JPS5829859A - Monoazo dye for polyester fiber - Google Patents

Abstract

PURPOSE:To provide a monoazo dye consisting of a specified monoazo compd. which shows excellent temperature and pH dependence in dyeing and dyes polyester fibre in a bright red color with excellent fasteness to water. CONSTITUTION:A monoazo compd. of formulaI(where R and R' are each 1-8C alkyl) (e.g. a compd. of formula II) is used as a red dye for polyester fibre and its blend with natural fiber such as cotton or wool. The monoazo dye is synthesized by reacting a compd. of formula III with a compd. of formula IV (where X is halogen) or V[where D is (substd.) phenyl].

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a monoazo dye for polyester fibers, and more specifically, the present invention line, 11 degree dependence and pH dependence during dyeing are good, and polyester ai1! This invention relates to a monoazo dye that dyes fibers in a bright red color with excellent water resistance.

The present inventors expressed the following general formula (wherein R' represents an alkyl group having 7 to t carbon atoms, ul is an alknyl group, lower alkoxyalkyl & lower alkoxyalkoxyalkyl &, ta alkoxyalkoxyalfukidialkyl group, Alknyloxy lower alkyl group, tetrahydrofurfuryl group, aryloxy lower alkyl group, acyloxy lower alkyl group,
It represents an optionally substituted hydroxyalkyl group, a low M flukoxycarbonylalkyl group, a lower aralkyloxycarbonyl lower alkyl group, an acyloxy lower alkyl group, a cyanoethoxy lower alkyl group, or a cono-phosphate indo-lower alkyl group. ) It was discovered that the monoazo dye represented by the following is a red dye for polyester fibers having excellent properties, and an application has already been filed (%Application #3jj-11131141).

The present inventors have conducted intensive studies to further improve the humidity dependence and pH dependence during dyeing, as well as the water fastness of dyes having the above-mentioned skeleton. As a result, the general formula [I] (3, H, ,,M (W.

(In the formula, R and Ro represent the alkyl group ft of the number of leg element atoms/-1.)
We discovered that it is a dye that has good H dependence and dyes polyester fibers a bright red color with excellent water resistance.
This invention is based on the present invention.

To explain the present invention in detail, the general formula (1') shown above has h
R and Ro are methyl group, ethyl group, linear or branched propyl group, butyl group, pentyl group,
Number of carbon atoms in hexyl, heptyl, octyl, etc./
-r is an alkyl group.

The monoazo dye represented by the general formula (1) is represented by the general formula (
1) A compound represented by the formula % (in the formula, R and Ro are the same as defined above) is converted into a compound represented by the general formula x -CH, (1!N -------・[1f) (in the formula , X represents a halogen atom), or is a compound represented by the general formula (M) D -80,CH,ON...Φ (IV) (wherein
D represents optionally substituted phenyl. ) Manufactured by reacting with the compound shown below.

Specific examples of the sulfonic acid esters represented by the general formula [■], which are the seven raw materials for the dye of the present invention, include p-toluenesulfonic acid cyanomethyl ester, phenylsulfonic acid cyanomethyl ester, etc. It will be done.

Further, specific examples of the 710 compound represented by the general formula [melon] include chloroacetonitrile, bromoacetonitrile, and iodoacetonitrile.

The compound represented by the general formula [■] is Koamino! ,j
- diazotizing dicyanoimidazole by a conventional method, M,
Obtained by coupling with N-disubstituted-m-)luidine.

The dye of the present invention is a compound represented by the general formula (1) such as ochlorobenzene, dichlorobenzene, trichlorobenzene,
Aromatic solvents such as nido-benzene and orthonitrotoluene, N-alkylformamides such as dimethylformand, N-alcoholic rubyridones such as N-methylpyrrolidone, ketones such as acetone and methyl ethyl ketone, and alcohols such as methanol. 1 in an inert solvent such as a nitrile chain such as acetonitrile, pyridine in a water-organic solvent such as water-acet/, water-acetonitrile, water-methyl ethyl ketone, water-tetrahydrofuran, (-N-) tilpyrrolidone, etc. Organic compounds such as piperidine, sodium carbonate, potassium carbonate, magnesium oxide, sodium hydroxide, sodium bicarbonate, etc. are prepared using the formula A halide represented by [Zen] or a sulfonic acid ester represented by formula (IV) and 20 to Q
By heating to 0°C, a pure product can be obtained in good yield.

Fibers that can be dyed with the monoazo-dyed NK of the present invention include:
Polyethylene terephthalate, terephthal JLL/14
'-Bis-(hydroxymethyl)cyclohexane and polyester fiber made of polycondensed metal, or cotton;
Examples include blended products and mixed fiber products of natural fibers such as silk and wool and the above-mentioned polyester fibers.

In order to dye polyester fibers using the dye of the present invention, the dye represented by the general formula [1] shown above is added to water in small drops or S
Since it is wet, dyeing baths or textile printing are carried out using conventional methods as dispersants such as condensates of naphthalene sulfonic acid and formaldehyde, higher alcohol sulfuric acid esters, higher 1-alkyl benzene sulfonic acids, etc., dispersed in an aqueous medium. Glue, dyeing, or printing may be performed. For example, in the case of dip dyeing, polyester fibers or their blends can be dyed with excellent firmness by applying ordinary dyeing methods such as high-temperature dyeing, medium-yellow dyeing, and nermosol dyeing. . At that time, depending on the case, use formic acid, acetic acid, phosphoric acid, Fi-sulfuric acid, etc. in the dyeing bath.
Even better results can be obtained by adding an acidic substance such as phosphorium.

