Dye for dyeing using supercritical carbon dioxide

Abstract

The present invention addresses the problem of providing: a dye for dying fibers using supercritical carbon dioxide, which can dye fibers highly dense yellow and can provide a dyed product having excellent color fastness to light, sublimation, laundering and the like; a method for dying fibers using supercritical carbon dioxide; fibers dyed by the dying method; and a compound.　Provided are: a dye for dying fibers using supercritical carbon dioxide, the dye comprising a compound represented by formula (I); a method for dying fibers using supercritical carbon dioxide; fibers dyed by the dying method; and a compound. [Chemical formula 1] [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 and 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.]

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 dyeing method, and a compound.

Background Art

[0002] Polyolefin resins such as polypropylene resin and polyethylene resin are crystalline thermoplastic resins, and have excellent properties such as low cost, easy processability, high strength, high chemical resistance, high abrasion resistance, high flexural resistance, light weight, low hygroscopicity, low thermal conductivity, high antistatic property, and recyclability.

[0003] On the other hand, polyolefin resins are high molecular compounds composed of hydrocarbons in both the main chain and side chains, and have low affinity and compatibility with conventional dye compounds, and do not have functional groups effective for chemical reactions. For these reasons, it has been extremely difficult to achieve high-concentration and high-fastness dyeing.

[0004] Therefore, most of the colored polyolefin resins currently on the market are those in which a colored pigment is added at the manufacturing stage such as polymer pellets, and then spun and formed into 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. Also, considering profitability, 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, a process of replacing the colored resin of the previous color remaining in the resin product manufacturing apparatus with the colored resin of the next color is required, and at that time, a large amount of waste resin is generated, and problems such as waste of time and energy occur.

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

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

[0009] The reason for this is that, as described above, it is extremely difficult to achieve high-concentration and high-fastness dyeing of polypropylene resin fibers and polyethylene resin fibers. In the mass coloring method using colored pigments, which is the only effective coloring method, the single-filament fineness has to be increased, and the freedom of color selection is restricted.

[0010] Heretofore, in order to dye polyolefin resin fibers with an aqueous solution, attempts have been made to change the molecular structure of dyes. 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 propose dyes for dyeing polyolefin resin fibers.

[0011] Japanese Patent Publication No. 38-10741 describes production examples of red dyes and purple dyes in which a phenoxy group having an alkyl group or cycloalkyl group having 3 to 12 carbon atoms as a substituent is introduced into an anthraquinone-based dye, and dyeing examples of polypropylene resin fibers using them.

[0012] However, it is difficult to achieve high-concentration dyeing of polyolefin resin fibers with these anthraquinone-based red dyes or anthraquinone-based purple dyes. Furthermore, regarding the form of the dyes used for dyeing, there are descriptions such as dissolving these anthraquinone-based red dyes in alcohol or acetone, which are organic solvents, before use, and it is hard to say that they are environmentally friendly. In addition, there is no description about yellow dyes.

[0013] Japanese Patent Publication No. 40-1277 describes examples of the production of blue dyes in which a phenoxy group having an alkyl group, cycloalkyl group or halogeno group having 1 to 9 carbon atoms as a substituent is introduced into an anthraquinone dye, and examples of the dyeing of polyester fibers, polyamide fibers and polyolefin resin fibers using them.

[0014] However, with these anthraquinone blue dyes, high-concentration dyeing of polyolefin resin fibers is difficult, and no specific description is given regarding the dyeing fastness of the resulting dyed products. Furthermore, regarding the form of the dye when used for dyeing, there are descriptions such as dissolving these anthraquinone blue dyes in alcohol or acetone, which are organic solvents, before use, and it is hard to say that they are environmentally friendly. In addition, there is no description of yellow dyes.

[0015] Japanese Patent Publication No. 41-3515 describes examples of the production of blue dyes in which a phenoxy group having an alkyl group having 1 to 9 carbon atoms or a halogeno group as a substituent is introduced into an anthraquinone dye, and examples of the dyeing of polyolefin resin fibers using them.

[0016] However, with these anthraquinone blue dyes, high-concentration dyeing of polyolefin resin fibers is difficult, and no specific description is given regarding the dyeing fastness of the resulting dyed products. Furthermore, regarding the form of the dye when used for dyeing, there are descriptions such as dissolving it in alcohol or acetone, which are organic solvents, before use, and it is hard to say that this is environmentally friendly. In addition, there is no description of yellow dyes.

[0017] British Patent Specification No. 872,882 describes an example of the dyeing of polyolefin resin fibers using a blue dye in which an alkylamino group or cycloalkylamino group is introduced at the α-position of an anthraquinone dye.

[0018] However, with these anthraquinone-based blue dyes, it is difficult to perform high-concentration dyeing of polyolefin resin fibers, and no specific description is provided regarding the dye fastness of the resulting dyed products. Additionally, there is no description regarding yellow dyes.

[0019] U.S. Patent No. 3,536,735 describes production examples of red dyes in which a phenoxy group having two substituents selected from a sec-butyl group, a sec-pentyl group, and a tert-pentyl group is introduced into anthraquinone-based dyes, and dyeing examples of polypropylene resin fibers using them.

[0020] However, with these anthraquinone-based red dyes, it is difficult to perform high-concentration dyeing of polyolefin resin fibers, and no specific description is provided regarding the dye fastness of the resulting dyed products. Furthermore, regarding the form of the dye when used for dyeing, there is a description such as dissolving it in dimethylformamide, which is an organic solvent, and then using it, and it is hard to say that this is environmentally friendly. Additionally, there is no description regarding yellow dyes.

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

[0022] However, with the described anthraquinone-based yellow dyes having a long-chain alkyl group, it is difficult to perform high-concentration dyeing of polypropylene fibers.

[0023] Japanese Patent Application Laid-Open No. 55-152869 describes production examples of monoazo-based dyes having a long-chain alkyl group and dyeing examples of fine denier polyester fibers using them. However, no dyeing examples for polyolefin-based fibers using them are described. Additionally, there is no description regarding yellow dyes.

