JP2024018588A - Coloring composition, method for producing colored material, colored material, and kit - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a coloring composition that is used in coloring fabric including polyamide fibers, to produce a colored material with a good cyan color as well as good resistance to both perspiration and light.

SOLUTION: The present invention provides a coloring composition that is used in coloring fabric including polyamide fibers. The coloring composition comprises a colorant and water. The colorant comprises at least one selected from the group consisting of a compound represented by general formula (IA), a compound represented by general formula (IB), and a compound represented by general formula (IC).

SELECTED DRAWING: None

COPYRIGHT: (C)2024,JPO&INPIT

Description

The present invention relates to a colored composition, a method for producing a colored product, a colored product, and a kit.

Since azo dyes often have various visible light absorptions, they have been used in various fields. For example, azo dyes are sometimes used to color fabrics.
More specifically, Patent Document 1 discloses an aqueous coloring composition for textile printing containing an azo dye, which can form images with high color density and excellent water resistance.
Further, Patent Document 2 discloses a colored composition containing an azo dye having good hue and fastness and a high molecular extinction coefficient.

International Publication No. 2013-047386 JP2016-084421A

In recent years, it has been desired to obtain a colored product with an excellent cyan color by coloring a fabric containing polyamide fibers. It is also desired that the resulting colored product has excellent sweat resistance and light resistance.
The present inventors investigated the coloring of a fabric containing polyamide fibers using the coloring composition described in Patent Document 1 or Patent Document 2, and found that the cyan color, sweat resistance, and It was found that the level of light resistance was not necessarily sufficient and there was room for further improvement.

SUMMARY OF THE INVENTION Accordingly, the present invention provides a coloring composition which, when used for coloring a fabric containing polyamide fibers, has an excellent cyan color tone and excellent sweat resistance and light resistance of the colored product. The task is to
Another object of the present invention is to provide a method for producing a colored product, a colored product, and a kit using the above-mentioned coloring composition.

The present inventor has completed the present invention as a result of intensive studies to solve the above problems. That is, it has been found that the above problem can be solved by the following configuration.

[1] A coloring composition used for coloring a fabric containing polyamide fibers,
Contains a colorant and water,
The colorant is selected from the group consisting of a compound represented by the general formula (IA) described below, a compound represented by the general formula (IB) described below, and a compound represented by the general formula (IC) described below. A coloring composition containing at least one type of.
[2] The compound represented by the above general formula (IA) is a compound represented by the below-mentioned general formula (IIA), and the compound represented by the above-mentioned general formula (IB) is a compound represented by the below-mentioned general formula (IIB). ), and the compound represented by the above general formula (IC) is a compound represented by the general formula (IIC) described below, the colored composition according to [1].
[3] The colorant is a compound represented by the general formula (IA),
The coloring according to [ ^{1] or [2], wherein R 1a} and R ^2a each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group, a methylamino group, an ethylamino group, or a dimethylamino group Composition.
[4] The colorant is a compound represented by the general formula (IIB),
The colored composition according to [2], wherein Y ^IIb is a hydrogen atom or the above substituent X, and Y ^IIb-2 is a hydrogen atom.
[5] The coloring agent is a compound represented by the general formula (IIC),
Y ^IIc is a hydrogen atom or a substituent having a Hammett substituent constant σp value of -0.20 to 0.50, which is an alkyl group, an aryl group, an alkylthio group, an arylthio group, an alkylcarbonylamino group, The colored composition according to [2], wherein the substituent is selected from the group consisting of an arylcarbonylamino group, an alkylsulfonylamino group, and an arylsulfonylamino group.
[6] The colored composition according to any one of [1] to [5], wherein L ^1a , L ^2a , L ^1b , L ^2b , L ^1c , and L ^2c are carbonyl groups.
[7] The colored composition according to any one of [1] to [6], which is an inkjet ink.
[8] A method for producing a colored product, comprising the step of applying the colored composition according to any one of [1] to [6] to a fabric containing polyamide fibers by an inkjet method.
[9] A colored product produced by the production method described in [8].
[10] A kit comprising the colored composition according to any one of [1] to [6] and a fabric containing polyamide fibers.

According to the present invention, it is possible to provide a coloring composition that, when used for coloring a fabric containing polyamide fibers, has an excellent cyan color tone and excellent sweat resistance and light resistance of the colored product.
Further, the present invention can provide a method for producing a colored product using the above-mentioned colored composition, a colored product, and a kit.

The present invention will be explained in detail below.
Although the description of the constituent elements described below may be made based on typical embodiments of the present invention, the present invention is not limited to such embodiments.

The meaning of each description in this specification is shown below.
In this specification, a numerical range expressed using "~" means a range that includes the numerical values written before and after "~" as lower and upper limits.
Furthermore, in this specification, the term "Z group having a Hammett substituent constant σp value of X to Y" means a group having a Hammett substituent constant σp value of X to Y among Z groups. . For example, when referring to an alkylsulfonyl group having a Hammett substituent constant σp value of 0.65 to 0.90, an alkylsulfonyl group having a Hammett substituent constant σp value of 0.65 to 0.90 ( For example, it means a methylsulfonyl group or an ethylsulfonyl group).

[Colored composition]
The coloring composition of the present invention is a coloring composition used for coloring a fabric containing polyamide fibers, and contains a colorant and water, and the colorant is a compound represented by the general formula (IA) described below. , a compound represented by the general formula (IB) described below, and a compound represented by the general formula (IC) described below (hereinafter also simply referred to as "specific compound"). including.
Although the mechanism by which the effects of the present invention are obtained by the coloring composition of the present invention having the above structure is not necessarily clear, the present inventors speculate as follows.
Azo dyes having a dissociable group (hereinafter also simply referred to as "dissociable azo dyes"), such as the above-mentioned specific compounds, have a dissociative group such as a phenolic hydroxyl group that dissociates into an anion state. Since the maximum absorption wavelength is bathochromically shifted, it has a structure that is preferable for cyan dyes whose maximum absorption wavelength is in the long wavelength region.
For example, by selecting appropriate functional groups as substituents R ^1a and R ^2a in a specific compound, and selecting a functional group with Hammett's substituent constant σp value set in an appropriate range as Y ^a , It is thought that by combining the two, it was possible to control the absorption wavelength range and express a more desirable cyan color.
As mentioned above, the dissociable azo dye exhibits a desirable cyan color by being in a dissociated anion state, and when exposed to sweat, it changes from a dissociated state to a non-dissociated state due to H ⁺ etc. in the sweat. This leads to deterioration of color tone. Furthermore, when exposed to light, dissociative azo dyes decompose, leading to deterioration of color, but this decomposition of dyes occurs mainly through the decomposition route from the non-dissociated state. The inventors believe that there is.
Therefore, in order for a dissociative azo dye to exist stably, it is important that the dissociative group dissociates and maintains an anionic state, and in the present invention, a specific compound with a predetermined skeleton is selected, Furthermore, it is presumed that by setting the Hammett's substituent constant σp value of the substituent within an appropriate range, it was possible to balance the color, sweat resistance, and light resistance.
Each component contained in the coloring composition will be described in detail below.

[Colorant]
<Specific compound>
The colored composition includes a coloring agent. The coloring agent contains at least one selected from the group consisting of a compound represented by general formula (IA), a compound represented by general formula (IB), and a compound represented by general formula (IC). include.

In general formula (IA), R ^1a and R ^2a each independently represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group, an alkylamino group, an arylamino group, a dialkyl Represents an amino group, diarylamino group, or alkylarylamino group.

The alkyl group may be linear, branched, or cyclic, and may further have a substituent.
Examples of the alkyl group include linear, branched, and cyclic alkyl groups having 1 to 20 carbon atoms. Among these, straight-chain or branched alkyl groups having 1 to 20 carbon atoms are preferred, straight-chain or branched alkyl groups having 1 to 10 carbon atoms are more preferred, and straight-chain or branched alkyl groups having 1 to 5 carbon atoms are preferred. A branched or branched alkyl group is more preferred, and a methyl group, ethyl group, or isopropyl group is most preferred.

Examples of the aryl group include a phenyl group and a naphthyl group. Among these, phenyl group and naphthyl group are preferred.
The above-mentioned heterocyclic group may be an aromatic heterocyclic group or an aliphatic heterocyclic group, for example, an aromatic heterocyclic group having 5 to 10 ring members, and an aromatic heterocyclic group having 5 to 10 ring members. Examples include aliphatic heterocycles. Examples of the heterocycle constituting the heterocyclic group include a pyridine ring, a quinoline ring, a furan ring, a thiophene ring, a benzothiophene ring, a pyrazole ring, an imidazole ring, a benzimidazole ring, a triazole ring, and an oxazole ring. Among these, a pyridine ring, a furan ring, or a thiophene ring is preferred.

The alkoxy group is preferably an alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 10 carbon atoms, and still more preferably a methoxy group, an ethoxy group, an isopropoxy group, or a t-butoxy group.
The above aryloxy group is preferably an aryloxy group having 6 to 20 carbon atoms, more preferably an aryloxy group having 6 to 10 carbon atoms, and even more preferably a phenoxy group.

The above amino group represents a primary amino group (-NH ₂ ).
The above-mentioned alkylamino group represents a substituent in which one hydrogen atom in the primary amino group (-NH ₂ ) is replaced with the above-mentioned alkyl group, and includes, for example, an alkylamino group having 1 to 20 carbon atoms. Among these, an alkylamino group having 1 to 10 carbon atoms is preferred, an alkylamino group having 1 to 5 carbon atoms is more preferred, and a methylamino group, an ethylamino group, or an isopropylamino group is even more preferred.
The above arylamino group represents a substituent in which one hydrogen atom in the primary amino group (-NH ₂ ) is replaced with the above aryl group, and includes, for example, an arylamino group having 6 to 20 carbon atoms. Among these, an arylamino group having 6 to 10 carbon atoms is preferred, and a phenylamino group is more preferred.

The above dialkylamino group represents a substituent in which two hydrogen atoms in the primary amino group (-NH ₂ ) are each independently substituted with the above alkyl group, for example, a dialkylamino group having 1 to 20 carbon atoms. can be mentioned. Note that the above carbon number means the total number of carbon atoms of two alkyl groups contained in the dialkylamino group. Among these, dialkylamino groups having 1 to 10 carbon atoms are preferred, dialkylamino groups having 1 to 5 carbon atoms are more preferred, and dimethylamino groups or diethylamino groups are even more preferred.
The above diarylamino group represents a substituent in which two hydrogen atoms in the primary amino group (-NH ₂ ) are each independently substituted with the above aryl group, for example, a diarylamino group having 12 to 30 carbon atoms. can be mentioned. In addition, the said carbon number means the total carbon number of two aryl groups contained in a diarylamino group. Among these, a diarylamino group having 12 to 20 carbon atoms is preferred, and a diphenylamino group is more preferred.
The above-mentioned alkylarylamino group represents a substituent in which one hydrogen atom in the primary amino group (-NH ₂ ) is substituted with the above-mentioned alkyl group, and the other hydrogen atom is substituted with the above-mentioned aryl group, such as , an alkylaryl amino group having 7 to 20 carbon atoms. The number of carbon atoms mentioned above means the total number of carbon atoms of the alkyl group and the number of carbon atoms of the aryl group contained in the alkylaryl amino group. Among these, an alkylaryl amino group having 7 to 10 carbon atoms is preferred, and a methylphenylamino group or an ethylphenylamino group is more preferred.

The following effects can be obtained: better cyan color of the resulting colored product, better sweat resistance of the colored product, and better light resistance of the colored product (hereinafter simply referred to as "the present invention"). ), and R ^1a and R ^2a each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group, a methylamino group, an ethylamino group, or a dimethylamino group. It is preferable that there be.

In general formula (IA), M represents a hydrogen atom or a cation. As M, a cation is preferable.
The cation represented by M is not particularly limited, and may be, for example, an inorganic cation or an organic cation.
Examples of inorganic cations include alkali metal cations such as lithium ions, sodium ions, and potassium ions, and ammonium ions.
Examples of the organic cation include pyridinium, tetramethylammonium, guanidinium, tetramethylguanidinium, amidinium, and tetraethylammonium.

In general formula (IA), L ^1a and L ^2a each independently represent a carbonyl group (-CO-) or a sulfonyl group (-SO ₂ -). As for L ^1a and L ^2a , it is preferable that at least one is a carbonyl group, and it is more preferable that both are carbonyl groups.

