JP3237775B2 - Monoazo dye - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention particularly relates to a water-insoluble blue-based monoazo disperse dye excellent in pH dependency and alkali sweat fastness.

[0002]

2. Description of the Related Art In recent years, polyester fibers are often subjected to alkali weight reduction in order to improve the feeling of the fibers. In this case, since the pH at the time of dyeing becomes high due to the alkali remaining in the fiber, there is a problem that reproducibility at the time of dyeing is reduced when dyeing with a conventional dye. For example, Japanese Patent Publication No. 57-47214 discloses a dye having the same basic skeleton as the monoazo dye represented by the general formula [I] but different substituents, that is, R ¹ and R ² are hydrogen atoms, and R ³ is a hydrogen atom. Ethyl groups, dyes in which R ⁴ is a methyl group are described, but the dyes have extremely poor pH dependence and are not suitable for dyeing polyester fibers that have been subjected to alkali weight loss processing. It is also inferior in alkali sweat fastness.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a blue disperse dye having good alkali resistance, excellent pH dependency, and excellent alkali sweat fastness and light fastness. Is what you do.

[0004]

SUMMARY OF THE INVENTION The gist of the present invention is as described above.
It exists in the monoazo dye represented by the general formula [I]. Below, the book
The invention will be described in detail. In the general formula [I], R¹Is
A hydrogen atom, a methyl group or a chlorine atom^TwoIs a hydrogen atom
Or a methyl group. R^ThreeC represented by₁~ C_Five
Examples of the alkyl group include a methyl group, an ethyl group, and n-propyl.
Group, i-propyl group, n-butyl group, sec-butyl
Group or n-pentyl group such as linear or branched C₁~
C_FiveExamples include an alkyl group. Also, R^FourIs phenyl
Group, benzyl group, phenoxy group, C ₁~ C_FiveAlkoxy
Group, C₁~ C_FiveShows an alkyl group or benzyloxy group
I forgot. Where R^FourIs an alkyl group,^ThreeAnd R^FourCharcoal
The sum of the prime numbers is 4 or more. R^FourC represented by₁~ C
_FiveAs the alkoxy group, R^ThreeC represented by₁~ C _Five
A linear or branched C corresponding to an alkyl group₁~ C_FiveA
And a lucoxy group. Also, R^FourC represented by₁~
C_FiveAs the alkyl group, R^ThreeWith an alkyl represented by
Similar ones can be mentioned.

[0005] Structural features of the present invention dyes are particularly phenyl group as R ^4, a benzyl group, a phenoxy group, or using a relatively large molecular weight substituents such as alkoxy group, or R
^When a C ₁ -C ₅ alkyl group is used as R ⁴ , R ^{3 is selected} so that the combined molecular weight of R ³ and R ⁴ is relatively large.
And the total number of carbon atoms of R ⁴ is 4 or more.

Among the dyes of the present invention represented by the above general formula [I], the following dyes (1) and (2) are advantageous. (1) R ¹ is a hydrogen atom, R ² is a methyl group, R ³ and R ⁴
Is independently a C ₁ -C ₅ alkyl group, and the total number of carbon atoms of R ³ and R ⁴ is 5 or more. (2) R ¹ is a methyl group or a chlorine atom, R ² is a hydrogen atom or a methyl group, Dyes in which R ³ and R ⁴ are ethyl groups In particular, in the general formula [I], R ¹ is a chlorine atom, R ²
Is preferably a hydrogen atom or a methyl group, and R ³ and R ⁴ are ethyl groups. The monoazo dye represented by the general formula (I) is, for example, the following general formula (II)

[0007]

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(Wherein R ¹ is the same as defined above) by diazotizing an amine represented by the following general formula [III]:

[0009]

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(Wherein R ² , R ³ and R ⁴ are the same as defined above), and can be produced by coupling with an aniline represented by the formula: Examples of the fibers that can be dyed with the monoazo dye of the present invention include polyethylene terephthalate, polyester fibers composed of a polycondensate of terephthalic acid and 1,4-bis- (hydroxymethyl) cyclohexane, and cotton, silk, and wool. Blended products of natural fibers and the above polyester fibers, and mixed woven products (cloths, woven and knitted fabrics, etc.) may be mentioned.

In carrying out the dyeing using the dye of the present invention, the monoazo dye represented by the above general formula [I] is dispersed in an aqueous medium by using a dispersant according to a conventional method, and the dye bath or the printing is carried out. A paste may be prepared and dyed or printed. For example, when performing dip dyeing, by applying ordinary dyeing treatment methods such as high-temperature dyeing method, carrier dyeing method, and thermosol dyeing method, it is possible to dye polyester fibers or a blended product thereof, and a dyed product having a good fastness to a mixed woven product. Can be applied. In some cases, better results may be obtained by adding an acidic substance to the dyeing bath.

