JPS61106669A - Monoazo dye - Google Patents

Abstract

NEW MATERIAL:Monoazo compounds of formula I wherein A is a group of formula I or II; R is alkyl, alkyloxyalkyl, alkyloxyalkyl, phenyloxyalkyl, benzyl; R' is H, alkyl, allyloxyalkyl, alkyloxyalkyl, phenyloxyalkyl, benzyl, cyanomethyl, allyloxycarbonylmethyl, etc.; the sum of carbon atoms of R and R' is 6-16. USE:Dyes which dye mixed fabrics and fiber blends of polyester fibers with natural fibers such as cotton, silk and wool yellow. They can achieve sufficient resist-printability and dischargeability by the use of a small quantity of an alkali, have an excellent effect of preventing fiber strength from being lowered and are excellent in fastness and dyeability. PREPARATION:A compd. of formula IV is diazotized and then coupled with a coupling component of the formula H-A to obtain the desired compd.

Description

[Detailed description of the invention] Industrial applications The present invention relates to monoazo dyes.

Specifically, the present invention relates to a monoazo dye having excellent alkali discharge printing resistance.

Recently, as a new dyeing process for polyester fibers, alkali-resistant discharge printing has become popular. The principle of alkaline resist-discharge printing is a processing method in which dyes are hydrolyzed with alkali and lose their affinity for polyester fibers, thereby resist-printing or discharging multi-fibers or specific parts of dyed fabrics.

Conventional technology Conventionally, the following dyes have been used as dyes having relatively good alkaline discharge printing resistance (Special Publication Sho g!-197/6 Car 197 Public Sho, T?-35934 Publication and British Patent No. 201011).
Publication No. g) is known.

Problems to be Solved by the Invention In the above-mentioned alkali casting discharge dyeing process, %Kfi improves the alkali discharge dyeing resistance and improves the casting resistance of ground-dyed fabric [i'1 Sea bream "0t" F capital 9.7"'4・For 91, a dye that requires only a small amount of 871 agent is desired.

Reducing the amount of alkaline agents and discharge aids prevents damage to the alkali-resistant dyes (insert colors) used for color discharge printing, and also prevents the strength of polyester fabric from decreasing due to alkali. benefits arise.

However, on the other hand, dyes with increased affinity for alkaline agents (for example, the conventional dyes described above) are inferior in wet fastness such as washing resistance, sweat resistance, and water fastness, as well as heat resistance. There was a drawback.

The object of the present invention is to provide a dye that has good alkali discharge printing resistance and also good wet fastness and heat resistance, that is, to provide an alkaline discharge printing dye that solves the contradictory principles.

The present invention achieves sufficient casting and discharge printability with the use of a small amount of alkaline agent, is effective in preventing damage to ink colors and strength reduction of polyester fibers, etc., and has excellent fastness and dyeing properties. The purpose is to provide a high b monoazo dye of practical value.゛Means for Solving the Problems The present invention is directed to the general formula [13 (wherein, R represents an alkyl group, an allyloxyalkyl group,
Alkyl represents a dialkyl group, a phenyloxyalkyl group, or a benzyl group, and π is a hydrogen atom, an alkyl group, an allyloxyalkyl group, an alkyloxyalkyl group, a phenyloxyalkyl group, a benzyl group, a cyanomethyl group, an allyloxycarbonyl group. A methyl group, an alkoxycarbonylmethyl group, a phenyloxyalkyl tertiary carbonylmethyl group, or a benzyloxycarbonylmethyl group.

The gist thereof is a monoazo dye represented by R and R' having a total number of carbon atoms of 6 to 16.

- In the above general formula CI), the alkyl groups represented by R and y may be linear or branched, and R and y may be linear or branched.
The total number of carbon atoms is preferably 1-/co. R'
is preferably a hydrogen atom.

