JPS61272270A - Disazo compound - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (M is H or alkali metal; Dz is residue of benzene- or naphthalene-based diazo component; R<1> is H or alkyl; R<2> and R<3> are each H, alkyl, alkoxy, halogen or -SO3M; X is aromatic or aliphatic divalent residue). EXAMPLE:A compound of formula II. USE:Dyes for dyeing in a range blue-red to red-violet, etc., cellulose fibers such as cotton, rayon or hemp and nitrogen-contg. fibers such as polyamide, wool or silk. Capable of dyeing cellulose fibers under the pH condition in dyeing polyester fibers. PREPARATION:For example, a coloring matter of formula III and a compound of formula H2N-X-NH2 are condensed each other in a molar ratio of 2 to 1, the resultant disazo compound is subjected to condensation with a compound of formula IV in such an amount as to be 2 moles for mole of the compound of the formula H2N-X-NH2.

Description

DETAILED DESCRIPTION OF THE INVENTION (a) Object of the Invention (a) Field of Industrial Application The present invention relates to a new disazo compound used as a dye for cellulosic fibers and nitrogen-containing fibers.

(b) Conventional technology Conventionally, when dyeing cellulose fibers, reactive dyes are used, and acid binders such as sodium carbonate, potassium carbonate, and sodium hydroxide, as well as sodium chloride and sulfuric acid are used.
In the presence of an electrolyte such as IJum, at a temperature of 10 or more,
A method is adopted in which the test is carried out under conditions of 00°C or lower.

However, in recent years, cellulose fibers and other fibers, especially /
In order to dye cellulose/polyester mixed fibers (hereinafter simply referred to as "dry fibers"), the demand for blended fabrics with polyester fibers is increasing. It was necessary to apply different dyes and dyeing conditions to the fibers.

This is because the dyes and dyeing conditions for dyeing polyester fibers are significantly different from those for cellulose fibers. That is, in order to dye polyester fibers, it was necessary to use disperse dyes and dye them at a temperature of about 130°C.

For example, if the C/P fibers mentioned above were to be dyed in the same process, it would be necessary to dye them using two different dyes, a combination of a reactive dye and a disperse dye. was there. In other words, in order to dye the reactive dye sufficiently on the cellulose fiber side, it is necessary to use an acid binder to dye the cellulose fiber side.
However, the presence of an acid binder accelerates the decomposition of the disperse dye, resulting in insufficient dyeing of the disperse dye to the polyester fiber. On the other hand, in order to dye the disperse dye on the polyester fiber side, high temperature conditions (usually 130°C) are required.
However, at high temperatures under the above-mentioned conditions, hydrolysis of the reactive dye is promoted, and dyeing of cellulose fibers is significantly inhibited. Therefore, such C/P
When dyeing fibers, a two-bath method is generally used in which one fiber, cellulose or polyester, is dyed and then the other fiber is dyed in a separate bath.

Problems to be Solved by the Invention The present invention seeks to provide a disazo compound capable of dyeing cellulose fibers under the same conditions as when dyeing polyester fibers with disperse dyes.

(b) Structure of the Invention (a) Means for Solving the Problems The above problems could be solved by the disazo compound of the present invention having a specific molecular structure.

That is, the disazo compound of the present invention has the general formula [wherein,
M represents a hydrogen atom or an alkali metal, Dz represents all benzene or naphthalene-based diazo component residues R
1 represents a hydrogen atom, R represents an alkyl group, R and R represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or -So, M (M represents a hydrogen atom or an alkali metal), and X represents an aromatic Represents all divalent group or aliphatic residues. ] It is a compound shown by.

In the disazo compound represented by the general formula [■] of the present invention, examples of the alkali metal represented by M include sodium, potassium, etc., and examples of the alkyl group represented by R1゜R2 and R include a methyl group and an ethyl group. , butyl group, etc., and the alkoxy group represented by R2 and R include methoxy group, ethoxy group, etc.
The diazo component residue represented by Dz includes a phenyl group or a 7-tyl group substituted with a sulfonic acid group, methyl group, methoxy group, etc., and the divalent residue represented by X includes: Ethylene group, l, 3-nolopyrene a, 1,4
Examples include aliphatic groups such as -butylene group and hexamethylene group, or phenylene or naphthylene groups substituted with methyl group, methoxy group, carboxyl group, sulfonic acid group, chlorine atom, etc.

The disazo compound represented by the general formula (1) can be produced as follows.

For example, the 2 molar proportion of the dye represented by the general formula (If) (wherein M and Dz are the same as defined above) and the following formula (111]% formula % () (wherein X is the same as defined above) A 1 molar proportion of the compound represented by is condensed to form a disazo compound represented by the following formula %.

Next, by condensing the disazo compound represented by the general formula (IV) with 2 molar proportions of the compound represented by (wherein M, R, R, and R are the same as defined above), the forefoot general formula ( The disazo compound of 1) can be produced.

The disazo compound of the present invention produced in this way is
It can itself be used as a dye.