In the general formula (IA), Y ^a represents a substituent, and p represents an integer of 1 to 4.
Y ^a is preferably located at any of the 5th, 6th, and 7th positions in the 1,2-benziisothiazole ring in formula (IA), and is preferably located at the 5th or 6th position. More preferably, it is located at the 5th position.
Although p is not particularly limited, it is preferably an integer of 1 to 3, more preferably 1 or 2, and even more preferably 1.

The compound represented by general formula (IA) satisfies any of the following requirements 1 to 3.
As described later, in Requirements 1 to 3, the Hammett substituent constant σp value of the substituent represented by Y ^a depends on the type of group selected from Group I or Group II in which R ^1a and R ^2a are described later. The range is defined.
When the groups exemplified in Group I and the groups exemplified in Group II are compared, the groups exemplified in Group II have stronger electron-donating properties. Therefore, in Requirements 1 to 3, the range of Hammett's substituent constant σp value of the substituent represented by Y ^a is adjusted depending on the strength of electron donating properties of the groups selected for R ^1a and R ^2a . has been done.

Requirement 1: When R ^1a and R ^2a are each independently selected from Group I consisting of a hydrogen atom, an alkyl group, an aryl group, and a heterocyclic group, and p is 1, then Y ^a Hammett's substituent constant σp value of the above substituent is 0.65 to 0.90,
When R ^1a and R ^2a are each independently selected from the above Group I, and p is an integer of 2 to 4, Hammett's substitution of each of the plurality of substituents represented by Y ^a The total value of the base constant σp values is 0.65 to 0.90.

In the present invention, "Hammett's substituent constant σp value" is a constant specific to a substituent in a relational expression established as Hammett's rule. A positive Hammett's substituent constant σp value indicates that the substituent is electron-withdrawing.
Hammett's rule was developed in 1935 by L. P. This is a rule of thumb proposed by Hammett, and its validity is widely recognized today. The substituent constants determined by Hammett's rule include a σp value and a σm value. These values are listed in many popular texts.
Herein, Chem. Rev. , 1991, Vol. 91, pp. 165-195. Regarding substituents not described in the above literature, please refer to the literature "The Effect of Structure upon the Reactions of Organic Compounds. Benzene Derivatives" (J.Am.Chem.Soc.1937, 59, 1, 96-103). Adopt the value calculated according to the described calculation method.

When p is 1 in the above requirement 1, examples of the substituent represented by Y ^a include a cyano group and an alkylsulfonyl group (- SO ₂ R, R represents an alkyl group), an arylsulfonyl group having a Hammett substituent constant σp value of 0.65 to 0.90 (-SO ₂ Ar, Ar represents an aryl group), Hammett substituent Alkylaminosulfonyl group (-SO ₂ NHR, R represents an alkyl group) having a constant σp value of 0.65 to 0.90, dialkylamino having a Hammett substituent constant σp value of 0.65 to 0.90 Sulfonyl group (-SO ₂ NR ₂ , R represents an alkyl group), arylaminosulfonyl group (-SO ₂ NHAr, Ar represents an aryl group) with Hammett's substituent constant σp value of 0.65 to 0.90 ), a diarylaminosulfonyl group with a Hammett substituent constant σp value of 0.65 to 0.90 (-SO ₂ NAr ₂ , Ar represents an aryl group), a Hammett substituent constant σp value of 0.65 to 0.90 0.90 (-SO ₂ N(-R)Ar, R represents an alkyl group, Ar represents an aryl group), and a nitro group.
When p is an integer of 2 to 4, the substituent represented by Y ^a is, for example, a halogen atom, and the above-mentioned substituent represented by Y ^a when p is 1 in Requirement 1. and substituents selected from the group consisting of groups.
In addition, in Requirement 1, when p is an integer from 2 to 4, the sum of Hammett's substituent constant σp values of each of the plurality of substituents represented by Y ^a is from 0.65 to 0.90. At least one of the plurality of Y ^a may be a substituent whose Hammett substituent constant σp value is outside the range of 0.65 to 0.90.

In the case where R ^1a and R ^2a are each independently selected from the above Group I, and p is 1, the Hammett substituent constant σp value of the above substituent represented by Y ^a is such that the effect of the present invention is In terms of superiority, 0.65 to 0.80 is preferable, and 0.65 to 0.75 is more preferable.
In the case where R ^1a and R ^2a are each independently selected from the above Group I, and p is an integer of 2 to 4, each Hammett substituent of the plurality of substituents represented by Y ^a The total value of the constant σp values is preferably from 0.65 to 0.80, more preferably from 0.65 to 0.75, from the standpoint that the effects of the present invention are more excellent.

Examples of the alkylsulfonyl group having a Hammett's substituent constant σp value of 0.65 to 0.90 (hereinafter also simply referred to as "the σp value of Requirement 1") include a methylsulfonyl group and an ethylsulfonyl group. It will be done.
An example of the arylsulfonyl group having the σp value of Requirement 1 is a phenylsulfonyl group.
An example of the alkylaminosulfonyl group having the σp value of Requirement 1 is an ethylaminosulfonyl group.
The dialkylaminosulfonyl group having the σp value of Requirement 1 includes a dimethylaminosulfonyl group.
The arylaminosulfonyl group having the σp value of Requirement 1 includes a phenylaminosulfonyl group.
The diarylaminosulfonyl group having the σp value of Requirement 1 includes a diphenylaminosulfonyl group.
Examples of the alkylaryl aminosulfonyl group having the σp value of Requirement 1 include a methylphenylaminosulfonyl group.

Requirement 2: One of R ^1a and R ^2a is selected from Group I above, and the other of R ^1a and R ^2a is an alkoxy group, aryloxy group, amino group, alkylamino group, arylamino group, dialkylamino group, diarylamino group. and when p is 1, the Hammett substituent constant σp value of the substituent represented by Y ^a is 0.53 to 0. .90,
When one of R ^1a and R ^2a is selected from the above Group I, and the other of R ^1a and R ^2a is selected from the above Group II, and p is an integer of 2 to 4, a plurality of The sum of Hammett's substituent constant σp values of the substituents represented by Y ^a is 0.53 to 0.90.

When p is 1 in the above requirement 2, examples of the substituent represented by Y ^a include an alkylaminosulfonyl group having a Hammett substituent constant σp value of 0.53 to 0.90, a Hammett substituent A dialkylaminosulfonyl group having a group constant σp value of 0.53 to 0.90, an arylaminosulfonyl group having a Hammett substituent constant σp value of 0.53 to 0.90, and a Hammett substituent constant σp value of 0. A diarylaminosulfonyl group having a Hammett substituent constant σp value of 0.53 to 0.90, an aminosulfonyl group (-SO ₂ NH ₂ ), a cyano group, Alkylsulfonyl group with Hammett's substituent constant σp value of 0.53 to 0.90, arylsulfonyl group with Hammett's substituent constant σp value of 0.53 to 0.90, trifluoromethyl group, Hammett's substitution Examples thereof include a dialkylphosphonate group (-P(=O)(OR) ₂ , R represents an alkyl group) having a group constant σp value of 0.53 to 0.90, and a nitro group.
When p is an integer of 2 to 4, the substituent represented by Y ^a is, for example, a halogen atom, and the above-mentioned substituent represented by Y ^a when p is 1 in requirement 2. and substituents selected from the group consisting of groups.
In addition, in Requirement 2, when p is an integer of 2 to 4, the sum of Hammett's substituent constant σp values of each of the plurality of substituents represented by Y ^a is 0.53 to 0.90. At least one of the plurality of Y ^a may be a substituent whose Hammett substituent constant σp value is outside the range of 0.53 to 0.90.

When one of R ^1a and R ^2a is selected from the above Group I, the other of R ^1a and R ^2a is selected from the above Group II, and p is 1, the above substituent represented by Y ^a The Hammett's substituent constant σp value is preferably 0.53 to 0.80, more preferably 0.53 to 0.75, from the viewpoint of providing better effects of the present invention.
When one of R ^1a and R ^2a is selected from the above Group I, and the other of R ^1a and R ^2a is selected from the above Group II, and p is an integer of 2 to 4, a plurality of The total value of the Hammett's substituent constant σp value of each of the substituents represented by Y ^a is preferably 0.53 to 0.80, and 0.53 to 0.75, from the viewpoint that the effect of the present invention is more excellent. is more preferable.

Examples of the alkylaminosulfonyl group having a Hammett's substituent constant σp value of 0.53 to 0.90 (hereinafter also simply referred to as "the σp value of Requirement 2") include a 1-propylaminosulfonyl group.
The dialkylaminosulfonyl group having the σp value of Requirement 2 includes a dimethylaminosulfonyl group.
The arylaminosulfonyl group having the σp value of Requirement 2 includes a phenylaminosulfonyl group.
The diarylaminosulfonyl group having the σp value of Requirement 2 includes a diphenylaminosulfonyl group.
As the alkylaryl aminosulfonyl group having the σp value of Requirement 2, a methylphenylaminosulfonyl group can be mentioned.
Examples of the alkylsulfonyl group having the σp value of Requirement 2 include a methylsulfonyl group and an ethylsulfonyl group.
An example of the arylsulfonyl group having the σp value of requirement 2 is a phenylsulfonyl group.
The dialkylphosphonate group having the σp value of Requirement 2 includes a dimethylphosphonate group.

Requirement 3: When R ^1a and R ^2a are each independently selected from the above Group II, and p is 1, the Hammett substituent constant σp value of the above substituent represented by Y ^a is 0. 40 to 0.90,
When R ^1a and R ^2a are each independently selected from the above Group II, and p is an integer of 2 to 4, Hammett's substitution of each of the plurality of substituents represented by Y ^a The total value of the base constant σp values is 0.40 to 0.90.

When p is 1 in the above requirement 3, examples of the substituent represented by Y ^a include an alkylaminosulfonyl group having a Hammett substituent constant σp value of 0.40 to 0.90, a Hammett substituent A dialkylaminosulfonyl group having a group constant σp value of 0.40 to 0.90, an arylaminosulfonyl group having a Hammett substituent constant σp value of 0.40 to 0.90, and a Hammett substituent constant σp value of 0. A diarylaminosulfonyl group having a Hammett substituent constant σp value of 0.40 to 0.90, an aminosulfonyl group (-SO ₂ NH ₂ ), a cyano group, Alkylsulfonyl group with Hammett's substituent constant σp value of 0.40 to 0.90, arylsulfonyl group with Hammett's substituent constant σp value of 0.40 to 0.90, trifluoromethyl group, Hammett's substitution A dialkylphosphonate group (-P(=O)R ₂ ) having a group constant σp value of 0.40 to 0.90, a dialkylphosphine oxide group (-P(=O)R 2 ) having a Hammett substituent constant σp value of 0.40 to 0.90; -O-P(=O)(R ₂ ), R represents an alkyl group), an alkylcarbonyl group having a Hammett substituent constant σp value of 0.40 to 0.90 (-C(=O)-R , R represents an alkyl group), an alkoxycarbonyl group having a Hammett substituent constant σp value of 0.40 to 0.90 (-C(=O)OR, R represents an alkyl group), a Hammett substituent an alkylsulfinyl group having a constant σp value of 0.40 to 0.90 (-S(=O)-R, R represents an alkyl group), and a Hammett substituent constant σp value of 0.40 to 0.90; Examples include a certain arylsulfinyl group (-S(=O)-Ar, Ar represents an aryl group) and a 4-pyridyl group.
When p is an integer of 2 to 4, the substituent represented by Y ^a is, for example, a halogen atom, and the above-mentioned substituent represented by Y ^a when p is 1 in Requirement 3. and substituents selected from the group consisting of groups.
In addition, in Requirement 3, when p is an integer from 2 to 4, the sum of Hammett's substituent constant σp values of each of the plurality of substituents represented by Y ^a is in the range of 0.40 to 0.90. At least one of the plurality of Y ^a may be a substituent having a Hammett's substituent constant σp value outside the range of 0.40 to 0.90.

When R ^1a and R ^2a are each independently selected from the above Group II, and p is 1, the Hammett substituent constant σp value of the above substituent represented by Y ^a has the effect of the present invention. 0.40 to 0.80 is preferable, and 0.40 to 0.75 is more preferable in terms of better .
When R ^1a and R ^2a are each independently selected from the above Group II, and p is an integer of 2 to 4, Hammett's substitution of each of the plurality of substituents represented by Y ^a The total value of the base constants σp value is preferably 0.40 to 0.80, more preferably 0.40 to 0.75, from the viewpoint of achieving better effects of the present invention.