0+-4,7ru # Rug or a, -C, Alkyluo #
ShiO,,C.

an alkyl group, in which case R is aIAc4.alkyl group, allyloxyenal group ka, 04 alkyloxyethyl group, phenyloxyethyl group, or benzyl group, and the sum of the R prime numbers of R and R' is g Particular preference is given to selecting a combination of ~l.

The monoazo dye represented by the general formula [1] can be produced, for example, as follows.

A compound represented by the following general formula [11] (wherein R is the same as defined in the above general formula [1)] is diazotized, and the coupling component is the following general formula (1) H-A.
...... (1) (wherein A is the general formula CII
F)H is formed by coupling with (same as the definition in ).

Fibers that can be dyed with the monoazo dye of the present invention include polyethylene terephthalate, terephthal [/l<'
- Other polyester fibers such as polycondensates of bissu (hydroxymethyl cocyclo) and beef san, or blends and blends of natural fibers such as cotton, silk, and wool with the above polyester fibers (cloth, woven and knitted fabrics, etc.) ].

When carrying out dyeing using the dye of the present invention, a dye bath or printing paste is prepared by dispersing the dye represented by the general formula C1) in an aqueous medium using a dispersant in a conventional manner. , dyeing or printing.

, 11 ′″&-, f-“・ Dyeing 1 row 7′ place 4!
``'' - By applying ordinary dyeing methods such as high 1 dyeing method, carrier dyeing method, thermosol dyeing method, etc., polyester fibers or their blended products and mixed fiber products can be dyed with excellent fastness. be able to.

Further, in some cases, even better results may be obtained by adding an acidic substance to the dyeing bath.

In addition, when carrying out alkaline anti-discharge printing using the dye of the present invention, polyester cloth etc. is immersed in the dyeing bath prepared above and dyed at 730°C for 10 minutes.
By drying at a temperature of 0 to 110°C, fabrics, etc., can be ground dyed.

Next, an alkaline anti-discharge dyeing paste is printed on the obtained cloth, etc., and i
After drying at oo°C for 2-3 minutes.

Heat treatment at 0°C for 7 minutes fixes the dye in the dyed area and decomposes the dye in the part of the casting where the anti-discharge dyeing paste is printed, followed by washing with water, reduction washing, washing with water and drying. By carrying out this process, it is possible to obtain dialkali-resistant discharge dyed cloth.

The monoazo dye of the present invention may be used in combination with dyes of the same type or dyes of other types.

Examples - 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.

Example 1 n-butoxyethyl guamino-J-nitrobenzoate!
, 6 g is diazotized with dacotinitrosyl sulfate in phosphoric acid:acetic acid=/:/solvent 30111 at 0° C. for 7 hours.

N-Ethyl-J-cyano-q-methyl-6-hydrobylcypyridone, 4.9, in sodium acetate S, -
21 Sodium hydroxide was dissolved in 4100 ml of water, diazo solution was added at θ ~ 3°C and pH 4cmj, and the mixture was stirred for 3 hours.
After drying, a monoazo dye represented by the following structural formula was obtained (yield: 91 cm).

The maximum absorption wavelength of the obtained monoazo dye is λm&! (Acetone was 1 nm.

A dyeing bath was prepared by dispersing a sulfonic acid-formaldehyde condensate of the structural formula O1 and a higher alcohol sulfate ester in water 3) containing O1. 1 ool of polyester cloth was immersed in this dyeing bath.

After dyeing at 130° C. for 60 minutes, and after death, soaping, washing with water, and drying, a yellow-dyed polyester cloth with good light fastness, sublimation fastness, and wet fastness was obtained. Furthermore, when the above monoazo dye was used to measure alkali discharge printing resistance, various wet fastnesses, and heat resistance, it showed excellent properties as shown in Table 1.

The dyes o and ri shown in Example 1 were mixed with the 7-talenesulfonic acid-formaldehyde condensate o and sy, and the mixture was pulverized in a paint shaker to obtain a finely divided dye. Next, the resulting finely divided dye and a base paste having the composition shown below were thoroughly mixed to obtain a colored paste.

