Dye for dyeing using supercritical carbon dioxide

Abstract

The present invention addresses the problem of providing: a dye for dyeing fibers using supercritical carbon dioxide, said dye being capable of dyeing fibers to a yellow color at a high concentration and having excellent dyeing fastness such as light resistance, sublimation, and washing of a dyed product; and a method for dyeing fibers using supercritical carbon dioxide. And a fiber and a compound dyed by the dyeing method. Provided are: a dye for dyeing a fiber using supercritical carbon dioxide, which contains a compound represented by formula (I); a method for dyeing a fiber using supercritical carbon dioxide; a fiber dyed by the dyeing method; and a compound. In formula (I), R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a dye for dyeing fibers using supercritical carbon dioxide, a method for dyeing fibers using supercritical carbon dioxide, fibers dyed by the above dyeing method, and compounds. 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, high antistatic property, and renewable.

[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. Due to reasons such as low affinity and compatibility with conventional dye compounds, and in addition, the absence of functional groups effective for chemical reactions, high-concentration and high-fastness dyeing is considered extremely difficult.

[0004] Therefore, among the colored polyolefin resins on the market at present, most of them are resins in which colored pigments are added at the manufacturing stage of polymer pellets or the like, and then spun, molded, etc. to form a desired shape.

[0005] In this coloring method, it is necessary to determine the color at the initial stage of the resin product manufacturing process. In addition, if cost accounting is considered, 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, problems such as the generation of a large amount of waste resin, and the waste of time and energy occur.

[0007] As described in Yoh Yamamoto, Journal of the Fiber Society, 61(2005), 319 - 321, polypropylene resin and polyethylene resin are the four major general-purpose synthetic resins along with polyvinyl chloride resin and polystyrene resin, and are used in a wide range of fields.

[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, and in the only effective coloring method, i.e., the masterbatch coloring method using colored pigments, the monofilament fineness has to be increased, and in addition, the freedom of color selection is restricted, etc.

[0010] Heretofore, in order to perform aqueous dyeing of polyolefin-based resin fibers, attempts have been made to change the molecular structure of dyes, and dyes for dyeing polyolefin-based resin fibers have been proposed in Japanese Patent Publication No. 38-10741, Japanese Patent Publication No. 40-1277, Japanese Patent Publication No. 41-3515, British Patent No. 872,882, U.S. Patent No. 3,536,735, and Japanese Unexamined Patent Application Publication No. 2019-203223.

[0011] In Japanese Patent Publication No. 38-10741, 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, these anthraquinone-based red dyes or anthraquinone-based purple dyes are difficult to perform high-concentration dyeing of polyolefin-based resin fibers. Furthermore, regarding the form of the dye used for dyeing, there are descriptions such as dissolving these anthraquinone-based red dyes in an alcohol or acetone as an organic solvent and then using them, and it is hardly environmentally friendly. In addition, there is no description of yellow dyes.

[0013] Japanese Patent Publication No. 40-1277 describes 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.

[0014] However, these anthraquinone-based blue dyes are difficult to perform high-concentration dyeing of polyolefin-based resin fibers, and there is no specific description regarding the dye fastness of the obtained dyed products. Furthermore, regarding the form of the dye used during dyeing, there are descriptions such as dissolving these anthraquinone-based blue dyes in an alcohol or acetone as an organic solvent and then using them, and it is hardly environmentally friendly. In addition, there is no description of yellow dyes.

[0015] Japanese Patent Publication No. 41-3515 describes 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.

[0016] However, these anthraquinone-based blue dyes are difficult to perform high-concentration dyeing of polyolefin-based resin fibers, and there is no specific description regarding the dye fastness of the obtained dyed products. Furthermore, regarding the form of the dye used during dyeing, there are descriptions such as dissolving them in an alcohol or acetone as an organic solvent and then using them, and it is difficult to say that they are environmentally friendly. In addition, there is no description of yellow dyes.

[0017] The British Patent Specification No. 872,882 describes an example of dyeing polyolefin resin fibers with a blue dye obtained by introducing an alkylamino or cycloalkylamino group at the α-position of an anthraquinone-based dye.

[0018] However, it is difficult to highly concentrate dye polyolefin resin fibers with these anthraquinone-based blue dyes. In addition, there is no specific description of the dye fastness of the obtained dyed products. Moreover, there is no description of yellow dyes.

[0019] The U.S. Patent Specification No. 3,536,735 describes an example of manufacturing a red dye obtained by introducing a phenoxy group having two substituents selected from sec-butyl, sec-pentyl, and tert-pentyl into an anthraquinone-based dye and an example of dyeing polypropylene resin fibers using them.

[0020] However, it is difficult to highly concentrate dye polyolefin resin fibers with these anthraquinone-based red dyes. In addition, there is no specific description of the dye fastness of the obtained dyed products. Furthermore, regarding the form of the dye when used in dyeing, there are descriptions such as using it after dissolving in dimethylformamide as an organic solvent, and it is difficult to say that they are environmentally friendly. Moreover, there is no description of yellow dyes.

[0021] Japanese Patent Laid-Open No. 2019-203223 describes an example of dyeing polypropylene fibers in water using a disperse dye composition containing an anthraquinone-based yellow dye, anthraquinone-based red dye, or anthraquinone-based blue dye having a long-chain alkyl group.

[0022] However, it is difficult to highly concentrate dye polypropylene fibers with the described anthraquinone-based yellow dye having a long-chain alkyl group.

[0023] Japanese Patent Laid-Open No. 55-152869 describes an example of manufacturing a monoazo-based dye having a long-chain alkyl group and an example of dyeing fine terylene polyester fibers using them. However, there is no description of an example of dyeing polyolefin fibers using them. Moreover, there is no description of yellow dyes.

[0024] In addition, various studies have been conducted on the modification of polyolefin resin fibers in order to improve their dyeability.

[0025] 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.

[0026] Although the dyeability of these modified polyolefin resin fibers has been improved, the strength of the yarn decreases due to the dyeing treatment, and there is a problem of insufficient strength when used for clothes and the like.