Examples of the alkylaminosulfonyl group having a Hammett's substituent constant σp value of 0.40 to 0.90 (hereinafter also simply referred to as "the σp value of Requirement 3") include a 1-propylaminosulfonyl group.
The dialkylaminosulfonyl group having the σp value of Requirement 3 includes a dimethylaminosulfonyl group.
The arylaminosulfonyl group having the σp value of Requirement 3 includes a phenylaminosulfonyl group.
The diarylaminosulfonyl group having the σp value of requirement 3 includes a diphenylaminosulfonyl group.
As the alkylaryl aminosulfonyl group having the σp value of Requirement 3, a methylphenylaminosulfonyl group can be mentioned.
Examples of the alkylsulfonyl group having the σp value of requirement 3 include a methylsulfonyl group and an ethylsulfonyl group.
The arylsulfonyl group having the σp value of requirement 3 includes a phenylsulfonyl group.
The dialkylphosphonate group having the σp value of Requirement 3 includes a dimethylphosphonate group.
The dialkylphosphine oxide group having the σp value of Requirement 3 includes a dimethylphosphine oxide group.
As the alkylcarbonyl group having the σp value of Requirement 3, a methylcarbonyl group can be mentioned.
An example of the alkoxycarbonyl group having the σp value of requirement 3 is an ethoxycarbonyl group.
An example of the alkylsulfinyl group having the σp value of requirement 3 is a methylsulfinyl group.
An example of the arylsulfinyl group having the σp value of requirement 3 is a phenylsulfinyl group.

The compound represented by the above general formula (IA) is preferably a compound represented by the general formula (IIA) because the effects of the present invention are more excellent.

In general formula (IIA), R ^1a , R ^2a , M, L ^1a and L ^2a have the same meanings as R ^1a , R ^2a , M, L ^1a and L ^2a in general formula (IA) above, respectively.
When R ^1a and R ^2a are each independently selected from the above Group I, Y ^IIa is a substituent having a Hammett substituent constant σp value of 0.65 to 0.90, and includes a cyano group, an alkylsulfonyl arylsulfonyl group, alkylaminosulfonyl group, dialkylaminosulfonyl group, arylaminosulfonyl group, diarylaminosulfonyl group, and alkylaminosulfonyl group.
That is, when R ^1a and R ^2a are each independently selected from the above Group I, Y ^IIa is a cyano group, an alkylsulfonyl group having a σp value of Requirement 1, an arylsulfonyl group having a σp value of Requirement 1, or an arylsulfonyl group having a σp value of Requirement 1. Alkylaminosulfonyl group with σp value, dialkylaminosulfonyl group with σp value of requirement 1, arylaminosulfonyl group with σp value of requirement 1, diarylaminosulfonyl group with σp value of requirement 1, and alkyl group with σp value of requirement 1 A substituent selected from the group consisting of arylaminosulfonyl groups.
Specific examples of the above groups are as described above.
When R ^1a and R ^2a are each independently selected from the above Group I, the Hammett substituent constant σp value of the above substituent represented by Y ^IIa is 0.65, since the effect of the present invention is more excellent. ~0.80 is preferred, and 0.65 ~ 0.75 is more preferred.

When one of R ^1a and R ^2a is selected from the above Group I and the other of R ^1a and R ^2a is selected from the above Group II, Y ^IIa has a Hammett substituent constant σp value of 0.53 to 0. 90, which is an alkylaminosulfonyl group, a dialkylaminosulfonyl group, an arylaminosulfonyl group, a diarylaminosulfonyl group, an alkylaminosulfonyl group, an aminosulfonyl group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, A substituent selected from the group consisting of a trifluoromethyl group and a dialkylphosphonate group.
That is, when one of R ^1a and R ^2a is selected from the above Group I and the other of R ^1a and R ^2a is selected from the above Group II, Y ^IIa is an alkylaminosulfonyl group having the σp value of Requirement 2, Requirement A dialkylaminosulfonyl group with a σp value of 2, an arylaminosulfonyl group with a σp value of requirement 2, a diarylaminosulfonyl group with a σp value of requirement 2, an alkylaminosulfonyl group, an aminosulfonyl group, a cyano group with a σp value of requirement 2 , an alkylsulfonyl group having a σp value of Requirement 2, an arylsulfonyl group having a σp value of Requirement 2, a trifluoromethyl group, and a dialkylphosphonate group having a σp value of Requirement 2.
Specific examples of the above groups are as described above.
When one of R ^1a and R ^2a is selected from the above Group I and the other of R ^1a and R ^2a is selected from the above Group II, the Hammett substituent constant σp value of the above substituent represented by Y ^IIa is , 0.53 to 0.80 is preferable, and 0.53 to 0.75 is more preferable in terms of the effect of the present invention being more excellent.

When R ^1a and R ^2a are each independently selected from the above group II, Y ^IIa is a substituent having a Hammett substituent constant σp value of 0.40 to 0.90, and is an alkylaminosulfonyl group, dialkylaminosulfonyl group, arylaminosulfonyl group, diarylaminosulfonyl group, alkylarylaminosulfonyl group, aminosulfonyl group, cyano group, alkylsulfonyl group, arylsulfonyl group, trifluoromethyl group, dialkylphosphonate group, dialkylphosphine oxide group, A substituent selected from the group consisting of an alkylcarbonyl group, an alkoxycarbonyl group, an alkylsulfinyl group, an arylsulfinyl group, and a 4-pyridyl group.
That is, when R ^1a and R ^2a are each independently selected from the above group II, Y ^IIa is an alkylaminosulfonyl group having a σp value of Requirement 3, a dialkylaminosulfonyl group having a σp value of Requirement 3, or a dialkylaminosulfonyl group having a σp value of Requirement 3. Arylaminosulfonyl group with a value of σp value of Requirement 3, a diarylaminosulfonyl group with a σp value of Requirement 3, an alkylaryl aminosulfonyl group with a σp value of Requirement 3, an aminosulfonyl group, a cyano group, an alkylsulfonyl group with a σp value of Requirement 3, Arylsulfonyl group, trifluoromethyl group with σp value, dialkylphosphonate group with σp value of requirement 3, dialkylphosphine oxide group with σp value of requirement 3, alkylcarbonyl group with σp value of requirement 3, alkoxy with σp value of requirement 3 The substituent is selected from the group consisting of a carbonyl group, an alkylsulfinyl group having a σp value of Requirement 3, an arylsulfinyl group having a σp value of Requirement 3, and a 4-pyridyl group.
Specific examples of the above groups are as described above.
When R ^1a and R ^2a are each independently selected from the above group II, the Hammett substituent constant σp value of the above substituent represented by Y ^IIa is 0.40, since the effect of the present invention is more excellent. ~0.80 is preferred, and 0.40 ~ 0.75 is more preferred.

In general formula (IB), R ^1b and R ^2b each independently represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group, an alkylamino group, an arylamino group, a dialkyl Represents an amino group, diarylamino group, or alkylarylamino group.

The ^above -mentioned alkyl group, aryl ^group , heterocyclic group, alkoxy group, aryloxy group, amino group, alkylamino group, arylamino group, dialkylamino group, diarylamino group, or , the embodiments and preferred embodiments of the alkylaryl amino group are as explained for R ^1a and R ^2a specified in the above general formula (IA), respectively. Among them, R ^1b and R ^2b are as follows: Preferably, each group is independently selected from the group consisting of a methyl group, an isopropyl group, a methoxy group, a methylamino group, and a dimethylamino group.

In general formula (IB), M represents a hydrogen atom or a cation. The aspects and preferred aspects of M are as explained for M specified in the above general formula (IA).

In general formula (IB), L ^1b and L ^2b each independently represent a carbonyl group or a sulfonyl group. As for L ^1b and L ^2b , it is preferable that at least one is a carbonyl group, and it is more preferable that both are carbonyl groups.

In the general formula (IB), Y ^b represents a substituent, and q represents an integer of 0 to 3.
q is not particularly limited, but is preferably an integer of 0 to 2, more preferably 0 or 1.

In general formula (IB), when q is 1, the Hammett substituent constant σp value of the substituent represented by Y ^b is 0.00 to 0.72, and q is 2 or 3. In this case, the total Hammett's substituent constant σp value of each of the plurality of substituents represented by Y ^b is 0.00 to 0.72.
In the compound represented by general formula (IB), one nitrogen atom is contained in the ring condensed with the isothiazole ring. Due to the inclusion of a nitrogen atom in this way, the Hammett's substituent constant σp value of the group substituting this ring differs from the range of the compound represented by the general formula (IA).

When q is 1, the substituent represented by Y ^b is, for example, a substituent whose Hammett substituent constant σp value is 0.00 to 0.72, such as a halogen atom, a formyl group, an alkyl group, etc. Carbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, aminocarbonyl group, alkylaminocarbonyl group, dialkylaminocarbonyl group, arylaminocarbonyl group, diarylaminocarbonyl group, alkylarylaminocarbonyl group, cyano group, alkyl Sulfonyl group, arylsulfonyl group, alkylaminosulfonyl group, dialkylaminosulfonyl group, arylaminosulfonyl group, diarylaminosulfonyl group, alkylarylaminosulfonyl group, aminosulfonyl group, aryl group, heterocyclic group, aryloxy group, alkylthio group , arylthio group, alkylcarbonylamino group (-NHCOR, R represents an alkyl group), arylcarbonylamino group (-NHCOAr, Ar represents an aryl group), alkylsulfonylamino group (-NHSO ₂ R, R represents an alkyl group) ), arylsulfonylamino group (-NHSO ₂ Ar, Ar represents an aryl group), trifluoromethyl group, dialkylphosphonate group, dialkylphosphine oxide group, alkylsulfinyl group, arylsulfinyl group, and 4-pyridyl group Substituents selected from the group consisting of:

When q is 2 or 3, the substituent represented by Y ^b includes a halogen atom, formyl group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, aminocarbonyl group, alkylaminocarbonyl group. group, dialkylaminocarbonyl group, arylaminocarbonyl group, diarylaminocarbonyl group, alkylaminocarbonyl group, cyano group, alkylsulfonyl group, arylsulfonyl group, alkylaminosulfonyl group, dialkylaminosulfonyl group, arylaminosulfonyl group, diaryl Aminosulfonyl group, alkylarylaminosulfonyl group, aminosulfonyl group, alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, alkylthio group, arylthio group, amino group, alkylamino group, dialkylamino group, arylamino group group, diarylamino group, alkylarylamino group, alkylcarbonylamino group, arylcarbonylamino group, alkylsulfonylamino group, arylsulfonylamino group, trifluoromethyl group, dialkylphosphonate group, dialkylphosphine oxide group, alkylsulfinyl group, aryl Examples include substituents selected from the group consisting of a sulfinyl group and a 4-pyridyl group.
Note that when q is 2 or 3, the sum of Hammett's substituent constant σp values of each of the plurality of substituents represented by Y ^b may be in the range of 0.00 to 0.72; At least one of Y ^b may be a substituent having a Hammett's substituent constant σp value outside the range of 0.00 to 0.72.

When q is 1, the Hammett substituent constant σp value of the substituent represented by Y ^b is preferably 0.00 to 0.66, and 0.00 to 0.66, since the effect of the present invention is more excellent. ~0.50 is more preferred.
When q is 2 or 3, the total Hammett's substituent constant σp value of each of the plurality of substituents represented by ^Y 0.66 is preferable, and 0.00 to 0.50 is more preferable.

The substituents represented by ^Yb include, among others, a bromine atom, a chlorine atom, a phenylaminocarbonyl group, a methylsulfonylamino group, a phenylsulfonylamino group, a methylcarbonylamino group, a phenyl group, a methylcarbonyl group, an ethylcarbonyl group, Methoxy group, methylthio group, methyl group, phenylsulfonyl group, methylsulfonyl group, group formed by removing one hydrogen atom from pyridine (pyridine ring group), group formed by removing one hydrogen atom from pyrimidine (pyrimidine ring group) , or a group formed by removing one hydrogen atom from thiophene (thiophene ring group) is preferable.

The compound represented by the general formula (IB) is preferably a compound represented by the general formula (IIB) in that the effects of the present invention are more excellent.

