JPS6244584B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention has a 2,6-dicyano-4-nitrophenylazo moiety and an aniline coupler attached thereto, the coupler having an m-acylamido group and a polyether group attached to the aniline nitrogen.
Concerning blue dye. This dye has excellent properties including fastness and a highly desirable blue color in polyester and cellulose acetate fibers. The dye of the present invention is represented by the following formula. In the formula, R is an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or a linear or branched alkyl group having 1 to 4 carbon atoms (this alkyl group may be substituted with a phenoxy group or a phenyl group); R ₁ is a straight-chain or branched alkyl group having 1 to 6 carbon atoms; and R ₂ is a straight-chain or branched alkyl group having 1 to 4 carbon atoms. The dyes of the present invention have excellent dyeability by various methods, coating thickness, levelness, PH stability, fastness to light, washing and volatilization, color purity and color uniformity to light of various wavelengths, and virtually no blooming. It exhibits excellent properties such as color stability, uniformity of dyeing under various temperature and pressure conditions. Various examples of dyes of the invention are shown in Table 1. Particularly preferred dyes are compounds of the formula: Example 1 Production of 3′-{[2-(2-ethoxyethoxy)ethyl]-ethylamino}acetanilide 2- to m-acetamidoaniline (30.0 g)
(2-ethoxyethoxy)-ethanol (250ml)
and Raney nickel (25.0 g) were added. This mixture was autoclaved under nitrogen atmosphere.
It was heated at 200 psi and 175° C. for 12 hours and the Raney nickel was separated. Potassium carbonate (25.6
g) and iodized ethane (46.8g) were added and this was heated at 120°C for 3 hours. The reaction mixture was poured into water (800ml) and extracted with chloroform. Excess solvent was removed by distillation. The product was a brown viscous oil. The following couplers were prepared in the same manner as in Example 1. Example 2 3'{ethyl[2-(2-isobutoxyethoxy)ethyl]amino}benzanilide Example 3 3'-{[2-(2-ethoxyethoxy)ethyl]ethylamino}benzanilide Example 4 3'- {ethyl[2-(2-isopropoxyethoxy)ethyl]amino}acetanilide Example 5 3′-{[2-(2-methoxyethoxy)ethyl]ethylamino}benzanilide Example 6 3′-{[2-( 2-Butoxyethoxy)ethyl]ethylamino}acetanilide (2) Preparation of dye Sodium nitrate (7.2 g) was slowly added to concentrated sulfuric acid (50 ml). Cool the solution and add 100 ml of 1:5 acid (1 part propionic acid and 5 parts acetic acid).
It was added at a temperature below 15°C. Add 2,6 to this mixture
-dibromo-4-nitroaniline (29.6g: 0.1
mol) was then added to the above 1:5 acid (100 ml), both below 5°C. The reaction mixture was stirred at 0-5°C for 2 hours. The couplers of Examples 1-6 above (0.01 mol) were each separately dissolved in 40 ml of 1:5 acid and cooled to below 5°C. The above diazonium salt solution was added to each solution in an amount corresponding to 0.01 mol. This coupling mixture was allowed to stand for 1 hour. The dye was then precipitated by adding water. Collect this by filtration, wash with water,
Air dried. If necessary, the material was purified by slurrying in hot methanol, cooling, filtering, and washing with methanol. Examples 7-23 Replacement of odor atoms by cyano groups The respective brominated dyes corresponding to Examples 1-6 (0.002 mol), cyanide steel (0.4 g) and N,N
- Dimethylformamide (30ml) mixture at 95~
It was heated at 100°C for 30 minutes and poured into water. The resulting dicyano dye was recovered by filtration, washed with water and air dried. These cyano dyes are shown in Table 1. These exhibit a bright blue color for polyester fibers. Other dyes in Table 1 by similar production methods
13-23 was prepared.

[Table] Example 24 A dyeing test was conducted using the dye of Example 7 according to the following method. Dyeing method Dye 1.2% (% by weight based on the weight of fiber) Dispersant (condensation product of nactalene sulfonic acid and formaldehyde) 0.5g/oleyl-methyl-tauride sodium salt
Prepare a dye bath containing 0.5 g/2 g/ammonium sulfate. The pH of the above dyeing bath is adjusted to 4.0 using formic acid. The fiber and dyeing solution are used in a ratio of 1:20. Heat the dyeing bath to 70℃ and soak the polyester fibers. Raise the temperature to 130℃ over 30 minutes. Maintain this temperature for 60 minutes. The dye bath is then discarded and the fibers are thoroughly rinsed. The dyed fibers are treated with a reducing agent. Reduction: Hydrosulfite 1g/and caustic soda 3
This is followed by a thorough rinse in a bath containing g/(36°B′e). Results: The polyester fiber was dyed a beautiful blue color. Reference Example 1 Dyeing was carried out by the same dyeing method as in Example 24 using dyes of formulas (1) and (2) below. Results Polyester fibers were dyed a dark blue color with a green tint when the dye of formula (1) was used, and a dark blue color when the dye of formula (2) was used.

Claims (1)

[Claims] 1 formula [wherein R is selected from the group consisting of alkoxy having 1 to 4 carbon atoms; phenyl; and linear or branched alkyl having 1 to 4 carbon atoms which may be substituted with phenoxy and/or phenyl group, R ₁ is a straight-chain or branched alkyl having 1 to 6 carbon atoms, and R ₂ is a straight-chain or branched alkyl having 1 to 4 carbon atoms. 2 formulas The dicyanoazo dye according to claim 1, wherein R is a linear or branched alkyl having 1 to 4 carbon atoms. 3 formulas The dicyanoazo dye according to claim 1, characterized in that the dicyanoazo dye has: