JPS62132968A - Disazo compound and dye composition containing same - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [M is H or alkali metal; Dz is disazo component residue of benzene or naphthalene base; R<1> is H or lower alkyl; R<2> is H or (substituted) lower alkyl; A is aromatic or aliphatic divalent residue; X is (substituted) phenylene or naphthylene; Y is -SO2CH=CH2 or -SO2C2H4W (W is group removable with alkali); m is 0 or 1]. EXAMPLE:A compound of formula II. USE:For dyes capable of dyeing cellulose fibers, nitrogen-contg. fibers orange - scarlet; capable of dyeing cellulose fibers under dyeing condition for polyester fibers. PREPARATION:For example, 2mol of a coloring matter of formula III and 1mol of a compound of formula H2N-A-NH2 are condensed to form a disazo compound of formula IV; with which 1mol of a second compound of formula V is condensed at 90 deg.C.

Description

Detailed Description of the Invention (a) Object of the invention (a) Industrial field of application The present invention relates to a novel disazo compound used as a dye for cellulosic fibers and nitrogen-containing fibers, and a dye composition using the same. It is related to.

(b) Conventional technology Conventionally, when dyeing cellulose fibers, reactive dyes are used in the presence of acid binders such as sodium carbonate, potassium carbonate, and sodium hydroxide, and electrolytes such as sodium chloride and sodium sulfate. At a pH of 10 or higher and a temperature of 100
A method is adopted in which the process is carried out at temperatures below ℃.

However, in recent years cellulose fibers and other fibers.

In particular, the demand for blended fabrics with polyester fibers is increasing, and such cellulose/polyester blended fibers (hereinafter simply referred to as C
/PHa fiber. ) to dye the
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 C/P fibers mentioned above were to be dyed in the same process, two different dyes would be used in combination, a reactive dye and a disperse dye, which would pose several problems. Ta. In other words, in order to dye the reactive dye sufficiently on the cellulose fiber side, the pH is adjusted using an acid binder.
However, the presence of an acid binder accelerates the decomposition of the disperse dye, resulting in insufficient dyeing of the disperse dye to the polyester fiber. On the other hand, high temperature conditions (usually 130°C) are required to dye disperse dyes onto polyester fibers, but under high pH conditions such as those mentioned above, high temperatures promote the hydrolysis of reactive dyes, resulting in cellulose Dyeing to the fibers will be significantly inhibited.

Therefore, when dyeing such C/P fibers, 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 is.

(c) Problems to be Solved by the Invention The present invention provides a disazo compound and a dye containing the disazo compound that can dye cellulose fibers under the pH and other dyeing conditions used when dyeing polyester fibers with disperse dyes. It is intended to provide a composition.

(b) Structure of the Invention (a) Means for Solving the Problems The above problems could be solved by the disazo compound of the present invention having a specific molecular structure. That is, the present invention relates to the general formula CI represents an atom or a lower alkyl group which may be substituted, A represents an aromatic or aliphatic divalent residue, or a phenylene group or naphthylene group which may have a substituent, and Y represents -So, Cl=CH, group or -3O2C28
It represents a 4w group (where W represents a group that is eliminated by the action of an alkali), and m represents O or 1. ] The present invention relates to a disazo compound represented by the following and a dye composition containing the same.

In the disazo compound represented by the general formula (1) of the present invention, the alkali metal represented by M includes lithium, sodium, potassium, etc., and the diazo component residue represented by Dz includes a sulfonic acid group, a carboxyl group, etc. Acid group, C to C4 lower alkyl group, lower alkoxy group,
Examples include phenyl groups or naphthyl groups substituted with halogen atoms such as chlorine atoms and bromine atoms.

The lower alkyl group represented by R1 and R2 is C
Examples include alkyl groups of 1 to C4.

Further, as a substituent for R2, a cyano group, a hydroxyl group,
Examples include a lower alkoxy group, a halogen atom, and a lower alkylcarboxy group.

The divalent residues represented by A include ethylene group, 1,
Aliphatic groups such as 3-propylene group, 1,4-butylene group, hexamethylene group, or phenylene group or naphthylene group substituted or unsubstituted with methyl group, methoxy group, carboxyl group, sulfonic acid group, chlorine atom, etc. Examples include aromatic groups such as.