In general formula (IIB), R ^1b , R ^2b , M, L ^1b and L ^2b have the same meanings as R ^1b , R ^2b , M, L ^1b and L ^2b in general formula (IB) above, respectively.
Y ^IIb and Y ^IIb-2 are each independently a hydrogen atom or a substituent X,
Substituent X is a halogen atom, formyl group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, aminocarbonyl group, alkylaminocarbonyl group, dialkylaminocarbonyl group, arylaminocarbonyl group, diarylaminocarbonyl group group, alkylaminocarbonyl group, cyano group, alkylsulfonyl group, arylsulfonyl group, alkylaminosulfonyl group, dialkylaminosulfonyl group, arylaminosulfonyl group, diarylaminosulfonyl group, alkylaminosulfonyl group, aminosulfonyl group, alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, alkylthio group, arylthio group, amino group, alkylamino group, dialkylamino group, arylamino group, diarylamino group, alkylarylamino group, alkylcarbonylamino group , an arylcarbonylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, a trifluoromethyl group, a dialkylphosphonate group, a dialkylphosphine oxide group, an alkylsulfinyl group, an arylsulfinyl group, and a 4-pyridyl group. is a substituent.
However, when one of Y ^IIb and Y ^IIb-2 is a hydrogen atom and the other is a substituent X, the Hammett substituent constant σp value of the group represented by the substituent X is 0.00 to 0. .72, and when both Y ^IIb and Y ^IIb-2 are substituents X, the sum of Hammett's substituent constant σp values of the two substituents X is 0.00 to 0.72.
Among these, it is preferable that Y ^IIb is a hydrogen atom or a substituent X, and Y ^IIb-2 is a hydrogen atom, since the effects of the present invention are more excellent.

When one of Y ^IIb and Y ^IIb-2 is a hydrogen atom and the other is a substituent X, the Hammett's substituent constant σp value of the group represented by the substituent In terms of superiority, it is preferably 0.00 to 0.66, more preferably 0.00 to 0.50.
When both Y ^IIb and Y ^IIb-2 are substituents X, the total value of Hammett's substituent constant σp values of the two substituents .66 is preferred, and 0.00 to 0.50 is more preferred.

When one of Y ^IIb and Y ^IIb-2 is a hydrogen atom and the other is a substituent X, the substituent X includes a cyano group, a halogen atom, and a Hammett substituent constant σp value of 0.00 to 0. 72, an arylsulfonyl group having a Hammett substituent constant σp value of 0.00 to 0.72, an alkylsulfonyl group having a Hammett substituent constant σp value of 0.00 to 0.72, Hammett A heterocyclic group having a substituent constant σp value of 0.00 to 0.72, an aryl group having a Hammett substituent constant σp value of 0.00 to 0.72, and a Hammett substituent constant σp value of 0.00 to 0.72. An alkylcarbonylamino group or formyl group having a value of 00 to 0.72, or an arylaminocarbonyl group having a Hammett substituent constant σp value of 0.00 to 0.72 is preferred.

Examples of alkoxycarbonyl groups having Hammett's substituent constant σp value of 0.00 to 0.72 (hereinafter also simply referred to as "σp value defined by substituent X") include methoxycarbonyl groups and ethoxycarbonyl groups. Examples include carbonyl groups.
The arylsulfonyl group having the σp value defined by the substituent X includes a phenylsulfonyl group and a 4-methylsulfonyl group.
Examples of the alkylsulfonyl group having the σp value defined by the substituent X include a methylsulfonyl group.
Examples of the heterocyclic group having the σp value defined by the substituent X include a pyridine ring group, a thiophene ring group, and a pyrimidine ring group.
The aryl group having the σp value defined by the substituent X includes a phenyl group.
The alkylcarbonylamino group having the σp value defined by the substituent X includes a methylcarbonylamino group.
The arylaminocarbonyl group having the σp value defined by the substituent X includes a phenylaminocarbonyl group.

When both Y ^IIb and Y ^IIb-2 are substituents X, the sum of Hammett's substituent constant σp values of the two substituents are each independently preferably a cyano group, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an arylsulfonylamino group, an alkoxycarbonyl group, an alkylcarbonylamino group, or an alkylsulfonylamino group.

In general formula (IC), R ^1c and R ^2c each independently represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group, an alkylamino group, an arylamino group, a dialkyl Represents an amino group, diarylamino group, or alkylarylamino group.

An alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group, an alkylamino group, an arylamino group, a dialkylamino group, a diarylamino group, or an alkyl group represented by R ^1c and ^R 2c above. The embodiments and preferred embodiments of the arylamino group are as explained for R ^1a and R ^2a specified in the above general formula (IA), respectively, but among them, R ^1c and R ^2c are each independently It is preferably selected from the group consisting of a methyl group, an isopropyl group, a methoxy group, an ethylamino group, and a dimethylamino group.

In general formula (IC), M represents a hydrogen atom or a cation. The aspects and preferred aspects of M are as explained for M specified in the above general formula (IA).

In general formula (IC), L ^1c and L ^2c each independently represent a carbonyl group or a sulfonyl group. As for L ^1c and L ^2c , it is preferable that at least one is a carbonyl group, and it is more preferable that both are carbonyl groups.

In the general formula (IC), Y ^c represents a substituent, and r represents an integer of 0 to 2.
Although r is not particularly limited, 0 or 1 is preferable, and 1 is more preferable.

In general formula (IC), when r is 1, the Hammett substituent constant σp value of the substituent represented by Y ^c is -0.30 to 0.50, and when r is 2 In this case, the total Hammett's substituent constant σp value of each of the plurality of substituents represented by Y ^c is −0.30 to 0.50.
In the compound represented by general formula (IC), two nitrogen atoms are contained in the ring condensed with the isothiazole ring. Due to the inclusion of such a nitrogen atom, the Hammett's substituent constant σp value of the group substituting this ring differs from the range of the compound represented by the general formula (IA).

When r is 1, examples of the substituent represented by Y ^c include an alkyl group having a Hammett substituent constant σp value of -0.30 to 0.50, and an alkyl group having a Hammett substituent constant σp value of -0.30 to 0.50. An aryl group having a Hammett's substituent constant σp value of -0.30 to 0.50, an alkoxy group having a Hammett substituent constant σp value of -0.30 to 0.50. A certain aryloxy group, an alkylthio group whose Hammett substituent constant σp value is -0.30 to 0.50, an arylthio group whose Hammett substituent constant σp value is -0.30 to 0.50, Hammett's substitution Alkylcarbonylamino group having a group constant σp value of -0.30 to 0.50, arylcarbonylamino group having a Hammett substituent constant σp value of -0.30 to 0.50, Hammett substituent constant σp value is -0.30 to 0.50, an arylsulfonylamino group whose Hammett's substituent constant σp value is -0.30 to 0.50, and a Hammett's substituent constant σp value of -0. Alkylcarbonyl group having a value of 30 to 0.50, an aralkylthio group having a Hammett substituent constant σp value of -0.30 to 0.50 (-SCH ₂ Ar, Ar represents an aryl group), Hammett substituent A dialkylaminocarbonylalkylenethio group (-S-L-CONR ₂ , L represents an alkylene group and R represents an alkyl group) having a constant σp value of -0.30 to 0.50, and Hammett's substituent constant Examples include arylcarbonylamino groups in which an alkyl group, a halogen atom, or an alkoxy group is substituted on an aryl group and have a σp value of -0.30 to 0.50.
When r is 2, the substituent represented by Y ^c is selected from the group consisting of a halogen atom and the above-mentioned substituent represented by Y ^c when r is 1. Examples include substituents.
Note that when r is 2, the sum of Hammett's substituent constant σp values of each of the two substituents represented by Y ^c may be in the range of −0.30 to 0.50, and At least one of Y ^c may be a substituent having a Hammett's substituent constant σp value outside the range of −0.30 to 0.50.

When r is 1, the Hammett substituent constant σp value of the substituent represented by Y ^c is preferably −0.25 to 0.50, and −0. .20 to 0.30 is more preferable.
When r is 2, the total Hammett's substituent constant σp value of each of the plurality of substituents represented by Y ^c is −0.25 to 0, in that the effect of the present invention is better .50 is preferred, and -0.20 to 0.30 is more preferred.

As the alkyl group, the Hammett's substituent constant σp value is -0.30 to 0.50 (hereinafter also simply referred to as "the σp value defined by ^Yc "), a methyl group or an isopropyl group is used. Can be mentioned.
An example of the aryl group having a σp value defined by ^Yc is a phenyl group.
The alkoxy group having the σp value defined by Y ^c includes a methoxy group.
The aryloxy group having the σp value defined by Y ^c includes a phenyloxy group.
Examples of the alkylthio group having a σp value defined by Y ^c include a methylthio group and an ethylthio group.
The arylthio group having the σp value defined by ^Yc includes a phenylthio group.
Examples of the alkylcarbonylamino group having a σp value defined by ^Yc include a methylcarbonylamino group and an isopropylcarbonylamino group.
The arylcarbonylamino group having the σp value defined by Y ^c includes a phenylcarbonylamino group.
Examples of the alkylsulfonylamino group having a σp value defined by ^Yc include a methylsulfonylamino group.
The arylsulfonylamino group having the σp value defined by ^Yc includes a phenylsulfonylamino group.

The compound represented by the general formula (IC) is preferably a compound represented by the general formula (IIC).

In general formula (IIC), R ^1c , R ^2c , M, L ^1c and L ^2c have the same meanings as R ^1c , R ^2c , M, L ^1c and L ^2c in the above general formula (IC), respectively.
Y ^IIc is a hydrogen atom or a substituent having a Hammett substituent constant σp value of -0.30 to 0.50, which is an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio A substituent selected from the group consisting of alkylcarbonylamino, arylcarbonylamino, alkylsulfonylamino, and arylsulfonylamino groups.
In other words, Y ^IIc is a hydrogen atom, an alkyl group with a σp value defined by ^Yc , an aryl group with a σp value defined by ^Yc , an alkoxy group with a σp value defined by ^Yc , and an alkyl group with a σp value defined by ^Yc . An aryloxy group with a σp value defined by ^Yc , an alkylthio group with a σp value defined by ^Yc , an alkylcarbonylamino group with a σp value defined by ^Yc , an alkylthio group with a σp value defined by ^Yc , ^an arylcarbonylamino group with a σp ^value of
Specific examples of the above groups are as described above.
Among them, Y ^IIc has a hydrogen atom or a Hammett's substituent constant σp value of −0.20 to 0.50 (preferably −0.20 to 0.30) in that the effect of the present invention is more excellent. ), which is a substituent selected from the group consisting of an alkyl group, an aryl group, an alkylthio group, an arylthio group, an alkylcarbonylamino group, an arylcarbonylamino group, an alkylsulfonylamino group, and an arylsulfonylamino group. It is preferable that it is a group.

The molecular weight of the specific compound is preferably 300 to 1000, more preferably 340 to 800, and even more preferably 400 to 600.

The method for synthesizing the compound represented by general formula (IA) is not particularly limited, but for example, as shown in the scheme below, a compound represented by general formula (AA) and a compound represented by general formula (CA) can be synthesized. An example is a diazo coupling reaction using
The method for synthesizing the compound represented by general formula (IB) is not particularly limited, but for example, as shown in the scheme below, a compound represented by general formula (AB) and a compound represented by general formula (CB) can be synthesized. An example is a diazo coupling reaction using
The method of synthesizing the compound represented by the general formula (IC) is not particularly limited, but for example, as shown in the scheme below, a compound represented by the general formula (AC) and a compound represented by the general formula (CC) can be synthesized. An example is a diazo coupling reaction using

The compound represented by the general formula (AA), the compound represented by the general formula (AB), and the compound represented by the general formula (AC) can be prepared, for example, using a known organic compound starting from commercially available or known raw materials. It can be synthesized by the following route combining synthetic reactions.

The compound represented by the general formula (CA) can be synthesized, for example, by the following route starting from commercially available raw materials and combining known organic synthesis reactions.
A compound represented by the general formula (CB) and a compound represented by the general formula (CC) can also be synthesized in the same manner.

Specific examples of specific compounds are shown below, but the present invention is not limited thereto.

The content of the specific compound in the coloring composition is not particularly limited, but it is preferably 0.1 to 20% by mass, and 0.2 to 15% by mass, based on the total mass of the coloring composition, in order to achieve better effects of the present invention. Mass% is more preferred.
One type of specific compound may be used, or two or more types may be used. When two or more types are used, it is preferable that their total amount falls within the above range.

