JPH0217589B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to disazo dyes, and more specifically, it dyes polyester fibers blue and examines various fastnesses, particularly light fastness, sublimation fastness, water fastness,
In addition, it has excellent temperature stability and PH stability during dyeing, and as a reactive dye, it can dye natural fibers such as cotton, wool, and silk blue, and has excellent color fastness, especially light fastness and washing fastness. It concerns dyes. The disazo dye of the present invention has the following general formula [] (In the formula, X represents a cyano group, a lower alkoxycarbonyl group, or a lower alkylsulfonyl group, Y represents a hydrogen atom, a chlorine atom, a methyl group, or an acylamino group, and Z represents a hydrogen atom, a chlorine atom, or a methyl group. , R ¹ and R ² are hydrogen atoms, cyano groups, hydroxyl groups, sulfonic acid groups,
Lower alkoxy group, lower alkoxy lower alkoxy group, lower alkoxycarbonyl group, lower alkoxycarbonyloxy group, lower alkylcarbonyloxy group, lower alkyl group optionally substituted with benzyloxycarbonyl group or phenyl group, cyclohexyl group, alkenyl group Or represents an aryl group. This is a disazo dye shown in In the above general formula [], examples of the alkoxycarbonyl group represented by Examples of the acylamino group represented by Y include an acetylamino group, a chloroacetylamino group, a benzoylamino group, a methylsulfonylamino group, a chloropropionylamino group, an ethoxycarbonylamino group, and an ethylaminocarbonylamino group. R ¹ and
Examples of the unsubstituted alkyl group represented by R ² include a methyl group, an ethyl group, a linear or branched propyl group, a butyl group, a bentyl group, a hexyl group, a heptyl group, an octyl group, and substituted alkyl groups. As a group, lower alkoxyalkyl groups such as methoxyethyl group, ethoxyethyl group, butoxyethyl group; lower alkoxy lower alkoxy lower alkyl groups such as methoxyethoxyethyl group, ethoxyethoxyethyl group; hydroxyethyl group, hydroxypropyl group, hydroxybutyl group. , hydroxyalkyl groups such as hydroxyhexyl groups; cyano-lower alkyl groups such as cyanomethyl and cyanoethyl groups; sulfo-lower alkyl groups such as sulfomethyl groups;
Lower alkylcarbonyloxy lower alkyl groups such as acetyloxyethyl group; Lower alkoxycarbonyloxy lower alkyl groups such as methoxycarbonyloxyethyl group; Lower alkoxycarbonyl lower alkyl groups such as methoxycarbonylmethyl group and ethoxycarbonylmethyl group; benzyloxycarbonyl Examples include benzyloxycarbonyl lower alkyl groups such as a methyl group; phenyl-substituted lower alkyl groups such as a benzyl group and a phenethyl group; examples of the aryl group include a phenyl group, a chlorophenyl group, and a methylphenyl group. The disazo dye represented by the above general formula [] is the following formula [] Diazotize the amines represented by the following formula [] (In the formula, X is the same as defined above.) The following formula obtained by coupling with aminothiophenes [] (wherein, X is the same as defined above) is diazotized to form the following general formula [V] (In the formula, Y, Z, R ¹ and R ² are the same as defined above.) It can be produced by coupling with an aniline represented by the following formula. Fibers that can be dyed with the disazo dye of the present invention include polyester fibers made of polyethylene terephthalate, polycondensates of terephthalic acid and 1,4-bis-(hydroxymethyl)cyclohexane, cellulose fibers such as cotton and hemp, Examples include nitrogen-containing fibers such as silk and wool, and blended and woven products of the above-mentioned natural fibers and polyester fibers. In order to dye polyester fibers using the dye of the present invention, since the dye represented by the general formula [] is water-soluble, a dye bath or printing paste is prepared by dissolving it in an aqueous medium, and dyeing or All you have to do is print. For example, when dyeing polyester fibers, add acidic substances such as formic acid, acetic acid, phosphoric acid, or ammonium sulfate to the dyeing bath.
7. Dyeing with excellent fastness can be achieved by dyeing at a temperature of 120°C to 200°C. When dyeing natural fibers using reactive dyes, alkaline substances such as soda carbonate, sodium silicate, caustic soda, or bicarbonate of soda are added to the dyeing bath.