X is particularly preferably a lower alkyl group such as a methyl group or an ethyl group, a lower alkoxy group such as a methoxy group or an ethoxy group,
Examples include a phenylene group or a naphthylene group which may be substituted with one or two substituents selected from the group of halogen atoms such as chlorine atoms and bromine atoms, and sulfonic acid groups.

A specific example of -N-X- is i.

etc.

Examples of the group represented by W which are eliminated by the action of an alkali include a sulfate ester group, a thiosulfate ester group, a phosphate ester group, an acetate ester group, and a halogen atom.

The disazo compound represented by the general formula (1) can be produced as follows.

For example, the 2 mole ratio of the dye represented by the general formula (n) (where M, Dz, R', and m are the same as defined above) and the following formula (m) H2N-A-NH,
...Cm) (wherein A is the same as defined above) is condensed to form the following formula [IV] (wherein M, Dz, R1, m are the same as defined above) ) as a disazo compound.

Next, the following general formula (V) NH-X-Y (Vl (in the formula R
The disazo compound of general formula (1) can be produced by condensing 1 molar proportion of the compound represented by ", X and Y are the same as defined above) at 90°C.

The disazo compound of the present invention produced in this way is
As described above, the disperse dye can be used as a dye capable of dyeing cellulose fibers under the pH and other dyeing conditions used when dyeing polyester fibers.

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. 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 disazo 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.

Cellulose fibers using the disazo compound of the present invention,
When dyeing nitrogen-containing fibers, etc., for example, the disazo compound represented by the above general formula [1] is used at 0,01 to 50 #
IQ diameter and buffers necessary to maintain the dye bath at pH 5 to 10 during dyeing (for example, acids such as carbonic acid, phosphoric acid, acetic acid, citric acid, boric acid, and monomers of sodium or potassium salts of these acids) one or a mixture) is usually 0.5 to 5.
0y#I, and if necessary, electrolyte (sodium chloride or sodium sulfate, etc.) is usually 1 to 150 g/a.
Preferably, a dye bath to which about 40 to 80 bleeding/Q is added is prepared, and cellulose fibers and nitrogen-containing fibers are added to this dye bath,
Good dyeing can be achieved by heating at a temperature of 100 to 150°C for 30 to 50 minutes.

In addition, in order to dye blended fabrics, blended knitted fabrics, etc. produced by mixing cellulose fibers with other fibers such as polyester fibers, in the above composition, the above Co1
0.01-50g of disperse dye listed in our Index
By preparing a dye bath by adding about 0.5 to 3i/Q of a surfactant (e.g., sulfoconolytic acid-based anionic surfactant, nonylphenol-based nonionic surfactant, etc.) 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 described above, a one-bath two-step method is used in which one of the fibers is dyed first, and then the other fiber is dyed in the same bath. Furthermore, a two-bath method may be used 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 the law.

Therefore, the dye composition containing the disazo compound of the present invention as a dye may contain, in addition to the dye component, other components necessary for the dye, such as water as a medium, the above-mentioned buffer, electrolyte, surfactant, etc. It contains a dyeing aid. In addition, other dyes, such as Co1our, may be used if necessary.
Disperse dyes listed in the Index can also be added.

The dye composition of the present invention may be one that can be used as it is for dyeing, or it may be in the form of a thick liquid or paste that can be used after being dissolved in water during dyeing. In the case of a composition that can be used as is for dyeing, as described above, the disazo compound represented by the general formula (I) is added in an amount of 0.01 to 50
An aqueous solution containing approximately 0.5 to 5.0 g/Q of a laxative and approximately 1 to 150 g/Q of an electrolyte is generally used. In the case of a concentrated liquid or paste, the above-mentioned disazo compound can be contained in a diameter of about 200 fi /Q.

(B) Examples Hereinafter, the present invention will be explained in more detail by way of examples, but the present invention is not limited to the following examples.

Example 1 A disazo compound represented by the following formula was produced by condensing 2 molar proportions of the monoazo dye represented by the following formula and 1 molar proportion of P-phinyl diamine in an aqueous medium at 30 to 40°C, and the reaction solution was Inside 3-(
Add 2 molar proportions of β-hydroxyethyl)sulfonyl N-methylaniline sulfate, condense at 90°C, and then salt out with potassium chloride to obtain the following structural formula (shown in free acid form) and visible light absorption analysis values. A disazo compound having the following was obtained.

(λ, , : 477 nm (water)) Next, 0.2 ml of the above disazo compound, 16 ml of Glauber's salt, Na2HP0.12H, 00, 49 and K as buffering agents.
H, Po.

10 ml of unmercerized cotton stockinette was added to a dye bath prepared by adding 0.1 ml to 200 d of water to adjust the pH to 7, and the temperature was raised to 120°C over 30 minutes. After dyeing at the same temperature for 60 minutes, Washing with water, soaping, washing with water, and drying were performed to obtain an orange dyed product. The degree of dyeing of this dye was very good, and the dyed product obtained was an extremely deep orange color, and the light fastness, chlorine fastness, and sweat-sunlight fastness were all good.

Example 2 Dyeing was carried out in accordance with Example 1 except that the 10% unmercerized cotton stockinette in Example 1 was changed to wool muslin 109.

As a result, the wool muslin was dyed an extremely deep orange color.

Example 3 A disazo compound represented by the following formula was produced by condensing 2 molar proportions of the monoazo dye represented by the following formula and 1 molar proportion of ethylenediamine in an aqueous medium at 30 to 40°C, and 3-(
After adding 2 molar proportions of β-hydroxyethyl)sulfonyl N-ethylaniline sulfate and condensing at 90°C, the disazozoate has the following structural formula (shown in free acid form) and the analytical value by visible light absorption. The compound was obtained.

Next, the above disazo compound 0.21, Glauber's salt 16, Na, HPo, 12H,00,5iF and K were added as buffering agents.
Add 10 ml of unmercerized cotton stockinette to a dye bath prepared by adding H,PO40,021i to 2001all of water, and
The temperature was raised to 130°C over 0 minutes, dyed at the same temperature for 30 minutes, and then washed with water.

After soaping, washing and drying, a scarlet dyed product was obtained. The pH of this dyeing bath was 8 before and after dyeing.

The dyed product obtained was extremely dense and had good light fastness, chlorine fastness, and sweat-sunlight fastness.

Example 4 0.2 of a disazo compound represented by the following structural formula in the form of a free acid, 0.2 of an anthraquinone dye represented by the following structural formula, 12 shots of Glauber's salt, NaJPo, 12H,00,4i and KH as buffering agents. ,P
A blended fabric 109 of polyester/cotton = 50:50 was added to a dye bath prepared by adding O40,19 to 200% of water, and
The temperature was raised to 130° C. over 0 minutes and dyed at the same temperature for 60 minutes, followed by washing, soaping, washing and drying to obtain a red dyed product with good isochromaticity. The pH of this dyeing bath was 8 before and after dyeing. Furthermore, the dyeing property was very good, and the dyed product obtained was extremely rich, and the light fastness, chlorine fastness, and sweat-sunlight fastness were all good.

Note that the disazo compound used in this example was manufactured according to Example 1.

Examples 5 to 27 The above general formula (1) was prepared according to the method described in Example 1.
Various disazo compounds (shown in free acid form) were prepared as listed in Table 1 below. The analytical values of each of the obtained compounds and the results of dyeing the cotton cloth are as shown in Table 1.

(Margin below) Example 28 A concentrated dye composition was obtained by blending the following components.

Disazo compound of Example 1 109Na, HPO
412H201Of KH, PO43g Water 200I
All the above compositions are mixed with 10% water at the time of use. A dyebath can be prepared by diluting to OOOmQ.

Example 29 A concentrated dye composition was obtained by blending the following components.

Disazo compound of Example 3 19 Na,) IPO412H202,59 KH, PO40, 1 g Glauber's salt 25 g Water 200 a
Q: The above composition can be used to prepare a dye bath by diluting it with 800% water.

