JPH0269571A - Anthraquinone compound and process for dyeing or printing textile material with the same compound - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [R1 and R2 are H or (substituted) lower alkyl; R is H, (substituted) lower alkyl, cyclohexyl, phenyl, alkylcarbonyl, alkylsulfonyl or arylsulfonyl; B is (substituted) phenylene or (sulfo-substituted) naphthylene; Z is vinyl or -CH2CH2L (L is group eliminable by the action of alkali; V is -O- or -S-; l is 0-2; A is group of formula II (R3-R5 are H, methyl, etc.; W1 is -O-, -S-, etc.; m1 is 0 or 1; m2 is 0-4; m is 0-2), etc.] in the form of a free acid. EXAMPLE:The compound of formula III. USE:A dye capable of dyeing a material containing OH group and carboxylic acid amide group in bluish red to red color. PREPARATION:The objective compound can be produced by condensing the compounds of formulas IV-VI with cyanuryl chloride or fluoride.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to novel acytraquinone compounds in the field of dyeing or printing aMA materials as reactive dyes.

The conventional technique disclosed in Japanese Unexamined Patent Publication No. 46-8884, for example, is no longer able to respond to the following formula. For example, even when looking at dyeing performance, which is one of the basic performance requirements for dyes, many unsatisfactory points have come to be recognized.

Means for Solving the Problems In order to find a new acytraquinone compound that has performance that can meet the sophistication of needs as described above, the present inventors investigated the pigment matrix, the type and number of reactive groups, and As a result of intensive studies on the types of linking groups and linking sites connecting these groups, the inventors discovered a compound that has specific performance by combining specific groups, and completed the present invention.

That is, the present invention discloses an anthraquinone compound represented by the following general formula (1) in the form of a free acid.

Problems to be Solved by the Invention Due to recent changes in the technological and economic situation in the demanding industry, existing fiber-reactive anthraquinone compounds cannot meet all the needs of the demanding industry. R2 is independently hydrogen or lower alkyl which may have a substituent, R is hydrogen or lower alkyl which may have a substituent, leclohexyl, phenyl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl represents. B is methyl, ethyl, methoxy, ethoxy, chloro,
phenylene optionally substituted with one or two substituents selected from the group of bromo, sulfo, carboxy and nitro, or naphthylene optionally substituted with sulfo;
2 is vinyl or -CH, CH, L (L represents a group that is eliminated by the action of an alkali), ■ is 10 - or -3
- represents a linking group. 1 represents 0.1 or 2, and A represents an optional lower alkyl having the formula (2). ), ml is 0
Or 1, m! is 0 or an integer from 1 to 4 and m is 0.1
Or represents 2. 1 or formula (8) (wherein, R,, RhR
, and R11 are each independently hydrogen, methyl, ethyl, methoxy, ethoxy, chloro, bromo or carboxy, W
! is -o --s --NRlg - or -NR,sC
represents O- (Rlm and Rls represent hydrogen or a lower alkyl group which may have a substituent), n represents 0 or an integer from 1 to 4, and nl represents 0 or 1; ) or formula (4), K (where R,, R and R are independently hydrogen, methyl, ethyl, methoxy, ethoxy, chloro, bromo or carboxy, Wl is -o--s+, -NR・-or-N
R, Co-(R and R7 are hydrogen or a substituent,
p represents 0.1.2 or 8. ) or formula (5) % formula % (5) (in the formula, q represents an integer from 2 to 6) 2
represents a valence group, X is fluoro, chloro (in the formula, RIF s
R18 and R19 independently represent lower alkyl which may have a substituent or phenyl which may have a substituent. ) or formula (9) (R14 and R1 each independently represent hydrogen or optionally substituted lower alkyl, phenyl, naphthyl or benzyl.

) or formula (7) (wherein R1- is hydrogen or lower alkyl which may have a substituent, B1 is selected from the group of methyl, ethyl, methoxy, ethoxy, chloro, bromo, sulfo, carboxy and nitro) phenylene optionally substituted with one or two substituents or naphthylene optionally substituted with sulfo, Zl is vinyl or -CH,
CH, Ll (L represents a group that is eliminated by the action of an alkali) or formula (8) (where Y is hydrogen, cyano, carbamoyl, halogen,
Represents hydroxy, vinyl, sulfo, carboxy or lower alkyl which may have a substituent. ) represents a group represented by The present invention provides an anthraquinone compound represented by the following and a method for dyeing or printing delicate materials using the anthraquinone compound.

