JPS6363592B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a disazo dye for polyester fibers, and more specifically to a disazo dye that dyes polyester fibers in a vivid blue color and has excellent various fastnesses, temperature stability, and PH stability during dyeing. The disazo dye for polyester fibers of the present invention is
General formula below [] (wherein, X represents a chlorine atom, a nitro group or a trifluoromethyl group, Y represents a cyano group, a methoxycarbonyl group or an ethoxycarbonyl group, and Z represents a hydrogen atom, a chlorine atom, a methyl group or a lower alkylcarbonylamino group) , R ¹ and R ² are hydrogen atoms: cyclohexyl group:
Cyano group, hydroxyl group, methoxy group, methoxyethoxy group, acetyloxy group, chloroacetyloxy group, chloroethylcarbonyloxy group, methoxycarbonyloxy group, methoxycarbonyl group, benzyloxycarbonyl group, phenoxyethoxycarbonyl group, methoxyethoxy carbonyl group,
It represents a lower alkyl group substituted with a methylcarbamoyl group, phenoxy group, phenyl group or chlorophenyl group: or an unsubstituted lower alkyl group. ) is a new water-insoluble disazo dye. In the above general formula [], examples of the lower alkylcarbonylamino group represented by Z include an acetylamino group, and examples of the unsubstituted lower alkyl group represented by R ¹ and R ² include a methyl group,
Ethyl group, linear or branched propyl group,
Examples include butyl groups, cyano group, hydroxyl group, methoxy group, methoxyethoxy group, acetyloxy group, chloroacetyloxy group, chloropropionyloxy group, methoxycarbonyloxy group, methoxycarbonyl group, benzyloxycarbonyl group, phenoxy Ethoxycarbonyl group, methoxyethoxycarbonyl group, methylcarbamoyl group,
Examples of the lower alkyl group substituted with a phenoxy group, phenyl group or chlorophenyl group include a cyanomethyl group, a cyanoethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxyhexyl group, a methoxyethyl group,
Methoxyethoxyethyl group, acetyloxyethyl group, chloroacetyloxyethyl group, chloropropionyloxyethyl group, methoxycarbonyloxyethyl group, methoxycarbonylmethyl group,
Examples thereof include a methoxycarbonylethyl group, a benzyloxycarbonylethyl group, a phenoxyethoxycarbonylethyl group, a methoxyethoxycarbonylethyl group, a methylcarbamoylethyl group, a phenoxyethyl group, a benzyl group, a phenethyl group, and a p-chlorobenzyl group. The disazo dye represented by the above general formula [] is the following formula [] (wherein, X is the same as defined above) is diazotized to form the following formula [] (In the formula, Y is the same as defined above.) Coupled with an aminothiophene represented by the following formula [] (wherein, X and Y are the same as defined above) is diazotized to form the following general formula [] (In the formula, Z, R ¹ and R ² are the same as defined above.)
It can be produced by coupling with an aniline represented by: 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 Structural formula below 100 g of polyester fiber was immersed in a dyeing bath in which 0.5 g of the dye represented by was dispersed in 3 water containing 1 g of naphthalene sulfonic acid-formaldehyde condensate and 2 g of higher alcohol sulfate, and the dye was heated at 130°C.
After dyeing for 60 minutes, soaping, washing 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. 13.8 g of metanitroaniline was dissolved in 150 ml of 7% hydrochloric acid, the solution was cooled to 2°C, and then 2N-
Added 50 ml of sodium nitrite. At this time, the temperature is 5℃
I tried not to exceed. The obtained diazonium salt solution of aniline was added to a solution of 12.4 g of 2-amino-3-cyanothiophene dissolved in 200 ml of methanol.
The mixture was added at ℃ and stirred for 2 hours at the same temperature, and the precipitated monoazo compound was removed, washed with water, and dried. This monoazo compound (2-amino-3-cyano-5
- 13.5 g of (3-nitrophenylazo)thiophene was added to a mixture of 135 ml of acetic acid and 135 ml of phosphoric acid;
Then, nitrosyl sulfuric acid (prepared by dissolving 3.5 g of sodium sulfite in 20 g of 97% sulfuric acid) was gradually added to this mixture at 0 to 5°C, and the mixture was stirred at the same temperature for 30 minutes to prepare a diazo solution of a monoazo compound. . N-(ethyl)
8.7 g of -N-(β-cyanoethyl)aniline was dissolved in 200 ml of methanol and added to 200 g of ice and 100 ml of water. Add the diazo solution prepared earlier to this,
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 625 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 g of naphthalene sulfonic acid-formaldehyde condensate and 2 g of higher alcohol sulfate. Polyester fibers are dyed in this dye bath.
After immersing 100g and dyeing at 130°C for 60 minutes, soaping, washing with water and drying, 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 638 nm. Example 3 Structural formula below 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 100g and dyeing at 130°C for 60 minutes, soaping, washing with water and drying, 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 618 nm. Example 4 Structural formula below 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 100g and dyeing at 130°C for 60 minutes, soaping, washing with water and drying, 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 656 nm. Example 5 Structural formula below 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 soaking 100g and dyeing at 130°C for 60 minutes, soaking, washing with water and drying, 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 650 nm. Example 6 Structural formula below 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 soaking 100 g and dyeing at 130°C for 60 minutes, soaking, washing with water, and drying, a vivid reddish-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 605 nm. Example 7 Structural formula below 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 soaking 100 g and dyeing at 130°C for 60 minutes, soaking, washing with water, and drying, a vivid reddish-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 608 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.

【table】

【table】

【table】

Claims (1)

[Claims] 1. General formula (wherein, X represents a chlorine atom, a nitro group or a trifluoromethyl group, Y represents a cyano group, a methoxycarbonyl group or an ethoxycarbonyl group, and Z represents a hydrogen atom, a chlorine atom, a methyl group or a lower alkylcarbonylamino group) , R ¹ and R ² are hydrogen atoms: cyclohexyl group:
Cyano group, hydroxyl group, methoxy group, methoxyethoxy group, acetyloxy group, chloroacetyloxy group, chloroethylcarbonyloxy group, methoxycarbonyloxy group, methoxycarbonyl group, benzyloxycarbonyl group, phenoxyethoxycarbonyl group, methoxyethoxy carbonyl group,
It represents a lower alkyl group substituted with a methylcarbamoyl group, phenoxy group, phenyl group or chlorophenyl group: or an unsubstituted lower alkyl group. ) Disazo dye for polyester fibers.