Dye for dying 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

Dyes for dyeing with supercritical carbon dioxide

[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 compounds.

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

[0003] On the other hand, polyolefin resins are polymeric compounds in which both the main chain and side chains are composed of hydrocarbons, and for these reasons, they have low affinity and compatibility with conventional dye compounds and do not have functional groups that are effective in chemical reactions, making it extremely difficult to dye them with high concentrations and high fastness.

[0004] For this reason, most of the colored polyolefin resins currently on the market are made by adding colored pigments during the production stage of polymer pellets, etc., and then spinning and molding them into the desired shape.

[0005] This coloring method requires that the color be determined at an early stage of the resin product manufacturing process, and to be profitable, a certain amount of each color must be produced, which limits the freedom of color selection.

[0006] Furthermore, when changing the color of a resin product, a process is required to replace the colored resin of the previous color remaining in the resin product manufacturing equipment with colored resin of the next color, which generates a large amount of waste resin and causes problems such as wasting time and energy.

[0007] As described in Yamamoto Hiroshi, Sen'i Gakkaishi Journal, 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 applications of polypropylene resin and polyethylene resin as synthetic fibers are very limited.

[0009] The reason for this is thought to be that, as mentioned above, it is extremely difficult to dye polypropylene resin fibers and polyethylene resin fibers with high concentration and high fastness, and the only effective coloring method, the solution coloring method using colored pigments, inevitably requires a large single yarn fineness and limits the freedom of color selection.

[0010] Up until now, attempts have been made to change the molecular structure of dyes in order to dye polyolefin-based resin fibers in an aqueous system, and dyes for dyeing polyolefin-based resin fibers have been proposed in Japanese Patent Publication Nos. 38-10741, 40-1277, and 41-3515, British Patent No. 872,882, U.S. Patent No. 3,536,735, and Japanese Patent Laid-Open No. 2019-203223.

[0011] Japanese Patent Publication No. 1963-10741 describes examples of producing 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 dye, and examples of dyeing polypropylene resin fibers with the dyes.

[0012] However, it is difficult to achieve high-concentration dyeing of polyolefin resin fibers with these anthraquinone red dyes or anthraquinone purple dyes. Furthermore, with regard to the form of the dyes used for dyeing, there is a description that these anthraquinone red dyes are dissolved in organic solvents such as alcohol or acetone before use, which is hardly environmentally friendly. Furthermore, there is no description of yellow dyes.

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

[0014] However, it is difficult to dye polyolefin resin fibers at high concentration with these anthraquinone blue dyes, and there is no specific description about the color fastness of the dyed products obtained. Furthermore, with regard to the form of the dye when used for dyeing, there is a description that these anthraquinone blue dyes are used after being dissolved in an organic solvent such as alcohol or acetone, which is hardly environmentally friendly. In addition, there is no description about yellow dyes.

[0015] Japanese Patent Publication No. 41-3515 describes an example of producing a blue dye 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 also describes an example of dyeing polyolefin resin fibers with the dye.

[0016] However, it is difficult to dye polyolefin resin fibers at high concentration with these anthraquinone blue dyes, and there is no specific description of the color fastness of the dyed products obtained. Furthermore, with regard to the form of the dye when used for dyeing, there is a description that the dye should be dissolved in an organic solvent such as alcohol or acetone before use, which is hardly environmentally friendly. In addition, there is no description of yellow dyes.

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

[0018] However, it is difficult to dye polyolefin resin fibers at high density with these anthraquinone blue dyes, and there is no specific description of the color fastness of the dyed products obtained.In addition, there is no description of yellow dyes.

[0019] U.S. Pat. No. 3,536,735 describes examples of producing red dyes in which phenoxy groups having two substituents selected from a sec-butyl group, a sec-pentyl group, and a tert-pentyl group are introduced into an anthraquinone dye, and also describes examples of dyeing polypropylene resin fibers with the dyes.

[0020] However, it is difficult to dye polyolefin resin fibers at high concentration with these anthraquinone red dyes, and there is no specific description of the color fastness of the dyed products obtained. Furthermore, with regard to the form of the dye when used for dyeing, there is a description that the dye should be dissolved in dimethylformamide, an organic solvent, before use, which is hardly environmentally friendly. In addition, there is no description of yellow dyes.

[0021] JP 2019-203223 A describes a dyeing example in which polypropylene fibers are dyed in water using a disperse dye composition containing an anthraquinone yellow dye, an anthraquinone red dye, or an anthraquinone blue dye having a long-chain alkyl group.

