JPS6284160A - Disazo compound - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [M is H or alkali metal; R<1> is H, Cl, lower alkyl, lower alkoxy, nitro or carboxyl; R<2> is lower alkyl, lower alkoxy or sulfonic acid group; R<3> is H, lower alkyl, lower alkoxy, -NHCONH2, etc.; R<4> is H or lower alkyl; R<5> is H or (substituted) lower alkyl; Y is -SO2CH= CH2, etc.; Z is Cl, F, Br, aliphatic or aromatic amino residue, etc.; m is 1-3; n is 0 or 1; benzene rings A and B may represent a naphthalene ring. EXAMPLE:The compound of formula II. USE:A dye for dyeing a cellulosic fiber. The dyeing can be carried out under the pH and dyeing condition for the dyeing of a polyester fiber. PREPARATION:The compounds of formula III and IV are diazotized and coupled to obtain a monoazo compound of formula V. Separately, the compounds of formula VI-VIII are condensed to form the compound of formula IX. The compound is coupled with a diazonium compound produced by diazotizing the monoazo compound of formula V.

Description

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

Conventional technology Conventionally, when dyeing cellulose fibers.

Using reactive dyes, sodium carbonate, potash carbonate,
Acid binders such as sodium hydroxide and sodium chloride,
A method is adopted in which the reaction is carried out in the presence of an electrolyte such as sodium sulfate, at a pH of 0.000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000,000,000.

However, in recent years, the demand for blended fabrics of cellulose fibers and other fibers, especially polyester fibers, has increased, and in order to dye these various cellulose/polyester mixed fibers (hereinafter simply referred to as O/P fibers). It was necessary to apply dyes and dyeing conditions to cellulose fibers and dyes and dyeing conditions to polyester fibers, respectively. 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 above-mentioned 0/P pJ fibers were to be dyed in the same process, two different dyes would be used in combination of one reactive dye and a disperse dye, which would cause several problems. there were.

In other words, in order to sufficiently dye the cellulose fiber side with a reactive dye, it is necessary to coat the cellulose fiber with an acid binder.

The presence of the acid binder promotes the separation of the disperse dye, leading to insufficient dyeing of the disperse dye to the polyester fiber. On the other hand, disperse dyes are applied to polyester fibers i.
In order to dye the fiber side, high temperature conditions (usually at 30°C) are required, but at high temperatures under the above-mentioned high pH, the hydrolysis of the reactive dye is promoted, and the dyeing of the cellulose A fiber becomes significant. This will result in interference. Therefore, such c,
When dyeing '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.

Problems to be Solved by the Invention The present invention aims to provide a disazo compound that can be used to dye polyester fibers with a monodisperse dye and that can dye cellulose fibers under the dyeing conditions.

Means for removing problems The disazo compound of the present invention has the general formula (1) (wherein M represents a hydrogen atom or an alkali metal, R; represents a hydrogen atom,
Represents a chlorine atom, lower alkyl group, lower alkoxy group, nitro group or carboxyl group, R2 represents a lower alkyl group, lower alkoxy group or sulfonic acid group u
3 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, -
NHOONH2 group, acetylamino group or sulfonic acid group, R4 represents a hydrogen atom or a lower alkyl group, R5 represents a hydrogen atom or an optionally substituted lower alkyl group, Y represents a -8O2CH=OHz group or - represents a so2ca2ca2w group (where W represents a group that is eliminated by the action of an alkali), X represents a phenylene group or a naphthylene group which may have a substituent, and 2 represents a hydrogen atom or a fluorine atom. , a bromine atom, an aliphatic group, n represents O or 1, and a benzene ring and B may represent a naphthalene ring).

Examples of the alkali metal represented by 5M in the disazo compound represented by the general formula [''!] of the present invention include sodium, potassium, etc., and R1, Rz, Rs, R4
Examples of the lower alkyl group and lower alkoxy group represented by u6 include alkyl groups and alkoxy groups having from ≠ to ≠ carbon atoms.