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

[0025] As modification techniques, various methods are known, such as blending with a dyeable resin component such as polyester, copolymerization with a vinyl monomer having a dyeable group, and blending with a dyeing accelerator such as a metal stearate.

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

[0027] By the way, Japanese Patent No. 3253649 discloses, as a dyeing method alternative to aqueous dyeing, using supercritical carbon dioxide as a dyeing medium and dyeing a hydrophobic fiber material with various dyes.

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

[0029] Japanese Patent No. 6721172 discloses using supercritical carbon dioxide as a dyeing medium and dyeing polypropylene fibers, which are polyolefin fibers, with anthraquinone-based blue dyes, anthraquinone-based yellow dyes, anthraquinone-based red dyes, and mixtures of these dyes.

[0030] However, high-concentration dyeing of polypropylene fibers is difficult with the anthraquinone-based yellow dyes described.

[0031] When a method for highly concentrated and highly fast dyeing of polypropylene resin fibers and polyethylene resin fibers is put into practical use, it becomes possible to color inexpensive regular yarns with uncolored fine denier without color number limitation, and new application developments are expected in fields such as clothing and vehicle interior materials that require high designability and where polypropylene resin fibers and polyethylene resin fibers have not been applied so far.

Summary of the Invention

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

[0033]

Chemical Formula

[0034] [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 with 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.]

Brief Description of the Drawings

[0035]

Figure 1

[0036] Therefore, an object of the present invention is to provide a dye for dyeing fibers using supercritical carbon dioxide, a method for dyeing fibers using supercritical carbon dioxide, fibers dyed by the dyeing method, and a compound, which can dye fibers in a high concentration of yellow and have excellent dyeing fastness such as light resistance, sublimation resistance, and washing resistance of the dyed product.

[0037] The present invention is a dye for dyeing fibers using supercritical carbon dioxide, which contains a compound represented by the following general formula (I).

[0038] [Chem.]

[0039] [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 with 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.]

[0040] Furthermore, 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 dye of the present invention.

[0041] Furthermore, the present invention provides fibers dyed by a dyeing method including a step of dyeing fibers in the presence of supercritical carbon dioxide using the dye of the present invention.

[0042] Furthermore, the present invention provides a compound represented by the following general formula (I).

[0043] [Chem.]

[0044] [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 with 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.]

[0045] The dye of the present invention can dye fibers yellow at a high concentration in the presence of supercritical carbon dioxide, and the dyed product has excellent dye fastness such as light fastness, sublimation fastness, and washing fastness.

[0046] The inventors have found that a dye containing the following specific compound has improved affinity for fibers and can dye fibers yellow at a high concentration in the presence of supercritical carbon dioxide, and thus completed the present invention.

[0047] <Compound of formula (I)> The compound of general formula (I) contained in the dye of the present invention is as follows.

[0048] [Chemical formula]

[0049] [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 with 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.]

[0050] In the formula (I), examples of the alkyl group having 4 to 14 carbon atoms include an n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, 2-methylbutyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 1-ethyl-1-methylpropyl group, n-octyl group, 2-ethylhexyl group, n-decyl group, n-dodecyl group, and n-tetradecyl group. Among these, as the alkyl group having 4 to 14 carbon atoms, an alkyl group having 4 to 12 carbon atoms is preferable, an alkyl group having 4 to 10 carbon atoms is more preferable, and an alkyl group having 4 to 8 carbon atoms is even more preferable.

[0051] In the formula (I), examples of the aralkyl group having 7 to 12 carbon atoms include a benzyl group, phenethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, and the like. Among these, an aralkyl group having 7 to 10 carbon atoms is preferable, an aralkyl group having 7 to 9 carbon atoms is more preferable, and an aralkyl group having 7 carbon atoms is even more preferable.

[0052] In the 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 a 4-methylbenzyl group, 4-methylphenethyl group, 4-ethylbenzyl group, 4-ethylphenethyl group, 4-n-propylbenzyl group, 4-n-propylphenethyl group, 4-n-butylbenzyl group, 4-n-butylphenethyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 4-tert-butylphenethyl group, and the like. Among these, an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms is preferable, an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms is more preferable, and an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms is even more preferable.

[0053] In the formula (I), the alkyl group having 1 to 4 carbon atoms includes, for example, linear or branched alkyl groups having 1 to 4 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group and the like. As the alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 3 carbon atoms is preferable, an alkyl group having 1 or 2 carbon atoms is more preferable, and an alkyl group having 1 carbon atom is even more preferable.

[0054] The present invention also provides a compound of formula (I).

[0055]

Chemical formula

[0056] [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 with 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.]

[0057] In the formula (I), R1 and R2 each independently preferably represent a branched or unbranched 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; more preferably represent a branched or unbranched 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; even more preferably represent a branched or unbranched 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.

[0058] Also, in the formula (I), R1 and R2 are each independently preferably a branched or unbranched 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 or unbranched 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 or unbranched 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 or unbranched 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.

[0059] Also, in the formula (I), R1 and R2 are each independently preferably a branched or unbranched 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 or unbranched 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 or unbranched 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 or unbranched 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.

[0060] Also, in the formula (I), R1 and R2 are each independently preferably a branched or unbranched 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 or unbranched 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 or unbranched 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 or unbranched 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.

[0061] Also, in the formula (I), R3, R4, R5, and R6 are each independently preferably a hydrogen atom or a branched or unbranched alkyl group having 1 to 4 carbon atoms.

[0062] Also, in the 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.

[0063] Also, in the 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.

[0064] Also, in the formula (I), R3, R4, R5, and R6 are each independently even more preferably a hydrogen atom or an alkyl group having 1 carbon atom.

[0065] Also, in the formula (I), R1 and R2 are each independently 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.

[0066] Further, in the formula (I), it is more preferable that R1 and R2 are each independently an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0067] Further, in the formula (I), it is more preferable that R1 and R2 are each independently 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.

[0068] Further, in the formula (I), it is more preferable that R1 and R2 are each independently 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.

[0069] Further, in the formula (I), it is more preferable that R1 and R2 are each independently an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0070] Further, in the formula (I), it is more preferable that 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.