In the general formula (1), when R1 and R are lower alkyl which may independently have a substituent, such a group is, for example, the group shown in JP-A-59-176855. Groups fall under this category. Preferably R1 is hydrogen, methyl or ethyl and the R-rich is hydrogen or methyl.

(In the formula, the bond shown with ** means a bond that leads to the -N- group.) etc. ξ can be specifically, unsubstituted, or methyl or methoxy! #-substituted phenylene or unsubstituted or sulfo-substituted β-naphthylene is preferred.

When Z is -CM, CH, or L, groups known to have the ability to be eliminated by the action of an alkali are applicable, such as sulfate, thiosulfate, acetoxy, and chloro. It will be done. Preferable example 2 is β-sulfur-1-toethyl, in which vinyl may be partially mixed.

When R is lower alkyl, cyclohexyl, phenyl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl which may have a substituent, examples of the substituent include methyl, ethyl, methoxy, ethoxy, chloro, bromo, 1 from the group of acetylamino, propionyl, nitro, cyano, carbamoyl, carboxy, hydroxy, sulfate and sulfo;
Or preferably two are selected.

Preferred examples of R include hydrogen, methyl, ethyl, propyl, 1so-propyl, butyl, 1so-butyl, 2-carboxyethyl, 2-sulfoethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-hydroxyethyl, 2-
Sulfatoethyl, cyclohexyl, acetyl, propionyl, benzoyl, 2-8- or 4-sulfobeshizoyl, 2-8- or 4-carboxybenzoyl, 2-8
- or 4-chlorobenzoyl, 2-3- or 4-methoxybenzoyl, 2-8-or g! 4-methylbenzoyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, 2-8- or 4-sulfophenylsulfonyl,
2-8- or 4-carboxyphenylsulfonyl, 2-
8- or 4-chlorophenylsulfonyl, 2-8- or 4-methoxyphenylsulfonyl, 2-8- or 4-methylphenylsulfonyl, phenyl, 2-8- or 4-
Sulfophenyl, 2-8- or 4-carboxyphenyl, 2-8- or 4-chlorophenyl, 2-8- or 4-
Examples include methoxyphenyl and 2-8- or 4-methylphenyl.

Particularly preferred among these are hydrogen and alkyl having 1-4 carbon atoms.

As A, among the divalent groups represented by formulas (2) to (5), in particular, ml in formula (2) is 0.1 or 2, m and ml are independently 0 or 1, and Wl is -o--NH- or -NHCO-, n in formula (8) is 1 or 2, W! is -o--NH- or -N)ICO-, and when p in formula (4) is 0.1 or 2,
It is preferable that q in formula (5) is 2.8 or 4.

X represents fluoro, chloro, or a group represented by formulas (6) to (9), and in formula (6), RI4 and R11
The optionally substituted lower alkyl represented by 1 is, for example, 1 or 2 selected from the group of alkoxy, sulfo, carboxy, drooxy, chloro, phenyl, and sulfate having 1 to 4 carbon atoms. Preferably, lower alkyl having 1 to 4 carbon atoms is optionally substituted with a substituent.

Among them, methyl, ethyl, n-propyl, 1so-propyl, n-butyl, 180-butyl, 5
Examples include eC-butyl, β-hydroxyethyl, β-sulfatoethyl, β-sulfoethyl, β-methoxyethyl, and β-carboxymethyl.

Furthermore, the optionally substituted phenyl represented by R, 4 and Rli includes, for example, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, and chloro. Phenyl optionally substituted with one or two substituents selected from the group is preferred.

Among them, phenyl, 2-8- or 4-sulfophenyl, 2-8- or 4-carboxyphenyl,
2-8- or 4-chlorophenyl, 8.4- 8.5-
or 8,6-disulfophenyl.

Further, the optionally substituted naphthyl represented by R14 and R16 includes, for example, droxy, carboxy, sulfo, alkyl having 1 to 4 carbon atoms, and 1 to 4 carbon atoms.
Naphthyl optionally substituted with 1,2 or 8 substituents selected from alkoxy and chloro having 4 carbon atoms is preferred.