[0027] Furthermore, in Japanese Patent Publication No. 3253649, as a dyeing method in place of aqueous dyeing, it is described that supercritical carbon dioxide is used as a dyeing medium, and various dyes are used to dye hydrophobic fiber materials, etc.

[0028] However, as an example of a hydrophobic fiber material, polypropylene is described, but in the examples, only a dyeing example of polyester cloth is described, and no dyeing example of polypropylene fiber is described.

[0029] In Japanese Patent Publication No. 6721172, it is described that supercritical carbon dioxide is used as a dyeing medium, and polypropylene fiber, which is a polyolefin fiber, is dyed with an anthraquinone-based blue dye, an anthraquinone-based yellow dye, an anthraquinone-based red dye, and a mixture of these dyes.

[0030] However, the described anthraquinone-based yellow dye is difficult to perform high-concentration dyeing of polypropylene fiber.

[0031] If a method for high-concentration and high-fastness dyeing of polypropylene resin fiber and polyethylene resin fiber is put into practical use, it will be possible to color inexpensive ordinary yarns with small monofilament fineness without color number limitation, and new uses are expected to be developed in fields such as clothing and vehicle interior decoration materials where polypropylene resin fiber and polyethylene resin fiber have not been applied so far and high designability is required. Summary of the Invention

[0032] The present invention relates to a dye for dyeing fibers using supercritical carbon dioxide, which contains a compound represented by the following general formula (I).

[0033] [Chemical Formula 1]

[0034]

[0035] [In formula (I),

[0036] R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms,

[0037] R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.] Brief Description of the Drawings

[0038] Figure 1 It shows a supercritical carbon dioxide dyeing apparatus used in dyeing. Detailed Description of the Invention

[0039] Accordingly, an object of the present invention is to provide a dye for dyeing fibers with supercritical carbon dioxide, which can dye fibers into a high-concentration yellow color and has excellent color fastness such as light fastness, sublimation fastness, and washing fastness of the dyed product, a method for dyeing fibers using supercritical carbon dioxide, fibers dyed by the above dyeing method, and a compound.

[0040] The present invention relates to a dye for dyeing fibers with supercritical carbon dioxide, which contains a compound represented by the following general formula (I).

[0041] [Chemical formula 2]

[0042]

[0043] [In formula (I),

[0044] R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms,

[0045] and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.]

[0046] In addition, the present invention provides a method for dyeing fibers using supercritical carbon dioxide, which includes a step of dyeing fibers in the presence of supercritical carbon dioxide using the above dye of the present invention.

[0047] In addition, the present invention provides a fiber dyed by a dyeing method including a step of dyeing fibers in the presence of supercritical carbon dioxide using the above dye of the present invention.

[0048] In addition, the present invention provides a compound represented by the following general formula (I).

[0049] [Chemical formula 3]

[0050]

[0051] [In formula (I),

[0052] R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms,

[0053] and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.]

[0054] The dye of the present invention can dye fibers into a high-concentration yellow color in the presence of supercritical carbon dioxide, and the dyed product has excellent color fastness such as light fastness, sublimation fastness, and washing fastness.

[0055] The inventors of the present invention have found that dyes containing the following specific compounds have improved affinity for fibers and can dye the fibers into a high-concentration yellow in the presence of supercritical carbon dioxide, thus completing the present invention.

[0056] <Compound of formula (I)>

[0057] The compound of general formula (I) contained in the dye of the present invention is as described below.

[0058] [Chemical formula 4]

[0059]

[0060] [In formula (I),

[0061] R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms,

[0062] R3, R4, R5 and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.]

[0063] In the above formula (I), examples of the alkyl group having 4 to 14 carbon atoms include 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, 1-ethyl-1-methylpropyl, n-octyl, 2-ethylhexyl, n-decyl, n-dodecyl, and n-tetradecyl. Among them, as the alkyl group having 4 to 14 carbon atoms, an alkyl group having 4 to 12 carbon atoms is preferred, an alkyl group having 4 to 10 carbon atoms is preferred, and an alkyl group having 4 to 8 carbon atoms is more preferred.

[0064] In the above formula (I), examples of the aralkyl group having 7 to 12 carbon atoms include benzyl, phenethyl, 1-naphthylmethyl, and 2-naphthylmethyl. Among them, an aralkyl group having 7 to 10 carbon atoms is preferred, an aralkyl group having 7 to 9 carbon atoms is preferred, and an aralkyl group having 7 carbon atoms is more preferred.

[0065] In the above formula (I), examples of the aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms include 4-methylbenzyl, 4-methylphenethyl, 4-ethylbenzyl, 4-ethylphenethyl, 4-n-propylbenzyl, 4-n-propylphenethyl, 4-n-butylbenzyl, 4-n-butylphenethyl, 4-isopropylbenzyl, 4-tert-butylbenzyl, and 4-tert-butylphenethyl. Among them, an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms is preferred, an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms is preferred, and an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms is more preferred.

[0066] In the above formula (I), 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 methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl. As the alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 3 carbon atoms is preferred, an alkyl group having 1 or 2 carbon atoms is preferred, and an alkyl group having 1 carbon atom is more preferred.

[0067] In addition, the present invention provides a compound of formula (I).

[0068] [Chemical formula 5]

[0069]

[0070] [In formula (I),

[0071] R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms,

[0072] R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.]

[0073] In the above formula (I), R1 and R2 each independently are preferably: a branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably: a branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably: a branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0074] In addition, in the above formula (I), R1 and R2 are each independently preferably: a branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably: a branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably: a branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably: a branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0075] In addition, in the above formula (I), R1 and R2 are each independently preferably: a branched alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably: a branched alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably: a branched alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, more preferably: a branched alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0076] In addition, in the above formula (I), R1 and R2 are each independently preferably: a branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably: a branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably: a branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, further preferably: a branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0077] In addition, in the above formula (I), R3, R4, R5 and R6 are each independently preferably a hydrogen atom or a branched alkyl group having 1 to 4 carbon atoms.

