JPS6324544B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a monoazo dye for polyester fibers, and more specifically, it dyes polyester fibers in a vivid blue color and improves various fastnesses, particularly light fastness,
This invention relates to monoazo dyes with excellent sublimation fastness, water fastness, temperature stability and PH stability during dyeing. The monoazo dye for polyester fibers of the present invention has the following general formula [] (In the formula, R ¹ is an alkenyl group optionally substituted with a halogen atom or a phenyl group, a lower alkoxy lower alkyl group, a lower alkoxy lower alkoxy lower alkyl group, a lower alkoxy lower alkoxy lower alkoxy lower alkyl group, an acyloxy lower alkyl group) , hydroxy lower alkyl group,
Represents a lower alkoxycarbonyloxy lower alkyl group, an alkenyloxycarbonyloxy lower alkyl group, a lower alkoxy lower alkoxycarbonyloxy lower alkyl group, a benzyloxycarbonyloxy lower alkyl group, or a phenoxy lower alkoxycarbonyloxy lower alkyl group, and R ² is a methyl group. Or represents an ethyl group. This is a new water-insoluble monoazo dye shown in In the above general formula [], the alkenyl group optionally substituted with a halogen atom or phenyl group represented by R ¹ includes allyl group, 2-methylallyl group, 2-chloroallyl group, 2-bromoallyl group, crotyl group, Examples of the lower alkoxy lower alkyl group include methoxyethyl group, ethoxyethyl group, propoxyethyl group, bunaxyethyl group, methoxybutoxy group, etc., and examples of the lower alkoxy lower alkoxy lower alkyl group include 3-phenylallyl group. Examples include methoxyethoxyethyl group, ethoxyethoxyethyl group, propoxyethoxyethyl group, butoxyethoxyethyl group, etc. Lower alkoxy lower alkoxy lower alkoxy lower alkyl groups include methoxyethoxyethoxyethyl group, ethoxyethoxyethoxyethyl group, propoxyethoxy Examples of the acyloxy lower alkyl group include an ethoxyethyl group, a butoxyethoxyethoxyethyl group, and an acetyloxyethyl group, a propionyloxyethyl group, a chloroacetyloxyethyl group, a chloropropionyloxyethyl group, and a benzoyloxyethyl group. Examples of the hydroxy lower alkyl group include a hydroxylethyl group and a hydroxylpropyl group, and examples of the lower alkoxycarbonyloxy lower alkyl group include a methoxycarbonyloxyethyl group, an ethoxycarbonyloxyethyl group, a butoxycarbonyloxyethyl group, etc. Examples of alkenyloxycarbonyloxy lower alkyl groups include allyloxycarbonyloxyethyl groups, lower alkoxy lower alkoxycarbonyl lower alkyl groups include methoxyethoxycarbonyloxyethyl groups, and benzyloxycarbonyloxy lower Examples of the alkyl group include a benzyloxycarbonyloxyethyl group, and examples of the phenoxy lower alkoxycarbonyloxy lower alkyl group include a phenoxymethoxycarbonyloxyethyl group. The monoazo dye represented by the general formula [] is
For example, the following formula [] The diazonium salt of 2-amino-5-nitrothienothiazole represented by the following general formula [] (In the formula, R ¹ and R ² have the same meanings as in the general formula [].) It can be produced by coupling with an aniline represented by the following formula. Fibers that can be dyed with the monoazo dye of the present invention include polyester fibers made of polyethylene terephthalate, polycondensates of terephthalic acid and 1,4-bis-(hydroxymethyl)cyclohexane, and natural fibers such as cotton, silk, and wool. Examples include blended products and blended products with the above-mentioned polyester fibers. In order to color polyester fibers using the dye of the present invention, since the dye represented by the general formula [] shown above is insoluble or sparingly soluble in water, naphthalene sulfonic acid and formaldehyde are used as dispersants in a conventional manner. Dyeing or printing may be carried out by preparing a dyeing bath or printing paste in which a condensate of , higher alcohol sulfuric ester, higher alkylbenzene sulfonate, etc. is dispersed in an aqueous medium. 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. In this case, even better results can be obtained if an acidic substance such as formic acid, acetic acid, phosphoric acid or ammonium sulfate is added to the dyeing bath. Furthermore, the dye represented by the general formula [] used in the method of the present invention may be used in combination with dyes of the same type or dyes of other systems, and among these, the dyes represented by the general formula [] can be used in combination with each other. Depending on the combination, good results such as improved dyeability may be obtained. 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 unless it exceeds the gist thereof. Example 1 The following structural formula A dyeing bath was prepared by dispersing 0.5 g of the dye represented by 3 in water 3 containing 1 g of naphthalene sulfonic acid formaldehyde condensate and 2 g of higher alcohol sulfate. Polyester fibers are dyed in this dye bath.