[0022] However, it is difficult to dye polypropylene fibers to a high density with the anthraquinone yellow dyes having a long chain alkyl group.

[0023] JP-A-55-152869 describes examples of producing monoazo dyes having long-chain alkyl groups and examples of dyeing fine denier polyester fibers using the dyes. However, it does not describe examples of dyeing polyolefin fibers using the dyes. In addition, it does not describe any yellow dyes.

[0024] Furthermore, various studies have been conducted on modifying polyolefin resin fibers in order to improve their dyeability.

[0025] Various modification techniques are known, such as blending dyeable resin components such as polyester, copolymerization with vinyl monomers having dyeable groups, and blending dye accelerators such as metal stearates.

[0026] Although the dyeability of these modified polyolefin resin fibers has been improved, the strength of the yarn is reduced by the dyeing treatment, resulting in a problem of insufficient strength when used in clothing and the like.

[0027] Incidentally, Japanese Patent No. 3253649 describes a dyeing method that replaces aqueous dyeing, in which supercritical carbon dioxide is used as a dyeing medium to dye hydrophobic fiber materials with various dyes.

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

[0029] Japanese Patent No. 6721172 describes the use of supercritical carbon dioxide as a dyeing medium to dye polypropylene fibers, which are polyolefin fibers, with an anthraquinone blue dye, an anthraquinone yellow dye, an anthraquinone red dye, or a mixture of these dyes.

[0030] However, it is difficult to dye polypropylene fibers to a high density with the anthraquinone yellow dyes described.

[0031] If a method for dyeing polypropylene resin fibers and polyethylene resin fibers with high density and high fastness can be put into practical use, it will become possible to color inexpensive, uncolored regular yarns with small single yarn fineness without any color restrictions, which is expected to lead to new applications in fields where high design quality is required, such as clothing and vehicle interior materials, where polypropylene resin fibers and polyethylene resin fibers have not been used until now.

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

[0033]

[0034] [In formula (I), R １ and R 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; 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.

[0035] The supercritical carbon dioxide dyeing equipment used for dyeing is shown. Detailed Description of the Invention

[0036] Therefore, an object of the present invention is to provide a dye for dyeing fibers using supercritical carbon dioxide, which can dye fibers a high-concentration yellow and give dyed products excellent color fastness to light, sublimation, washing, etc.; a method for dyeing fibers using supercritical carbon dioxide; fibers dyed by the dyeing method; and a compound.

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

[0038]

[0039] [In formula (I), R １ and R 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; 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.

[0040] The present invention also provides a method for dyeing fibers using supercritical carbon dioxide, which comprises the step of dyeing fibers using the dye of the present invention in the presence of supercritical carbon dioxide.

[0041] The present invention also provides a fiber dyed by a dyeing method comprising a step of dyeing a fiber with the dye of the present invention in the presence of supercritical carbon dioxide.

[0042] The present invention also provides a compound represented by the following general formula (I):

[0043]

[0044] [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 ６each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0045] The dye of the present invention can dye fibers in a high-concentration yellow in the presence of supercritical carbon dioxide, and the dyed products have excellent color fastness to light, sublimation, washing, etc.

[0046] The present inventors have discovered that dyes containing the following specific compounds have improved affinity for fibers and dye fibers to a rich yellow color in the presence of supercritical carbon dioxide, and have completed the present invention.

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

[0048]

[0049] [In formula (I), R 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.

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

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

[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, a 4-methylphenethyl group, a 4-ethylbenzyl group, a 4-ethylphenethyl group, a 4-n-propylbenzyl group, a 4-n-propylphenethyl group, a 4-n-butylbenzyl group, a 4-n-butylphenethyl group, a 4-isopropylbenzyl group, a 4-tert-butylbenzyl group, a 4-tert-butylphenethyl group, etc. Among these, an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms is preferred, an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms is preferred, and an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms is more preferred.

[0053] In the formula (I), examples of the alkyl group having 1 to 4 carbon atoms include a linear or branched alkyl group having 1 to 4 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, etc. The alkyl group having 1 to 4 carbon atoms is preferably an alkyl group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 or 2 carbon atoms, and more preferably an alkyl group having 1 carbon atom.

