JPS5996172A - Dis-azo dye for polyester fiber - Google Patents

Abstract

NEW MATERIAL:Dis-azo compounds of formula I wherein X is nitro, Cl; R<1>, R<2> are each a 1-4C alkyl, cyanoethyl, a 3-6C alkoxyethyl, a 4-5C alkanoyloxyethyl, alkoxycarbonylethyl, alkoxycarbonyloxyethyl. USE:Dyes for dip dyeing or printing polyester fibers, cotton, silk and wool with navy blue. PREPARATION:An amine of formula II is coupled with 2-amino-3-cyanothiophene. The resulting monoazo compd. of formula III is diazotized and coupled with a diphenylmethane compd. of formula IV.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a disazo dye for polyester fibers, and more specifically, it dyes polyester fibers in navy color and dyes the polyester fibers in various fastnesses, particularly light fastness, water fastness, and temperature stability during dyeing. The present invention relates to a disazo dye having excellent properties and pH stability, as well as excellent coupling yield and purity during production.

In JP-A-4/7J, the following compounds are described as dyes having a structure similar to that of the present invention.

Example-20 Comparing these with the present invention, the following table shows that the compound of the present invention has excellent light fastness, pH stability and temperature stability during dyeing, and resin processing. In terms of water fastness and washability, it is generally better than the compound of JP-A-1989/-¥7734.

*1 Light fastness: : From f 'L-θ? Goo de KM*
2 pH stability during dyeing = pH of the dye bath at 2% owf
= j, pH = 7, and compare and judge the degree of staining.

Dye for Otsuθ at ℃ and compare the degree of staining. Comparison judgment.

*4 Fastness after resin processing: After processing with a 7% water bath solution of polyurethane texture finishing agent, J-K5L-0 and 4 were tested with Otsu and AA'rOO [according to the law, determine the degree of nylon contamination.

*5 Build map property = 2% owi', 6% owf dyeing bath concentration /3θ℃ x 60 minutes and comparative judgment of dyeing degree.

The disazo dye for polyester fibers of the present invention has the following general formula [I] (wherein, X represents a nitro group or a chlorine atom, and R1
and R2 is an alkyl group with carbon atoms/~g, a cyanethyl group, an alkoxyethyl group with 3 to 2 carbon atoms, or a carbon atom number g~! an alkanoyloxyethyl group, an alkoxycarbonylethyl group, or an alkoxycarbonyl carbon represented by R1 and R2 in the general formula [I]? The alkyl group with six atoms/~Z is a methyl group,
Ethyl, propyl, and butyl groups are preferred; examples of alkoxyethyl groups having 3 to 3 carbon atoms include methoxyethyl, ethoxyethyl, propoxyethyl, and butoxyethyl groups; ! Examples of the alkanoyloxyethyl group include an acetoxyethyl group and a gropionyloxyethyl'' group, and examples of the alkoxycarbonylethyl group having a carbon atom number of ~! include a methoxycarbonylethyl group and an ethoxycarbonylethyl group. As the alkoxycarbonyloxyethyl group of ft, ~5, methoxycarbonyloxyethyl group and ethoxycarbonyloxyethyl group are mentioned.

The disazo dye represented by the above general formula [I] is represented by the following formula [■
] (In the formula, X is the same as the above definition.) The amines represented by the following formula [1fD] are diazotized and coupled with the λ-amino-3-cyanothiophene represented by the following formula [1fD] to obtain the following formula [IV] ( In the formula,
(2) It can be produced by coupling with a diphenylmethane compound represented by the formula (wherein R1 and R2 are the same as defined above).

Fibers that can be dyed with the disazo dye of the present invention include:
Polyester fibers such as polyethylene terephthalate, polycondensates of terephthalic acid and/or goobis-(hydroxymethyl)cyclohexane, or cotton, silk,
Examples include natural fibers such as wool; blends and blends of acetate fibers such as diacetate fibers and doria acetate fibers and the above polyester fibers.

To dye polyester fibers using the dye of the present invention, since the dye represented by the general formula [■] is insoluble or soluble in water, a conventional method is used to dye polyester fibers using naphthalene sulfonic acid and formaldehyde as a dispersant. Dyeing or printing may be carried out by preparing a dyeing bath or printing paste in which a condensate of ester, a higher alcohol sulfuric ester, and a higher alkylbenzene sulfonate are dispersed in an aqueous lA substance. For example, in the case of dip dyeing, polyester fibers or their blends can be dyed with excellent fastness by applying ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing. Alternatively, even better results can be obtained if, in some cases, acidic substances such as formic acid, acetic acid, phosphorous acid or ammonium sulfate are added to the dyeing bath.

Furthermore, the dye represented by the above-mentioned general formula [I] used in the method of the present invention may be used in combination with dyes of the same type or dyes of other systems. In some cases, good results such as improved dyeing properties can be obtained by incorporating the above.

Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples as long as the gist thereof is not exceeded.

Example/Polyester fiber 10θ1 was immersed in a dye bath in which dye O1!2 represented by the following structural formula was dispersed in 3 tons of water containing naphthalene sulfonic acid-formaldehyde Tsumugi Kinmono/2 and higher alcohol sulfate 22, and dyed at 730°C. After dyeing for 60 minutes, soaping, washing with water and drying were performed to obtain a navy dyed fabric. The light fastness, sublimation fastness, and water fastness of the dyed fabric obtained, as well as the temperature stability and pH stability of the dye during dyeing, were good.

