JPS5939554B2 - 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 /＼ °冫～-～Ma:2: (wherein, R3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, R", R゜, R゜, R" is a hydrogen atom, a nitro group, a cyano group, a carboxy group, a halogen atom, a substituted or unsubstituted alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, an acylamino group, an alkylsulfonyl group , arylsulfonyl group, aminosulfonyl group, and aminocarbonyl group.

It is known (Japanese Patent Publication No. 49-21270) that the azo dye represented by ) dyes synthetic fibers red to orange-red. The present inventors have discovered that dyes having the above-mentioned basic skeleton,
As a result of intensive studies to improve its characteristics, the general formula [
I] (wherein R1 is a lower alkyl group, a lower alkoxyalkyl group, a lower alkoxyalkoxyalkyl group, an aralkyl group, an aryloxy lower alkyl group, a halogeno lower alkyl group, a cyano lower alkyl group, a cycloalkyl group, an alkoxycarbonyl lower alkyl group) R2 represents a lower alkoxyalkyl group or a lower alkoxyalkoxyalkyl group.

) If polyester fibers are dyed using the new azo dye represented by the above, a vivid red dyed product with excellent fastness and dyeing density can be obtained compared to when using the above-mentioned known dyes. The present invention was achieved based on the discovery that this is extremely high. To explain the present invention in detail,
In the general formula [1] shown above, R1 is a methyl group, an ethyl group, a linear or branched propyl group, a butyl group,
Lower alkyl groups such as pentyl group and hexyl group; lower alkoxyalkyl groups such as methoxyethyl group, ethoxyethyl group, propoxyethyl group, butoxyethyl group, methoxypropyl group, engineered toxypropyl group, propoxypropyl group, butoxypropyl group Group; lower alkoxyalkoxyalkyl group such as methoxyethoxyethyl group, ethoxyethoxyethyl group, propoxyethoxyethyl group, butoxyethoxyethyl group, methoxyethoxypropyl group, ethoxyethoxypropyl group, propoxyethoxypropyl group, butoxyethoxypropyl group ; Aralkyl groups such as benzyl group, methylbenzyl group, methoxybenzyl group, chlorobenzyl group, phenethyl group, chlorophenethyl group; Aryloxy lower alkyl group such as phenoxyethyl group, methylphenoxyethyl group, methoxyphenoxyethyl group Group; Halogeno lower alkyl group such as chloroethyl group, bromoethyl group; Cyano lower alkyl group such as cyanoethyl group; Cycloalkyl group such as cyclohexyl group; Alkoxycarbonyl lower alkyl group such as methoxycarbonylmethyl group, methoxycarbonylethyl group group; acyloxy lower alkyl group such as acetyloxyethyl group, benzoyloxyethyl group; hydroxy lower alkyl group such as hydroxyethyl group; amino lower alkyl group such as aminoethyl group; methylaminoethyl group, diethylaminoethyl group,
Substituted amino lower alkyl groups such as benzoylaminoethyl group, ethylcarbonylaminoethyl group, ethylsulfonylaminoethyl group, morpholinomethyl group; aryl groups such as phenyl group, chlorophenyl group, methylphenyl group, methoxyphenyl group, etc. and R2 is a lower alkoxyalkyl group such as methoxyethyl group, ethoxyethyl group, propoxyethyl group, butoxyethyl group, methoxypropyl group, ethoxypropyl group, propoxypropyl group, butoxypropyl group; methoxyethoxyethyl group, ethoxy Examples include lower alkoxyalkoxyalkyl groups such as ethoxyethyl group, propoxyethoxyethyl group, butoxyethoxyethyl group, methoxyethoxypropyl group, ethoxyethoxypropyl group, propoxyethoxypropyl group, and butoxyethoxypropyl group. The dye represented by the general formula [1] used in the present invention can be produced, for example, by the following method.

The following general formula [] (wherein, R2 has the same meaning as in the above general formula [1]).

) is diazotized by a conventional method to form a compound of the following general formula [dish (wherein R1 has the same meaning as in the above general formula [1]).

) It can be produced by coupling with a 4-hydroxynaphthalic acid imide represented by: Fibers to be applied in the present invention include polyester fibers made of polyethylene terephthalate, polycondensates of terephthalic acid and 1,4-bis-(hydroxymethyl)cyclohexane, etc., but also fibers made of cotton, silk, wool, etc. It may also be a mixture with natural fibers.

In order to dye polyester fibers according to the method of the present invention, naphthalene sulfonic acid and formaldehyde are used as dispersants in a conventional manner, since the dye represented by the general formula [1] shown above is insoluble or sparingly soluble in water. Dyeing or printing may be carried out by preparing a dyeing bath or printing paste in which a condensate of , higher alcohol sulfuric ester, higher alkylbenzene sulfonate, etc. is dispersed in an aqueous medium.

