JPS60208362A - Disazo dye for synthetic fiber - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [X is H, halogen, nitro, alkoxycarbonyl, or acetyl; Y is cyano, or alkoxycarbonyl; R<1> is methyl, ethyl or phenyl; R<2> is H or (substituted)alkyl]. EXAMPLE:A compound of formula II. USE:Dye capable of dyeing synthetic fibers such as polyester, triacetate, diacetate orange - red. Excellent in resistance to light, sublimation and water. PREPARATION:An amine of formula III is diazotized followed by coupling between the resulting diazo compound and an aminothiophene of formula IV. The monoazo compound of formula V thus formed is diazotized followed by coupling the resultant diazo compound and a pyridone of formula VI.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a disazo dye for synthetic fibers, and more specifically, a disazo dye having no substituent at the 5-position of the pyridone ring, which is suitable for use in synthetic fibers, especially polyethylene terephthalate fibers ( The present invention relates to a thiophene disazo dye that can dye polyester fibers (hereinafter referred to as polyester fibers) in orange to red.

Conventionally, the dye represented by -R'' below has been known as a disazo dye for synthetic fibers (JP-A-Sho, lli/-1
1/134I Publication). The dye has pyrido-dione ring-forming fibers, which are the second coupling component, in the matrix skeleton in a purple to purple color.
A dye that dyes blue-green.

An object of the present invention is to provide a disazo dye having no substituent at the 3-position of the pyridone ring, which dyes synthetic fibers orange to red.

In formula C, X represents a hydrogen atom, a halogen atom, a nitro group, an alkoxycarbonyl group, or an acetyl group, Y represents a cyano group or an alkoxycarbonyl group, ul represents a methyl group, an ethyl group, or a phenyl group, and R3 represents hydrogen The gist is a disazo dye for synthetic fibers represented by an atom or a substituted or unsubstituted alkyl group.

The halogen atom represented by X in the forepaw general formula [I] includes a chlorine atom, a bromine atom, an iodine atom,
Examples of the alkoxycarbonyl group represented by Examples include branched propyl groups, butyl groups, pentyl groups, hexyl groups, heptyl groups, octyl groups, etc.
Substituted alkyl groups include lower alkoxyalkyl groups such as methoxyethyl group, ethoxyethyl group, γ-methoxyglobyl group, and γ-isopropyloxyglobil; phenoxyalkyl groups such as phenoxyethyl group; benzyloxyethyl group, chlorobenzyl group. Alkyloxyethyl groups that may be substituted such as oxyethyl groups; 7-ralkyl groups such as benzyl groups and phenethyl groups; hydroxyethyl groups, hydroxyalkyl groups, hydroxybutyl groups, hydroxyhexyl groups, and euhydroxy-3-methoxy7 '.

Optionally substituted hydroxyalkyl groups such as bir group; cyano lower alkyl groups such as cyanmethyl group and cyanethyl group; substituted hydroxyalkyl groups such as acetyloxyethyl group, chloropropionyloxyethyl group, and hendiyloxyethyl group Good acyloxy lower alkyl group: Alkoxycarbo 3-nyloxy lower alkyl group such as methoxycarbonyloxyethyl group, methoxyethoxycarbonyloxyethyl group; methoxycarbonylmethyl group, ethoxycarbonylethyl group, methoxycarbonylethyl group, methoxyethoxycarbonylethyl group , optionally substituted alkoxycarbonyl lower alkyl groups such as benzyloxycarbonylethyl group; allyloxycarbonyl lower alkyl groups such as allyloxycarbonylethyl group and allyloxycarbonylmethyl group; tetrahydrofurfuryl group; chloroethyl group, chlorobutyl group ,
Examples include halogenoalkyl groups such as chlorohexyl group.

The disazo dye represented by the general formula [■] is obtained by diazotizing amines represented by the following general formula [old (in the formula or the same as the definition of general formula (1)), and the diazotization (in the formula, Y is the general formula [
(same as the definition of
and Y is the same as the definition of general formula [■]) is diazotized, and the diazotized product and the following general formula [
■] I 8 (In the formula, R' and R2 are the same as the definition of general formula [I])
It can be produced by coupling with a pyridone represented by

Examples include diacetate fibers and diacetate fibers, and particularly preferred are polyester fibers.

Furthermore, even if the fiber is a blend of the above-mentioned polyester and other fibers and natural fibers such as cotton, silk, and wool, the polyester and other fibers contained therein can be dyed.

