JPH0619050B2 - Dispersion method of perylene and perinone pigments - Google Patents

Description

The present invention relates to a method for dispersing a perylene or perinone pigment in a non-aqueous vehicle.

"Prior art" Generally, pigments have various properties such as a decrease in fluidity due to aggregation caused when dispersed in a vehicle of a paint or an ink, a color separation when mixed with other pigments, or a decrease in coating gloss. It often causes the undesirable phenomenon of.

As a method of improving such a defect of the pigment, a method of treating the surface of the pigment with a surfactant, a metal soap, various resins and the like, and use of various derivatives of organic pigments have been proposed. However, no deep research has been conducted on perylene and perinone pigments, and the effect of imparting non-aggregating properties, in particular, the vividness and color developability of metallic paints, has not been sufficiently satisfactory. It is the actual situation.

"Problems to be Solved by the Invention" The present invention provides a method of dispersing a pigment, which has not been known so far, which gives a remarkable effect of improving the fluidity and cohesiveness of a perylene or perinone pigment in a non-aqueous vehicle. It is an object of the present invention to provide a dispersion method which has an excellent effect on the sharpness and color development of a metallic paint.

"Means for Solving Problems" The present invention is intended to solve the above problems, and 0.5 to 10 parts by weight of a compound represented by the following general formula [I] is added to 100 parts by weight of a perylene or perinone pigment. A method for dispersing perylene or perinone pigment in a non-aqueous vehicle, which is characterized in that it is used.

General formula [I] In the formula, Q represents a naphthalene ring or a perylene ring adjacent to four carbonyl groups at the peri position, and R ¹ and R ² are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms.

n is an integer of 1 to 3 and p is 2.

By using the compound (modifier) represented by the general formula [I] in combination with perylene or perinone type pigment, the above problems can be improved, a remarkable effect can be confirmed, and the modifier itself can be prepared. The present invention has been completed by confirming that it is practically advantageous in terms of easiness.

"Function" The compound represented by the general formula [I] of the present invention can be obtained by a simple reaction between an anhydride of a peri-substituted tetracarboxylic acid of naphthalene or perylene and an amine component.

Typical amine components include dimethylaminoethylamine, diethylaminoethylamine, dimethylaminopropylamine, diethylaminopropylamine,
Examples include methylaminopropylamine, ethylaminoethylamine, dibutylaminopropylamine, and the like.

To prepare the compound of the general formula [I] of the present invention, for example, the above aromatic carboxylic acid anhydride and amine are reacted in an organic solvent at 100 ° C. or higher for several hours, the solvent is removed by distillation, and water is added. It can be obtained by filtration, washing with water, drying and crushing. In some cases, the desired compound (modifier) can be easily obtained by reacting in an aqueous medium at 70 to 90 ° C. for several hours.

0.5 to 100 parts by weight of the organic pigment, particularly perylene or perinone-based pigment, of the compound (modifier) represented by the formula [I]
The use of 10 parts by weight, preferably 1 to 4 parts by weight, provides excellent effects in improving fluidity and preventing cohesion in a non-aqueous vehicle. In order to disperse the perylene and perinone pigments using the modifier of the present invention, it is common to use the modifier and the pigment in powder blending, but they may be added to the non-aqueous vehicle together with the pigment. . It is also possible to mix and use the pigment in advance when preparing the pigment itself. The desired effects can be obtained by any of the above methods.

Examples of the perylene and perinone pigments used in the present invention include C.I. I. Pigment red 123, C.I. I.
Pigment red 149, C.I. I. Pigment Red 1
78, C.I. I. Pigment red 179, C.I. I. Pigment red 189, C.I. I. Pigment Red 19
0, C.I. I. Pigment Red 224, C.I. I. Pigment Violet 29, C.I. I. Pigment Orange 4
3 and the like.

Next, examples will be given and the effects thereof will be described. Parts and percentages in the examples are shown by weight.

"Examples and Comparative Examples" Example 1 12 parts of 3,4,9,10 perylenetetracarboxylic dianhydride and 16 parts of diethylaminopropylamine were added to 200 parts of ortho-dichlorobenzene and stirred at 120 ° C for 3 hours. . After removing ortho-dichlorobenzene by distillation under reduced pressure, water was added to it, washed with water, dried, and pulverized to yield 1.
2.6 parts of compound formula [II] are obtained.

Example 1-a 0.3 part of the compound of the above formula [II] was used as C.I. I. Pigment Red 179 (10 parts) to give a uniform mixture. This was applied to C. varnish for baking acrylic / melamine paint. I. Pigment Red 179 was added so as to be 8.3% and dispersed by a sand mill, and the prepared primary color paint had good fluidity, and the coating film showed clear and good gloss. Further, even in a colored metallic paint prepared by mixing an aluminum paint base prepared with the above varnish with a pigment and an aluminum ratio of 3/1, 1/1, 1/3, 1/9, extremely vivid coloring property is obtained. A good coating film was obtained.

Comparative Example 1-b The paint obtained by directly carrying out Example 1-a except for adding the compound of the formula [II] in Example 1-a had poor fluidity and the coating film was poor in gloss and was not clear. Atsuta Further, even in the case of a colored metallic paint, the coating film was unclear and the color development was poor.

Example 2 8 parts of naphthalene 1,4,5,8 tetracarboxylic dianhydride and 12 of dimethylaminopyropyramine in 50 parts of water
Parts, and stirred at 80 ° C. for 1 hour. It is filtered, washed with water and dried to obtain a powdery compound formula [III] with a yield of 11.9 parts.

Example 2-a 0.2 part of the compound of the above formula [III] and C.I. I. The primary color paint obtained in the same manner as in Example 1-a except that 10 parts of Pigment Red 123 was simultaneously added to the same coating varnish as in Example 1 had good fluidity, and the coating film showed clear and good gloss. It was Further, the colored metallic paint formed an extremely clear coating film having good color development.

Comparative Example 2-b The coating material obtained by directly carrying out Example 2-a except that the compound of the formula [III] in Example 2-a was added was the same as Comparative Example 1-b in fluidity, gloss and vividness. And the color development was poor.

Example 3 16 parts of 3,4,9,10 perylenetetracarboxylic dianhydride and 20 of methylaminoethylamine in 100 parts of water
Parts, and stirred at 85 ° C. for 3 hours. It is filtered, washed with water, dried and pulverized to obtain a compound of formula [IV] in a yield of 19.1 parts.

C. in Example 1-a and Comparative Example 1-b. I. Pigment Red 179 in place of the mixture of the compound of the formula [II], 2 wt% of the compound of the formula [IV] was added during the preparation of the pigment itself. I. Pigment Violet 29 or C.I. I. Pigment Orange 43, Example 1-
a, Comparative Example 1-b were carried out as they are
Which is quite similar to the improving effect in the formula [IV] of the present invention.
It was judged that the dispersion method using the compound of 1) is extremely useful.

"Effects of the Invention" The method for dispersing perylene and perinone-based pigments in the present invention exerts a remarkable improvement effect which is not seen by using perylene or perinone-based pigments singly for a non-aqueous vehicle, particularly a baking type varnish for metallic However, the clear and good color-developing coating film with the colored metallic paint was completely satisfactory. Further, it was confirmed that the method is very advantageous in practical use because of the ease of preparation of the modifier itself.

Claims (1)

[Claims] 1. A non-aqueous vehicle for a perylene or perinone pigment, characterized in that 0.5 to 10 parts by weight of a compound represented by the following general formula [I] is used in 100 parts by weight of a perylene or perinone pigment. Distribution method. General formula [I] In the formula, Q represents a naphthalene ring or a perylene ring adjacent to four carbonyl groups at the peri position, and R ¹ and R ² are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. n is an integer of 1 to 3 and p is 2.