 E-2 Cl Cl <![CDATA[C4H9]]>

[1322] Table 8

[1323]

[1324] Synthesis Example Compound <![CDATA[R F1 > <![CDATA[R F2 > 29 F-1 <![CDATA[C8H 17 > <![CDATA[C8H 17 > 54 F-2 <![CDATA[C2H5]]> <![CDATA[C2H5]]>

[1325] Table 9

[1326]

[1327] Synthesis Example Compound <![CDATA[R G > 27 G-1 <![CDATA[-CH(C6H 13 )C8H 17 > 28 G-2 <![CDATA[C7H 15 > 45 G-3 <![CDATA[-CH(C2H5)C4H9]]> 46 G-4 <![CDATA[C8H 17 >

[1328] <Manufacturing Examples of Dye Compositions>

[1329] For aqueous dyeing, dye compositions of the compounds described in Tables 3 to 9 were manufactured. The following are the manufacturing examples. In this manufacturing example, the dye compositions are in the form of liquid aqueous dispersions or powders. Specifically, Manufacturing Examples 1 to 105 of the dye compositions are manufacturing examples of liquid dye compositions, and Manufacturing Examples 106 to 141 of the dye compositions are manufacturing examples of powder dye compositions. It should be noted that the volume median diameter of the compounds in the dye compositions was measured using a dynamic light scattering particle size distribution measuring device LB-500 manufactured by Horiba, Ltd.

[1330] (Manufacturing Example 1 of Dye Composition)

[1331] 20 g of a stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant was dissolved in 60 g of water. 20 g of Compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a Compound A-5 dye composition with a volume median diameter of 0.17 μm and a concentration of 20% by mass.

[1332] (Manufacturing Example 2 of Dye Composition)

[1333] 4 g of a stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant was dissolved in 76 g of water. 20 g of Compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a Compound A-5 dye composition with a volume median diameter of 0.20 μm and a concentration of 20% by mass.

[1334] (Manufacturing Example 3 of Dye Composition)

[1335] 10 g of a stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant was dissolved in 70 g of water. 20 g of Compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a Compound A-5 dye composition with a volume median diameter of 0.16 μm and a concentration of 20% by mass.

[1336] (Manufacturing Example 4 of Dye Composition)

[1337] 30 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 50 g of water. 20 g of compound A - 5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a compound A - 5 dye composition having a volume median diameter of 0.19 μm and a concentration of 20 mass%.

[1338] (Dye Composition Production Example 5)

[1339] 20 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 50 g of water, and then 10 g of propylene glycol was dissolved therein. 20 g of compound A - 5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a compound A - 5 dye composition having a volume median diameter of 0.19 μm and a concentration of 20 mass%.

[1340] (Dye Composition Production Example 6)

[1341] 20 g of a triphenylenized phenol - ethylene oxide 50 - mole adduct as a dispersant was dissolved in 60 g of water. 20 g of compound A - 5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a compound A - 5 dye composition having a volume median diameter of 0.19 μm and a concentration of 20 mass%.

[1342] (Dye Composition Production Example 7)

[1343] 20 g of a tribenzylphenol - ethylene oxide 23 - mole adduct as a dispersant was dissolved in 60 g of water. 20 g of compound A - 5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a compound A - 5 dye composition having a volume median diameter of 0.15 μm and a concentration of 20 mass%.

[1344] (Dye Composition Production Example 8)

[1345] 20 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out for 20 hours using a vertical bead mill to obtain a compound A - 3 dye composition having a volume median diameter of 0.12 μm and a concentration of 20 mass%.

[1346] (Dye Composition Production Example 9)

[1347] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct and 10 g of a tristyrenated phenol - ethylene oxide 50 - mole adduct as dispersants were 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out for 20 hours using a vertical bead mill to obtain a compound A - 3 dye composition having a volume median diameter of 0.14 μm and a concentration of 20 mass%.

[1348] (Dye Composition Production Example 10)

[1349] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct and 10 g of a tribenzylphenol - ethylene oxide 23 - mole adduct as dispersants were 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out for 20 hours using a vertical bead mill to obtain a compound A - 3 dye composition having a volume median diameter of 0.12 μm and a concentration of 20 mass%.

[1350] (Dye Composition Production Example 11)

[1351] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct and 10 g of sodium lignosulfonate as dispersants were 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out for 20 hours using a vertical bead mill to obtain a compound A - 3 dye composition having a volume median diameter of 0.16 μm and a concentration of 20 mass%.

[1352] (Dye Composition Production Example 12)

[1353] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 10 g of a sulfate sodium salt of a tristilbenized phenol - ethylene oxide 29 - mole adduct were 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a compound A - 3 dye composition having a volume median diameter of 0.15 μm and a concentration of 20 mass%.

[1354] (Dye Composition Production Example 13)

[1355] 20 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a compound A - 1 dye composition having a volume median diameter of 0.27 μm and a concentration of 20 mass%.

[1356] (Dye Composition Production Example 14)

[1357] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a compound B - 4 dye composition having a volume median diameter of 0.22 μm and a concentration of 20 mass%.

[1358] (Dye Composition Production Example 15)

[1359] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 60 g of water, and then 10 g of propylene glycol was dissolved. 20 g of the compound B - 4 obtained in Synthesis Example 12 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a compound B - 4 dye composition having a volume median diameter of 0.20 μm and a concentration of 20 mass%.

[1360] (Dye Composition Production Example 16)

[1361] 20 g of a stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a compound B-3 dye composition having a volume median diameter of 0.17 μm and a concentration of 20% by mass.

[1362] (Dye Composition Production Example 17)

[1363] 20 g of a triphenylenized phenol-ethylene oxide 50-mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a compound B-3 dye composition having a volume median diameter of 0.15 μm and a concentration of 20% by mass.

[1364] (Dye Composition Production Example 18)

[1365] 20 g of a tribenzyl phenol-ethylene oxide 23-mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a dye composition of compound B-3 having a volume median diameter of 0.16 μm and a concentration of 20% by mass.

[1366] (Dye Composition Production Example 19)

[1367] 20 g of a stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant was dissolved in 50 g of water, and then 10 g of propylene glycol was dissolved. 20 g of the compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a compound B-3 dye composition having a volume median diameter of 0.16 μm and a concentration of 20% by mass.

[1368] (Dye Composition Production Example 20)

[1369] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 70 g of water. 20 g of Compound B - 1 obtained in Synthesis Example 9 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a Compound B - 1 dye composition having a volume median diameter of 0.22 μm and a concentration of 20 mass%.

[1370] (Dye Composition Production Example 21)

[1371] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 70 g of water. 20 g of Compound B - 10 obtained in Synthesis Example 48 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a Compound B - 10 dye composition having a volume median diameter of 0.24 μm and a concentration of 20 mass%.

[1372] (Dye Composition Production Example 22)

[1373] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 76 g of water. 20 g of Compound C - 4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a Compound C - 4 dye composition having a volume median diameter of 0.29 μm and a concentration of 20 mass%.

[1374] (Dye Composition Production Example 23)

[1375] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 70 g of water. 20 g of Compound C - 4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a Compound C - 4 dye composition having a volume median diameter of 0.24 μm and a concentration of 20 mass%.

[1376] (Dye Composition Production Example 24)

[1377] 20 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and subjected to a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound C - 4 dye composition having a volume - median diameter of 0.22 μm and a concentration of 20 mass%.

[1378] (Dye Composition Production Example 25)

[1379] 30 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and subjected to a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound C - 4 dye composition having a volume - median diameter of 0.24 μm and a concentration of 20 mass%.

[1380] (Dye Composition Production Example 26)

[1381] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 60 g of water, and then 10 g of diethylene glycol was dissolved. 20 g of the compound C - 4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and subjected to a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound C - 4 dye composition having a volume - median diameter of 0.20 μm and a concentration of 20 mass%.

[1382] (Dye Composition Production Example 27)

[1383] 20 g of a triphenylenized phenol - ethylene oxide 50 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and subjected to a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound C - 4 dye composition having a volume - median diameter of 0.25 μm and a concentration of 20 mass%.

[1384] (Dye Composition Production Example 28)

[1385] 20 g of tribenzylphenol-ethylene oxide 23-mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was performed for 20 hours using a vertical bead mill to obtain a compound C-4 dye composition having a volume median diameter of 0.24 μm and a concentration of 20% by mass.

[1386] (Dye Composition Production Example 29)

[1387] 20 g of stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was performed for 20 hours using a vertical bead mill to obtain a compound C-3 dye composition having a volume median diameter of 0.25 μm and a concentration of 20% by mass.

[1388] (Dye Composition Production Example 30)

[1389] 20 g of triphenylstilbenized phenol-ethylene oxide 50-mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was performed for 20 hours using a vertical bead mill to obtain a compound C-3 dye composition having a volume median diameter of 0.26 μm and a concentration of 20% by mass.

[1390] (Dye Composition Production Example 31)

[1391] 20 g of tribenzylphenol-ethylene oxide 23-mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was performed for 20 hours using a vertical bead mill to obtain a compound C-3 dye composition having a volume median diameter of 0.25 μm and a concentration of 20% by mass.

[1392] (Dye Composition Production Example 32)

[1393] 20 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 50 g of water, and then 10 g of ethylene glycol was dissolved therein. 20 g of the compound C - 3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and subjected to a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound C - 3 dye composition having a volume median diameter of 0.24 μm and a concentration of 20 mass%.

[1394] (Dye Composition Production Example 33)

[1395] 20 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and subjected to a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound C - 1 dye composition having a volume median diameter of 0.20 μm and a concentration of 20 mass%.

[1396] (Dye Composition Production Example 34)

[1397] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and subjected to a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound D - 3 dye composition having a volume median diameter of 0.10 μm and a concentration of 20 mass%.

[1398] (Dye Composition Production Example 35)

[1399] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 60 g of water, and then 10 g of dipropylene glycol was dissolved therein. 20 g of the compound D - 3 obtained in Synthesis Example 26 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and subjected to a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound D - 3 dye composition having a volume median diameter of 0.10 μm and a concentration of 20 mass%.

[1400] (Dye Composition Production Example 36)

[1401] Dissolve 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct, which serves as a dispersant, in 70 g of water. Add 20 g of the compound D - 1 obtained in Synthesis Example 24 thereto and stir to prepare an aqueous slurry. With respect to this aqueous slurry, use 200 g of glass beads with a diameter of 0.3 mm and perform a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound D - 1 dye composition having a volume - median particle diameter of 0.27 μm and a concentration of 20 mass%.

[1402] (Dye Composition Production Example 37)

[1403] Dissolve 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct, which serves as a dispersant, in 70 g of water. Add 20 g of the compound D - 6 obtained in Synthesis Example 32 thereto and stir to prepare an aqueous slurry. With respect to this aqueous slurry, use 200 g of glass beads with a diameter of 0.3 mm and perform a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound D - 6 dye composition having a volume - median particle diameter of 0.12 μm and a concentration of 20 mass%.