To dye the synthetic fibers using the dye of the present invention,
Since the dye represented by the general formula [I] is insoluble or sparingly soluble in water, a dispersing agent is used to prepare a condensate of naphthalene sulfonic acid and formaldehyde, a higher alcohol sulfuric acid ester, or a higher alkylbenzenesulfonic acid. Dyeing or printing may be carried out by preparing a dyeing bath or printing paste in which salt or the like is dispersed in an aqueous medium. For example, in the case of dip dyeing, the synthetic fibers can be dyed with excellent fastness by applying common dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing. Furthermore, if an acidic substance such as formic acid, acetic acid, phosphoric acid or ammonium sulfate is added to the dyeing bath,
Even better results can be obtained.

If synthetic fibers are dyed by the dyeing method described above using the dye of the present invention, a dyed product dyed in orange to red can be obtained.

The dyed product obtained has good fastness properties, especially light fastness, sublimation fastness, and water fastness.
Excellent temperature stability and pH stability during dyeing.

Next, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to the following examples.

Example/ Dye O,jIi shown by the following structural formula is 7talenesulfonic acid-
700g of polyester fiber was immersed in a dyeing bath containing 3t of water containing formaldehyde condensate/g and higher alcohol sulfuric ester-I, dyed at 730°C for 60 minutes, soaped, washed with water and dried, resulting in a red color. A dyed cloth was obtained. The light fastness of the dyed fabric obtained,
Sublimation fastness, water fastness, and temperature stability during dyeing of the above dye, pl (stability) were good.

71 The dye used in this example was produced as follows.

9.31 of aniline is dissolved in 100% of cutihydrochloric acid, the solution is cooled to 1°C and then 2N of sodium nitrite! ;O
added me. At this time, the temperature was set not to exceed dt°C. The obtained aniline diazonium salt solution was subjected to -mono-amino-- shearing, and the precipitated monoazo compound was removed by F.
Washed with water and dried. This monoazo compound (2-amino-
3-cyano-yo-phenylazothiophene)//, is added to a mixture of acetic acid/141- and phosphoric acid//'Imt, and then nitrosylsulfuric acid (sodium nitrite) is added to this mixture at 0-5°C. , 3.kll (prepared by dissolving ?7% sulfuric acid aoi) was gradually added and stirred for 30 minutes at the same temperature to prepare a diazo solution of a monoazo compound.

N-ethyl-coumethyl-6-hydroxypyridone7.
7 g was dissolved in 2 oomt methanol and added to 20011 ice and 100 ml water. Add the diazo solution prepared earlier to this, stir at 0-1°C for several hours,
After removing the precipitated disazo dye, it was washed with water and dried. The maximum absorption wavelength of this product, λma! (acetone) is 419 A
It was in nm.

Example 2 Polyester fibers were dyed according to the method described in Example 1, except that a dye represented by the following structural formula was used, and a red 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/.

The λmax (acetone) of this product was 4I96 nm.

Example 3 A red dyed fabric was obtained when polyester fibers were dyed according to the method described in Example 3, except that a dye represented by the following structural formula was used. The resulting tomo-dyed fabric had good light fastness, sublimation fastness, and water fastness, as well as the temperature stability and pH stability during dyeing of the dye.

The dye used in this example was produced according to Example/.

The λmax (acetone) of this product was jOAnm.

EXAMPLE TE When polyester fiber was dyed according to the method described in Example 1 except that a dye represented by the following structural formula % was used, a red dyed cloth 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/.

The λmax (acetone) of this product was 3.30 nrn.

Example! When polyester fibers were dyed in accordance with the method described in Example 1, except that the dye represented by was used, an orange 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 11-. The λmax (acetone) of this product is 411r/
It was nm.

Example 6 Polyester fibers were dyed in the same manner as in Example 1 using the dyes shown in Table 1 below to obtain dyed products having the colors shown in Table 1.

12- Sender: Mitsubishi Chemical Industries, Ltd. Representative Patent Attorney Hase - (7 others)

Claims (1)

[Claims] (1) General formula (in the formula, or represents a hydrogen atom, a halogen atom, a nitro group, an alkoxycarbonyl group, or an acetyl group, Y represents a cyan group or an alkoxycarbonyl group, and R' represents a methyl group, an ethyl group, or a phenyl group) and R2 represents a hydrogen atom or a substituted or unsubstituted alkyl group).