JPS6012473B2 - How to dye polyester fiber - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for dyeing polyester fibers, and more specifically, the present invention relates to a dispersed monoazo dye with a high dye density that dyes polyester fibers in a strong and vivid red color. .

The following general formula (wherein R2 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an aralkyl group, or an aryl group, and R3, R4, R5, and R6 each represent a hydrogen atom, a nitro group, a carboxy group, Indicates a halogen atom, substituted or unsubstituted alkyl group, aryl group, alkoxy group, aryloxy group, alkoxycarbonyl group, acyl group, acylamino group, alkylsulfonyl group, arylsulfonyl group, aminosulfonyl group, and aminocarbonyl group.

It is well known (Japanese Patent Publication No. 49-121270) that the azo dye represented by As a result of careful consideration, the general formula [1
] (In the formula, RI represents a hydrogen atom or an acyl group.

It has been found that if polyester fibers are dyed using the new azo dye represented by , and arrived at the present invention. To explain the present invention in detail, in the above general formula [1], RI includes not only a hydrogen atom but also an acyl group such as an acetyl group, a propionyl group, an n-butyryl group, an isoptyryl group, an n-valeryl group, an isovaleryl group, etc. Can be mentioned.

The dye represented by the general formula [1] used in the present invention can be produced, for example, by the following method.

2-Methyl-4nitroaniline is diazotized by a conventional method and coupled with 4-hydroxynaphthalic acid-N-(2'-hydroxyethoxyethyl)-imide represented by the following structural formula, optionally further obtained. It can be produced by treating an azo dye represented by the following structural formula with an acylating agent such as acid chloride or acid anhydride.

Fibers that can be applied in the present invention include polyester fibers made of polyethylene terephthalate, polycondensates of terephthalic acid and 1,4-bis-(hydroxymethyl)cyclohexanone, etc., but also cotton, silk,
It may also be a blended product with natural fibers such as wool. In order to dye polyester fibers according to the method of the present invention, since the dye represented by the general formula [1] shown above is insoluble or soluble in water, a condensate of naphthalene sulfonic acid and formaldehyde is used as a dispersant in a conventional manner. , higher alcohol sulfate, higher alkylbenzene sulfonate, etc., may be used to prepare a dyeing bath or printing paste dispersed in aqueous soot, and dyeing or printing may be carried out.

For example, in the case of dip dyeing, high temperature dyeing method, carrier dyeing method,
By applying a conventional dyeing process such as a thermosol dyeing process, it is possible to dye polyester fibers or their blends with excellent fastness. In this case, even better results can be obtained if an acidic substance such as formic acid, acetic acid, phosphoric acid, or ammonium sulfate is added to the dye. Furthermore, the dye represented by the above general formula [1] used in the method of the present invention may be used in combination with similar gun dyes or pond dyes, among which dyes represented by the above general formula [1] Good results, such as improved dyeing properties, may be obtained by combining them with each other.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to these examples unless it exceeds the gist thereof. In addition, in Examples 1 to 3 and Comparative Examples 1 to 3, the dye concentration was measured by dissolving and extracting the dye from the polyester dyed material using hexafluoroisopropyl alcohol, and colorimetrically quantifying the dye concentration. , and the values in the comparative examples for the examples are expressed as 100, and the light fastness was measured by the fader method based on JISL Misaki 42 (1971).

Example 1 A stain was prepared by dispersing 0.5 parts of a dye represented by the following structural formula in 3 parts of water containing 1 part of a naphthalene sulfonic acid formaldehyde condensate and 2 parts of a higher alcohol sulfate ester.

100% polyester fiber was soaked in this dye, 13%
After dyeing at 0°C for 60 minutes, a bright red dyed fabric was obtained by soaping, washing with water, and drying. Table 1 shows the light fastness of the dyed fabric obtained and the dyeing density of the above-mentioned dye, with the value in Comparative Example 1 shown below being taken as 100. The dye used in this example was obtained by diazotizing 2-methyl-4-nitroaniline by a conventional method and producing 4-hydroxynaphthalic acid-N-(2-hydroxyethoxyethyl)-
Produced by coupling with imide. Comparative Example 1 Polyester fibers were dyed in the same manner as in Example 1 except that a dye having the structural formula shown in Table 1 was used to obtain a red beam cloth.

The evaluation is shown in Table-1. Table 11: Dyeing density is Comparative Example 1
The value is expressed as 100.

Example 2 0.5 parts of a dye represented by the following structural formula was dispersed in 3 parts of water containing 1.5 parts of a naphthalene sulfonic acid formaldehyde condensate and 1 part of a higher alcohol sulfate ester, and 15 parts of a methylnaphthalene-based carrier was dispersed in this*. was added to prepare the chromatase.

Soak 100 pieces of polyester fiber in this dyeing bath,
After dyeing at 0°C for 90 minutes, a bright red dyed fabric was obtained by soaping, washing with water, and drying. Table 2 shows the light fastness of the obtained beam cloth and the dyeing density of the above-mentioned dye, with the value in Comparative Example 2 described below being taken as 100. The dye used in this example was produced by acetylating the dye used in Example 1 with acetic anhydride.
Comparative Example 2 Polyester fibers were dyed in the same manner as in Example 2 except that a dye having the structural formula shown in Table 2 was used to obtain a red beam cloth.

The evaluation is shown in Table-2. Table 2 The dyeing density is expressed with the value of Comparative Example 2 as 100.

Example 3 A dyed product was prepared by the method described in Example 1 using 0.5% of a dye represented by the following structural formula.

Soak 100 pieces of polyester fiber in this beam color bath,
After dyeing at 0qo for 6 minutes, a bright red dyed fabric was obtained by soaping, washing with water, and drying. Table 3 shows the light fastness of the obtained beam cloth and the dyeing density of the above-mentioned dye, with the value in the following comparative example being set as 100. The dye used in this example was produced by propionylating the dye used in Example 1 with propylene anhydride.

Comparative Example 3 Polyester fibers were dyed in the same manner as in Example 3 except that a dye having the structural formula shown in Table 1-3 was used to obtain a red beam cloth.

The evaluation is shown in Table-3. Table 3 Breast The dyeing density is expressed with the value of Comparative Example 3 as 100.

Example 4 Polyester fibers were dyed using the dyes shown in Table 4 below in the same manner as in Example 1 to obtain dyed products having the colors shown in the table.

Table 4 General formula Example 5 The maximum absorption wavelength ^max (acetone) and melting point of the dyes shown in Table 4 of Examples 1 to 3 and Example 4 are shown in Table 5 below.

Table-5

Claims (1)

[Claims] 1. Polyester fibers are represented by the general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^1 is a hydrogen atom, an acetyl group, a propionyl group, an n-butyryl group, an isobutyryl group, A method for dyeing polyester fibers, the method comprising dyeing polyester fibers using an azo dye represented by n-valeryl group or isovaleryl group.