JPS61200174A - Disazo compound - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I (M is H, or alkali metal; group shown by the formula II is benzene ring or naphthalene ring which may be replaced). EXAMPLE:A compound shown by the formula III. USE:Red dye for cellulosic yarn such as cotton, rayon, etc. The cellulosic yarn can be dyed under pH and dyeing conditions when polyester yarn is dyed with disperse dye. PREPARATION:For example, 1-hydroxy-3-sulfonic acid-6-aminonaphthalene is condensed with 1, 3, 5-trifluoro-s-triazine in an aqueous medium at <=0 deg.C at 4 pH, to give a compound shown by the formula IV. Then, this compound is condensed with a compound shown by the formula V to give a compound shown by the formula VI. Then, a compound shown by the formula VII is disazotized in an aqueous medium and coupled with the compound shown by the formula VI.

Description

[Detailed description of the invention] Industrial applications The present invention relates to novel disazo compounds.

Conventionally, when dyeing cellulose fibers, reactive dyes are used to dye cellulose fibers at pH 10 in the presence of acid binders such as sodium carbonate, potassium carbonate, sodium hydroxide, and electrolytes such as sodium chloride and sodium sulfate. Above, temperature 10
A method is adopted in which the process is carried out under conditions of 0°C or lower.
゛However, in recent years, cellulose fibers and other fibers,
In particular, the demand for blended fabrics with polyester fibers, etc. is increasing, and such cellulose/polyester mixed fibers (hereinafter simply c)
In order to dye the fibers), it was necessary to apply the dyes and dyeing conditions to the cellulose fibers and the dyes and dyeing conditions to the polyester fibers, respectively. This is because the dyes and dyeing conditions for dyeing polyester fibers are significantly different from those for cellulose fibers. In other words, in order to dye polyester fibers, disperse dyes are used and the temperature is approximately 73θ℃.
This is because it needed to be dyed.

For example, if the c/'p fibers mentioned above were to be dyed in the same process, two different dyes would be used in combination with a reactive dye and a disperse dye, which would pose several problems. Rarely.

For example, in order to sufficiently dye reactive dyes on the cellulose fiber side, it is necessary to use an acid binder to raise the pH to 10 or higher.The presence of an acid binder promotes the decomposition of disperse dyes, and Dyeing to the fibers becomes insufficient. On the other hand, in order to dye the polyester fiber side with disperse dyes, high temperature conditions (usually 30°C) are required;
At high temperatures under H, hydrolysis of reactive dyes is promoted, and dyeing of cellulose fibers is significantly inhibited. Therefore, when dyeing such C/''PII1.m, 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. It becomes.

Problems to be Solved by the Invention The object of the present invention is to provide a disazo compound that can dye cellulose fibers under the pH and dyeing conditions when dyeing polyester fibers with disperse dyes. .

A means for solving the problems, that is, the present invention provides a disazo compound represented by the general formula (1) (where M represents a hydrogen atom or an alkali metal, and represents a hydrogen atom or a naphthalene ring). That is.

In the disazo compound represented by the general formula (1) of the present invention, examples of the alkali metal represented by M include sodium, potassium, and the like.

S・1. ·hmm represents a 7-talene ring or a 7-talene ring.

The substituents include -8O, NHRI group, -EIOtN
(Group 1-OONHR1 group, -0ON < group, -0H
jJ, 7% Cl gene atom, 01-C4 alkyl group,
0IS-C4 alkoxy group, -NHCOR'' group, -N
HCONH, group, -COOR1 group or -8oSM group (
M represents the same meaning as above; R1 and R2 are hydrogen atoms, or when the alkyl group of 01 to c4 represents a benzene ring, substituents include -so, NHm group% -Bogs(group, -0ONHRI group, -0ON(group); , -〇H group, halogen atom S at ~C4z alkyl group sc, ~C4 alkoxy group, 4QRV
S.

-NHOONHI group or 100OR1 group,
Examples thereof include -SO groups.

The disazo compound coated with the general formula (1) can be produced as follows.

For example, l-hydroxy-3-sulfo/acid-&-aminonaphthalene and 7. J, j-) refluoro-(3-)
IJ azine is condensed with IJ azine in an aqueous medium at a pH below θ°C to produce a compound represented by the following structural formula [']
III') to produce a compound represented by the following general formula (IV) OHKn,j'' (wherein, ゛() is the same as the above definition), <,,, f; .

Next, the compound represented by the following general formula [v] is diazotized in an aqueous medium and coupled with the compound represented by the above general formula [■], thereby obtaining the compound represented by the above general formula (1). Disazo compounds of the invention can be produced.

Function and Effect Fibers that can be dyed with the disazo compound of the present invention include cellulose fibers such as cotton, viscose rayon, cuproammonium rayon, and hemp.

Furthermore, it can also be applied to dyeing nitrogen-containing fibers such as polyamide, wool, and silk.