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

[0055]

[0056] [In formula (I), R 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; R３ , R ４ , R ５ , and R ６ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0057] In the formula (I), R and R ２ are each independently preferably an optionally branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; are preferably an optionally branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; and are preferably an optionally branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0058] In addition, in the formula (I), R and R ２ are each independently preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; and preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0059] In addition, in the formula (I), R and R ２are 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; 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; 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 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 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0060] In addition, in the formula (I), R and R ２ 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; 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; 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 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.

[0061] In addition, in the formula (I), R ３ , R ４ , R ５ , and R ６ are preferably each independently a hydrogen atom or an optionally branched alkyl group having 1 to 4 carbon atoms.

[0062] In addition, in the formula (I), R ３ , R ４ , R ５ , and R ６are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0063] In addition, in the formula (I), R ３ , R ４ , R ５ , and R ６ are each independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0064] In addition, in the formula (I), R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0065] In addition, in the formula (I), R and R ２ 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 or 2 carbon atoms.

[0066] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0067] In addition, in the formula (I), R and R ２ 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] In addition, in the formula (I), R and R ２ 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 or 2 carbon atoms.

[0069] In addition, in the formula (I), R and R ２It is more preferable that each of the groups independently represents an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0070] In addition, in the formula (I), R 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.

[0071] In addition, in the formula (I), R 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 or 2 carbon atoms.

[0072] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0073] In addition, in the formula (I), R and R ２ and more preferably each independently represent 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] In addition, in the formula (I), R 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.

[0075] In addition, in the formula (I), R 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 or 2 carbon atoms.

[0076] In addition, in the formula (I), R and R ２It is more preferable that each of the groups independently represents an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0077] In addition, in the formula (I), R and R ２ 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] In addition, in the formula (I), R and R ２ 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 or 2 carbon atoms.

[0079] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0080] In addition, in the formula (I), R 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.

[0081] In addition, in the formula (I), R 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 or 2 carbon atoms.

[0082] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0083] In addition, in the formula (I), R and R ２are 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] In addition, in the formula (I), R 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.

[0085] In addition, in the formula (I), R 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 10 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.

[0086] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0087] In addition, in the formula (I), R and R ２ 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] In addition, in the formula (I), R and R ２ 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 or 2 carbon atoms.

[0089] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0090] In addition, in the formula (I), R and R ２are 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] In addition, in the formula (I), R 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 or 2 carbon atoms.

[0092] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0093] In addition, in the formula (I), R and R ２ 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] In addition, in the formula (I), R and R ２ 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] In addition, in the formula (I), R and R ２ 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 or 2 carbon atoms.

[0096] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0097] In addition, in the formula (I), R and R ２are 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] In addition, in the formula (I), R and R ２ 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 or 2 carbon atoms.

[0099] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0100] In addition, in the formula (I), R and R ２ 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] In addition, in the formula (I), R and R ２ 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 or 2 carbon atoms.

[0102] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0103] In addition, in the formula (I), R and R ２ 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] In addition, in the formula (I), R and R ２are 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 or 2 carbon atoms.

[0105] In addition, in the formula (I), R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0106] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0107] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0108] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0109] In addition, in the formula (I), R and R ２each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0110] In addition, in the formula (I), R and R ２ each independently represents 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 or 2 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0111] In addition, in the formula (I), R and R ２ each independently represents an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0112] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0113] In addition, in the formula (I), R and R ２each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0114] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0115] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0116] In addition, in the formula (I), R and R ２ each independently represents 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 or 2 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0117] In addition, in the formula (I), R and R ２each independently represents an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0118] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0119] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0120] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0121] In addition, in the formula (I), R and R ２each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0122] In addition, in the formula (I), R and R ２ each independently represents 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 or 2 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0123] In addition, in the formula (I), R and R ２ each independently represents an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0124] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0125] In addition, in the formula (I), R and R ２each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0126] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0127] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0128] In addition, in the formula (I), R and R ２ each independently represents 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 or 2 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0129] In addition, in the formula (I), R and R ２each independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0130] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0131] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0132] In addition, in the formula (I), R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0133] In addition, in the formula (I), R and R ２ each independently represents 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; R３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0134] In addition, in the formula (I), R and R ２ each independently represents an alkyl group having 4 to 6 carbon atoms; R ３ , R ４ and R ６ represents a hydrogen atom, R ５ is preferably an alkyl group having 1 to 4 carbon atoms.

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

[0136]

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

[0138] In the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ are each independently preferably an optionally branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; are preferably an optionally branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; and are preferably an optionally branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0139] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２are each independently preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; and preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0140] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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; 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; 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 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 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.

