JPH044343B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel monoazo compound and a method for dyeing or printing synthetic fibers using the same. More specifically, the present invention relates to a water-insoluble monoazo compound and a method for dyeing or printing synthetic fibers such as polyester fibers and polyamide fibers in blue using the same. That is, the present invention is based on the general formula () (wherein, (represents a lower alkyl group, an alkenyl group, a cycloalkyl group, or a phenyl group having a benzoyloxy group, a lower alkoxy group, a lower alkylcarbonyloxy group, a lower alkoxycarbonyloxy group, a benzoyloxy group, an anilinocarbonyloxy group, or a benzoyloxy group) A method for dyeing or printing synthetic fibers characterized by using the monoazo compound represented by: In the present invention, "lower" means having 1 to 4 carbon atoms. In the compound represented by the general formula (), X is preferably a hydrogen atom, a chlorine atom, a bromine atom, or a methyl group, and Z is preferably a methyl group, an acylamino group having 4 or less carbon atoms, or a benzoylamino group. The monoazo compound of the present invention has excellent properties as a disperse dye for synthetic fibers such as polyester fibers and polyamide fibers, such as dyeing properties, dye bath stability, PH stability, and build-up properties, and is also resistant to water and washing. It exhibits excellent fastness to various types of light, such as maturation, sublimation, and sunlight, especially after post-processing. In the present invention, the monoazo compound represented by the general formula () is the monoazo compound represented by the general formula () (In the formula, X represents the above-mentioned meaning.) The amine compound represented by the formula is diazotized by a known method, for example, the method described in Japanese Patent Publication No. 45-11024, and the general formula () (In the formula, Z and R represent the above-mentioned meanings.) It is produced by coupling with a compound shown by the following formula. The amine compound represented by the general formula () can be produced by a known method, for example, the method described in Meliand Textilberichch, Vol. 50, p. 1090 (1969). The compound represented by the general formula () can be produced by a known method, for example, the method described in Japanese Patent Publication No. 47-34680. Specifically, the monoazo compound of the present invention can be produced, for example, as follows. An amine compound represented by the general formula () is dissolved or dispersed in a mineral acid such as sulfuric acid or hydrochloric acid, or an organic acid such as acetic acid or propionic acid, or a mixed solvent thereof. Diazotize using. On the other hand, a compound represented by the general formula () is dissolved in a mineral acid such as sulfuric acid or hydrochloric acid, or an organic acid such as acetic acid or propionic acid, or an organic solvent such as methanol or ethanol, or a mixed solvent thereof. The diazonium compound is added cold, preferably below 10°C, and coupled. After the reaction is completed, the precipitated crystals are separated to obtain a monoazo compound represented by the general formula (). At this time, depending on the case, the pH may be adjusted to 1 or more.
Adjustment to 5 is preferable because coupling occurs quickly. Specific examples of the amine compound represented by the general formula () include the following. 3-amino-5-nitro-2,1-benziisothiazole 3-amino-5-nitro-7-chloro-2,1
-Benzisothiazole 3-amino-5-nitro-7-bromo-2,1
-Benzisothiazole 3-amino-5-nitro-7-methyl-2,1
-Benzisothiazole 3-amino-5-nitro-7-methoxy-2,
1-Benzisothiazole 3-amino-5-nitro-7-ethoxy-2,
1-Benzoyrithiazole Specific examples of the compound represented by the general formula () include the following. 1-(2-hydroxyethyl)-2,2,4,7
-Tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-acetoxyethyl)-2,2,4-trimethyl-7-acetylamino-1,2,3,4
-Tetrahydroquinoline 1-ethyl-2,2,4-trimethyl-7-benzoylamino-1,2,3,4-tetrahydroquinoline The synthetic fibers used in the present invention include polyester fibers, polyamide fibers, and polyolefin fibers. Examples include fibers, cellulose ester fibers, and blends of these fibers. The compound of the present invention exhibits excellent dyeing properties particularly for polyester fibers. When dyeing synthetic fibers using the monoazo compound of the present invention, first, one or more monoazo compounds represented by the general formula () are pulverized into fine particles in an aqueous medium together with a suitable dispersant. crush,
Decentralize. The dispersed dye can be used in liquid form as it is or in powder form by spray drying or the like. Dyeing is done by a method known per se.
A dye bath is prepared by dispersing the dispersed dye in an aqueous medium, and the synthetic fiber is immersed in the dye bath, and heated at 105℃ or higher under pressure.
Preferably, the fabric is dyed at 110-140°C, or at a relatively high temperature, such as boiling water, in the presence of a carrier such as o-phenylphenol or trichlorobenzene, or by padding the dye dispersion onto the fabric.
Dyeing is done by the so-called thermosol dyeing method, which involves drying at 150-230℃ for 30-120 seconds, or in the case of textile printing, the dye dispersion is kneaded with a suitable sizing agent.