〔water〕
The coloring composition contains water.
The water is not particularly limited, and may be, for example, ion exchange water or tap water.
The content of water is not particularly limited, and is preferably 20.0 to 99.9% by mass, more preferably 35.0 to 99.8% by mass, based on the total mass of the coloring composition.

[Optional ingredients]
The coloring composition may contain arbitrary components in addition to the above-mentioned specific compound and water.

<Organic solvent>
The coloring composition may contain an organic solvent.
The organic solvent is not particularly limited, but preferably is an aqueous organic solvent, such as polyhydric alcohols (e.g. ethylene glycol and glycerin), amines, monohydric alcohols, alkyl ethers of polyhydric alcohols, heterocyclic and acetonitrile.
When the coloring composition contains an organic solvent, the content of the organic solvent is not particularly limited, and is preferably 1 to 60% by weight, more preferably 2 to 50% by weight, based on the total weight of the coloring composition.
One type of organic solvent may be used, or two or more types may be used. When two or more types are used, it is preferable that their total amount falls within the above range.

<Surfactant>
The colored composition may contain a surfactant, and the colored composition preferably contains a surfactant from the viewpoint of improving storage stability, ejection stability, ejection accuracy, and the like.
As the surfactant, for example, any of cationic surfactants, anionic surfactants, amphoteric surfactants, and nonionic surfactants can be used.
Examples of the cationic surfactant include aliphatic amine salts, aliphatic quaternary ammonium salts, benzalkonium salts, benzethonium chloride, pyridinium salts, and imidazolinium salts.

Examples of the anionic surfactant include fatty acid soap, N-acyl-N-methylglycine salt, N-acyl-N-methyl-β-alanine salt, N-acylglutamate, alkyl ether carboxylate, acyl peptide, alkyl sulfonate, alkylbenzene sulfonate, alkylnaphthalene sulfonate, dialkyl sulfosuccinate salt, alkyl sulfoacetate, α-olefin sulfonate, N-acylmethyl taurine, sulfated oil, higher alcohol Sulfate ester salt, secondary higher alcohol sulfate ester salt, alkyl ether sulfate, secondary higher alcohol ethoxy sulfate, polyoxyethylene alkylphenyl ether sulfate, monoglysulfate, fatty acid alkylolamide sulfate ester salt, alkyl ether phosphorus Examples include acid ester salts and alkyl phosphate ester salts.

Examples of amphoteric surfactants include carboxybetaine type, sulfobetaine type, aminocarboxylate, and imidazolinium betaine.
Examples of nonionic surfactants include polyoxyethylene alkyl ether, polyoxyethylene secondary alcohol ether, polyoxyethylene alkylphenyl ether, polyoxyethylene sterol ether, polyoxyethylene lanolin derivative, polyoxyethylene polyoxypropylene. Alkyl ether, polyoxyethylene glycerin fatty acid ester, polyoxyethylene castor oil, hydrogenated castor oil, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyethylene glycol fatty acid ester, fatty acid monoglyceride, polyglycerin fatty acid ester, sorbitan fatty acid ester , propylene glycol fatty acid ester, sucrose fatty acid ester, fatty acid alkanolamide, polyoxyethylene fatty acid amide, polyoxyethylene alkylamine, alkylamine oxide, acetylene glycol, and acetylene alcohol.

When the coloring composition contains a surfactant, the content of the surfactant is preferably 0.001 to 5.0% by mass, and 0.002 to 4.0% by mass based on the total mass of the coloring composition. is more preferable.
One type of surfactant may be used, or two or more types may be used. When two or more types are used, it is preferable that their total amount falls within the above range.

<Other additives>
The coloring composition may also contain other conventionally known additives. For example, ultraviolet absorbers, pH adjusters, color pastes, preservatives, antifungal agents, antifading agents, emulsion stabilizers, penetration enhancers, infrared absorbers, optical brighteners, antifoaming agents, lubricants, thickeners. agents, antistatic agents, matting agents, antioxidants, resistivity regulators, rust preventives, inorganic pigments, and reduction inhibitors.

[Physical properties of colored composition]
From the viewpoint of handling, the viscosity of the colored composition at 25° C. is preferably 30 mPa·s or less, more preferably 20 mPa·s or less. Although the lower limit is not particularly limited, it is often 1 mPa·s or more.

[Method for producing colored composition]
The method for producing the colored composition is not particularly limited, and the colored composition can be produced by mixing the above-mentioned components.
When mixing, a stirring process may be performed as necessary. The stirring process can be performed using a known dispersion device.
Further, the above mixing may be performed in a heated environment. The heating temperature during the heat treatment is preferably 25 to 60°C, more preferably 30 to 45°C.
Moreover, after mixing each component, a filtration process may be performed as necessary.

[ink]
The coloring composition of the present invention can be suitably used as an ink, and in particular, can be suitably used as an inkjet ink.

[Method for manufacturing colored products]
The coloring composition of the present invention is used for coloring fabrics containing polyamide fibers.
An example of coloring is a dyeing method in which a coloring composition is applied onto an object to be colored to give a pattern shape, and a coloring agent is dyed or fixed to the object to create a dyed object with a pattern. It will be done. Industrially, examples include screen printing using a plate, roller printing, a transfer method using transfer paper, and an inkjet method.
The method of coloring a fabric containing polyamide fibers using the coloring composition of the present invention is not particularly limited, and examples include screen printing, roller printing, a transfer method using transfer paper, and an inkjet method as described above. .
Among these, the inkjet method is preferred because of its excellent productivity. More specifically, a method for producing a colored product is preferred, which includes a step of applying the colored composition of the present invention to a fabric containing polyamide fibers by an inkjet method (hereinafter, this step is also referred to as an inkjet step).
Hereinafter, the method for producing a colored product using the above-mentioned inkjet method will be described in detail.
Below, the fabric used will be explained first, and then the process steps will be explained in detail.

[Fabric]
The material constituting the polyamide fibers contained in the fabric may be any polyamide, such as nylon 6 and nylon 66.
The fabric containing polyamide fibers may be composed only of polyamide fibers, or may contain fibers other than polyamide fibers.
When the fabric contains fibers other than polyamide fibers, the content of the polyamide fibers is preferably 30% by mass or more, more preferably 50% by mass or more, based on the total mass of the fabric.
When the polyamide fibers are nylon fibers, the average thickness of the nylon fibers is preferably 1 to 10 deniers, more preferably 2 to 6 deniers.

[Process steps]
In this step, the colored composition of the present invention is applied to a fabric containing polyamide fibers by an inkjet method.
The above-mentioned inkjet method is a method in which the colored composition of the present invention is ejected from an inkjet recording head, the colored composition of the present invention is applied to a fabric, and an image is printed.
A known inkjet device can be used to carry out the above inkjet method.

[Other processes]
The method for producing a colored product of the present invention may include steps other than the above-described inkjet step.

<Pre-treatment process>
The method for producing a colored product of the present invention may include a step of pretreating the fabric before the inkjet step.
Pre-treatment performed on fabric is a process in which various pre-treatment agents such as aqueous (water-soluble) polymers, aqueous (water-soluble) metal salts, pH adjusters, hydrotropes, and pH buffering agents are applied to the fabric. It is. In the pretreatment, it is preferable to pat the fabric with a pretreatment agent at a reduction rate of 5 to 150% (preferably 10 to 130%).
Furthermore, a water repellent, a surfactant, etc. may be added to the fabric.
The method of applying the pretreatment agent to the fabric is not particularly limited, and examples include a dipping method, a pad method, a coating method, a spray method, and an inkjet method.
Each component used in the pretreatment includes the components described in paragraphs 0119 to 0123 of International Publication No. 2013/047386.

<Post-processing process>
The method for producing a colored product of the present invention may include a post-treatment step after the inkjet step. By performing the post-treatment step described below, it is possible to promote the fixation of the colorant to the polyamide fibers, and then to sufficiently remove the unfixed colorant, other components, and pretreatment agent.

Examples of the post-treatment process include a drying process, a steam process, and a washing process, which will be described later. In the post-treatment process, it is preferable that a drying process, a steam process, and a washing process are performed in this order.

-Drying process-
The drying process is a process of drying the fabric to which the coloring composition has been applied in the inkjet process. By carrying out this step, the printing density can be improved and bleeding can be effectively prevented.
The drying conditions are not particularly limited, and the drying temperature is preferably room temperature to 150°C, and the drying time is preferably 0.5 to 30 minutes.
The drying method is preferably an air convection method, a heating roll direct attachment method, or an irradiation method.

-Steam process-
The steam process is a process in which the fabric to which the coloring composition has been applied in the inkjet process is subjected to heat treatment using steam.
When the fabric is a fabric containing nylon fibers as a main component, the time for the steam step is preferably 1 minute to 90 minutes, more preferably 3 minutes to 60 minutes.
Here, when a fabric "contains a certain fiber as a main component", it means that the fiber content is the largest among the fibers contained in the fabric.

-Cleaning process-
The washing process is a process of washing the fabric to which the coloring composition has been applied in the inkjet process. By carrying out this step, unfixed colorant and the like can be removed from the fabric.
As the cleaning method, a conventionally known cleaning method can be adopted.
In washing, it is preferable to use water in the range of room temperature to 100° C., an anionic soaping agent, or a nonionic soaping agent.

-Drying process (drying after washing)-
The fabric after the washing step is dried. The drying method is not particularly limited, and after dehydrating the washed fabric, it can be dried by a method such as sun drying, a dryer, a heat roll, or an iron.

[Colored material]
The present invention also includes inventions of colored products. The colored product of the present invention is a colored product obtained by the above manufacturing method.

[kit]
A kit that is an embodiment of the present invention is a kit that includes at least a colored composition that is an embodiment of the present invention and a fabric containing polyamide fibers. This coloring kit can be used to color fabrics.
The above kit can be suitably used in a coloring method using an inkjet method using a coloring composition as an ink.

The present invention will be explained in more detail below based on Examples.
The materials, amounts used, proportions, processing details, processing procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the Examples shown below.

[Specific compound and comparative compound (coloring agent)]
The coloring agent used to prepare the coloring composition (inkjet composition) used for coloring the fabric was synthesized as follows.

[Synthesis of compound (B-32) (synthesis example)]
Compound (B-32) was synthesized according to the scheme below.

<Synthesis of compound 2>
To a solution of Compound 1 (129.3 g) purchased from Fuji Film Wako Pure Chemical Industries, Ltd. in dimethylacetamide (360 ml) was added dropwise acetic anhydride (96.4 g) under ice-water cooling, and the mixture was stirred at room temperature for 1 hour. The resulting reaction solution was added dropwise to water (1080 ml), stirred at room temperature for 2 hours, filtered under reduced pressure, washed with water, and dried at 50°C to obtain Compound 2 (156 g). .
¹ H-NMR (Nuclear Magnetic Resonance) data of the obtained Compound 2 is shown below.
^1H -NMR (400MHz, DMSOd6): δ = 10.12 (bs, 1H), 9.27 (bs, 1H), 7.94 (d, J = 2.4Hz, 1H), 6.94 (dd , J=2.4Hz, 8.8Hz, 1H), 6.85 (d, J=8.8Hz, 1H), 2.10 (s, 3H)

<Synthesis of compound 3>
A nitric acid aqueous solution (63.2 g) having a density of 1.38 g/ml was added dropwise to a solution of Compound 2 (93.0 g) obtained above in chloroform (750 ml) under ice-water cooling, and the mixture was stirred at room temperature for 3 hours. 100 ml of water was added dropwise to this solution, and the precipitated solid was collected by filtration under reduced pressure, washed sequentially with chloroform (200 ml) and water (100 ml), and dried at room temperature to form compound 3 (76. 0g) was obtained.
The ¹ H-NMR data of the obtained compound 3 is shown below.
^1H -NMR (400MHz, DMSOd6): δ = 9.76 (bs, 1H), 8.20 (d, J = 2.4Hz, 1H), 7.74 (d, J = 2.4Hz, 1H) ,2.10(s,3H)

<Synthesis of compound 4>
To a methanol (200 ml) dispersion of compound 3 (25.0 g) obtained above, 5% palladium on carbon (2.3 g) and ammonium formate (44 g) were added at room temperature, and the mixture was stirred at 50°C for 2 hours. did. After removing insoluble components from the obtained solution by Celite filtration, about 160 ml of methanol in the obtained filtrate was distilled off under reduced pressure, and the remaining solution was extracted with ethyl acetate (400 ml) and saturated brine (400 ml). . The aqueous phase was re-extracted with ethyl acetate (400 ml), and the organic phases were combined, dried over sodium sulfate, and concentrated under reduced pressure to about 100 g.
After adding dimethylacetamide (100 ml) to the obtained concentrate, isobutyryl chloride (12.6 ml) and pyridine (10.5 ml) were added dropwise under ice-water cooling, and the mixture was stirred at room temperature for 2 hours. The resulting reaction solution was extracted with ethyl acetate (200 ml) and 0.5N hydrochloric acid water (200 ml). The organic phase was washed with an aqueous sodium bicarbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. Compound 4 (21.7 g) was obtained by recrystallizing the residue from ethyl acetate/hexane.
The ¹ H-NMR data of the obtained compound 4 is shown below.
^1H -NMR (400MHz, DMSOd6): δ = 9.95 (bs, 1H), 9.70 (bs, 1H), 9.55 (bs, 1H), 7.38 (d, J = 8.0Hz , 1H), 7.32 (d, J = 8.0Hz, 1H), 6.79 (t, J = 8.0Hz, 1H), 2.79 (hep, J = 6.8Hz, 1H), 2 .13 (s, 3H), 1.12 (d, J=6.8Hz, 6H)

<Synthesis of compound 6>
Magnesium chloride hexahydrate (8.1 g) was added to a solution of Compound 5 (4.5 g) purchased from Tokyo Chemical Industry Co., Ltd. in dimethylacetamide (34 ml) and stirred at room temperature for about 10 minutes. Aqueous sodium (ca65 wt%) (3.6 g) was added to this dispersion, and the mixture was stirred at 40°C for 3 hours. Ethyl acetate (150 ml) and water (150 ml) were added to separate the layers. After removing insoluble matter in the aqueous phase by vacuum filtration, common salt was added to saturate the mixture. This aqueous phase was extracted three times with ethyl acetate (100ml). The organic phases were combined, washed with saturated brine (50 ml), and dried over sodium sulfate. The obtained solution was concentrated under reduced pressure, then dimethylformamide (30 ml) was added and further concentrated. Compound 6 (5.0 g) was obtained by recrystallizing the residue from ethyl acetate/hexane.
The ¹ H-NMR data of the obtained compound 6 is shown below.
^1H -NMR (400MHz, DMSOd6): δ = 9.82 (bs, 1H), 9.49 (bs, 1H), 8.02 (dd, J = 1.6Hz, 4.4Hz, 1H), 7 .52 (dd, J=1.6Hz, 8.0Hz, 1H), 6.83 (bs, 2H), 6.59 (dd, J=4.4Hz, 8.0Hz, 1H)

<Synthesis of compound 7>
A 30 wt % hydrogen peroxide solution (3.4 ml) was added dropwise to a solution of Compound 6 (4.65 g) obtained above in methanol (46.5 ml) at room temperature, and the mixture was stirred at that temperature for 1.5 hours. Water (50 ml) was added to the resulting reaction solution, and after stirring at room temperature for 5 minutes, it was cooled to 0° C., filtered under reduced pressure, and washed with water. Compound 7 (3.9 g) was obtained by drying the obtained solid at 50°C.
The ¹ H-NMR data of the obtained compound 7 is shown below.
¹ H-NMR (400MHz, DMSOd6): δ = 8.55 (dd, J = 2.0Hz, 4.0Hz, 1H), 8.21 (dd, J = 2.0Hz, 8.4Hz, 1H), 8.10 (bs, 2H), 6.81 (dd, J=4.0Hz, 8.4Hz, 1H)

<Synthesis of compound (B-32)>
Compound 7 (3.9 g) and compound 4 (6.1 g) obtained above were dissolved in phosphoric acid (59 ml) at 50°C and cooled to 0°C. Sodium nitrite (1.95 g) was added to the mixture over about 10 minutes, kept at that temperature for 2 hours, and then stirred at room temperature for 1 hour. Subsequently, water (585 ml) was added dropwise to the mixture, and after cooling to 0°C, a 50 wt % aqueous sodium hydroxide solution (44.5 g) was added dropwise at 10°C or lower, and the mixture was stirred at that temperature for 1 hour. The resulting reaction solution was filtered under reduced pressure, washed with water, and dried at 50°C to obtain a crude compound (B-32) (7.0 g).
The obtained crude dispersion in acetonitrile (70 ml) was stirred at 50° C. for 30 minutes, cooled to room temperature, and then filtered under reduced pressure. The obtained crude product was further dispersed in methanol (70 ml), stirred at 50°C for 30 minutes, cooled to room temperature, and filtered under reduced pressure.
The obtained crude product was purified by column (chloroform containing 2 vol% triethylamine, chloroform containing 2 vol% triethylamine/methanol containing 2 vol% triethylamine = 10/1, and chloroform containing 2 vol% triethylamine/methanol containing 2 vol% triethylamine = 5/1). (The mixture was used in turn as a developing solvent.) After that, the mixture was concentrated under reduced pressure to obtain a mixture of compound (B-32) and the triethylamine salt of compound (B-32).
The above mixture was dissolved in water (150 ml) and acidified (pH≈2) with concentrated hydrochloric acid (about 1.2 ml) to precipitate a solid. This was filtered under reduced pressure and thoroughly washed with water to obtain compound (B-32) (2.5 g).
¹ H-NMR data of the obtained compound (B-32) is shown below.
^1H -NMR (400MHz, DMSOd6): δ = 9.59 (bs, 1H), 9.43 (bs, 1H), 8.64 (bs, 1H), 8.58 (d, J = 8.0Hz , 1H), 8.41 (bs, 1H), 8.32 (bs, 1H), 7.21 (bs, 1H), 2.92 (hep, J=6.8Hz, 1H), 2.19 ( s, 3H), 1.13 (d, J=6.8Hz, 6H)

[Synthesis of compound (A-19) (synthesis example)]
Compound (A-19) was synthesized according to the scheme below.

<Synthesis of compound 8>
To a dispersion of compound 3 (5.0 g) obtained above in methanol (50 ml) were added 5% palladium on carbon (0.5 g) and ammonium formate (9.8 g) at room temperature, and at 50°C Stir for hours. After removing insoluble components from the obtained solution by Celite filtration, about 32 ml of methanol in the obtained filtrate was distilled off under reduced pressure, and the remaining solution was extracted with ethyl acetate (100 ml) and saturated brine (100 ml). . The aqueous phase was re-extracted with ethyl acetate (100 ml), and the organic phases were combined, dried over sodium sulfate, and concentrated under reduced pressure.
After adding acetonitrile (30 ml) to the obtained concentrate, ethyl isocyanate (1.40 ml) was added dropwise under ice-water cooling, and the mixture was stirred at room temperature for 1 hour. The resulting reaction solution was extracted with ethyl acetate (100 ml) and 0.5N hydrochloric acid water (100 ml). The organic phase was washed with an aqueous sodium bicarbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. Compound 8 (2.2 g) was obtained by recrystallizing the residue from ethyl acetate/hexane.
The ¹ H-NMR data of the obtained compound 8 is shown below.
¹ H-NMR (400MHz, DMSOd6): δ = 10.15 (bs, 1H), 9.90 (bs, 1H), 8.08 (bs, 1H), 7.60 (d, J = 8.0Hz , 1H), 6.94 (d, J = 8.0Hz, 1H), 6.84 (t, J = 5.4Hz, 1H), 6.71 (t, J = 8.0Hz, 1H), 3 , 11 (dq, J = 5.4Hz, 7, 2Hz, 2H), 2.14 (s, 3H), 1.05 (t, J = 7.2Hz, 1H)

<Synthesis of compound 11>
Magnesium chloride hexahydrate (8.1 g) was added to a dimethylacetamide (50 ml) solution of compound 9 (7.5 g) synthesized by the method described in International Publication No. 2012/058392, and the mixture was stirred at room temperature for about 10 minutes. . Aqueous sodium (ca65 wt%) (3.6 g) was added to this dispersion, and the mixture was stirred at 40°C for 3 hours. Ethyl acetate (500 ml) and water (500 ml) were added to separate the layers. After removing insoluble matter in the aqueous phase by vacuum filtration, common salt was added to saturate the mixture. This aqueous phase was extracted three times with ethyl acetate (200ml). The organic phases were combined, washed with saturated brine (100 ml), and dried over sodium sulfate. After concentrating the obtained solution under reduced pressure, dimethylformamide (30 ml) was added and further concentrated to obtain crude compound 10 (7.5 g).
A 30 wt % hydrogen peroxide solution (3.4 ml) was added dropwise to a solution of this crude product in methanol (75 ml) at room temperature, and the mixture was stirred at that temperature for 1.5 hours. Water (75 ml) was added to the resulting reaction solution, and after stirring at room temperature for 5 minutes, it was cooled to 0°C, filtered under reduced pressure, and washed with water. Compound 11 (6.0 g) was obtained by recrystallizing the obtained solid from methanol.
¹ H-NMR data of the obtained compound 11 is shown below.
^1H -NMR (400MHz, DMSOd6): δ=8.39 (d, J=1.6Hz, 1H), 8.22 (bs, 2H), 7.56 (dd, J=1,6Hz, 9. 2Hz, 1H), 7.35 (d, J=9.2Hz, 1H), 7.18 (bs, 2H)

<Synthesis of compound (A-19)>
Concentrated hydrochloric acid (5.8 ml) was added dropwise at room temperature to a mixture of tetrahydrofuran (7.2 ml)/water (4.8 ml) in which Compound 11 (2.3 g) obtained above was dispersed, and the mixture was heated to 30°C. After stirring for 30 minutes, the mixture was cooled to 0°C. A solution of sodium nitrite (1.03 g) in water (2 ml) was added dropwise to the mixture, and the reaction solution was stirred for 30 minutes while being kept at 0° C., and then sulfamic acid (0.49 g) was added. After stirring this liquid mixture for 5 minutes, compound 8 (2.4 g) obtained above was added, and the mixture was stirred at 0° C. for 1 hour and then at room temperature for 1 hour. Subsequently, water (100 ml) was added dropwise to the mixed solution, and the resulting reaction solution was filtered under reduced pressure, washed with water, and dried at 50°C to obtain a crude form of compound (A-19) (3. 0g) was obtained.
The obtained crude dispersion in acetonitrile (60 ml) was stirred at 50° C. for 30 minutes, cooled to room temperature, and then filtered under reduced pressure.
The obtained crude product was purified by column (2 vol% triethylamine-containing chloroform, 2 vol% triethylamine-containing chloroform/2 vol% triethylamine-containing methanol = 9/1, and 2 vol% triethylamine-containing chloroform/2 vol% triethylamine-containing methanol = 4/1). (The mixture was used in turn as a developing solvent.) After that, the mixture was concentrated under reduced pressure to obtain a mixture of compound (A-19) and the triethylamine salt of compound (A-19).
The above mixture was dissolved in a mixed solvent of water (75 ml)/methanol (10 ml) and acidified (pH≈2) with concentrated hydrochloric acid (about 0.6) to precipitate a solid. This was filtered under reduced pressure and thoroughly washed with water to obtain compound (A-19) (0.91 g).
¹ H-NMR data of the obtained compound (A-19) is shown below.
¹ H-NMR (400 MHz, DMSOd6): δ = 9.79 (bs, 1H), 8.51 (bs, 1H), 8.44 (bs, 2H), 8.02 (bs, 1H), 7. 89 (d, J = 9.0 Hz, 1H), 7.63 (d, J = 9.0 Hz, 1H), 7.49 (bs, 2H), 7.20 (bs, 1H), 3.15 ( q, J=7.2, 2H), 2.19 (s, 3H), 1.08 (t, J=7.2Hz, 3H)

[Synthesis of compound (C-6) (synthesis example)]
Compound (C-6) was synthesized according to the scheme below.