[0141] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２are 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; 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; 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 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] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., ３ , R ４ , R ５ , and R ６ are preferably each independently a hydrogen atom or an optionally branched alkyl group having 1 to 4 carbon atoms.

[0143] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., ３ , R ４ , R ５ , and R ６ are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0144] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., ３ , R ４ , R ５ , and R ６ are each independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0145] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., ３ , R ４ , R ５ , and R ６It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0146] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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 or 2 carbon atoms.

[0147] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0148] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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.

[0149] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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 or 2 carbon atoms.

[0150] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0151] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２are 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] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R 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 or 2 carbon atoms.

[0153] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0154] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ and more preferably each independently represent 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] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R 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.

[0156] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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 or 2 carbon atoms.

[0157] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0158] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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 or 2 carbon atoms.

[0160] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0161] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R 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.

[0162] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R 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 or 2 carbon atoms.

[0163] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0164] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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.

[0165] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R 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.

[0166] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R 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 10 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.

[0167] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0168] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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.

[0169] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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 or 2 carbon atoms.

[0170] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0171] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R 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.

[0172] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R 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 or 2 carbon atoms.

[0173] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0174] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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.

[0175] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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.

[0176] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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 or 2 carbon atoms.

[0177] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

[0178] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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.

[0179] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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 or 2 carbon atoms.

[0180] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

[0181] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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.

[0182] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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 or 2 carbon atoms.

[0183] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0184] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ 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.

[0185] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., ２ 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 or 2 carbon atoms.

[0186] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., ２ It is more preferable that each of the groups independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.

[0187] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0188] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0189] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0190] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0191] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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 or 2 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0192] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0193] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0194] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0195] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0196] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0197] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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 or 2 carbon atoms; R ３ , R ４ , R ５ , and R ６It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0198] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0199] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0200] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0201] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0202] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0203] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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 or 2 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0204] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0205] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0206] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0207] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0208] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0209] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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 or 2 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0210] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0211] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0212] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６It is more preferable that each of the groups independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0213] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

[0214] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents 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; R ３ , R ４ , R ５ , and R ６ It is more preferable that each independently represents a hydrogen atom or an alkyl group having one carbon atom.

[0215] In addition, in the formula (I) of the dye, from the viewpoint of color density, light fastness, sublimation fastness, etc., R and R ２ each independently represents an alkyl group having 4 to 6 carbon atoms; R ３ , R ４ and R ６ represents a hydrogen atom, R ５ is preferably an alkyl group having 1 to 4 carbon atoms.

[0216] The compound of formula (I) of the dye is preferably the following compound, more preferably the compound of formula (1) or (2), from the viewpoints of color density, light fastness, sublimation fastness, etc.

[0217]

[0218] <Method for producing the compound of formula (I)> A method for producing the compound represented by formula (I) will be described.

[0219]

[0220] The compound represented by formula (I) is an aniline derivative represented by formula (i-A) (wherein R 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 and each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.) and then subjecting it to a condensation reaction with malononitrile.

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

[0222] The reaction temperature for the 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 compound of formula (i-A) in DMF and an alcohol, and the mixture is stirred in the presence of an organic base as a catalyst at a temperature ranging from 10 to 85°C, preferably from 40 to 85°C, to obtain the compound represented by formula (I). Examples of the alcohols used include methanol and ethanol. Examples of the organic bases used include pyridine and triethylamine.

[0224] (iii) Method for Producing Compound of Formula (i-A) The compound of formula (i-A), which is a starting material, can be produced as follows.

[0225]

[0226] Using DMF as a solvent, the compound represented by formula (i-A1) was reacted with R １ -X and R ２ -X(R １ and R ２each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and X represents a halogen atom), to obtain 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 additives such as auxiliary colorants, dispersants, fillers, stabilizers, plasticizers, crystal nucleating agents, modifiers, foaming agents, ultraviolet absorbers, light stabilizers, antioxidants, antibacterial agents, antifungal agents, antistatic agents, flame retardants, inorganic fillers, and elastomers for improving impact resistance.

[0229] <Fibers> Examples of fibers to be dyed with the dye composition of the present invention include polyester fibers, polyolefin fibers, and acrylic fibers, with polyolefin fibers being preferred. Furthermore, polyolefin fibers are more preferred as fibers to be dyed with the dye of the present invention.

[0230] Examples of the polyolefin fibers include fibers formed from polymers selected from homopolymers of α-olefins such as propylene, ethylene, 1-butene, 3-methyl-1-butene, 4-methyl-1-pentene, and 1-octene, copolymers of these α-olefins, and copolymers of these α-olefins with other unsaturated monomers copolymerizable therewith. Examples of the copolymers include block copolymers, random copolymers, and graft copolymers. Specific examples of the polymers 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; and poly-4-methyl-1-pentene.

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

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

[0233] The polyolefin fiber may be in any form, 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 form.

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

[0235] <Method for dyeing fibers using supercritical carbon dioxide> The present invention is a method for dyeing fibers using supercritical carbon dioxide, which comprises a step of dyeing fibers using the dye of the present invention in the presence of supercritical carbon dioxide. In the method, supercritical carbon dioxide is used as a dyeing medium.

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

[0237] Furthermore, when fibers or the like using polyolefin resins are dyed with the dye of the present invention, the dye medium, dye, and object to be dyed have high affinity with each other because supercritical carbon dioxide is lipophilic and both the dye of the present invention and the polyolefin resin are lipophilic, resulting in high-quality dyed objects.

[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 dyeing pressure must be equal to or higher than the critical point (7.4 MPa at 31°C) of carbon dioxide, which is the dyeing medium.

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

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

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

[0242] In the dyeing process, the concentration of the dye relative to the fiber depends on the type and processing state of the fiber to be dyed. When the fiber to be dyed is fibrous, the concentration of the dye relative 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 liquor ratio (mass ratio of material to be dyed to carbon dioxide) depends on the type of material to be dyed and its processing state. The liquor ratio is usually 1:2 to 1:100, preferably 1:5 to 1:75. When the material to be dyed is a cloth wrapped in a suitable cheesecloth, the liquor ratio in the dyeing method of the present invention 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. The dyed fiber is dyed to a high concentration, particularly a high concentration yellow, and has excellent color fastness to light, sublimation, washing, etc. Applications of the fiber include, for example, clothing such as clothes, underwear, hats, socks, gloves, and sportswear; vehicle interior materials such as seats; and interior goods such as carpets, curtains, mats, sofa covers, and cushion covers.

[0245] The present invention will be explained in more detail below by way of examples, but the aspects of the present invention are not limited to these examples.

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

[0247]

[0248] (Step 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]

[0250] (Step 2) The reaction mixture of N,N-dioctyl-3-methylaniline obtained in Step 1 was cooled to 5°C. To this mixture, phosphorus oxychloride (23.0 g) was added dropwise over 1 hour at a temperature of 5 to 10°C, and pyridine (11.9 g) was then added dropwise at a temperature of 5 to 10°C. The mixture was then heated to 40 to 45°C and stirred for 1 hour. After cooling the reaction mixture to 10°C, methanol (40 g) was added dropwise at a temperature of 10 to 20°C, and anhydrous sodium acetate (35 g) was added at a temperature of 10 to 20°C. To this mixture, a solution of malononitrile (6.61 g) dissolved in methanol (10 g) was added dropwise at a temperature of 10 to 20°C. The mixture was heated to 25 to 30°C and stirred for 30 minutes, and then heated to 85°C and stirred for 4 hours. After cooling the reaction mixture to room temperature, water (200 g) and ethyl acetate (200 g) were added to extract the organic layer, which was then washed with saturated saline, and the solvent was distilled off under reduced pressure. Methanol (80 g) was added to the crude product, which was cooled to 0-5°C, and 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 yellow dye compound was analyzed by LCMS (m / z 408 (M ＋ )) confirmed its structure.

[0251]

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

[0253]

[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]

[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 yellow dye compound was analyzed by LCMS (m / z 352 (M ＋ )) confirmed its structure.

[0257]

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

[0259]

[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]

[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 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]

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

[0265]

[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]

[0268] (Step 2) A yellow dye compound (21.2 g, yield 57.1%) represented by the following formula (4) 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]

[0270] Synthesis Example 5 Synthesis of Yellow Dye Compound (5) After 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), the mixture was heated to 110°C and stirred for 1 hour. After cooling the mixture to room temperature, methanol (150 g) was added to precipitate the compound. The mixture was filtered, and the filtered product 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 (31.8 g, yield 83.9%) represented by the following formula (5). The yellow dye compound was analyzed by LCMS (m / z 379 (M ＋ )) confirmed its structure.

