JPH0472863B2 - - 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 bright red using the same. That is, the present invention provides the general formula () (In the formula, X is an alkyl group, cyano, hydroxy,
an alkyl group, an alkenyl group, an aralkyl group, or a tetrahydrofurfuryl group substituted with lower alkoxy, phenoxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylcarbonyloxy, or tetrahydrofurfuryloxy; Y is a hydrogen atom, a halogen atom, or a lower alkyl group; group, lower alkoxy group, acylamino group, benzoylamino group or alkylsulfonylamino group, Z is hydrogen atom, alkyl group, cyano, hydroxy, lower alkoxy, phenoxy, benzyloxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylcarbonyloxy , lower alkoxycarbonyloxy, phenoxycarbonyl, benzoyloxy, cyanoethyloxy,
It represents an alkyl group, alkenyl group, cycloalkyl group, aralkyl group or phenyl group substituted with lower alkylcarbonylamino, lower alkoxyalkoxy, phenylaminocarbonyloxy or benzylcarbonyloxy. ) A method for dyeing or printing synthetic fibers characterized by using the monoazo compound shown in the following. In the present invention, "lower" means having 1 to 4 carbon atoms. In the compound represented by the general formula (), Y is preferably a hydrogen atom, a chlorine atom, a methyl group, a lower acylamino group, a benzoylamino group, a lower alkylsulfonylamino group, and Z is an alkyl group having 1 to 8 carbon atoms. , an allyl group, a benzyl group, a phenethyl group, and a substituted alkyl group having a phenyl ring are preferred. 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. or,
It is noteworthy that when the substituent Z in the general formula () is a substituted alkyl group or an aralkyl group having a phenyl ring, it has even better performance in sunlight fastness. In the present invention, the monoazo compound represented by the general formula () is the monoazo compound represented by the formula () The amine compound represented by is diazotized by a known method to form the general formula () (In the formula, Y and Z represent the above meanings.) General formula () obtained by coupling with a compound represented by (In the formula, Y and Z represent the above-mentioned meanings.) It can be produced by substituting the hydrogen atom of the imidazole ring of the monoazo compound shown by the following with an X group. Specifically, the monoazo compound of the present invention can be produced, for example, as follows. The amine compound represented by the 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, and the amine compound is dissolved or dispersed in a nitrous acid solution when cold, preferably at 5°C or below. Diazotize with soda or nitrosyl sulfate.
On the other hand, the compound represented by the general formula (), sulfuric acid,
The diazonium compound is dissolved in a mineral acid such as hydrochloric acid, an organic acid such as acetic acid or propionic acid, or an organic solvent such as methanol or ethanol, or a mixed solvent thereof, and the diazonium compound is added thereto preferably at 10%
Add at below ℃ and couple. At this time, depending on the case, it is preferable to adjust the pH to 1 to 5 because coupling occurs quickly. After the reaction is completed, the precipitated crystals are separated, washed with water, and dried to obtain a monoazo compound represented by the general formula (). The compound represented by the general formula () thus obtained is alkylated using an alkylating agent in an inert organic solvent, water, or a water-organic solvent to obtain a compound represented by the general formula (). As the alkylating agent, halogen compounds, toluenesulfonic acid esters, and alkylene oxides are preferred. Specific examples of the compound represented by the general formula () include the following. 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline 1-ethyl-2,2,4-trimethyl-1,2,
3,4-tetrahydroquinoline 1-butyl-2,2,4-trimethyl-1,2,