The dye used in this example was produced as follows.

the law of nature? Sodium nitrite in 15% sulfuric acid at 30°C or less
4. Add -22, Otsu! The temperature was raised to ℃ and dissolved. 5~
Cool on ice to 70°C and add p-nitroaniline 3. j S'
was added at θ~30°C, and further heated to 300~3! The reaction was carried out at ℃ for 1 hour. Cool to 0-1℃ and add 0% sulfuric acid 7/6
F was added dropwise at 0 to 70°C. The obtained diazo liquid was added to 2 tons of hot water at θ°C, and sulfamine e-2,Of was added to remove excess nitrite. Then, separately, malonitrile/3-f fs p-cy5-an-
An aqueous dispersion containing 27.3 r of non-amino-3-cyanothiophene obtained from 2,j-diol/j,-2F was dropped into the diluted diazo liquid. At yo℃! After several hours of reaction, the precipitated monoazo compound was washed with water and dried, resulting in a monoazo compound (copmino-3-cyanoj-p-nitrophenyl azothiophene) represented by the following structural formula. Obtained.

Next, % similar awakening Kota! 7 Sodium nitrite/, Za 2
2 was added at 30°C or lower, and the temperature was raised to 65°C to dissolve it.

In the evening, cool to 70°C, add water//f and glacial acetic acid! 2 to 0
Add at 1°C and monoazo compound (-2-amino-3-cyano-5-p-nitrophenylazothiophene) J-J
46fQ was added at −3 to θ° C., and reacted at the same temperature for 2 hours to prepare a diazo solution W15.

On the other hand, add N-ethyl-N-cyanoethylaniline to a solution of 2.262% sulfuric acid and 2F% at room temperature. ,,22 f
Add and dissolve formaldehyde water bath solution/, 3g2
was added and reacted at J-℃ for a period of time to form a diphenylmethane compound represented by the following structural formula /θ, ? An aqueous solution containing 2 was obtained. Add water, θ- and urea to this solution /, /2
Add Surf Inol/θ4tFi/drop, Ice/2Q2
was added, and the diazo solution prepared earlier was added dropwise. After stirring at 0 to 1°C for 5 hours, the mixture was filtered, washed with water, and dried to obtain a disazo compound 6.tata represented by the following formula (4).

The λmax (acetone) of this product is 63! It was nm.

Example λ A dyeing bath was prepared by dispersing dye O1!2 represented by the following structural formula in 3 t of water containing naphthalene sulfonic acid-formaldehyde metallurgy/1 and higher alcohol sulfate ester=22. Polyester fiber/θ0g was immersed in this dyeing bath, and
After coloring at 30° C. for θ minutes, the fabric was washed pink, washed with water, and dried to obtain a navy-colored dyed fabric.

The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced according to Example/.

The λmax (acetone) of this product was 6 nm.

Example A dyeing bath was prepared by dispersing 0.57 of a dye represented by the following structural formula in 3 tons of water containing naphthalene sulfonic acid-formaldehyde Kanamono/2 and higher alcohol sulfate ester λ2.

Immerse 1ooy of polyester fibers in this dyeing bath,
After imaging for 60 minutes at 0°C, the fabric was washed pink, washed with water, and dried, resulting in a navy dyed fabric.

The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced according to Example/.

Motoichi's λmax (acetone) was 6 O/nm.

Examples include dyes θ represented by the following structural formula! A dyeing bath was prepared by dispersing 2 in 3 parts of water containing naphthalene sulfonic acid-formaldehyde condensate/2 and higher alcohol sulfate 22.

Polyester fiber 1001 is immersed in this dyeing bath,
After dyeing at 0° C. for 6θ minutes, the fabric was washed pink, washed with water, and dried to obtain a navy dyed fabric.

The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced according to Example/.

Motoichi's λmax (acetone) was 623°Cm.

Example! A dye bath was prepared by dispersing the dye represented by the following structural formula (0. /θθ was immersed and dyed at 730° C. for 6Q minutes, then washed pink, washed with water, and dried to obtain a navy-colored dyed fabric.

The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced according to Example/.

Motoichi's λmax (acetone) is 63? It was nm.

Example B Dye represented by the following structural formula θ,! A dye bath was prepared by dispersing 2 in water containing naphthalene sulfonic acid-formaldehyde condensate/7 and higher alcohol sulfate 2.

Polyester fiber 1001 is immersed in this dyeing bath,
After dyeing at 0° C. for 6θ minutes, the fabric was washed pink, washed with water, and dried to obtain a navy dyed fabric.

The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced according to Example/.

Motoichi's λmax (acetone) was 31 nm.

Example 2 A dyeing bath was prepared by dispersing dye O6!1 represented by the following formula in 3 tons of water containing naphthalene sulfonic acid-formaldehyde condensate/2 and higher alcohol sulfate ester 27.

Polyester fiber/θθf was immersed in this dyeing bath, and 73
After dyeing at 0° C. for 6θ minutes, the fabric was washed pink, washed with water, and dried to obtain a navy dyed fabric.

The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced according to Example/.

Motoichi's λmax (acetone) was Otsuyo-nm.

Example 1 Polyester fibers were dyed using the dyes shown in the table below in the same manner as in Example 1 to obtain dyed products having the colors shown in the table.

Claims (1)

[Claims] (1) General formula (wherein, (Representing an alkanoyloxyethyl group, an alkoxycarbonylethyl group, or an alkoxycarbonyloxyethyl group at the edges.) A disazo dye for polyester fibers.