[0271]

[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 yellow dye compound was analyzed by LCMS (m / z 379 (M ＋)) confirmed its structure.

[0273]

[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 yellow dye compound was analyzed by LCMS (m / z 393 (M ＋ )) confirmed its structure.

[0275]

[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 mixture was heated 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. The reaction mixture was heated to 110°C and stirred for 2 hours, after which the solvent was distilled off from the mixture under reduced pressure, and methanol (100 g) was added to the residue to precipitate a precipitate. This mixture was filtered, and the filtered product was washed with methanol and then with water, and dried at 60°C until the moisture 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 yellow dye compound was identified by LCMS analysis (m / z 491 (M ＋ )) confirmed its structure.

[0277]

[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 to precipitate a solid. This mixture was filtered, and the precipitate was washed with methanol and then with water. It was then dried at 60°C until the water content was 1.0 wt% or less, yielding a yellow dye compound represented by the following formula (9) (11.9 g, yield 92.8%). The structure of the yellow dye compound was confirmed by LCMS analysis (m / z 482 (M+)).

[0279]

[0280] Synthesis Example 10 Synthesis of Yellow Dye Compound (10) The procedure of Synthesis Example 9 was repeated except for using 1-bromo-2-ethylhexane (7.73 g) instead of 1-bromooctane to obtain a yellow dye compound (11.5 g, yield 89.7%) represented by the following formula (10). The yellow dye compound was analyzed by LCMS (m / z 482 (M ＋ )) confirmed its structure.

[0281]

[0282] Synthesis Example 11 Synthesis of Yellow Dye Compound (11) The procedure of Synthesis Example 9 was repeated except for using 1-bromododecane (9.98 g) instead of 1-bromooctane to obtain a yellow dye compound (14.2 g, yield 99.4%) represented by the following formula (11). The yellow dye compound was analyzed by LCMS (m / z 538 (M ＋ )) confirmed its structure.

[0283]

[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 yellow dye compound was analyzed by LCMS (m / z 594 (M＋ )) confirmed its structure.

[0285]

[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 mixture was heated to 110°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and then a mixture of 1-aminoanthraquinone (22.3 g) and toluene (30 g) was added thereto. The reaction mixture was heated to 110°C and stirred for 2 hours, then cooled to room temperature, and 10 g of a 24% aqueous sodium hydroxide solution was added, followed by the addition of 200 g of water to extract the organic layer. This extract was washed with saturated saline, and the solvent was then distilled off under reduced pressure. 200 g of methanol was added to the residue to precipitate a precipitate. This mixture was filtered, and the filtered product was washed with methanol and then with water, and dried at 60°C until the moisture content was 1.0 wt% or less to obtain a yellow dye compound (41.0 g, yield 88.7%) represented by the following formula (13). The yellow dye compound was identified by LCMS analysis (m / z 462 (M ＋ )) confirmed its structure.

[0287]

[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 mixture was heated to 110°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and then a mixture of 1,5-diaminoanthraquinone (23.8 g) and toluene (30 g) was added thereto. The reaction mixture was heated to 110°C and stirred for 2 hours, then cooled to room temperature, and 20 g of a 24% aqueous sodium hydroxide solution was added, followed by 300 g of water to extract the organic layer. This extract was washed with saturated saline, and the solvent was then distilled off under reduced pressure. 300 g of methanol was added to the residue to precipitate a precipitate. This mixture was filtered, and the filtered product was washed with methanol and then with water, and dried at 60°C until the moisture content was 1.0 wt% or less to obtain a yellow dye compound (22.6 g, yield 31.6%) represented by the following formula (14). The yellow dye compound was identified by LCMS analysis (m / z 715 (M ＋ )) confirmed its structure.

[0289]

[0290] Synthesis Example 15 Synthesis of Yellow Dye Compound (15) A mixture of 1-aminoanthraquinone (22.3 g), cyanuric acid 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. This mixture was filtered, and the filtered product was washed with water and dried at 60°C until the moisture content was 1.0 wt% or less. DMF (60 g), triethylamine (8.1 g), and 2-ethylhexylamine (12.4 g) were added to the resulting solid, and the mixture was heated to 90°C and stirred for 2 hours. The mixture was cooled to room temperature, and 20 g of 30% sulfuric acid was added, followed by 100 g of water, to precipitate. This mixture was filtered, and the filtered product 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, the mixture was filtered, and the filtered product was washed with methanol and then with water, and dried at 60°C until the moisture 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 yellow dye compound was identified by LCMS analysis (m / z 557 (M ＋ )) confirmed its structure.

