JPS6136363A - Pyrazolone based monoazo dye - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (X is phenoxyethyl or benzyl; R is alkenyl or allyloxyalkyl). EXAMPLE:A compound expressed by formula II. USE:Useful for dyeing polyester fibers, etc., having improved alkali resist printing property, effective for preventing damage of alkali-resistant dye and deterioration in strength of the polyester fibers, etc. and having improved various fastnesses and dyeing characteristics. PREPARATION:For example, a compound expressed by formula III is diazotized and coupled with a pyrazolone expressed by formula IV.

Description

[Detailed description of the invention] Industrial applications Concerning monoazo dyes.

Recently, as a new dyeing process for polyester fibers, alkali-resistant discharge printing has become popular. The principle of alkaline resist-discharge printing is to hydrolyze the dye with an alkali and cause it to lose its affinity for polyester fibers.It is a processing method that resists or discharges specific parts of fibers or dyed fabrics.

Conventional technology Conventionally, dyes with relatively good alkali discharge resistance were used at °C and the following dyes (%Kasho 3'/-'7946/,
JP-A-39-33! ;! r, Publication No. 3, JP-A-5Q-Q
IIS, Y Publication) is known.

Problems to be Solved by the Invention As mentioned above, in the alkali-proof discharge printing process, the alkali-discharge-proof property has recently been improved, the discharge-proof printing of ground-dyed fabrics is good, and the amount of alkali agents and solubilizing discharge printing accelerators used is small. There is a need for dyes that can be used in a variety of ways. Reducing the amount of alkaline agents and discharge aids can prevent damage to the alkali-resistant dyes (insert colors) used during color discharge printing, and can also prevent the strength of polyester fabric from decreasing due to alkali. benefits arise.

Although the conventional dyes described above have achieved considerable improvement in wet fastness, the reality is that sufficient whiteness cannot be obtained when removing with an extremely small amount of alkaline agent. eThe dye of the present invention achieves sufficient discharge resistance with the use of an extremely small amount of alkaline agent, is effective in preventing damage to inset colors and loss of strength of polyester fibers, etc., and improves various fastnesses and dyeing properties. The purpose of this invention is to provide a monoazo dye with excellent characteristic pressure and high practical value.

Means for solving the problems, that is, the present invention provides a compound represented by the general formula [I] (wherein, X represents a phenoxyethyl group or a benzyl group, and R represents an alkenyl group or an allyloxyalkyl group) Its gist is pyrazolone monoazo dyes.

Examples of the alkenyl group represented by R include an allyl group, a butynyl group, a crotyl group, and the like.

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

A compound represented by the following general formula [I] (wherein, X is the same as defined above) is converted into gold diazotization, and coupled with a pyrazolone represented by the following general formula [1] (wherein, R is the same as defined above) Manufactured by SakotoK.

Fibers that can be dyed with the monoazo dye of the present invention include polyethylene terephthalate, terephthalic acid and/or 4
(Polyester fiber made of polycondensed metal with -bis-(hydroxymethyl)cyclohexane, or cotton,
Examples include blended products and mixed fiber products (cloth, woven and knitted fabrics, etc.) of natural fibers such as silk and wool and the above-mentioned polyester fibers.

When dyeing is carried out using the dye of the present invention, the dye represented by the general formula (1) is dispersed in an all-aqueous medium using a dispersant, and then applied to a dye bath or printing paste. For example, when dyeing is performed, ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing are applied. It is possible to dye blended textiles and mixed fiber products with excellent fastness.

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

In addition, when performing alkaline resist discharge printing using the dye of the present invention, a polyester cloth or the like is immersed in the dyeing bath prepared above and dyed at %t, yoc for 60 minutes. After drying at 50-150°C, the cloth etc. was ground-dyed, and then the obtained cloth was printed with the alkaline anti-discharge dyeing paste and dried at 100°C for 2-3 minutes. After, 1
Apply heat treatment at 10°C for 7 minutes to fix the dye in the background dyed area and decompose the dye in the anti-discharge dyed area printed with anti-discharge dyeing paste, then wash with water, reduce wash, wash with water and dry. From K, it is possible to obtain cloth etc. that have been subjected to alkali discharge-proof printing.

Alkali discharge printing resistance is evaluated by measuring the white discoloration of the alkali discharge resistant discharge dyed area of cloth etc. that has been subjected to alkali discharge printing using a gray school. It was excellent.