[0071] Further, in the formula (I), it is more preferable that 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 2 carbon atoms.

[0072] Further, in the formula (I), it is more preferable that 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.

[0073] Further, in the formula (I), it is more preferable that R1 and R2 are each independently 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.

[0074] Further, in the formula (I), it is more preferable that 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.

[0075] Further, in the formula (I), it is more preferable that 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 2 carbon atoms.

[0076] Further, in the formula (I), it is more preferable that R1 and R2 are each independently an alkyl group having 4 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.

[0077] Further, in the formula (I), it is more preferable that R1 and R2 are each independently 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.

[0078] Further, in the formula (I), it is more preferable that R1 and R2 are each independently 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.

[0079] Further, in the formula (I), it is more preferable that R1 and R2 are each independently an alkyl group having 4 to 12 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

[0080] Further, in the formula (I), it is more preferable that 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.

[0081] Further, in the formula (I), it is more preferable that 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 2 carbon atoms.

[0082] Further, in the formula (I), it is more preferable that 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.

[0083] Further, in the formula (I), it is more preferable that R1 and R2 are each independently 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.

[0084] Further, in the formula (I), it is more preferable that 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.

[0085] Further, in the formula (I), it is more preferable that 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 10 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.

[0086] Further, in the formula (I), it is more preferable that R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.

[0087] Further, in the formula (I), it is more preferable that 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.

[0088] Further, in the formula (I), it is more preferable that 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 2 carbon atoms.

[0089] Further, in the formula (I), it is more preferable that R1 and R2 are each independently an alkyl group having 4 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

[0090] Further, in the formula (I), it is more preferable that 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.

[0091] Further, in the formula (I), it is more preferable that 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 2 carbon atoms.

[0092] Further, in the formula (I), it is more preferable that 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.

[0093] Further, in the formula (I), it is more preferable that R1 and R2 are each independently 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.

[0094] Further, in the formula (I), it is more preferable that 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.

[0095] Further, in the formula (I), it is more preferable that 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 2 carbon atoms.

[0096] Further, in the formula (I), it is more preferable that R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.

[0097] Further, in the formula (I), it is more preferable that 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.

[0098] Further, in the formula (I), it is more preferable that 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 2 carbon atoms.

[0099] Further, in the formula (I), it is more preferable that R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

[0100] Further, in the formula (I), it is more preferable that 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.

[0101] Further, in the formula (I), it is more preferable that 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.

[0102] Further, in the formula (I), it is more preferable that 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.

[0103] Further, in the formula (I), it is more preferable that 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.

[0104] Further, in the formula (I), it is more preferable that 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.

[0105] Further, in the formula (I), it is more preferable that 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.

[0106] Further, in the formula (I), 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 it is more preferable that R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0107] Further, in the formula (I), 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, More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0108] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0109] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0110] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0111] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0112] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0113] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0114] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0115] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0116] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0117] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0118] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0119] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0120] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0121] In the formula (I), 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. More preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0122] In the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0123] In the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0124] In the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0125] In the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0126] In the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0127] Also, in the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0128] Also, in the formula (I), 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 2 carbon atoms. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0129] Also, in the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0130] Also, in the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0131] Also, in the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0132] In the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0133] In the formula (I), 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0134] In the formula (I), R1 and R2 each independently represent an alkyl group having 4 to 6 carbon atoms. R3, R4, and R6 represent a hydrogen atom. Preferably, R5 is an alkyl group having 1 to 4 carbon atoms.

[0135] The compound of formula (I) is preferably the following compounds, and more preferably the compounds of formula (1) and (2).

[0136]

Chemical formula

[0137] The compound of formula (I) is a yellow dye compound.

[0138] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc. R1 and R2 are each independently preferably a branched or unbranched 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 or unbranched 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 preferably a branched or unbranched 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.

[0139] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently preferably a branched or unbranched 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 or unbranched 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 or unbranched 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 preferably a branched or unbranched 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.

[0140] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently preferably an optionally 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, more preferably an optionally 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, still more preferably an optionally 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, and even more preferably an optionally 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.

[0141] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently preferably an optionally 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 an optionally 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 an optionally 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 an optionally 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.

[0142] Further, in the formula (I) of the 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 an optionally branched alkyl group having 1 to 4 carbon atoms.

[0143] Further, in the formula (I) of the 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.

[0144] Also, in the formula (I) of the 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 or 2 carbon atoms.

[0145] Also, in the formula (I) of the 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.

[0146] Also, in the formula (I) of the 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.

[0147] Also, in the formula (I) of the 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.

[0148] Also, in the formula (I) of the 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.

[0149] Further, in the formula (I) of the dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is more preferable that R1 and R2 are each independently 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.

[0150] Further, in the formula (I) of the dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is more preferable that R1 and R2 are each independently an alkyl group having 4 to 14 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

[0151] Further, in the formula (I) of the dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is more preferable that 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.

[0152] Further, in the formula (I) of the dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is more preferable that 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 2 carbon atoms.

[0153] Further, in the formula (I) of the dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., it is more preferable that 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.

[0154] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., It is more preferable that R1 and R2 are each independently 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.

[0155] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., It is more preferable that 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.

[0156] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., It is more preferable that R1 and R2 are each independently 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.

[0157] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., It is more preferable that R1 and R2 are each independently an alkyl group having 4 to 12 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

[0158] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., It is more preferable that R1 and R2 are each independently 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.

[0159] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0160] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more preferably an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0161] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0162] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0163] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more preferably an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0164] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0165] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0166] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0167] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more preferably an alkyl group having 4 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.

[0168] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0169] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0170] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more preferably an alkyl group having 4 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

[0171] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0172] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0173] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more preferably an alkyl group having 4 to 10 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms.

[0174] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0175] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0176] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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.

[0177] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more preferably an alkyl group having 4 to 8 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.

[0178] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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 with an alkyl group having 1 to 4 carbon atoms.

[0179] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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 with an alkyl group having 1 to 2 carbon atoms.

[0180] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more preferably an alkyl group having 4 to 8 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

[0181] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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 with an alkyl group having 1 to 4 carbon atoms.

