JPH0118946B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a disazo 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 disazo dyes that have excellent sublimation fastness, water fastness, temperature stability during dyeing, and PH stability. The disazo dye for polyester fibers of the present invention is
General formula below [] (In the formula, D represents a halogen atom, a nitro group, a phenyl group optionally substituted with a lower alkyl group or a lower alkoxycarbonyl group, a pyridyl group, or a thiazolyl group optionally substituted with a nitro group, and X represents a lower alkyl group) represents a group, Y represents a hydrogen atom, a methyl group or an acylamino group,
Z represents a hydrogen atom, a chlorine atom, a methyl group or a methoxy group, and R ¹ and R ² represent a hydrogen atom, a cyano group, a hydroxy group, a phenyl group, a lower alkoxy group, a lower alkylcarbonyloxy group, a lower alkoxycarbonyl group, a lower Represents an alkoxycarbonyloxy group, a chloro-lower alkylcarbonyloxy group, a benzyloxycarbonyl group, a phenoxycarbonyloxy group, a lower alkoxy lower alkoxycarbonyl group, a lower alkyl group which may be substituted with an allyloxy group, or an allyl group. ) is a disazo dye for polyester fibers. The thiazolyl group optionally substituted with a halogen atom, a nitro group, a lower alkyl group or a lower alkoxycarbonyl group, a phenyl group optionally substituted with a pyridyl group, or a nitro group represented by D in the above general formula [] is , a phenyl group; a phenyl group substituted with a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, a lower alkyl group such as a nitro group, a methyl group, an ethyl group, or a lower alkoxycarbonyl group such as a methoxycarbonyl group; a pyridyl group; Examples include a thiazolyl group or a thiazolyl group substituted with a nitro group, and the lower alkyl group represented by X includes a methyl group, an ethyl group,
Examples of the acylamino group represented by Y include acetylamino group, chloroacetylamino group, benzoylamino group, methylsulfonylamino group, chloropropionylamino group, ethoxycarbonylamino group, ethylaminocarbonylamino group, etc. can be mentioned. As R ¹ and R ² , hydrogen atoms; lower alkyl groups such as methyl group, ethyl group, linear or branched propyl group, butyl group; cyano lower alkyl groups such as cyanomethyl group and cyanoethyl group; hydroxyethyl hydroxyl lower alkyl groups such as hydroxypropyl, hydroxybutyl; phenyl-substituted lower alkyl groups such as benzyl; lower alkoxy lower alkyl groups such as methoxyethyl, ethoxyethyl, butoxyethyl; acetyloxyethyl, etc. lower alkylcarbonyloxy lower alkyl groups; lower alkoxycarbonyl lower alkyl groups such as methoxycarbonylmethyl group and ethoxycarbonylmethyl group; lower alkoxycarbonyloxy lower alkyl groups such as methoxycarbonyloxyethyl group; chloroacetyloxyethyl group, chloropropionyl Chlorolower alkylcarbonyloxy lower alkyl groups such as oxyethyl group; Benzyloxycarbonyl lower alkyl groups such as benzyloxycarbonylmethyl group; Phenoxycarbonyloxy lower alkyl groups such as phenoxycarbonyloxyethyl group; Methoxyethoxycarbonylmethyl Examples include lower alkoxy lower alkoxy carbonyl lower alkyl groups such as groups; allyloxy lower alkyl groups such as allyloxyethyl groups, and allyl groups. The disazo dye represented by the above general formula [] is obtained by diazotizing the amine represented by the following formula [] D-NH ₂ ... [] (wherein, D is the same as the above definition), and by diazotizing the amine represented by the following formula [] (In the formula, X is the same as defined above.) 2
The following formula obtained by coupling with -amino-3-(lower alkylsulfonyl)thiophenes [] (wherein D and X are the same as defined above) is diazotized to form the following general formula [] (In the formula, Y, Z, R ¹ and R ² are the same as defined above.) It can be produced by coupling with an aniline represented by the above formula. As the amine represented by the general formula D-NH ₂ ,
Benzene-based amines, such as aniline; o-, m
-, or p-fluoroaniline; o-, m-,
or p-chloroaniline; o-, m-, or p-promaniline; 2,4-dichloroaniline, 2,3-dichloroaniline, 2-chloro-4
-bromoaniline, 2,4-difluoroaniline, 2,4,6-trichloroaniline; o-, m
-, or p-toluidine; o-, m-, or p-ethylaniline; o-, m-, or p-nitroaniline; 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline; o ―, m
- or p-methoxycarbonylaniline, o
-, m-, or p-ethoxycarbonylaniline, p-butoxycarbonylaniline; 2-chloro-4-methoxycarbonylaniline, etc.; examples of pyridine-based amines include 3-aminopyridine; The amines include 2-aminothiazole; 2-amino-5-
Examples include nitrothiazole. Fibers that can be dyed with the disazo 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 of fibers and the above-mentioned polyester fibers. In order to dye 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, higher alcohol sulfuric ester, higher alkylbenzene sulfonate, etc. are 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 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of 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. 9.3 g of aniline was dissolved in 150 ml of 7% hydrochloric acid, the solution was cooled to 2°C, and then 50 ml of 2N sodium nitrite was added. At this time, the temperature was set not to exceed 5°C. The obtained aniline diazonium salt solution was mixed with 2-amino-3-(methylsulfonyl)
A solution of 16.3 g of thiophene dissolved in 200 ml of methanol was added at 2° C., stirred at the same temperature for 2 hours, and the precipitated monoazo compound was removed, washed with water, and dried. This monoazo compound (2-amino-3
-(methylsulfonyl)-5-phenylazothiophene) was added to a mixture of 134 ml of acetic acid and 134 ml of phosphoric acid, and the mixture was then heated at 0-5°C.
At the same temperature, nitrosyl sulfuric acid (prepared by dissolving 3.5 g of sodium nitrite in 20 g of 97% sulfuric acid) was gradually added.
The mixture was stirred for 30 minutes to prepare a diazo solution of a monoazo compound. 10.5 g of N-ethyl-N-β-acetoxyethylaniline was dissolved in 200 ml of methanol and added to 200 g of ice and 100 ml of water. The diazo solution prepared above was added thereto, and the mixture was stirred at 0 to 5°C for 2 hours, and the precipitated disazo dye was removed, washed with water, and dried. The λmax (acetone) of this product was 617 nm. Example 2 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of 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 according to Example 1. The λmax (acetone) of this product was 617 nm. Example 3 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of 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 6 minutes, soaping, washing with water, and drying were performed, a vivid blue dyed fabric was obtained. 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 Example 1. The λmax (acetone) of this product was 640 nm. Example 4 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of 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 according to Example 1. The λmax (acetone) of this product was 625 nm. Example 5 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of 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 according to Example 1. The λmax (acetone) of this product was 679 nm. Example 6 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of 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 according to Example 1. The λmax (acetone) of this product was 619 nm. Example 7 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of 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 according to Example 1. The λmax (acetone) of this product was 615 nm. Example 8 Polyester fibers were dyed using the dyes shown in Table 1 below in the same manner as in Example 1 to obtain dyed products having the colors shown in the table.

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【table】

【table】

【table】

Claims (1)

[Claims] 1 (In the formula, D represents a halogen atom, a nitro group, a phenyl group optionally substituted with a lower alkyl group or a lower alkoxycarbonyl group, a pyridyl group, or a thiazolyl group optionally substituted with a nitro group, and X represents a lower alkyl group) represents a group, Y represents a hydrogen atom, a methyl group or an acylamino group,
Z represents a hydrogen atom, a chlorine atom, a methyl group or a methoxy group, and R ¹ and R ² represent a hydrogen atom, a cyano group, a hydroxy group, a phenyl group, a lower alkoxy group, a lower alkylcarbonyloxy group, a lower alkoxycarbonyl group, a lower Represents an alkoxycarbonyloxy group, a chloro-lower alkylcarbonyloxy group, a benzyloxycarbonyl group, a phenoxycarbonyloxy group, a lower alkoxy lower alkoxycarbonyl group, a lower alkyl group which may be substituted with an allyloxy group, or an allyl group. ) Disazo dye for polyester fibers.