Examples of fibers that can be dyed with the disazo compound of the present invention include cellulose fibers such as cotton, viscose rayon, Kiepra ammonium 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 disazo compound of the present invention, dyes necessary for dyeing non-cellulose fibers, such as disperse dyes described in Co1our 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 disazo compound of the present invention, for example, the disazo compound represented by the above general formula C1) and the dye bath during dyeing may be adjusted to pH 5-5.
Buffers necessary to maintain the temperature at 10% (for example, acids such as carbonic acid, phosphoric acid, acetic acid, citric acid, and sodium salts or potassium salts of these acids, singly or in mixtures, usually 0.5 to 5%)
(approximately 0 VA), and electrolyte (chloride) if necessary.
IJum or sodium sulfate, etc., usually 1 to 150
Prepare a dye bath to which Vl, grade) is added, add cellulose fibers to this dye bath, and dye at a temperature of 100 to 150 °C for 30 to 5
Good dyeing can be achieved by heating for 0 minutes.

In addition, in order to dye blended fabrics, blended knitted fabrics, etc. that are manufactured by mixing cellulose fibers with other fibers such as bori ester fibers, a disazo compound represented by the above general formula (I) of the present invention may be used. And the above Co1our Index
By adding the listed disperse dye to the above dye bath, cellulose fibers and polyester fibers can be dyed simultaneously by a one-bath, one-stage method.

In addition, when dyeing blended fabrics, blended knitted fabrics, etc., as described above, a one-bath two-step method is used in which one of the fibers is dyed first, and then the other fiber is dyed in the same bath. Furthermore, a two-bath method may be used in which the dyeing method using the disazo 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. It is also possible to adopt the law.

Examples Hereinafter, the method of the present invention will be explained in more detail with reference to Examples and dyeing examples, but the present invention is not limited to the following Examples.

Example 1 2 molar proportions of a monoazo dye represented by the following structural formula and 1 molar proportion of p-phenylenediamine were condensed in an aqueous medium at 30 to 40°C to produce a disazo compound represented by the following structural formula, and the reaction solution was Inside 3-(
After adding 2 molar proportions of β-hydroxyethyl)sulfonylaniline sulfate and condensing at 90°C, salting out with potassium chloride resulted in the following structural formula (shown in the form after liberation) and the analysis value by visible light absorption. A disazo compound having the following was obtained.

5O2C2H40SO3H [λmax 5 1 7 nm (water)] This disazo compound 0.2P, Glauber's salt 16p, Na2)f as a buffering agent
f04.12H20o, 4g- and KH2PO4
0,1? Add 10% of unmercerized cotton knitted fabric to a dye bath prepared by adding 200% of water to 7%. It takes 30 minutes to
The temperature was raised to 20°C, dyed at the same temperature for 60 minutes, washed with water, soaped, washed with water, and dried to obtain a bluish-red dyed product. The degree of dyeing of this dye was very good, and the dyed product obtained was extremely dense and had good light fastness and chlorine fastness.

Example 2 A disazo compound represented by the following structural formula Ct was produced by condensing 2 molar proportions of a monoazo dye represented by the following structural formula and 1 molar proportion of ethylenediamine in an aqueous medium at 30 to 40°C. Inside 3-(
2 molar proportions of β-hydroxyethyl)sulfonylaniline sulfate were added, the pH of the reaction solution was adjusted to 6 with NaOH, and the mixture was condensed at 90°C, followed by spray drying to give the following structural formula (shown in free acid form). A disazo compound having the following analytical values was obtained.

SO□C2H40S03H [λmax 540 nm (water)] This disazo compound 0.2f, Glauber's salt 16?, Na2HPO412H200.5f and KH2PO as a buffer
40.02? Add 101 gold of unmercerized cotton knitted fabric to a dye bath prepared by adding 200 grams of
The temperature was raised to 0° C. and dyed at the same temperature for 30 minutes, followed by washing, soaping, washing, and drying to obtain a bluish-red dyed product.

This dyeing bath had a pH of 8 before and after dyeing. The dyed product obtained was extremely dense and had good light fastness and chlorine fastness.

Dyeing Example 1 The disazo compound 0.2y-1 produced in Example 1, the anthraquinone dye represented by the structural formula 0.27, and Glauber's Salt 12? ,
A blended fabric of polyester/cotton = 50:50 was added to a dyebath prepared by adding Na2HPO412H200,4f and KH2PO40,IP as buffering agents to 200% of water.
The temperature was raised to 130° C. over 30 minutes, dyed at the same temperature for 60 minutes, washed with water, soaped, washed with water, and dried to obtain a bluish red dyed product with good same color property. This dye bath had a pH of 8 before and after dyeing. In addition, the dyeing property was very good, and the dyed product obtained was extremely thick and had good reed, light fastness, and chlorine fastness. Examples 3 to 24 A method similar to the method described in Example 1. The analytical values of each compound obtained above and the results of dyeing the cotton cloth are shown in Table 1).

(c) Effects of the invention The disazo compound of the invention can exhibit the following effects.

(1) It is excellent as a dye for various fibers, especially cellulose fibers and nitrogen-containing fibers, especially the former.

(ii) Since cellulose fibers can be dyed under the same dyeing conditions as when polyester fibers are dyed with disperse dyes, it is Excellent as a dye for cellulose fibers.

Claims (1)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, M represents a hydrogen atom or an alkali metal, and D
z represents a benzene or naphthalene-based diazo component residue, R^1 represents a hydrogen atom or an alkyl group, and R
^2 and R^3 represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or -SO_3M (M represents a hydrogen atom or an alkali metal), and X represents an aromatic or aliphatic divalent residue. represent. ] A disazo compound represented by