For example, in the case of 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 dyeing bath. Furthermore, the dye represented by the general formula [1] used in the method of the present invention may be used in combination with dyes of the same type or dyes of other types, and among these, the dye represented by the 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 the gist thereof is exceeded.

In Examples 1 to 3 and Comparative Examples 1 to 3, the dye concentration was measured by dissolving the dyed polyester material using hexafluoroisopropanol, colorimetrically quantifying the dye concentration, and comparing each example with the other. The value in the example is expressed as 100, and the light fastness is JISLO842.
(1971), measured by the fade meter method,
Sublimation fastness was measured using an iron tester (180° C. x 30 sec.) based on JISLO854 (1967).

Example 1 A dye bath was prepared by dispersing 0.59 of a dye represented by the following structural formula in water 31 containing 19 of a naphthalene sulfonic acid formaldehyde condensate and 29 of a higher alcohol sulfuric ester.

Polyester fiber 1009 was immersed in this dyeing bath, and 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 and sublimation fastness of the dyed fabric obtained, as well as the dyeing density of the above-mentioned dye, with the value in Comparative Example 1 set as 100. The dye used in this example was 2-
It was produced by diazotizing aminobenzoic acid-β-(β-monoethoxyethoxy)ethyl ester by a conventional method and coupling it with 4-hydroxynaphthalic acid-N-methylimide.

Maximum absorption wavelength λMax of the obtained dye (chloroform)
was 508 nm, and the separation point was 125-127°C.

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 dyed cloth.

The evaluation is shown in Table-1. Example 2 0.5f1 of a dye represented by the following structural formula was dispersed in water 31 containing 1.59 of a naphthalene sulfonic acid formaldehyde condensate and 19 of a higher alcohol sulfate ester, and a methylnaphthalene carrier 159 was added to the dye bath. was prepared.

Polyester fiber 1009 was immersed 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 and sublimation fastness of the dyed fabric obtained, as well as the dyeing density of the above-mentioned dye, with the value in Comparative Example 2 described below taken as 100. The dye used in this example was 2-
It was produced by diazotizing aminobenzoic acid monoβ-methoxyethyl ester by a conventional method and coupling it to 4-hydroxynaphthalic acid-N-methylimide.

Maximum absorption wavelength λMax of the obtained dye (chloroform)
was 508 nm, and the melting point was 138-139°C. 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 dyed fabric.

The evaluation is shown in Table-2. Example 3 A dye bath was prepared by the method described in Example 1 using 0.59 of a dye represented by the following structural formula.

100g of polyester fiber was immersed in this dyeing bath,
After dyeing at 0°C for 60 minutes, a bright red dyed fabric was obtained by soaping, washing with water, and drying. Table 3 shows the light fastness and sublimation fastness of the dyed fabric obtained, as well as the dyeing density of the above-mentioned dye, with the values in Comparative Example 3 described below being taken as 100. The dye used in this example was 4-
It was produced by diazotizing aminobenzoic acid-β-methoxyethyl ester by a conventional method and coupling it with 4-hydroxynaphthalic acid-N-ethylimide.

Maximum absorption wavelength λMax of the obtained dye (chloroform)
was 510 nm, and the melting point was 143-145°C. 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 3 was used to obtain a red dyed fabric.

The evaluation is shown in Table-3. Example 4 In the same manner as in Example 1, polyester fibers were dyed using the dyes shown in Tables 4, 5, and 6 below to obtain dyed products having the tones shown in the same table.

Example 5 The maximum absorption wavelength λMax (chloroform) of the dyes shown in Tables 4, 5 and 6 above is shown in Table 17 below.
, shown in Table-8 and Table-9.

Claims (1)

[Claims] 1. Polyester fiber is defined by the general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・〔I
] (In the formula, R^1 is a lower alkyl group, a lower alkoxyalkyl group, a lower alkoxyalkoxyalkyl group, an aralkyl group, an aryloxy lower alkyl group, a halogeno lower alkyl group, a cyano lower alkyl group, a cycloalkyl group, an alkoxycarbonyl lower Indicates an alkyl group, acyloxy lower alkyl group, hydroxy lower alkyl group, amino lower alkyl group, methylaminoethyl group, dimethylaminoethyl group, benzoylaminoethyl group, ethylsulfonylaminoethyl group, morpholinomethyl group, or aryl group, R^ 2 represents a lower alkoxyalkyl group or a lower alkoxyalkoxyalkyl group.