JP2000053879A - Azo lake pigment and its preparation - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a compsn. which has excellent dispersibility and fluidity and gives a nonbronze glossy ink by adding an aliph. prim. amine to a diazo liquid, a grounding liquid, or a dye or pigment slurry in producing an azo lake pigment. SOLUTION: A diazo liquid of a diazo component (e.g. 1-amino-4- methylbenzene-2-sulfonic acid) is added to a grounding liquid comprising a coupling component (e.g. β-oxynaphthoic acid) to cause coupling, thus synthesizing a dye. A metal salt (e.g. calcium chloride) is added to the dye to cause chelation. Then, 100 pts.wt. pigment is stirred together with 0.1-10 pts.wt. aliph. prim. amine soln., filtered, and dried, giving an azo lake pigment compsn. Examples of the azo lake pigment are Brilliant Carmine 6B, Permanent Red 2B, and Lake Red C. Examples of the aliph. prim. amine are octylamine, dodecylamine, tetradecylamine, and beef tallow alkylamine.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an azo lake pigment which is excellent in dispersibility and fluidity, has no bronze (non-bronze) when used for a printing ink, especially a lithographic ink, and can provide a glossy printed matter.

[0002]

2. Description of the Related Art Conventionally, azo lake pigments obtained from a diazonium salt of an aniline derivative having a water-soluble group and β-naphthol or β-oxynaphthoic acid have good solvent resistance, light resistance, etc. Widely used for coloring plastics, paints, etc., especially Pigment Red 5
7 (CI. 15850) is used in large quantities as a red pigment for process inks.

[0003] In this process printing method, a printing ink having excellent transparency is required because multicolor overprinting is performed, and the conventional Pigment Red 57 is used to prepare a diazo component at the time of pigment production for improving transparency. Alternatively, various kinds of accessory treatments having different structures are performed on the coupling component (for example, Japanese Patent Publication No. 3-69380, Japanese Patent Publication No. 7-4).
No. 9537) and a rosin treatment is performed.
However, since transparent pigments are fine and easy to coagulate and disperse poorly, treatment with various treating agents is performed for the purpose of improving these. For this reason, printing problems such as plate stains are likely to occur during printing, and in most cases, printed matter is bronze, and there is no transparent pigment having sufficient suitability.

In order to improve the dispersion and fluidity of the pigment,
Many treatment agents have been proposed so far. For example, treating a pigment slurry with various nonionic or anionic surfactants or metal salts thereof, amines, diamines, etc. is disclosed in French Patent No. 14917140, Japanese Patent Publication No.
No. 28036, JP-B-47-45410, JP-B-48-1821 and the like. When such a treating agent is used, the dispersibility and fluidity of the pigment are improved, but the bronze is not improved. For example, rosin amine which is an aromatic primary amine (for example, amine D
When (Rika Hercules Co., Ltd.) is used, powder-type pigments have less re-agglomeration during pigment pulverization, so that the dispersibility in a three-roll mill is improved and the fluidity is also improved. When this pigment is used as a paste type, the flushing property is improved, and the dispersibility and fluidity are also improved.

[0005]

However, in any case, the rosin amine-treated product has a drawback that the printed matter is remarkably bronzed, and an improvement has been demanded. And almost no literature. Therefore, the object of the present invention is useful for various coloring applications and, for example, when used in inks, especially lithographic inks, has excellent dispersibility, excellent fluidity, without impairing printability, and is non-bronze and glossy. It is to provide an azo lake pigment that gives an ink. As a result of intensive studies to achieve the above object, the present inventor has found that the object can be achieved by treating an azo lake pigment with an aliphatic primary amine as an amine.

[0006]

The above object is achieved by the present invention described below. That is, the present invention provides a method for producing an azo lake pigment characterized by adding an aliphatic primary amine to a diazo solution, an immersion liquid, or a dye or pigment slurry at the time of producing an azo lake pigment, and a first method obtained by this method. Azo lake pigment treated with a secondary amine.