<Synthesis of compound 12>
To a dispersion of compound 3 (5.0 g) obtained above in methanol (50 ml) were added 5% palladium on carbon (0.5 g) and ammonium formate (9.8 g) at room temperature, and at 50°C Stir for hours. After removing insoluble components from the obtained solution by Celite filtration, about 32 ml of methanol in the obtained filtrate was distilled off under reduced pressure, and the remaining solution was extracted with ethyl acetate (100 ml) and saturated brine (100 ml). . The aqueous phase was re-extracted with ethyl acetate (100 ml), and the organic phases were combined, dried over sodium sulfate, and concentrated under reduced pressure.
After adding dimethylacetamide (30 ml) to the obtained concentrate, acetic anhydride (1.69 ml) was added dropwise at room temperature, and the mixture was stirred at 50°C for 1 hour. The resulting reaction solution was extracted with ethyl acetate (100 ml) and 0.5N hydrochloric acid water (100 ml). The organic phase was washed with an aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. Compound 12 (3.1 g) was obtained by recrystallizing the residue from ethyl acetate/hexane.
The ¹ H-NMR data of the obtained compound 12 is shown below.
^1H -NMR (400MHz, DMSOd6): δ = 9.92 (bs, 1H), 9.68 (bs, 2H), 7.34 (d, J = 8.0Hz, 2H), 6.78 (t , J=8.0Hz, 1H), 2.13(s, 6H)

<Synthesis of compound 14>
Magnesium chloride hexahydrate (3.3 g) was added to a solution of Compound 13 (3.66 g) synthesized by a method known in the literature in dimethylacetamide (23 ml), and the mixture was stirred at room temperature for about 30 minutes. Aqueous sodium (ca65 wt%) (1.2 g) was added to this dispersion, and the mixture was stirred at room temperature for 3 hours. Ethyl acetate (200 ml) and water (200 ml) were added to separate the layers. After concentrating the organic phase under reduced pressure, dimethylformamide (30 ml) was added and further concentrated. Compound 14 (4.0 g) was obtained by recrystallizing the residue from ethyl acetate/hexane.
The ¹ H-NMR data of the obtained compound 14 is shown below.
¹ H-NMR (400 MHz, DMSOd6): δ = 9.90 (bs, 1H), 9.64 (bs, 1H), 8.47 (s, 1H), 8.33 (m, 2H), 7. 92 (bs, 2H), 6.51 (m, 3H)

<Synthesis of compound 15>
A 30 wt % hydrogen peroxide solution (1.6 ml) was added dropwise to a methanol (55 ml) solution of Compound 14 (3.23 g) obtained above at room temperature, and the mixture was stirred at that temperature for 3 hours. Water (110 ml) was added to the resulting reaction solution, stirred at room temperature for 5 minutes, cooled to 0°C, filtered under reduced pressure, and washed with water. The obtained solid was dispersed in acetonitrile (70 ml), stirred at 50°C for 30 minutes, cooled to room temperature, and filtered under reduced pressure. Compound 15 (2.1 g) was obtained by drying the obtained solid at 50°C.
The ¹ H-NMR data of the obtained compound 15 is shown below.
^1H -NMR (400MHz, DMSOd6): δ = 9.43 (s, 1H), 8.93 (bs, 2H), 8.45 (m, 2H), 7.53 (m, 3H)

<Synthesis of compound (C-6)>
A dispersion of Compound 12 (1.82 g) obtained above in phosphoric acid (16.5 ml)/water (4.7 ml) was stirred at 50°C for 30 minutes and cooled to 0°C. Sodium nitrite (0.73 g) was added to this mixture over about 5 minutes, and the mixture was stirred at that temperature for 30 minutes. Subsequently, this mixed solution was slowly added to a solution of Compound 15 (1.82 g) in methanol (20 ml) at 0°C, and after 30 minutes at 0°C, the mixture was stirred at room temperature for 1 hour. Water (200 ml) was added to this reaction solution, and the precipitated crystals were filtered under reduced pressure and dried at 50°C to obtain 1.30 g of crude compound (C-6).
The obtained crude product was dispersed in acetonitrile (30 ml), stirred at 50°C for 1 hour, and cooled to room temperature. After filtration under reduced pressure, compound (C-6) (1.18 g) was obtained by drying at 50°C.
¹ H-NMR data of the obtained compound (C-6) is shown below.
¹ H-NMR (400MHz, DMSOd6): δ = 9.33 (s, 1H), 9.09 (d, J = 4.8Hz, 2H), 8.80 (d, J = 2.4Hz, 1H) , 8.49 (m, 2H), 8.20 (d, J = 2.4Hz, 1H), 7.53 (m, 3H), 2.18 (s, 3H), 2.16 (s, 3H )

<Specific compound>
Other specific compounds and comparative compounds used in Examples were synthesized with reference to the above Synthesis Examples.
Each material used to prepare the colored composition is shown below. AB-9 (Acid Blue 9) and DB-86 (Direct Blue 86), which are general-purpose dyes, and Compounds (R-1) to (R-13) are comparative compounds.

<Comparative compound>

[Preparation of colored object (colored sample)]
Colored samples for evaluation were prepared through the following steps.

<Pre-treatment process>
As the coloring fabric, nylon 6 jersey (vertical density: 36 stitches/inch, horizontal density: 36 stitches/inch, basis weight: 231.5 g/m ² , manufactured by Senzosha Co., Ltd.) is a fabric containing polyamide fibers. was used.
A pretreated fabric was obtained by patting the fabric with pretreatment agent A at a squeezing rate of 90% and air drying. Note that pretreatment agent A was prepared by mixing the following materials.
(Pretreatment agent A)
・Gluing agent: Guar gum [manufactured by Niksho Corporation, MEYPRO GUM NP] 2g
・Hydrotrope: Urea [manufactured by Fujifilm Wako Pure Chemical Industries] 5g
・pH adjuster: Ammonium sulfate [manufactured by Fujifilm Wako Pure Chemical Industries] 4g
・Water 89g

<Inkjet process>
(Preparation of inkjet ink)
Inkjet ink was prepared by mixing each component according to the composition below, stirring the resulting mixed solution for 1 hour while heating it at 30 to 40°C, and filtering it under reduced pressure through a microfilter with an average pore size of 0.5 μm. did. Note that the mass % of each component below represents the content (mass %) of each component relative to the total mass of the inkjet ink.
・Sodium salt of the specific compound or comparative compound shown in Tables 1 to 3 5% by mass
・Glycerin [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.] (aqueous organic solvent) 10% by mass
・Diethylene glycol [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.] (aqueous organic solvent) 10% by mass
・Olfine E1010 [manufactured by Nissin Chemical Co., Ltd.] (acetylene glycol surfactant)
1% by mass
・Water 74% by mass

Each inkjet ink obtained in the above (preparation of ink composition) was set in an inkjet printer (manufactured by Dimatics, DMP-2381), and the pretreated ink obtained in the above <pretreatment step> was placed. A solid image was printed on the fabric.

<Post-processing process>
After drying the printed fabric obtained in the above <inkjet process>, steam was applied in a steam process at 100° C. for 30 minutes in saturated steam to fix the colorant to the fibers of the fabric. Thereafter, the obtained fabric was washed with cold water for 10 minutes and with warm water at 60° C. for 5 minutes, and then air-dried. The fabric thus obtained did not lose its color, and a highly concentrated colored sample was obtained.

[Evaluation of colored samples]
<Color>
Each of the obtained colored samples was visually observed to see if it had a desirable cyan color, and the color was evaluated based on the following evaluation criteria. The larger the value of the evaluation standard, the better the cyan. In addition, colorants that exhibit a strong greenish cyan color are generally more technically difficult to synthesize than colorants that exhibit a strong bluish cyan color due to reasons such as difficulty in synthesizing the compound, so the rating is lower than 6. 5 and evaluation 3 relative to evaluation 4 were set according to the following evaluation criteria. An evaluation of 5 or more is preferred.
(Color evaluation criteria)
1: Dark cyan 2: Slightly dark cyan 3: Cyan with a strong bluish tint 4: Cyan with a strong green tint 5: Cyan with a slight blue tint 6: Cyan with a slight green tint 7: Vivid cyan

<Sweat resistance>
The sweat resistance of each of the obtained colored samples was evaluated by the following method. Specifically, each of the obtained colored samples was treated with an acidic artificial sweat solution (pH=5.5) in accordance with the method specified in JIS L0848 (2004).
The color difference ΔEab (*) between each colored sample after treatment with the acidic artificial sweat liquid and each colored sample before treatment was calculated according to the following formula (X), and sweat resistance was evaluated based on the following evaluation criteria. The smaller the value, the smaller the change in color difference before and after the test, indicating superior sweat resistance. An evaluation of 5 or more is preferred.
(Sweat resistance evaluation criteria)
1:15 or more 2:10 or more and less than 15 3:7 or more and less than 10 4:5 or more and less than 7 5:3 or more and less than 5 6:1 or more and less than 3 7:1 or less

(Calculation method of color difference △Eab)
(*): ΔEab=((ΔL ^* ) ² + (Δa ^* ) ² + (Δb ^* ) ² ) ^0.5 formula (X)
Using a spectrodensitometer (manufactured by Xrite, X-rite i1Pro), the CIEL ^* a ^* b ^* color system (International Commission on Illumination Standards (1976)) of each colored sample before and after treatment with the acidic artificial sweat liquid was measured. Lightness L ^* and chromaticity a ^* and b ^* were measured. From this measurement result, the differences ΔL ^* , Δa ^* , and Δb ^* before and after the above test were calculated, and the color difference ΔEab was determined according to the above formula (X).

<Light resistance>
The light resistance of each of the obtained colored products was evaluated by the following method. Specifically, evaluation samples were prepared using each of the obtained colored samples in accordance with ISO 105-B02, and then the samples were irradiated with xenon light for 5 hours using a xenon fade meter. Similarly to the above evaluation of <sweat resistance>, the color difference ΔEab of the evaluation sample was calculated according to the above formula (X), and the light resistance was evaluated based on the following evaluation criteria. The smaller the value, the smaller the change in color difference before and after the test, indicating that the light resistance is excellent. An evaluation of 5 or more is preferred.
(Evaluation criteria for light resistance)
1: 20 or more 2: 15 or more and less than 20 3: 12.5 or more and less than 15 4: 10 or more and less than 12.5 5: 7.5 or more and less than 10 6: 5 or more and less than 7.5 7: 2.5 or more and less than 5

Table 1 shows the evaluation results of Examples 1-1 to 1-12 and Comparative Examples 1-1 to 1-8, and Table 2 shows the evaluation results of Examples 2-1 to 2-14 and Comparative Examples 2-1 to 1-8. Table 3 shows the evaluation results of Examples 3-1 to 3-10 and Comparative Examples 3-1 to 3-3. The specific compounds in Table 1 are the compounds represented by the above general formula (IA), the specific compounds in Table 2 are the compounds represented by the above general formula (IB), and the specific compounds in Table 3 are the compounds represented by the above general formula (IB). The specific compound is a compound represented by the above general formula (IC).
Each notation in Tables 1 to 3 indicates the following.
The "Colorant" column represents the specific compound or comparative compound used in the preparation of the above (inkjet ink).
In the "R1, R2" column, in the specific compound, when R ^1a or R ^2a is selected from the above Group I, it is marked as "A", and when it is selected from the above Group II, it is marked as "B".
The "Y" column represents a substituent represented by Y ^a , Y ^b , or Y ^c in the specific compound. For example, in the case of Example 1-1, it means that the specific compound has two halogen atoms as Y ^a .
The "σp value of Y" column represents the Hammett's substituent constant σp value of the substituent represented by Y ^a , Y ^b , or Y ^c in the specific compound, and the "Σσp" column represents the Hammett's substituent constant σp value of each substituent represented by Y a , Y b , or Y c in the specific compound. It represents the total value of the fundamental constant σp values. For example, in the case of Example 1-1, the Hammett substituent constant σp value of the halogen atom is 0.23, so the “Σσp” column represents 0.46.
The "Requirement 1" column is "A" if the colorant is a compound represented by any of the above general formula (IIA), the above general formula (IIB), or the above general formula (IIC), Cases other than the above were rated "B".
The "Requirement 2" column indicates that in the examples described in Table 1, the colorant is a compound represented by the above general formula (IA), and R ^1a and R ^2a are each independently a methyl group or an ethyl group. , methoxy group, ethoxy group, methylamino group, ethylamino group, or dimethylamino group, it was designated as "A", and cases other than the above were designated as "B". In Tables 2 and 3, the "Requirement 2" column is marked with "-".
The "Requirement 3" column indicates that in the examples described in Table 2, the colorant is a compound represented by the above general formula (IIB), Y ^IIb is a hydrogen atom or the above substituent X, and Y ^IIb- When ² is a hydrogen atom, it is designated as "A", and in cases other than the above, it is designated as "B". In Tables 1 and 3, the "Requirement 3" column is set to "-".
In the "Requirement 4" column, in the examples described in Table 3, the colorant is a compound represented by the above general formula (IIC), and Y ^IIc is a hydrogen atom or Hammett's substituent constant σp value is -0.20 to 0.50, an alkyl group, an aryl group, an alkylthio group, an arylthio group, an alkylcarbonylamino group, an arylcarbonylamino group, an alkylsulfonylamino group, and an arylsulfonylamino group. When the substituent is a substituent selected from the group consisting of, it is designated as "A", and when the substituent is other than the above, it is designated as "B". In Tables 1 and 2, the "Requirement 4" column is marked with "-".
The “Requirement 5” column indicates that in the examples described in Tables 1 to 3, when L ^1a , L ^2a , L ^1b , L ^2b , L ^1c , and L ^2c are carbonyl groups in the specific compound, Cases other than the above were marked as "B".