[0078] In addition, in the above formula (I), R3, R4, R5 and R6 are each independently more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0079] In addition, in the above formula (I), R3, R4, R5 and R6 are each independently more preferably a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0080] In addition, in the above formula (I), R3, R4, R5, and R6 are each independently further preferably a hydrogen atom or an alkyl group having 1 carbon atom.

[0081] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0082] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms.

[0083] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0084] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0085] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0086] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0087] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0088] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0089] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0090] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0091] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0092] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0093] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0094] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0095] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0096] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0097] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0098] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0099] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0100] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0101] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0102] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0103] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0104] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0105] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0106] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0107] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0108] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0109] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0110] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0111] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0112] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0113] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0114] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0115] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0116] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0117] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0118] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0119] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0120] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0121] In addition, in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0122] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0123] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0124] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0125] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 carbon atom.

[0126] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0127] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0128] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0129] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0130] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0131] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 carbon atom.

[0132] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0133] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0134] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0135] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0136] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0137] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 carbon atom.

[0138] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0139] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0140] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0141] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0142] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0143] In addition, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 carbon atom.

[0144] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0145] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0146] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0147] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0148] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0149] Further, in the above formula (I), it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0150] Further, in the above formula (I), it is preferred that: R1 and R2 each independently represent an alkyl group having 4 to 6 carbon atoms, R3, R4, and R6 represent hydrogen atoms, and R5 is an alkyl group having 1 to 4 carbon atoms.

[0151] The compound of formula (I) preferably includes the following compounds, and more preferably the compounds of formula (1) and (2).

[0152] [Chemical formula 6]

[0153]

[0154] The compound of the above formula (I) is a yellow dye compound.

[0155] In the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently preferably a branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, more preferably: a branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, still more preferably: a branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0156] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently preferably a branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, more preferably: a branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, still more preferably: a branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, most preferably: a branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0157] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently preferably a branched alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, more preferably: a branched alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, still more preferably: a branched alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, still more preferably: a branched alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0158] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently preferably a branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, more preferably: a branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, still more preferably: a branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and even more preferably: a branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0159] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R3, R4, R5 and R6 are each independently preferably a hydrogen atom or a branched alkyl group having 1 to 4 carbon atoms.

[0160] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R3, R4, R5 and R6 are each independently more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0161] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R3, R4, R5 and R6 are each independently still more preferably a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0162] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R3, R4, R5 and R6 are each independently even more preferably a hydrogen atom or an alkyl group having 1 carbon atom.

[0163] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently even more preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0164] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently even more preferably an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0165] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently even more preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0166] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0167] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0168] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0169] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0170] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0171] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0172] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0173] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0174] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0175] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0176] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0177] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0178] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0179] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0180] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0181] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0182] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0183] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0184] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0185] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0186] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0187] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0188] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0189] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0190] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0191] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0192] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0193] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0194] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0195] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0196] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0197] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0198] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0199] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0200] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0201] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

[0202] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., in formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

[0203] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., in the above formula (I), R1 and R2 are each independently further preferably an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0204] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently further preferably an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5 and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0205] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5 and R6 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0206] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., more preferably, R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0207] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., more preferably, R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 carbon atom.

[0208] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., more preferably, R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0209] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., more preferably, R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0210] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., more preferably, R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0211] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., more preferably, R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0212] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0213] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 carbon atom.

[0214] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0215] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0216] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0217] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0218] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0219] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 carbon atom.

[0220] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0221] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0222] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0223] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0224] Further, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5 and R6 each independently are a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0225] Further, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5 and R6 each independently are a hydrogen atom or an alkyl group having 1 carbon atom.

[0226] Further, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms, and R3, R4, R5 and R6 each independently are a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0227] Further, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, and R3, R4, R5 and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0228] Further, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5 and R6 each independently are a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0229] Further, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is further preferred that: R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5 and R6 each independently are a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0230] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., more preferably, R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0231] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., more preferably, R1 and R2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 carbon atom.

[0232] In addition, in the above formula (I) of the above dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., preferably, R1 and R2 each independently represent an alkyl group having 4 to 6 carbon atoms, and R3, R4, and R6 represent hydrogen atoms, and R5 is an alkyl group having 1 to 4 carbon atoms.

[0233] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., the compound of the above formula (I) of the above dye is preferably the following compound, and more preferably the compounds of formula (1) and (2).

[0234] [Chemical formula 7]

[0235]

[0236] <Method for producing the compound of formula (I)>

[0237] A method for producing the compound represented by the above formula (I) will be described.

[0238] [Chemical formula 8]

[0239]

[0240] The compound represented by the above formula (I) is obtained by formylating an aniline derivative represented by formula (i-A) (in formula (i-A), R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.) and then subjecting malononitrile to a condensation reaction.

[0241] (i) Formylation of the compound of formula (i-A)

[0242] First, phosphorus oxychloride is added to an N,N-dimethylformamide (DMF) solution of the compound of formula (i-A) for formylation to obtain a formylated product.

[0243] The reaction temperature for formylation is preferably from 0 to 20 °C, more preferably from 0 to 10 °C.

[0244] (ii) Condensation reaction with malononitrile

[0245] Malononitrile is added to a solution of the formylated product of formula (i-A) in DMF and an alcohol, and an organic base is used as a catalyst. Stirring is carried out in a temperature range of, for example, 10 to 85 °C, preferably 40 to 85 °C, to obtain the compound represented by the above formula (I). Examples of the alcohol used include methanol and ethanol. In addition, examples of the organic base used include pyridine and triethylamine.

[0246] (iii) Method for manufacturing the compound of formula (i-A)

[0247] The compound of formula (i-A) as a raw material can be manufactured as follows.

[0248] [Chemical formula 9]

[0249]

[0250] Using DMF as a solvent, the compound represented by formula (i-A1) is reacted with a haloalkyl or haloaryalkyl represented by R1-X and R2-X (R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and X represents a halogen atom) to obtain the compound represented by formula (i-A).

[0251] <Dye for dyeing fibers using supercritical carbon dioxide>

[0252] The dye of the present invention has a compound of formula (I).