[1404] (Dye Composition Production Example 38)

[1405] Dissolve 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct, which serves as a dispersant, in 60 g of water, and then dissolve 10 g of ethylene glycol. Add 20 g of the compound D - 6 obtained in Synthesis Example 32 thereto and stir to prepare an aqueous slurry. With respect to this aqueous slurry, use 200 g of glass beads with a diameter of 0.3 mm and perform a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound D - 6 dye composition having a volume - median particle diameter of 0.10 μm and a concentration of 20 mass%.

[1406] (Dye Composition Production Example 39)

[1407] Dissolve 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct, which serves as a dispersant, in 70 g of water. Add 20 g of the compound D - 5 obtained in Synthesis Example 31 thereto and stir to prepare an aqueous slurry. With respect to this aqueous slurry, use 200 g of glass beads with a diameter of 0.3 mm and perform a fine - particle dispersion treatment for 20 hours using a vertical bead mill to obtain a compound D - 5 dye composition having a volume - median particle diameter of 0.26 μm and a concentration of 20 mass%.

[1408] (Dye Composition Production Example 40)

[1409] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out for 20 hours using a vertical bead mill to obtain a compound D - 4 dye composition having a volume median diameter of 0.13 μm and a concentration of 20 mass%.

[1410] (Dye Composition Production Example 41)

[1411] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out for 20 hours using a vertical bead mill to obtain a compound D - 4 dye composition having a volume median diameter of 0.20 μm and a concentration of 20 mass%.

[1412] (Dye Composition Production Example 42)

[1413] 20 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out for 20 hours using a vertical bead mill to obtain a compound D - 4 dye composition having a volume median diameter of 0.11 μm and a concentration of 20 mass%.

[1414] (Dye Composition Production Example 43)

[1415] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 60 g of water, and then 10 g of propylene glycol was dissolved therein. 20 g of the compound D - 4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out for 20 hours using a vertical bead mill to obtain a compound D - 4 dye composition having a volume median diameter of 0.13 μm and a concentration of 20 mass%.

[1416] (Dye Composition Production Example 44)

[1417] 10 g of a stilbenized phenol - ethylene oxide 58 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out for 20 hours using a vertical bead mill to obtain a compound D - 4 dye composition having a volume median diameter of 0.15 μm and a concentration of 20 mass%.

[1418] (Dye Composition Production Example 45)

[1419] 10 g of a tribenzylphenol - ethylene oxide 50 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out for 20 hours using a vertical bead mill to obtain a compound D - 4 dye composition having a volume median diameter of 0.15 μm and a concentration of 20 mass%.

[1420] (Dye Composition Production Example 46)

[1421] 10 g of a tribenzylphenol - ethylene oxide 23 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out for 20 hours using a vertical bead mill to obtain a compound D - 4 dye composition having a volume median diameter of 0.18 μm and a concentration of 20 mass%.

[1422] (Dye Composition Production Example 47)

[1423] 10 g of a tribenzylphenol - ethylene oxide 40 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out for 20 hours using a vertical bead mill to obtain a compound D - 4 dye composition having a volume median diameter of 0.16 μm and a concentration of 20 mass%.

[1424] (Dye Composition Production Example 48)

[1425] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a compound G - 1 dye composition having a volume median diameter of 0.23 μm and a concentration of 20 mass%.

[1426] (Dye Composition Production Example 49)

[1427] 10 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant was dissolved in 60 g of water, and then 10 g of polyethylene glycol (average molecular weight 400) was dissolved therein. 20 g of the compound G - 1 obtained in Synthesis Example 27 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 20 hours to obtain a compound G - 1 dye composition having a volume median diameter of 0.30 μm and a concentration of 20 mass%.

[1428] (Dye Composition Production Example 50)

[1429] 20 g of a formaldehyde condensate of naphthalenesulfonic acid sodium 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and an attempt was made to carry out micronization treatment using a vertical bead mill. However, micronization could not be carried out, and a dye composition could not be obtained.

[1430] (Dye Composition Production Example 51)

[1431] 20 g of sodium lignosulfonate 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and an attempt was made to carry out micronization treatment using a vertical bead mill. However, micronization could not be carried out, and a dye composition could not be obtained.

[1432] (Dye Composition Production Example 52)

[1433] 20 g of the sodium sulfate ester of a triphenylethylenated phenol - ethylene oxide 29 - mole adduct, which is used 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out, and a dye composition could not be obtained.

[1434] (Dye Composition Production Example 53)

[1435] 20 g of a formaldehyde condensate of sodium naphthalenesulfonate, which is used as a dispersant, was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out, and a dye composition could not be obtained.

[1436] (Dye Composition Production Example 54)

[1437] 20 g of sodium lignosulfonate, which is used as a dispersant, was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out, and a dye composition could not be obtained.

[1438] (Dye Composition Production Example 55)

[1439] 20 g of the sodium sulfate ester of a triphenylethylenated phenol - ethylene oxide 29 - mole adduct, which is used as a dispersant, was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out, and a dye composition could not be obtained.

[1440] (Dye Composition Production Example 56)

[1441] 20 g of a formaldehyde condensate of sodium naphthalenesulfonate, which is used as a dispersant, was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out.

[1442] (Dye Composition Production Example 57)

[1443] 20 g of a formaldehyde condensate of sodium cresol sulfonate as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and an attempt was made to perform fine particle dispersion treatment using a vertical bead mill. However, fine particle dispersion could not be carried out.

[1444] (Production Example 58 of Dye Composition)

[1445] 20 g of sodium lignin sulfonate as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and an attempt was made to perform fine particle dispersion treatment using a vertical bead mill. However, fine particle dispersion could not be carried out, and a dye composition could not be obtained.

[1446] (Production Example 59 of Dye Composition)

[1447] 20 g of a formaldehyde condensate of sodium naphthalene sulfonate as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and an attempt was made to perform fine particle dispersion treatment using a vertical bead mill. However, fine particle dispersion could not be carried out.

[1448] (Production Example 60 of Dye Composition)

[1449] 20 g of a formaldehyde condensate of sodium cresol sulfonate as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and an attempt was made to perform fine particle dispersion treatment using a vertical bead mill. However, fine particle dispersion could not be carried out.

[1450] (Production Example 61 of Dye Composition)

[1451] 20 g of sodium lignin sulfonate as a dispersant was 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and an attempt was made to perform fine particle dispersion treatment using a vertical bead mill. However, fine particle dispersion could not be carried out, and a dye composition could not be obtained.

[1452] (Production Example 62 of Dye Composition)

[1453] 20 g of the sodium sulfate ester of triphenylethylated phenol - ethylene oxide 29 - mole adduct, which is used as a dispersant, was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out, and a dye composition could not be obtained.

[1454] (Dye Composition Preparation Example 63)

[1455] 10 g of the formaldehyde condensate of sulfonated tall oil, which is used as a dispersant, and 10 g of sodium lignosulfonate were 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out, and a dye composition could not be obtained.

[1456] (Dye Composition Preparation Example 64)

[1457] 20 g of the formaldehyde condensate of naphthalenesulfonic acid sodium salt, which is used as a dispersant, was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out.

[1458] (Dye Composition Preparation Example 65)

[1459] 20 g of the formaldehyde condensate of methylnaphthalenesulfonic acid sodium salt, which is used as a dispersant, was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out.

[1460] (Dye Composition Preparation Example 66)

[1461] 20 g of sodium lignosulfonate, which is used as a dispersant, was 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and an attempt was made to perform fine - particle dispersion treatment using a vertical bead mill. However, fine - particle dispersion could not be carried out.

[1462] (Dye Composition Preparation Example 67)

[1463] 10 g of a formaldehyde condensate of naphthalenesulfonic acid sodium salt and 10 g of sodium lignosulfonate as dispersants were 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and an attempt was made to perform fine particle dispersion treatment using a vertical bead mill. However, fine particle dispersion could not be carried out, and a dye composition could not be obtained.

[1464] (Dye Composition Production Example 68)

[1465] 20 g of a stilbenized phenol-ethylene oxide 24-mole 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and fine particle dispersion treatment was carried out for 20 hours using a vertical bead mill to obtain a compound A-13 dye composition having a volume median diameter of 0.15 μm and a concentration of 20% by mass.

[1466] (Dye Composition Production Example 69)

[1467] 20 g of a stilbenized phenol-ethylene oxide 24-mole 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and fine particle dispersion treatment was carried out for 20 hours using a vertical bead mill to obtain a compound A-17 dye composition having a volume median diameter of 0.17 μm and a concentration of 20% by mass.

[1468] (Dye Composition Production Example 70)

[1469] 20 g of a stilbenized phenol-ethylene oxide 24-mole 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and fine particle dispersion treatment was carried out for 20 hours using a vertical bead mill to obtain a compound A-2 dye composition having a volume median diameter of 0.19 μm and a concentration of 20% by mass.

[1470] (Dye Composition Production Example 71)

[1471] 20 g of a stilbenized phenol - ethylene oxide 24 - mole 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a compound A - 16 dye composition having a volume median diameter of 0.18 μm and a concentration of 20 mass%.

[1472] (Dye Composition Production Example 72)

[1473] 20 g of a stilbenized phenol - ethylene oxide 24 - mole 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a compound B - 2 dye composition having a volume median diameter of 0.19 μm and a concentration of 20 mass%.

[1474] (Dye Composition Production Example 73)

[1475] 20 g of a stilbenized phenol - ethylene oxide 24 - mole 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a compound C - 19 dye composition having a volume median diameter of 0.23 μm and a concentration of 20 mass%.

[1476] (Dye Composition Production Example 74)

[1477] 20 g of a stilbenized phenol - ethylene oxide 24 - mole 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a compound C - 20 dye composition having a volume median diameter of 0.24 μm and a concentration of 20 mass%.

[1478] (Dye Composition Production Example 75)

[1479] 10 g of a stilbenized phenol - ethylene oxide 24 - mole 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and a fine particle dispersion treatment was carried out using a vertical bead mill for 20 hours to obtain a compound D - 13 dye composition having a volume median diameter of 0.13 μm and a concentration of 20 mass%.

[1480] (Dye Composition Production Example 76)

[1481] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 10 g of an oxyethylene(300 moles) - oxypropylene(55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and a fine particle dispersion treatment was carried out using a vertical bead mill for 24 hours to obtain a compound A - 13 dye composition having a volume median diameter of 0.16 μm and a concentration of 20 mass%.

[1482] (Dye Composition Production Example 77)

[1483] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 10 g of an oxyethylene(300 moles) - oxypropylene(55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and a fine particle dispersion treatment was carried out using a vertical bead mill for 24 hours to obtain a compound A - 5 dye composition having a volume median diameter of 0.17 μm and a concentration of 20 mass%.

