JPS6230158A - Disazo compound - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I(M is H or alkali metal; Dz is benzene or naphthalene based diazo component residue; R<1> is H or alkyl; R<2> and R<3> are H, alkyl, alkoxy, halogen or -SO3M; X is aromatic or aliphatic bifunctional residue). USE:A dye for dyeing cellulosic fibers to orange-scarlet color capable of dyeing the fibers under the same conditions as those for dyeing polyester fibers, etc. PREPARATION:Two mol dyestuff expressed by formula II is condensed with 1 mol compound expressed by the formula H2N-X-NH2 to give a disazo derivative expressed by formula III, which is then condensed with 2 mol compound expressed by formula IV.

Description

[Detailed description of the invention] (,) Purpose of the invention The present invention relates to novel disazo compounds.

(b) Field of Application of the Invention The cis-sazo compound of the present invention can be used as a dye for cellulose fibers, etc., and in particular, it can easily dye cellulose fibers under the same dyeing conditions as those used when dyeing polyester fibers, etc. with disperse dyes. Since it can be dyed into a mixture of cellulose fibers and other fibers such as polyester, it is advantageously used for dyeing mixed fibers of cellulose fibers and other fibers such as polyester.

(b) Prior art Conventionally, when dyeing cellulose fibers, reactive dyes were used, including sodium carbonate, potassium carbonate, and hydroxide).
A method is employed in which the reaction is carried out in the presence of an acid binder such as IJum and an electrolyte such as sodium chloride or sodium sulfate at a pH of 10 or higher and a temperature of 100° C. or lower.

However, in recent years, demand for blended fabrics of cellulose fibers and other fibers, especially polyester fibers, has increased, and such cellulose/, f! Lyester mixed fiber (hereinafter simply "C"
/P fiber". ] To dye the
Dyes and dyeing conditions for cellulose fibers, l I
It was necessary to apply different dyes and dyeing conditions to the J ester 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 a disperse dye and dye at a temperature of about 130°C.

For example, if the above C/'P fibers were to be dyed in the same process, two different dyes would be used in combination of a reactive dye and a disperse dye, which would cause several problems. there were. For example, in order to dye the reactive dye sufficiently on the cellulose fiber side, use an acid binder to dye -1.
The presence of the acid binder accelerates the decomposition of the disperse dye, resulting in insufficient dyeing of the disperse dye to the polyester fibers. On the other hand, high-temperature conditions (usually 130°C) are required to dye disperse dyes on the ester fiber side, but the high-temperature conditions mentioned above accelerate the hydrolysis of reactive dyes and cause cellulose fibers to be dyed. The dyeing will be significantly inhibited. Therefore, when dyeing such C/P 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. It will become.

(c) Problems to be Solved by the Invention The present invention aims to easily dye cellulose fibers under conditions similar to those used when dyeing polyester fibers etc. with disperse dyes, etc., and under conditions such as temperature. Therefore, it is an object of the present invention to provide a dye compound which is excellent as a raw material for cellulose fibers and can be advantageously used when dyeing mixed fibers of cellulose and polyester by a one-bath one-step method.

(b) Structure of the Invention (a) Means for Solving the Problems As a result of repeated research in order to solve the above-mentioned problems, the present inventor has found that the object can be achieved with a disazo compound having a specific chemical structure. was completed.

That is, the disazo compound of the present invention has the general formula (wherein,
M represents a hydrogen atom or an alkali metal, D2 represents a benzene or naphthalene-based diazo component residue, and R
1 represents a hydrogen atom or an alkyl group, R2 and R
3 represents a hydrogen atom, an alkyl group, an alkoxy group, a halodane atom, or ~503M, and X represents an aromatic or aliphatic divalent residue. ) is a disazo compound represented by

In the cis-sazo compound represented by the general formula (1) of the present invention, examples of the alkali metal represented by M include sodium, potassium, etc., and examples of the alkyl group represented by R and R2 include a methyl group, an ethyl group, Examples of the alkoxy group represented by R include butyl groups, etc.
Examples of the diazo component residue represented by D include a methoxy group, an ethoxy group, and a sulfonic acid group, a methyl group,
Examples of divalent residues represented by X include phenyl or naphthyl groups substituted with methoxy groups, etc., and examples of divalent residues represented by aliphatic groups such as, or methyl groups,
Examples include a methoxy group, a carboxyl group, a sulfonic acid group, a phenylene group or a naphthylene group which may be substituted with a chlorine atom, etc.

The cis-sazo compound represented by the general formula (1) can be produced as follows. That is, for example, it is represented by the general formula % formula % () (wherein, M t Dz is the same as the above definition), and the 2 mole ratio of 2 O dyes and the following formula % formula % () (wherein, X is the same as the above definition). Same as the definition.) 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 (■) with 2 molar proportions of the compound represented by the following general formula (wherein M, R, R, and R are the same as defined above), the front leg general formula is obtained. The disazo compound (I) 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 cellulosic fibers such as cotton, viscose rayon, Keepra ammonium rayon, and hemp.

Furthermore, it can be used for 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 cis-sazo 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. 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 (1) and the dye bath during dyeing may be
Buffers necessary to maintain the temperature at 0 (e.g. carbonic acid, phosphoric acid,
Acids such as acetic acid, citric acid, and sodium salts or potassium salts of these acids, singly or as a mixture, usually 0.5 to 5.0
(approximately 11/11) and, if necessary, an electrolyte (sodium chloride or sodium sulfate, etc., usually 1 to 150
Adjust the dye bath by adding J7/7), add the cellulose fibers to the dye bath, and dye at a temperature of 100 to 150℃ for 30~
Good dyeing can be achieved by heating for 50 minutes.

In addition, in order to dye blended fabrics, blended knitted fabrics, etc. produced by adding other fibers such as polyester fibers to cellulose fibers, the disazo compound represented by the above general formula (1) of the present invention and the above-mentioned Co1our Index
By adding the listed disperse dye to the above dye bath, cellulose fibers and flash ester 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, the conventional one-bath two-step method of dyeing one fiber and then dyeing the other fiber in the same bath is used. Furthermore, a two-bath method 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

(b) Examples, etc. Further details will be given below with reference to Examples and dyeing examples.

Example 1 A disazo compound represented by the structural formula was produced by condensing 2 molar proportions of the monoazo dye represented by the structural formula and 1 molar proportion of p-phenylenediamine in an aqueous medium at 30 to 40°C. ni3-(
A 2 molar proportion of β-hydroxyethyl)sulfonylaniline sulfate was added and condensed at 90°C, followed by salting out with potassium chloride to produce a disazo compound having the following structural formula and visible light absorption analysis value in free acid form.

0.2 g of a disazo compound shown by this structural formula, 1 g of mirabilite
6II, Na2HPO412H200°4 as a buffering agent
Add 40.1 g of KH2PO and 200 g of water to -
10g of unmercerized cotton knitted fabric was added to the dye bath prepared in step 7, and the temperature was raised to 120°C over 30 minutes.
After dyeing for minutes, wash with water, saw, wash and dry.
An orange dyed product was obtained. The degree of dyeing was very good, the dyed product obtained was extremely deep, and the light fastness and chlorine fastness were good.

Example 2 A disazo compound represented by the structural formula was produced by condensing 2 molar proportions of the monoazo dye represented by the structural formula with 1 molar proportion of ethylene and diamine in an aqueous medium at 30 to 40°C. −(
After adding 2 moles of β-hydroxyethyl sulfonylanili 7 sulfate ester and combining at 90°C, spray drying was performed to obtain a disazo compound having the following structural formula and visible light absorption analysis value in free acid form. Manufactured.

[λmax 501 nm (water)] 0.2 g of the disazo compound represented by this structural formula, 1 g of mirabilite
6II, Na2HPO412H200,5 as buffering agent
,! i' and KH2PO40.02g in water 200+t
/Add 1 part of unmercerized cotton stockinette to the prepared dye bath.
0.9, the temperature was raised to 130° C. over 30 minutes, dyed at the same temperature for 30 minutes, washed with water, soaped, washed with water, and dried to obtain a scarlet dyed product. This dyeing bath is used before dyeing.
The pH was 8 throughout. The dyed product obtained was extremely dense and had good light fastness and chlorine fastness of 1 and 9.

Dyeing Example 1 The disazo compound 0.2.9 obtained in Example 2 and the monoazo dye represented by the structural formula 0.2.9. Glauber's salt 12I, Na2HPO412H200,41/and K as buffering agent
Add 10 g of polyester/cotton-50:50 blend fabric to a dye bath prepared by adding H2PO40,19 to water 2001/
was heated 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 scarlet dyed product with good color consistency.

This dye 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 and chlorine fastness were good.

Examples 3 to 1 Combination using various compounds as each compound represented by the general formula (n), (I[I) and (1'l/),
Other than that, the reaction was carried out in accordance with the method in Example 1 to produce various disazo compounds shown in Table 1 below. The visible light absorption analysis values of each disazo compound and the results of dyeing cotton cloth were as shown in Table 1.

(c) Effect of the invention The disazo compound of the present invention has the following effects.

(i) Excellent dyeability of cellulose fibers and nitrogen-containing fibers, particularly cellulose fibers.

(11) Since cellulose fibers can be dyed under the same dyeing conditions such as - and temperature when dyeing polyester fibers with disperse dyes, etc., it is especially possible to dye mixed fibers of cellulose and polyester etc. in one bath and one step. Excellent as a dye for cellulose fibers when dyeing by the method.

Patent applicant: Mitsubishi Chemical Industries, Ltd. 1・'51゛Mountain 1～゛ □Nino

Claims (1)

[Claims] (1) General formula▲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,
R^2 and R^3 represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or -SO_3M, and X represents an aromatic or aliphatic divalent residue. ) A disazo compound represented by