JPH0124178B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to monoazo dyes for synthetic fibers. Specifically, the present invention relates to an azo dye that dyes synthetic fibers, particularly polyester fibers, in bright blue to green colors with excellent sublimation fastness, light fastness, post-processing resistance, and alkali discharge printing resistance. . The present invention will be explained in detail below. The dye according to the present invention has the following general formula [] (In the formula, R ¹ represents a C _1-4 alkyl group, a cyano C _2-4 alkyl group, or -R ² -OCOCH ₂ OR ³ , and R ²
represents a C _2-4 alkylene group, R ³ represents a C _1-4 alkyl group, a C _1-4 alkoxy C _2-4 alkyl group, a phenyl group, a benzyl group or a phenethyl group,
represents a hydrogen atom, a methyl group, an acetylamino group or a propionylamino group. ) is a water-insoluble monoazo dye. The dye represented by the above general formula [] is a diazonium salt of 2-amino-3,5-dinitrothiophene, which is prepared by the following general formula [] It can be produced by coupling with an aniline represented by the formula (wherein R ¹ , R ² , R ³ and X are the same as defined above). Specific examples of anilines represented by the general formula [] are N,N-di-β-methoxyacetoxyethylaniline, N,N-di-β-methoxyacetoxyethyl-
m-Toluidine, 3-acetylamino-N,N-di-β-methoxyacetoxyethylaniline, 3-propionylamino-N,N-di-β-methoxyacetoxyethylaniline, 3-acetylamino-N,N-di -β(-β'-methoxyethoxy)acetoxyethylaniline, N-ethyl-N-β-phenoxyacetoxyethylaniline, N-cyanoethyl-N-β-methoxyacetoxyethyl-m-toluidine, 3-acetylamino- Examples include N,N-di-β-butoxyacetoxyethylaniline, N,N-di-β-phenoxyacetoxyethyl-meth-toluidine, and the like. Synthetic fibers that can be dyed with the dye of the present invention include fibers made of synthetic polymer substances such as polyester, polyester ether, polyamide, and polyurethane; fibers made of semi-synthetic polymer substances such as triacetate and diacetate; Examples include blends of synthetic fibers or blends of natural fibers such as cotton, silk, and wool, but especially polyethylene terephthalate, terephthalic acid, and 1,4-
Fibers made of polyester such as a polycondensate with bis-(hydroxymethyl)cyclohexane are preferred. In order to dye the synthetic fibers with the dye of the present invention, the dye represented by the general formula [] shown above can be dyed using a conventional method such as a condensate of naphthalene sulfonic acid and formaldehyde, a higher alcohol sulfuric acid ester, a higher alkylbenzene sulfonate, etc. Dyeing or printing may be carried out by dispersing the dye in an aqueous medium to prepare a dyeing bath or printing paste using a dispersing agent. For example, when dyeing is carried out, the synthetic fibers can be dyed with excellent fastness by applying ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing. In some cases, even better results may be obtained by adding an acidic substance such as formic acid, acetic acid, phosphoric acid, or ammonium sulfate to the dyeing bath. Next, the present invention will be explained in more detail with reference to Examples. Example 1 Structural formula below A dyeing bath was prepared by dispersing 0.5 g of the monoazo dye represented by 3 in water 3 containing 1 g of naphthalene sulfonic acid-formaldehyde condensate and 2 g of higher alcohol sulfate. Immerse 100g of polyester fiber in this dyeing bath,
After dyeing at 130°C for 60 minutes, soaping, washing with water, and drying were performed, a polyester fabric dyed in bright blue with good light fastness and sublimation fastness was obtained. The dye used in this example was 2-amino-3,5
-dinitrothiophene was diazotized in accordance with a conventional method and coupled with 3-acetylamino-N,N-di-β-methoxyacetoxyethylaniline. The λ _nax (acetone) of this product was 625 nm. Example 2 Structural formula below 0.5 g of the monoazo dye represented by is dispersed in water 3 containing 1.5 g of naphthalene sulfonic acid-formaldehyde condensate and 1 g of higher alcohol sulfate ester, and a methylnaphthalene carrier 15
A dyeing bath was prepared by adding g. Immerse 100g of polyester fiber in this dyeing bath,
After dyeing at 100° C. for 90 minutes, soaping, washing with water and drying, a polyester cloth dyed in bright blue with good light fastness and sublimation fastness was obtained. The dye used in this example was 2-amino-3,5
-dinitrothiophene was diazotized according to a conventional method and coupled with N,N-di-β-methoxyacetoxyethyl-m-toluidine. The λ _nax (acetone) of this product was 639 nm. Example 3 Structural formula below Example 1 using 0.5 g of monoazo dye shown in
When polyester fibers were dyed in the same manner as above, a polyester cloth with good fastness and vivid blue color was obtained. The dye used in this example was 2-amino-3,5
-Dinitrothiophene was diazotized according to a conventional method, and the diazotized product was coupled with N,N-di-β-methoxyacetoxyethylaniline. The λ _nax (acetone) of this product was 621 nm. Examples 4 to 17 When polyester fibers were dyed in the same manner as in Example 1 using the monoazo dyes shown in Table 1 below, dyed fabrics with the colors shown in the table were obtained. 【table】

Claims (1)

[Claims] 1. General formula (In the formula, R ¹ represents a C _1-4 alkyl group, a cyano C _1-3 alkyl group, or -R ² -OCOCH ₂ OR ³ , and R ²
represents a C _2-4 alkylene group, R ³ represents a C _1-4 alkyl group, a C _1-4 alkoxy C _2-4 alkyl group, a phenyl group, a benzyl group or a phenethyl group,
represents a hydrogen atom, a methyl group, an acetylamino group or a propionylamino group. ) is a monoazo dye for synthetic fibers.