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION Next, the present invention will be described in more detail with reference to embodiments of the present invention. The azo lake pigment in the present invention is a dye having a water-soluble group such as a sulfonic acid group and a carboxylic acid group, for example, barium, calcium, strontium, aluminum, manganese, nickel, and other polyvalent metal ions that have been made water-insoluble. For example, brilliant carmine 6B, permanent red 2
B, Lake Red C, Resol Red, Brilliant Scarlet G, Lake Red D, Bordeaux 10B, Orange II, Carmine 3B, Pigment Rubin G, Bon Maroon Museum, etc. Such azo lake pigments and the production method thereof are well known. The method for producing the pigment is not limited.

As the diazo component of these pigments, specifically, for example, 1-amino-4-methylbenzene-2
-Sulfonic acid, 1-amino-4-methyl-5-chlorobenzene-2-sulfonic acid, 1-amino-4-chloro-5
-Methylbenzene-2-sulfonic acid, 1-aminonaphthalene-2-sulfonic acid and the like.

In the present invention, these diazo components are diazotized by a conventional method, and the obtained diazotized product is coupled with a submersion solution such as β-naphthol or β-oxynaphthoic acid to synthesize a dye. Can be obtained with a metal or by adding the above-mentioned metal to a diazotizing solution in advance and performing lake formation simultaneously with coupling, followed by aging to obtain an azo lake pigment. At that time, in any one of the above-mentioned steps, that is, a treatment is performed by adding an aliphatic primary amine as a solution of an acidic salt to a diazo solution, a submerged solution, or a slurry of the obtained dye or pigment. Also, at an appropriate stage to the diazo solution, the immersion liquid, or the dye or pigment slurry during the production of the azo lake pigment of the present invention, a treating agent other than the aliphatic primary amine is added in an amount not to hinder the object of the present invention. The pigment can be further improved by the treatment.

The aliphatic primary amine used in the present invention is, for example, octylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, cocoalkylamine, tallowalkylamine, hardened tallowalkylamine, oleylamine, soybean alkyl Examples include amines and the like, all of which are industrially easily available and practical. Even if these aliphatic primary amines are used alone,
Two or more kinds may be used in combination. Moreover, you may use together with another processing agent.

The amount of the aliphatic primary amine used is 100
The range is preferably 0.1 to 10 parts by weight based on part by weight.
If the amount is less than 0.1 part by weight, the desired effect of the present invention will be insufficient, while if it exceeds 10 parts by weight, printability such as background smear will deteriorate, which is not preferable. A more preferred amount is in the range of 0.1 to 5 parts by weight.

[0012]

Next, the present invention will be described more specifically with reference to examples and comparative examples. In the following description, “parts” or “%” is based on weight unless otherwise specified.

Example 1 1-amino-4-methylbenzene-2-sulfonic acid 1
8.7 parts and 4.0 parts of sodium hydroxide are added to 360 parts of water and dissolved by stirring at room temperature. 35% hydrochloric acid 25 in this solution
Then, a solution of 6 parts of sodium sulfite dissolved in 20 parts of water is added at a stretch to diazotize the mixture, and the mixture is stirred at 5 to 8 ° C. for 30 minutes to obtain a diazo liquid. On the other hand, 17.9 parts of β-oxynaphthoic acid, 1.3 parts of naphthol AS, and 10.0 parts of sodium hydroxide were stirred and dissolved in 800 parts of water, and the amount of water was adjusted to 1000 parts and the temperature was adjusted to 10 ° C. Make it a pickling solution.

The diazo solution is added dropwise to the submerged solution over a period of 20 minutes, and a coupling reaction is performed to produce a dye, followed by stirring for 1 hour. Then, the pH was adjusted to 10 to 11, and rosin soap (4.7 parts of gum rosin (10% based on pigment))
And a solution prepared by dissolving 0.6 part of sodium hydroxide in 94 parts of water), and then 19 parts of calcium chloride (dihydrate) (1.3 mol per mol of dye) is added to form a lake. After stirring for 1 hour, the temperature was raised to 80 ° C., and a solution of Armin HT (manufactured by Lion Akzo) as an aliphatic primary amine (1.5 parts of Armin HT (3% based on pigment), 90% acetic acid 1.0%)
Of the resulting solution, and stirred for 10 minutes, and then filtered and washed with water to obtain a press cake. A part thereof was dried and pulverized to a powder to obtain an azo lake pigment composition of the present invention (dry yield: 48.5 parts).