Further, as a substituent for R5, a cyano group, a hydroxyl group,
Examples thereof include a lower alkoxy group, a nitrogen atom, and a lower alkylcarboxy group. X is particularly preferably a methyl group,
Substituted with one or two substituents selected from the group of lower alkyl groups such as ethyl groups, lower alkoxy groups such as methoxy groups and ethoxy groups, chlorine atoms such as chlorine atoms and bromine atoms, and sulfonic acid groups. Examples include a phenylene group or a naphthylene group, which may be substituted.

A specific example of -N-X- is bu3a
Groups that are eliminated by the action of an alkali represented by SO2CH=CH1HY include sulfuric acid ester, thiosulfuric acid ester, and phosphoric acid ester! , an acetic acid m-ester group, a norogen atom, and the like.

In addition, the aliphatic or aromatic amino residues represented by 2 include aminos Of~4 alkylamino, ethanolamino, β-cyanoethylamine 1% d-sulfoethylamino, 'glycine residue, anilino and sulfo,
Chloro, lower alkyl.

Examples include anilino groups substituted with lower alkyl, nitro, carboxy, and the like.

The disazo compound represented by the general formula CI) can be produced as follows. To (II)
A compound represented by (In (where M, R', R'', R1% m and benzene rings A and B are the same as defined above) is subjected to conventional diazotization and coupling to form the following general formula [■] ( In the formula, M, R', R2, R3, m and a benzene ring A
and B are the same as defined above).

On the other hand, the following formula (V), CVI'1.(■) (where M,
R', R5, X, Y, Zb and n are the same as defined above) are condensed in an arbitrary order in an aqueous medium to form the following general formula [■] (where M, R', R ”, 2 and n are the same as defined above).

Then, the above-mentioned [IV] is added to the compound represented by the general formula [■].
The monoazo form of is diazotized by a conventional method and coupled with a nine-diazonium compound to obtain the general formula (
11 disazo compounds can be prepared.

The disazo compound of the present invention created 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, 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 0olour 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 [■] and the dye bath during dyeing may be adjusted to pHj-10.
Buffers necessary to maintain the temperature (for example, acids such as carbonic acid, phosphoric acid, acetic acid, citric acid, etc., and sodium salts or potassium salts of these acids, singly or in mixtures, usually o, r - r,

f/l Q degree), and if necessary electrolyte (sodium chloride or sodium sulfate, etc.)
? Add the cellulose fibers to the dye bath, and add the cellulose fibers to the dye bath.

Good dyeing can be achieved by heating at ~/10°C for 30-70 minutes.

In addition, blended 0010urn fabrics manufactured by mixing cellulose fibers with other fibers such as polyester fibers are also used.
By adding a disperse dye listed in ex f'fi to the above dye bath, cellulose fibers, polyester fibers and gold
They can be dyed simultaneously using the one-bath method.

In addition, when dyeing blended fabrics, blended knitted fabrics, etc., as described above, a one-bath two-bath method in which one of the fibers is dyed and then the other R## is dyed in the same bath is used. A step method may be applied, and furthermore, a dyeing method using the disazo compound of the present invention and a dyeing method for 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 method of the present invention will be explained in more detail using practical examples, but the present invention is not limited to the following examples.

Example! λ-Naphthylamine-≠? -Disulfonic acid 30.3?
/-aminobenzene-cosulfonic acid/7.3? A monoazo compound represented by the following formula was prepared by diazotization and coupling using a conventional method. On the other hand, 2-amino-hydroxynaphthalene-7-sulfonic acid 3.
the law of nature? After condensing and cyanuric chloride/Ljf at 5°C or lower, Gu(β-human axyethyl)sulfonyl N-methylaniline sulfate λ26f'f: 30-3! A compound of the following formula is produced by condensation at °C, a diazo solution obtained by diazotizing the above monoazo compound by a conventional method is added to the reaction solution, coupling is carried out at 0-jC, and salting out with potassium chloride is carried out to produce the following compound: A disazo compound having the structural formula (in the free acid form) and having the analytical value by visible light absorption shown below, ≠2
I got it.