[0182] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more 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 with an alkyl group having 1 to 2 carbon atoms.

[0183] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 are each independently more preferably an alkyl group having 4 to 8 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms.

[0184] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., More preferably, each of R1 and R2 is 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.

[0185] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., In the formula (I), more preferably, each of R1 and R2 is 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.

[0186] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., In the formula (I), more preferably, each of R1 and R2 is independently an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0187] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, more preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0188] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, more preferably, each of R3, R4, R5, and R6 is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0189] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, It is more preferable that R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0190] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, It is more preferable that R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0191] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, It is more preferable that R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0192] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, It is more preferable that R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0193] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, It is more preferable that R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0194] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, It is more preferable that R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0195] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, It is more preferable that R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0196] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0197] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0198] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0199] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0200] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0201] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0202] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0203] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0204] In the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, R3, R4, R5, and R6 are each independently more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0205] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, R3, R4, R5, and R6 are each independently more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0206] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, R3, R4, R5, and R6 are each independently more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0207] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, R3, R4, R5, and R6 are each independently more preferably a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0208] Further, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 carbon atom.

[0209] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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 2 carbon atoms. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0210] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0211] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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. More preferably, R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0212] Also, in the formula (I) of the dye, From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, more preferably, R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0213] Also, in the formula (I) of the dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, more preferably, R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0214] Also, in the formula (I) of the dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., 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, more preferably, R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 carbon atom.

[0215] Also, in the formula (I) of the dye, from the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., R1 and R2 each independently represent an alkyl group having 4 to 6 carbon atoms, R3, R4, and R6 represent hydrogen atoms, preferably, R5 is an alkyl group having 1 to 4 carbon atoms.

[0216] From the viewpoints of dyeing concentration, light fastness, sublimation fastness, etc., the compound of the formula (I) of the dye is preferably the following compound, and the compounds of the formulas (1) and (2) are more preferable.

[0217]

Chem.

[0218] <Process for Preparing the Compound of Formula (I)> The process for preparing the compound represented by the above formula (I) will be described.

[0219]

Chem.

[0220] 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.

[0221] (i) Formylation of the Compound of Formula (i-A) First, phosphorus oxychloride is added to a solution of the compound of formula (i-A) in N,N-dimethylformamide (DMF) for formylation to obtain a formylated product.

[0222] The reaction temperature for formylation is preferably 0 to 20 °C, more preferably 0 to 10 °C.

[0223] (ii) Condensation Reaction with Malononitrile Malononitrile is added to a solution of the formylated product of formula (i-A) in DMF and alcohols, and the mixture is stirred in the presence of an organic base as a catalyst, for example, in the temperature range of 10 to 85 °C, preferably 40 to 85 °C, to obtain the compound represented by the above formula (I). Examples of the alcohols used include methanol and ethanol. Examples of the organic bases used include pyridine and triethylamine.

[0224] (iii) Process for producing the compound of formula (i-A) The compound of formula (i-A) as a raw material can be produced as follows.

[0225] [Chemical formula]

[0226] Using DMF as a solvent, react the compound represented by formula (i-A1) with an alkyl halide or aralkyl halide represented by R1-X and R2-X (wherein R1 and R2 are each independently 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 a compound represented by formula (i-A).

[0227] [Dye for dyeing fibers using supercritical carbon dioxide] The dye of the present invention has a compound of formula (I).

[0228] The dye of the present invention may further contain an additive. Examples of the additive include a co-colorant, a dispersant, a filler, a stabilizer, a plasticizer, a crystal nucleating agent, a modifier, a foaming agent, an ultraviolet absorber, a light stabilizer, an antioxidant, an antibacterial agent, a fungicide, an antistatic agent, a flame retardant, an inorganic filler, and an elastomer for improving impact resistance, etc.

[0229] [Fiber] Examples of the fiber, which is a dyed object dyed with the dye composition of the present invention, include polyester fiber, polyolefin fiber, acrylic fiber, etc., and polyolefin fiber is preferred. Further, polyolefin fiber is more preferred as the fiber which is a dyed object dyed with the dye of the present invention.

[0230] Examples of the polyolefin fiber include fibers formed from a polymer selected from homopolymers of α-olefins such as propylene, ethylene, 1-butene, 3-methyl-1-butene, 4-methyl-1-pentene, and 1-octene, copolymers of these α-olefins, and copolymers of these α-olefins and other unsaturated monomers copolymerizable therewith. Examples of the copolymer include block copolymers, random copolymers, and graft copolymers. Specific examples of the polymer include polypropylene-based resins such as propylene homopolymers, propylene-ethylene block copolymers, propylene-ethylene random copolymers, and propylene-ethylene-(1-butene) copolymers, polyethylene-based resins such as low-density polyethylene, medium-density polyethylene, high-density polyethylene, linear low-density polyethylene, ethylene-vinyl acetate copolymers, and ethylene-ethyl acrylate copolymers, poly-1-butene, poly-4-methyl-1-pentene, and the like.

[0231] The above polymers may be used alone or in combination to form the polyolefin fibers.

[0232] The polyolefin fibers are preferably made of a polypropylene-based resin and / or a polyethylene-based resin, and more preferably made of a polypropylene-based resin.

[0233] The polyolefin fiber may be in any shape, for example, a block (molded product, etc.), a film, a fiber (cloth (woven fabric, knitted fabric, nonwoven fabric, etc.), thread (filament yarn, spun yarn, slit yarn, split yarn, etc.), etc.), and is preferably in a fiber shape.

[0234] The polyolefin fiber may be a fiber formed by blending other polymer components with polypropylene resin and / or polyethylene resin, bonding, etc. The polyolefin fiber may be a fiber obtained by blending or blending polypropylene fiber with other fibers such as polyester.

[0235] <Method of dyeing textiles using supercritical carbon dioxide> The present invention relates to 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 dye of the present invention. In the method, supercritical carbon dioxide is used as the dyeing medium.