[1484] (Dye Composition Production Example 78)

[1485] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 10 g of an oxyethylene(300 moles) - oxypropylene(55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and a fine particle dispersion treatment was carried out using a vertical bead mill for 24 hours to obtain a compound A - 5 dye composition having a volume median diameter of 0.15 μm and a concentration of 20 mass%.

[1486] (Dye Composition Production Example 79)

[1487] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 10 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 24 hours to obtain a compound A - 3 dye composition having a volume - median particle size of 0.15 μm and a concentration of 20 mass%.

[1488] (Dye Composition Production Example 80)

[1489] 4 g of a stilbenized phenol - ethylene oxide 58 - mole adduct as a dispersant and 10 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 24 hours to obtain a compound A - 3 dye composition having a volume - median particle size of 0.15 μm and a concentration of 20 mass%.

[1490] (Dye Composition Production Example 81)

[1491] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 10 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 24 hours to obtain a compound A - 2 dye composition having a volume - median particle size of 0.18 μm and a concentration of 20 mass%.

[1492] (Dye Composition Production Example 82)

[1493] 8 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 8 g of an ethylene oxide (360 moles) - propylene oxide (70 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out using a vertical bead mill for 24 hours to obtain a compound A - 4 dye composition having a volume - median particle size of 0.18 μm and a concentration of 20 mass%.

[1494] (Dye Composition Production Example 83)

[1495] 8 g of a 58-mole adduct of stilbenized phenol - ethylene oxide as a dispersant and 8 g of an ethylene oxide (360 moles) - propylene oxide (70 moles) copolymer were dissolved in 64 g of water. 20 g of Compound A-1 obtained in Synthesis Example 1 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out for 24 hours using a vertical bead mill to obtain a Compound A-1 dye composition having a volume median diameter of 0.20 μm and a concentration of 20% by mass.

[1496] (Dye Composition Production Example 84)

[1497] 8 g of a 24-mole adduct of stilbenized phenol - ethylene oxide as a dispersant and 8 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) copolymer were dissolved in 64 g of water. 20 g of Compound B-4 obtained in Synthesis Example 12 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out for 24 hours using a vertical bead mill to obtain a Compound B-4 dye composition having a volume median diameter of 0.22 μm and a concentration of 20% by mass.

[1498] (Dye Composition Production Example 85)

[1499] 8 g of a 24-mole adduct of stilbenized phenol - ethylene oxide as a dispersant and 8 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) copolymer were dissolved in 64 g of water. 20 g of Compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out for 24 hours using a vertical bead mill to obtain a Compound B-3 dye composition having a volume median diameter of 0.19 μm and a concentration of 20% by mass.

[1500] (Dye Composition Production Example 86)

[1501] 4 g of a 24-mole adduct of stilbenized phenol - ethylene oxide as a dispersant and 10 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) copolymer were dissolved in 66 g of water. 20 g of Compound B-2 obtained in Synthesis Example 10 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out for 24 hours using a vertical bead mill to obtain a Compound B-2 dye composition having a volume median diameter of 0.23 μm and a concentration of 20% by mass.

[1502] (Dye Composition Production Example 87)

[1503] 8 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 8 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out for 24 hours using a vertical bead mill to obtain a compound B - 2 dye composition having a volume median diameter of 0.22 μm and a concentration of 20 mass%.

[1504] (Dye Composition Production Example 88)

[1505] 8 g of a stilbenized phenol - ethylene oxide 58 - mole adduct as a dispersant and 8 g of an ethylene oxide (360 moles) - propylene oxide (70 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out for 24 hours using a vertical bead mill to obtain a compound B - 1 dye composition having a volume median diameter of 0.20 μm and a concentration of 20 mass%.

[1506] (Dye Composition Production Example 89)

[1507] 8 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 8 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out for 24 hours using a vertical bead mill to obtain a compound B - 10 dye composition having a volume median diameter of 0.24 μm and a concentration of 20 mass%.

[1508] (Dye Composition Production Example 90)

[1509] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 10 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micron - dispersion treatment was carried out for 24 hours using a vertical bead mill to obtain a compound C - 4 dye composition having a volume median diameter of 0.24 μm and a concentration of 20 mass%.

[1510] (Dye Composition Production Example 91)

[1511] 8 g of a stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant and 8 g of an ethylene oxide (300 moles)-propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound C-4 dye composition having a volume median diameter of 0.23 μm and a concentration of 20% by mass.

[1512] (Dye Composition Production Example 92)

[1513] 4 g of a stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant and 10 g of an ethylene oxide (300 moles)-propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound C-3 dye composition having a volume median diameter of 0.25 μm and a concentration of 20% by mass.

[1514] (Dye Composition Production Example 93)

[1515] 8 g of a stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant and 8 g of an ethylene oxide (300 moles)-propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound C-3 dye composition having a volume median diameter of 0.25 μm and a concentration of 20% by mass.

[1516] (Dye Composition Production Example 94)

[1517] 8 g of a stilbenized phenol-ethylene oxide 24-mole adduct as a dispersant and 8 g of an ethylene oxide (300 moles)-propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads having a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound C-2 dye composition having a volume median diameter of 0.22 μm and a concentration of 20% by mass.

[1518] (Dye Composition Production Example 95)

[1519] 8 g of triphenylethylenated phenol - ethylene oxide 50 - mole adduct as a dispersant and 8 g of ethylene oxide (300 moles) - propylene oxide (55 moles) copolymer 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound C - 1 dye composition having a volume median diameter of 0.20 μm and a concentration of 20 mass%.

[1520] (Dye Composition Production Example 96)

[1521] 4 g of styrylated phenol - ethylene oxide 24 - mole adduct as a dispersant and 8 g of ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound C - 20 dye composition having a volume median diameter of 0.18 μm and a concentration of 20 mass%.

[1522] (Dye Composition Production Example 97)

[1523] 8 g of styrylated phenol - ethylene oxide 24 - mole adduct as a dispersant and 8 g of ethylene oxide (160 moles) - propylene oxide (60 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound D - 3 dye composition having a volume median diameter of 0.14 μm and a concentration of 20 mass%.

[1524] (Dye Composition Production Example 98)

[1525] 8 g of styrylated phenol - ethylene oxide 24 - mole adduct as a dispersant and 8 g of ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound D - 1 dye composition having a volume median diameter of 0.23 μm and a concentration of 20 mass%.

[1526] (Dye Composition Production Example 99)

[1527] 8 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 8 g of an ethylene oxide (160 moles) - propylene oxide (60 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out for 24 hours using a vertical bead mill to obtain a compound D - 6 dye composition having a volume median diameter of 0.14 μm and a concentration of 20 mass%.

[1528] (Dye Composition Production Example 100)

[1529] 8 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 8 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out for 24 hours using a vertical bead mill to obtain a compound D - 5 dye composition having a volume median diameter of 0.24 μm and a concentration of 20 mass%.

[1530] (Dye Composition Production Example 101)

[1531] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 10 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out for 24 hours using a vertical bead mill to obtain a compound D - 13 dye composition having a volume median diameter of 0.18 μm and a concentration of 20 mass%.

[1532] (Dye Composition Production Example 102)

[1533] 4 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 10 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out for 24 hours using a vertical bead mill to obtain a compound D - 4 dye composition having a volume median diameter of 0.20 μm and a concentration of 20 mass%.

[1534] (Dye Composition Production Example 103)

[1535] 8 g of a tribenzylphenol - ethylene oxide 40 - mole adduct as a dispersant and 8 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) copolymer 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound E - 1 dye composition having a volume median diameter of 0.24 μm and a concentration of 20 mass%.

[1536] (Dye Composition Production Example 104)

[1537] 8 g of a dibenzylstilbenized phenol - ethylene oxide 23 - mole adduct as a dispersant and 8 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) copolymer were dissolved in 64 g of water. 20 g of the compound F - 1 obtained in Synthesis Example 29 was added thereto and stirred to prepare an aqueous slurry. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound F - 1 dye composition having a volume median diameter of 0.24 μm and a concentration of 20 mass%.

[1538] (Dye Composition Production Example 105)

[1539] 8 g of a stilbenized phenol - ethylene oxide 24 - mole adduct as a dispersant and 8 g of an ethylene oxide (300 moles) - propylene oxide (55 moles) 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. With respect to this aqueous slurry, 200 g of glass beads with a diameter of 0.3 mm were used, and micronization treatment was carried out using a vertical bead mill for 24 hours to obtain a compound G - 1 dye composition having a volume median diameter of 0.23 μm and a concentration of 20 mass%.

[1540] (Dye Composition Production Example 106)

[1541] 33 g of a formaldehyde condensate of naphthalenesulfonic acid and 17 g of water were added to 50 g of a 20 - mass% compound A - 13 dye composition 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 with a concentration of 20 mass%.

[1542] (Dye Composition Production Example 107)

[1543] To 50 g of the compound A-5 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 77, 33 g of a formaldehyde condensate of naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound A-5 at a concentration of 20% by mass.

[1544] (Dye Composition Production Example 108)

[1545] To 50 g of the compound A-5 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 77, 33 g of a formaldehyde condensate of methylnaphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound A-5 at a concentration of 20% by mass.

[1546] (Dye Composition Production Example 109)

[1547] To 50 g of the compound A-5 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 77, 33 g of a formaldehyde condensate of cresol sulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound A-5 at a concentration of 20% by mass.

[1548] (Dye Composition Production Example 110)

[1549] To 50 g of the compound A-5 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 77, 33 g of lignosulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound A-5 at a concentration of 20% by mass.

[1550] (Dye Composition Production Example 111)

[1551] To 50 g of the compound A-3 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 79, 33 g of a formaldehyde condensate of naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound A-3 at a concentration of 20% by mass.

[1552] (Dye Composition Production Example 112)

[1553] To 50 g of the compound A-3 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 79, 33 g of a formaldehyde condensate of methylnaphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound A-3 at a concentration of 20% by mass.

[1554] (Production Example 113 of Dye Composition)

[1555] To 50 g of the compound A-2 dye composition with a concentration of 20% by mass described in Production Example 81 of the dye composition, 33 g of a formaldehyde condensate of naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound A-2 with a concentration of 20% by mass.

[1556] (Production Example 114 of Dye Composition)

[1557] To 50 g of the compound B-3 dye composition with a concentration of 20% by mass described in Production Example 85 of the dye composition, 32 g of a formaldehyde condensate of naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound B-3 with a concentration of 20% by mass.

[1558] (Production Example 115 of Dye Composition)

[1559] To 50 g of the compound B-2 dye composition with a concentration of 20% by mass described in Production Example 87 of the dye composition, 32 g of a formaldehyde condensate of naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound B-2 with a concentration of 20% by mass.

[1560] (Production Example 116 of Dye Composition)

[1561] To 50 g of the compound B-2 dye composition with a concentration of 20% by mass described in Production Example 87 of the dye composition, 32 g of a formaldehyde condensate of methylnaphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound B-2 with a concentration of 20% by mass.

[1562] (Production Example 117 of Dye Composition)

[1563] To 50 g of the compound B-2 dye composition with a concentration of 20% by mass described in Production Example 87 of the dye composition, 32 g of lignosulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound B-2 with a concentration of 20% by mass.

[1564] (Production Example 118 of Dye Composition)

[1565] To 50 g of the compound B-1 dye composition with a concentration of 20% by mass described in Dye Composition Production Example 88, 32 g of a formaldehyde condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound B-1 with a concentration of 20% by mass.

[1566] (Dye Composition Production Example 119)

[1567] To 50 g of the compound B-10 dye composition with a concentration of 20% by mass described in Dye Composition Production Example 89, 32 g of a formaldehyde condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound B-10 with a concentration of 20% by mass.

[1568] (Dye Composition Production Example 120)

[1569] To 50 g of the compound C-4 dye composition with a concentration of 20% by mass described in Dye Composition Production Example 90, 33 g of a formaldehyde condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound C-4 with a concentration of 20% by mass.

[1570] (Dye Composition Production Example 121)

[1571] To 50 g of the compound C-4 dye composition with a concentration of 20% by mass described in Dye Composition Production Example 90, 33 g of a formaldehyde condensate of sodium methylnaphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound C-4 with a concentration of 20% by mass.

[1572] (Dye Composition Production Example 122)

[1573] To 50 g of the compound C-4 dye composition with a concentration of 20% by mass described in Dye Composition Production Example 90, 33 g of a formaldehyde condensate of sodium cresol sulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound C-4 with a concentration of 20% by mass.

[1574] (Dye Composition Production Example 123)

[1575] To 50 g of the compound C-4 dye composition with a concentration of 20% by mass described in Dye Composition Production Example 90, 33 g of sodium lignosulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound C-4 with a concentration of 20% by mass.

[1576] (Production Example 124 of Dye Composition)

[1577] To 50 g of the compound C-3 dye composition with a concentration of 20% by mass described in Production Example 92 of the dye composition, 33 g of a formaldehyde condensate of naphthalenesulfonic acid sodium salt and 17 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound C-3 with a concentration of 20% by mass.

[1578] (Production Example 125 of Dye Composition)

[1579] To 50 g of the compound C-3 dye composition with a concentration of 20% by mass described in Production Example 92 of the dye composition, 33 g of a formaldehyde condensate of methylnaphthalenesulfonic acid sodium salt and 17 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound C-3 with a concentration of 20% by mass.

[1580] (Production Example 126 of Dye Composition)

[1581] To 50 g of the compound C-20 dye composition with a concentration of 20% by mass described in Production Example 96 of the dye composition, 33 g of a formaldehyde condensate of naphthalenesulfonic acid sodium salt and 17 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound C-20 with a concentration of 20% by mass.

[1582] (Production Example 127 of Dye Composition)

[1583] To 50 g of the compound C-20 dye composition with a concentration of 20% by mass described in Production Example 96 of the dye composition, 33 g of a formaldehyde condensate of cresylic acid sulfonic acid sodium salt and 17 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound C-20 with a concentration of 20% by mass.

[1584] (Production Example 128 of Dye Composition)

[1585] To 50 g of the compound D-1 dye composition with a concentration of 20% by mass described in Production Example 98 of the dye composition, 32 g of a formaldehyde condensate of naphthalenesulfonic acid sodium salt and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-1 with a concentration of 20% by mass.

[1586] (Production Example 129 of Dye Composition)

[1587] To 50 g of the compound D-1 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 98, 32 g of a formaldehyde condensate of sodium methylnaphthalenesulfonate and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-1 at a concentration of 20% by mass.

[1588] (Dye Composition Production Example 130)

[1589] To 50 g of the compound D-1 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 98, 32 g of sodium lignosulfonate and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-1 at a concentration of 20% by mass.

[1590] (Dye Composition Production Example 131)

[1591] To 50 g of the compound D-5 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 100, 32 g of a formaldehyde condensate of sodium naphthalenesulfonate and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-5 at a concentration of 20% by mass.

[1592] (Dye Composition Production Example 132)

[1593] To 50 g of the compound D-5 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 100, 32 g of a formaldehyde condensate of sodium methylnaphthalenesulfonate and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-5 at a concentration of 20% by mass.

[1594] (Dye Composition Production Example 133)

[1595] To 50 g of the compound D-5 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 100, 32 g of sodium lignosulfonate and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-5 at a concentration of 20% by mass.

[1596] (Dye Composition Production Example 134)

[1597] To 50 g of the compound D-13 dye composition at a concentration of 20% by mass described in Dye Composition Production Example 101, 33 g of a formaldehyde condensate of sodium naphthalenesulfonate and 17 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-13 at a concentration of 20% by mass.

[1598] (Production Example 135 of Dye Composition)

[1599] To 50 g of the compound D-4 dye composition with a concentration of 20% by mass described in Production Example 102 of the dye composition, 33 g of a formaldehyde condensate of naphthalenesulfonate and 17 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-4 with a concentration of 20% by mass.

[1600] (Production Example 136 of Dye Composition)

[1601] To 50 g of the compound D-4 dye composition with a concentration of 20% by mass described in Production Example 102 of the dye composition, 33 g of a formaldehyde condensate of naphthalenesulfonate and 17 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-4 with a concentration of 20% by mass.

[1602] (Production Example 137 of Dye Composition)

[1603] To 50 g of the compound D-4 dye composition with a concentration of 20% by mass described in Production Example 102 of the dye composition, 33 g of sodium lignosulfonate and 17 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound D-4 with a concentration of 20% by mass.

[1604] (Production Example 138 of Dye Composition)

[1605] To 50 g of the compound E-1 dye composition with a concentration of 20% by mass described in Production Example 103 of the dye composition, 32 g of sodium lignosulfonate and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound E-1 with a concentration of 20% by mass.

[1606] (Production Example 139 of Dye Composition)

[1607] To 50 g of the compound F-1 dye composition with a concentration of 20% by mass described in Production Example 104 of the dye composition, 32 g of a formaldehyde condensate of naphthalenesulfonate and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound F-1 with a concentration of 20% by mass.

[1608] (Production Example 140 of Dye Composition)

[1609] To 50 g of the compound G-1 dye composition with a concentration of 20% by mass described in Dye Composition Production Example 105, 32 g of a formaldehyde condensate of naphthalenesulfonate and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound G-1 with a concentration of 20% by mass.

[1610] (Dye Composition Production Example 141)

[1611] To 50 g of the compound G-1 dye composition with a concentration of 20% by mass described in Dye Composition Production Example 105, 32 g of a formaldehyde condensate of cresylic acid sulfonate and 18 g of water were added, and the mixture was stirred for 20 minutes. The dye dispersion was spray-dried to obtain a powdery dye composition of compound G-1 with a concentration of 20% by mass.

[1612] As the dispersant for preparing the dye composition of the compound of the present invention, nonionic dispersants such as stilbenized phenol-ethylene oxide adducts, triphenethylated phenol-ethylene oxide adducts, tribenzylphenol-ethylene oxide adducts, and ethylene oxide-propylene oxide copolymers described in Dye Composition Production Examples 1 to 49 and 68 to 105 are effective.

[1613] On the other hand, with respect to the anionic dispersants such as formaldehyde condensates of naphthalenesulfonate, formaldehyde condensates of cresylic acid sulfonate, and lignosulfonate described in Dye Composition Production Examples 50 to 67 alone, it is impossible to prepare a dye composition of the compound of the present invention with a desired particle size (volume median diameter of 1.0 μm or less).

[1614] <Dyeing Example>

[1615] (Exhaust Dyeing of Polypropylene Fibers 1)

[1616] The polypropylene fibers were dyed by the exhaust method using only one of the dye compositions of the compounds described in Tables 3 to 9 or the dye compositions of disperse dye compounds etc. conventionally used in the dyeing of polyester fibers etc. shown in Tables 3 to 9.

[1617] (Dyeing Example P1)

[1618] To 1.5 g of the dye composition of blue compound A-5 (dye concentration 20% by mass) obtained in Dye Composition Production Example 1, water and acetic acid were added to prepare a dye bath with a total amount of 2000 g and a pH of 4.5. 100 g of polypropylene fibers were immersed in the above dye bath and dyed at 120 °C for 40 minutes (0.3% o.m.f.), and then thoroughly washed and dried to obtain a blue polypropylene fiber dyed product.

[1619] (Dyeing Examples P2 to P22)

[1620] A dyed polypropylene fiber fabric was obtained by the same dyeing procedure as in Dyeing Example P1, except that the dye composition of blue compound A-5 described in Dyeing Example P1 was changed to the dye compositions of the compounds in Tables 10 to 14.

[1621] (Dyeing Example P26)

[1622] 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, 95 g of water was added and stirred to prepare a dye dispersion. Water and acetic acid were added to the dye dispersion to prepare a dye bath having a total amount of 2000 g and a pH of 4.5. 100 g of polypropylene fiber was immersed in the above dye bath and dyed at 130°C for 60 minutes (1.0% o.m.f.), and then subjected to reduction washing, water washing, and drying to obtain a blue polypropylene fiber fabric.

[1623] (Dyeing Examples P27 to P37)

[1624] A dyed polypropylene fiber fabric was obtained by the same dyeing procedure as in Dyeing Example P26, except that the powdery dye composition of blue compound A-13 described in Dyeing Example P26 was changed to the powdery dye compositions of the compounds in Tables 10 to 14.

[1625] The compounds used in Dyeing Examples P1 to P22 and Dyeing Examples P26 to P37 are shown in Tables 10 to 14.