Among them, particularly preferred are 2 +, 8 +, 4 +,
5.6-. 7- or 8-sulfo-1-naphthyl, 1
+, 5 +, 6 +, 7- or 8-sulfo-2-
Naphthyl, 2.4- 5.7- 6.8-. 4,84.
7- 8.8- 4.6- 8.7- or 8.6-disulfo-2-naphthyl, 4.6.8- 2.4.7- or 8,6.8-trisulfo-1-naphthyl, 1.5.7-
4.6.8- or 8.6.8-) disulfo-2-naphthyl and the like.

Furthermore, the optionally substituted benzyl represented by R14 and RIB is selected from the group consisting of, for example, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, and chloro. , benzyl optionally substituted with one or two substituents is preferred.

Particularly preferred among these are benzyl, 2-8- or 4-sulfobenzyl, and the like.

In addition, in formula (7), when R1- is hydrogen or lower alkyl which may have a substituent, such a group includes, for example, the group shown in JP-A-59-176855. do. Preferably R1. is hydrogen, methyl or ethyl. Examples of B1 include groups similar to B,
Examples of zl include the same groups as 2.

In addition, in formula (8), R11 and R1- are methyl s
Preferably, RII is methyl, ethyl, propyl, butyl, hydroxyethyl, hydroxypropyl, methoxyethyl, ethoxyethyl, 2-diethylaminoethyl, 8-diethylaminopropyl, carboxymethyl, or carboxyethyl.

Among these, alkyl having 1 to 4 carbon atoms is particularly preferred.

Further, in formula (9), it is particularly preferable that Y is hydrogen, carbamoyl or carboxy.

In particular, when X is chloro, and when R14 is a group represented by formula (6), R14 is chloro, methyl or ethyl, R1
It is preferable that 1 is phenyl which may have a substituent as shown in the above example.

Moreover, it is preferable that ■ is 1$-.

The compounds of the present invention may exist in the form of free acids, but are preferably alkali metal salts or alkaline earth metal salts,
Examples include sodium and potassium salts.

The compound of the present invention has the following formula (11-(IrisylHN-B-5o, -Za) (wherein 1%R%R,,R,,A1B%V and Z have the above-mentioned meanings). , W represents a group capable of temporarily protecting amino such as acetyl, or hydrogen.), cyanuric chloride or fluoride;
When is a group such as acetyl that can temporarily protect the 7[) group, a hydrolysis reaction is subsequently carried out in the presence of an alkali or acid to convert W into hydrogen. , an organic dye residue (dye matrix) of the compound of formula (1) can be produced. Next, add this and the formula α2 compound, α3 where necessary (04)
(Ise (in the formula s R14s RII s RHs RIf s
R111s RII s Bl sz+ and Y has the above-mentioned meaning) It can be produced by a conventional method using a compound represented by the following.

That is, first, a compound of the formula αl and a compound of the formula are subjected to a known Ullmann condensation reaction, and at that time, the compound of the formula (1) used can be produced.

Formula α [Compounds include, for example, l-amino-4-bromoanthraquinone-2-sulfonic acid, l-amino-4-
Bromoanthraquinone-2,6- or 2,7-disulfonic acid, 1-amino-4-bromoanthraquinone-2,5
, 8-) disulfonic acid, 1-methylamino-4-bromoanthraquinone-2-sulfonic acid, 1-ethyla[no-4-bromoanthraquinone-2-sulfonic acid, l-propylamino-4-bromoanthraquinone-2-sulfone Examples include acids.

