JPS62132969A - Disazo compound and dye composition containing same - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [M is H or alkali metal; R<1> is H, COOH, lower alkyl, lower alkoxy, acylamino, etc.; R<2> is H, lower alkyl, lower alkoxy or halogen; R<3> is H or (substituted) lower alkyl; X is (substituted) phenylene or naphthylene; Y is -SO2CH=CH2 or -SO2C2H4W (W is group removable with alkali); m is 2 or 3]. EXAMPLE:A compound of formula II. USE:For dyes capable of dyeing cellulose fibers, nitrogen-contg. fibers, etc. yellow; capable of dyeing cellulose fibers under dyeing conditions for polyester fibers. PREPARATION:For example, 1mol of a coloring matter of formula III and 1mol of a second coloring matter of formula IV are condensed to form a disazo compound of formula V; with which 1mol of a compound of formula VI is condensed.

Description

Detailed Description of the Invention (a) Purpose of the invention (a) Field of industrial application The present invention relates to a novel disazo compound used as a dye for cellulose 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 pHlo or above, temperature 100
A method is adopted in which the process is carried out at temperatures below ℃.

However, in recent years, the demand for blended fabrics of cellulose fibers and other fibers, especially polyester fibers, etc. has increased, and in order to dye such cellulose/polyester mixed fibers (hereinafter sometimes simply referred to as C/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. In other words, to dye polyester fibers, a didisperse dye is used and the temperature is approximately 130°C.
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, a reactive dye and a disperse dye, which would pose several problems. Ta. In other words, in order to sufficiently dye the reactive dye on the cellulose fiber side, an acid binder is used to
It is necessary to set 1 to 10 or more, but 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, in order to dye the disperse dye on the polyester fiber side,
(usually 130°C), but high pH as above
At lower temperatures, the hydrolysis of reactive dyes is promoted by high temperatures, and dyeing of cellulose fibers is 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 that can dye cellulose fibers under ρ(1) and other dyeing conditions when polyester fibers are dyed with a disperse dye, and a disazo compound containing the same. It is an object of the present invention to provide a dye 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 (1) [wherein M represents a hydrogen atom or an alkali metal, and R1 represents a hydrogen atom, a carboxyl group, a lower alkyl group, a lower alkoxy group, an acylamino group, a carbamoylamino group, or a halogen atom] R2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom, R3 represents a hydrogen atom or a lower alkyl group which may have a substituent, and
represents a phenylene group or a naphthylene group which may have a substituent, and Y is a -5o, CH=CH2 group or a -5O2C, H4W group (::, where W is eliminated by the action of 7/L/potassium. represents a group that separates) and 1m is 2
Or it represents 3. ] The present invention relates to a disazo compound represented by the following and a dye composition containing the disazo compound as a dye component.

In the disazo compound represented by general formula (1) of the present invention, the alkali metal represented by M includes lithium, sodium, potassium, etc., and the lower alkyl group represented by R1, R'' and R1, or the lower alkoxy Examples of the group include a C1-C4 alkyl group or an alkoxy group.

Examples of the halogen atom represented by R1 and R2 include a chlorine atom, a fluorine atom, and a bromine atom.

The acylamino group represented by R1 is an alkyl group or a phenyl group. ).

Examples of the group substituting the lower alkyl group of R3 include a cyano group, a hydroxyl group, a lower alkoxy group, a halogen atom, and a lower alkylcarboxy group.

or 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.

Specific examples of -N-X- include.

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 general formula [11] (where M, R", R", and m are the same as defined above)
The 1 molar proportion of the dye represented by the following formula (m) (wherein, M,
R1* R”, m is the same as defined above) Dye 1
The molar ratio is condensed and the following formula (rV) is obtained.2 (In the formula, Me R'+ R'', m is the same as the above definition)
It is a disazo compound shown by

Then, to the disazo compound represented by the general formula (IV), a compound represented by the following general formula (V) NH-X-Y (V) (wherein R3, X and Y are the same as defined above) The disazo compound of the general formula (1) can be produced by condensing 1 molar proportion of the compound.