[1626] Table 10

[1627]

[1628]

[1629] Table 11

[1630]

[1631] Dyeing Example Compound <![CDATA[R B1 > <![CDATA[R B2 > <![CDATA[R B3 > P6 B-1 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C7H 15 > P5 B-3 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> P4 B-4 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> P7 B-10 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[-CH(C2H5)C4H9]]> P8 B-X1 <![CDATA[C2H4OCH3]]> <![CDATA[C2H4OCH3]]> <![CDATA[CH3]]> P29 B-3 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> P30 B-2 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C4H9]]> P31 B-10 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[-CH(C2H5)C4H9]]>

[1632] Table 12

[1633]

[1634] Dyeing Example Compound <![CDATA[X C > <![CDATA[Y C > <![CDATA[R C1 > <![CDATA[R C2 > <![CDATA[R C3 > P11 C-1 C1 H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C7H 15 > P10 C-3 C1 H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> P9 C-4 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> P12 C-X2 Cl H <![CDATA[C2H4OCOCH3]]> <![CDATA[C2H4OCOCH3]]> <![CDATA[C2H5]]> P32 C-4 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> P33 C-3 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> P34 C-20 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]>

[1635] Table 13

[1636]

[1637] Dyeing Example Compound <![CDATA[X D > <![CDATA[Y D > <![CDATA[R D1 > <![CDATA[R D2 > P14 D-1 Cl C1 <![CDATA[C8H 17 > <![CDATA[C8H 17 > P13 D-3 Cl Cl <![CDATA[C4H9]]> <![CDATA[C4H9]]> P17 D-4 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > P16 D-5 Br Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > P15 D-6 Br Br <![CDATA[C4H9]]> <![CDATA[C4H9]]> P18 D-X1 Cl Cl <![CDATA[C2H4CN]]> <![CDATA[C2H4CN]]> P19 D-X2 Br Br <![CDATA[C2H5]]> <![CDATA[C2H4CN]]> P20 D-X3 H H <![CDATA[C2H5]]> <![CDATA[C2H4CN]]> P35 D-13 H H <![CDATA[C6H 13 > <![CDATA[C6H 13 > P36 D-4 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 >

[1638] Table 14

[1639]

[1640] Dyeing Example Compound <![CDATA[R G > P21 G-1 <![CDATA[-CH(C6H 13 )C8H 17 > P22 G-X5 <![CDATA[C3H7]]> P37 G-1 <![CDATA[-CH(C6H 13 )C8H 17 >

[1641] For the dyed polypropylene fiber fabrics obtained in the dyeing examples, dyeing property evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration fastness test, rubbing fastness test, and fastness test against hot pressing were carried out.

[1642] (1) Dyeing property evaluation

[1643] The dyeing property was evaluated based on the TotalK / S value obtained by colorimetry of the dyed fabric. Colorimetry of the dyed fabric was carried out using an integrating sphere spectrophotometer Color-Eye 5 (manufactured by GretagMacbeth) by pasting the dyed fabric on white paper and observing with a light source D65 and a 2-degree visual field.

[1644] (2) Light fastness test

[1645] The light fastness test was carried out according to the ultraviolet carbon arc lamp method of 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.), after exposing the dyed fabric for 20 hours under the condition of a blackboard temperature of 63 ± 3°C, the determination of color change and fading was carried out.

[1646] (3) Sublimation fastness test

[1647] The sublimation fastness test was carried out according to the method of JIS L0854:2013. The outline of the test method is as follows. The dyed fabric was clamped in nylon cloth, and after maintaining it at 120 ± 2°C under a load of 12.5 kPa for 80 minutes, the determination of color change, fading, and contamination of the nylon cloth was carried out.

[1648] (4) Washing fastness test

[1649] The washing fastness test was carried out according to the method of JIS L0844:2011 (A-2 type). The outline of the test method is as follows. A multi-fiber interwoven fabric was attached to the dyed fabric, and it was washed for 30 minutes at 50 ± 2°C in the presence of soap, and the determination of color change, fading, and contamination of the cotton part and nylon part of the multi-fiber interwoven fabric was carried out. In addition, the determination of contamination of the residual liquid after washing was carried out.

[1650] (5) Perspiration fastness test

[1651] The perspiration fastness test was carried out according to the method of JIS L0848:2004. The outline of the test method is as follows. A multi-fiber interwoven fabric was attached to the dyed fabric, and after being immersed in acidic artificial sweat or alkaline artificial sweat for 30 minutes, it was kept at 37 ± 2 °C under a load of 12.5 kPa for 4 hours, and then dried below 60 °C. The color change and staining of the cotton part and nylon part of the multi-fiber interwoven fabric were judged.

[1652] (6) Rubbing fastness test

[1653] The rubbing fastness test was carried out according to the method of JIS L0849:2013. The outline of the test method is as follows. Using a rubbing fastness tester RT-300 (manufactured by Dairong Scientific Instruments Co., Ltd.), 100 reciprocating rubs were applied to the dyed fabric with a dry cotton cloth or a wet cotton cloth under a load of 2 N, and the staining of the cotton cloth was judged.

[1654] (7) Fastness test against hot pressing

[1655] The fastness test against hot pressing was carried out according to the method of JIS L0850:2015 (A-2 type drying). The outline of the test method is as follows. The dyed fabric was overlapped on the cotton cloth, and after being kept at 150 °C under a load of 4 ± 1 kPa for 15 seconds by a heating plate, the color change and staining of the cotton cloth were judged.

[1656] The evaluation results of the dyeing examples of the compound of formula (A) are shown in Table 15.

[1657] Table 15

[1658]

[1659] Regarding the dyeability of the compound of formula (A), R used in dyeing examples P1, P2 and P26 to P28 A1 , R A2 and R A3 are each independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of R A1 , R A2 and R A3 is an alkyl group having 4 to 14 carbon atoms), and the dyeability of the compound is good. The disperse dyes R used in dyeing example P3, which were previously used in dyeing polyester fibers and the like A1 , R A2 and R A3 all have alkyl groups having 3 or less carbon atoms, and the dyeability is poor.

[1660] In addition, regarding the fastness of each of the compounds of formula (A), R used in dyeing examples P1, P2 and P26 to P28A1 , R A2 and R A3 are each independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of R A1 , R A2 and R A3 is an alkyl group having 4 to 14 carbon atoms) has good sublimation fastness, washing fastness, perspiration fastness, rubbing fastness, and fastness to hot pressing.

[1661] The evaluation results of the dyeing examples of the compound of formula (B) are shown in Table 16.

[1662] Table 16

[1663]

[1664] Regarding the dyeability of the compound of formula (B), R used in dyeing examples P4 to P5 and P29 to P31 B1 , R B2 are each independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms) has good dyeability. The disperse dye R used in dyeing example P8, which has been used in dyeing polyester fibers etc., i.e., R B1 or R B2 which is not an alkyl group having 1 to 14 carbon atoms, has poor dyeability.

[1665] Furthermore, regarding the fastnesses of the compound of formula (B), R used in dyeing examples P4 to P5 and P29 to P31 B1 , R B2 are each independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms) has good light fastness, sublimation fastness, washing fastness, perspiration fastness, and fastness to hot pressing.

[1666] The evaluation results of the dyeing examples of the compound of formula (C) are shown in Table 17.

[1667]

[1668] Regarding the dyeability of the compound of formula (C), R used in dyeing examples P10 and P32 to P34 C1 , R C2 and R C3 are each independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 , RC2 and R C3 in which at least one of them is an alkyl group having 4 to 14 carbon atoms) has good dyeability. The disperse dye R C1 , R C2 and R C3 in which at least one of them is an alkyl group having 3 or less carbon atoms has poor dyeability.

[1669] In addition, regarding each fastness of the compound of formula (C), R C1 , R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 , R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms) of the compound is generally good.

[1670] In addition, regarding each fastness of the compound of formula (C), R C1 , R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 , R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms) of the compound has good fastness.

[1671] The evaluation results of the dyeing examples of the compound of formula (D) are shown in Table 18.

[1672]

[1673] Regarding the dyeability of the compound of formula (D), R D1 and R D2 used in dyeing examples P13 to P17 and P35, P36 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R D1 to R D2 is an alkyl group having 4 to 14 carbon atoms) of the compound has good dyeability. However, in the case of the disperse dye used in dyeing examples P18 to P20 which has been used in dyeing of polyester fibers etc., for R D1 to R D2 the alkyl groups each have 1 to 3 carbon atoms, and its dyeability is poor.

[1674] In addition, regarding each fastness of the compound of formula (D), the larger the carbon number of R D1 and R D2 , the better.

[1675] The evaluation results of the dyeing examples of the compound of formula (G) are shown in Table 19.

[1676] Table 119

[1677]

[1678] Regarding the dyeability of the compound of formula (G), the R used in dyeing examples P21 and P37 G is a compound having an alkyl group with 7 carbon atoms or 10 to 18 carbon atoms, and has good dyeability. The R, which is a disperse dye conventionally used in dyeing polyester fibers etc., used in dyeing example P22 G is a compound having an alkyl group with 3 carbon atoms and has poor dyeability.

[1679] Regarding the fastnesses of the compound of formula (G), the R used in dyeing examples P21 and P37 G is a compound having an alkyl group with 7 carbon atoms or 10 to 18 carbon atoms and is good.

[1680] (Exhaustion dyeing of polypropylene fibers 2)

[1681] Using a dye composition in which two or more compounds described in Tables 3 to 9 are mixed, polypropylene fibers were dyed in the same manner as in dyeing example P1. For the obtained polypropylene fiber dyed fabric, dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration fastness test, rubbing fastness test, and fastness test against heat pressing were carried out. It should be noted that the dyeability is evaluated using the TotalK / S value and L*, a*, b* values obtained by colorimetry of the dyed fabric. It should be noted that the colorimetry of the dyed fabric is carried out using an integrating sphere spectrophotometer Color-Eye 5 (manufactured by GretagMacbeth), pasting the dyed fabric on white paper, and observing with light source D65 and 2-degree field of view.

[1682] The evaluation results of the dyeing examples obtained using a dye composition in which two or more compounds described in Tables 3 to 9 are mixed are shown in Table 20.

[1683]

[1684] As shown in Table 20, when the orange dye, red dye, and blue dye obtained in the present invention are mixed and used, a black dyed fabric having good dyeability and generally good fastnesses is obtained.

[1685] (Exhaustion dyeing of polyethylene fibers 1)

[1686] The polyethylene fibers were dyed by the exhaustion method using only one of the dye compositions containing the compounds described in Tables 3 to 9 or the dye compositions such as disperse dye compounds conventionally used in the dyeing of polyester fibers etc. shown in Tables 3 to 9.

[1687] (Dyeing Example E1)

[1688] To 1.5 g of the dye composition of blue compound A-5 (dye concentration 20% by mass) obtained in Dye Composition Preparation Example 1, water and acetic acid were added to prepare a dye bath with a total amount of 2000 g and a pH of 4.5. 100 g of polyethylene fibers were immersed in the above dye bath and dyed at 100 °C for 40 minutes (0.3% o.m.f.), and then thoroughly washed with water and dried to obtain a blue polyethylene fiber dyed product.

[1689] (Dyeing Examples E2 to E22)

[1690] Except for changing the dye composition of the blue compound A-5 described in Dyeing Example E1 to the dye compositions of the compounds in Tables 21 to 25, polyethylene fiber dyed products were obtained by the same dyeing procedure as in Dyeing Example E1.