From the results in Tables 1 to 3, it is clear that when the coloring composition of the present invention is used for coloring fabrics containing polyamide fibers, the resulting colored product has an excellent cyan color, and has excellent sweat resistance and light resistance. was also confirmed to be excellent.

From the results in Table 1, it was confirmed that when the compound represented by general formula (IA) is a compound represented by general formula (IIA), sweat resistance and light resistance are better (Example 1 -1 and Example 1-11).
In the compound represented by general formula (IA), R ^1a and R ^2a each independently represent a group having 2 or less carbon atoms (e.g., methyl group, ethyl group, methoxy group, ethoxy group, methylamino group, ethylamino group). group or dimethylamino group), it was confirmed that the color and light resistance were better (comparison between Example 1-5 and Example 1-4, etc.).
In the compound represented by the general formula (IA), it was confirmed that when L ^1a and L ^2a are carbonyl groups, the color is more excellent (Example 1-10 and Example 1-4). comparison, etc.)

From the results in Table 2, it was confirmed that the effect of the present invention is more excellent when the compound represented by general formula (IB) is a compound represented by general formula (IIB) (Example 2-8 and comparison with other examples, etc.).
The compound represented by the general formula (IB) is a compound represented by the general formula (IIB), and Y ^IIb is a hydrogen atom or a substituent X, and Y ^IIb-2 is a hydrogen atom In this case, the total score of each evaluation was better, and it was confirmed that the effects of the present invention were better (comparison of Examples 2-5, 2-9 to 2-11 with other Examples, etc.).
It was confirmed that in the compound represented by the general formula (IB), when L ^1b and L ^2b are carbonyl groups, the color is more excellent (Example 2-13 and Example 2-14). comparison, etc.)

From the results in Table 3, it was confirmed that when the compound represented by general formula (IC) is a compound represented by general formula (IIC), sweat resistance and light resistance are better (Example 3 -10 and comparison with other examples, etc.).
The compound represented by the general formula (IC) is a compound represented by the general formula (IIC), and Y ^IIc is a hydrogen atom or has a Hammett substituent constant σp value of −0.20 to 0. .50 selected from the group consisting of an alkyl group, an aryl group, an alkylthio group, an arylthio group, an alkylcarbonylamino group, an arylcarbonylamino group, an alkylsulfonylamino group, and an arylsulfonylamino group. In the case of a substituent, the total score of each evaluation was better, and it was confirmed that the effects of the present invention were even better (comparison between Examples 3-8 and other Examples, etc.).
It was confirmed that in the compound represented by the general formula (IC), when L ^1c and L ^2c are carbonyl groups, the light resistance is better (Example 3-7 and Example 3-2). comparison, etc.)

Claims (10)

A coloring composition used for coloring a fabric containing polyamide fibers,
Contains a colorant and water,
The colorant contains at least one selected from the group consisting of a compound represented by general formula (IA), a compound represented by general formula (IB), and a compound represented by general formula (IC). A coloring composition containing.
In general formula (IA), R ^1a and R ^2a each independently represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group, an alkylamino group, an arylamino group, a dialkyl Represents an amino group, diarylamino group, or alkylarylamino group.
M represents a hydrogen atom or a cation.
L ^1a and L ^2a each independently represent a carbonyl group or a sulfonyl group.
Y ^a represents a substituent. p represents an integer from 1 to 4.
However, the compound represented by general formula (IA) satisfies any of the following requirements 1 to 3.
Requirement 1: When R ^1a and R ^2a are each independently selected from Group I consisting of a hydrogen atom, an alkyl group, an aryl group, and a heterocyclic group, and p is 1, then Y ^a Hammett's substituent constant σp value of the substituent is 0.65 to 0.90,
When R ^1a and R ^2a are each independently selected from Group I, and p is an integer of 2 to 4, Hammett's substitution of each of the plurality of substituents represented by Y ^a The total value of the base constant σp values is 0.65 to 0.90.
Requirement 2: One of R ^1a and R ^2a is selected from Group I, and the other of R ^1a and R ^2a is an alkoxy group, aryloxy group, amino group, alkylamino group, arylamino group, dialkylamino group, diarylamino group. and when p is 1, the Hammett substituent constant σp value of the substituent represented by Y ^a is 0.53 to 0. .90,
When one of R ^1a and R ^2a is selected from the group I, the other of R ^1a and R ^2a is selected from the group II, and p is an integer from 2 to 4, a plurality of The sum of Hammett's substituent constant σp values of the substituents represented by Y ^a is 0.53 to 0.90.
Requirement 3: When R ^1a and R ^2a are each independently selected from Group II, and p is 1, the Hammett substituent constant σp value of the substituent represented by Y ^a is 0. 40 to 0.90,
When R ^1a and R ^2a are each independently selected from Group II, and p is an integer of 2 to 4, Hammett's substitution of each of the plurality of substituents represented by Y ^a The total value of the base constant σp values is 0.40 to 0.90.
In general formula (IB), R ^1b and R ^2b each independently represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group, an alkylamino group, an arylamino group, a dialkyl Represents an amino group, diarylamino group, or alkylarylamino group.
M represents a hydrogen atom or a cation.
L ^1b and L ^2b each independently represent a carbonyl group or a sulfonyl group.
^Yb represents a substituent. q represents an integer from 0 to 3.
However, when q is 1, the Hammett substituent constant σp value of the substituent represented by Y ^b is 0.00 to 0.72, and when q is 2 or 3, the The sum of Hammett's substituent constant σp values of the substituents represented by Y ^b is 0.00 to 0.72.
In general formula (IC), R ^1c and R ^2c each independently represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group, an alkylamino group, an arylamino group, a dialkyl Represents an amino group, diarylamino group, or alkylarylamino group.
M represents a hydrogen atom or a cation.
L ^1c and L ^2c each independently represent a carbonyl group or a sulfonyl group.
^Yc represents a substituent. r represents an integer from 0 to 2.
However, when r is 1, the Hammett substituent constant σp value of the substituent represented by Y ^c is -0.30 to 0.50, and when r is 2, multiple The sum of Hammett's substituent constant σp values of the substituents represented by Y ^c is −0.30 to 0.50. The compound represented by the general formula (IA) is a compound represented by the general formula (IIA), and the compound represented by the general formula (IB) is a compound represented by the general formula (IIB). The colored composition according to claim 1, wherein the compound represented by general formula (IC) is a compound represented by general formula (IIC).

In general formula (IIA), R ^1a , R ^2a , M, L ^1a and L ^2a have the same meanings as R ^1a , R ^2a , M, L ^1a and L ^2a in general formula (IA), respectively.
When R ^1a and R ^2a are each independently selected from Group I, Y ^IIa is a substituent having a Hammett's substituent constant σp value of 0.65 to 0.90, such as a cyano group, an alkylsulfonyl a substituent selected from the group consisting of a group, an arylsulfonyl group, an alkylaminosulfonyl group, a dialkylaminosulfonyl group, an arylaminosulfonyl group, a diarylaminosulfonyl group, and an alkylaminosulfonyl group,
When one of R ^1a and R ^2a is selected from Group I and the other of R ^1a and R ^2a is selected from Group II, Y ^IIa has a Hammett substituent constant σp value of 0.53 to 0. 90, which is an alkylaminosulfonyl group, a dialkylaminosulfonyl group, an arylaminosulfonyl group, a diarylaminosulfonyl group, an alkylarylaminosulfonyl group, an aminosulfonyl group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, A substituent selected from the group consisting of a trifluoromethyl group and a dialkylphosphonate group,
When R ^1a and R ^2a are each independently selected from Group II, Y ^IIa is a substituent having a Hammett substituent constant σp value of 0.40 to 0.90, an alkylaminosulfonyl group, dialkylaminosulfonyl group, arylaminosulfonyl group, diarylaminosulfonyl group, alkylarylaminosulfonyl group, aminosulfonyl group, cyano group, alkylsulfonyl group, arylsulfonyl group, trifluoromethyl group, dialkylphosphonate group, dialkylphosphine oxide group, A substituent selected from the group consisting of an alkylcarbonyl group, an alkoxycarbonyl group, an alkylsulfinyl group, an arylsulfinyl group, and a 4-pyridyl group.
In general formula (IIB), R ^1b , R ^2b , M, L ^1b and L ^2b have the same meanings as R ^1b , R ^2b , M, L ^1b and L ^2b in general formula (IB), respectively.
Y ^IIb and Y ^IIb-2 are each independently a hydrogen atom or a substituent X,
The substituent X is a halogen atom, formyl group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, aminocarbonyl group, alkylaminocarbonyl group, dialkylaminocarbonyl group, arylaminocarbonyl group, diarylamino carbonyl group, alkylaminocarbonyl group, cyano group, alkylsulfonyl group, arylsulfonyl group, alkylaminosulfonyl group, dialkylaminosulfonyl group, arylaminosulfonyl group, diarylaminosulfonyl group, alkylaminosulfonyl group, aminosulfonyl group, Alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, alkylthio group, arylthio group, amino group, alkylamino group, dialkylamino group, arylamino group, diarylamino group, alkylarylamino group, alkylcarbonylamino selected from the group consisting of arylcarbonylamino group, alkylsulfonylamino group, arylsulfonylamino group, trifluoromethyl group, dialkylphosphonate group, dialkylphosphine oxide group, alkylsulfinyl group, arylsulfinyl group, and 4-pyridyl group is a substituent.
However, when one of Y ^IIb and Y ^IIb-2 is a hydrogen atom and the other is the substituent X, the Hammett substituent constant σp value of the group represented by the substituent X is 0.00. ~0.72, and when both Y ^IIb and Y ^IIb-2 are the substituent X, the sum of Hammett's substituent constant σp values of the two substituents X is 0.00 to 0.72. It is.
In general formula (IIC), R ^1c , R ^2c , M, L ^1c and L ^2c have the same meanings as R ^1c , R ^2c , M, L ^1c and L ^2c in general formula (IC), respectively.
Y ^IIc is a hydrogen atom or a substituent having a Hammett substituent constant σp value of -0.30 to 0.50, which is an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio A substituent selected from the group consisting of alkylcarbonylamino, arylcarbonylamino, alkylsulfonylamino, and arylsulfonylamino groups. The coloring agent is a compound represented by the general formula (IA),
The colored composition according to claim 1, wherein R ^1a and R ^2a each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group, a methylamino group, an ethylamino group, or a dimethylamino group. The coloring agent is a compound represented by the general formula (IIB),
The colored composition according to claim 2, wherein Y ^IIb is a hydrogen atom or the substituent X, and Y ^IIb-2 is a hydrogen atom. The coloring agent is a compound represented by the general formula (IIC),
Y ^IIc is a hydrogen atom or a substituent having a Hammett substituent constant σp value of -0.20 to 0.50, which is an alkyl group, an aryl group, an alkylthio group, an arylthio group, an alkylcarbonylamino group, The colored composition according to claim 2, wherein the substituent is selected from the group consisting of an arylcarbonylamino group, an alkylsulfonylamino group, and an arylsulfonylamino group. The colored composition according to claim 1, wherein L ^1a , L ^2a , L ^1b , L ^2b , L ^1c , and L ^2c are carbonyl groups. The colored composition according to any one of claims 1 to 6, which is an inkjet ink. A method for producing a colored product, comprising the step of applying the colored composition according to any one of claims 1 to 6 to a fabric containing polyamide fibers by an inkjet method. A colored product produced by the production method according to claim 8. A kit comprising the colored composition according to any one of claims 1 to 6 and a fabric containing polyamide fibers.