JPH0742415B2 - Water-soluble formazan dye - Google Patents

Description

TECHNICAL FIELD The present invention relates to a blue water-soluble formazan dye having a novel structure, and more specifically, when used for dyeing cellulose fibers or nitrogen-containing fibers, various fast dyes are used. The present invention relates to a water-soluble formazan dye excellent in reaction fixability and build-up property.

[Prior art]

Water-soluble reactive dyes are usually used for dyeing cellulose fibers or nitrogen-containing fibers, and various dyes having excellent fastness and various dyeing properties have been conventionally proposed.
Of these, copper formazan-based reactive dyes are generally noted for their excellent light fastness and fastness to sweat and sunlight. For example, reactive dyes having the following structural formulas are known.
(See JP-A-60-258,266) However, in the case of this dye, although the light fastness and the like are excellent, it was slightly insufficient in terms of reaction fixing property to fibers and build-up property. Further, in recent years, from the viewpoint of economy as a dyeing temperature, a dye exhibiting optimum dyeing property in a low temperature range of 50 to 60 ° C. has been demanded, but the above-mentioned known dyes cannot be said to be sufficient also from this point.

[Problems to be solved by the invention]

In view of the above circumstances, the present inventors maintain the characteristics of the known copper formazan-based reactive dyes that various fastnesses are good, while exhibiting excellent reaction fixing properties and build-up properties, and
As a result of various studies to obtain a reactive dye that can be dyed well even in a low temperature range, by introducing an alkenyloxy group into the triazine ring of a known copper formazan reactive dye, a comprehensively excellent reactive dye aimed at by the present invention. The present invention was completed by finding out that

[Means for solving problems]

The gist of the present invention is the following general formula [I] in the form of a free acid. [In the formula, R represents an alkenyl group which may be substituted with a halogen atom, and X represents a halogen atom. ] It exists in the water-soluble formazan dye shown by these.

Hereinafter, the present invention will be described in detail.

The water-soluble formazan dye of the present invention is represented by the general formula [I] shown above, and the point of the present invention is that an alkenyl group which may be substituted with a halogen atom is selected as R. Examples of the halogen atom include chlorine atom, fluorine atom and bromine atom. Specific examples of the alkenyl group which may be substituted by a halogen atom represented by the R, for _{example, -CH 2 -CH = CH-CH} 3, -CH 2 -CH = CH 2, Etc., and the carbon number of the alkenyl group is usually 3 to 5.

On the other hand, in the general formula [I] shown above, the halogen atom represented by X is usually chlorine, fluorine or bromine.

The formazan dye represented by the general formula [I] shown above is, for example, the following general formula [II] 1 mol of the compound represented by the formula [III] [In the formula, X and R are the same as defined above. ] It can manufacture by condensing with 1 mol of the compound represented by these.

The formazan dye of the present invention exists in the form of a free acid or a salt thereof, and the salt is usually an alkali metal salt or an alkaline earth metal salt, and a lithium salt and a sodium salt are particularly preferable.

The water-soluble formazan dye of the present invention can be widely used as a dye for dyeing fibers and cloths, a dye for coloring paper and synthetic resins, and is particularly suitable as a dye. When used as a dye, the target fiber is usually cotton, viscose rayon,
Cellulosic fibers such as capra ammonium rayon and hemp, and nitrogen-containing fibers such as polyamide, wool and silk are mentioned, and cellulose fibers are particularly desirable. Further, these fibers are, for example, polyester, triacetate,
Mixed fibers such as polyacrylonitrile may be used.

As a method of dyeing a cellulosic fiber using the formazan dye of the present invention, a dyeing method such as a printing method or a dip dyeing method similar to the dyeing method using a known reactive dye is usually employed. For example, in the printing method, sodium alginate, emulsion paste, etc. are usually used as the base paste, and a dye,
A color paste prepared by adding an acid binder, urea and the like is prepared, printed on a fiber, and if necessary, after intermediate drying, steam or dry heat treatment is performed to fix the dye. In this case, a color paste containing no acid binder is printed on the fiber impregnated with the acid binder, or a color paste containing no acid binder is printed, and then the solution containing the acid binder is used. The dye may be fixed by performing the same treatment as described above after treating with the dye. Further, in the case of a dyeing method having a relatively large bath ratio such as the dip dyeing method, usually, in the presence of an inorganic salt such as sodium sulfate or sodium chloride, 30 to
After dyeing at a temperature of 100 ° C, preferably 40 to 70 ° C for a few minutes to a few tens of minutes, an acid binder is added, and further a few minutes to a few tens of minutes at the same temperature. It is also possible to dye in the presence of an acid binder from the beginning. Further, in the case of a dyeing method with a relatively small bath ratio such as a padding dyeing method, a pad prepared from a dye, an acid binder, a penetrant, urea as a solubilizer, sodium alginate as a migration inhibitor, etc. After padding and squeezing the fiber in the bath,
The dye is fixed by steaming or dry heat treatment.

Examples of the acid binder used in the above dyeing method include sodium hydrogen carbonate, sodium metaphosphate,
Trisodium phosphate, ortho or sodium metasilicate,
Examples thereof include sodium carbonate and sodium hydroxide.

〔Example〕

Hereinafter, the present invention will be described more specifically by way of examples, but the present invention is not limited to these examples as long as the gist thereof is not exceeded.

Example 1 (Production Example) The following structural formula in the form of free acid 1 mol ratio of the formazan compound represented by and 1 mol ratio of 2,4-dichloro-6-allyloxytriazine are condensed in an aqueous medium at 25 to 35 ° C. and pH 4 to 6, and then salted out with sodium chloride. A formazan dye having the following structural formula (shown in the form of free acid) and an analysis value by visible light absorption was prepared.

(Dyeing example) A dyebath is prepared using 2 g or 20 g of the formazan dye of the present invention obtained in the above Production Example, 50 g of sodium sulfate, and 933 g of water, and 100 g of cotton knitted fabric is immersed in this dyebath, and at 30 ° C for 15 minutes. After the treatment, 15 g of sodium carbonate was added and treated at the same temperature for 15 minutes. Subsequently, the temperature was raised to 60 ° C., the treatment was carried out at the same temperature for 60 minutes, and the dyeing was carried out. Then, after washing with water, using 1000 g of an aqueous solution containing 2 parts of an anionic surfactant, at 95 to 100 ° C,
By soaping for 10 minutes, washing with water and drying,
A blue dyeing having good levelness was obtained.

This dyed product has a good build-up property, has a light fastness of grade 6, and a sweat-sunlight fastness (JIS alkali method) of 4 to
The grade 5 and the fastness to washing (JIS A4 method) were grade 5, which were all excellent.

Examples 2 to 13 The water-soluble formazan dyes of the present invention shown in Table 1 were synthesized according to the production example of Example 1, and cotton was dyed according to Example 1. The hue and visible absorption of the dyed product obtained at this time are as shown in Table 1, and in each case, the level dyeing property was good.

[Effects of the Invention] The water-soluble formazan dye of the present invention is a water-soluble blue dye having a monohalogenotriazine type reactive group having an alkenyloxy group as a reactive group in its structure, and has good build-up properties for cellulosic fibers. Can be dyed. Further, it is also good in level dyeability, fastness to light, fastness to sweat and sunlight, and fastness to washing.

Claims (1)

[Claims] 1. The following general formula [I] in the form of a free acid. [In the formula, R represents an alkenyl group which may be substituted with a halogen atom, and X represents a halogen atom. ] The water-soluble formazan dye shown by these.