[1691] (Dyeing Example E26)

[1692] To 5.0 g of the powdery dye composition of blue compound A-13 (dye concentration 20% by mass) obtained in Dye Composition Preparation Example 106, 95 g of water was added and stirred to prepare a dye dispersion. Water and acetic acid were added to this dye dispersion to prepare a dye bath with a total amount of 2000 g and a pH of 4.5. 100 g of polyethylene fibers were immersed in the above dye bath and dyed at 110 °C for 60 minutes (1.0% o.m.f.), and then thoroughly washed with water and dried to obtain a blue polypropylene fiber dyed product.

[1693] (Dyeing Examples E27 to E37)

[1694] Except for changing the powdery dye composition of the blue compound A-13 described in Dyeing Example E26 to the powdery dye compositions of the compounds in Tables 21 to 25, dyed polyethylene fiber dyed products were obtained by the same dyeing procedure as in Dyeing Example E26.

[1695] The compounds used in Dyeing Examples E1 to E22 and Dyeing Examples E26 to E37 are shown in Tables 10 to 14.

[1696] Table 21

[1697]

[1698] Dyeing Example Compound <![CDATA[X A > <![CDATA[Y A > <![CDATA[R A1 > <![CDATA[R A2 > <![CDATA[R A3 > <![CDATA[R A4 > E2 A-3 <![CDATA[NO2]]> Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> <![CDATA[CH3]]> E1 A-5 <![CDATA[NO2]]> Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> <![CDATA[CH3]]> E3 A-X3 <![CDATA[NO2]]> Br <![CDATA[C2H5]]> <![CDATA[C2H5]]> <![CDATA[CH3]]> <![CDATA[CH3]]> E26 A-13 <![CDATA[NO2]]> Br <![CDATA[C6H 13 > <![CDATA[C6H 13 > <![CDATA[CH3]]> <![CDATA[CH3]]> E27 A-3 <![CDATA[NO2]]> Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> <![CDATA[CH3]]> E28 A-2 <![CDATA[NO2]]> Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C4H9]]> <![CDATA[CH3]]>

[1699] Table 22

[1700]

[1701] Dyeing Example Compound <![CDATA[R B1 > <![CDATA[R B2 > <![CDATA[R B3 > E6 B-1 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C7H 15 > E5 B-3 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> E4 B-4 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> E7 B-10 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[-CH(C2H5)C4H9]]> E8 B-X1 <![CDATA[C2H4OCH3]]> <![CDATA[C2H4OCH3]]> <![CDATA[CH3]]> E29 B-3 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> E30 B-2 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C4H9]]> E31 B-10 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[-CH(C2H5)C4H9]]>

[1702] Table 23

[1703]

[1704] Dyeing Example Compound <![CDATA[X C > <![CDATA[Y C > <![CDATA[R C1 > <![CDATA[R C2 > <![CDATA[R C3 > E11 C-1 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C7H 15 > E10 C-3 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> E9 C-4 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> E12 C-X2 Cl H <![CDATA[C2H4OCOCH3]]> <![CDATA[C2H4OCOCH3]]> <![CDATA[C2H5]]> E32 C-4 Cl H <![CDATA[C86 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> E33 C-3 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> E34 C-20 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]>

[1705] Table 24

[1706]

[1707] Dyeing Example Compound <![CDATA[X D > <![CDATA[Y D > <![CDATA[R D1 > <![CDATA[R D2 > E14 D-1 Cl Cl <![CDATA[C8H 17 > <![CDATA[C8H 17 > E13 D-3 Cl Cl <![CDATA[C4H9]]> <![CDATA[C4H9]]> E17 D-4 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > E16 D-5 Br Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > E15 D-6 Br Br <![CDATA[C4H9]]> <![CDATA[C4H9]]> E18 D-X1 Cl Cl <![CDATA[C2H4CN]]> <![CDATA[C2H4CN]]> E19 D-X2 Br Br <![CDATA[C2H5]]> <![CDATA[C2H4CN]]> E20 D-X3 H H <![CDATA[C2H5]]> <![CDATA[C2H4CN]]> E35 D-13 H H <![CDATA[C6H 13 > <![CDATA[C6H 13 > E36 D-4 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 >

[1708] Table 25

[1709]

[1710] Dyeing Example Compound <![CDATA[R G > E21 G-1 <![CDATA[-CH(C6H 13 )C8H 17 > E22 G-X5 <![CDATA[C3H7]]> E37 G-1 <![CDATA[-CH(C6H 13 )C8H 17 >

[1711] For the dyed polyethylene fiber obtained in the dyeing example, the dyeing property evaluation, light fastness test, washing fastness test, perspiration fastness test, and rubbing fastness test were carried out in the same manner as for the dyed polypropylene fiber obtained in the above (dyeing of polypropylene fiber 1).

[1712] The evaluation results of the dyeing examples of the compound of formula (A) are shown in Table 26.

[1713] Table 26

[1714]

[1715] Regarding the dyeing property of the compound of formula (A), R used in dyeing examples E1, E2, and E26 to E28 A1 、R A2 and R A3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R A1 、R A2 and R A3 is an alkyl group having 4 to 14 carbon atoms) has good dyeing property. The disperse dyes used in dyeing example E3, which were previously used in dyeing polyester fibers, etc., namely R A1 、R A2 and R A3 all having alkyl groups with 3 or fewer carbon atoms, have poor dyeing property.

[1716] In addition, regarding the fastness of the compound of formula (A), R used in Dyeing Examples E1, E2, and E26 to E28 A1 , R A2 and R A3 are each independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of R A1 , R A2 and R A3 is an alkyl group having 4 to 14 carbon atoms) has good washing fastness, perspiration fastness, and rubbing fastness.

[1717] The evaluation results of the dyeing examples of the compound of formula (B) are shown in Table 27.

[1718]

[1719] Regarding the dyeability of the compound of formula (B), R used in Dyeing Examples E4 to E5 and E29 to E31 B1 , R B2 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms) has good dyeability. The dyeability of the disperse dye R B1 or R B2 which was previously used in dyeing polyester fibers and the like and is not an alkyl group having 1 to 14 carbon atoms is poor.

[1720] In addition, regarding the fastness of the compound of formula (B), R used in Dyeing Examples E4 to E5 and E29 to E31 B1 , R B2 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms) has substantially good light fastness, washing fastness, perspiration fastness, and rubbing fastness.

[1721] The evaluation results of the dyeing examples of the compound of formula (C) are shown in Table 28.

[1722]

[1723] Regarding the dyeability of the compound of formula (C), R used in Dyeing Examples E10 and E32 to E34 C1 , R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 , R C2 and RC3 (wherein at least one of them is an alkyl group having 4 to 14 carbon atoms) has good dyeing property. The disperse dye R that was previously used in dyeing polyester fibers and the like and was used in Dyeing Example E12 C1 、R C2 and R C3 (wherein at least one of them is an alkyl group having 3 or less carbon atoms) has poor dyeing property.

[1724] In addition, regarding each fastness of the compound of formula (C), R C1 、R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 、R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms) has substantially good light fastness, perspiration fastness and rubbing fastness.

[1725] In addition, regarding each fastness of the compound of formula (C), R used in Dyeing Examples E10 and E32 to E34 C1 、R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 、R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms) has good fastness.

[1726] The evaluation results of the dyeing examples of the compound of formula (D) are shown in Table 29.

[1727]

[1728] Regarding the dyeing property of the compound of formula (D), R used in Dyeing Examples E13 to E17 and E35, E36 D1 and R D2 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R D1 to R D2 is an alkyl group having 4 to 14 carbon atoms) has good dyeing property. However, in the case of the disperse dye that was previously used in dyeing polyester fibers and the like and was used in Dyeing Examples E18 to E20, for R D1 to R D2 the alkyl groups each have 1 to 3 carbon atoms, and its dyeing property is poor.

[1729] In addition, regarding each fastness of the compound of formula (D), the larger the carbon number of R D1 and R D2 , the better.

[1730] The evaluation results of the dyeing examples of the compound of formula (G) are shown in Table 30.

[1731] Table 30

[1732]

[1733] Regarding the dyeability of the compound of formula (G), the R used in Dyeing Examples E21 and E37 G being an alkyl group having 7 carbon atoms or 10 to 18 carbon atoms has good dyeability. The R which is a disperse dye conventionally used in dyeing polyester fibers etc. and used in Dyeing Example E22 G being an alkyl group having 3 carbon atoms has poor dyeability.

[1734] Regarding the fastnesses of the compound of formula (G), the R used in Dyeing Examples E21 and E37 G being an alkyl group having 7 carbon atoms or 10 to 18 carbon atoms is good.

[1735] (Exhaustion Dyeing of Polyethylene Fibers 2)

[1736] Using a dye composition in which two or more compounds described in Tables 3 to 9 are mixed, the polyethylene fibers were dyed in the same manner as in Dyeing Example E1. For the obtained dyed polyethylene fiber fabric, the dyeability evaluation, light fastness test, washing fastness test, perspiration fastness test, and rubbing fastness test were carried out in the same manner as for the obtained dyed polypropylene fiber fabric in the above (Exhaustion Dyeing of Polypropylene Fibers 2).

[1737] The evaluation results of the dyeing examples obtained using a dye composition in which two or more compounds described in Tables 3 to 9 are mixed are shown in Table 31.

[1738] Table 31

[1739]

[1740] As shown in Table 31, when the orange dye, red dye, and blue dye obtained in the present invention are mixed and used, a black dyed fabric with good dyeability and generally good fastnesses is obtained.

[1741] (Printing and Dyeing of Polypropylene Fibers 1)

[1742] The polypropylene fibers were dyed by the printing method using only one of the dye compositions of the compounds described in Tables 3 to 9 or the dye compositions of disperse dye compounds etc. conventionally used in dyeing polyester fibers etc. shown in Tables 3 to 9.

[1743] (Dyeing Example PP1)

[1744] 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 homogeneous to obtain paste A. To the above paste A was added a dye dispersion obtained by adding 18.5 g of water to 1.5 g of the dye composition of blue compound A-13 obtained in Dye Composition Production Example 76 (dye concentration: 20% by mass) and stirring, and stirred until homogeneous to prepare a printing paste (0.3% o.m.p.). The above printing paste was printed on polypropylene fibers, dried by dry heat at 110°C for 3 minutes, developed at 130°C for 6 minutes using an H.T. steam generator, and then subjected to reduction washing, water washing, and drying to obtain a blue polypropylene fiber dyed product.

[1745] (Dyeing Examples PP2 to PP12)

[1746] Except that the dye composition of blue compound A-13 described in Dyeing Example PP1 was changed to the dye compositions of the compounds in Tables 32 to 36, a dyed polypropylene fiber dyed product was obtained by the same dyeing procedure as in Dyeing Example PP1.

