JPS5818470B2 - General information - Google Patents

Description

[Detailed description of the invention] The present invention relates to a method for dyeing synthetic fibers.

More specifically, the object of the present invention is to dye synthetic fibers, particularly polyester fibers, in vivid orange to red tones.

The purpose is therefore to prepare synthetic fibers according to the method of the invention of the following general formula CI group or lower alkoxy group, R1 represents a hydrogen atom, a substituted or unsubstituted alkyl group or an aralkyl group, R2 represents a substituted or unsubstituted alkyl group,
It represents a cycloalkyl group, an aralkyl group or an aryl group, R3 represents a hydrogen atom or a lower alkoxy group, and R4 represents a hydrogen atom, a halogen atom, a lower alkyl group, a hydroxy group or an acylamino group.

) is achieved by dyeing with an azo dye containing no sulfonic acid group.

To explain the present invention in detail, the compound represented by the general formula CI) is a novel azo dye, and R in the general formula CI) is a novel azo dye.
In addition to the hydrogen atom, there are linear or branched unsubstituted groups such as methyl, ethyl, isopropyl, n-propyl, isobutyl, n-butyl, pentyl, and hexyl groups. Alkyl group; hydroxyalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, acyloxyalkyl group, cyanoalkyl group, aminoalkyl group, N-N-dialkylaminoalkyl group, monoalkylamino/alkyl group, halogenated alkyl group, Substituted alkyl groups such as carboxyalkyl groups; cycloalkyl groups such as cyclohexyl groups; benzyl groups,
Aralkyl groups such as phenethyl; aryl groups such as phenyl, chlorphenyl, methoxyphenyl, nitrophenyl, tolyl, xylyl, alkylaminophenyl, etc.; hydroxy groups; methoxy, ethoxy, etc. In addition to the hydrogen atom, R1 includes a methyl group, ethyl group, isopropyl group, n-propyl group, isobutyl group, n-butyl group,
Straight chain or branched unsubstituted alkyl groups such as pentyl group and hexyl group: hydroxyalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, acyloxyalkyl group, cyanoalkyl group, halogenated alkyl group, etc. Substituted alkyl groups such as benzyl group, aralkyl group such as phenethyl group: R2 is a methyl group, ethyl group, isopropyl group, n-propyl group, isobutyl group, n-butyl group, pentyl group, hexyl group etc. Straight chain or branched unsubstituted alkyl group; substituted alkyl group such as hydroxyalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, acyloxyalkyl group, cyanoalkyl group, cyclohexyl group such as dichlorohexyl group; Aralkyl groups such as alkyl groups, benzyl groups, and phenethyl groups: Aryl groups such as phenyl groups, chlorophenyl groups, methoxyphenyl groups, nitrophenyl groups; R3 is a methoxy group in addition to the hydrogen atom;
Lower alkoxy groups such as ethoxy groups; R4 includes halogen atoms such as chlorine and bromine atoms in addition to hydrogen atoms; lower alkyl groups such as methyl and ethyl groups; hydroxy groups; acetylamino groups and glopionyl Examples include acylamino such as an amino group.

The azo dye of the paw general formula (, I) used in the present invention is, for example, the following general formula [■] (wherein R has the same meaning as in the paw general formula [I]).

3-amino-4-bromophthalic acid imides represented by ) are diazotized by a conventional method to obtain the general formula (IIIl, ) (wherein R1, R2, R3 and R4 are the front leg general formula [I]
has the same meaning as in .

) can be produced by coupling with a substituted aniline represented by

In addition, 3-amino-4- represented by the forefoot general formula [■]
Bromphthalic acid imides can be produced, for example, by the following method.

(In the formula, R has the same meaning as in the forepaw general formula [I].

), that is, phthalic anhydride in Industrial Chemistry Magazine 65128 (1
962), followed by imidization by a conventional method and nitration at 65° C. in a sulfuric acid medium to obtain 3-nitro-4-bromophthalic acid imide in a relatively high yield. 3-amino-4-bromophthalic acid imide is obtained by reduction.

The synthetic fibers applicable in the present invention include fibers made of synthetic polymeric substances or semi-synthetic polymeric substances, particularly polyethylene terephthalate, terephthalic acid and 1.4
Examples include polyester fibers made of polymers of bis(hydroxymethyl)cyclohexane, such as polyester ether fibers, polyacrylonitrile fibers,
May be polyamide fibers, polyurethane fibers, triacetate fibers, diacetate fibers (also blends of these synthetic fibers, cotton, silk).

