JPS61200172A - Trisazo compound - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I [M is H, or alkali metal; R<0> is H, lower alkyl, lower alkoxy, or carboxyl; R<1> is H, lower alkyl, lower alkoxy, carboxyl, sulfonic group; R<2> and R<4> are H, lower alkyl, lower alkoxy, acetylamino, sulfonic group; R<3> is lower alkyl, or lower alkoxy; R<5> and R<6> are H, methyl, methoxy, or sulfonic group; Z is Cl, F, aromatic amino residue (except group shown by the formula II), aliphatic amino acid residue; n is 0 or 1; benzene ring may show naphthalene ring]. EXAMPLE:A compound shown by the formula III. USE:Dye for dyeing cellulosic yarn, nitrogen-containing yarn such as wool, etc., in dark blue. PREPARATION:For example, compounds shown by the formulas IV-VI are diazotized and coupled twice, to give a disazo derivative shown by the formula VII. On the other hand, compounds shown by the formulas VIII-X are condensed to give a compound shown by the formula XI, which is coupled with a diazonium compound of the disazo compound shown by the formula VII.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel trisazo compound.

[Conventional technology]

Conventionally, when dyeing cellulose fibers, reactive dyes are used and dyes are dyed at pH 10 in the presence of acid binders such as carbonate, potassium carbonate, and sodium hydroxide, and electrolytes such as sodium chloride and sodium sulfate. In the following, a method is adopted in which the temperature is equal to or less than θQ'c.

However, in recent years, the demand for blended fabrics of cellulose fibers and other fibers, especially polyester fibers, etc. has increased, and such cellulose/polyester mixed fibers (hereinafter simply referred to as C/P) have increased.
In order to dye IM 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 the polyester fibers, it was necessary to use a disperse dye and dye the fibers at a temperature of about 3θ°C.

For example, if the above-mentioned 0/P 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. was there.

For example, in order to fully dye the cellulose fiber with anti-nuisance dye, it is necessary to use an acid binder to raise the pH to 70 or higher.The presence of an acid binder promotes the decomposition of the disperse dye. However, the dyeing of the disperse dye on the polyester fiber side becomes insufficient. - This promotes the water decomposition that causes disperse dyes to dye onto the polyester fiber side, and the dyeing onto the cellulose fiber side is significantly inhibited. Therefore, such O/P
When dyeing R 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.

[Problem that the invention seeks to solve]

The object of the present invention is to provide trisazo compounds which are capable of dyeing cellulose fibers under the pE and dyeing conditions when dyeing polyester fibers (with disperse dyes).

[Technology for solving problems]

That is, the present invention is based on the general formula (1) % formula % (wherein M represents a hydrogen atom or an alkali metal, and R
O represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a carboxyl group; R1 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a carboxyl group, or a sulfonic acid group; R2 and R' represent a hydrogen atom, a lower alkyl group, represents a lower alkoxy group, an acetylamino group, a carboxyl group or a sulfonic acid group, R3 represents a lower alkyl group or a lower alkoxy group, Hs and R11 represent a hydrogen atom, a methyl group, a methoxy group or a sulfonic acid group, and 2 represents a A chlorine atom, a fluorine atom, an aromatic amino residue, an aliphatic amino residue, or a hydroxyl group which may be etherified, n represents ol or l, and benzene ff1A represents a naphthalene ring. The best option is the trisazo compound shown in (good).

In the trisazo compound represented by the general formula (1) of the present invention, examples of the alkali metal represented by M include lithium, sodium, potassium, etc., and RO, R1
, R1, R3 and t, the lower alkyl group and lower alkoxy group include an alkyl group having 7 to 100 carbon atoms,
Examples include alkoxy λ 2 groups, and particularly preferred are methyl and methoxy groups. The aliphatic aamino group represented by 2 includes an amino group, a monoalkylamino group of numbers 01 to 0, a dialkylamine group of Cl-04, a monoethanolamino group, a jetanolamino group, -NHO,
H, So, Na group, -NHOH, C! OON, group, -N
HOIH, 80 West H, 01 group, cyanomethylamino group,
Examples include cyanoethylamino'M1 monofluorino group, piperidino group, etc., and aromatic amino groups include anilino2
f1. N-methylaniline, N-ethylaniline or chloro atom, nitro group, carboxy group, sulfonic acid 2
1! ! i1 Examples include anilino groups substituted with lower alkyl groups or lower alkoxy groups, and examples of hydroxyl groups that may be etherified include -on groups, C3-C4 alkogia groups, chloro atoms, and nitro groups.

Carboxy group, sulfone rJ! Examples include a phenyloxy group substituted with one group, a lower alkyl group, or a lower alkoxy group.

The trisazo compound represented by the general formula (1) can be produced according to the following method. For example, the trisazo compound represented by the general formula (13, (1) and (ff) (In the ceremony
The compound represented by R (1, R1, R2, R11ThR4 and the benzene ring is the same as the above definition) is subjected to usual diazotization and coupling twice to form the following general formula [V] (wherein, RO, R1 , R2, R1, R4 and pen-1
! ” NA is the same as defined above).

On the other hand, the following general formulas [■], [■] and [■] [■]
[■] CV amount] (wherein R', R', Z and n are the same as defined above) are condensed in an arbitrary order in an aqueous medium to obtain the following general formula (IX) (wherein, A compound represented by R5, R', Z and n are as defined above) is produced.

Next, the disazo compound represented by the general formula [V] is diazotized to the compound represented by the general formula (IX) in a water-acetic acid medium, and a nine diazonium compound is coupled to the compound represented by the general formula [I]. The trisazo compounds of the present invention shown can be produced.

[Action and effect]

The trisazo compound of the present invention left in this way can itself be used as a dye.

Examples of fibers that can be dyed with the trisazo compound of the present invention include cotton, viscose rayon, cuproammonium rayon, and hemp E cellulose fibers. Furthermore, it can also be applied to dyeing gold 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 described in Co1our Engineering (3rd edition), are simultaneously added to the dye bath. In addition, it can be dyed.

When dyeing cellulose fiber 1Fr using the Trisfuji-based compound of the present invention, for example, the above general formula (1)
The trisazo compound shown in and the dye bath during dyeing are
Buffers necessary to maintain Hj ~ 10 (e.g. carbonic acid,
Phosphoric acid, acetic acid.

A single or mixture of acids such as citric acid and sodium or potassium salts of these acids, usually 0. j~! , θg/) and, if necessary, add an electrolyte (sodium chloride, sodium sulfate, etc., usually up to isog7), adjust the dye bath, and add the cellulose fibers to the dye bath. Good dyeing can be achieved by heating at a temperature of 700-/j0°C for 30-j0 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, one method is to use a trisazo compound represented by the above general formula (1) of the present invention, Co1our above
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 mentioned above, a one-bath two-bath method is used, in which one or the other fiber is dyed and then the other fiber is dyed in one bath. A step method may be applied, and furthermore, the dyeing method using the trisazo compound of the present invention and the 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.

〔Example〕

Hereinafter, the method of the present invention will be specifically explained with reference to Example 1, but the present invention is not limited to the following Example 1.

Implementation 9i11 / 0.2 g of the trisazo compound of the present invention represented by the following structural formula in free acid form, mirabilite/611, buffering agent Na1HPO4-/2BtO
0-ui and KE! PO, θ-/, F'ft water-
200ydVC7JDEte Add unmercerized cotton stockinette/θJ to a dye bath adjusted to pH 7 and dye 7.2 over 30 minutes.
The temperature was raised to θ°C, 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-sunlight fastness were all good.

Note that the trisazo compound used in this example was produced by the following method.

The monoazo compound produced by diazotization and coupling with Z-aminobenzenesulfone H/7.311'tλ-aminebenzenesulfonic acid/7.3/i in a conventional manner is further diazotized and coupled with -1methoxyj-methylaniline/J , 7g was diazotized and coupled in a conventional manner to produce a disazo compound represented by the following structural formula.

-10,000,/-Amino-? -Hydroxynaphthalene-3.6
-Disulfonic acid31. riI and cyanuric chloride/IJp
After condensation at t3°C, 7 g of 3-(β-human cI-+diethyl)sulfonylaniline sulfate 2J'' was condensed at 30 to Jj°C to produce a compound represented by the following structural formula, and the reaction solution Add a diazo solution obtained by diazotizing the above disazo compound with a water-acetic acid system,
After coupling, the trisazo compound of the present invention represented by the above structural formula was produced by salting out with potassium chloride.

Example λ Monoazo dye 0,29.2g% of the trisazo compound of the present invention represented by the following structural formula [λmax (water): j70nm) in the form of a free acid. Glauber's salt/-2g and sodium bicarbonate θ as a buffer, 1 whole water θo, 1
Polyester/cotton =! θ:j
Add 10g of blended fabric of Q and raise the temperature to 730°C over 30 minutes. After dyeing for 6θ minutes at the same temperature, wash with water, sow pink,
After washing with water and drying, a reddish navy dyed product with good color consistency was obtained. This dyeing bath had a pH of 0 to 9 before and after dyeing.The dyeing property was very good, and the dyed product obtained was extremely thick, light fastness, chlorine resistance, and sweat resistance. The fastness at the mouth was also good.

The trisazo compound of the present invention used in this example was produced by the following method.

Coaminoder carboxybenzene sulfo:/acid 2/
, 71! fr/-naphthylamine-? -sulfonic acid-2
Comethoxy! -Acetylaminoaniline/♂6゜I was subjected to diazo f and coupling in a conventional manner to produce a disazo compound represented by the following structural formula.

On the other hand, -ichiamino! -Hydroxynaphthalene-7-sulfonic acid 3. 1Ill cyanuric chloride/r, 'All
and 3-(β-hydroxyethyl)-sulfonylaniline sulfate sr, ig, and produced a compound represented by the following structural formula, and compared this with the previously produced disazo compound and the diazo ratio and cup 1772. The post-reaction solution was spray dried to produce the trisazo compound of the present invention represented by the above structural formula.

The trisazo compounds of the present invention shown in the table were produced, and cotton cloth was dyed with the obtained trisazo compounds. The results are shown in 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, and R
^0 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a carboxyl group; R^1 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a carboxyl group, or a sulfonic acid group; R^2 and R^4 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, an acetylamino group, a carboxyl group or a sulfonic acid group, and R^
3 represents a lower alkyl group or a lower alkoxy group,
R^5 and R^8 represent a hydrogen atom, a methyl group, a methoxy group, or a sulfonic acid group, and Z represents a chlorine atom, a fluorine atom, or an aromatic amino residue (however, there are ▲mathematical formulas, chemical formulas, tables, etc.▼ except for)
, an aliphatic amino residue or an optionally etherified hydroxyl group, n represents 0 or 1, and the benzene ring A may represent a naphthalene ring).