JPS6088074A - Monoazo dye for synthetic fiber - Google Patents

Abstract

NEW MATERIAL:Compounds of formula I wherein R<1> is alkyl, aralkyl, aryl, allyl, alkoxyalkyl, beta-phenoxyethyl, tetrahydrofurfuryl, beta-allyloxyethyl; R<2> is methyl, ethyl, propyl, butyl, -CH2COOR (wherein R is methyl, ethyl). USE:Monoazo dyes which dye polyester fibers clear yellow with excellent alkaline dischargeability and fastness to light and sublimation. PREPARATION:A P-aminobenzoate of formula II is diazotized with NaNO2 in an aq. hydrochloric acid soln. The resulting diazonium salt is coupled with a pyrazolone of formula III. Alternatively, a monoazo compd. of formula IV is reacted with a compd. of formula V (wherein X' is Cl, Br, I) in the presence of a dechlorinating agent such as soda ash or MgO.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to monoazo dyes for synthetic fibers. More specifically, the present invention relates to a monoazo dye that can dye synthetic fibers W, especially polyester fibers, in a strong and vivid yellow color, and that exhibits excellent white discoloration when subjected to alkaline discharge printing using an alkaline agent.

The dye according to the present invention has the following general formula (I): β-
It represents an allyloxyethyl group, and R' is a methyl group, an ethyl group, a propyl group, a butyl group, or -CH,SOR (herein, R represents a methyl group or an ethyl group). ] A water-insoluble monoazo dye represented by the above general formula (I), for example, in the following general formula (2), R1 is R' in the above general formula (I). represent the same meaning. ] Obtained by diazotizing the esters of P-ami7benzoic acid represented by the formula with sodium nitrite in hydrochloric acid water [Formula Tsukuda]
R' in the formula has the same meaning as po in the general formula (I). ] Coupling with a pyrazolone represented by [Formula 叡)] R'' has the same meaning as R' in the above general formula (I).] Coupling the monoazo compound represented by soda ash, magnesium oxide, etc. In the presence of a deoxidizing agent, general formula M , 9 .

X-CH,COR(V') [R' in 2M represents the same meaning as in the above general formula fI), and X'' can be produced by a chlorine atom, a bromine atom or an iodine atom.

The yellow dye of the present invention represented by the general formula (Il) is a new disperse dye, and is characterized by excellent alkali discharge printability and various fastnesses, particularly light fastness and sublimation fastness.

As the dye having a structure similar to the dye of the present invention, [wherein R is an alkyl group, an alkenyl group, an oxyalkyl group,
It represents an alkoxyalkyl group or a halogenalkyl group, and Fff means an alkyl group. ] are disclosed, and specific examples thereof include compounds such as:

However, according to the test results of the present inventors, as shown in the table below, the above-mentioned dye No. 5456/1986 has a major drawback of extremely poor E color fastness and high in-machine sublimation during high-temperature steaming. was there.

In addition, as a dye with improved sublimation fastness of the dye of JP-A-43-5456, JP-A-57-49661 [wherein Y and Z each independently represent a hydrogen atom, a chlorine atom, or a bromine atom, and R represents a lower alkyl group. ] and other dyes are described.

However, test results using these dyes show that although the sublimation fastness is improved due to the introduction of tetrahydrofurfuryl and benzyl groups, the alkali discharge performance is poor.
It shows a tendency to be inferior to the dye described in Publication No. 3-5456, and can hardly be used as a dye for alkal discharge printing, which has recently begun to be used frequently as a new discharge printing method.

Therefore, the present inventors conducted intensive studies to develop a dye that has both good alkali discharge printability and high sublimation fastness, and found that the dye represented by formula (I) has good alkali discharge printability and high sublimation fastness. It was discovered that the dye has extremely good properties.

The test results are shown in the table below, and it is clear that the dye of the present invention is far superior to known dyes in both alkali discharge printability and sublimation fastness.

(Yaichigo Sonobu (Note-1) Special Publication Showa 43-5456 Dye of Example 1 (
Note-2) JP-A-43-5456 Dye of Example 1-4 (Note-3) JP-A-57-49661 Dye of Example 1 (Note-4) JP-A-57-49661 Heat of dye of Example 2 I did the set processing.

The dye of the present invention is characterized by improved sublimation fastness and improved alkali discharge dyeing property due to the specified coupler component, and it has been found that a well-balanced disperse dye can be obtained, and the present invention has been achieved. It is. In the dye of the present invention, the alkyl group represented by R''-C in the general formula (I) includes a methyl group, an ethyl group, an n-propyl group,
1so-propyl group, linear or branched butyl group,
Examples include pentyl group, hexyl group, heptyl group and octyl group, examples of aralkyl group include benzyl group and phenethyl group, and examples of aryl group include phenyl group, halogen-substituted phenyl group, alkyl-substituted phenyl group and alkoxy-substituted phenyl group. Examples of the alkoxyalkyl group include β-methoxyethyl group, β-ethoxyethyl group, linear or branched β-propoxyethyl group, β-butoxyethyl group, t-methoxybutyl group, etc. can be mentioned.

In order to dye synthetic fibers with the dye of the present invention, the dye represented by the general formula (I) can be dyed with a condensate of naphthalene sulfonic acid and formaldehyde, a higher alcohol sulfate ester, a higher alkylbenzene sulfone salt, etc. by a conventional method. Dyeing or printing may be carried out by dispersing in an aqueous medium to prepare a dyeing bath or printing paste using a dispersant such as the following. For example, when dyeing is performed, synthetic fibers can be dyed with excellent fastness by applying common dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing.

