JPS5941466B2 - Manufacturing method of azamethine dye - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a novel azamethine dye.

Specifically, the present invention relates to the following general formula [wherein R1 represents a hydrogen atom or a lower alkyl, aryl, aralkyl or alkenyl group which may be substituted with a hydroxyl group, a cyano group and/or an alkoxy group] , R2 represents a hydrogen atom, a halogen atom, a nitro group or a lower alkyl group, R3 represents a hydrogen atom,
Halogen atom, cyano group, nitro group, lower alkyl group,
Represents a lower alkoxy group, an alkylthio group, or a dialkyl-substituted amino group.

] and 2-amino-4,5-dicyanoimidazole represented by the structural formula are heated and condensed in the presence of a condensing agent in an inert organic solvent to form the following general formula (1) [wherein Rl , R2 and R3 are the same as defined above], and if necessary, the compound represented by the general formula (9) is alkylated using an alkylating agent. Formula [wherein Rl, R2 and R3 are the same as defined above, R4
represents hydrogen or a lower alkyl group.

This invention relates to a method for producing a novel azamethine dye represented by the following. The present invention will be explained in more detail.

Naphtholactams, which are one of the raw materials, are represented by the general formula [1], where R1 is a hydrogen atom; a lower alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, or a hydroxyethyl group. Hydroxy-substituted lower alkyl groups such as , hydroxypropyl group, hydroxyisopropyl group; Lower alkoxy-substituted lower alkyl groups such as methoxyethyl group, ethoxyethyl group, propoxyethyl group, methoxypropyl group, propoxypropyl group; Cyano-substitution such as cyanoethyl group lower alkyl group; phenyl group;
Substituted phenyl groups such as tolyl group, 0-methoxyphenyl group, p-methoxyphenyl group, p-ethoxyphenyl group, p-nitrophenyl group, p-chlorophenyl group; Naphthyl group such as 1-naphthyl group and 2-naphthyl group Aryl groups such as benzyl group, p-chlorobenzyl group, p-bromobenzyl group, p-nitrobenzyl group, phenethyl group, and vinyl group, propenyl group, isopropenyl group, 1-butenyl group, crotyl group Examples include lower alkenyl groups such as groups.

In addition, examples of R2 include a hydrogen atom; lower alkyl groups such as a methyl group, ethyl group, and propyl group; halogen atoms such as a chlorine atom and a bromine atom, and a nitro group, and examples of R3 include a hydrogen atom; a methyl group, an ethyl group, Lower alkyl groups such as propyl groups; halogen atoms such as chlorine and bromine atoms; cyano groups; nitro groups; lower alkoxy groups such as methoxy and ethoxy groups; phenoxy groups; lower alkyl-substituted thio groups such as methylthio and ethylthio groups and dimethylamino group,
Examples include di-lower alkyl-substituted amino groups such as diethylamino group.

Examples of inert organic solvents used in condensing the naphtholactams represented by the general formula [1] with 2-amino-4,5-dicyanoimidazole include benzene, toluene, xylene, monochlorobenzene, dichlorobenzene, trichlorobenzene, Examples of the condensing agent include nitrobenzene and nitrotoluene, and examples of the condensing agent include phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, and thionyl chloride.

The condensation reaction temperature is usually 80°C to 200°C, preferably 1
Conditions between 000C and 130C are advantageous. Furthermore, as alkylating agents used in the alkylation reaction after condensation,
Examples include alkyl halides having 1 to 4 carbon atoms such as methyl iodide and ethyl bromide, and alkyl sulfates such as dimethyl sulfate and diethyl sulfate.

Examples of the solvent include polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, dioxane, and cellosolves, and in some cases, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, and sodium are used as reaction catalysts. An alkali such as Alcolade may also be used. In addition, the reaction temperature in the alkylation reaction is 50 to 1
A temperature of 50°C, preferably around 100°C is employed. The new azamethine dye obtained by the method of the present invention has excellent dyeing properties for polyester fibers and cellulose ester fibers, and the dyed products thereof have a bright yellow tone and have extremely good light fastness.

EXAMPLES Next, the present invention will be specifically explained using examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof.

Example 1 1 naphtholactam in 15.0 ml of monochlorobenzene
．． 699 and 1.199% of 2-amino-4,5-dicyanoimidazole were added and the temperature was raised to 100°C, and then 1.999% of phosphorus oxychloride purified by distillation was gradually added dropwise.
After incubating at 0°C±5°C for 2 hours, it was allowed to cool to room temperature.

Next, 10.0 ml of methanol was added, stirred for 1 hour, allowed to cool, filtered, washed with methanol, and dried to obtain a novel yellow compound represented by the following structural formula.

Elemental analysis results: This compound dyes polyester fibers in a greenish-yellow color with good fastness properties.

Example 2 Monochlorobenzene 15.0ml!4:]N-Ethyl-
Naphtholactam 1.979 and 2-amino-4,5 dicyanoimidazole 1.19f! was added and the temperature was raised to 100°C, 1.999% of phosphorus oxychloride purified by distillation was gradually added dropwise, kept at 100°C ± 5°C for 2 hours, and then allowed to cool to room temperature.

Next, 10.0 ml of methanol was added, stirred for 1 hour, allowed to cool, filtered, washed with methanol, and dried to obtain a novel yellow compound represented by the following structural formula. Elemental analysis results: This compound dyes polyester fibers in a greenish-yellow color with good fastness properties.

Example 3 2.229 N-cyanoethyl-naphtholactam and 2-amino-4,5-in 15.0 ml of monochlorobenzene
After adding 1.199% of dicyanoimidazole and raising the temperature to 100°C, 1.999% of phosphorus oxychloride purified by distillation was gradually added dropwise, kept at 100°C±5°C for 2 hours, and then allowed to cool to room temperature.

Next, 10.0 ml of methanol was added, stirred for 1 hour, filtered with F, washed with methanol, and dried to obtain a novel yellow compound represented by the following structural formula. Elemental analysis results ノ\ii - Moon Vh4ν υ!
V-V94 - This compound dyes polyester fibers in a greenish yellow color with good fastness properties.

Example 4 In 30.0 ml of dioxane, 3.129 of the compound represented by the following structural formula obtained in Example 2, 1.85 of diethyl sulfate
9 and 0.79 sodium methylate were added thereto, and the mixture was stirred at 100° C. for 3 hours, then allowed to cool to room temperature and discharged into 200 ml of water.

The mixture was then stirred at room temperature for 1 hour and then filtered to obtain a novel yellow compound represented by the following structural formula. Elemental analysis results: This compound dyes polyester fibers in a greenish-yellow color with good fastness properties.

Example 5 In 30.0 ml of dioxane, 2.849 of the compound represented by the following structural formula obtained in Example 1, 3.70 of diethyl sulfate
9 and sodium methylate 1.409 were added and heated to 100°C.
After stirring for 3 hours, the mixture was allowed to cool to room temperature and discharged into 200 ml of water.

Then, the mixture was stirred at room temperature for 1 hour, filtered, and dried to obtain the same compound as in Example 4. Examples 6-23 In Examples 6-8, 10, 12-15, 21 and 22, the same method as Examples 1-3 was carried out, and Examples 9, 1
In Examples 1, 16 to 20 and 23, compounds represented by the following general formula were obtained in the same manner as in Example 4.

Table 1 shows the types of substituents of the obtained compound and the color tone on the polyester.

Claims (1)

[Claims] 1 The following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] [In the formula, R
^1 represents a hydrogen atom, or a lower alkyl, aryl, aralkyl or alkenyl group which may be substituted with a hydroxyl group, a cyano group and/or an alkoxy group, and R^2 represents a hydrogen atom, a halogen atom, a nitro or a lower alkyl group, and R^3 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a lower alkyl group, a lower alkoxy group, an alkylthio group, or a dialkyl-substituted amino group. ] and 2-amino-4,
5-Dicyanoimidazole is heated and condensed to form the following general formula [II] ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [II] [In the formula, R^1, R^2 and R^3 are the same as the above definitions. ] The following general formula [III] is characterized in that the compound represented by the above general formula [II] is alkylated using an alkylating agent.
▲There are mathematical formulas, chemical formulas, tables, etc.▼ [III] [In the formula, R
^1, R^2 and R^3 are the same as defined above, and R
^4 represents a hydrogen atom or a lower alkyl group. ] A method for producing an azamethine dye represented by