Examples of the compound of formula (11) include 2.4.6-)dimethyl-8-mercapto-5-aminobenzenesulfonic acid, 2-mercapto-4-aminobenzene-1,6-disulfonic acid, and 2-mercapto- 5-Aminobenzene-1
．． 4-disulfonic acid, 5-mercapto-2-amino-4
-methoxybenzenesulfonic acid, 1-mercapto-8-
Aminocyclohexane, 1-mercapto-4-aminocyclohexane, 2- or 4-methyl-1-mercapto-
8-aminocyclohexane, 6,5-dimethyl-1-mercapto-8-aminocyclohexane, 1-mercapto-4-N-methyl, N-ethyl or N-β-carboxyethylaminocyclohexane, 4-mercaptomethyl-2- Amino-5-methylbenzenesulfonic acid, 4- or 5-mercaptomethyl-2-aminobenzenesulfonic acid, 6-mercaptomethyl-8-amino-2,4-dimethylbenzenesulfonic acid, 6-mercaptomethyl-2-
Amino-8-methoxybenzenesulfonic acid, 8-mercaptomethyl-2-amino-6-methylbenzenesulfonic acid, 4-mercaptomethyl-2-amino-5-methoxybenzenesulfonic acid, 6-mercaptomethyl-2-a [
Nobenzene-1゜4-disulfonic acid, 4-mercaptomethyl-2-amino-5-ethylbenzenesulfonic acid, 1
-mercapto-2-7 main noethane, 1-mercapto-3
-Aminopropane, 1-mercapto-4-a[butane, 1-mercapto-6-aminohexane, -disulfonic acid, 4-mercapto-4-aminobiphenyl-8-sulfonic acid, 1-mercapto-8 or 4-amino benzene,
2-Mercapto-4 or 6-azanobenzenesulfonic acid, 1-mercap)-4-N-(β-carboxyethyl)
A[Nobenzene, 4-(β-mercaptoethylamino)
Aniline, 4 (r-mercaptopropylamino)
Aniline, 4-(β-mercaptoethylamino)aniline-2 or 8-sulfonic acid, 4-(β-mercaptoethylamino)aniline-2,5-disulfonic acid, 4-(8-
Mercabutophenyl-2 is 8-sulfonic acid-14
-(4-mercaptophenylamino)aniline-2 or 8-phenylaminocoaniline, 4-((4'-mercapto-8-sulfo)phenylaminocoaniline, amino]aniline-2 or 8-sulfonic acid, 4- Nocoaniline-2 or 8-sulfonic acid, 4-mercaptoethoxy)-
Aniline-2 or 5-sulfonic acid, 4-(β-mercaptoethoxy)-2-methylaniline-8 or 5-sulfonic acid, 4-(β-mercaptoethylcarbamoyl)aniline-2-sulfonic acid, 5-(β -Mercaptopropionylamino)aniline-2 or 4-sulfonic acid, carbamoylgoaniline-2-sulfonic acid, 4-[(8-mercapto-4-sulfo)phenylcarbamoyl]-aniline-2-sulfonic acid, 4-minocoaniline- 2 or 5
-Sulfonic acids, etc., and compounds in which hydroxy is substituted for mercapto.

The anthraquinone compound produced according to the present invention can be made into a liquid product by removing inorganic salts and adding stabilizers or dyeability improvers as necessary, or this liquid product or reaction solution can be evaporated. For example, it can be made into a powder product by spray drying, and it can also be made into a liquid or powder product through salting out separation by addition of an electrolyte using a generally known method.

The anthraquinone compounds according to the invention can be used as fiber-reactive dyes and can dye textile materials, for example materials containing hydroxy groups or carboxylic acid amide groups.

Hydroxy group-containing materials are natural or synthetic hydroxy group-containing materials, such as cellulose fiber materials or their regenerated products and polyvinyl alcohol.

Preferably, the cellulosic fiber material is cotton, but also other vegetable fibers such as linen, hemp, jute and ramie fibers. Regenerated cellulose fibers are, for example, viscose, stable and filament viscose.

Materials containing carbonamide groups are, for example, synthetic and natural polyamides and polyurethanes, in the form of specialized fibers, such as wool and other animal hairs, silk, leather, polyamide-6,6
, polyamide-6,4t-lyamide-11 and polyamide-4.

For dyeing, methods depending on the reactive group of the delicately reactive dye can be applied.

For example, in the case of cellulosic fibers, dyeing is carried out using the dye according to the invention and an acid binder such as caustic soda, sodium carbonate, phosphate, silicate or sodium bicarbonate. The dyeing method can be selected depending on the delicate nature and physical shape.
For example, an exhaustion method, a printing method, a cold dopa method, a dopa chia method, a bu method, etc. can be employed.