[0291]

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

[0293]

[0294]

[0295] Dyeing Examples Using the compounds shown in Tables 1 and 2, polypropylene fabric or polyethylene fabric was dyed by supercritical carbon dioxide dyeing.

[0296] (Supercritical carbon dioxide dyeing of polypropylene fabric) (Dyeing example P1) The supercritical carbon dioxide dyeing apparatus used for dyeing is shown in Figure 1. The dyeing apparatus uses liquid CO ２The system is composed of a 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] Polypropylene cloth was cut into pieces of approximately 50 to 70 g, weighed, and wound around a stainless steel cylinder (21) with punched holes in the order of cotton cloth, polypropylene cloth, and cotton cloth from the inside out, and then loosely secured with cotton thread. The inner cotton cloth was the undercloth, and the outer cotton cloth was the cover cloth.

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

[0299] After the dyeing temperature was reached, 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 connected to a cooling jacket. Thereafter, stop valves (14) and (16) were closed, and the liquid was circulated by the impeller and magnetic drive unit at the bottom of the pressure-resistant stainless steel tank. The rotation 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 the specified temperature and pressure (120°C, 25 MPa), these temperature and pressure conditions were maintained for 60 minutes to dye the polypropylene fabric. After dyeing, the stop valve (18) was opened and the needle valve was gradually opened to release the carbon dioxide from the pressure-resistant stainless steel tank, lowering the pressure in the pressure-resistant stainless steel tank from 25 MPa to atmospheric pressure. Circulation continued until the critical pressure of carbon dioxide (approximately 8 MPa) was reached. The yellow-dyed polypropylene fabric was then removed from the pressure-resistant stainless steel tank.

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

[0302]

[0303]

[0304] The dyed polypropylene fabrics obtained in Dyeing Examples P1 to P14 were subjected to dyeability evaluation, a light fastness test, a sublimation fastness test, a washing fastness test, a sweat fastness test, a rub fastness test, and a hot pressing fastness test.

[0305] (1) Dyeability Evaluation Dyeability was evaluated by measuring the color of the dyed fabric to determine the total K / S value and K / S value (measured at the maximum wavelength), and by visual inspection of the dye residue after dyeing. The color of the dyed fabric was measured using an integrating sphere spectrophotometer, Color-Eye 5 (manufactured by GretagMacbeth), with the dyed fabric glued onto white paper, under a D65 light source and a 2-degree visual field.

[0306] (2) Lightfastness Test The lightfastness test was carried out using an 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.), the dyed fabric was exposed to light for 20 hours at a black panel temperature of 63±3°C, and then the discoloration was judged.

[0307] (3) Sublimation Fastness Test The sublimation fastness test was performed according to JIS L0854: 2013. The outline of the test method is as follows: The dyed fabric was sandwiched between nylon fabrics and held at 120±2°C for 80 minutes under a load of 12.5 kPa, and then the discoloration and staining of the nylon fabric were evaluated.

[0308] (4) Washing Fastness Test The washing fastness test was conducted according to JIS L0844:2011 (A-2). The outline of the test method is as follows. A multi-woven fabric was attached to the dyed fabric, and the fabric was washed for 30 minutes in the presence of soap at 50±2°C, and the discoloration and staining of the cotton and nylon parts of the multi-woven fabric were evaluated. The staining of the residual liquid after washing was also evaluated.

[0309] (5) Sweat Fastness Test The sweat fastness test was conducted according to JIS L0848:2004. The outline of the test method is as follows: A multi-woven fabric was attached to the dyed fabric, and the fabric was immersed in acidic artificial sweat or alkaline artificial sweat for 30 minutes, then held at 37±2°C for 4 hours under a load of 12.5 kPa, and then dried at 60°C or below, and the discoloration and staining of the cotton and nylon parts of the multi-woven fabric were evaluated.

[0310] (6) Rubbing Fastness Test The rubbing fastness test was carried out 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 Scientific Instruments Co., Ltd.), the dyed fabric was rubbed back and forth 100 times with a dry cotton fabric or a wet cotton fabric under a load of 2 N, and the coloring of the cotton fabric was judged.

[0311] (7) Test of fastness to hot pressing The test of fastness to hot pressing was carried out according to JIS L0850:2015 (A-2, dry). The outline of the test method is as follows: The dyed fabric was placed on top of the cotton fabric, and the fabric was held for 15 seconds under a load of 4±1 kPa on a heating plate at 150°C, and then the discoloration and staining of the cotton fabric were evaluated.