Furthermore, the dye represented by the general formula (1) used in the method of the present invention may be used in combination with dyes of the same type or dyes of other types. In some cases, good results such as improved printing and dyeing properties can be obtained by incorporating the above.

Next, the present invention will be explained in more detail with reference to examples.
-J and Comparative Example/-j, the pH stability was expressed numerically by the staining concentration at pg+lc, where /DO is the staining concentration at pHj. OpH during staining is normal! However, the higher the value, the more the dye decomposes and the quality of the dye decreases. Furthermore, the dyeing density at a temperature of 1-0°C is numerically shown, where the dyeing density at a temperature stability of 111/JO°C is taken as 100. The temperature during dyeing is usually IJO.
℃, but as the temperature decreases, the dyeing density decreases.

Fuchisadacho Hytran IP core ax with high water resistance after resin processing
(manufactured by Dainippon Ink Co., Ltd.) toe/llIc Soak at room temperature for 2 minutes, dry at 100℃ for λ minutes, and dry heat at 740℃ for 2 minutes: fXBL 014 bow (/7t)
Based on this, nylon contamination and rayon contamination were measured.

In addition, sweat fastness measurements were made after similar resin processing.
: Based on JLB'LxOtllr (/971), Sil/
Example 1 Dye 011 represented by the following structural formula was dispersed in 3 t of water containing 7-talenesulfonic acid formaldehyde condensate II and higher al; did. Immerse 10t of polyester fibers in this dyeing bath,
After dyeing at 30° C. for 40 minutes, soaping, washing with water and drying were performed, a bright mackerel-colored dyed fabric with good light resistance and sublimation resistance was obtained. The evaluation is shown in the table.

The dye used in this example was forged as follows.

A mixture of the compound Hiroko/1 ric IV O was added over time, then stirred for 10 hours, and chloroacetonitrile 3. Add θl and stir for an additional hour. Then, after cooling to room temperature, the precipitated crystals were discharged into 1 L of water, separated, washed, and dried to obtain dark red crystals of the dye represented by the following formula.

1mlLX (acetone) of this product was j30nm.

Comparative Example/ Polyester fiber was dyed in the same manner as in Example/ except that a dye represented by the following structural formula was used to obtain a dyed fabric with a vivid bluish red color. The evaluation is shown in Table-7.

Table 7 Example Dyeing was carried out in the same manner as in Example 1 using dyes O and St shown by the following structural formulas, and a clear bluish red dye with good light resistance and sublimation resistance was obtained. A cloth was obtained.

The evaluation is 0 as shown in the table. The dye used in this example was produced as follows.

Compound 3 represented by the following formula, Jt HOH.

A mixture of sodium bicarbonate, methyl ethyl ketone, and water was stirred at room temperature for 30 minutes. Added chloroacetonitrile/l, 09, gradually raised the temperature, stirred at 72°C for 20 hours, then cooled to room temperature, added methanol 〇〇7, stirred at room temperature for 2 hours,
The precipitated crystals were allowed to pass through. After washing and drying, dark mackerel-colored crystals of the dye represented by the following formula, jTI, were obtained.

This product was λrnax (acetone) and jJInrn.

Comparative Example λ A polyester fiber was dyed in the same manner as in Example except that a dye represented by the following structural formula was used to obtain a dyed fabric with a vivid bluish red color. Evaluation Fi Table-1 0 Table-2 Dormitory Example J Dye represented by the following structural formula 0. When dyeing was carried out in the same manner as in Example 1 using Jl, a clear bluish-colored dyed fabric with good light fastness and sublimation resistance was obtained. The evaluation is shown in Table-3.

Book! The dye used in Example 1 was produced by pressing as follows.

Compound represented by the following formula $ J, / #chloroacetonitrile r, o y and N-methylpyrrolidone coOwt
The mixture was heated to 10° C. and after 1 hour, sodium carbonate J, Jll was gradually added over 10 hours. after that,
Stir for an hour, add 3.01 liters of chloroacetonitrile,
Even more! Stir for hours. Then, after cooling to room temperature, add 1 liter of water.
When the precipitated crystals were separated, washed and dried, dark red crystals of the dye represented by the following formula <t2.01 were obtained.

λmlL of this product! (Acetone)
s-tsuta.

Comparative Example 3 Polyester fibers were dyed in the same manner as in Example except that a dye represented by the following structural formula was used to obtain a dyed fabric with a vivid bluish red color. The evaluation is shown in Table 3.0Table-J Example ReferenceExample/Polyester fibers were dyed using the dyes shown in the table below in the same manner as in Example/, and dyed products with the colors shown in the table were obtained. .

/- Next −= η

Claims (1)

[Claims] (1) A monoazo dye for polyester fibers represented by the general formula (in the formula, R and R represent an alkyl group having carbon atoms/-1).