JPS6339965A - Monoazo dye - Google Patents

Abstract

NEW MATERIAL:Monoazo compds. of formula I, wherein R<1> is a substd. or unsubstituted alkyl, alkenyl, aralkyl or cycloalkyl; R<2> is H, an alkyl, a halogen- substd. alkyl, phenyl, an aralkyl, phenoxymethyl, an alkoxy, phenoxy or an araalkyloxy; R<3> and R are each H, an alkyl, cyano, nitro, halogen, COOR<1>, trifluoromethyl, hydroxyethyl, an alkylcarbonyl, benzoyl or an acylamino. USE:Monoazo dyes which dye polyester and natural fibers such as cotton, silk, wool, etc. red. PREPARATION:A compd. of formula II is dissolved in a polar solvent such as dimethylformamide and reacted with cuprous cyanide at 20-100 deg.C for 1-5 hr to obtain the desired compd.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to monoazo dyes, in particular:
In particular, it relates to a water-insoluble red monoazo dye that has excellent wet fastness after post-processing.

Conventional technologyRecently, a new dyeing technology for polyester fibers has been developed.
After dyeing, many post-processing treatments such as antistatic processing, texture adjustment processing, and water resistance processing are now being carried out. These post-processing treatments are usually carried out by applying an organic agent such as polyurethane or silicone to the surface of the dyed polyester fiber and heat-treating it at a high temperature of about 130 to 180°C. There is a drawback that the dye being dyed bleeds out, and as a result, the fastness after post-processing, particularly the wet fastness, tends to be significantly reduced. For example, the dye having the structure shown below (the dye described in JP-A-53-113830) has a hydrophilic alkylsulfonyl group, and therefore has a significantly poor wet fastness after post-processing.

Problems to be Solved by the Invention The object of the present invention is to provide a monoazo dye having excellent wet fastness after post-processing and having high practical value.

□ Means to Solve the Problem The present invention is based on the general formula [I] represents an alkyl group, a halogen-substituted alkyl group, a phenyl group, an aralkyl group, a phenoxymethyl group, an alkoxy group, a phenoxy group, or an aralkyloxy group, and R3 and R4 are each a hydrogen atom, an alkyl group, a cyano group, a nitro group, a halogen atom, COOR
1, trifluoromethyl group, hydroxyethyl group, alkylcarbonyl group, benzoyl group, or acylamino group).

Hereinafter, to explain the present invention in detail, in the monoazo dye of the present invention represented by the general formula [I], the unsubstituted alkyl group represented by R1 includes, for example, a methyl group,
Examples include linear or branched 01-C8 alkyl groups such as ethyl group, propyl group, and butyl group. Examples of substituted alkyl groups include methoxyethyl group, ethoxyethyl group, and linear or branched alkyl group. 01-C8 alkoxyalkyl group, phenoxyethyl group: Aralkyloxyalkyl group such as benzyl group, phenethyl group: Allyloxyethyl group: 01-C8 alkyloxyethoxyethyl group:
01-C8 alkoxycarbonylalkyl groups such as C2-C1 alkoxycarbonylethyllopyl group (further, the alkoxy group may be substituted with methoxy group, ethoxy group, phenoxy group, etc.): hydroxyethyl group, hydroxybutyl group Hydroxyalkyl groups such as Niacetyloxyethyl group, C1-C6 alkylcarponyloxyethyl group such as propionyloxyethyl group: C1-C8 such as benzoyloxyethyl group, methoxycarbonyloxyethyl group, ethoxylponyloxyethyl group, etc. An example is an alkoxycarbonyloxyethyl group. Further, examples of the cycloalkyl group include a cyclohexyl group, and examples of the alkenyl group include C3-C4 alkenyl groups such as allyl group, methylallyl group, and 2-bromoallyl group.

Examples of the aralkyl group represented by R and R2 include C6-CIO aralkyl groups such as benzyl group, phenethyl group and phenylpropyl group, and halogen atoms represented by R2 and R3 include F, CI,
Examples of the alkyl group include Br and I, and examples of the alkyl group represented by R2, R3 and R4 include 01-C4 alkyl groups. Further, as the acylamino group represented by R3 and R4, for example, 01 to C4 acylamino groups such as an acetylamino group, a propionylamino group, a butyrylamino group, a methoxycarbonylamino group, an ethoxycarbonylamino group, and a butoxycarbonylamino group. Can be mentioned.

The monoazo dye of the present invention represented by the general formula [I] is
For example, it can be manufactured as follows.

That is, a compound represented by the following general formula [II] (wherein R1, R2, R3, and R4 are the same as defined above) is dissolved in a polar solvent such as dimethylformamide, and then mixed with cupric cyanide for 20 minutes. It is produced by reacting at ~100°C, preferably 70°C for 1 to 5 hours.

Fibers that can be dyed with the monoazo dye of the present invention include polyethylene terephthalate, terephthalic acid and 1,4
Examples include polyester fibers made of polycondensates with -bis-(hydroxymethyl)cyclohexane, blends and blends (cloth, woven and knitted fabrics, etc.) of natural fibers such as cotton, silk, and wool with the above polyester fibers. It will be done.

When carrying out dyeing using the dye of the present invention, a dispersant is used to disperse the monoazo dye represented by the general formula [I] in an aqueous medium, and then the dyeing bath or printing paste is prepared. All you have to do is adjust it and perform dyeing or printing.

For example, when dyeing is performed, ordinary dyeing methods such as high-temperature dyeing, carrier dyeing, and thermosol dyeing are applied to dye polyester fibers, their blends, and i-woven products with excellent fastness. can be administered.

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

The dyed fabric obtained by the above-mentioned dip dyeing or printing using the monoazo dye of the present invention has excellent properties during dyeing such as dyeability, build-up property, and temperature dependence.

Furthermore, it has excellent fastness properties such as light fastness, sublimation fastness, washing fastness, sweat fastness, and water fastness. Furthermore, even when this dyed fabric is subjected to post-processing, the wet fastness does not decrease significantly in the present invention.

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

Although the monoazo dye of the present invention is structurally very similar to conventionally known compounds (for example, those described in JP-A-53-113830), an acylamino group is introduced into the coupling component. In addition, since the N substitution is monosubstitution, it is possible to maintain high wet fastness after post-processing compared to known compounds.

Examples Next, the present invention will be explained in more detail by examples.
The present invention is not limited to the following examples.

A dyeing bath was prepared by dispersing 0.5 g of the monoazo dye of the present invention shown in Example 1 in water 31 containing 1.0 g of a naphthalene sulfonic acid-formaldehyde condensate and 2.0 g of higher alcohol sulfate ester.

Polyester cloth 1009 is dipped in this dyeing bath,
After dyeing for 60 minutes at .degree. C., saw pink, washed with water and dried, a red-dyed polyester cloth with good light fastness, sublimation fastness, and wet fastness was obtained. This polyester cloth was subjected to polyurethane processing, and the wet fastness after that was evaluated, and the results shown in Table 1 were obtained.

The dye used in this example was prepared as follows.

Dimethylformamide 50d
2,0g of cuprous cyanide was added at 60°C,
After stirring at the same temperature for 3 hours, 20 d of 10% ferric chloride aqueous solution
and the resulting precipitate was filtered out. After drying,
4.3 g (yield: 90%) of the monoazo dye of the present invention represented by the above structural formula [1-11] was obtained. Maximum absorption wavelength of crystal λ
max (acetone) was 522 nm.

Comparative Example 1 Using the dyes listed in Table 1 below, the following (i) and (
The wet fastness after polyurethane processing was evaluated according to the method described in ii). The results are shown in Table 1 below.

(i) Washing fastness A multi-fiber was attached to a dyed cloth treated with polyurethane, and a washing test was conducted according to the AATCC washing method ■A@, and the contamination of the nylon fibers of the multi-fiber was determined on a gray scale.

(ii) Alkaline sweat fastness: dyed fabric treated with polyurethane according to JISL-0848
The test was conducted in accordance with Method A, except that nylon cloth and silk cloth were used as the attached cloths, and the degree of contamination of the silk cloth was determined on a gray scale.

Example 2 Polyerther fibers were dyed using the dyes shown in Table 2 below in the same manner as in Example 1 to obtain dyed products having the colors shown in the table. Furthermore, the alkaline sweat fastness of these materials after polyurethane processing was evaluated. The results were as shown in Table 2.

Effects of the Invention As shown in the examples above, the monoazo dye of the present invention not only has a high degree of fastness after dyeing, but also allows dyed fabrics to be processed with polyurethane to improve texture, waterproof, or prevent static electricity. Or when subjected to silicon processing, etc.
The subsequent wet fastness (fastness after post-processing) is extremely high.

Therefore, the monoazo dye of the present invention is particularly suitable as a dye for high-quality clothing that undergoes post-processing.

Claims (1)

[Claims] The following general formula [I] ▲ Numerical formulas, chemical formulas, tables, etc.▼ [I] (In the formula, R^1 is a substituted or unsubstituted alkyl group, alkenyl group, aralkyl group, or cycloalkyl group , R^2 represents a hydrogen atom, an alkyl group, a halogen-substituted alkyl group, a phenyl group, an aralkyl group, a phenoxymethyl group, an alkoxy group, a phenoxy group, or an aralkyloxy group, and R^3 and R^4 each represent hydrogen. Atom, alkyl group, cyano group, nitro group, halogen atom,
A monoazo dye represented by a COOR^1 group, a trifluoromethyl group, a hydroxyethyl group, an alkylcarbonyl group, a benzoyl group or an acylamino group.