In the case of exhaustion method, sodium carbonate, trisodium phosphate,
It is carried out at relatively low temperatures in a dye bath containing mirabilite or common salt in the presence of an acid binder such as caustic soda. In the case of printing processes, thickening agents or emulsifying thickening agents such as, for example, sodium alginate or starch ethers and sodium carbonate, sodium bicarbonate, caustic soda, sodium triphosphate, sodium trichloroacetate or the corresponding potassium or alkaline earth compounds are used. With an alkaline or alkali-releasing agent, optionally with the addition of customary printing aids or dispersants, such as urea, it is applied onto the fibers, dried and, in particular, heat treated in the presence of steam. It can be dyed by attaching it. In the case of Coldopa, Dopa, Thea, and B dyeing, caustic soda alone or in combination with sodium silicate, sodium carbonate, or trisodium phosphate is used as an acid binder, and in some cases, mirabilite or common salt is added. Dyeing can be achieved by padding the fibers at room temperature with the addition of a solubilizing agent or penetrating agent, winding them up into a roll, leaving them for 8 hours or overnight, followed by washing with water and drying.

The compound of the present invention is characterized in that it exhibits excellent performance on delicate materials, and is particularly suitable for dyeing cellulose-based pongee. It exhibits high exhaustion and fixation rates, excellent pill door, washability, level dyeing and washability, and does not affect dyeability even if there are slight fluctuations in dyeing conditions such as temperature, bath ratio, salt concentration, etc. It has characteristics such as almost no oxidation, and has excellent light resistance, sweat resistance, light resistance, sweat resistance, acid hydrolysis resistance 1, washing resistance, salt accumulation resistance, etc.

Next-ζ The present invention will be explained in more detail by way of examples. In the text, the part indicates the heavy Ik part.

λmax　540nm An acitraquinone compound represented by was obtained.

This one-nthraquinone compound can be used in the above-mentioned method, especially in the method of exhaustion dyeing cellulose fiber materials, such as cotton, and has good fastness such as light fastness, sweat light fastness, and sweat resistance, as well as exhaust rate and fixation rate. , gives a bluish-red dyed product with excellent build-up properties.

28.7 parts of trimethyl-6-sulfophenylthio)anthraquinone-2-sulfosic acid and 9.8 parts of cyanuric chloride were condensed at 10-20°C under weak acidity in an aqueous medium, and then 1
-aminobenzene-8-β-sulfur 1-toethylsulfone (4.6-) Dimethyl-6 -sulfophenylthio)acitraquinone-2-sulfonic acid, cyanuric chloride, 1-7 minobenzene-8-β-sulf 1-
Instead of toethyl sulfone, use No. 1 in the following table in that order. Using the compounds in columns 2 and 8, corresponding anthraquinone compounds were obtained in the same manner as in Example 1. The color tones of these compounds on cotton are as shown in Section 4.

Example 8 28.7 parts of trimethyl-5-sulfophenylthio)anthraquinone-2-sulfonic acid, 9.8 parts of cyanuric chloride, and 14. One part was sequentially condensed in an aqueous medium by a conventional method, and then reacted with 8.7 parts of 8-aminobenzenesulfonic acid at 50-110°C under weak acidity, and salted out to form the free acid. It provides a vivid one-color dyeing which is excellent in fastness such as undercoatability, exhaustion rate, fixation rate, build-up property, etc.

Example 4 1-amino-4-(8-amino-2°4.6
'-)dimethyl-6-sulfophenylthio)anthraquinone-2-sulfonic acid, 1-aminobenzene-8-β-
Instead of sulf-1-toethylsulfone and 8-aminobenzenesulfonic acid, in that order, 1. Using the compounds in columns 2 and 8, the corresponding anthraquinodi compounds were obtained in the same manner as in Example 1. The color tones of these compounds on cotton are shown in column 4.

(Margin below) 1max 5401m An acitraquinone compound represented by was obtained.

This acitraquinone compound can be used in the above-mentioned method, particularly in the method of exhaust dyeing cellulose fiber materials, such as cotton, to exhibit good light fastness, sweat light fastness, and sweat resistance. 28.7 parts of acid, 9.8 parts of cyanuric chloride, and 14.1 parts of 1-a[nobenzene-8-β-sulfur]-1-toethylsulfone were sequentially condensed in an aqueous medium by a conventional method, and then 4. 5 parts under weak acidity at 60 to 70°C and salted out to obtain an acytraquinone compound represented by the following formula in the form of a free acid.

