JPS58122965A - Water-insoluble monoazo compound and method for dyeing hydrophobic fiber - Google Patents

Abstract

NEW MATERIAL:Water-insoluble monoazo compounds of formulaI, wherein one of X, Y is H and the other is a nitro group; Z is H, alkyl, alkoxy, alkoxyalkyl; R is H, alkyl, phenyl. USE:Dyes for dyeing or printing hydrophobic fibers, particularly polyester fiber. Color tone is red. PREPARATION:A diazo component of formula II is diazotized by any of conventional methods, and then coupled with a coupling component of formula III.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel water-insoluble monoazo compound and a method for dyeing hydrophobic fibers using the same. More particularly, the present invention relates to a novel water-insoluble monoazo compound and a method using the same for dyeing hydrophobic fibers, sometimes polyester fibers, in a strong red color.

In recent years, in the dyeing industry, there has been a marked trend towards high added value, as well as resource and energy conservation, sometimes in the field of dyeing and processing hydrophobic fibers such as polyester fibers. Therefore, the dyes used for dyeing are required to have excellent performance in all aspects, such as easy dyeing, good dyeing rate, and excellent fastness.

Conventionally, introducing polar groups or increasing the molecular layer to increase fastness has led to problems such as decreased dyeing properties and dye bath stability. Therefore, if the molecular weight is reduced and the number of polar groups is reduced, there is a problem that the fastness to sublimation etc. decreases.

As a result of intensive studies on these problems, the present inventors have found that the problems described in Hu can be solved at once by using a novel monoazo compound represented by the above general formula CI) and substantially described in the literature. They discovered this and completed the present invention. That is, the present invention relates to the general formula [i] (where either X or Y represents a hydrogen atom, the other represents a nitro group, Z represents a hydrogen atom, (3) a lower alkyl group, a lower alkoxy group or a lower alkoxy represents a lower alkoxy group, k represents a hydrogen atom, a lower alkyl group, or a phenyl group) and a method for dyeing hydrophobic fibers characterized by using the water-insoluble monoazo compound.

The term "lower" as used in the present invention preferably has 1 to 4 carbon atoms. The lower alkyl group represented by Z includes methyl group,
Examples of lower alkoxy groups include methoxy, ethoxy, propoxy, and butoxy groups; examples of lower alkoxy groups include methoxyethoxy and ethoxyethoxy groups. Preferred as Z are a hydrogen atom, a methoxy group, an ethoxy group, and a methoxyethoxy group. Examples of the lower alkyl group represented by R include a methyl group, an ethyl group, a propyl group, and a butyl group. Preferred R is a methyl group or an ethyl group.

(4) The monoazo compound represented by the general formula [1] of the present invention can be obtained by adding a diazo component represented by the general formula [n] (wherein, X and Y have the same meanings as above) by a known method. Diazotized, general formula []T
It is obtained by a coupling reaction with a coupling component represented by [ ] (wherein Z and R each represent the above-mentioned meanings).

In addition, the coupling component represented by the general formula [11T) is
An amine compound represented by the general formula [IV] 1tcOR (in the formula, Z and R each represent the above-mentioned meanings) is converted into 2-phenoxy-1-halogenoethane in the presence of a deoxidizing agent such as sodium carbonate or potassium carbonate. Alternatively, it can be obtained by alkylation with 2-phenoxyethyl ester of P-)luenesulfonic acid.

Examples of the diazo component represented by the general formula [II] include 2-nitroaniline and 3-nitroaniline.

As the amine compound represented by the general formula [IV'], 3
-acetylaminoaniline, 3-propionylaminoaniline, 3-benzoylaminoaniline, 3-butyrylaminoaniline, 3. -formylaminoaniline, 2-
Methoxy-5-acetylaminoaniline, 2-ethoxy-5-acetylaminoaniline, 2-methoxyethoxy-5-acetylaminoaniline, 2-ethoxy-5-propionylaminoaniline, 2-ethoxy-5-benzoylaminoaniline, 2 -Methoxyethoxy-5-benzoylaminoaniline, 2-methoxy-5-butyrylaminoaniline, 2-methyl-5-acetylaminoaniline, 2-ethyl-5-propionylaminoaniline and the like.

Specifically, the monoazo compound of the present invention is produced, for example, as follows.

The diazo component represented by the general formula [II] is dissolved or dispersed in a mineral acid such as sulfuric acid, hydrochloric acid, etc. or an organic acid such as acetic acid, propionic acid, etc., and nitrosyl sulfuric acid or sodium nitrite is used at 0 to 10°C. to diazotize. On the other hand, a coupling component represented by the general formula [1113] is dissolved in a mineral acid such as sulfuric acid or hydrochloric acid, an organic acid such as acetic acid or propionic acid, or an organic solvent such as methanol or ethanol, and the diazo The liquid is added cold, preferably below 10° C., and coupled. After the reaction is completed, the precipitated product is separated, washed with water, and dried to obtain a monoazo compound represented by the general formula [I].

Examples of the hydrophobic fibers in the present invention include polyester (7) stellate fibers, polyamide fibers, polyolefin fibers, cellulose ester fibers, and blends of these fibers.

The compound of the present invention exhibits excellent dyeing properties for polyester fibers and blends thereof.