It may also be a blended product with natural fibers such as wool.

In order to dye the synthetic fibers according to the method of the present invention, since the dye of general formula CI) is insoluble or sparingly soluble in water, a condensate of naphthalene sulfonic acid and formaldehyde is used as a dispersant in a conventional manner. Dyeing or printing can be carried out by preparing a dyeing bath or printing paste in which higher alcohol sulfuric esters, higher alkylbenzene sulfonates, etc. are dispersed in an aqueous medium.

For example, in the case of dyeing, high temperature dyeing method, carrier dyeing method,
If a normal dyeing process such as thermosol dyeing process is applied, polyester fiber 1. triacetate fiber,
Polyamide fibers, diacetate fibers, or their blends can be dyed with excellent fastness.

In this case, if an acidic substance such as formic acid, acetic acid, phosphoric acid, or ammonium sulfate is added to the dyeing bath depending on the case, even better results can be obtained. However, the present invention is not limited to these examples unless they go beyond the gist of the invention.

In addition, the maximum absorption wavelength (λmax) in the following examples
was measured in acetone.

Example 1 Azo dye represented by the following structural formula (λmax=475 nm) 0.5
1 to naphthalene sulfonic acid/formaldehyde condensate 1
A dyeing bath was prepared by dispersing it in water 31 containing V and 2 g of higher alcohol marrow acid ester.

100g of polyester fiber was immersed in this dyeing bath for 130g.
After dyeing at ℃ for 60 minutes, soaping, washing with water, and drying, a polyester fiber dyed in a bright orange color with good light fastness and sublimation fastness was obtained.

The dye represented by the above structural formula used in this example was obtained by diazotizing 3-amino-4-bromophthalic acid methylimide by a conventional method and coupling it with N-(2-cyanoethyl)-N-ethylaniline. Obtained.

Example 2 Azo dye represented by the following structural formula (λmax=489 nm) 0.5
? Naphthalene sulfonic acid/formaldehyde condensate 1
．． Water containing 52 and 1 g of higher alcohol sulfate 31
Dispersed in methylnaphthalene carrier 15
A dye bath was prepared by adding ft.

100g of polyester fiber was immersed in this dyeing bath,
After dyeing at 0° C. for 90 minutes, the dyed material was washed with saw pink water and dried to obtain polyester fibers dyed in bluish red with good fastness.

The dye shown by the above structural formula used in this example was obtained by diazotizing 3-amino-4-bromophthalic acid-3-methoxyglopylimide by a conventional method and producing N-(2-hydroxyethyl)-
Obtained by coupling with N-ethyl-m-1 luidine.

Example 3 Azo dye represented by the following structural formula (λmax=523 nm)
By using 0.51 and preparing a dyeing bath in the same manner as in Example 1, the polyester fibers were treated.
Polyester fibers dyed in bright scarlet with good fastness were obtained.

Example 4 Polyester fibers were dyed using the azo dyes shown in the table below in the same manner as in Example 1 to obtain dyed products having the tones shown in the right column of the table.

Claims (1)

[Scope of Claims] 1 Synthetic fibers are defined by the general formula (wherein R is a hydrogen atom, a methyl group, a 3-methoxyethyl group, an N-N-diethylaminepropyl group, a benzyl group,
Represents a phenyl group, cyclohexyl group, hydroxy group or methoxy group, R1 is a hydrogen atom, methyl group, ethyl group, hydroxyethyl group, cyanethyl group, acetoxyethyl group, methoxycarbonylethyl group, methoxyethyl group, benzyl group, cyclohexyl or phenyl group, R2 represents a methyl group, ethyl group, hydroxyethyl group, cyanethyl group, acetoxyethyl group, methoxycarbonylethyl group, methoxyethyl group, benzyl group, cyclohexyl group, or phenyl group, R3 represents hydrogen represents an atom or a methoxy group, R4 is a hydrogen atom, a chlorine atom,
Indicates a methyl group, acetylamino group or hydroxy group. ) A method for dyeing synthetic fibers, which is characterized by dyeing using an azo dye containing no sulfonic acid groups.