C1 (λmaxj/r dingding (water)) Disazo compound 0.2f shown by the above structural formula.

Glauber's salt / 4 Na2HPO4 / J as f1 buffering agent
H2O0,≠? Unmercerized cotton stockinette 101 was added to a dye bath prepared by adding KH2PO40,/f to 00d of water and adjusted to 127°C, heated to IIO°C over 30 minutes, and dyed at the same temperature for 60 minutes. After, wash with water, so pink,
After washing with water and drying, a bright red dyed product was obtained. 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-sunlight fastness were all good.

Example 911/Unmercerized cotton stockinette l0ff
Wool muslino O? Staining was carried out in accordance with Example 1, except for the following.

As a result, the wool muslin was dyed extremely deep red.

Example 3 Aniline-2,j-disulfonic acid coj, JP was diazotized and coupled with 2-methoxy-j-methylaniline/3.7t by a conventional method to obtain a monoazo compound represented by the following formula as Nozomimaru. . On the other hand, 11 methylamino! -Human axynaphthalene-7-sulfone fi J 7. rit and chloride are null/l,! After condensation at below ft-j℃, j-(
d-Hydroxyethyl)sulfonylaniline sulfate ester? , a compound of the following formula is prepared by condensation with tr3o~3j'C, this and the previously produced monoazo compound are subjected to azotization and coupling, and the reaction solution is spray-dried to obtain the following structural formula. (Showed in free acid form.)
I was reminded of the disazo compound octopus, which has analytical values based on visible light absorption.

Disazo represented by the above structural formula (g compound 0.22, Glauber's salt/4F, Na2HP○4-/jH20o as buffer 4j)
, jy and IIH2po, θ,02? water 200w
Add 10 f unmercerized, knitted fabric to the dye bath prepared in addition to step d, raise the temperature to /JO℃ over 30 minutes, dye at the same temperature for 30 minutes, then wash, soap, wash and dry. I borrowed some dark blue dyed material. This dyeing bath is used before dyeing.
The pH was r throughout. The resulting dyed product is an extremely deep dark purple color.

The light fastness, chlorine fastness, and sweat-sunlight fastness were all good.

Example 11 Disazo compound O, produced in Example 3, and monoazo dye represented by 0. -21% awn i/j f
.

Na2HPO4・/2 H2O0,'l as buffering agent
f and xn2po40. )T was added to water-〇〇yd, 10f of blended fabric of polyester/cotton = jo", so was added to a dye bath prepared, and the temperature was raised to 130°C for 30 minutes.
After dyeing at the same temperature for 60 minutes, the dyed material was washed with water, soaked pink, washed with water, and dried to obtain a dark blue dyed product with good color constancy. The dyeing bath was at pHr before and after dyeing. In addition, the dyeability was very good, and the dyed product obtained was an extremely deep dark purple color, and the light fastness, chlorine fastness, and sweat-sunlight fastness were all good.

Example! ~Koj

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, and R
^1 represents a hydrogen atom, a chlorine atom, a lower alkyl group, a lower alkoxy group, a nitro group or a carboxyl group, and R
^2 represents a lower alkyl group, lower alkoxy group or sulfonic acid group, R^3 is a hydrogen atom, a lower alkyl group,
Represents a lower alkoxy group, -NHCONH_2 group, acetylamino group or sulfonic acid group, R^4 represents a hydrogen atom or a lower alkyl group, R^5 represents a hydrogen atom or an optionally substituted lower alkyl group, Y is -SO_2CH=CH_2 group or -SO_2CH_2
CH_2W group (where W represents a group that is eliminated by the action of an alkali), X represents a phenylene group or naphthylene group which may have a substituent, and Z
represents a chlorine atom, a fluorine atom, a bromine atom, an aliphatic or aromatic amino residue, a methoxy group or a phenoxy group, m represents 1, 2 or 3, n represents 0 or 1, and a benzene ring A and B may represent a naphthalene ring).