This anthraquinone compound can be used in the above-mentioned method, especially in the method of exhaustion dyeing delicate cellulose materials such as cotton, and has good fastness such as light fastness, sweat resistance, light fastness, and sweat resistance, as well as exhaustion rate, fixation rate, and build-up property. It gives an excellent bright blue dyed product.

Practical example 6 4.6-)dimethyl-5-sulfophenylthio)anthraquinone-2-sulfonic acid, 1-aminobenzene-8-
In place of β-sulfate ethyl sulfoxy and pyridine, in that order, 1. Using the compounds in columns 2 and 8, corresponding anthraquinone compounds were obtained in the same manner as in Example 1. The color tones of these compounds on cotton are shown in column 4.

(The following is a blank space) Staining example 1 Anthraquinone compound described in Example 1 0.1.0.8
, and 0.6 parts each in 200 parts of water, and 20 parts of mirabilite
1 part, add 10 parts of cotton, and raise the temperature to 60°C. Then, after 80 minutes had passed, 8 parts of soda carbonate was added and dyed at the same temperature for 1 hour. After dyeing, washing with water and soaping were carried out to obtain a bluish red dyed product having excellent fastness to sunlight, sweat and sunlight, and good pill door and washability.

This compound also has excellent solubility, and has good level dyeing and dyeing reproducibility.

Staining example 2 Anthraquinone compound described in number 7 of Example 2 0.8
Dissolve 1 part in 200 parts of water, add 20 parts of mirabilite, and add 1 part of cotton.
Add 0 parts and raise the temperature to 60°C. Then, after 20 minutes,
Add 8 parts of tribasic sodium phosphate. Dye for 1 hour at that temperature. After dyeing, washing and soaping were performed to obtain a bluish-red dyed product with excellent color fastness.

Staining Example 3 Anthraquinone compound 0.1.0.8 described in Example 8
, and 0.6 parts each were dissolved in 200 parts of water, and 80 parts of mirabilite was added.
1 part, add 10 parts of cotton, and raise the temperature to 70°C. Then, after 80 minutes had elapsed, 8 parts of soda carbonate was added and dyed at the same temperature for 1 hour. After dyeing, washing with water and soaping were carried out to obtain a bluish red dyed product having excellent fastness properties, especially fastness to sunlight, sweat and sunlight, and good build-up properties.

This compound also has excellent solubility, and has good level dyeing and dyeing reproducibility.

Staining Example 4 Anthraquinone compound described in number 7 of Example 4 0.8
Dissolve 1 part in 200 parts of water, add 80 parts of mirabilite, and add 1 part of cotton.
Add 0 parts and raise the temperature to 70°C. Then, after 20 minutes,
Add 8 parts of tribasic sodium phosphate. Dye for 1 hour at that temperature. After dyeing, washing and soaping were performed to obtain a bluish-red dyed product with excellent color fastness.

Dyeing Example 5 Color paste composition Anthraquinone compound described in Example 1 6 parts Urea 5
50 parts Sodium alginate (5X) base glue Heat
Hot water 26 parts Baking soda 2
Part balance: 18 parts Print the color paste with the above composition on the mercerized wire broad,
After intermediate drying, steam at 100°C for 5 minutes,
Finish by washing with hot water, soaping, washing in place, and drying.

In this way, a bluish-red print with excellent color fastness was obtained.

Dyeing Example 6 Color paste composition Anthraquinone compound described in Example 6 5 parts Urea 5
50 parts sodium alginate (5%) base glue
26 parts of hot water 2 parts of baking soda 18 parts of balance Color paste with the above composition was printed on mercerized cotton broadcloth, intermediately dried and steamed at 110°C for 6 minutes, washed in place, soaped, washed in hot water, and dried. and finish.

In this way, a bluish-red print with excellent color fastness was obtained.

