JPH0482029B2 - - Google Patents

Description

[Detailed description of the invention]

INDUSTRIAL APPLICATION FIELD The present invention relates to a novel trisazo compound. BACKGROUND ART In recent years, there has been an increasing demand for blended fabrics of cellulose fibers and other fibers, particularly blended fabrics with polyester fibers (hereinafter simply referred to as C/P fibers). Traditionally, when dyeing cellulose fibers, reactive dyes are used in the presence of acid binders such as sodium carbonate, potassium carbonate, and sodium hydroxide, and electrolytes such as sodium chloride and sodium sulfate.
The dyeing process is carried out at a pH of 10 or higher and a temperature of 100°C or lower.When dyeing polyester fibers, disperse dyes are used and dyeing is carried out at a temperature of about 130°C. When dyeing,
A two-bath method is generally used in which one fiber of cellulose or polyester is dyed and then the other fiber is dyed in a separate bath. However, in order to simplify the dyeing process, the above C/
If P fibers were to be dyed in the same process (one-bath method), two different dyes would be used in combination, a reactive dye and a disperse dye. When used, it is necessary to use an acid binder to raise the pH to 10 or higher in order to sufficiently dye the reactive dye on the cellulose fiber side, but the presence of an acid binder accelerates the decomposition of the disperse dye, The dyeing of the disperse dye to the polyester fiber is insufficient, and high temperature conditions (usually 130°C) are required to dye the disperse dye to the polyester fiber side, but under the high temperature mentioned above, There were problems such as accelerating the hydrolysis of reactive dyes and significantly inhibiting the dyeing of cellulose fibers. Problems to be Solved by the Invention The purpose of the present invention is to provide a trisazo compound that can dye cellulose fibers under the pH and dyeing conditions when dyeing polyester fibers with disperse dyes. be. Means for Solving the Problems The present invention is based on the general formula [] (In the formula, -M represents a hydrogen atom or an alkali metal, -R ⁰ represents a hydrogen atom or a carboxyl group, and -R ¹ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a carboxyl group or a sulfonic acid group. , -R ² is a hydrogen atom, a lower alkyl group,
represents a lower alkoxy group, an acetylamino group or a sulfonic acid group, -R ³ represents a lower alkyl group or a lower alkoxy group, -R ⁴ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or an acetylamino group, - P is a halogen atom or -
Represents SO ₂ R ⁵ , -Q is a halogen atom, a cyano group,
Represents a nitro group or _-SO2R5 group, -W represents a halogen atom or ^-R5 , ^-R5 represents a lower alkyl group, m represents an integer of 1 to 3, and n ^represents 0 or 1. and Ring A and Ring B represent a benzene ring or a naphthalene ring. ) The gist of this is the trisazo compound shown in the following. In the trisazo compound represented by the general formula [] of the present invention, examples of the alkali metal represented by -M include lithium, sodium, potassium, etc., and -R ¹ , -R ² , -R ³ , -R ⁴ and -The lower alkyl group represented by R ⁵ has 1 to 4 carbon atoms.
The lower alkoxy groups represented by -R ¹ , -R ² , -R ³ and -R ⁴ include alkoxy groups having 1 to 4 carbon atoms, -P, -Q
Examples of the halogen atom represented by -W include a fluorine atom and a chlorine atom.

As [Formula],

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Examples include [Formula]. The trisazo compound represented by the general formula [] can be produced by the following method. For example, general formulas [], [] and []

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^A compound ^{represented by the formula} Perform the coupling twice and use the following general formula [] (In the formula, -R ⁰ , -R ¹ , -R ² , -R ³ , -R ⁴ , m, ring A and ring B are the same as defined above). On the other hand, the following formulas [] and []