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, a disazo compound represented by the above general formula (1) is used at 0.01 to 50 #
IQ degree, 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.
About 0v7ρ, and if necessary, electrolyte (sodium chloride or sodium sulfate, etc.) is usually 1 to 150 gI.
Preferably, a dye bath containing about 40 to 8 og/Q is prepared, and cellulose fibers and nitrogen-containing fibers are added to this dye bath and heated at a temperature of 100 to 150'C for 30 to 50 minutes. It is possible to perform various staining.

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
0.0% of the disperse dye listed in our Index. O1~50
By preparing a dye bath by adding approximately 0.5 to 397i of surfactant (e.g., sulfosuccinic acid-based anionic surfactant, nonylphenol-based nonionic surfactant, etc.) 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 in which one fiber is dyed and then the other fiber is dyed in the same bath is used. Furthermore, a two-bath method 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

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 by dissolving it in water during dyeing. , as mentioned above, the disazo compound represented by the general formula [1] is mixed with 0.01 to 50
g Contains about IQ, buffering agent 0.5-5.09IQ,
An aqueous solution containing about 1 to 150 g/l of electrolyte is common. In the case of a concentrated liquid or paste, the above-mentioned disazo compound can be contained up to about 200 d/Q.

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

Example 1 1 mole proportion of a monoazo dye represented by the following formula and 1 mole proportion of a monoazo dye expressed by the following formula were mixed in an aqueous medium.

A disazo compound represented by the following formula is produced by condensation at 30 to 40°C, and 3-(
β-Hydroxyethyl)sulfonyl N-methylaniline sulfate (1 molar proportion) was added and condensed at 90°C, followed by salting out with potassium chloride to obtain the following structural formula (shown in free acid form) and visible light absorption. A disazo compound having an analysis value according to the method was obtained.

(λlla!: 390 nm (water)) Next, 0.2 g of the above disazo compound, Glauber's salt 164) and Na as a buffer.
2tlP0.12+1.00.4i and Kl(2PO
40.1q was added to 200aQ of water to adjust the pH to 7. 10I of unmercerized cotton stockinette was added to the dye bath, and the temperature was raised to 120℃ over 30 minutes. After dyeing at the same temperature for 60 minutes, washing with water, A yellow dyed product was obtained by soaping, washing with water, and drying. 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 unmercerized cotton stockinette 10 in Example 1 was changed to wool muslin 109.

As a result, the wool muslin was dyed very intensely yellow.

Example 3 A disazo compound represented by the following formula was produced by condensing 1 mole of a monoazo dye represented by the following formula and 1 mole of a monoazo dye represented by the following formula in an aqueous medium at 30 to 40°C, 3- in the reaction solution
(β-Hydroxyethyl)sulfonyl N-ethylaniline sulfate in a 1 molar proportion was added and condensed at 90°C, followed by spray drying to obtain the following structural formula (shown in free acid form).

) and a disazo compound having analytical values based on visible light absorption was obtained.

Next, 0.2 g of the above disazo compound, 16 g of Glauber's salt, Na as a buffer, HPO412H, Oo, sy and KH,
Unmercerized cotton stockinette lOζ was placed in a dye bath prepared by adding PO40,029 to 200 mQ of water, heated to 130°C over 30 minutes, and dyed at the same temperature for 30 minutes.
A reddish yellow dyed product was obtained by washing with water, soaping, washing with water, and drying. The pH of this dyeing bath was 8 before and after dyeing. The resulting dyeing is extremely dense and lightfast.

Both chlorine fastness and sweat-sunlight fastness were good.

Example 4 A disazo compound represented by the following structural formula in the form of free acid 0.29, a quinophthalone dye represented by the following structural formula 0.2, sodium sulfate 129° as a buffer, Na, HPo, 12H,00,4# and KH,
Ten pieces of blended fabric of polyester/cotton = 50:50 were placed in a dye bath prepared by adding PO40,19 to 200 mG of water, heated to 130°C over 30 minutes, and dyed at the same temperature for 60 minutes. Thereafter, washing with water, soaping, washing with water, and drying were performed to obtain a yellow dyed product with good same color property. This dyeing bath is used before dyeing.
Later it was p118. 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) as shown in Table 1 below were prepared. 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 1O-Na, HPO,
12H2010g Kl, PO43g water 200a
Q: The above composition can be used to prepare a dyebath by diluting it with 10,000 aQ of water.

Example z9 A concentrated dye composition was obtained by blending the following components.

Disazo compound of Example 3 1g Na, HPo, 12H202,5P Kll, PO40, 1g Glauber's salt 25
9 Wed '200
mQ The above composition can be diluted with 800 mQ of water to prepare a dyebath at the time of use.

(c) As shown in the detailed description of the invention and in the examples, the present invention provides a novel disazo compound and uses it together with a dye to dye polyester fibers with monodisperse dyes. Cellulose fibers can be dyed well even under the actual pH and other dyeing conditions, and therefore, even when cellulose/polyester mixed fibers are dyed, there is no need for a separate bath as in the conventional method.

Claims (12)

[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 carboxyl group, a lower alkyl group, a lower alkoxy group, an acylamino group, a carbamoylamino group, or a halogen atom; R^2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom; R ^3 represents a hydrogen atom or a lower alkyl group that may have a substituent, X represents a phenylene group or a naphthylene group that may have a substituent, and Y represents a -SO_2CH=CH_2 group or -SO_2C_2H
_4W group (here, W represents a group that is eliminated by the action of an alkali), and m represents 2 or 3. ] A disazo compound represented by (2) The disazo compound according to claim 1, wherein R^3 is a hydrogen atom or a lower alkyl group substituted with a cyano group, a hydroxyl group, a lower alkoxy group, a halogen atom, or a lower alkylcarboxy group. (3) A patent claim in which X is a phenylene group or naphthylene group substituted or unsubstituted with one or two substituents selected from the group of lower alkyl groups, lower alkoxy groups, halogen atoms, and sulfonic acid groups. A disazo compound according to item 1. (4) 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. (5) 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 R
^1 represents a hydrogen atom, a carboxyl group, a lower alkyl group, a lower alkoxy group, an acylamino group, a carbamoylamino group, or a halogen atom; R^2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom; R ^3 represents a hydrogen atom or a lower alkyl group that may have a substituent, X represents a phenylene group or a naphthylene group that may have a substituent, and Y represents a -SO_2CH=CH_2 group or -SO_2C_2H
_4W group (here, W represents a group that is eliminated by the action of an alkali), and m represents 2 or 3. ] A dye composition characterized by containing a disazo compound represented by the following. (6) The dye composition according to claim 5, wherein R^3 is a hydrogen atom 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. (7) A patent claim in which X is a phenylene group or naphthylene group substituted or unsubstituted with one or two substituents selected from the group of lower alkyl groups, lower alkoxy groups, halogen atoms, and sulfonic acid groups. The dye composition according to item 5. (8) The dye composition according to claim 5, wherein W is a sulfate group, a thiosulfate group, a phosphate group, an acetate group, or a halogen atom. (9) The dye composition according to claim 5, wherein the dye composition is a composition containing water and a dyeing aid. (10) The dye composition according to claim 9, wherein the dyeing auxiliary agent is a buffer, an electrolyte, and a surfactant. (11) The dye composition according to claim 10, wherein the buffering agent is carbonic acid, phosphoric acid, acetic acid, citric acid, boric acid, or a salt thereof. (12) The dye composition according to claim 10, wherein the electrolyte is sodium chloride or sodium sulfate.