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 dyeing property, build-up property and temperature dependence, and also has excellent light fastness and sublimation resistance. It has excellent fastness properties such as fastness, fastness to washing, fastness to sweat, and fastness to water. Functions and Effects The dye of the present invention is structurally very similar to conventional known dyes. Nevertheless, by introducing an alkenyl group or an allyloxyalkyl group into the carboxylic acid ester group of the pyrazolone skeleton, extremely good alkali dischargeability can be achieved compared to conventional alkyl groups, as shown in the table below. It is something. Furthermore, the dye of the present invention has good white-out property, even when a small amount of weak alkaline agents such as sodium bicarbonate and sodium dihydrogen phosphate are used, with which known dyes are hardly discharged. It is considered to be a valuable dye that enables heavy alkali discharge printing when used in combination with a dye that achieves white removal only in the presence of a strong alkali.

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 all examples, but the present invention is not limited to the following examples.

Example 1 A dyeing bath was prepared by dispersing 0.3 tk of the monoazo dye represented by the structural formula, 3 tk of water containing the naphthalene sulfonic acid-formaldehyde condensate, and 3 tk of water containing the higher alcohol sulfate ester and otk. Add polyester cloth to this dye bath / 0
0 ff: After dipping and dyeing at 130°C for 60 minutes, washing with water and drying, a yellow dyed polyester cloth with good light fastness, sublimation fastness and 1nlV4 fastness was obtained. Ta.

1. When the alkali discharge printing resistance was measured using the above monoazo dye, it showed excellent properties as shown in Table 1.

Dye L used in this example was produced as follows. Kufuenoxyethoxy7carponylanilinyus, ttt
Sodium nitrite? ,? ii-'i containing ice water ioog-
Diazo solution 1 was prepared by dropping the resulting dispersion into 24 tOPK of a 70% by weight aqueous hydrochloric acid solution. Sodium carbonate/J, Ri 1 was dissolved in 1,300 mL of water, and the resulting solution was dissolved with /-phenyl- The entire coupling solution was prepared by adding 3-allyloxycarbonylpyrazolone x + yv, and the above diazo solution r (dropwise added at below io°C, the precipitated crystals were obtained by door to door and drying (relative to theoretical yield λ%), Maximum absorption wavelength of crystal λnmg (acetone)
was Hiromu/3 nm @ dye shown in Example 0. ! ;ff was mixed with naphthalene sulfonic acid-holoformaldehyde condensate Off and pulverized in a paint shaker to obtain a finely divided dye. Then,
The obtained micronized dye and element ii/I consisting of the following composition
The mixture was thoroughly mixed to obtain a colored paste.

Composition of base glue Carboquine methylcellulose 1M agent, 7 o, o y
Tartaric acid Ol-? Total Tata, OP The obtained color paste was printed on polyester fiber, and it was dried for 10 minutes, then held in superheated steam at medium pressure at 170°C for 7 minutes to develop color, and then washed, washed with water, and dried. As a result, a yellow dyed fabric with excellent light fastness, sublimation fastness and wet fastness was obtained.

In addition, all of the above monoazo dyes are used, sodium carbonate O,
When the alkaline discharge printing resistance was measured at a low concentration of S%, it showed excellent properties as shown in the table below. Note that alkaline discharge resistance is usually measured by sodium carbonate S%, but in this case 0.5% gold was used. In other words, a dye that exhibits good alkali discharge resistance under these conditions is said to be a dye that exhibits effective discharge resistance with a small amount of alkaline agent.

The ingredient used in this example was produced in the same manner as in the example. Obtained maximum absorption wavelength λrnax of Sakae
(acetone) was 4'/3 nm.

Comparative example 1. and 3 Using the dyes listed in Table 1 below, the alkaline discharge printing resistance was measured and the results are shown in Table 1. Alkali discharge printing el 1
tl11 standard method Dyeing with n'E dye in advance (130℃ x 40 minutes)
A discharge paste containing sodium carbonate O, STS, 10 parts of polyethylene glycol based 9M rule, and 3 parts of carrier was applied to the dyed cloth K, treated in superheated steam for 7 minutes at 0°C, and then subjected to reduction cleaning. The white discoloration of the discharge-printed area of the dyed fabric obtained was determined using a stain play scale.

Example 3 Polyester 4Affl was dyed in accordance with the method of Example 1 using the following surface pressure water monoazo dye, and the resulting dyed fabric was measured in the same manner as in Example 1. It is shown in Table 1.

Table λ

Claims (1)

[Claims] (1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] (In the formula, X represents a phenoxyethyl group or a benzyl group, and R represents an alkenyl group or an allyloxyalkyl group) Pyrazolone yarn monoazo dye.