EXAMPLE 2 The same amount of Armin 18 was used in place of Armin HT of Example 1.
An azo lake pigment was obtained in the same manner as in Example 1 except that D (manufactured by Lion Akzo) was used.

Example 3 Instead of the Armin HT of Example 1, the same amount of Armin 14 was used.
An azo lake pigment was obtained in the same manner as in Example 1 except that D (manufactured by Lion Akzo) was used.

Example 4 Instead of Armin HT of Example 1, the same amount of Armin 8D
An azo lake pigment was obtained in the same manner as in Example 1 except that (Lion Akzo) was used.

Comparative Example 1 An azo lake pigment was obtained in the same manner as in Example 1 except that the same amount of an aromatic primary amine, amine D (manufactured by Rika Hercules) was used instead of the armin HT of Example 1. Was.

Comparative Example 2 An azo lake pigment was obtained in the same manner as in Example 1 except that the armin HT of Example 1 was not used.

[Ink preparation and evaluation of powder pigment] 100 parts of each powder pigment obtained above and 400 parts of a lithographic ink varnish are premixed, and then the mixture is milled with a three-roll mill to prepare an ink. The ink was spread on a black belt-colored paper using a spatula, and the bronze of the coating film was visually observed. The bronze was evaluated as 5 and the bronze was significantly evaluated as 1. The dispersibility was measured using a grind gauge of 25 microns, and a scale was read where three continuous lines of 10 mm or more generated by the movement of the scraper appeared in one groove. This operation was repeated three times to find the median value. Five-step evaluation was performed with the median value of 5.0 microns or less as 5 and 25.0 microns or more as 1. Table 1 shows the above evaluation results.
Shown in

Table 1

[Inking and evaluation of press cake] 300 parts of a lithographic ink varnish was put into a test flasher, and each of the press cakes obtained above was used in an amount of 100% by weight of pigment.
And kneading at a temperature of 70 ° C. to remove primary separated water.
Furthermore, after removing the secondary separation water at 110 ° C. under reduced pressure, the varnish 1
Add 00 parts and remove from test flasher, 3
The ink is produced through this roll mill. Bronze and dispersibility were evaluated in the same manner as in the case of the powder pigment. Table 2 shows the evaluation results.

Table 2

[0024]

According to the azo lake pigment of the present invention obtained by treating an aliphatic primary amine, when used in a lithographic ink,
Compared to conventional azo lake pigments, it has excellent dispersibility and fluidity, and can provide a non-bronze glossy printed matter. Further, when the azo lake pigment of the present invention is used for a gravure ink, a non-bronze print having excellent dispersibility and viscosity suitability can be obtained, and the effect is not limited to a lithographic ink.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Katsumi Ogusu 1-7-6 Nihombashi Bakurocho, Chuo-ku, Tokyo Inside Dainichi Seika Kogyo Co., Ltd. (72) Inventor Toshitaka Terada 1-7 Nihonbashi Bakurocho, Chuo-ku, Tokyo No.6 Inside Dainichi Seika Industry Co., Ltd.

Claims (4)

[Claims] 1. A method for producing an azo lake pigment, which comprises adding an aliphatic primary amine to a diazo solution, a dip solution, or a dye or pigment slurry in the production of an azo lake pigment. 2. The amount of the aliphatic primary amine used is 100 pigments.
The method for producing an azo lake pigment according to claim 1, wherein the amount is 0.1 to 10 parts by weight based on part by weight. 3. The azo lake pigment is brilliant carmine 6.
The method for producing an azo lake pigment according to claim 1, which is B. 4. An aliphatic primary amine-treated azo lake pigment obtained by the method according to claim 1. Description: