JPS60217268A - Disazo dye - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (X is H, Cl, Br or nitro; Y is H, methyl or Cl; R<1> is alkyl or allyl; R<2> is cyanoethyl, acyloxyethyl or alkoxycarbonyl lower alkyl). EXAMPLE:The compound of formula II. USE:A dye for dyeing and printing polyester fibers, mixed spun fabrics of cotton, etc. with polyester fibers to yellow - red color having improved color fastness to water, perspiration and washing. PREPARATION:An amine of formula III, e.g. p-phenyl azoaniline, is diazotized and then coupled with an aniline of formula IV, e.g. N-ethyl-N-cyanoethylaniline.

Description

[Detailed description of the invention] Industrial applications The present invention relates to disazo dyes.

Conventional technology Conventionally, as a dye for dyeing polyester fibers orange,
The following dyes are known (DT, 20J704t, Publication No. 2).

These dyes have good fastness especially to water after post-processing.

Further improvement in perspiration and washing fastness is desired, and the dye of the present invention relates to a disazo dye in which a monoazo compound having a specific substituent is used as a diazo component, and an aniline compound having a specific substituent is used as a coupling component. There it is,
Polyester fibers or fabrics made from them are dyed yellow to red, and the resulting dyed fabrics have excellent fastness after post-processing, especially wet fastness such as water, sweat, and washing fastness. The object of the present invention is to provide a disazo dye that exhibits excellent pH dependence and temperature stability during ink dyeing.

Means to solve problems The present invention relates to general formula [I] Engineering (In the formula, X is a hydrogen atom, a chlorine atom, or a bromine atom.

or a nitro group, Y represents a hydrogen atom, a methyl group, or a chlorine atom, R1 represents an alkyl group or an allyl group, and R2 represents a cyanoethyl group, an acyloxyethyl group, or an alkoxycarbonyl lower alkyl group). The gist of this paper is the disazo dyes.

The present invention will be explained in detail below.

In the forefoot general formula [1), examples of the alkyl group represented by R1 include a methyl group, an ethyl group, a linear or branched propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, etc. It will be done. Examples of the acyl group of the acyloxyethyl group represented by R2 include acetyl, propionyl, chlorobutyryl, capronyl, and other alkyl acyl groups, ethoxycarbonyl, butoxycarbonyl, 1.2-ethylhexyloxycarbonyl, and other alkoxycarbonyl groups. Base.

benzoyl group, phenoxyacetyl group, 7-enacyl group,
Examples include aryl group-containing acyl groups such as phenoxycarbonyl group and benzyloxycarbonyl group. Also,
Examples of the alkoxy group of the alkoxycarbonyl lower alkyl group include methoxy group, ethoxy group, butoxy group, phenoxyethoxy group, benzyloxy group, or methoxyethoxy group, and examples of the lower alkyl group include methyl group, ethyl group, or propyl group. can give.

The front leg is represented by the general formula [1]. Disazo dyes are produced by diazotizing amino acids represented by the following general formula [II] (wherein, It can be produced by coupling with anilines shown in (same as above).

The disazo dye represented by the general formula CI) is:

The crystal form is β-ferment modified. This in an aqueous medium.

optionally in the presence of a dispersant of a concentrate of sulfide pulp waste liquor based on a formaldehyde condensate of synapthalene sulfonic acid, sodium lignin sulfonate, or alcohols such as methanol, ethanol or butanol; such as dioxane. Ethers; when treated in organic solvents such as glycols and glycol ethers such as ethylene glycol or ethylene glycol monomethyl ether at 1j0~/'70℃ for 30 minutes to 3θ hours, they crystallize into the α-type crystal form. Can be perverted.

4- In the present invention of the effects of the invention, any of these wheat crystal forms can be used, but αN crystal forms are preferred because they can be dyed well even under high temperature conditions. Examples of fibers that can be dyed with the disazo compound of the present invention include polyethylene terephthalate.

Terephthalic acid and/, (7-bis-(hydroxymethyl)
Other polyester fibers can be mentioned, such as polycondensates with cyclohexane. For example, even in blended products and mixed fiber products of natural mk such as cotton, silk, and wool with the above polyester fibers, the polyester in the natural fibers can be used. Fibers can be dyed well.

To dye polyester fibers using the disazo dye of the present invention, the dye of the present invention is dispersed in an aqueous medium using a conventional method using a dispersant such as a condensate of synapthalene sulfonic acid and formaldehyde. Prepare a dyeing bath or printing paste and perform dyeing or printing. For example, in the case of dyeing.

By applying ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing, 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.

In addition, the dye represented by the bending water structural formula [■] used in the method of the present invention may be used in combination with dyes of the same system or dyes of other systems, and the combination of the dyes can improve dyeing properties, etc. Results may be obtained.

Next, the present invention will be explained in more detail with reference to Examples.

Example/Dye θ represented by the following structural formula! Polyester cloth/θ02 was immersed in a dyeing bath in which 2 was dispersed in 3 t of water containing naphthalene sulfonic acid-formaldehyde condensate/f and 2 t of higher alcohol sulfate ester, and dyed at 130°C for ≦θ minutes, followed by soaping and washing with water. After drying, a bright orange dyed fabric was obtained.

The dye used in this example was produced as follows.

Disperse p-phenylazoaniline, θt in water, add 3J% hydrochloric acid, add ice/θV, and add 0.0% sodium nitrite. ? ! Drop a solution consisting of V and 10 tnl of water, and! time.

After stirring at θ to t°C, sulfamic acid θ0.2f was added to prepare a diazo solution. Add N-ethyl-N-cyanoethylaniline/, 2 to the diazo solution and at the same temperature! After stirring for an hour, add sodium acetate to adjust the pH to 2-3.
After further stirring for 3 hours, the mixture was filtered, washed with water, and dried under reduced pressure at 30°C to obtain 3.6f of orange crystals.

1- The obtained powder was of β type modification and its X-ray diffraction pattern is shown in FIG. 3f of the obtained β-type transformed powder was dispersed in water and heated at 90 to 1°C! The mixture was stirred for a period of time to effect crystal transformation. After filtration and drying, an α-type modified product having the X-ray diffraction pattern shown in FIG. 1 was obtained.

That is, this α-modified dye has an X-ray diffraction pattern (OuKα)
, the diffraction angle (2θ)/ri, -2° and 2J, 1
A strong peak of 0, and a diffraction angle (θ), 27.
A peak of intermediate intensity was shown at ♂0.

Example λ A polyester cloth/θ0f is immersed in a dye bath in which dyes θ, j f shown by the following structural formula are dispersed in 3 t of water containing a 7talenesulfonic acid-formaldehyde condensate/f and a higher alcohol sulfate ester co-V. 8-S After dyeing at 130° C. for θ minutes, soaping, washing with water and drying were performed, and a red dyed fabric was obtained.

Example 3 Polyester cloth was dyed using the dyes shown in Table 1 below in the same manner as in Example 1 to obtain dyed cloths having the colors shown in the table.

-15- Comparative Example/ The dye shown in a! is the same as Example/. K and dyed to obtain an orange dyed cloth.

Is the obtained dyed fabric Hytran? -, 24tK (Daiichi Kogyo Seiyaku Co., Ltd., trade name) was used for post-processing.

A dyed cloth after post-processing was obtained. The dyed fabric obtained in Example 1 was also post-processed to obtain a post-processed dyed fabric.

The fastness of each is shown below.

16- (1) A dyed cloth that has been subjected to post-water contamination treatment was subjected to a dyed cloth test according to the J-EIL-Or4ttA method, except that silk cloth was attached instead of nylon cloth to determine the degree of contamination of the silk cloth. Judgment was made using gray scale.

(2) Sweat fastness A dyed fabric that has been subjected to post-processing was tested according to the J-8L-○R IA method, but the attached fabric was a nylon fabric and a silk fabric, and the silk fabric was contaminated. The degree was determined on a gray scale.

(3) Attaching multi-fiber to dyed cloth that has been subjected to post-washing treatment, A
A washing test was carried out in accordance with ATOO washing method No. IA, and contamination of the nylon fibers of the multi-fiber was judged on a gray scale.

[Brief explanation of drawings]

FIG. 1 and FIG. 1 show X-ray diffraction patterns of the α-type modification and the β-type modification of the disazo dye of the present invention obtained in Example. In the figure, the horizontal axis represents the diffraction angle (-0), and the vertical axis represents the diffraction intensity. Applicant: Mitsubishi Chemical Industries, Ltd. Agent: Patent attorney For long diameters - (and 7 others)

Claims (1)

[Claims] (1) General formula [I] (wherein, X represents a hydrogen atom, a chlorine atom, a bromine atom, or a nitro group, Y represents a hydrogen atom, a methyl group, or a chlorine atom, and R1 represents an alkyl group or an allyl group) and R2 represents a cyanoethyl group, an acyloxyethyl group, or a haalkoxycarbonyl lower alkyl group). 1ln