[1747] (Dyeing Example PP13)

[1748] 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 homogeneous to obtain paste A. To the above paste A was added a dye dispersion obtained by adding 18.5 g of water to 1.5 g of the powdery dye composition of blue compound A-5 obtained in Dye Composition Production Example 107 (dye concentration: 20% by mass) and stirring, and stirred until homogeneous to prepare a printing paste (0.3% o.m.p.). The above printing paste was printed on polypropylene fibers, dried by dry heat at 110°C for 3 minutes, developed at 130°C for 6 minutes using an H.T. steam generator, and then subjected to reduction washing, water washing, and drying to obtain a blue polypropylene fiber dyed product.

[1749] (Dyeing Examples PP14 to PP19)

[1750] Except that the powdery dye composition of blue compound A-5 described in Dyeing Example PP13 was changed to the powdery dye compositions of the compounds in Tables 32 to 36, a dyed polypropylene fiber dyed product was obtained by the same dyeing procedure as in Dyeing Example PP13.

[1751] Table 32

[1752]

[1753]

[1754] Table 33

[1755]

[1756] Dyeing Example Compound <![CDATA[R B1 > <![CDATA[R B2 > <![CDATA[R B3 > PP4 B-3 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> PP5 B-2 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C4H9]]> PP6 B-10 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[-CH(C2H5)C4H9]]> PP14 B-2 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C4H9]]>

[1757] Table 34

[1758]

[1759] Dyeing Example Compound <![CDATA[X C > <![CDATA[Y C > <![CDATA[R C1 > <![CDATA[R C2 > <![CDATA[R C3 > PP7 C-4 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3 <!-- 127 -->]]> PP8 C-3 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> PP9 C-20 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> PP15 C-4 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> PP16 C-20 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]>

[1760] Table 35

[1761]

[1762] Dyeing Example Compound <![CDATA[X D > <![CDATA[Y D > <![CDATA[R D1 > <![CDATA[R D2 > PP10 D-13 H H <![CDATA[C6H 13 > <![CDATA[C6H 13 > PP11 D-4 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > PP17 D-4 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > PP18 D-5 Br Br <![CDATA[C8H 17 > <![CDATA[C8H 17 >

[1763] Table 36

[1764]

[1765] Dyeing Example Compound <![CDATA[R G > PP12 G-1 <![CDATA[-CH(C6H 13 )C8H 17 > PP19 G-1 <![CDATA[-CH(C6H 13 )C8H 17 >

[1766] The polypropylene fiber dyed product obtained in the dyeing example was subjected to dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration fastness test, rubbing fastness test and fastness test to hot pressing in the same manner as the polypropylene fiber dyed product obtained in the above-mentioned (Dyeing 1 of polypropylene fiber).

[1767] Table 37 shows the evaluation results of the dyeing examples of the compound of formula (A).

[1768] Table 37

[1769]

[1770] Regarding the dyeing properties of the compound of formula (A), R used in dyeing examples PP1 to PP3 and PP13 A1 , R A2 and R A3 are independently an alkyl group having 1 to 14 carbon atoms (wherein R A1 , R A2 and R A3 The compound in which at least one of the groups is an alkyl group having 4 to 14 carbon atoms has good dyeing properties.

[1771] In addition, regarding the fastness of the compound of formula (A), R A1 , R A2 and R A3 are independently an alkyl group having 1 to 14 carbon atoms (wherein R A1 , RA2 and R A3 The sublimation fastness, washing fastness, perspiration fastness, rubbing fastness and fastness to heat pressing of the compound (wherein at least one of R

[1772] The evaluation results of the dyeing examples of the compound of formula (B) are shown in Table 38.

[1773] Table 38

[1774]

[1775] Regarding the dyeability of the compound of formula (B), R used in dyeing examples PP4 to PP5 and PP14 B1 , R B2 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms) has good dyeability.

[1776] Furthermore, regarding each fastness of the compound of formula (B), R used in dyeing examples PP4 to PP5 B1 , R B2 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R B1 , R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms) has good fastness in each aspect.

[1777] The evaluation results of the dyeing examples of the compound of formula (C) are shown in Table 39.

[1778] Table 39

[1779]

[1780] Regarding the dyeability of the compound of formula (C), R used in dyeing examples PP7 to PP9, PP15 and PP16 C1 , R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 , R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms) has good dyeability.

[1781] Furthermore, regarding each fastness of the compound of formula (C), R used in dyeing examples PP7 to PP9, PP15 and PP16 C1 , R C2 and RC3 Each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 , R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms), and the fastness of each compound is good.

[1782] The evaluation results of the dyeing examples of the compound of formula (D) are shown in Table 40.

[1783] Table 40

[1784]

[1785] Regarding the dyeability of the compound of formula (D), R used in dyeing examples PP10, PP11, PP17 and PP18 D1 and R D2 Each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R D1 and R D2 is an alkyl group having 4 to 14 carbon atoms), and the dyeability of the compound is good.

[1786] Furthermore, regarding the fastness of each of the compounds of formula (D), R used in dyeing examples PP10, PP11, PP17 and PP18 D1 and R D2 Each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R D1 and R D2 is an alkyl group having 4 to 14 carbon atoms), and the fastness of each compound is good.

[1787] The evaluation results of the dyeing examples of the compound of formula (G) are shown in Table 41.

[1788] Table 41

[1789]

[1790] Regarding the dyeability of the compound of formula (G), R used in dyeing examples PP12 and PP19 G is an alkyl group having 7 or 10 to 18 carbon atoms, and the dyeability of the compound is good.

[1791] Regarding the fastness of each of the compounds of formula (G), R used in dyeing examples PP12 and PP19 G is an alkyl group having 7 or 10 to 18 carbon atoms, and the fastness is good.

[1792] (Printing and dyeing of polypropylene fibers 2)

[1793] Using a dye composition that mixes two or more compounds described in Tables 3 to 9, polypropylene fibers were dyed using a printing paste of 1.2% o.m.p. according to Dyeing Example PP1.

[1794] Furthermore, using a dye composition that mixes two or more compounds described in Tables 3 to 9, polypropylene fibers were dyed using a printing paste of 1.8% o.m.p. according to Dyeing Example PP13.

[1795] For the obtained polypropylene fiber dyed fabrics, the same dyeing property evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration fastness test, rubbing fastness test, and fastness test against hot pressing were carried out as those of the polypropylene fiber dyed fabrics obtained in the above (Dyeing of Polypropylene Fibers 2).

[1796] The results are shown in Table 42.

[1797] Table 42

[1798]

[1799] As shown in Table 42, when the orange dye, red dye, and blue dye obtained in the present invention are mixed and used, a black dyed fabric with good dyeing property and good fastnesses is obtained.

[1800] (Printing of Polyethylene Fibers 1)

[1801] Only one kind of the dye composition of the compounds described in Tables 3 to 9 or the dye composition such as the disperse dye compound previously used in the dyeing of polyester fibers and the like shown in Tables 3 to 9 was used to dye polyethylene fibers by the printing method.

[1802] (Dyeing Example EP1)

[1803] 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 homogeneous to obtain Paste A. A dye dispersion obtained by adding 1.5 g of the dye composition of the blue compound A-13 obtained in Dye Composition Production Example 76 (dye concentration 20% by mass) and adding 18.5 g of water and stirring was added to the above Paste A, and stirred until homogeneous to prepare a printing paste (0.3% o.m.p.). The above printing paste was printed on polyethylene fibers, dried by hot air at 110°C for 3 minutes, developed at 110°C for 6 minutes by an H.T. steam generator, and then subjected to reduction washing, water washing, and drying to obtain a blue polyethylene fiber dyed fabric.

[1804] (Dyeing Examples EP2 to EP12)

[1805] Except for changing the dye composition of the blue compound A-13 described in Dyeing Example EP1 to the dye compositions of the compounds in Tables 43 to 47, a dyed polyethylene fiber fabric was obtained by the same dyeing procedure as in Dyeing Example EP1.

[1806] (Dyeing Example EP13)

[1807] 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 the mixture was stirred until homogeneous to obtain Paste A. A dye dispersion obtained by adding 1.5 g of the powdery dye composition of the blue compound A-5 (dye concentration: 20% by mass) obtained in Dye Composition Production Example 105 and 18.5 g of water and stirring was added to the above Paste A, and the mixture was stirred until homogeneous to prepare a printing paste (0.3% o.m.p.). The above printing paste was printed on polyethylene fibers, dried by hot air at 110°C for 3 minutes, developed at 110°C for 6 minutes using an H.T. steam generator, and then subjected to reduction washing, water washing, and drying to obtain a blue polyethylene fiber fabric.

[1808] (Dyeing Examples EP14 to EP19)

[1809] Except for changing the powdery dye composition of the blue compound A-5 described in Dyeing Example EP13 to the powdery dye compositions of the compounds in Tables 44 to 47, a dyed polyethylene fiber fabric was obtained by the same dyeing procedure as in Dyeing Example EP13.

[1810] Table 43

[1811]

[1812] Dyeing Example Compound <![CDATA[X A > <![CDATA[Y A > <![CDATA[R A1 > <![CDATA[R A2 > <![CDATA[R A3 > <![CDATA[R A4 > EP1 A-13 <![CDATA[NO2]]> Br <![CDATA[C6H 13 > <![CDATA[C6H 13 > <![CDATA[CH3]]> <![CDATA[CH3]]> EP2 A-3 <![CDATA[NO2]]> Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> <![CDATA[CH3]]> EP3 A-2 <![CDATA[NO2]]> Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C4H9]]> <![CDATA[CH3]]> EP13 A-5 <![CDATA[NO2]]> Br <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> <![CDATA[CH3]]>

[1813] Table 44

[1814]

[1815] Dyeing Example Compound <![CDATA[R B1 > <![CDATA[R B2 > <![CDATA[R B3 > EP4 B-3 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> EP5 B-2 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C4H9]]> EP6 B-10 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[-CH(C2H5)C4H9 <!-- 135 -->]]> EP14 B-2 <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C4H9]]>

[1816] Table 45

[1817]

[1818] Dyeing Example Compound <![CDATA[X C > <![CDATA[Y C > <![CDATA[R C1 > <![CDATA[R C2 > <![CDATA[R C3 > EP7 C-4 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> EP8 C-3 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[C2H5]]> EP9 C-20 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> EP15 C-4 Cl H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]> EP16 C-20 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > <![CDATA[CH3]]>

[1819] Table 46

[1820]

[1821] Dyeing Example Compound <![CDATA[X D > <![CDATA[Y D > <![CDATA[R D1 > <![CDATA[R D2 > EP10 D-13 H H <![CDATA[C6H 13 > <![CDATA[C6H 13 > EP11 D-4 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > EP17 D-4 H H <![CDATA[C8H 17 > <![CDATA[C8H 17 > EP18 D-5 Br Br <![CDATA[C8H 17 > <![CDATA[C8H 17 >

[1822] Table 47

[1823]

[1824] Dyeing Example Compound <![CDATA[R G > EP12 G-1 <![CDATA[-CH(C6H 13 )C8H 17 > EP19 G-1 <![CDATA[-CH(C6H 13 )C8H 17 >

[1825] For the dyed polyethylene fiber obtained in the dyeing example, the dyeing property evaluation, light fastness test, wash fastness test, perspiration fastness test, and rubbing fastness test were carried out in the same manner as for the dyed polypropylene fiber obtained in the above (pad dyeing 1 of polypropylene fiber).

