JPS5910390B2 - 3,10-dialkoxy-6-halogeno-13-cyanotriphenodioxazine - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides 3,10-dialkoxy 6-halogenol 1
3-cyanotriphenodioxazine.

The following general formula [I] of the present invention ,.

α2. ■C°・1 ・ ・ ・ ・ (In the formula, R represents a lower alkyl group, and X represents a halogen atom.

The compound represented by ) is itself a novel compound and is valuable as a coloring agent for various fibers and synthetic resins.

To explain the present invention in detail, in the present compound represented by general formula [I], X includes a halogen atom such as a chlorine atom and a bromine atom, and R includes a methyl group, an ethyl group, and a propyl group. , a lower alkyl group such as a butyl group.

The compound of the present invention is produced, for example, according to the following method. That is, the following general formula [old, α:.

■C°・1... (wherein, R and X have the same meanings as in the above general formula [I].

) is reacted with a metal cyanide in an organic medium, followed by separation and purification.

More specifically, the compound of the present invention is produced as follows.

That is, a compound represented by the general formula [formula] is dissolved or suspended in a solvent together with a metal cyanide, particularly cuprous cyanide or a compound producing it, and heated. Progress of the reaction can be monitored by thin layer chromatography. After the reaction is complete, the reaction product is precipitated, for example by adding water. Excess metal cyanide or metal halide, such as cuprous cyanide, can be converted into a water-soluble metal salt using ammonium cyanide or an alkali metal, or the cuprous salt can be converted into a water-soluble metal salt, such as cuprous chloride, according to known methods. After oxidation to a water-soluble cupric salt with diiron, it can be removed by P filtration. Since the reaction product obtained generally contains side reaction products, in order to obtain the desired compound, they must be treated by, for example,
It is necessary to separate and purify by column chromatography or thin layer chromatography.

Suitable solvents for the cyanation reaction include, in particular, polar aprotic solvents such as dimethylformamide, N-methylpyrrolidone, formamide, dimethylacetamide, pyridine, quinoline, acetonitrile, benzonitrile, monotris-dimethylamide phosphate, dimethylsulfoxide, etc. is suitable.

Particularly preferred solvents are dimethylformamide, N-methylpyrrolidone. Suitable metal cyanides include cuprous cyanide, silver cyanide, lead cyanide, potassium ferrocyanide, calcium ferrocyanide, copper ferrocyanide, and zinc cyanide.

Among these, cuprous cyanide is particularly superior due to its high reactivity. This can be used as it is in the reaction, but it may also be produced in a reaction medium, for example by adding an alkali cyanide and a suitable cupric salt to the reaction medium.
For example, cupric sulfate or cupric acetate may be added. In the reaction, the reaction temperature can vary within a wide range, but depends on the organic solvent and especially on the structure of the starting compound of the general formula [].

Generally the temperature is 20-220°C, preferably 130-220°C
The temperature is 10°C. The compound of the present invention is itself a novel dioxazine dye, has excellent affinity for polyethylene terephthalate and cellulose acetate, and produces dyed products with bright reddish-yellow to bluish-red tones with excellent light resistance. give.

Furthermore, since it has excellent heat resistance, it is suitable for coloring synthetic resins such as polystyrene, ABS, polyvinyl chloride, polymethacrylate, etc., and is also suitable for coloring polyethylene terephthalate and polyamide with a stock solution.

Production examples of the compounds of the present invention and properties of the compounds are specifically shown below.

Example 1 Compound 5.09 represented by the following structural formula and cuprous cyanide 109
was added to 100 fnt of N-methylpyrrolidone, and the mixture was reacted under reflux for 5 hours.

After cooling, the mixture was poured into water, and the separated cake was mixed with 10 g of ferric chloride and 30 ml of concentrated hydrochloric acid. was stirred at 60° C. for 1 hour in a solution of 180 μl of water. After cooling, pass through suction P,
The resulting cake was washed with water and dried. The dried cake was dissolved in chloroform and separated and purified by thin layer chromatography to obtain a compound represented by the following structural formula (1). The molecular weight of compound (1) determined by elemental analysis and mass spectrometry (mass spectrometry (c)) is as follows, which agrees well with the calculated value. Structural formulas (2), (3), (
The compound represented by 4) was also obtained by the same method as compound (1).

The molecular weight and elemental analysis values determined by mass spectrometry (mass spectrum) for each were as follows, and agreed well with the calculated values.
In addition, maximum absorption wavelength λMax (chloroform) of compounds represented by structural formulas (1), (2), (3) and (4)
are shown in Table 1. Example of use: Dye represented by the following structural formula 0.59, naphthalene sulfonic acid formaldehyde condensate 19 and higher alcohol sulfate ester 2f! A dye bath was prepared by dispersing it in water 31 containing the following.

Polyester fiber 1009 was immersed in this dye bath, and 130
After dyeing at .degree. C. for 60 minutes, soaping, washing with water, and drying were performed, a bright red polyester fiber dyeing with good light fastness and sublimation fastness was obtained. By dyeing polyester fibers using the compounds of structural formulas (2), (3), and (4) in the same manner as above, a bright red dyed product with good light fastness and sublimation fastness can be obtained. Ta.

Claims (1)

[Claims] 1 The following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, R represents a methyl group or an ethyl group, and X represents a chlorine atom or a bromine atom. ) 3,10-dialkoxy-6-halogeno-13-cyanotriphenodioxazine.