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

[0313]

[0314]

[0315] Regarding the dyeing properties of the compound of formula (I), the R and R used in dyeing examples P1 to P3 ２are each independently an optionally branched alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 12 carbon atoms, and R ３ , R ４ , R ５ , and R ６ The dyeing properties of the compound in which each of the groups is independently a hydrogen atom or an optionally branched alkyl group having 1 to 4 carbon atoms were good.

[0316] However, the dyeing properties of the dye compounds other than the compound of formula (I) used in Dyeing Examples P4 to P14 were poor.

[0317] In addition, for each fastness of the compound of formula (I), the R and R used in dyeing example P1 or P2 were ２ are each independently an optionally branched alkyl group having 4 to 8 carbon atoms, and R ３ , R ４ , R ５ , and R ６ are each independently a hydrogen atom or an optionally branched alkyl group having 1 to 4 carbon atoms, and the fastness of each of the compounds was good.

[0318] As described above, the present invention is not limited to the above-described embodiments, and suitable combinations or substitutions of the configurations of the embodiments are also included in the present invention.

[0319] Furthermore, it is possible to appropriately rearrange the combinations and order of steps in the embodiments based on the knowledge of a person skilled in the art, and to make modifications to the embodiments such as various design changes, and embodiments to which such modifications have been made may also be included within the scope of the present invention.

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

Claims

1. A dye for dyeing fibers using supercritical carbon dioxide, comprising a compound represented by 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. The dye according to claim 1, wherein in formula (I), R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

3. In the formula (I), R 1 and R 2 The dye according to claim 1 , wherein each of the groups independently represents 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.

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

5. In the formula (I), R 1 and R 2 The dye according to claim 1 , wherein each of the groups independently represents 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.

6. The dye according to claim 1, wherein in formula (I), R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.

7. In the formula (I), R 1 and R 2 The dye according to claim 1 , wherein each of the groups independently represents 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.

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

9. In the formula (I), R 1 and R 2 The dye according to claim 1 , wherein each of the groups independently represents 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.

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

11. In the formula (I), R 1 and R 2 The dye according to claim 1 , wherein each of the groups is 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.

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

13. 2. 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 34】 14. The dye of claim 1, which is a dye for dyeing polyolefin fibers.

15. A method for dyeing a fiber using supercritical carbon dioxide, comprising the steps of: A process comprising the step of dyeing a fiber with a dye according to any one of claims 1 to 14 in the presence of supercritical carbon dioxide.

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

17. 16. The method of claim 15, wherein the concentration of the dye on the fiber ranges from 0.1 to 6.0% o.m.f. (on the mass of fiber).

18. A fiber dyed by the dyeing method described in claim 15.

19. A compound represented by the following general formula (I): 【Chemistry 35】 [In formula (I), R 1 represents an aralkyl group having 7 to 12 carbon atoms or an aralkyl group having 7 to 12 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms; R 2 represents an alkyl group having 6 to 14 carbon atoms; R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

20. In the formula (I), R 1 is an aralkyl group having 7 to 12 carbon atoms, R 2 is an alkyl group having 6 to 14 carbon atoms; 20. The compound of claim 19.

21. In the formula (I), R 1 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; R 2 is an alkyl group having 6 to 12 carbon atoms; 20. The compound of claim 19.

22. In the formula (I), R 1 is an aralkyl group having 7 to 12 carbon atoms, R 2 is an alkyl group having 6 to 12 carbon atoms; 20. The compound of claim 19.

23. In the formula (I), R 1 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; R 2 is an alkyl group having 6 to 12 carbon atoms; 20. The compound of claim 19.

24. In the formula (I), R 1 is an aralkyl group having 7 to 9 carbon atoms, R 2 is an alkyl group having 6 to 12 carbon atoms; 20. The compound of claim 19.

25. In the formula (I), R 1 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; R 2 is an alkyl group having 6 to 10 carbon atoms; 20. The compound of claim 19.

26. In the formula (I), R 1 is an aralkyl group having 7 to 9 carbon atoms, R 2 is an alkyl group having 6 to 10 carbon atoms; 20. The compound of claim 19.

27. ​​In the formula (I), R 1 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; R 2 is an alkyl group having 6 to 8 carbon atoms; 20. The compound of claim 19.

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

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