[1826] The evaluation results of the dyeing examples of the compound of formula (A) are shown in Table 48.

[1827] Table 48

[1828]

[1829] Regarding the dyeing property of the compound of formula (A), R used in dyeing examples EP1 to EP3 and EP13 A1 , R A2 and R A3 are each independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of R A1 , R A2 and R A3 is an alkyl group having 4 to 14 carbon atoms) and the compound has good dyeing property.

[1830] In addition, regarding each fastness of the compound of formula (A), R used in dyeing examples EP1 to EP3 and EP13 A1 , R A2 and R A3 are each independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of R A1 , R A2 and R A3 is an alkyl group having 4 to 14 carbon atoms) and the compound has good wash fastness, perspiration fastness, and rubbing fastness.

[1831] The evaluation results of the dyeing examples of the compound of formula (B) are shown in Table 49.

[1832] Table 49

[1833]

[1834] Regarding the dyeing property of the compound of formula (B), R used in dyeing examples EP4 to EP5 and EP14 B1 , R B2 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein R B1 , R B2 and RB3 Compounds in which at least one of them is an alkyl group having 4 to 14 carbon atoms have good dyeability.

[1835] In addition, regarding each fastness of the compound of formula (B), R used in Dyeing Examples EP4 to EP5 and EP14 B1 、R B2 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R B1 、R B2 and R B3 is an alkyl group having 4 to 14 carbon atoms) have good fastness in each case.

[1836] The evaluation results of the dyeing examples of the compound of formula (C) are shown in Table 50.

[1837] Table 50

[1838]

[1839] Regarding the dyeability of the compound of formula (C), R used in Dyeing Examples EP7 to EP9, EP15 and EP16 C1 、R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 、R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms) have good dyeability.

[1840] In addition, regarding each fastness of the compound of formula (C), R used in Dyeing Examples EP7 to EP9, EP15 and EP16 C1 、R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R C1 、R C2 and R C3 is an alkyl group having 4 to 14 carbon atoms) have good fastness in each case.

[1841] The evaluation results of the dyeing examples of the compound of formula (D) are shown in Table 51.

[1842] Table 51

[1843]

[1844] Regarding the dyeability of the compound of formula (D), R used in Dyeing Examples EP10, EP11, EP17 and EP18 D1 、R D2 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein, RD1 and R D2 in which at least one of them is an alkyl group having 4 to 14 carbon atoms) has good dyeability.

[1845] In addition, regarding each fastness of the compound of formula (D), R used in dyeing examples EP10, EP11, EP17 and EP18 D1 and R D2 each independently represents an alkyl group having 1 to 14 carbon atoms (wherein at least one of R D1 and R D2 is an alkyl group having 4 to 14 carbon atoms) has good fastness.

[1846] The evaluation results of the dyeing examples of the compound of formula (G) are shown in Table 52.

[1847] Table 52

[1848]

[1849] Regarding the dyeability of the compound of formula (G), R used in dyeing examples EP12 and EP19 G is an alkyl group having 7 or 10 to 18 carbon atoms, and the dyeability of the compound is good.

[1850] Regarding each fastness of the compound of formula (G), R used in dyeing examples EP12 and EP19 G is an alkyl group having 7 or 10 to 18 carbon atoms, and the fastness is good.

[1851] (Printing and dyeing of polyethylene fibers 2)

[1852] Using a dye composition in which two or more compounds described in Tables 3 to 9 are mixed, polyethylene fibers were dyed using a printing paste of 1.2% o.m.p. according to dyeing example EP1.

[1853] Furthermore, using a dye composition in which two or more compounds described in Tables 3 to 9 are mixed, polyethylene fibers were dyed using a printing paste of 1.8% o.m.p. according to dyeing example EP13.

[1854] For the obtained polyethylene fiber dyed products, the dyeability evaluation, light fastness test, washing fastness test, perspiration fastness test and rubbing fastness test were carried out in the same manner as the polypropylene fiber dyed products obtained in the above (Dyeing of polypropylene fibers 2).

[1855] The results are shown in Table 53.

[1856] Table 53

[1857]

[1858] As shown in Table 53, when the orange dye, red dye and blue dye obtained in the present invention are used in combination, a black dyed fabric with good dyeability and good fastness properties is obtained.

[1859] In summary, the present invention is not limited to the above-described embodiments, and embodiments obtained by appropriately combining the components of the embodiments or by substitution are also included in the present invention.

[1860] In addition, based on the knowledge of those skilled in the art, the combinations or the order of steps in the embodiments can be appropriately reorganized, or various design changes can be made to the embodiments, and the embodiments subjected to such modifications are also included in the scope of the present invention.

[1861] Industrial Applicability

[1862] The present invention can be used to dye polyolefin fibers used in clothing items such as clothes, underwear, hats, socks, gloves, sportswear, interior materials for vehicles such as seat covers, carpets, curtains, floor mats, sofa covers, cushion covers, and other interior decoration items.

Claims

1. A dye composition comprising at least one of the compounds of the following general formulas (A) to (G) and a nonionic dispersant, The nonionic dispersant is a polyoxyethylene aryl aryl ether and an ethylene oxide - propylene oxide copolymer, In formula (A), X A is nitro, Y A represents a halogen atom, R A1 , R A2 and R A3 Each independently represents an alkyl group having 1 to 14 carbon atoms, wherein R A1 、R A2 and R A3 at least one of which is an alkyl group having 4 to 14 carbon atoms R A4 represents an alkyl group having 1 to 4 carbon atoms; In formula (B), R B1 , R B2 , and R B3 each independently represent an alkyl group having 1 to 14 carbon atoms, wherein at least one of R B1 , R B2 , and R B3 is an alkyl group having 4 to 14 carbon atoms; In formula (C), X C and Y C 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, or a hydrogen atom and a hydrogen atom. R C1 、R C2 and R C3 each independently represents an alkyl group having 1 to 14 carbon atoms, wherein 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 represents 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 obtained by substitution with CN, wherein R D1 and R D2 at least one of which is an alkyl group having 4 to 14 carbon atoms; In formula (E), X E and Y E each independently represents 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 represents an alkyl group having 4 to 14 carbon atoms; In formula (G), R G represents an alkyl group having 7 carbon atoms or 10 to 18 carbon atoms.

2. The dye composition according to claim 1, wherein, The polyoxyethylene aryl aryl ether is a polyoxyethylene aryl phenyl ether.

3. The dye composition according to claim 2, wherein, The ethylene oxide - propylene oxide copolymer has 300 moles of ethylene oxide and 55 moles of propylene oxide.

4. The dye composition according to claim 2, which is a dye composition for dyeing black and contains at least three of the compounds of general formulas (A) to (G).

5. The dye composition according to claim 4, which is a dye composition for dyeing black and contains at least three of the compounds of general formulas (A) to (D) and (G).

6. The dye composition according to claim 4, wherein The dye composition for dyeing black contains: A blue compound composed of the compound of general formula (A), A blue compound composed of the compound of general formula (B), and An orange compound composed of the compound of general formula (D).

7. The dye composition according to claim 6, wherein, The dye composition for dyeing black contains the following compounds:

8. The dye composition according to claim 4, wherein The dye composition for dyeing black contains: 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 the compound of general formula (C) and the compound of general formula (D); And 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).

9. The dye composition according to claim 5, wherein The dye composition for dyeing black contains: 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 (C); At least one red compound selected from the group consisting of the compound of general formula (C) and the compound of general formula (D); And At least one yellow or orange compound selected from the group consisting of the compound of general formula (D) and the compound of general formula (G).

10. The dye composition according to claim 8, wherein, The dye composition for dyeing black contains: 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); The red compound of the compound of general formula (C); And At least one orange compound selected from the group consisting of the compound of general formula (D) and the compound of general formula (E).

11. The dye composition according to claim 8, wherein, The dye composition for dyeing black contains: The blue compound of the compound of general formula (A), the red compound of the compound of general formula (C), and the orange compound of the compound of general formula (D).

12. The dye composition according to claim 8, wherein, Regarding the content of the compounds in the dye composition for dyeing black, Relative to the total of the purple or blue compound, the red compound, and the 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 ratio of the yellow or orange compound ranges from 15 to 55% by mass.

13. The dye compound according to claim 8, wherein Regarding the content of the compound in the dye composition for dyeing black, Relative to the total of the purple or blue compound, the red compound, and the 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 ratio of the yellow or orange compound ranges from 25 to 45% by mass.

14. The dye composition according to claim 1, which is a dye composition for dyeing polyolefin fibers.

15. The dye composition according to claim 1, which is a dye composition used in aqueous dyeing.

16. The dye composition according to claim 1, wherein The dye composition is in powder form.

17. The dye composition according to claim 16, wherein The powder-form dye composition is manufactured by spray drying treatment.

18. A method, which is a method for dyeing fibers, The method includes a step of subjecting the fibers to aqueous dyeing using the dye composition according to any one of claims 1 to 17.

19. The dyeing method according to claim 18, wherein, The dyeing step is at least one selected from the group consisting of dipping, printing, and inkjet dyeing.

20. The dyeing method according to claim 19, wherein, The printing is transfer dyeing.

21. The dyeing method according to claim 18, wherein The dyeing step is at least one selected from dipping and printing.

22. The dyeing method according to claim 18, wherein The dyeing step is printing.

23. The dyeing method according to claim 18, wherein, The fiber is polyolefin, The dyeing step is carried out at 80°C to 130°C.

24. The dyeing method according to claim 18, wherein The fiber is polypropylene, The dyeing step is carried out at 110°C to 130°C.

25. The dyeing method according to claim 18, wherein, The fiber is polyethylene, The dyeing step is carried out at 90°C to 110°C.

26. The dyeing method according to claim 18, wherein The dyeing method is printing, and the concentration of the dye contained in the dye composition relative to the printing paste is in the range of 0.001% o.m.p. to 5% o.m.p., where o.m.p. means on the mass of paste, based on the mass of the paste.

27. The dyeing method according to claim 18, wherein The dyeing method is dipping, The concentration of the dye contained in the dye composition relative to the fiber is in the range of 0.001% o.m.f. to 10% o.m.f., where o.m.f. means on the mass of fiber, based on the mass of the fiber.

28. A fiber dyed by the dyeing method according to any one of claims 18 to 27.

29. The following general formula (F) compound, In formula (F), R F1 and R F2 each independently represents an alkyl group having 4 to 14 carbon atoms.

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