The dyed fabric obtained by the above-described dyeing or printing using the monoazo dye of the present invention has excellent dyeing properties such as dyeing properties, build-up properties and pH dependency, and is resistant to alkali sweat. It is excellent in various fastnesses such as fastness to light, fastness to light, fastness to sublimation, fastness to washing, fastness to sweat and fastness to water. Furthermore, even when this dyed fabric is subjected to post-processing, it is not said that the wet fastness is significantly reduced in the present invention. The monoazo dye of the present invention may be used in combination with a dye of the same system or a dye of another system.

[0013]

EXAMPLES Next, the present invention will be described more specifically with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Example 1 In the general formula [I], R ¹ and R ² represent a hydrogen atom, R ³
Is an ethyl group and R ⁴ is a phenyl group. 0.5 g of the monoazo dye of the present invention is dispersed in 2 liters of water containing 0.25 g of a naphthalenesulfonic acid-formaldehyde condensate and 0.25 g of a higher alcohol sulfate, and a dyeing bath is prepared. Prepared. After 100 g of polyester fiber was immersed in this dyeing bath and dyed at 130 ° C. for 60 minutes, soaping, washing and drying were carried out to obtain a clear blue dyed fabric. The pH dependence of the dye at the time of dyeing is 100,
Alkali sweat fastness was excellent at 4-5 class.

[0014] The pH dependency depends on the pH in the above-mentioned dyeing method.
The dyeing amount when dyeing at pH 9.5 with respect to the dyeing amount when dyeing at 5.0 is expressed as a percentage and 100 is the best. The alkali sweat fastness was determined by the degree of contamination of a nylon white cloth according to the JIS0848A method. The dye used in this example was produced as follows.

16.9 g of 2-amino-3-cyano-5-nitrothiophene are dissolved in a mixture of 33 g of 98% sulfuric acid and 33 g of glacial acetic acid, and then 43% nitrosyl sulfate 33%
g was added at 5 ° C., and the mixture was stirred for 2 hours to obtain a diazo liquid.
Incidentally, 2-amino-3-cyano-5-nitrothiophene was synthesized according to the method described in JP-B-57-47214. Next, 34.3 g of N-ethyl-N-phenylcarbonyloxyethylaniline was added to 500 ml of methanol.
After dissolving in the above, the above diazo liquid is added dropwise at 10 ° C. or less,
Next, the mixture was neutralized to pH 5 with sodium acetate, filtered, washed with water, and dried to obtain a target dye. The maximum absorption wavelength (λmax: in acetone) of the dye was 596 nm.

Comparative Example 1 has the same basic skeleton as that of the above-mentioned general formula [I], provided that R ¹
And a compound in which R ² is a hydrogen atom, R ³ is an ethyl group, and R ⁴ is a methyl group (corresponding to the compound of Japanese Patent Publication No. 57-47214, Example 94) was synthesized according to Example 1. The polyester fiber was dyed and evaluated in the same manner as in Example 1. As a result, the pH dependency was remarkably poor at 60, and the alkali sweat fastness was poor at the third grade.

Examples 2 to 31 The dyes shown in Table 1 were synthesized according to Example 1, and polyester fibers were dyed in the same manner as in Example 1 to examine pH dependency and alkali sweat fastness. . The results are shown in Table 1.

[0018]

[Table 1]

[0019]

[Table 2]

[0020]

The compounds of the present invention are described, for example, in
Despite being very structurally similar to the known compound according to JP-A-47214, the pH-dependence and the pH-dependency and the solubility of the amino group of the coupling component are different from those of the known compound due to the difference in the terminal of one substituent of the amino group. It has good alkali sweat fastness and is extremely useful as a dye for polyester fibers.

Continuation of the front page (56) References JP-A-48-84120 (JP, A) JP-A-58-1557863 (JP, A) JP-A-60-239291 (JP, A) (58) Fields investigated (Int) .Cl. ⁷ , DB name) C09B 29/09 CA (STN) REGISTRY (STN)

Claims (1)

(57) [Claims] 1. A compound represented by the following general formula [I] (Wherein, R ¹ represents a hydrogen atom, a methyl group or a chlorine atom, R ² represents a hydrogen atom or a methyl group, R ³ represents a C ₁ -C ₅ alkyl group, R ⁴ represents a phenyl group or a benzyl group. Phenoxy group, C ₁ -C ₅ alkoxy group, C
Represent ₁ -C ₅ alkyl group or a benzyl group.
However, when R ⁴ is an alkyl group, the total number of carbon atoms of R ³ and R ⁴ is 4 or more. ).