After immersing 100 g of the fabric and dyeing it at 130°C for 60 minutes, soaping, washing with water, and drying resulted in a vivid blue 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 as follows. 2-Amino-5-nitrothienothiazole 20.1
Nitrosyl sulfuric acid (prepared by dissolving 7.6 g of sodium nitrite in 50 ml of 9.5% sulfuric acid), acetic acid at 0-5℃
It was gradually added to a mixture of 300 ml and propionic acid and 50 ml, and stirred at the same temperature for 30 minutes to prepare a diazo solution. Dissolve 29.4 g of 5-acetylamino-N,N-diethoxyethylaniline in 400 ml of methanol,
Added to 350g of ice and 300ml of water. The diazo solution was added to this, and the mixture was stirred at 0 to 5°C for 1 hour, and the precipitated dye was removed, washed with water, and dried. λmax of this product
(acetone) was 600 nm. Example 2 Structural formula below A dyeing bath was prepared by dispersing 0.5 g of the dye represented by 3 in water 3 containing 1.5 g of a naphthalene sulfonic acid formaldehyde condensate and 1 g of higher alcohol sulfuric ester, and adding 15 g of a methylnaphthalene carrier thereto. 100 g of polyester fibers were immersed in this dyeing bath and dyed at 100° C. for 90 minutes, followed by soaping, washing and drying, resulting in a vivid blue dyed fabric. The light fastness, sublimation fastness and water fastness of the dyed fabric obtained and the temperature stability during dyeing of the above dyes,
PH stability was good. The dye used in the present invention was produced according to Example 1 using 38.2 g of 5-acetylamino-N,N-dimethoxyethoxyethylaniline as a coupling component. The λmax (acetone) of this product was 598 nm. Example 3 Structural formula below A dyeing bath was prepared by the method described in Example 1 using 0.5 g of the dye shown. 100 g of polyester fibers were immersed in this dyeing bath and dyed at 130° C. for 60 minutes, followed by soaping, washing and drying, resulting in a vivid blue 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 Invention 1 using 23.0 g of 5-acetylamino-N,N-diallylaniline as a coupling component. The λmax (acetone) of this product is 603nm
It was hot. Example 4 Polyester fibers were dyed using the dyes shown in Table 1 below in the same manner as in Example 1 to obtain dyed products with similar color tones.

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Claims (1)

[Claims] 1. General formula (In the formula, R ¹ is an alkenyl group optionally substituted with a halogen atom or a phenyl group, a lower alkoxy lower alkyl group, a lower alkoxy lower alkoxy lower alkyl group, a lower alkoxy lower alkoxy lower alkoxy lower alkyl group, an acyloxy lower alkyl group) , hydroxy lower alkyl group lower alkoxycarbonyloxy lower alkyl group,
It represents an alkenyloxycarbonyloxy lower alkyl group, a lower alkoxy lower alkoxycarbonyloxy lower alkyl group, a benzyloxycarbonyloxy lower alkyl group or a phenoxy lower alkoxycarbonyloxy lower alkyl group, and R ² represents a methyl group or an ethyl group. ) monoazo dye for polyester fibers.