[0253] The dye of the present invention may further contain additives. Examples of the above additives include color assistants, dispersants, fillers, stabilizers, plasticizers, nucleating agents, modifiers, foaming agents, ultraviolet absorbers, light stabilizers, antioxidants, antibacterial agents, mildewproof agents, antistatic agents, flame retardants, inorganic fillers, and elastomers for improving impact resistance.

[0254] <Fiber>

[0255] Examples of the fiber of the object to be dyed dyed with the dye composition of the present invention include polyester fiber, polyolefin fiber, acrylonitrile-based fiber, etc., and polyolefin fiber is preferred. In addition, as the fiber of the object to be dyed dyed with the dye of the present invention, polyolefin fiber is more preferred.

[0256] Examples of the above polyolefin fiber include fibers formed of 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 type 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, low-density polyethylene, medium-density polyethylene, high-density polyethylene, linear low-density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, etc. polyethylene-based resins, poly-1-butene, poly-4-methyl-1-pentene, etc.

[0257] The above polymers can be used alone or in combination of two or more to form polyolefin fibers.

[0258] As the above polyolefin fiber, it is preferably formed of a polypropylene-based resin and / or a polyethylene-based resin, and more preferably formed of a polypropylene-based resin.

[0259] The shape of the above polyolefin fiber can be any of block (molded product, etc.), film, fiber (cloth (fabric, woven fabric, non-woven fabric, etc.), yarn (filament yarn, staple fiber yarn, slit film yarn, split film yarn, etc.)), etc., and fiber shape is preferred.

[0260] 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 and mixing other fibers such as polyester in polypropylene fiber.

[0261] <Method for Dyeing Fibers Using Supercritical Carbon Dioxide>

[0262] The present invention is a method for dyeing fibers using supercritical carbon dioxide, which includes: a step of dyeing fibers using the dye of the present invention in the presence of supercritical carbon dioxide. In the above method, supercritical carbon dioxide is used as the dyeing medium.

[0263] Compared with the general dyeing method using water as the dyeing medium, the dyeing method using supercritical carbon dioxide does not use water during dyeing. In addition, since there is no need for a washing process, no wastewater is generated, no dyeing aids are required, the dyeing time is short, and carbon dioxide used as the dyeing medium can be recycled, etc. Therefore, it has attracted attention as an environmentally friendly dyeing method.

[0264] In addition, when dyeing fibers using a polyolefin resin with the dye of the present invention described above, supercritical carbon dioxide is lipophilic, and both the dye of the present invention and the polyolefin resin are lipophilic. Therefore, the affinity of the dyeing medium, the dye, and the object to be dyed is high, and as a result, a high-quality dyed product can be obtained.

[0265] The dyeing process in the fiber dyeing method using supercritical carbon dioxide of the present invention is preferably carried out at a temperature of 31°C or higher and a pressure of 7.4 MPa or higher. Because the above-mentioned dyeing temperature and dyeing pressure must be above the critical point of carbon dioxide as the dyeing medium (7.4 MPa at 31°C).

[0266] In the above dyeing process, the dyeing temperature is mainly determined according to the type of resin of the fiber to be dyed. The above dyeing temperature is usually in the range of 60 to 180°C, preferably in the range of 80 to 160°C.

[0267] In the above dyeing process, the dyeing pressure is mainly determined according to the type of resin of the fiber to be dyed. The above dyeing pressure is usually in the range of about 7.4 to 40.0 MPa, preferably 20 to 30 MPa.

[0268] The dyeing time in the above dyeing process is determined according to the type of resin of the fiber to be dyed and the dyeing temperature. The above dyeing time is usually about 10 to 120 minutes, preferably 30 to 90 minutes.

[0269] In the above dyeing process, the concentration of the above dye relative to the above fiber depends on the type and processing state of the fiber to be dyed. When the fiber to be dyed is in a fibrous state, the concentration of the above dye relative to the above fiber is 0.1 to 6.0% o.m.f. (on the mass of fiber, relative to the fiber mass), preferably 0.1 to 4.0% o.m.f.

[0270] In the dyeing method of the present invention, the liquor ratio (mass ratio of the object to be dyed: carbon dioxide) depends on the type and processing state of the object to be dyed. The above liquor ratio is usually 1:2 to 1:100, preferably 1:5 to 1:75. When the object to be dyed is a cloth wound into an appropriate cheese yarn, in the dyeing method of the present invention, the liquor ratio is relatively low, for example, 1:2 to 1:5.

[0271] <Dyed fiber>

[0272] The present invention provides a fiber which is dyed by the dyeing method of the present invention. The dyed fiber is dyed to a high concentration, especially a high concentration of yellow, and has excellent dye fastness such as light fastness, sublimation fastness, and washing fastness. As uses of the above fiber, for example, clothing items such as clothes, underwear, hats, socks, gloves, and sportswear, vehicle interior materials such as seat covers, carpets, curtains, floor mats, sofa covers, and cushion covers, and interior decoration items can be cited.

[0273] Hereinafter, the present invention will be described more specifically by way of examples, but the solutions of the present invention are not limited to these.

[0274] [Examples]

[0275] (Synthesis Example 1)

[0276] [Synthesis of Yellow Dye Compound (1)]

[0277] The yellow dye compound (1) is produced according to the following scheme.

[0278] [Chemical Formula 10]

[0279]

[0280] (Step 1)

[0281] A mixture of m-toluidine (10.6 g), triethylamine (25.2 g), DMF (30 g), and 1-bromooctane (57.9 g) was heated to 100 °C and stirred at the same temperature for 5 hours to obtain N,N-dioctyl-3-methylaniline represented by the following formula (1a) from the reaction mixture.