When dyeing hydrophobic fibers using the monoazo compound of the present invention, first, one or more monoazo compounds represented by the general formula CI] are ground into fine particles in an aqueous medium together with a suitable dispersant. Decentralize. The dispersed dye can be used in liquid form as it is or in powder form by spray drying. For dyeing, a dye bath is prepared by dispersing a dispersed dye in an aqueous medium by a method known per se, and the hydrophobic fibers are immersed and dyed at 105°C or higher, preferably 110 to 140°C, under pressure. , in the presence of a carrier such as 0-phenylphenol or trichlorobenzene at a relatively high temperature, e.g., at the boiling state of water, or by padding the fabric with a dye dispersion to
(8) Dyeing is done by the so-called thermosol dyeing method, which involves dry heat treatment at ℃ for 30 to 90 seconds, or in the case of textile printing, the dye dispersion is kneaded with a suitable sizing agent, this is padded onto the cloth, and then dyed. Dyeing can be done by teaming or thermosol treatment.

Further, a solvent dyeing method using an organic solvent such as trichlorethylene or perchlorethylene as a dyeing medium is also possible.

The monoazo compound of the present invention has various dyeing properties, including excellent dyeing properties, decomposition resistance, pH sensitivity, sublimation fastness, water fastness, washing fastness, light fastness, j≠rubbing fastness, etc. Shows good performance in all fastness levels.

EXAMPLES Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited to these Examples. In the examples, unless otherwise specified, parts and parts represent overlapping parts and parts by weight.

Example 1 After heating and melting 718 parts of 2-methoxy-5-acetylaminoanili (9) and adding 10.6 parts of sodium carbonate, 48.2 parts of 2-phenoxy-1-bromoethane was added at 100 to 110°C. The mixture was added dropwise and reacted at the same temperature for 3 hours to obtain 42 parts of 2-methoxy-5-acetylamino-N,N-bis(2-phenoxyethyl)aniline.

This was dissolved in 100 parts of methanol to obtain a coupling component.

On the other hand, 13.8 parts of 2-nitroaniline was diazotized with nitrosyl sulfuric acid at 30 to 40°C, and diazotized with 500 parts of ice water.
The mixture was added to the above-mentioned coupling components to carry out a coupling reaction without being cooled to below °C. The precipitated crystals are collected door to door,
After washing with water and drying, 54.6 parts of a dye represented by formula (1) was obtained. Yield 96% based on the diazo component λmax (in DMF) 535 parts m (10) Example 2 1 part of the dye of formula (1) obtained in Example 1 was dissolved in naphthalene-
A formalin condensate of β-sulfonic acid, INS, is atomized and dispersed together with 1 part of sodium ligninsulfonate, and this and 3 parts of higher alcohol sulfate are uniformly dispersed in 3,000 parts of water to prepare a dye bath.

100 parts of Tetoron spun yarn (polyester fiber, manufactured by Toshisha Co., Ltd.) was immersed in this dye bath and dyed at 130°C for 60 minutes. 3 parts activator and 300 parts water
A light cleaning treatment was performed at 85° C. for 10 minutes using a treatment solution consisting of 0 parts. Thereafter, it was washed with water and dried to obtain a pickled red dyeing with high density and fastness.

Example 3 After heating and melting 15 parts of 3-7 cetyl aminoaniline and adding 13.8 parts of potassium carbonate, P was heated at 110 to 115°C.
-Toluenesulfonic acid-2-phenoxyethyl ester (70.18 g) was added and reacted at the same temperature for 3 hours to produce 3-acetylamino-N,N-bis(2-phenoxyethyl).
39 parts of aniline were obtained. This was dissolved in 100 parts of methanol to obtain a coupling component.

On the other hand, 13.8 parts of 3-nitroaniline was diazotized in the same manner as in Example 1, and this was subjected to a coupling reaction with the coupling component to obtain 52.9 parts of the dye represented by formula (2). Yield: 93% 1max (in DMF > 5250m) Example 4 A dye bath was prepared in the same manner as in Example 2 using 1 part of the dye of formula (2), and dyeing was carried out. A yellowish-red dyed product with excellent fastness was obtained.

Examples 5 to 10 The following dyes were produced in the same manner as in Example 1, and dyeing was performed in the same manner as in Example 2 using the obtained dyes.

The results shown in Table 2 were obtained.

(13) Table 1 Example 11 (14) A dye of the above formula (3) was produced in the same manner as in Example 1, and part of it was mixed with 1 part of a formalin condensate of naphthalene-β-sulfonic acid and lignin sulfone. Atomized and dispersed with 005 parts of acid soda, the obtained dye composition is added to 95 parts of a printing base paste having the following composition, and mixed well to prepare a colored paste.

Printing paste Sodium chlorate 0.6 parts Liquor stone acid 0.4 parts This color paste is printed on polyester processed yarn fabric, and after drying,
High pressure steamer (temperature 130-135℃, gauge pressure 3,
Steaming was carried out for 30 minutes at ~4 instant/crh2). Thereafter, it was washed with water, subjected to reduction washing treatment in the same manner as in Example 2, washed with water, and dried to obtain a highly concentrated and fast red dyed product.

(15 completed)

Claims (2)

[Claims] (1) General formula [I'l (wherein, either X or Y represents a hydrogen atom, the other represents a nitro group, and 2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a lower alkoxy lower alkoxy group) (wherein k represents a hydrogen atom, a lower alkyl group, or a phenyl group). (2) General formula (1'l (wherein, either X or Y represents a hydrogen atom, the other represents a nitro group, and Z represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a lower alkoxy lower alkoxy group) A method for dyeing hydrophobic fibers, characterized in that a water-insoluble monoazo compound is used.