Composition strength of original glue
The obtained color paste was printed on polyester fiber, and
After intermediate drying at 170°C, the color was developed by holding it in superheated steam at 170°C for 7 minutes, then annealing, washing with water, and drying. A dyed fabric with excellent yellow color was obtained.

In addition, using the above monoazo dye, sodium carbonate θ,
When the alkaline discharge dyeing resistance was measured at a low concentration, it showed excellent properties as shown in Table 1 below. Note that alkaline discharge printing resistance is usually measured using sodium carbonate sq6, but in this case, 0.2 sq was used. In other words, a dye that shows good results in alkali discharge printing resistance under these conditions can be said to be a dye that shows effective casting and discharge printing property with a small amount of alkaline agent.

The dye used in this example was produced in the same manner as in Example. The maximum absorption wavelength λmaw (acetone) of the obtained friend dye was gQonm.

Comparative Examples 7 to 4 Using the dyes listed in Table 7 below, alkali cast discharge printability, various wet sluggishness degrees, and heat resistance were measured according to the following measurement methods, and the results are shown in Table 1.

Measurement method: (1) Alkaline discharge printing property A discharge printing paste containing soda carbonate and polyethylene glycol (average molecular weight 0θ) was applied to a dyed cloth that had been previously dyed with the dye, and then treated in superheated steam at a temperature of 10°C for 7 minutes. After that, the discharged portion of the dyed fabric obtained by reduction cleaning is
゛White discoloration was determined using a gray scale for contamination.

(2) Polyurethane processing method Hydra 7F-Koda K (7)/140 using $8 liquid
Cure for 1 minute at °C.

(3) Washing fastness A multi-fiber was attached to a dyed cloth treated with polyurethane, and a washing test was conducted according to AATOO washing method No. IA, and contamination of the nylon fibers of the multi-fiber was determined using a clay scale.

(4) Sweat fastness Dyed fabric treated with polyurethane J-Kog SL-ogQr
Tests were conducted in accordance with method h, except that nylon cloth and silk cloth were used as the attached cloths, and the degree of contamination of the silk cloths was determined on a gray scale.

(5J Water fastness: Dyed cloth treated with polyurethane: JXB L-oz
A dip test was conducted according to the 41bA method except that silk cloth was attached instead of nylon cloth, and the degree of contamination of the silk cloth was determined on a gray scale.

(6) The heat-resistant dye cake was mixed with a naphthalene sulfonic acid-formaldehyde condensate and heat-treated at %/JO''Ci for 1 hour, and then the residual rate of the dye was determined.

Examples J-fJ Using the monoazo dyes shown in Tables 2 and 3 below, polyester fibers were dyed according to the method of Example 1, and the obtained dyed fabrics were subjected to the same measurements as in Example/. . The results obtained are shown in Tables 1 and 3.

effect The cloth etc. had excellent alkali discharge printing resistance.

Furthermore, the dyed fabric obtained by the above-mentioned dip dyeing or printing using the dye of the present invention has excellent properties during dyeing such as dyeability, build-up property, and temperature dependence. It has excellent durability such as fastness, washing resistance, sweat resistance, and water resistance.

(1 other person)

Claims (1)

[Claims] (1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・[I] ▼ represents an alkyl group, an allyloxyalkyl group,
represents an alkyloxyalkyl group, a phenyloxyalkyl group, or a benzyl group, and R' is a hydrogen atom, an alkyl group, an allyloxyalkyl group, an alkyloxyalkyl group, a phenyloxyalkyl group, a benzyl group, a cyanomethyl group, an allyloxy A monoazo dye representing a carbonylmethyl group, an alkoxycarbonylmethyl group, a phenyloxyalkyloxycarbonylmethyl group, or a benzyloxycarbonylmethyl group, and in which the total number of carbon atoms of R and R' is 6 to 16.