JPS61272271A - Azo lake pigment composition - Google Patents

Abstract

PURPOSE:To obtain the titled composition with good printing ink suitability free from characteristics degradation, stain development, etc., by substituting specific anilide- and/or pyrazolone-based compound(s) for part of a naphthol- based grounder component. CONSTITUTION:The objective composition can be obtained by substituting (A) 0.2-30mol% of a naphthol-based grounder component such as beta-naphthol or beta-oxynaphthoic acid with (B) (i) an anilide compound of formula I (X is one or more groups selected from H, halogen, methoxy, ethoxy, methyl, ethyl, nitro, carboxyl, sulfonic acid, carboxylic acid amide and sulfonic acid amide) or/and (ii) a pyrazolone compound of formula II (Y is methyl or carboethoxy).

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 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, in addition to the above properties, azo lake pigments are required to have transparency, sharpness, coloring power, gloss, etc. when used in printing inks, so they cannot be used in conventional printing inks. In order to meet these demands, azo lake pigments 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 azo lake pigments have transparency, sharpness,
Although coloring power, gloss, etc. have been improved to some extent, these properties often deteriorate due to the various 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 producing an azo lake pigment, a part of the base-side component used is replaced with another base-side agent having 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 the conventionally known 7 azo lake pigments.

(Means for Solving the Problems) That is, in the production of an azo lake pigment, the present invention provides 0.2 to 30 mol% of the naphthol-based subdivision side component to the following formula (
I) or the following formula (T
This is an azo lake pigment composition obtained by substitution with at least one pyrazolone compound represented by I).

However, X in the above formula is one or more hydrogen atoms, halogen atoms, methoxy groups, ethoxy groups, methyl groups, ethyl groups,
They are a nitro group, a carboxyl group, a sulfonic acid group, a carboxylic acid amide group, and a sulfonic acid amide group, and may contain two or more of these substituents at the same time, while Y is a methyl group or a carboethoxy 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, Bellja Orange, Scarlet Lake, Bordeaux B, Pigment Fist Scarlet 3B, First Ride Yellow 3G, Tartrazine Lake, Lysol.
Red, Red Rake C Rud Rake D.

Brilliant Carmiso 6B, Permanent Red 2B,
Red Lake P is a typical example, and the method for producing such azo lake pigments is already well known. A water-soluble or slightly water-soluble dye is prepared by coupling a diazonium salt of an aromatic primary amine, and this is treated with barium, calcium, aluminum, or as a lake agent.
It is obtained by reacting polyvalent metal ions such as strontium, manganese, nickel, etc. to make them insoluble in water.

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 layer agent such as beta-naphthol or beta-oxynaphthoic acid is mixed with the general formula CI) or (II). ) is substituted with at least one of the following compounds.

The compound of the general formula (I) or (II) is itself a well-known compound as a conventionally known subbing agent for azo pigments, and any of these well-known compounds can 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 homogeneous azo lake pigments, in order to use them as 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 azo lake pigment composition of the present invention already has excellent suitability for printing inks without the need for such treatment, and therefore, it does not require any additives or It has been found that there are no defects caused by the processing agent.

In the present invention, even if the amount of the compound of the general formula (I) or (II) mixed is small, an azo lake pigment with excellent transparency, sharpness, coloring power, gloss, etc. can be obtained. If the amount of at least one of the compounds of general formula CI) or (II) used is less than 0.2 mol%, the desired effect of the present invention will be low, and if the amount used exceeds 30 mol%, In this case, the original excellent properties of the azo lake pigment are deteriorated, which is undesirable.The most effective range of the amount used is 0.3 to 1.0 mol%.

The method for producing the 7-solex pigment composition of the present invention using the above-mentioned raw materials can be carried out in accordance with the conventionally known method for producing 7-solex pigments.

That is, an aromatic primary amine is diazotized according to a conventional method, while a predetermined amount of the above general formula (I) or (II) is diazotized.
A precipitant is prepared according to a conventional method using a mixture consisting of at least one of the compounds of By lake-forming with manganese, nickel, aluminum, etc., the 7-layer pigment composition of the present invention with improved various properties can be obtained.

Further, in the above production method, general formula (I) or (rl
) with at least one compound of general formula (I) or (II). The same effect can be obtained even if the azo lake pigment obtained without substituting the species is mixed and the proportion of at least one compound of general formula CI) or (II) is adjusted to 0.2 to 30 mol% of the basting agent. It is.

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

The azo lake pigment composition of the present invention as described above 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.

(Function/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 While the Azo Lake pigment has the above-mentioned drawbacks when used in printing inks, the Azolake pigment composition according to the present invention overcomes these drawbacks. Furthermore, when using Azole Lake pigments 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, but with conventional 7 So Lake pigments, during this flushing operation, Pigment particle growth occurred and a significant reduction in tinting power occurred.

However, the azo lake pigment composition obtained according to the present invention does not suffer from such drawbacks even if 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 printing inks.

Next, the present invention will be explained in more detail with reference to Examples. In addition, parts and percentages in the text are based on weight unless otherwise specified.

Example 1 2-chloro-5-amine toluene-4-sulfonic acid was diazotized by a conventional method, and this was converted into beta-naphthol 97
A sodium dye is prepared by coupling mol % and 3 mol % of acetoacedoanilide to a base preparation prepared by dissolving it. Rosin (2 parts per 100 parts of pigment to be obtained) was injected into the dye, the temperature was raised to 95°C, and barium chloride solution (
1.4 mol of barium chloride is used per 1 mol of dye) 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 ground, 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 a compound of general formula CI) or (II). Compared to pigments obtained without the use of pigments, the pigments were clearer, more vivid, had more coloring power and gloss, and had excellent suitability for printing inks.

Example 2 98 mol% beta-naphthol and 4-chloro-2,5-
An azo lake pigment composition of the present invention was obtained in the same manner as in Example 1 except that 412 mol % of dimethoxyacetoacedoaniline was mixed to prepare a base agent.

As a result, the azo lake pigment composition of the present invention obtained is as follows:
Compared to pigments obtained without using the compound of general formula (I) or (II), the pigments were clearer and more vivid, had higher tinting power and gloss, and had excellent suitability for printing inks.

Example 3 An azo lake pigment composition of the present invention was obtained in the same manner as in Example 1 except that 98 mol% of beta-naphthol and 2 mol% of 2-acetoacetaminobenzoic acid were mixed to prepare a base. .

As a result, the azo lake pigment composition of the present invention obtained is as follows:
Compared to pigments obtained without using the compound of general formula (I) or (II), the pigments were clearer and more vivid, had higher tinting power and gloss, and had excellent suitability for printing inks.

Example 4 4-Aminotoluene-3-sulfonic acid was diazotized by a conventional method, and this was cupped in a base preparation prepared by mixing 97 mol% of beta-oxynaphthoic acid and 3 mol% of 7cetoacetanilide. ring to make sodium dye. The dye contains rosin (10 parts per 100 parts of the resulting pigment)
and a calcium chloride solution (1.4 moles of calcium chloride used per 1 mole of dye) to form a lake.

This slurry is heated to 80°C and aged for 20 minutes.

This is filtered, washed with water, and made into a press cake. In addition, a portion of the ink is dried, pulverized, made into ink, and tested 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 pigments obtained without using the compound of general formula (I) or (II), it is clearer, more vivid, has more coloring power, and has gloss.
It had excellent printing ink suitability.

Example 5 95 mol% beta-oxynaphthoic acid and 1-phenyl-
An azo lake pigment composition of the present invention was obtained in the same manner as in Example 4 except that 5 mol% of 3-methyl-5-pyrazolone was mixed to prepare a base.

As a result, the azo lake pigment composition of the present invention obtained is as follows:
Compared to pigments obtained without using the compound of general formula (I) or (II), the pigments were clearer and more vivid, had higher tinting power and gloss, and had excellent suitability for printing inks.

Example 6 2-Chloro-4-7minotoluene-5-sulfonic acid was diazotized by a conventional method, and this was mixed with 98 mol% of beta-oxynaphthoic acid and 412 mol% of 2,4-dimethoxyacetoacedoanilate. Coupling with prepared basting agent to create sodium dye. The temperature of the dye is raised to 90° C., a barium chloride solution (1.4 moles of barium chloride is used per 1 mole of dye) is added to form a lake, and the mixture is 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 obtained seven-layer pigment composition of the present invention is as follows:
Compared to pigments obtained without using the compound of general formula (I) or (II), the pigments were transparent, bright, bright, had coloring strength, and gloss, and had excellent suitability for printing inks.

Example 7 2-Chloro-5-amine toluene-4-sulfonic acid is diazotized by a conventional method, and this is coupled with a base preparation in which beta-naphthol is dissolved to produce a sodium dye. To 97 mol % of the dye, 3 mol % of a dye obtained by diazotizing 2-chloro-5-aminetoluene-4-sulfonic acid and coupling with acetoacedoanilide by a conventional method is added. Rosin (obtained pigment 1) is added to the mixed slurry.
00 parts), heated to 95°C, and added barium chloride solution (1.4 parts of barium chloride per 1 mole of dye).
molar amount) to form a lake.

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.

In the case of λkagyoushi press cake, pigment press cake (solid content 10
0 parts) to 600 parts of resin varnish and test flasher.
Flushing is carried out with the ink, and then it is made into ink using a conventional method.

In the case of pigment powder, 100 parts of pigment is mixed with 60 parts of resin varnish.
In addition to 0 parts, it is dispersed with a Miki roll and made into ink. To evaluate the ink, make a proof print on black obi art paper using an RI tester.
Comparisons will be made in terms of transparency, sharpness, coloring power, gloss, etc.

Claims (1)

[Claims] In the production of the azo lake pigment, 0.2 to 30 mol% of the naphthol base preparation component is an anilide compound represented by the following formula (I) or a pyrazolone compound represented by the following formula (II). An azo lake pigment composition obtained by substitution with at least one of the following. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (However, X in the above formula is one or more hydrogen atoms, halogen atoms, methoxy groups, ethoxy group, methyl group, ethyl group, nitro group, carboxyl group, sulfonic acid group, carboxylic acid amide group, sulfonic acid amide group, and may contain two or more of these substituents at the same time.Y is a methyl group or carboethoxy group.)