JPH0124180B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to monoazo dyes for synthetic fibers. Specifically, the present invention provides synthetic fibers, especially polyester fibers, which have excellent sublimation fastness, light fastness, post-processing resistance, and alkali discharge printing resistance.
The invention also relates to an azo dye that dyes bright blue to green colors. 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 _5-8 alkyl group or a C _5-8 alkoxyethyl group, and R ² represents a cyano C _1-3 alkyl group, a C _1-4 alkoxycarbonylmethyl group, or
It represents a C _1-4 alkoxyethoxycarbonylmethyl group, and X represents a hydrogen atom, a methyl group, an acetylamino group or a chlorine atom. ) is a water-insoluble azo dye. The dye represented by the above general formula [] is a diazonium salt of 2-amino-3,5-dinitrothiophene, which is expressed by the following general formula [] It is produced by coupling with an aniline represented by the formula (wherein R ¹ , R ² and X are the same as defined above). Specific examples of anilines represented by the general formula [] include N-hexyl-N-(β-cyanoethyl)-m-toluidine, N-hexyl-N-(γ-
cyanopropyl)aniline, 3-acetylamino-N-hexyl-N-cyanomethylaniline, N
-(β-hexyloxyethyl)-N-(β-cyanoethyl)-m-toluidine, N-octyl-N
-(methoxycarbonylmethyl)aniline, N-
heptyl-N-(butoxycarbonylmethyl)-m
-toluidine, 3-acetylamino-N-hexyl-N-(ethoxycarbonylmethyl)aniline,
N-hexyl-N-(β-methoxyethoxy)carbonylmethyl-m-toluidine, N-(2-ethylhexyl)-N-(β-ethoxyethoxy)carbonylmethylaniline, N-(β-heptyloxyethyl)-N -(methoxycarbonylmethyl)
-m-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. Examples include 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 lake 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 chromosome. 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 according to a conventional method, and N-hexyl-N-(β-cyanoethyl)-m
- Produced by coupling with toluidine. The λmax (acetone) of this product was 634 nm. Example 2 Structural formula below 0.5 g of a monoazo dye represented by is dispersed in water 3 containing 1.5 g of a naphthalene sulfonic acid-formaldehyde condensate and 1 g of higher alcohol sulfate ester, and a methylnaphthalene carrier is dispersed therein.
A dyeing bath was prepared by adding 15 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
It was produced by diazotizing -dinitro-thiophene according to a conventional method and coupling it with 3-acetylamino-N-hexyl-N-ethoxycarbonylmethylaniline. The λmax (acetone) of this product is 623n
It was m. Example 3 Structural formula below When polyester fibers were dyed using 0.5 g of the monoazo dye represented by the formula in the same manner as in Example 1, a polyester cloth dyed with good fastness and a clear 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-(β-heptyloxyethyl)-N-methoxycarbonylmethyl-m-toluidine. The λmax (acetone) of this product was 620 nm. Examples 4 to 18 When polyester fibers were dyed according to the method of Example 1 using the monoazo dyes shown in Table 1 below, dyed fabrics with the tones shown in Table 1 were obtained.

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Claims (1)

[Claims] 1. General formula (In the formula, R ¹ represents a C _5-8 alkyl group or a C _5-8 alkoxyethyl group, and R ² represents a cyano C _1-3 alkyl group, a C _1-4 alkoxycarbonylmethyl group, or
It represents a C _1-4 alkoxyethoxycarbonylmethyl group, and X represents a hydrogen atom, a methyl group, an acetylamino group or a chlorine atom. ) is a monoazo dye for synthetic fibers.