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[Formula] (In the formula, n, -P, -Q and -W are the same as defined above, and Hal represents a halogen atom.) A compound represented by the following general formula [] is condensed in an aqueous medium. (In the formula, n, -P, -Q and -W are the same as defined above.) A compound represented by the following is produced. Next, the trisazo compound of the general formula [] is prepared by coupling the diazonium compound of the general formula [] with a diazonium compound obtained by diazotizing the diazo compound of the general formula [] in a water-acetic acid medium. can be manufactured. Actions and Effects The trisazo compound of the present invention thus produced can itself be used as a dye. Examples of fibers that can be dyed with the trisazo compound of the present invention include cellulose fibers such as cotton, viscose rayon, cuprammonium rayon, and hemp. Furthermore, it can also be applied to dyeing nitrogen-containing fibers such as polyamide, wool, and silk. Furthermore, cellulose fibers in mixed fibers such as polyester, triacetate, polyacrylonitrile, polyamide, wool, silk, etc. containing cellulose fibers can of course be dyed well. In the fiber dyeing method using the trisazo compound of the present invention, dyes necessary for dyeing non-cellulose fibers, such as disperse dyes listed in the Color Index (3rd edition), are added to the dye bath at the same time. In addition, it can be dyed. When dyeing cellulose fibers using the trisazo compound of the present invention, for example, the trisazo compound represented by the above general formula [] and the buffer necessary to maintain the dye bath at pH 5 to 10 during dyeing are used. agent (for example, acids such as carbonic acid, phosphoric acid, acetic acid, citric acid, and sodium salts or potassium salts of these acids, usually about 0.5 to 5.0 g/mixture) and, if necessary, electrolyte (sodium chloride or sulfuric acid). A good dyeing process is achieved by preparing a dye bath containing sodium, etc. (usually about 1 to 150 g/approx.), adding cellulose fibers to this dye bath, and heating them at a temperature of 100 to 150 degrees Celsius for 30 to 50 minutes. It can be carried out. In addition, blended fabrics manufactured by adding other fibers such as polyester fibers to cellulose fibers,
In order to dye mixed woven and knitted fabrics, etc., a trisazo compound represented by the above general formula [] of the present invention and a disperse dye listed in the above Color Index are added to the dye bath to dye cellulose fibers. Polyester fibers can be dyed at the same time using a one-bath, one-step method. In addition, when dyeing blended fabrics, blended knitted fabrics, etc., as described above, the one-bath two-step method, in which one of the fibers is dyed and then the other fiber is dyed in the same bath, is used. may be applied, and furthermore,
It is also possible to adopt a two-bath method in which the dyeing method using the trisazo compound of the present invention and the dyeing method for fibers other than cellulose fibers are combined to dye cellulose fibers and other fibers from separate baths. . EXAMPLES Hereinafter, the method of the present invention will be specifically explained using examples, but the present invention is not limited to the following examples. Example 1 38.3 g of 2-naphthylamine-3,6,8-trisulfonic acid was dissolved in 2-methoxy-5-methylaniline.
A monoazo compound produced by diazotizing and coupling with 13.7g of 2-methoxy-5-methylaniline in a conventional manner was further diazotized and coupled with 13.7g of 2-methoxy-5-methylaniline to obtain the following structural formula. A disazo compound represented by: On the other hand 1
-amino-8-hydroxynaphthalene-3,6-
31.9g of disulfonic acid and 2,4,6-trifluoro-
16.9 g of 5-chloropyrimidine was condensed at 0°C to form the following structural formula: A compound represented by is prepared, a diazo solution obtained by diazotizing the above disazo compound with a water-acetic acid system is added to the reaction solution, coupling is performed at pH 7 using KOH, and salting out with potassium chloride results in the following. A trisazo compound represented by the structural formula (free acid form) was produced. [Maximum absorption wavelength, λmax (water): 592 nm] 0.2 g of the trisazo compound of the present invention represented by the above structural formula, 16 g of Glauber's sulfate, and Na ₂ HPO ₄ as a buffering agent.
Add 0.4 g of 12H ₂ O and 0.1 g of KH ₂ PO ₄ to 200 ml of water to adjust the pH to 7.