(c) As shown in the detailed description of the invention and the examples, the present invention provides a novel disazo compound and its use as a dye to improve the dyeing of polyester fibers with monodisperse dyes. Cellulose fibers can be dyed well even under PH and other dyeing conditions, so even when cellulose/polyester mixed fibers are dyed, there is no need for a separate bath as in the past.

Claims (15)

[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 D
z represents a benzene or naphthalene-based diazo component residue, R^1 represents a hydrogen atom or a lower alkyl group, R^2 represents a hydrogen atom or an optionally substituted lower alkyl group, and A represents an aromatic or represents an aliphatic divalent residue, X represents a phenylene group or naphthylene group which may have a substituent, and Y represents -SO_2CH=
It represents a CH_2 group or a -SO_2C_2H_4W group (where W represents a group that is eliminated by the action of an alkali), and m represents 0 or 1. ] A disazo compound represented by (2) Dz is a sulfonic acid group, a carboxylic acid group, C_1_~
The disazo compound according to claim 1, wherein C_4 is a lower alkyl group, C_1_ to_4 is a lower alkoxy group, or a phenyl group or naphthyl group substituted with a halogen atom. (3) The disazo according to claim 1, wherein R^2 is a hydrogen atom, a lower alkyl group, or a lower alkyl group substituted with a cyano group, a hydroxyl group, a lower alkoxy group, a halogen atom, or a lower alkyl carboxyl group. Compound. (4) The disazo compound according to claim 1, wherein X is a phenylene group, a naphthylene group, a lower alkyl group, a lower alkoxy group, a phenylene group or a naphthylene group substituted with a halogen atom or a sulfonic acid group. (5) The disazo compound according to claim 1, wherein W is a sulfate group, a thiosulfate group, a phosphate group, an acetate group, or a halogen atom. (6) A is ethylene group, 1,3-propylene group, 1,4
- The disazo according to claim 1, which is a butylene group, hexamethylene group, phenylene group, naphthylene group, or a phenylene group or naphthylene group substituted with a methyl group, a methoxy group, a carboxyl group, a sulfonic acid group, or a chlorine atom. Compound. (7) The following 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 D
z represents a benzene or naphthalene-based diazo component residue, R^1 represents a hydrogen atom or a lower alkyl group, R^2 represents a hydrogen atom or an optionally substituted lower alkyl group, and A represents an aromatic or represents an aliphatic divalent residue, X represents a phenylene group or naphthylene group which may have a substituent, and Y represents -SO_2CH=
It represents a CH_2 group or a -SO_2C_2H_4W group (where W represents a group that is eliminated by the action of an alkali), and m represents 0 or 1. ] A dye composition characterized by containing a disazo compound represented by the following. (8) Dz is a sulfonic acid group, a carboxylic acid group, C_1_~
8. The dye composition according to claim 7, wherein C_4 is a lower alkyl group, C_1_ to_4 are lower alkoxy groups, or phenyl or naphthyl groups substituted with halogen atoms. The dye composition according to claim 7, wherein (9) is a hydrogen atom, a lower alkyl group, or a lower alkyl group substituted with a cyano group, a hydroxyl group, a lower alkoxy group, a halogen atom, or a lower alkyl carboxyl group. (10) The dye composition according to claim 7, wherein X is a phenylene group, a naphthylene group, or a phenylene group or naphthylene group substituted with a lower alkyl group, a lower alkoxy group, a halogen atom, or a sulfonic acid group. (11) The dye composition according to claim 6, wherein W is a sulfate group, a thiosulfate group, a phosphate group, an acetate group, or a halogen atom. (12) The dye composition according to claim 7, wherein the dye composition is a composition containing water and a dyeing aid. (13) The dye composition according to claim 12, wherein the dyeing auxiliary agent is a buffer, an electrolyte, and a surfactant. (14) The dye composition according to claim 13, wherein the buffering agent is carbonic acid, phosphoric acid, acetic acid, citric acid, boric acid, or a salt thereof. (15) The dye composition according to claim 13, wherein the electrolyte is sodium chloride or sodium sulfate.