JPS61203176A - Azo lake pigment composition - Google Patents

Abstract

PURPOSE:To prepare an azo lake pigment having an excellent suitability for use as a printing ink, by replacing a part of a grounder component with a specific compound in preparing an azo lake pigment. CONSTITUTION:An an azo lake pigment is prepared by replacing 0.2-30mol% grounder such as beta-naphthol or beta-hydroxynaphtoic acid, which is used in a method of preparing an azo lake pigment, with a compound of the formula I. The compound of the formula I can be prepared by reacting beta- hyroxynaphthoic acid with aniline or various aniline derivatives. When the amount of the compound of the formula I used is less than 0.2mol%, the effect obtained is not satisfactory while, when the amount exceeds 30mol%, the excellent properties inherent in the azo lake pigment is unfavorably spoiled.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to an azo lake pigment, and relates to an azo lake pigment composition useful for various uses, particularly as a pigment for printing inks.

(Prior Art) Azole lake pigments have been widely used in particular for coloring printing inks, synthetic resin paints, rubbers, etc. because of their good solvent resistance and light resistance. Among these uses, 7-solake pigments, especially when used for printing inks, are required to have increased transparency, sharpness, coloring power, gloss, etc. in addition to the above-mentioned properties. Therefore, in order to meet these demands, conventionally known azo lake pigments for printing inks are treated with additives and processing agents such as natural resins such as rosin, metal soaps, and surfactants.

(The problem that the invention is trying to solve) However,
The above-mentioned conventionally known 7solake pigments have transparency, sharpness,
Although tinting power, gloss, etc. have been improved to some extent, these properties often deteriorate due to the additives and processing agents used, and various problems such as scumming occur, so it is not always sufficient. It did not have good printing ink suitability.

As a result of intensive research in order to solve the above-mentioned drawbacks of the prior art, the present inventor has discovered that when manufacturing an azo lake pigment, a part of the base agent component used is replaced with another base agent with a specific structure. completed the present invention after discovering that an azo lake pigment having excellent suitability for printing inks can be obtained without using additives or processing agents that cause various problems like conventionally known azo lake pigments.

That is, 1. The present invention is an azo lake pigment composition obtained by replacing 0.2 to 30 mol% of the base agent component with a compound represented by the following formula (I) during the production of the azo lake pigment. be.

(2) However, X in the above formula is one or more water-insoluble groups such as hydrogen, halo, gen atom, methoxy group, ethoxy group, methyl group, ethyl group, nitro group, substituted amino group.

Next, to explain the present invention in more detail, the azo lake pigment referred to in the present invention is an azo dye having a water-soluble group such as a sulfonic acid group or a carboxylic acid group, which is treated with a polyvalent metal ion such as an alkaline earth metal. For example, Bell Jar Orange, Scarlet Fist Lake, Bordeaux B, Pigment War Scarlet 3B, First Light Yellow 3G, Tartrazine Lake, Lysol Red, Red Lake C, Red Lake D, Red.・Lake P is a typical example, and the manufacturing method of such azo lake pigments is already well known. A water-soluble or slightly water-soluble dye is prepared by coupling diazonium salts of various aromatic primary amines to the dye, and then barium, calcium, aluminum, strontium, manganese, nickel and other polyvalent metal ions are added to the dye. They are obtained by reacting and making them insoluble in water, and the manufacturing methods themselves are all well known.

The main feature of the present invention is that in the well-known method for producing azo lake pigments, 0.2 to 30 mol% of the base agent such as beta naphthol or beta oxynaphthoic acid used is
is substituted with the compound of the general formula (I).

The compound of the general formula (I) is obtained by reacting beta-oxynaphthoic acid with aniline or various aniline derivatives, and this compound itself is well known as a pre-layering agent for conventionally known insoluble azo pigments. These well-known compounds can all be used in the present invention.

According to the inventor's detailed research, the 7-solet pigment composition of the present invention thus obtained has superior suitability for printing inks compared to conventionally known homogeneous azo-lake pigments. In the case of conventional azo lake pigments of the same type, in order to use them for printing inks, it is necessary to treat them with various additives and processing agents as mentioned above, and as a result, various troubles as mentioned above occur. However, the pigment composition of the present invention already has excellent suitability for printing inks without the need for treatment with such conventionally known additives and processing agents. Therefore, it has been found that there are no defects caused by the additives or processing agents used as in the prior art.

If the amount of the compound of general formula (I) used is less than 0.2 mol%, the desired effect of the present invention will be low, and if the amount exceeds 30 mol%, the original azo lake pigment will be damaged. The most effective range of usage is from 0.3 to 10 mol %, which is not preferred because the excellent properties are reduced.

The method for producing the azo lake pigment composition of the present invention using the above-mentioned raw materials can be carried out in accordance with conventionally known methods for producing azo lake pigments.

That is, the above-mentioned aromatic primary amine is diazotized according to a conventional method, and on the other hand, a pre-soaking solution is prepared according to a conventional method using a mixture consisting of a predetermined amount of the compound of the above-mentioned general formula (I) and a presoaking agent. The 7 sol of the present invention has improved various properties by mixing and coupling the two in a conventional manner and then forming a lake with a metal salt such as an alkaline earth metal or manganese, nickel, aluminum, etc. A single pigment composition is obtained.

In addition, in the above production method, after replacing more than 30 mol% of the base preparation with the compound of general formula (I) and performing a coupling reaction in the same manner, the compound of general formula (I) is substituted. The same effect can be obtained by mixing the azo lake pigment obtained without using the base preparation and adjusting the usage ratio of the compound of general formula (I) to 0.2 to 30 mol % of the base preparation.

Furthermore, a 7-sol pigment using only the compound of general formula (I) is prepared in advance, and this is mixed with a general 7-sol pigment in a predetermined ratio to form the 7-sol pigment composition of the present invention. When using such a post-mixing method, which may be prepared, it is preferred that the azo lake pigment to be mixed is an azo dye prior to lake formation.

The above-mentioned seven-layer pigment composition of the present invention can be prepared according to a known method during or after coupling.
Pigment treatment can also be carried out by adding various aliphatic amines, various water-soluble resins, surfactants, and other additives and processing agents to an extent that does not impede the object of the present invention.

(Effect) The azo lake pigment composition obtained by the present invention as described above has improved transparency, sharpness, coloring power, gloss, etc. compared to conventional azo lake pigments of the same type, and 7. Solake pigments have the above-mentioned drawbacks when used in printing inks.

The seven-layer pigment composition according to the present invention overcomes these drawbacks. Furthermore, when Azole Lake pigments are used in paints and printing inks, a method is used in which the Azole Lake pigments are transferred from an aqueous pigment paste to an organic phase by a flushing method. Pigment particle growth occurred and a significant decrease in tinting power occurred.

However, the azo lake pigment composition according to the invention does not suffer from any of these drawbacks even when the operating temperature increases during flushing.

The present invention has been described above, particularly with respect to the use of printing inks, but the azo lake pigment composition of the present invention is also useful for other uses, and is not limited to use in printing inks.

Next, the present invention will be specifically explained with reference to Examples. In addition,
In the text, parts or percentages are by weight unless otherwise specified.

Example 1 2-chloro-5-7minotoluene-4-sulfonic acid was diazotized by a conventional method, and this was mixed with 95 mol% of beta-naphthol and 5 mol% of 2-hydroxynaphthalene-3-carboylanilide. Coupling with the pre-prepared preparation to create a sodium dye. The dye is rosin (
2 parts per 100 parts of the pigment obtained) is injected, the temperature is raised to 95°C, and a barium chloride solution (1.4 mol of paris rum chloride is used per 1 mol of dye) is added to form a lake.

This is filtered and washed with water to form a press cake. In addition, a part of it is dried and crushed, and tested by making it into an ink according to the test method described below.As a result, the obtained 7-sol pigment composition of the present invention is clearer and clearer than the non-tested product. ,
It had good tinting strength and gloss, and had excellent printing ink suitability.

Example 2 2-chloro-4-7minotoluene-5-sulfoso-3-
A sodium dye is prepared by coupling to a subsoak solution prepared by mixing 3 parts of carboyl-2'-methoxy-5'-chloroanilide. The dye was heated to 90°C,
Barium chloride solution (1 mole of dye to 1 barium chloride solution)
．． 4 mol (used) was added to form a lake, and aged for 20 minutes.

This is filtered and washed with water to form a press cake. In addition, a portion of the ink is dried and ground, and then tested by making an ink according to the test method described below.

As a result, the azo lake pigment composition of the present invention obtained is as follows:
Compared to the non-examined product, it was clearer, clearer, had more coloring power and gloss, and had excellent suitability for printing inks.

Example 3 4-7 minotoluene-3-sulfonic acid was diazotized from ochreafthoace in a conventional manner, and this was beta-extended to a concentration of 95 mol%.
and 2-hydroxynaphthalene-3-carboyl-4'-
Coupling with a subsoaking solution prepared by mixing 5 mol% of chloranilide to produce a sodium dye. Rosin (10 parts per 100 parts of the pigment to be obtained) is injected into the dye, and a calcium chloride solution (1.4 mol of calcium chloride is used per 1 mol of dye) is poured into the dye to form a lake. This slurry is heated to 80°C and aged for 20 minutes. Filter this,
It is washed with water and made into a press cake, and a part of it is dried and crushed, and then tested by making it into an ink according to the test method described below.

As a result, the obtained seven-layer pigment composition of the present invention is as follows:
Compared to the non-conducting product, it was clearer, clearer, had more tinting strength and gloss, and had excellent suitability for printing inks.

Example 4 Instead of 2-hydroxynaphthalene-3-carboyl-4'-chloroanilide in Example 3, ? -Hydroxynaphthalene-3-carpoylanilide also had the same effect as in Example 3.

Example 5 2-chloro-5-amine toluene-4-sulfonic acid is diazotized by a conventional method, and this is coupled with a precipitate solution in which beta-naphthol is dissolved to produce a sodium dye. To 95 mol % of the dye, 5 mol % of a dye prepared by diazotizing 2-chloro-5-aminotoluene-4-sulfonic acid and coupling it with 2-hydroxynaphthalene-3-carpoylanilide is added. Rosin (2 parts per 100 parts of the pigment to be obtained) was poured into the mixed slurry, the temperature was raised to 95°C, and a barium chloride solution (1.4 moles of barium chloride was used per 1 mole of dye) was added. Turn into a rake.

The thus obtained 7-layer pigment composition of the present invention had the same effects as the 7-layer pigment composition of Example 1.

The printing ink suitability test in the above examples was conducted as follows.

For Eka Gogo press cake, use pigment press cake (solid content 10
0 parts) was added to 600 parts of resin varnish, flushed with a test flasher, and made into ink using a conventional method.

In the case of pigment powder, 100 parts of pigment is mixed with 60 parts of resin face.
In addition to 0 parts, it is dispersed using three rolls and made into ink. The ink was evaluated by making a proof print on black-banded art paper using an RI tester, and comparing transparency, sharpness, color strength, gloss, etc.

Procedural amendment (voluntary) April 26, 1985

Claims (1)

[Scope of Claims] In the production of azo lake pigment, 0.2 to 3
An azo lake pigment composition obtained by replacing 0 mol% with a compound represented by the following formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (However, X in the above formula is one or more hydrogen, halogen atom, methoxy group, ethoxy group, methyl group, ethyl group, nitro group, substituted amino group water-insoluble groups such as