10 g was added, the temperature was raised to 120°C over 30 minutes, dyed at the same temperature for 60 minutes, washed with water, soaped, washed with water, and dried to obtain a greenish dark blue dyed product. The degree of dyeing of this dye was very good, and the dyed product obtained was extremely dense, and the light fastness, chlorine fastness, and sweat fastness to daylight were all good. Example 2 25.3 g of aniline-2,5-disulfonic acid was
A monoazo compound produced by diazotizing and coupling with 13.7 g of methoxy-5-methylaniline in a conventional manner is further diazotized and coupled with 18.0 g of 2-methoxy-5-acetylaminoaniline in a conventional manner to form the following structural formula: A disazo compound represented by: On the other hand 2
The following structural formula is a condensate of 23.9 g of -amino-5-hydroxynaphthalene-7-sulfonic acid and 20.9 g of 2,4,6-trichloro-5-cyanopyrimidine. This was diazotized with the previously produced disazo compound and coupled at pH using NaOH, and then the reaction solution was spray-dried to obtain the trisazo of the present invention represented by the following structural formula (free acid form). A series compound was produced. [Maximum absorption wavelength, λmax (water): 587 nm] 0.2 g of the trisazo compound of the present invention represented by the above structural formula, 16 g of Glauber's sulfate, and Na ₂ HPO ₄ as a buffering agent.
10 unsilced cotton knitted fabrics were added to a dyebath prepared by adding 0.5 g of 12H ₂ O and 0.02 g of KH ₂ PO ₄ to 200 ml of water.
g, the temperature was raised to 130℃ over 30 minutes, dyed at the same temperature for 30 minutes, washed with water, soaped, washed with water,
After drying, a dark blue dyed product was obtained. This dyeing bath had a pH of 8 before and after dyeing. The resulting dyed product is extremely dense and has excellent light fastness, chlorine fastness, and sweat resistance.
The fastness to sunlight was good in all cases. Example 3 2-methoxy-5- used in Example 2
13.7g of methylaniline to 1-naphthylamine-7
- The following structural formula (free acid form) was prepared according to the production method described in Example 2 except that 22.3 g of sulfonic acid was used.
A trisazo compound of the present invention represented by: [Maximum absorption wavelength, λmax (water): 586 nm] 0.2 g of the trisazo compound of the present invention represented by the above structural formula _0.2g of monoazo dye _{shown by}
Add 0.1 g of KH ₂ PO ₄ to 200 ml of water and add 10 g of blended fabric of polyester/cotton = 50:50 to a dye bath prepared.
The temperature was raised to 130°C over 30 minutes, and after dyeing at the same temperature for 60 minutes, water washing, soaping, water washing, and drying were performed to obtain a dark blue dyed product with good color constancy. This dyeing bath had a pH of 8 before and after dyeing. Furthermore, the dyeing property was very good, and the dyed product obtained was extremely rich, and the light fastness, chlorine fastness, and sweat-sunlight fastness were all good. Example 4 According to the manufacturing method described in Example 2, the following first
The trisazo compounds of the present invention shown in the table (in free acid form) were produced. Using the obtained trisazo compound of the present invention,
Cotton fabrics were dyed according to the method described in Example 2 and the results are shown in Table 1 below.

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Claims (1)

[Claims] 1. General formula [] (In the formula, -M represents a hydrogen atom or an alkali metal, -R ⁰ represents a hydrogen atom or a carboxyl group, and -R ¹ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a carboxyl group or a sulfonic acid group. , -R ² is a hydrogen atom, a lower alkyl group,
represents a lower alkoxy group, an acetylamino group or a sulfonic acid group, -R ³ represents a lower alkyl group or a lower alkoxy group, -R ⁴ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or an acetylamino group, - P is a halogen atom or -
-Q represents ^a halogen atom, cyano group, nitro group or ^-SO5R5 group, -W represents a halogen atom or _{-R5 ,} ^-R5 represents ^a lower alkyl group , m represents an integer of 1 or more and 3 or less, n represents 0 or 1, and ring A and ring B represent a benzene ring or a naphthalene ring. 2. The trisazo compound according to claim 1, wherein [formula] in general formula [] is represented by [formula] (wherein -M is the same as defined above). 3. The trisazo compound according to claim 1, wherein [formula] in general formula [] is represented by [formula] (wherein -R ⁶ represents a lower alkyl group).