[0236] A dyeing method using supercritical carbon dioxide as the dyeing medium is attracting attention as an environmentally friendly dyeing method because, compared with a general dyeing method using water as the dyeing medium, it does not use water during dyeing, does not generate wastewater because a washing step is unnecessary, does not require a dyeing assistant, has a short dyeing time, and the carbon dioxide that is the dyeing medium can be reused.

[0237] Also, when dyeing fibers or the like using a polyolefin resin with the dye of the present invention, since supercritical carbon dioxide is lipophilic and both the dye of the present invention and the polyolefin resin are lipophilic, the affinity of each 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.

[0238] The dyeing step in the method for dyeing fibers 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. This is because the dyeing temperature and the dyeing pressure need to be above the critical point of carbon dioxide (7.4 MPa at 31°C), which is the dyeing medium.

[0239] In the dyeing step, the dyeing temperature is mainly determined by the type of resin of the fiber to be dyed. The dyeing temperature is usually in the range of 60 to 180°C, preferably in the range of 80 to 160°C.

[0240] In the dyeing step, the dyeing pressure is mainly determined by the type of resin of the fiber to be dyed. The dyeing pressure is usually in the range of about 7.4 to 40.0 MPa, preferably 20 to 30 MPa.

[0241] The dyeing time in the above dyeing process is determined by the type of resin of the fiber to be dyed and the dyeing temperature. The dyeing time is usually about 10 to 120 minutes, preferably 30 to 90 minutes.

[0242] In the above dyeing process, the concentration of the dye with respect to the fiber depends on the type and processing state of the fiber to be dyed. When the fiber to be dyed is in fibrous form, the concentration of the dye with respect to the fiber is 0.1 to 6.0% o.m.f. (on the mass of fiber), preferably 0.1 to 4.0% o.m.f.

[0243] In the dyeing method of the present invention, the bath 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 bath ratio is usually 1:2 to 1:100, preferably 1:5 to 1:75. When the object to be dyed is a cloth wound around an appropriate cheese, in the dyeing method of the present invention, the bath ratio is relatively low, for example, 1:2 to 1:5.

[0244] <Dyed fiber> The present invention provides a fiber dyed by the dyeing method of the present invention. This dyed fiber is dyed in a high concentration, particularly a high concentration of yellow, and has excellent dye fastness such as light resistance, sublimation resistance, and washing resistance. Examples of the uses of the fiber include clothing items such as clothes, underwear, hats, socks, gloves, and sportswear, vehicle interior materials such as seat covers, and interior items such as carpets, curtains, mats, sofa covers, and cushion covers.

[0245] Hereinafter, the present invention will be described more specifically with reference to examples, but the aspects of the present invention are not limited thereto.

[0246] [Examples] (Synthesis Example 1) [Synthesis of Yellow Dye Compound (1)] Yellow Dye Compound (1) was produced according to the following scheme.

[0247] [Chemical formula]

[0248] (Project 1) 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) as a reaction mixture.

[0249] [Chemical formula]

[0250] (Project 2) The reaction mixture of N,N-dioctyl-3-methylaniline obtained in the above Project 1 was cooled to 5 °C. Phosphorus oxychloride (23.0 g) was added dropwise to this mixture over 1 hour in the range of 5 to 10 °C, and then pyridine (11.9 g) was added dropwise in the range of 5 to 10 °C. After that, the temperature was raised to 40 to 45 °C and stirred for 1 hour. After cooling this reaction mixture to 10 °C, methanol (40 g) was added dropwise in the range of 10 to 20 °C, and then anhydrous sodium acetate (35 g) was added in the range of 10 to 20 °C. A solution of malononitrile (6.61 g) dissolved in methanol (10 g) was added dropwise to this mixture in the range of 10 to 20 °C. This mixture was heated to 25 - 30 °C, stirred for 30 minutes, then heated to 85 °C and stirred for 4 hours. After cooling this reaction mixture to room temperature, water (200 g) and ethyl acetate (200 g) were added to extract the organic layer. After washing with saturated brine, the solvent was distilled off under reduced pressure. Methanol (80 g) was added to this crude product and cooled to 0 to 5 °C, then the product was filtered off, washed with methanol and then with water, and dried at 50 °C until the water content was 1.0 wt% or less to obtain a yellow dye compound (27.6 g, yield 67.8%) represented by the following formula (1). The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 408 (M + ))).

[0251] [Chemical formula]

[0252] (Synthesis Example 2) [Synthesis of Yellow Dye Compound (2)] The yellow dye compound (2) was produced according to the following scheme.

[0253] [Chemical formula]

[0254] (Step 1) N,N-Dihexyl-3-methylaniline represented by the following formula (2a) was obtained as a reaction mixture in the same manner as in Step 1 of Synthesis Example 1, except that 1-bromohexane (49.5 g) was used instead of 1-bromooctane.

[0255] [Chemical formula]

[0256] (Step 2) A yellow dye compound (23.4 g, yield 66.7%) represented by the following formula (2) was obtained in the same manner as in Step 2 of Synthesis Example 1, except that the reaction mixture of N,N-dihexyl-3-methylaniline obtained in Step 1 was used instead of N,N-dioctyl-3-methylaniline. The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 352 (M + ))

[0257] [Chemical formula]

[0258] (Synthesis Example 3) [Synthesis of Yellow Dye Compound (3)] The yellow dye compound (3) was produced according to the following scheme.

[0259] [Chemical formula]

[0260] (Step 1) N,N-Dioctylaniline represented by the following formula (3a) was obtained as a reaction mixture in the same manner as in Step 1 of Synthesis Example 1, except that aniline (9.31 g) was used instead of m-toluidine.

[0261] [Chemical Formula]

[0262] (Step 2) A yellow dye compound (26.5 g, yield 67.4%) represented by the following formula (3) was obtained in the same manner as in Step 2 of Synthesis Example 1, except that the reaction mixture of N,N-dioctylaniline obtained in the above Step 1 was used instead of N,N-dioctyl-3-methylaniline. The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 394 (M+)).

[0263] [Chemical Formula]

[0264] (Synthesis Example 4) [Synthesis of Yellow Dye Compound (4)] Yellow dye compound (4) was produced according to the following scheme.

