JPS58174446A - Azo pigment and its preparation - Google Patents

Abstract

NEW MATERIAL:The azo pigment of formula I (R1 is residue of aromatic primary mono-amide; R2 is residue of phenylenediamine, etc.). USE:Red pigment having excellent light fastness, solvent resistance, heat resistance, acid resistance, alkali resistance, water resistance, coloring power, etc. PROCESS:The objective pigment can be prepared either by reacting the compound of formula II with the compound of formula III, or by reacting the compound of formula IV with the compound of formula V [Y is Cl2, (OCH3)2 or NH], or by coupling the diazonium compound of an aromatic primary mono-amine with the compound of formula IV.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel azo pigment, and an object of the present invention is to provide an azo pigment with excellent light resistance, solvent resistance, heat resistance, coloring power, etc.

A large number of azo pigments are known in the art and have a wide range of uses. However, the reality is that an azo pigment with sufficient performance has not yet been obtained.

As a result of research to improve various fastness properties of azo pigments, particularly weather resistance and solvent resistance, the present invention found that azo pigments represented by the general formula (p) shown below have excellent various properties. The invention has been completed.

That is, the present invention is an azo pigment represented by the following general formula (2) and a method for producing the same.

〇In the above formula, lla is an aromatic aromatic primary monoaonic group, and - is a residue of phenylenediamines.

To explain the present invention in detail, the azo pigment of the present invention can be obtained by the following method.

A compound represented by the following general formula (] II (an actual crocodile conductor) obtained by coupling 2-hydro-3-naphthoic acid with an arbitrary aromatic primary monoathane diazonium compound; A method of reacting a compound represented by the following general formula (1).

The first aromatic used in this method! ! As the monoamine, any monoamine that is used as a base in the production of conventional azo pigments can be used; for example, Tokkosho! 1-749
Monoamines described in Publication No. 1 can be used.

The compound represented by the above general formula (seal) itself is known, for example, Tokkosho! 6-2J6! Any of those described in the above publication can be used ◇The above general formula (I[)
The reaction between the compound represented by the formula (1) and the compound represented by the above general formula (1) is carried out in an inert solvent such as benzene, xerbenzene, alkylbenzene, nitrobenzene, etc. This can be easily carried out according to a conventional method by using a halogenated compound such as phosphorus oxychloride, etc., and the general formula α
) is obtained.

(-Reaction between a compound represented by the following general formula (W)' and a compound represented by the following general formula (v).

□.

R□ in the above formula has the same meaning as above, ■ is NH,
rocas) or α.

The compound represented by the above general formula (W) is a compound represented by the general formula (W).
When the compound represented by II) (or its functional compound) is reacted with nitroaniline, etc. which may have other substituents, and then the existing nido four groups are converted into 7z groups Kl1, K is obtained.・The above general compound is 3-iono-1-oxoinoindoline, 3.3-dimethoxy-1-oxoisoindoline or 3.3-dichloro-
It is a nuclear halide of 1-oxoisoindoline. The reaction between the compound represented by the general formula (W) and the compound represented by the general formula ω can be carried out according to a conventional method to obtain the azo pigment of the present invention.

e→A method in which a compound represented by the following general formula (V) is used as a coupling component, an aromatic primary monoamine is used as a diazo component, and the two are reacted.

12 in (4) has the same meaning as above. The compound represented by the above general formula (W) can be obtained by reacting the compound of the above general formula (C) with 2-hydroxy-3-7toic acid in the same manner as in the above method (I). This general formula (■)
The azo pigment of the present invention can be obtained by coupling a diazonium salt of an aromatic primary heptanoane to the compound in accordance with a known method.

The azo steel produced by the method of the present invention as described above has excellent solvent resistance, and also has good light resistance, heat resistance, water resistance, acid resistance, and alkali resistance. It has extremely high coloring power and can be used satisfactorily as an azo pigment. That is, as a solvent resistance test, the azo pigment of the present invention 0.
Place 5F in a test tube, add 10@. of a solvent such as methylinobutylketone, methylalco-yl toluene, acetate, cellosolve acetate, general spirit, butyl alcohol, ethyl acetate, trichlene, etc., and shake for a while. When the supernatant liquid was left to stand for a while, the supernatant liquid was hardly colored.