This can be applied to cloth and dyed by steaming or thermosol treatment.
Further, a solvent dyeing method using an organic solvent such as trichlorethylene or perchlorethylene as a dyeing medium is also possible. EXAMPLES Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited by these Examples. In the text, parts and % mean parts by weight and % by weight, respectively, unless otherwise specified. Example 1 19.5 parts of 3-amino-5-nitro-2,1-benziisothiazole was dispersed in 97.5 parts of propionic acid/acetic acid (14/16 volume ratio), and 48% nitrosyl sulfate was added while keeping the temperature below 0°C. gradually add the parts. Diazotization is carried out by stirring at the same temperature for 3 hours. on the other hand,
Dissolve 26 parts of 1-ethyl-2,2,4-trimethyl-7-acetylamino-1,2,3,4-tetrahydroquinoline in 100 parts of methanol, and add the diazonium solution to this at 5°C or below. Add while cooling. After this, the pH is adjusted to 4 to 5 and the coupling is completed. The precipitated crystals are separated, washed with water, and dried to form the formula (1). 31.7 parts of a monoazo compound represented by was obtained. Yield 98% λmax 657 nm (in DMF) 3-amino-5-nitro-2,1-benziisothiazole was prepared by the method described in Meliand Textilberichte, Vol. 50, p. 1090, (1969). 1-Ethyl-2,2,4-trimethyl-7-acetylamino-1,2,3,4-tetrahydroquinoline was produced by the method described in Japanese Patent Publication No. 34680/1983. Example 2 1 part of the monoazo compound of formula (1) was atomized and dispersed together with 1 part of a formalin condensate of naphthalene sulfonic acid and 1 part of sodium ligninsulfonate, and this was uniformly mixed with 3 parts of higher alcohol sulfate and 3000 parts of water. Disperse and prepare a dyebath. After immersing 100 parts of polyester processed yarn fabric in this dye bath and dyeing at 130°C for 60 minutes, the dyed product was mixed with 3 parts of caustic soda, 3 parts of hydrosulfite, 3 parts of betaine type amphoteric surfactant, and 3000 parts of water. A reduction cleaning treatment was performed at 85° C. for 10 minutes using a treatment solution consisting of Thereafter, it was washed with water and dried to obtain a dyed product with a high density and vivid green-blue color. This dyed product showed excellent performance in sublimation, light fastness, water fastness, and washing fastness. Example 3 3-amino-5-nitro-2,1-benziisothiazole and 1-pentyl-2,2,4-trimethyl-7-acetylamino-1,2,3,4
A monoazo compound of formula (2) was produced in the same manner as in Example 1 using -tetrahydroquinoline as a raw material. Yield 55% λmax 658 nm (in DMF) Example 4 One part of the monoazo compound of formula (2) was atomized and dispersed with two parts of a formalin condensate of naphthalene sulfonic acid, and the resulting dye composition was mixed into a printing base paste with the following composition. 95
1. Mix well and prepare colored glue. (Material printing paste) 12% Maypro Gum NP60 (Locust Bean Gum) 63 parts Sodium chlorate 0.6 parts Tartaric acid 0.4 parts Water 36 parts Total 100 parts This colored paste was printed on polyester processed yarn fabric,
After drying, it was steamed for 30 minutes using a high-pressure steamer (temperature 130-135°C, gauge pressure 3-4 Kg/cm ² ). Thereafter, it was washed with water, dried, and subjected to reduction washing treatment in the same manner as in Example 2, washed with water, and dried to obtain a dyed product with a clear greenish-blue color with high density. This dyed product showed excellent performance in sublimation, light fastness, and washing fastness. Thereafter, the monoazo compounds shown in Table 1 were synthesized in the same manner as in Example 1, and each was dyed in the same manner as in Example 2 to obtain the results shown in Table 1. In the table, the hue indicates the hue on the polyester fiber.

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Claims (1)

[Claims] 1 General formula () (wherein, (represents a lower alkyl group, an alkenyl group, a cycloalkyl group, or a phenyl group having a benzoyloxy group, a lower alkoxy group, a lower alkylcarbonyloxy group, a lower alkoxycarbonyloxy group, a benzoyloxy group, an anilinocarbonyloxy group, or a benzoyloxy group) A monoazo compound represented by 2 General formula () (wherein, (represents a lower alkyl group, an alkenyl group, a cycloalkyl group, or a phenyl group having a benzoyloxy group, a lower alkoxy group, a lower alkylcarbonyloxy group, a lower alkoxycarbonyloxy group, a benzoyloxy group, an anilinocarbonyloxy group, or a benzoyloxy group) A dyeing or printing method for synthetic fibers, characterized by using a monoazo compound represented by: