JPS63105065A - Disazo compound - Google Patents

Abstract

NEW MATERIAL:A compound shown by formula I (M is H or alkali metal; R<1> and R<3> are acylamino; R<2> is alkoxy; R<4> is alkyl or alkoxy; X and Y are halogen, aromatic amino residue; aliphatic amino residue or OH which may be etherified). EXAMPLE:Compound shown by formula II. USE:A dyestuff which dyes cellulose fibers and nitrogen-containing fibers in brown with improved thermotropy resistance. Cellulose fibers and polyester fibers can be simultaneously dyed by one bath by one stage method by adding the dyestuff and disperse dye to a dyeing bath. PREPARATION:For example, a compound shown by formula III-V is diazotized and coupled twice to give a disazo derivative shown by formula VI. Then the compound is condensed with a compound shown by formula VII and a compound shown by formula Y-H in any order in an aqueous medium.

Description

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

Specifically, the present invention relates to a water-soluble disazo compound useful as a dye for brown yarn, which has particularly good dyeability on cellulose fibers and excellent thermotropy resistance.

BACKGROUND OF THE INVENTION In recent years, there has been an increasing demand for blended fabrics of cellulose fibers and other fibers, especially blended fabrics with polyester fibers (hereinafter simply referred to as C/P fibers).

Conventionally, when dyeing cellulose fibers, reactive dyes are used and dyed in the presence of acid binders such as carbonate, potassium carbonate, and sodium hydroxide, and electrolytes such as sodium chloride and sodium sulfate. pH 10 or higher, temperature 1
When dyeing polyester fibers, use a disperse dye and dye at a temperature of approximately /JO℃.When dyeing the 07P fibers mentioned above, Generally, a two-bath method is used in which one fiber of cellulose or polyester is dyed, and then the other fiber is dyed in a separate bath.

However, if the above C/P fibers are dyed in the same process (-bath method) in order to simplify the dyeing process, two different dyes are used in combination of a reactive dye and a disperse dye. When using conventional reactive dyes and disperse dyes, in order to sufficiently collect the reactive dyes on the cellulose fiber side, K must be used as an acid binder and the pH must be set to 70 or higher. However, the presence of an acid binder accelerates the decomposition of the disperse dye, leading to insufficient adhesion of the disperse dye to the polyester fibers.High temperature conditions (usually /30℃), but
Under the above-mentioned high pH and high temperature conditions, the hydrolysis of the reactive dye is promoted, resulting in a problem that dyeing of cellulose fibers is significantly inhibited. There was also a tendency for the dye to fade when the dyed item was ironed.

Problems to be Solved by the Invention The present invention is capable of dyeing cellulose fibers under the pH and dyeing conditions used when dyeing polyester fibers with disperse dyes. The object of the present invention is to provide a disazo compound that also has excellent stability (thermotropy resistance).

A foolproof way to solve problems The gist of the invention is as follows.

General formula CD...CI) (In the formula, M represents a hydrogen atom or an alkali metal, and R
s and Rs represent an acylamino group, R1 represents an alkoxy group, R4 represents an alkyl group or an alkoxy group, and X and Y represent a halogen atom, an aromatic amino residue, an aliphatic amino residue, an ether It consists of disazo compounds represented by the following formula (representing a droxyl group).

To explain the present invention below, in the general formula [■],
As the alkali metal represented by M, lithium 1. Examples include sodium and potassium.

As an acylamino group represented by R1 and R3, -NH
-ca, H, group, -NH-8o, OL group, -NH8O
, O, f(l group, 〇NH8O*0sHt group, NJ(80mO4& group), and an acetylamino group is particularly preferred.

Examples of the alkyl group and/or alkoxy group represented by Rs and R6 include lower alkyl groups such as methyl, ethyl, and butyl, and/or lower alkoxy groups such as methoxy, ethoxy, and butoxy.

Further, the aromatic amino residue represented by X and Y is represented by the formula (■).

t-child; halogen atoms such as chlorine atom, fluorine atom, bromine atom;
Alkyl groups such as methyl group, ethyl group, butyl group; Alkoxy groups such as methoxy group, ethoxy group, butoxy group; −
000M; -130,M; or -8o,O,
H40SOaM is represented, and R1 represents a hydrogen atom or an alkyl group such as a methyl group, ethyl group, propyl group, butyl group. ), and examples of aliphatic amino residues include groups represented by the formula (■), hydroxyl group, cyano group, -0
00M, -so, n, or an alkyl group such as a methyl group, ethyl group, or butyl group which may be substituted with ClH407; or a ring such as a morpholino group formed by connecting R'' and R'' to each other; Show minutes. ), examples of the optionally etherified human tetraxyl group include formula 1, 0R11 (in the formula).

R'' represents a hydrogen atom; an alkyl group such as a methyl group, an ethyl group, or a butyl group; or a phenyl group which may be substituted with -130,M.

In the present invention, a substituent in which at least one of X and Y in the general formula (IIIC has a reactive group, that is,
Halogen atom; -so, a group represented by the formula (■) having at least 7 osomM; or -80IO, H4
A group represented by formula (2) having at least one alkyl group substituted with 073 is preferred.

The disazo compound represented by the general formula [I] can be produced as follows. For example, the following general formula (
If), (13 and [1v]Ell) (1
) [B] (In the formula, R1, R1, R1, R4
and M are the same as defined above) are subjected to usual diazotization and coupling twice, and the compound represented by the following general formula C
It is a disazo compound represented by V).

Next, the compound represented by the general formula [■] and the following formula CV
I) , CVID (Vl) By condensing a compound represented by CVID (wherein X and Y are the same as defined above) in an arbitrary order in an aqueous medium,
A disazo compound of the general formula [I] can be produced.

The disazo compound of the present invention thus produced 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.

Polyester also contains cellulose fibers.

triacetate, polyacrylonitrile, polyamide,
Of course, the cellulosic fibers in mixed fibers such as wool and silk can be dyed well.

In the method for dyeing fibers using the disazo compound of the present invention, dye 1 necessary for dyeing non-cellulose fibers, such as disperse dyes described in 0olour Index (3rd edition), is 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 (1) is used, and the dye bath is adjusted to pH, t during dyeing.
Buffers necessary to maintain ~lO (for example, acids such as carbonic acid, phosphoric acid, acetic acid, citric acid, and sodium or potassium salts of these acids, singly or in mixtures) are usually used to maintain O1S~!
, about 01/l) and an electrolyte (sodium chloride or sodium sulfate, etc.) as necessary.
JOA-1 was added at a temperature of 100-110°C.
Good dyeing can be achieved by heating for 0 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-mentioned 0010ur engineeringndeX
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, the conventional one-bath two-step method of dyeing one of the K fibers and then dyeing the other fiber in the same bath can be used. Furthermore, the dyeing method using the disazo 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 the bath method.

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

Example/Production of disazo compound: Conaphthylamine-J,t,t-)risulfonic acid, y
The monoazo compound produced by diazotizing and coupling r, sg with comethoxy S-acetylaminoaniline/4.0 II in a conventional manner is further diazotized and coupled with --methoxy-
A disazo compound represented by the following structural formula was prepared by diazotization and coupling with 5-acetylaminoaniline/l, 01 in a conventional manner.

This disazo compound/! Tl and cyanuric heptadide/
,? ,! , 9 at below 0'C, co-aminobenzenesulfonic acid/7. A disazo compound represented by the following structural formula was produced by condensing Jl at 20°C and salting out with potassium chloride. Maximum absorption wavelength λma of this compound! (Water) was Dac-nm.

Dyeing method: Disazo compound O shown by the above structural formula in the form of free acid
, CoI, Glauber's salt/6I, Na as a buffer, HPO=a
/ 2B*OO, e 11 and &P0.0. /
, F was added to water and 2 oorttt, and the unmercerized cotton stockinette Ioi was placed in a dye bath prepared at pB. After washing with water and drying, a brown dyed product was obtained. The degree of dyeing of this dye is very good, and the dyed product obtained is extremely dense, and the light fastness, especially chlorine fastness and sweat-sunlight fastness, are both good. The thermotropy resistance when applied was also excellent.

Examples In the form of free acids, disazo compounds represented by the following structural formulas %, tg, and monoazo dyes represented by 0.2, lil, and mirabilite lcoy.

A blended fabric of polyester/cotton = zo:go was added to a dyebath prepared by adding Nh*HPOa・I J&OO,l I and KHIPO40,/11 as a buffering agent to 00 ml of water, and it took 30 minutes to iso After raising the temperature to ℃ and dyeing for 60 minutes at the same temperature, washing with water, So pink, washing with water,
After drying, a brown dyed product with good color consistency was obtained. The dyeing bath was at pHt before and after dyeing. In addition, the dyeing property was very good, and the dyed product obtained was extremely dense, and the light resistance, chlorine resistance, and sweat and sunlight fastness were all good. The thermotropy resistance was also impaired.

The disazo compound used in this example was produced according to the method described in Example.

Example J Structural formula below in free acid form %formula%() Disazo compound 01-9 shown by 01-9, Glauber's Salt/6g.

Na1PO4・l Kouma Oo, Hiro I and K as buffering agents
Add H*PO4 (7,/l to 00ml of water and add pfI
Put 70g of unmercerized cotton knitted fabric into the dye bath prepared in step 7 and raise the temperature to 10°C over 30 minutes. After dyeing at the same temperature for 60 minutes, wash with water, soap, wash with water, and dry. A dyed product was obtained.

The degree of dyeing of this dye is very good, and the dyed product obtained is extremely dense.The light fastness, chlorine fastness, and sweat-sunlight fastness are all good. The thermotropy resistance was also excellent.

The disazo compound used in this example is -1-7-thylamine--, b, I-) lysulfonic acid J1.
Cometoxie J l! -acetylaminoaniline/
A monoazo compound produced by diazotization and coupling with 4.01 in a conventional manner is further subjected to comethoxy! -7
A disazo compound represented by the following formula was produced by diazotization and coupling with cetyl aminoaniline 76.01 in a conventional manner.

This disazo compound /, 3I and cyanuric chloride /t,
! After condensing rI at below 5°C, 3-(β-hydroxyethyl)sulfonylaniline sulfate, 2 g,
/jit-30-, condensed at 77°C.

The above disazo compound was prepared by salting out with potassium chloride.

Example DA 0.2 g of a disazo compound represented by (λwax j, ynm (*)) in the form of free acid, 161 g of Glauber's salt
, Na, HPO, °l as buffering agents, 1110 o, q
y and U! 1PO4o, t I water 5oOrnl
Unmercerized cotton broadcloth 1011 was placed in a dye bath heated to K, T and Nm and heated to /JO℃ over 30 minutes, dyed at the same temperature for 60 minutes, washed with water, soaped, washed with water and dried. A brown dyed product with good same color property was obtained. The dye bath was pg t before and after dyeing. In addition, the dyeing property is very good, and the dyed product is very thick and has good light fastness, chlorine fastness, and sweat-sunlight fastness. The thermotropy resistance was also excellent.

The disazo compound used in this example was manufactured by the following method. That is, 1 molar proportion of the following compound was condensed in an aqueous medium at pH 7, and then 1 molar proportion of 2-methyl-5-(β-
It was produced by condensing hydroxyethyl)sulfonylaniline sulfate with deO''CpH&.

Example: 0.2 g of a monoazo dye represented by 0.2ji of the disazo compound described in Example 3, mirabilite/J, 9° buffering agent: NaJ)O,'/2 Ego O,II 77 and KHJ'0. 0. /! Add i to 100rnl of water and add polyester/cotton = so:go to the dye bath made from Tev4.
It took 30 minutes to put in the blended fabric 1077/, 70'
After dyeing at the same temperature for 1.0 minutes, washing with water, soaping, washing with water, and drying were performed to obtain a brown dyed product with good color constancy. The dye bath was at pHt before and after dyeing. In addition, the dyeing property is very good, and the dyed product obtained is extremely dense and has good light fastness, chlorine fastness, and sweat resistance.
All had good sunlight fastness.

Example 6 A disazo compound represented by the following general formula (expressed in free acid form) was left in a method similar to Example 1 or J, and a cotton fabric was dyed according to a method similar to Example 1 or 3. . 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
^1 and R^3 represent an acylamino group, R^2 represents an alkoxy group, R^4 represents an alkyl group or an alkoxy group, and X and Y are a halogen atom,
A disazo compound represented by an aromatic amino residue, an aliphatic amino residue, or a hydroxyl group that may be etherified.