In addition, as a method for discharging this dyed product using an alkaline agent, printing is performed using an alkaline agent such as soda ash or 11 kpotassium charcoal, and if necessary, a discharge printing paste containing a disperse dye that is stable to the alkaline agent. By performing teaming or high-pressure steaming, it is possible to obtain a dyed product with a discharge printing pattern having a clear pattern.

In addition, as a method for performing alkaline resist dyeing using an alkaline agent, for example, an alkaline agent such as soda ash or potassium carbonate is applied to a synthetic fiber cloth, and if necessary, a discharge printing paste containing a disperse dye that is stable to the alkaline agent is applied to the pattern. After printing, it is dried until dry, and then a color paste containing a monoazo dye represented by the general formula (I) is printed on it. Thereafter, dyeing is performed using a conventional high-temperature steaming method or high-pressure steaming method to obtain a dyed cloth with a clear pattern.

Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the Examples unless the gist thereof is exceeded.

(41-Q) [Example 1] A dyeing bath was prepared by dispersing 0.5 g of the monoazo dye shown in Example 1 in 31 parts of water containing 1 g of naphthalene sulfonic acid-formaldehyde condensate and 2 g of higher alcohol sulfate ester.

Immerse 100g of polyester Takeo in this dyeing bath,
After dyeing at 30° C. for 30 minutes, soaping, washing with water, and drying were performed, a bright yellow dyed product with excellent light fastness, sublimation fastness, and water fastness t] was obtained.

The light fastness of this dyed fabric is grade 7, and the sublimation fastness is 4-4.
5 edges, water fastness was grade 5.

In addition, 5 parts of soda ash, 5 parts of polyethylene glycol, and 7 parts of locust bean gum paste were added to the dyed cloth obtained as described above.
An alkaline discharging paste consisting of 3 parts and 83 parts of water is printed in the shape of a flower pattern, steamed in a high-temperature steamer at 175°C for 6 minutes, and then reduced and washed to obtain a dyed product with excellent white discoloration in the flower pattern. Ta.

The dye used in this example was a monoazo compound 3 of the following formula.
After dissolving 8 g in 85 parts of dimethylformamide, 15 g of potassium carbonate and 2 g of potassium iodide were added, followed by addition of monochloroacetic acid ethyl ester 16J9, and the reaction was carried out at 60°C for 2 hours. The reaction solution was poured into 500 d of water to precipitate. Obtained by splitting the crystal.

Input max (in acetone) = 410 nm [Example 2] Monoazo dye Q, 5.9, represented by the following structural formula was added to water 31 containing 1.5 g of naphthalene sulfonic acid-formaldehyde condensate and 1 g of higher alcohol sulfate ester. disperse,
Methylnaphthalene carrier 151 was added to this to prepare a dyeing bath.

Dip the polyester fiber cloth tnoy in this dyeing bath,
After dyeing at 00°C for 90 minutes, soaping, washing with water and drying, the polyester fabric was dyed a strong and vivid yellow color with a light fastness of class 7, a sublimation fastness of class 5, and a water fastness of class 5. was gotten.

The dye used in this example was prepared by diazotizing P-ami7benzoic acid (benzyloxycarbonylmethyl) ester with sodium nitrite in an aqueous hydrochloric acid solution and coupling it with 1-phenyl-3-butoxycarbonyl-5-pyrazolone. Obtained.

max. (in acetone) 412 nm [Example 3] 3 parts of a monoazo dye shown by the following formula, 3 parts of Demol N (Kao Atlas product), and 4 parts of water were mixed and atomized to obtain a liquid dye composition. Part 3, Maypro Gum NP (
A color paste consisting of 60 parts of a 12% aqueous solution, 5 parts of sodium chlorate, and 36.5 parts of water was printed on a Tetron-treated thread cloth. After intermediate drying at 80°C, an alkaline resist dyeing paste consisting of 5 parts of soda carbonate, 7 parts of glycerin, 7 parts of polyethylene glycol, 55 parts of Maybrogum NP12 aqueous solution and 26 parts of water was printed on the intermediate dry cloth.
After intermediate drying at 0°C, it was steamed with high temperature steam at 175°C for 5 minutes.

Subsequently, by washing with water and reduction washing, a yellow dyed product with excellent white discoloration in the discharge-printed area was obtained.

The dye used in this example was P-ami7benzoic f9 ((
[beta]-ethoxyethyl)oxycarbonylmethyl] ester was diazotized with sodium nitrite in an aqueous hydrochloric acid solution and coupled with 1-phenyl-3-methoxycarbonyl-5-pyrazolone.

Input max (in acetone) = 409 nm [Examples 4-1
1] Polyester fibers were dyed using the monoazo dye shown in the following formula according to the method of Example 111, and the dyed fabric strength τ of the color tone shown in the following table was obtained.

general formula

Claims (1)

[Scope of Claims] [In the formula, W represents an alkyl group, an aralkyl group, an aryl group, an allyl group, an alkoxyalkyl group, a β-phenoxyethyl group, a tetrahydrofurfuryl group, or a β-allyloxyethyl group; It is a methyl group, an ethyl group, a propyl group, a butyl group, or -CH, C00R (R represents a methyl or an ethyl group). ] Monoazo dye for synthetic fibers shown by