(Margin below)

Claims (1)

[Claims] 1) In the form of a free acid, the following general formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (1) [In the formula, R_1 and R_2 each independently have hydrogen or a substituent. R represents hydrogen or lower alkyl which may have a substituent, cyclohexyl, phenyl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl. B is phenylene optionally substituted with one or two substituents selected from the group of methyl, ethyl, methoxy, ethoxy, chloro, bromo, sulfo, carboxy and nitro, or naphthylene optionally substituted with sulfo; Z is vinyl or -CH_2CH_2L (L represents a group that is eliminated by the action of an alkali), V is -O- or -
S- represents a linking group. l is 0, 1 or 2, and A is formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (2) {In the formula, R_3, R_4 and R_5 are independently hydrogen methyl, ethyl, methoxy, ethoxy, Chloro, bromo or carboxy, W_1 is -O-, -S-, -NR_6
- or -NR_7CO- (R_6 and R_7 represent hydrogen or lower alkyl which may have a substituent),
m_1 represents 0 or 1, m_2 represents 0 or an integer from 1 to 4, and m represents 0, 1 or 2. } or formula (3) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (3) {In the formula, R_8, R_9, R_1_0 and R_1_1 each independently represent hydrogen, methyl, ethyl, methoxy, ethoxy, chloro, bromo or carboxy, W_2 is -o-,
-s-, -NR_1_2- or -NR_1_3CO-(
R_1_2 and R_1_3 represent hydrogen or a lower alkyl group which may have a substituent. ), where n is 0
or an integer from 1 to 4; n_1 represents 0 or 1; }
Or formula (4), ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (4) (In the formula, p represents 0, 1, 2 or 3.) or formula (5
) -(CH_2)_q-(5) (In the formula, q represents an integer from 2 to 6.) Represents a divalent group represented by: etc. ▼ (6) (R_1_4 and R_1_5 each independently represent hydrogen or optionally substituted lower alkyl, phenyl, naphthyl or benzyl.) or formula (7) ▲ Numerical formula,
There are chemical formulas, tables, etc.▼(7) (In the formula, R_1_6 is hydrogen or lower alkyl which may have a substituent, B_1 is methyl, ethyl, methoxy,
phenylene optionally substituted with one or two substituents selected from the group of ethoxy, chloro, bromo, sulfo, carboxy and nitro, or naphthylene optionally substituted with sulfo, Z_1 is vinyl or -CH_2CH
_2L_1 (L_1 represents a group that is eliminated by the action of an alkali.) or formula (8) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (8) (In the formula, R_1_7, R_1_8 and R_1_9 each independently represent a substituent. represents lower alkyl that may have a substituent or phenyl that may have a substituent) or formula (9) ▲ Numerical formula, chemical formula, table, etc. ▼ (9) (In the formula, Y is hydrogen, cyano , carbamoyl, halogen,
Represents hydroxy, vinyl, sulfo, carboxy or lower alkyl which may have a substituent. ) represents a group represented by ]An anthraquinone compound represented by. 2) The compound according to claim 1, wherein R_2 is hydrogen or methyl. 3) The compound according to claim 1 or 2, wherein R_1 is hydrogen, methyl or ethyl. 4) The compound according to any one of claims 1 to 8, wherein Z is vinyl or β-sulfatoethyl. 5) The compound according to any one of claims 1 to 4, wherein the divalent group A is represented by formula (2), m_2 is 0, 1 or 2, and m and m_1 are each independently 0 or 1. 6) The compound according to any one of claims 1 to 4, wherein divalent group A is represented by formula (8), and n is 1 or 2. 7) The compound according to any one of claims 1 to 4, wherein the divalent group A is represented by formula (4) and p is 0, 1 or 2. 8) The compound according to any one of claims 1 to 4, wherein the divalent group A is represented by formula (5) and q is 2, 3 or 4. 9) The compound according to any one of claims 1 to 8, wherein X is chloro. 10) Any one of claims 1 to 8, wherein X is represented by formula (6), R_1_4 is hydrogen, methyl or ethyl, and R_1_5 is optionally substituted phenyl or optionally substituted naphthyl. Compounds described. 11) The compound according to any one of claims 1 to 8, wherein X is represented by formula (7), R_1_6 is hydrogen, methyl or ethyl, and Z_1 is vinyl or β-sulfatoethyl. 12) X is represented by formula (8), and R_1_7 and R_1_
9. A compound according to claim 1, wherein 8 is independently methyl or ethyl and R_1_9 is alkyl having 1 to 4 carbon atoms. 13) The compound according to any one of claims 1 to 8, wherein X is represented by formula (9) and Y is hydrogen, carbamoyl or carboxy. 14) The compound according to any one of claims 1 to 18, wherein V is -s-. 15) A method for dyeing or printing a fiber material, comprising using an anthraquinone compound represented by the general formula (1) according to claim 1.