JPS6350378B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel monoazo compound and a method for dyeing synthetic fibers using the same.
More specifically, the present invention is based on the general formula [] (In the formula, X represents a hydrogen atom, chlorine atom, bromine atom, iodine atom, or cyano group, Y represents a nitro group, cyano group, chlorine atom, or bromine atom, and when X represents an iodine atom or a cyano group, A method for dyeing synthetic fibers characterized by using a monoazo compound represented by (a hydrogen atom may also be represented) and a method for dyeing synthetic fibers using the monoazo compound. Conventionally, monoazo compounds using naphthylamine-based coupling components have been used as disperse dyes to dye synthetic fibers such as polyester fibers, but all of these have N-alkyl derivatives of naphthylamine as coupling components. However, it had fatal defects in dyeing performance, such as extremely poor sunlight hardness, poor dyeability, and poor sublimation fastness. As a result of intensive studies to solve these problems, the present inventors have discovered that a new monoazo compound containing an N-aryl derivative of naphthylamine as a coupling component has extremely high dyeing properties on synthetic fibers such as polyester fibers. It has been found that it has excellent fastness to sunlight and fastness to sublimation. As a result, it was possible to obtain a blue dye that was inexpensive and had excellent fastness. Furthermore, the monoazo compound in the present invention is highly useful as a coloring agent for resin molded products such as polyester. In the present invention, the monoazo compound represented by the general formula () is a monoazo compound represented by the general formula () (In the formula, X represents the above meaning.) The diazo compound obtained by diazotizing the amine represented by the general formula () (In the formula, Y represents the above-mentioned meaning.) It is manufactured by coupling reaction with an N-aryl-1-naphthylamine derivative represented by the following formula. As the amine represented by the general formula (),
Specifically, the following can be mentioned. 2-cyano-4-nitroaniline, 2-chloro-4-nitro-6-cyanoaniline, 2-bromo-4-nitro-6-cyanoaniline, 2-iodo-4-nitro-6-cyanoaniline, 2, 6-dicyano-4-nitroaniline N-aryl-1 represented by the above general formula ()
-Specific examples of naphthylamine derivatives include the following. N-phenyl-1-naphthylamine, N-(4
-nitrophenyl)-1-naphthylamine, N-
(3-nitrophenyl)-1-naphthylamine, N
-(2-nitrophenyl)-1-naphthylamine,
N-(4-cyanophenyl)-1-naphthylamine, N-(3-cyanophenyl)-1-naphthylamine, N-(2-cyanophenyl)-1-naphthylamine, N-(4-bromophenyl)-1-naphthylamine, N- (3-bromophenyl)-1-naphthylamine, N-(2-chlorophenyl)-1-naphthylamine In the present invention, diazotization of the amine of general formula () is carried out by a conventional method, ie, a method using a mineral acid and sodium nitrite; This can be carried out by a method using nitrosyl sulfate. Diazotization can also be carried out by reacting nitrite alcohol ester in a suitable organic solvent such as alcohol. The coupling reaction is achieved by dissolving or emulsifying the coupling component represented by the above general formula () in a mineral acid or organic solvent and mixing it with the diazo compound. For dyeing using the monoazo compound of the present invention, one or more monoazo compounds represented by the general formula () are ground into fine particles in an aqueous medium together with an appropriate dispersant, and then dispersed. do. The dispersed dye is used in the form of a paste or in the form of a powder by spray drying.
Synthetic fibers such as polyester fibers are immersed in an aqueous medium using the dye composition thus obtained, and the dye composition is heated to a temperature of 105°C or higher, preferably 110 to 140°C, under pressure.
Stain at °C. It is also possible to dye in the presence of a carrier such as 0-phenylphenol or trichlorobenzene at a relatively high temperature, for example in the boiling state of water. It is also possible to perform so-called thermosol dyeing, which involves applying a dye dispersion onto cloth and drying it at 150 to 230°C for 30 to 60 seconds. On the other hand, in the case of textile printing, the dye dispersion is kneaded with a suitable sizing agent, printed on cloth, and dyed by steaming or thermosol treatment. or,
A solvent dyeing method using an organic solvent such as trichlorethylene or perchloroethylene as a dyeing medium is also possible. Next, the present invention will be explained in more detail with reference to Examples. The middle part of the example represents parts by weight. Example 1 18.8 parts of 2,6-dicyano-4-nitroaniline is diazotized using nitrosyl sulfuric acid at a temperature below 10°C. On the other hand, N-phenyl-1-naphthylamine
21.9 parts were dissolved in methanol, and the diazo solution was added dropwise thereto at 0 to 5°C for coupling.
Separately, the precipitated crystals are washed and dried. Formula (1) 29.3 parts of a monoazo compound represented by was obtained. Yield 70% λmax (DMF) 610 nm [Staining example] 1 part of the monoazo compound represented by formula (1) was mixed with 1 part of formalin condensate of naphthalene-β-sulfonic acid,
Atomized and dispersed with 1 part of sodium lignin sulfonate, and mixed with 3 parts of higher alcohol sulfate ester in water.
Prepare a dye bath by uniformly dispersing 3000 parts. 100 parts of processed polyester yarn fabric is immersed in this dye bath,
Perform staining at 130°C for 60 minutes. The dyed material was then subjected to reduction cleaning treatment at 85°C for 10 minutes with a reduction dye treatment solution consisting of 3 parts caustic soda, 3 parts hydrosulfite, 3 parts betaine type amphoteric surfactant, and 3000 parts water, and then washed with water. and dried. A dyed product having a clear greenish blue hue with high density and excellent sublimation fastness and wet fastness was obtained. The following compounds were synthesized in the same manner as in Example 1 and used to dye polyester fibers. The results are shown in Table 1. 【table】

Claims (1)

[Claims] 1 General formula () (In the formula, X represents a hydrogen atom, chlorine atom, bromine atom, iodine atom, or cyano group, Y represents a nitro group, cyano group, chlorine atom, or bromine atom, and when X represents an iodine atom or a cyano group, A monoazo compound represented by (may also represent a hydrogen atom). 2 General formula () (In the formula, X represents a hydrogen atom, chlorine atom, bromine atom, iodine atom, or cyano group, Y represents a nitro group, cyano group, chlorine atom, or bromine atom, and when X represents an iodine atom or a cyano group, A method for dyeing synthetic fibers, characterized by using a monoazo compound represented by (may also represent a hydrogen atom).