As a heat resistance test, the azo pigment obtained by the method of the present invention was kneaded with a color vehicle to form a paste, which was applied to a tin plate, and the tin plate was treated at 200°C for 1 hour using an electric furnace. As a result, the color change was hardly observed in #1.

Furthermore, it showed sufficiently satisfactory results as an azo pigment in tests such as light resistance, acid resistance, alkali resistance, and water resistance.

Next, the present invention will be specifically explained with reference to Examples.In the Examples, parts are based on weight.

Example 1 16.2 parts of 1-amino-λ5-dichlorobenzene is cydiazotized in dilute hydrochloric acid in a conventional manner to obtain a diazonium salt solution. On the other hand, 54.5 parts of the compound represented by the general formula (W) (phantom; P-phenylene group) is dissolved in a mixture consisting of 400 parts of methanol and 130 parts of 2N aqueous sodium hydroxide solution. A coupling reaction is carried out by mixing the diazonium salt solution and the submerging solution at about SO for minutes. After that, heat treatment at 50-60℃ for 1 hour, filtration,
After washing with water and drying, the lice □ in the above general formula □ is 2.5-
A red pigment of the present invention was obtained in which the dichlorophenyl group was a P-phenylene group. The lightfastness of this pigment,
Knee performance such as solvent resistance was good.

Example 2 8.4 parts of 1-amino-2-methoxy-5-nitrobenzene is cydiazotized in dilute hydrochloric acid by a conventional method to obtain a diazonium salt solution. On the other hand, 27.3 parts of a compound of the general formula (I in which - is m-phenylene group) is dissolved in a mixture consisting of 400 parts of methanol and 65 parts of 2N caustic soda to prepare a submerging solution.

The above diazonium salt solution and the above submerging solution are mixed for about 30 minutes, a coupling reaction is performed, and the temperature is further increased to 60-65℃.
After mixing and stirring for 1 hour, the press cake was filtered and washed with water.
After removing moisture, heat treatment is performed at 200°C for 2 hours. Cooling, filtration, washing with methanol, washing with water, drying, and in the general formula fD, the wing □ is a 2-methoxy-5-nitrophenyl group, l! Azo pigment 3 of the present invention in which is m-phenylene group
6 parts were obtained.

This pigment had good light resistance, solvent resistance, and other properties.

Examples 3 to 58 Various pigments of the present invention shown in Table 1 below were obtained using the raw materials shown in Table 1 below in the same manner as in Examples 1-4.

Table
7.5 parts of a compound in which l is a phenylene group were added to 250 parts of rhodichlorobenzene, and 140-14
After reacting at 5°C for 6 hours, the mixture was cooled, filtered and washed to obtain 14.0 parts of an azo pigment having the same structure as Example 1f).

Examples 60 to -3 In the same manner as in Example 59, the raw materials listed in Table 2 below were used to obtain various azo pigments listed in Table 2 below.

Table 2 Example 64 441 parts of a compound in which 11 is a &5-dichloro7enyl group and - is a P-phenylene group in the general formula (W), and a compound atom in which the general formula ω is Q. 9o
In addition to o parts of 0-dichlorobenzene, 120 to 1! After reacting in IC for 3 hours, the mixture was cooled, filtered, and washed to obtain 70 parts of a red pigment having the same structure as the pigment of Example 1.

Example 6s Instead of the compound of general formula m in Example 64, 28.4 parts of a compound of general formula ω where τ is NH,
Otherwise, 70 parts of a red pigment having the same structure as the pigment of Example 1 was obtained in the same manner as in Example 65.

Examples 66 to 79 In the same manner as Examples 64 to 6S, the raw materials listed in Table 3 below were used to obtain various pigments listed in Table 1 below.

Claims (2)

[Claims] (1) Azo pigment represented by the following general formula (Il). (2) A compound represented by the following general formula (II) and a compound represented by the following general formula (1) are reacted, or a compound represented by the following general formula (W) and the following general formula (
V) or by coupling a diazonium compound of an aromatic primary monoamine to a compound represented by the following general formula (W). A method for producing an azo pigment represented by I). 2μ (In the above formula, 11 is a residue of aromatic primary monoagine, - is a residue of phenylenediamine, Y
#iCt, , (OCHs)*t or NH. )