JPH0737584B2 - Dye compounds and coloring materials for resins - Google Patents

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel dye compound and a coloring material for resins. More specifically, the present invention relates to a novel triazine compound used as a pigment and a coloring material for a thermoplastic resin for preliminarily coloring the thermoplastic resin of the fiber raw material and performing injection molding or the like.

[0002]

2. Description of the Related Art Colorants for resins are required to have good dispersibility, solubility, heat resistance and sublimation resistance with respect to resins, and chemical resistance as other properties. As for the color tone, clearness of color tone, light resistance, chemical resistance, migration resistance or good non-bleeding property is required.

[0003]

The present invention has excellent transparency when used for coloring a novel dye compound and resin,
The purpose of the present invention is to provide a coloring material that produces clear color.

[0004]

The present invention has the following general formula [1].

[0005]

[Chemical 3]

(Wherein, X ¹ and X ² represent a hydrogen atom or a halogen atom, X represents an oxygen atom or --NH--, R ¹ and R ² represent --NR ³ R ⁴ , and R ³
And R ⁴ represents a hydrogen atom, an unsubstituted alkyl group or an alkoxyalkyl group. ) And a coloring material for resin represented by the above general formula.

In the present invention, the unsubstituted alkyl group represented by R ³ and R ⁴ is a methyl group, an ethyl group,
A linear or branched propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group and the like can be mentioned. The alkoxy group of the alkoxyalkyl group is a C ₁ -C ₃ straight chain. Alternatively, a branched alkoxy group can be used.

The compound represented by the above general formula [1] used in the present invention can be produced by the following method.
That is, the following general formula [2]

[0009]

[Chemical 4]

A dye represented by the formula (wherein X ¹ , X ² and X are the same as defined above) is dissolved in an organic solvent such as N-methylpyrrolidone to give trichlorotriazine or trifluorotriazine and triethylamine and the like. Intermediate of the general formula [3] obtained by reacting at a temperature of 0 ° C. to 20 ° C. in the presence of a deoxidizing agent

[0011]

[Chemical 5]

(Wherein X ¹ , X ² , and X are the same as defined above, Z and Z ¹ are chlorine or fluorine atoms) are not taken out as they are, and are represented by the general formulas [4] and [5]. Represented amines or alcohols R ¹ H ··· [4] R ² H ··· [5] (wherein R ¹ and R ² are the same as defined above), triethylamine, etc. It can be produced by sequentially reacting the deoxidizing agent of the present invention at 60 to 100 ° C.

When the compound of the present invention is used as a coloring material for resins, the resin is polystyrene, polymethylmethacrylate, polyvinyl chloride, acrylonitrile / butadiene / styrene copolymer (ABS resin), acrylonitrile / styrene copolymer. Thermoplastic resins such as (AS resin), polyester, polycarbonate, polyphenylene oxide, polystyrene, polypropylene, polyethylene, polyacrylonitrile, and polyamide can be used.

[0014]

The colorant of the present invention can be obtained by mixing the resin and the colorant by an appropriate method and applying heat and pressure to obtain a colored product by a method such as injection molding, extrusion, spinning or the like.
In addition, the coloring material of the present invention has excellent solubility in the above resin, and particularly excellent migration resistance.
There is no contamination of the molding machine during the molding operation at 00 ° C. Further, the obtained colored molded product has a transparent orange hue and is excellent in light resistance, heat resistance and chemical resistance.

The resin can be colored by a known method. For example, resin pellets or powders are mixed in a suitable mixer with a ground colorant and optionally various additives, and then an extruder, Color molding can be performed with a processing machine such as an injection molding machine or a roll mill. It is also possible to add a colorant to a monomer containing an appropriate polymerization catalyst to form a desired thermoplastic resin by polymerization and mold it by an appropriate method. The colorant is used in an amount of 0.01 to 5% by weight, preferably 0.01 to 1% by weight, based on the resin. It is also possible to obtain an opaque colored product by using titanium dioxide in an amount of 0.1 to 1% by weight.

Next, the method of the present invention will be specifically described with reference to examples, but the present invention is not limited to the following examples.

[0017]

【Example】

Examples 1 to 7 0.1 g of the coloring material shown in Table 1 was used as a polyester resin 100.
g and homogenized at 280 ° C. using an extruder to give colored pellets. The colored pellets are 30
Molding was carried out under the conditions of 0 ° C. × 2 minutes to obtain a polyester colored molded product (plate). The obtained molded product was transparent and had a bright orange color, and was excellent in light resistance and blade resistance.

Test Method for Bleed Resistance The polyester colored molded articles (plates) produced in the above-mentioned examples were dry-cleaned, and the degree of contamination of the residual liquid was evaluated by a contamination gray scale. The compound of Example 1 was synthesized as follows. The following structural formula

[0019]

[Chemical 6]

2.9 g (0.01 mol) of the compound represented by the above is dissolved in 30 ml of N-methylpyrrolidone, and 2.0 g of cyanuric chloride is added at a temperature of 30 ° C. to 35 ° C. over 30 minutes. Stir for 1 hour at the same temperature and add 1.1 g of triethylamine. Then, 1.5 g (0.02 mol) of N, N-diethylamine and 1.1 of triethylamine.
g of mixed solution is added over 30 minutes at 50-60 ° C. Then, the temperature is raised to 80 ° C., 1.8 g of 28% ammonia water is added, and the mixture is stirred at the same temperature for 1 hour. After cooling
The obtained precipitate was filtered off to obtain a dry cake.

[0021]

[Table 1]

Example 8 The following structural formula

[0023]

[Chemical 7]

0.1 g of the coloring agent represented by and 0.5 g of titanium dioxide were mixed with 100 g of a polycarbonate of 2,2-bis (4-hydroxyphenyl) propane and homogenized at 280 ° C. using an extruder to give colored pellets. Got The colored pellets were molded by an injection molding machine at 300 ° C to obtain a molded product. The obtained molded product was opaque due to titanium dioxide, but exhibited a good orange color and was excellent in light resistance. The coloring material used in this example was synthesized according to the method described in Example 1. Λmax (acetone) of this product is 485 nm
Met.

[0025]

EFFECT OF THE INVENTION The compound of the present invention is a useful transparent orange colorant compound, and is particularly excellent in light resistance, heat resistance and chemical resistance, and provides a colored resin product having good bleed resistance. be able to. In addition, the migration property is excellent, and the obtained colored resin is characterized by less pollution of the resin molding machine.

Claims (2)

[Claims] 1. The following general formula [1]: (In the formula, X ¹ and X ² represent a hydrogen atom or a halogen atom, X represents an oxygen atom or —NH—, and R ¹
And R ² represent —NR ³ R ⁴ , and R ³ and R ⁴ represent a hydrogen atom, an unsubstituted alkyl group or an alkoxyalkyl group. ) A dye compound represented by. 2. The following general formula [1]: (In the formula, X ¹ and X ² represent a hydrogen atom or a halogen atom, X represents an oxygen atom or —NH—, and R ¹
And R ² represent —NR ³ R ⁴ , and R ³ and R ⁴ represent a hydrogen atom, an unsubstituted alkyl group or an alkoxyalkyl group. ) A coloring material for resin represented by.