9 to 13, dyeing with excellent fastness can be achieved by dyeing at a temperature of 30°C to 80°C. Furthermore, the dye represented by the general formula [] used in the method of the present invention may be used in combination with dyes of the same type or dyes of other systems, and among these, the dyes represented by the general formula [] can be used in combination with each other. Depending on the combination, good results such as improved dyeability may be obtained. Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Example 1 Structural formula below A dye bath was prepared by dissolving 0.5 g of the dye shown in 3 liters of water. 100g of polyester fiber in this dyeing bath
After soaking and dyeing at 130°C for 60 minutes, soaping, washing with water and drying, a vivid blue dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced as follows. 26.7 g of p-(sulfoxyethylsulfonyl)aniline was dissolved in 150 ml of 4% hydrochloric acid, the solution was cooled to 2°C, and then 50 ml of 2N sodium nitrite was added. At this time, the temperature was set not to exceed 5°C. The obtained diazonium salt solution was mixed with 12.4 g of 2-amino-3-cyanothiophene and 124 g of methanol.
ml of the solution at 2°C and stirred at the same temperature for 2 hours. The precipitated monoazo compound was removed, washed with brine, and dried. 15.0 g of this monoazo compound [2-amino-3-cyano-5-(p-sulfoxyethylsulfonylphenylazo)thiophene] was added to a mixture of 150 ml of acetic acid and 150 ml of phosphoric acid; Nitrosyl sulfuric acid (3.5 g of sodium nitrite to 20 g of 97% sulfuric acid)
(prepared by dissolving the monoazo compound) was gradually added thereto and stirred at the same temperature for 30 minutes to prepare a diazo solution of the monoazo compound.
N-(ethyl)-N-(β-acetoxyethyl)
Dissolve 10.5 g of aniline in 200 ml of methanol and place on ice.
200g and 100ml of water. The diazo solution prepared above was added thereto, stirred at 0 to 5°C for 2 hours, and then adjusted to pH 5 using 25% caustic soda. The precipitated disazo dye was removed, washed with brine, and dried. This product's λ _nax (80% acetone aqueous solution) is
It was 640nm. Example 2 Structural formula below A dye bath was prepared by dissolving 0.5 g of the dye shown in 3 liters of water. 100g of polyester fiber in this dyeing bath
After soaking and dyeing at 130°C for 60 minutes, soaping, washing with water and drying, a vivid blue dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced according to Example 1. This product's λ _nax (80% acetone aqueous solution) is
It was 665nm. Example 3 Structural formula below A dye bath was prepared by dissolving 0.5 g of the dye shown in 3 liters of water. 100g of polyester fiber in this dyeing bath
After soaking and dyeing at 130°C for 60 minutes, soaping, washing with water and drying, a vivid blue dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced according to Example 1. This product's λ _nax (80% acetone aqueous solution) is
It was 630nm. Example 4 Structural formula below A dyeing bath was prepared by dispersing 0.5 g of the dye shown in 3 liters of water. 100g of cotton broadcloth in this dyeing bath
After soaking and dyeing at 40°C for 60 minutes, soaping, washing with water and drying, a vivid blue dyed fabric was obtained. The light fastness and washing fastness of the obtained dyed fabric as well as the temperature stability and PH stability during dyeing of the above dye were good. The dye used in this example was produced according to Example 1. This product's λ _nax (80% acetone aqueous solution) is
It was 615nm. Examples 5-26 Polyester fibers or natural fibers (cotton broadcloth, Examples 8, 9, 24-26) were dyed using the dyes shown in Table 1 below in the same manner as in Example 1, and the dyes shown in the table were dyed. A colored dyed product was obtained.

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【table】

Claims (1)

[Claims] 1. General formula (In the formula, X represents a cyano group, a lower alkoxycarbonyl group, or a lower alkylsulfonyl group, Y represents a hydrogen atom, a chlorine atom, a methyl group, or an acylamino group, and Z represents a hydrogen atom, a chlorine atom, or a methyl group. R ¹ and R ² are a hydrogen atom, a cyano group, a hydroxy group, a sulfo group, a lower alkoxy group, a lower alkoxy lower alkoxy group,
Represents a lower alkyl group, a cyclohexyl group, an alkenyl group, or an aryl group which may be substituted with a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy group, a lower alkylcarbonyloxy group, a benzyloxycarbonyl group, or a phenyl group. ) Disazo dyes.