[0265] [Chemical Formula]

[0266] (Step 1) A mixture of N-benzylaniline (18.3 g), triethylamine (17.6 g), DMF (50 g), and 1-bromohexane (33.0 g) was heated to 110 °C and stirred at the same temperature for 8 hours to obtain N-benzyl-N-hexylaniline represented by the following formula (4a) as a reaction mixture.

[0267] [Chemical Formula]

[0268] (Step 2) A yellow dye compound represented by the following formula (4) (21.2 g, yield 57.1%) was obtained in the same manner as in Step 2 of Synthesis Example 1, except that the reaction mixture of N-benzyl-N-hexylaniline obtained in Step 1 was used instead of N,N-dioctyl-3-methylaniline. The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 372 (M+)).

[0269] [Chemical formula]

[0270] (Synthesis Example 5) [Synthesis of Yellow Dye Compound (5)] n-Octanoyl chloride (19.5 g) was added dropwise to a mixture of 5-amino-anthra[9,1-cd]isothiazol-6-one (25.2 g), toluene (120 g), and pyridine (9.49 g). After the temperature was raised to 110°C and the mixture was stirred for 1 hour, the mixture was cooled to room temperature, and methanol (150 g) was added to precipitate a solid. The mixture was filtered, and the collected solid was washed with methanol 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 (5) (31.8 g, yield 83.9%). The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 379 (M + +)).

[0271] [Chemical formula]

[0272] (Synthesis Example 6) [Synthesis of Yellow Dye Compound (6)] A yellow dye compound (33.1 g, yield 87.3%) represented by the following formula (6) was obtained in the same manner as in Synthesis Example 5, except that 2-ethylhexanoyl chloride (19.5 g) was used instead of n-octanoyl chloride. The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 379 (M + ))).

[0273] [Chemical formula]

[0274] (Synthesis Example 7) [Synthesis of Yellow Dye Compound (7)] A yellow dye compound (31.0 g, yield 78.9%) represented by the following formula (7) was obtained in the same manner as in Synthesis Example 5, except that n-nonanoyl chloride (21.2 g) was used instead of n-octanoyl chloride. The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 393 (M + ))).

[0275] [Chemical formula]

[0276] (Synthesis Example 8) [Synthesis of Yellow Dye Compound (8)] 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). A mixture of pyridine (9.49 g) and toluene (30 g) was slowly added dropwise to this mixture over 1 hour, and then the temperature was raised to 110 °C and stirred for 1 hour. After the reaction mixture was cooled 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 reaction mixture. After the reaction mixture was heated to 110 °C and stirred for 2 hours, the solvent was distilled off under reduced pressure from the mixture, and methanol (100 g) was added to the residue to precipitate a precipitate. This mixture was filtered, and 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 (36.7 g, yield 74.7%) represented by the following formula (8). The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 491 (M + ))

[0277] [Chemical Formula]

[0278] (Synthesis Example 9) [Synthesis of Yellow Dye Compound (9)] 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 the reaction mixture was cooled to room temperature, 100 g of water was added thereto to precipitate a solid. This mixture was filtered, and 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 (11.9 g, yield 92.8%) represented by the following formula (9). The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 482 (M+)).

[0279] [Chemical Formula]

[0280] (Synthesis Example 10) [Synthesis of Yellow Dye Compound (10)] A yellow dye compound (11.5 g, yield 89.7%) represented by the following formula (10) was obtained in the same manner as in Synthesis Example 9, except that 1-bromo-2-ethylhexane (7.73 g) was used instead of 1-bromooctane. The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 482 (M + ))).

[0281]

Chemical Formula

[0282] (Synthesis Example 11) [Synthesis of Yellow Dye Compound (11)] A yellow dye compound (14.2 g, yield 99.4%) represented by the following formula (11) was obtained in the same manner as in Synthesis Example 9, except that 1-bromododecane (9.98 g) was used instead of 1-bromooctane. The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 538 (M + ))).

[0283]

Chemical Formula

[0284] (Synthesis Example 12) [Synthesis of Yellow Dye Compound (12)] A yellow dye compound (15.5 g, yield 98.5%) represented by the following formula (12) was obtained in the same manner as in Synthesis Example 9, except that 1-bromohexadecane (12.2 g) was used instead of 1-bromooctane. The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 594 (M + ))).

[0285]

Chemical Formula

[0286] (Synthesis Example 13) [Synthesis of Yellow Dye Compound (13)] 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). A mixture of pyridine (9.49 g) and toluene (30 g) was slowly added dropwise to this mixture over 1 hour, and then the temperature was raised to 110 °C and stirred for 1 hour. After cooling the reaction mixture to room temperature, a mixture of 1-aminoanthraquinone (22.3 g) and toluene (30 g) was added thereto. After raising the temperature of the reaction mixture to 110 °C and stirring for 2 hours, it was cooled to room temperature, 10 g of a 24% aqueous sodium hydroxide solution was added, 200 g of water was added, and the organic layer was extracted. This extract was washed with saturated brine, the solvent was distilled off under reduced pressure, and methanol (200 g) was added to the residue to precipitate a precipitate. This mixture was filtered, and 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 41.0 g (yield 88.7%) of the yellow dye compound represented by the following formula (13). The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 462 (M + ))).

[0287] [Chemical formula]

[0288] (Synthesis Example 14) [Synthesis of Yellow Dye Compound (14)] 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). A mixture of pyridine (19.0 g) and toluene (60 g) was slowly added dropwise to this mixture over 1 hour, and then the temperature was raised to 110 °C and stirred for 1 hour. After cooling the reaction mixture to room temperature, a mixture of 1,5-diaminoanthraquinone (23.8 g) and toluene (30 g) was added thereto. After raising the temperature of the reaction mixture to 110 °C and stirring for 2 hours, it was cooled to room temperature, 20 g of a 24% aqueous sodium hydroxide solution was added, and 300 g of water was added to extract the organic layer. After washing this extract with saturated brine, the solvent was distilled off under reduced pressure, and methanol (300 g) was added to the residue to precipitate a precipitate. This mixture was filtered off, and the filtrate was washed with methanol and then with water, and dried at 60 °C until the water content became 1.0 wt% or less to obtain a yellow dye compound (22.6 g, yield 31.6%) represented by the following formula (14). The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 715 (M + ))

[0289] [Chemical formula]

[0290] (Synthesis Example 15) [Synthesis of Yellow Dye Compound (15)] 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 a solid. This mixture was filtered, the filtrate was washed with water, and dried at 60 °C until the water content was 1.0 wt% or less. DMF (60 g), triethylamine (8.1 g), and 2-ethylhexylamine (12.4 g) were added to the obtained solid, the temperature was raised to 90 °C, and the mixture was stirred for 2 hours. The mixture was cooled to room temperature, 20 g of 30% sulfuric acid and then 100 g of water were added to precipitate a solid. This mixture was filtered, and the filtrate was washed with water. Methanol (60 g) was added to this crude product, and the mixture was stirred at 60 °C for 30 minutes. After cooling to room temperature, this mixture was filtered, and 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 (14.4 g, yield 25.9%) represented by the following formula (15). The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 557 (M + ))

[0291] [Chemical formula]

[0292] The dye compounds described in the synthesis examples are shown in Tables 1 to 2.

[0293] [Table 1]

[0294] [Table 2] TIFF0007699406000035.tif146151

[0295] [Dyeing example] Using the compounds described in Tables 1 to 2, polypropylene fabric or polyethylene fabric was dyed by a supercritical carbon dioxide dyeing method.

[0296] (Supercritical Carbon Dioxide Dyeing of Polypropylene Fabric) (Dyeing Example P1) The supercritical carbon dioxide dyeing apparatus used for dyeing is shown in Fig. 1. The dyeing apparatus is composed of a liquid CO2 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 unit (10), a DC motor (11), safety valves (12, 13), stop valves (14 to 18), a needle valve (19), and a heater (20).

[0297] The polypropylene fabric was cut and weighed to about 50 to 70 g, and after being wound around a stainless steel cylinder (21) having punch holes in the order of cotton fabric, polypropylene fabric, and cotton fabric from the inside, it was loosely fixed with cotton thread. The inner cotton fabric is the undercloth, and the outer cotton fabric is the cover cloth.

[0298] The stainless steel cylinder wound with the aforementioned fabric sample (cotton fabric, polypropylene fabric, cotton fabric) was fixed in a pressure-resistant stainless steel tank (22), and the yellow dye compound 1 obtained in Synthesis Example 1 corresponding to 0.3% by mass based on the mass of the polypropylene fabric was wrapped in a paper wipe and placed in the fluid passage above the stainless steel cylinder. The volume of the pressure-resistant stainless steel tank was 2230 cm 3 . All the valves in the dyeing apparatus were closed, and it was heated to 120 °C by the preheater.

[0299] After reaching the dyeing temperature, stop valves (14) and (16) were opened, and 1.13 kg of liquid carbon dioxide was introduced into the pressure-resistant stainless steel tank using a high-pressure pump via the cooling jacket. Then, stop valves (14) and (16) were closed, and it was circulated by an impeller and a magnetic drive unit at the lower part inside the pressure-resistant stainless steel tank. The rotational speed of the magnetic drive unit was 750 rpm, and the circulation direction was from the inside to the outside of the cylinder.

[0300] After the pressure-resistant stainless steel tank reached a predetermined temperature and pressure (120 °C, 25 MPa), the polypropylene cloth was dyed by maintaining these temperature and pressure conditions for 60 minutes. After dyeing, the stop valve (18) was opened and the needle valve was gradually opened to release the carbon dioxide in the pressure-resistant stainless steel tank, reducing the pressure in the pressure-resistant stainless steel tank from 25 MPa to atmospheric pressure. The circulation was continued until the critical pressure of carbon dioxide (about 8 MPa) was reached. Then, the yellow-dyed polypropylene cloth in the pressure-resistant stainless steel tank was taken out.

[0301] (Dyeing Examples P2 to P14) A yellow-dyed polypropylene cloth was obtained by the same dyeing procedure as in Dyeing Example P1, except that the dye compound 1 described in Dyeing Example P1 was changed to the dye compounds described in Tables 1 to 2. The dye compounds used in Dyeing Examples P1 to P14 are shown in Tables 3 to 4.

[0302] [Table 3]

[0303] [Table 4] TIFF0007699406000038.tif145151

[0304] For the polypropylene dyed cloths obtained in Dyeing Examples P1 to P14, dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration fastness test, rubbing fastness test, and fastness test for hot pressing were carried out.

[0305] (1) Dyeability evaluation The dyeability was evaluated by the Total K / S value, K / S value (measured at the maximum wavelength), and the dye residue after dyeing obtained by color measurement of the dyed cloth visually. The color measurement of the dyed cloth was carried out using an integrating sphere spectrophotometer Color-Eye 5 (manufactured by GretagMacbeth) with the dyed cloth pasted on white paper under an observation light source D65 and a 2-degree field of view.

[0306] (2) Light fastness test The light fastness test was conducted by the ultraviolet carbon arc lamp method in accordance with JIS L0842:2004. The outline of the test method is as follows. Using an ultraviolet fade meter U48 (manufactured by Suga Test Instruments Co., Ltd.), after exposing the dyed fabric for 20 hours under the condition of a black panel temperature of 63 ± 3°C, the determination of color change and fading was carried out.

[0307] (3) Sublimation fastness test The sublimation fastness test was conducted by a method in accordance with JIS L0854:2013. The outline of the test method is as follows. The dyed fabric was sandwiched between nylon fabrics, and after holding 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 fabric was carried out.

[0308] (4) Washing fastness test The washing fastness test was conducted by a method in accordance with JIS L0844:2011 (A - 2 type). The outline of the test method is as follows. A multi - woven fabric was attached to the dyed fabric, and washing was carried out for 30 minutes at 50 ± 2°C in the presence of soap. The determination of color change, fading, and contamination of the cotton part and nylon part of the multi - woven fabric was carried out. Also, the determination of contamination of the residual liquid after washing was carried out.