[0282] [Chemical Formula 11]

[0283]

[0284] (Step 2)

[0285] Cool the reaction mixture of N,N-dioctyl-3-methylaniline obtained in the above step 1 to 5 °C. Dropwise add phosphoryl chloride (23.0 g) to this mixture within the range of 5 to 10 °C over 1 hour, and then dropwise add pyridine (11.9 g) within the range of 5 to 10 °C. After that, raise the temperature to 40 to 45 °C and stir for 1 hour. After cooling the reaction mixture to 10 °C, dropwise add methanol (40 g) within the range of 10 to 20 °C, and further add anhydrous sodium acetate (35 g) within the range of 10 to 20 °C. Dropwise add a solution obtained by dissolving malononitrile (6.61 g) in methanol (10 g) to this mixture within the range of 10 to 20 °C. Raise the temperature of this mixture to 25 - 30 °C, stir for 30 minutes, then raise the temperature to 85 °C and stir for 4 hours. After cooling the reaction mixture to room temperature, add water (200 g) and ethyl acetate (200 g) to extract the organic layer. After washing with saturated brine, distill off the solvent under reduced pressure. Add methanol (80 g) to this crude product, cool to 0 to 5 °C, filter out the product, wash with methanol, then wash with water, and dry at 50 °C until the water content is below 1.0 wt% to obtain the yellow dye compound represented by the following formula (1) (27.6 g, yield 67.8%). The above yellow dye compound was confirmed by LCMS analysis (m / z 408 (M + )) to confirm its structure.

[0286] [Chemical formula 12]

[0287]

[0288] (Synthesis Example 2)

[0289] [Synthesis of Yellow Dye Compound (2)]

[0290] The yellow dye compound (2) is produced according to the following scheme.

[0291] [Chemical formula 13]

[0292]

[0293] (Step 1)

[0294] Use 1-bromohexane (49.5 g) instead of 1-bromooctane, and otherwise, follow the same steps as in Step 1 of Synthesis Example 1 to obtain N,N-dihexyl-3-methylaniline represented by the following formula (2a) from the reaction mixture.

[0295] [Chemical formula 14]

[0296]

[0297] (Step 2)

[0298] Using the reaction mixture of N,N - dihexyl - 3 - methylaniline obtained in the above step 1 to replace N,N - dioctyl - 3 - methylaniline, and except for this, following the same steps as in step 2 of Synthesis Example 1, a yellow dye compound represented by the following formula (2) was obtained (23.4 g, yield 66.7%). The above yellow dye compound was confirmed for its structure by LCMS analysis (m / z 352 (M + ))

[0299] [Chemical formula 15]

[0300]

[0301] (Synthesis Example 3)

[0302] [Synthesis of yellow dye compound (3)]

[0303] The yellow dye compound (3) is manufactured according to the following scheme.

[0304] [Chemical formula 16]

[0305]

[0306] (Step 1)

[0307] Using aniline (9.31 g) to replace m - toluidine, and except for this, following the same steps as in step 1 of Synthesis Example 1, an N,N - dioctylaniline represented by the following formula (3a) was obtained from the reaction mixture.

[0308] [Chemical formula 17]

[0309]

[0310] (Step 2)

[0311] Using the reaction mixture of N,N - dioctylaniline obtained in the above step 1 to replace N,N - dioctyl - 3 - methylaniline, and except for this, following the same steps as in step 2 of Synthesis Example 1, a yellow dye compound represented by the following formula (3) was obtained (26.5 g, yield 67.4%). The above yellow dye compound was confirmed for its structure by LCMS analysis (m / z 394 (M+)).

[0312] [Chemical formula 18]

[0313]

[0314] (Synthesis Example 4)

[0315] [Synthesis of yellow dye compound (4)]

[0316] The yellow dye compound (4) is manufactured according to the following scheme.

[0317] [Chemical Formula 19]

[0318]

[0319] (Step 1)

[0320] Heat the mixture of N-benzylaniline (18.3 g), triethylamine (17.6 g), DMF (50 g) and 1-bromohexane (33.0 g) to 110 °C and stir at the same temperature for 8 hours to obtain N-benzyl-N-hexylaniline represented by the following formula (4a) from the reaction mixture.

[0321] [Chemical Formula 20]

[0322]

[0323] (Step 2)

[0324] Use the reaction mixture of N-benzyl-N-hexylaniline obtained in the above Step 1 to replace N,N-dioctyl-3-methylaniline, and otherwise, follow the same procedure as in Step 2 of Synthesis Example 1 to obtain the yellow dye compound represented by the following formula (4) (21.2 g, yield 57.1%). The structure of the above yellow dye compound was confirmed by LCMS analysis (m / z 372 (M+)).

[0325] [Chemical Formula 21]

[0326]

[0327] (Synthesis Example 5)

[0328] [Synthesis of Yellow Dye Compound (5)]

[0329] After dropping n-octanoyl chloride (19.5 g) into the mixture of 5-amino-anthra[9,1-cd]isothiazol-6-one (25.2 g), toluene (120 g) and pyridine (9.49 g), heat the mixture to 110 °C and stir for 1 hour. After cooling the mixture to room temperature, add methanol (150 g) to precipitate. Filter the mixture, wash the filtrate with methanol, and dry at 60 °C until the water content is 1.0 wt% or less to obtain the yellow dye compound represented by the following formula (5) (31.8 g, yield 83.9%). The structure of the above yellow dye compound was confirmed by LCMS analysis (m / z 379 (M + ))

[0330] [Chemical Formula 22]

[0331]

[0332] (Synthesis Example 6)

[0333] [Synthesis of Yellow Dye Compound (6)]

[0334] Using 2-ethylhexanoyl chloride (19.5 g) instead of n-octanoyl chloride, and otherwise following the same procedure as in Synthesis Example 5, the yellow dye compound represented by the following formula (6) was obtained (33.1 g, yield 87.3%). The above yellow dye compound was confirmed to have its structure by LCMS analysis (m / z 379 (M + ))

[0335] [Chemical Formula 23]

[0336]

[0337] (Synthesis Example 7)

[0338] [Synthesis of Yellow Dye Compound (7)]

[0339] Using n-nonanoyl chloride (21.2 g) instead of n-octanoyl chloride, and otherwise following the same procedure as in Synthesis Example 5, the yellow dye compound represented by the following formula (7) was obtained (31.0 g, yield 78.9%). The above yellow dye compound was confirmed to have its structure by LCMS analysis (m / z 393 (M + ))

[0340] [Chemical Formula 24]

[0341]

[0342] (Synthesis Example 8)

[0343] [Synthesis of Yellow Dye Compound (8)]

[0344] A mixture of 2-hexyldecanoic acid (30.8 g) and toluene (30 g) was added dropwise to a mixture of thionyl chloride (14.3 g) and toluene (20 g). 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 the reaction mixture 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 to the above reaction mixture. After raising the temperature of the reaction mixture to 110 °C and stirring for 2 hours, the solvent was removed by distillation under reduced pressure from the mixture, and precipitation was induced by adding methanol (100 g) to the residue. The mixture was filtered, the filtrate was washed with methanol and then with water, and dried at 60 °C until the water content was 1.0 wt% or less, to obtain a yellow dye compound represented by the following formula (8) (36.7 g, yield 74.7%). The above yellow dye compound was confirmed by LCMS analysis (m / z 491 (M + )) to confirm its structure.

[0345] [Chemical formula 25]

[0346]

[0347] (Synthesis Example 9)

[0348] [Synthesis of yellow dye compound (9)]

[0349] A mixture of 4-(anilino)-3-nitro-N-phenylbenzenesulfonamide (9.84 g), DMF (15.7 g), potassium carbonate (3.68 g), and 1-bromooctane (7.73 g) was heated to 80 °C and stirred for 2 hours. After cooling the reaction mixture to room temperature, 100 g of water was added thereto to precipitate a solid. The mixture was filtered, the filtrate was washed with methanol and then with water, and dried at 60 °C until the water content was 1.0 wt% or less, to obtain a yellow dye compound represented by the following formula (9) (11.9 g, yield 92.8%). The above yellow dye compound was confirmed by LCMS analysis (m / z 482 (M+)) to confirm its structure.

[0350] [Chemical formula 26]

[0351]

[0352] (Synthesis Example 10)

[0353] [Synthesis of yellow dye compound (10)]

[0354] 1-Bromo-2-ethylhexane (7.73 g) was used instead of 1-bromooctane, and otherwise, the same procedure as in Synthesis Example 9 was followed to obtain a yellow dye compound represented by the following formula (10) (11.5 g, yield 89.7%). The above yellow dye compound was confirmed to have its structure by LCMS analysis (m / z 482 (M + ))

[0355] [Chemical formula 27]

[0356]

[0357] (Synthesis Example 11)

[0358] [Synthesis of yellow dye compound (11)]

[0359] 1-Bromododecane (9.98 g) was used instead of 1-bromooctane, and otherwise, the same procedure as in Synthesis Example 9 was followed to obtain a yellow dye compound represented by the following formula (11) (14.2 g, yield 99.4%). The above yellow dye compound was confirmed to have its structure by LCMS analysis (m / z 538 (M + ))

[0360] [Chemical formula 28]

[0361]

[0362] (Synthesis Example 12)

[0363] [Synthesis of yellow dye compound (12)]

[0364] 1-Bromohexadecane (12.2 g) was used instead of 1-bromooctane, and otherwise, the same procedure as in Synthesis Example 9 was followed to obtain a yellow dye compound represented by the following formula (12) (15.5 g, yield 98.5%). The above yellow dye compound was confirmed to have its structure by LCMS analysis (m / z 594 (M + ))

[0365] [Chemical formula 29]

[0366]

[0367] (Synthesis Example 13)

[0368] [Synthesis of yellow dye compound (13)]

[0369] A mixture of thionyl chloride (14.3 g) and toluene (20 g) was added dropwise to a mixture of 2 - hexyldecanoic acid (30.8 g) and toluene (30 g). After a mixture of pyridine (9.49 g) and toluene (30 g) was slowly added dropwise to this mixture over 1 hour, the temperature was raised to 110 °C and stirred for 1 hour. After the reaction mixture was cooled to room temperature, a mixture of 1 - aminoanthraquinone (22.3 g) and toluene (30 g) was added thereto. After the reaction mixture was heated to 110 °C and stirred for 2 hours, it was cooled to room temperature, 10 g of 24% aqueous sodium hydroxide solution was added, and 200 g of water was added to extract the organic layer. After the extract was washed with saturated brine, the solvent was removed by distillation under reduced pressure. Methanol (200 g) was added to the residue to precipitate a solid. The mixture was filtered, the filtrate was washed with methanol and then with water, and dried at 60 °C until the water content was 1.0 wt% or less to obtain a yellow dye compound represented by the following formula (13) (41.0 g, yield 88.7%). The above yellow dye compound was confirmed by LCMS analysis (m / z 462 (M + )) to confirm its structure.

[0370] [Chemical formula 30]

[0371]

[0372] (Synthesis Example 14)

[0373] [Synthesis of yellow dye compound (14)]

[0374] A mixture of thionyl chloride (28.6 g) and toluene (40 g) was added dropwise to a mixture of 2 - hexyldecanoic acid (61.6 g) and toluene (60 g). After a mixture of pyridine (19.0 g) and toluene (60 g) was slowly added dropwise to this mixture over 1 hour, the temperature was raised to 110 °C and stirred for 1 hour. After the reaction mixture was cooled to room temperature, a mixture of 1,5 - diaminoanthraquinone (23.8 g) and toluene (30 g) was added thereto. After the reaction mixture was heated to 110 °C and stirred for 2 hours, it was cooled to room temperature, 20 g of 24% aqueous sodium hydroxide solution was added, 300 g of water was added, and the organic layer was extracted. After the extract was washed with saturated brine, the solvent was removed by distillation under reduced pressure. Methanol (300 g) was added to the residue to precipitate a solid. The mixture was filtered, the filtrate was washed with methanol and then with water, and dried at 60 °C until the water content was 1.0 wt% or less to obtain a yellow dye compound represented by the following formula (14) (22.6 g, yield 31.6%). The above yellow dye compound was confirmed by LCMS analysis (m / z 715 (M + )) to confirm its structure.