In addition, polyester containing cellulose fiber, triacetate, polyacrylonitrile, polyamide, wool,
The cellulosic fibers in mixed fibers such as silk 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 Engineering nd 8x (3rd edition), are simultaneously added to the dye bath. 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 [I] and the dye bath during dyeing may be adjusted to pHj-1.
Buffers necessary to maintain the temperature at 0 (e.g. carbonic acid, phosphoric acid,
Acids such as acetic acid and citric acid, and sodium salts or potassium salts of these acids, singly or in mixtures, usually 0. J~! ,θ
A dye bath is prepared by adding an electrolyte (sodium chloride or sodium sulfate, etc., usually 1~/j Of/) as required, and the cellulose fibers are placed in this dye bath, and the temperature is 100%. Good dyeing can be achieved by heating at ~tSO°C for 30-10 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, a disazo compound represented by the above general formula CI of the present invention and the above By adding a disperse dye described in Co1our IndθX to the above dye bath, cellulose fibers and polyester fibers can be dyed simultaneously by a one-bath, one-step 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, the dyeing method using the disazo compound of the present invention and the dyeing method for M fibers other than cellulose fibers may be combined to dye cellulose fibers and other fibers from separate baths. It is also possible to adopt a two-bath method.

EXAMPLES Hereinafter, the present invention will be specifically explained by examples, but the present invention is not limited to the following examples.

Example 1 A disazo compound of the present invention represented by the following structural formula (% formula %) in the form of free acid, 0.22% of sodium sulfate/
7 f, Na as a buffering agent! %OO to HPO4/2,
4'f and 8 PO40,/S' water 200yJ
In addition, unmercerized cotton knitted toft was placed in a dye bath adjusted to pH 7, and the temperature was raised to 7.2 (7°C) over 30 minutes.
After dyeing at the same temperature for up to minutes, washing with water, nooping, washing with water,
After drying, a red dyed product was obtained. The degree of dyeing of this dye was very good, and the dyed product obtained was extremely rich, and both light fastness and chlorine fastness were good.

Note that the disazo compound used in this example was manufactured by the following method.

/-Hydroxy-3-sulfonic acid-+-7 minonaphthalene/2≠, θV and/, J,! -trifluoro-triazine/3. After condensation of j f at below 0° C. pH≠, 2-amytuna 7talene-6-sulfo/acid coco. 31
was condensed at 2θ°C to produce a compound represented by the following structural formula, and /-amino-λ-sulfonic acid-a-(r
-Sulfo/acid phenylazo)benzene 3! , 7 f 1
The disazo compound of the present invention represented by the above structural formula was produced by adding a diazo solution obtained by diazotizing aqueous T and coupling with pII7, followed by salting out with potassium chloride.

Example 0.22 of the disazo compound of the present invention represented by the following structural formula (%) in the form of free acid, Glauber's Salt/
6f1 buffer as Na1HPO4/λH! OO,j
Add 1 oy 6 of unmercerized cotton knitted fabric to a dye bath prepared by adding f, KH, PO 40, OJ P to 200 txl of water.
The temperature was raised to 130℃ over 30 minutes, and the temperature was increased to 130℃ for 30 minutes at the same temperature.
After dyeing for a minute, washing with water, nibbling, washing with water, and drying were performed to obtain a red dyed product. This dyeing bath has a p
It was Hr. The dyed product obtained was extremely dense and had good light fastness and chlorine fastness.

Note that the disazo compound used in this example was manufactured by the following method.

l-Hydroxy-3-sulfonic acid-t-aminonaphthalene 2≠, θ2 is I,! ,! -17fluoro-s-triazine/3. A compound of the following structural formula is produced by condensing j f at a pH below θ°C, and l-amino-1-sulfonic acid-+-(4/-sulfo/acid 7-enylazo)benzene J is added to the reaction solution. After adding a diazo solution obtained by diazotizing J, 7T in an aqueous system and coupling at pH ~7, m-ethylaniline/2. /r was added. After confirming the completion of the reaction, the reaction solution was spray-dried to produce the disazo compound of the present invention represented by the above structural formula. A disazo compound of 0.22, a monoazo dye represented by 0.2 r, M/j S'% Na2HPO4/2H200,4' f! as buffering agent. and KH2PO40, / was added to 200% of water and dyed bath, polyester/cotton = so:jo blended fabric 10%
1 was added and the temperature was raised to 130° C. for 30 molecules c. After dyeing at the same temperature for 60 minutes, washing with water, soaping, washing with water, and drying were performed to obtain a red dyed product with good same color property. This dyeing bath had a pH of 1 before and after dyeing. In addition, the dyeing property is very good, and the dyed product obtained is extremely thick and light fastness.
2 and Examples;

Example 1 A disazo compound of the present invention shown in Section 1A below is produced in the form of a free acid according to the method described in Example 2, and a cotton cloth is dyed with the obtained disazo compound, The results are shown in Table 1.

Table 1 Continuation of Table 1 Continuation of Table 1 Continuation of Table 1 Continuation of Table 1

Claims (1)

[Claims] (1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
[I] (In the formula, M represents a hydrogen atom or an alkali metal, ▲
There are mathematical formulas, chemical formulas, tables, etc. A disazo compound represented by the ▼ group (represents a benzene ring or naphthalene ring which may have a substituent).