[0309] (5) Perspiration fastness test The perspiration fastness test was conducted by a method in accordance with JIS L0848:2004. The outline of the test method is as follows. A multi - woven fabric was attached to the dyed fabric, and after immersing it in acidic artificial perspiration or alkaline artificial perspiration for 30 minutes, it was held at 37 ± 2°C for 4 hours under a load of 12.5 kPa, then dried at 60°C or lower, and the determination of color change, fading, and contamination of the cotton part and nylon part of the multi - woven fabric was carried out.

[0310] (6) Rubbing fastness test The rubbing fastness test was conducted by a method in accordance with JIS L0849:2013. The outline of the test method is as follows. Using a rubbing fastness tester RT - 300 (manufactured by Daiei Kagaku Seiki Co., Ltd.), the dyed fabric was rubbed 100 times back and forth with a load of 2 N using a dry cotton cloth or a wet cotton cloth, and the determination of coloring of the cotton cloth was carried out.

[0311] (7) Fastness Test for Hot Pressing The fastness test for hot pressing was carried out by a method conforming to JIS L0850:2015 (A-2 type drying). The outline of the test method is as follows. A dyed fabric was placed on a cotton cloth, and after being held for 15 seconds under a load of 4 ± 1 kPa by a heating plate at 150°C, the determination of color change and staining on the cotton cloth was carried out.

[0312] The evaluation results for the dyeing examples of the compound of formula (I) are shown in Table 5, and the evaluation results for the dyeing examples of dye compounds other than the compound of formula (I) are shown in Table 6.

[0313] [Table 5]

[0314] [Table 6]

[0315] Regarding the dyeability of the compound of formula (I), when R1 and R2 used in dyeing examples P1 to P3 are each independently an alkyl group having 4 to 8 carbon atoms which may be branched or an aralkyl group having 7 to 12 carbon atoms, and R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be branched, the dyeability of the compound was good.

[0316] However, the dyeability of dye compounds other than the compound of formula (I) used in dyeing examples P4 to P14 was poor.

[0317] Also, regarding each fastness of the compound of formula (I), when R1 and R2 used in dyeing example P1 or P2 are each independently an alkyl group having 4 to 8 carbon atoms which may be branched, and R3, R4, R5, and R6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be branched, each fastness of the compound was good.

[0318] As described above, the present invention is not limited to the above-described embodiments, and the present invention also includes those obtained by appropriately combining or substituting the configurations of the embodiments.

[0319] Further, based on the knowledge of those skilled in the art, it is also possible to appropriately rearrange the combinations and the order of steps in the embodiments, and to add various modifications such as various design changes to the embodiments. Embodiments with such modifications may also be included in the scope of the present invention.

[0320] The present invention can be used to dye fibers used in clothing, underwear, hats, socks, gloves, sportswear, etc., vehicle interior materials such as seat covers, carpets, curtains, mats, sofa covers, cushion covers, and other interior goods.

Claims

1. A dye for dyeing fibers using supercritical carbon dioxide, comprising a compound of the following general formula (I). 【Chemical 33】 [In formula (I), R 1 and R 2 each independently represents 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, R 3 , R 4 , R 5 , and R 6 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.]

2. 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 12 carbon atoms. The dye according to Claim 1.

3. In the formula (I), R 1 and R 2 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. The dye according to claim 1.

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

5. In the formula (I), R 1 and R 2 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. The dye according to claim 1.

6. 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 12 carbon atoms. The dye according to Claim 1.

7. In the formula (I), R 1 and R 2 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. The dye according to claim 1.

8. In the formula (I), R 1 and R 2 are each independently an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, the dye according to claim 1.

9. In the formula (I), R 1 and R 2 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. The dye according to claim 1.

10. 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 12 carbon atoms. The dye according to Claim 1.

11. In the formula (I), R 1 and R 2 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. The dye according to claim 1.

12. In the formula (I), R 1 and R 2 are each independently an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms. The dye according to claim 1.

13. 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). 【Chemical Formula 34】

14. The dye according to Claim 1, which is a dye for dyeing polyolefin fibers.

15. A method for dyeing fibers using supercritical carbon dioxide, comprising a step of dyeing the fibers in the presence of supercritical carbon dioxide using the dye according to Claims 1 to 14.

16. The dyeing method according to Claim 15, wherein the dyeing step is carried out at a pressure of 31 °C or higher and 7.4 MPa or higher.

17. The dyeing method according to Claim 15, wherein the concentration of the dye with respect to the fibers is in the range of 0.1 to 6.0% o.m.f. (on the mass of fiber).

18. Fibers dyed by the dyeing method according to Claim 15.

19. A compound of the following general formula (I). 【Chemical Formula 35】 [In formula (I), R1 represents 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, R2 represents an alkyl group having 6 to 14 carbon atoms, R3, R4, R5, and R6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.]

20. In the formula (I), R1 is an aralkyl group having 7 to 12 carbon atoms, R2 is an alkyl group having 6 to 14 carbon atoms, The compound according to Claim 19.

21. In the formula (I), R1 is 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, R2 is an alkyl group having 6 to 12 carbon atoms, The compound according to claim 19.

22. In the formula (I), R1 is an aralkyl group having 7 to 12 carbon atoms, R2 is an alkyl group having 6 to 12 carbon atoms, The compound according to claim 19.

23. In the formula (I), R1 is 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, R2 is an alkyl group having 6 to 12 carbon atoms, The compound according to claim 19.

24. In the formula (I), R1 is an aralkyl group having 7 to 9 carbon atoms, R2 is an alkyl group having 6 to 12 carbon atoms, The compound according to claim 19.

25. In the formula (I), R1 is 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, R2 is an alkyl group having 6 to 10 carbon atoms, The compound according to claim 19.

26. In the formula (I), R1 is an aralkyl group having 7 to 9 carbon atoms, R2 is an alkyl group having 6 to 10 carbon atoms, The compound according to claim 19.

27. In the formula (I), R1 is 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, R2 is an alkyl group having 6 to 8 carbon atoms, The compound according to claim 19.

28. The compound according to claim 19, wherein the compound of the general formula (I) is represented by the following formula (4). 【Chemical 36】

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