[0375] [Chemical formula 31]

[0376]

[0377] (Synthesis Example 15)

[0378] [Synthesis of Yellow Dye Compound (15)]

[0379] A mixture of 1-aminoanthraquinone (22.3 g), cyanuric chloride (18.4 g), and N-methyl-2-pyrrolidone (NMP) (100 g) was heated to 60 °C and stirred for 2 hours. The reaction mixture was cooled to room temperature, and 200 g of water was added to precipitate the product. The mixture was filtered, and the filtrate was washed with water and dried at 60 °C until the water content was below 1.0 wt%. DMF (60 g), triethylamine (8.1 g), and 2-ethylhexylamine (12.4 g) were added to the resulting solid, and the mixture was heated to 90 °C and stirred for 2 hours. The mixture was cooled to room temperature, 20 g of 30% sulfuric acid was added thereto, and then 100 g of water was added to precipitate the product. The mixture was filtered, and the filtrate was washed with water. Methanol (60 g) was added to the crude product, and the mixture was stirred at 60 °C for 30 minutes. After cooling to room temperature, the mixture was filtered, the filtrate was washed with methanol and then with water, and dried at 60 °C until the water content was below 1.0 wt% to obtain 14.4 g (yield 25.9%) of the yellow dye compound represented by the following formula (15). The above yellow dye compound was confirmed by LCMS analysis (m / z 557 (M + )) for its structure.

[0380] [Chemical Formula 32]

[0381]

[0382] The dye compounds described in the synthesis examples are shown in Tables 1 to 2.

[0383] [Table 1]

[0384]

[0385] Synthesis Example Dye Compound <![CDATA[R1]]> <![CDATA[R2]]> <![CDATA[R3]]> <![CDATA[R4]]> <![CDATA[R5]]> <![CDATA[R6]]> 1 1 <![CDATA[C8H 17 > <![CDATA[C8H 17 > H <![CDATA[CH3]]> H H 2 2 <![CDATA[C6H 13 > <![CDATA[C6H 13 > H <![CDATA[CH3]]> H H 3 3 <![CDATA[C8H 17 > <![CDATA[C8H 17 > H H H H 4 4 <![CDATA[CH2Ph]]> <![CDATA[C6H 13 > H H H H

[0386] [Table 2]

[0387]

[0388]

[0389] [Dyeing Example]

[0390] Using the compounds described in Tables 1 and 2, polypropylene cloth or polyethylene cloth was dyed by supercritical carbon dioxide dyeing method.

[0391] (Supercritical Carbon Dioxide Dyeing of Polypropylene Cloth)

[0392] (Dyeing Example P1)

[0393] The supercritical carbon dioxide dyeing apparatus used in dyeing is shown in Figure 1 .

[0394] The dyeing apparatus consists of a liquid CO2 gas cylinder (1), a filter (2), a cooling jacket (3), a cooler (4), a high-pressure pump (5), a preheater (6), pressure gauges (7 to 9), a magnetic drive section (10), a DC motor (11), safety valves (12, 13), stop valves (14 to 18), a needle valve (19), and a heater (20).

[0395] The polypropylene cloth is cut and weighed to about 50 to 70 g, and then wound around a perforated stainless-steel drum (21) in the order of cotton cloth, polypropylene cloth, and cotton cloth from the inside, and then loosely fixed with cotton yarn. The inner cotton cloth is the lining cloth, and the outer cotton cloth is the covering cloth.

[0396] The stainless-steel drum wound with the above cloth sample (cotton cloth, polypropylene cloth, cotton cloth) is fixed in a pressure-resistant stainless-steel tank (22). A yellow dye compound 1 obtained in Synthesis Example 1 equivalent to 0.3% by mass relative to the mass of the polypropylene cloth is wrapped in a wiping paper and placed in the fluid passage above the stainless-steel drum. The volume of the pressure-resistant stainless-steel tank is 2230 cm 3 . All the valves in the dyeing apparatus are closed, and it is heated to 120 °C using the preheater.

[0397] After reaching the dyeing temperature, open stop valves (14) and (16), and flow 1.13 kg of liquid carbon dioxide into the pressure-resistant stainless-steel tank using a high-pressure pump via the cooling jacket. Then, close stop valves (14) and (16), and circulate it using the impeller and magnetic drive section at the lower part inside the pressure-resistant stainless-steel tank. The rotational speed of the magnetic drive section is 750 rpm, and the circulation direction is from the inside to the outside of the drum.

[0398] After reaching the specified temperature and pressure (120 °C, 25 MPa) inside the pressure-resistant stainless-steel tank, maintain these temperature and pressure conditions for 60 minutes to dye the polypropylene cloth. After dyeing, open stop valve (18), and slowly open the needle valve to release the carbon dioxide inside the pressure-resistant stainless-steel tank, reducing the pressure inside the pressure-resistant stainless-steel tank from 25 MPa to atmospheric pressure. The circulation continues until the critical pressure of carbon dioxide (about 8 MPa) is reached. Then, take out the polypropylene yellow dyed cloth inside the pressure-resistant stainless-steel tank.

[0399] (Dyeing Examples P2 to P14)

[0400] The dye compound 1 described in Dyeing Example P1 was changed to the dye compounds described in Tables 1 and 2, and a polypropylene yellow dyed fabric was obtained through the same dyeing procedure as in Dyeing Example P1. The dye compounds used in Dyeing Examples P1 to P14 are shown in Tables 3 to 4.

[0401] [Table 3]

[0402]

[0403] Dyeing Example Dye Compound <![CDATA[R1]]> <![CDATA[R2]]> <![CDATA[R3]]> <![CDATA[R4]]> <![CDATA[R5]]> <![CDATA[R6]]> P1 1 <![CDATA[C8H 17 > <![CDATA[C8H 17 > H <![CDATA[CH3]]> H H P2 2 <![CDATA[C6H 13 > <![CDATA[C6H 13 > H <![CDATA[CH3]]> H H P3 4 <![CDATA[CH2Ph]]> <![CDATA[C6H 13 > H H H H

[0404] [Table 4]

[0405]

[0406]

[0407] For the polypropylene dyed fabrics obtained in Dyeing Examples P1 to P14, 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.

[0408] (1) Dyeing property evaluation

[0409] The dyeing property was evaluated visually by the Total K / S value, K / S value (measured at the maximum wavelength), and the dye residue after dyeing obtained by colorimetry of the dyed fabric. Colorimetry of the dyed fabric was carried out using an integrating sphere spectrophotometer Color-Eye5 (manufactured by GretagMacbeth) with the dyed fabric pasted on white paper and observed under a light source D65 and a 2-degree field of view.

[0410] (2) Light fastness test

[0411] The light fastness test was carried out by the ultraviolet carbon arc lamp method according to JIS L0842:2004. The outline of the test method is as follows. Using an ultraviolet flash counter U48 (manufactured by Suga Test Instruments Co., Ltd.), after exposing the dyed fabric for 20 hours under the condition of a black panel temperature of 63 ± 3 °C, the determination of color change and fading was carried out.

[0412] (3) Sublimation fastness test

[0413] The sublimation fastness test was carried out by the method according to JIS L0854:2013. The outline of the test method is as follows. The dyed fabric was clamped in a nylon cloth, and after maintaining it at 120 ± 2 °C for 80 minutes under a load of 12.5 kPa, the determination of color change, fading, and contamination of the nylon cloth was carried out.

[0414] (4) Washing fastness test

[0415] 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 described below. A multi-fiber interwoven fabric was attached to the dyed fabric, and washing was carried out for 30 minutes at 50 ± 2 °C in the presence of soap. Fading and discoloration and the contamination of the cotton part and nylon part of the multi-fiber interwoven fabric were judged. In addition, the contamination of the residual liquid after washing was judged.

[0416] (5) Perspiration fastness test

[0417] The perspiration fastness test was carried out according to the method of JIS L0848:2004. The outline of the test method is as described below. A multi-fiber interwoven fabric was attached to the dyed fabric, and after impregnating in acidic artificial perspiration or alkaline artificial perspiration for 30 minutes, it was kept at 37 ± 2 °C for 4 hours under a load of 12.5 kPa, and then dried below 60 °C. Fading and discoloration and the contamination of the cotton part and nylon part of the multi-fiber interwoven fabric were judged.

[0418] (6) Rubbing fastness test

[0419] The rubbing fastness test was carried out according to the method of JIS L0849:2013. The outline of the test method is as described below. Using a rubbing fastness tester RT-300 (manufactured by Dainichi Kagaku Seiki Co., Ltd.), 100 reciprocating rubs were carried out on the dyed fabric with a dry cotton cloth or a wet cotton cloth under a load of 2 N, and the coloring of the cotton cloth was judged.

[0420] (7) Fastness test against hot pressing

[0421] 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 described below. The dyed fabric was overlapped on the cotton cloth, and after keeping it under a load of 4 ± 1 kPa for 15 seconds with a heating plate at 150 °C, fading and discoloration and the contamination of the cotton cloth were judged.

[0422] The evaluation results of the dyeing examples of the compound of formula (I) are shown in Table 5, and the evaluation results of the dyeing examples of dye compounds other than the compound of formula (I) are shown in Table 6.

[0423] Table 5

[0424]

[0425]

[0426] Regarding the dyeability of the compound of formula (I), the dyeability of the compound in which R1 and R2 used in Dyeing Examples P1 to P3 are each independently a branched alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 12 carbon atoms, and R3, R4, R5 and R6 are each independently a hydrogen atom or a branched alkyl group having 1 to 4 carbon atoms is good.

[0427] However, the dyeability of dye compounds other than the compound of formula (I) used in Dyeing Examples P4 to P14 is poor.

[0428] In addition, regarding each fastness of the compound of formula (I), each fastness of the compound in which R1 and R2 used in Dyeing Example P1 or P2 are each independently a branched alkyl group having 4 to 8 carbon atoms, and R3, R4, R5 and R6 are each independently a hydrogen atom or a branched alkyl group having 1 to 4 carbon atoms is good.

[0429] As described above, the present invention is not limited to the above-described embodiments, and modes obtained by appropriately combining the configurations of the embodiments or modes obtained by substitution are also included in the present invention.

[0430] 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 or the like can be made to the embodiments. Embodiments subjected to such modifications are also included in the scope of the present invention.

[0431] The present invention can be used for dyeing fibers used in clothing items such as clothes, underwear, hats, socks, gloves, sportswear, interior decoration materials for vehicles such as seat covers, carpets, curtains, floor mats, sofa covers, cushion covers, and the like.

Claims

1. A dye for dyeing fibers using supercritical carbon dioxide, which comprises a compound of the following general formula (I), In formula (I), R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, R3, R4, R5 and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

2. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

3. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

4. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

5. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

6. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

7. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

8. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

9. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

10. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

11. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

12. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

13. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

14. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

15. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

16. The dye according to claim 1, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

17. The dye according to claim 1, wherein, The compound of the general formula (I) is selected from the compounds represented by the following formulas (1) to (4).

18. A method for dyeing fibers using supercritical carbon dioxide, which comprises: A process for dyeing a fiber in the presence of supercritical carbon dioxide using the dye according to any one of claims 1 to 17.

19. The dyeing method according to claim 18, wherein, The dyeing process is carried out at a pressure of 31 °C or higher and 7.4 MPa or higher.

20. The dyeing method according to claim 18 or 19, wherein, The concentration of the dye relative to the fiber ranges from 0.1 to 6.0% o.m.f., where o.m.f. means on the mass of fiber, based on the mass of the fiber.

21. A fiber dyed by the dyeing method according to any one of claims 18 to 20.

22. A compound of the following general formula (I), In formula (I), R1 and R2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms, R3, R4, R5 and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

23. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

24. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

25. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

26. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

27. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

28. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

29. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

30. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

31. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

32. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

33. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

34. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

35. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms.

36. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted by an alkyl group having 1 to 2 carbon atoms.

37. The compound according to claim 22, wherein, In the formula (I), R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

38. The compound according to claim 22, wherein, The compound of the general formula (I) is selected from the compounds represented by the following formula (1) to formula (4),

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