3,4-tetrahydroquinoline 1-(2-hydroxyethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline 1-(2-cyanoethyl)-2,2,4-trimethyl-1 , 2,3,4-tetrahydroquinoline 1-(2-acetoxyethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline 1-benzyl-2,2,4-trimethyl-1,
2,3,4,tetrahydroquinoline 1-cyclohexyl-2,2,4-trimethyl-
1,2,3,4-tetrahydroquinoline 1-allyl-2,2,4-trimethyl-1,2,
3,4-tetrahydroquinoline 1-phenethyl-2,2,4-trimethyl-1,
2,3,4-Tetrahydroquinoline 1-propyl-2,2,4-trimethyl-7-chloro-1,2,3,4-tetrahydroquinoline 1-(2-phenoxyethyl)-2,2,4-trimethyl- 7-acetylamino-1,2,3,4-
Tetrahydroquinoline 1-(2-benzoyloxyethyl)-2,2,
4,7-tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-phenylcarbamoyloxyethyl)-
2,2,4-trimethyl-7-benzoylamino-1,2,3,4-tetrahydroquinoline 1-(2-benzyloxyethyl)-2,2,4,
7-tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-methoxycarbonyloxyethyl)-
2,2,4-trimethyl-7-methylsulfonylamino-1,2,3,4-tetrahydroquinoline 1-(2-methoxycarbonylethyl)-2,2,
4-trimethyl-7-ethyl-1,2,3,4-
Tetrahydroquinoline 1-(2-benzylcarbonyloxyethyl-2,
2,4,7-trimethyl-1,2,3,4-tetrahydroquinoline 1-phenethyl-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-phenoxyethyl) -2,2,4,7-
Tetramethyl-1,2,3,4-tetrahydroquinoline 1-amyl-2,2,4-trimethyl-7-propionylamino-1,2,3,4-tetrahydroquinoline 1-hexyl-2,2,4- Trimethyl-7-methoxy-1,2,3,4-tetrahydroquinoline 1-(2-propionyloxyethyl)-2,2,
4,7-tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-carbamoylethyl)-2,2,4-trimethyl-7-chloro-1,2,3,4-tetrahydroquinoline 1- (2-allyloxyethyl)-2,2,4-trimethyl-7-acetylamino-1,2,3,4-
Tetrahydroquinoline 1-(3-methoxypropyl)-2,2,4-trimethyl-7-ethoxy-1,2,3,4-tetrahydroquinoline The synthetic fibers in the present invention include polyester fibers, polyamide fibers, Examples include polyolefin 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 compound of the present invention, one or more monoazo compounds represented by the general formula () are first ground into fine particles in an aqueous medium together with a suitable dispersant. and decentralize it. The dispersed dye can be used as a liquid or as a powder by spray drying. Dyeing is carried out by a method known per se, in which a dispersed dye is dispersed in an aqueous medium to prepare a dye bath, the synthetic fiber is immersed, and the dyeing process is carried out under pressure at 105°C or higher, preferably at 110 to 140°C.
dyeing at a relatively high temperature, e.g. boiling water, in the presence of a carrier such as O-phenylphenol or trichlorobenzene, or by plating the dye dispersion onto the fabric and dyeing at 150-230°C for 30-30°C.
Dyeing is done using the so-called thermosol dyeing method, which involves dry heat treatment for 120 seconds, or in the case of textile printing, the dye dispersion is kneaded with a suitable sizing agent, this is patched onto the fabric, and dyed by steaming or thermosol treatment. It can be carried out. Furthermore, a solvent dyeing method using an organic solvent such as trichlorethylene or perchloroethylene 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 2-amino-4,5-dicyanoimidazole
Disperse 13.3 parts in 330 parts of water and 32 parts of concentrated hydrochloric acid.
After cooling to 5°C, add 7 parts of sodium nitrite (14%
50 parts of aqueous solution) is added at 0-5°C. The reaction was carried out at the same temperature for 1 hour to complete the diazotization. On the other hand, 1-ethyl-2,2,4-trimethyl-
20.3 parts of 1,2,3,4-tetrahydroquinoline are dissolved in 100 parts of acetic acid, and the above diazonium solution is added thereto at 0-5°C. Separately, the precipitated crystals were washed with water and dried, and the formula (1) was obtained. 31.2 parts (yield 90%) of the compound represented by was obtained. Next, 17.4 parts of the compound of formula (1) was dissolved in 200 parts of dimethylformamide, 15.4 parts of diethyl sulfate and 6.4 parts of sodium carbonate were added, and the mixture was reacted at 60°C for 10 hours. After completion of the reaction, the precipitated crystals were separated into 1000 parts of water, washed with water, and dried to obtain the formula (2). 15.0 parts (yield: 80%) of the compound shown was obtained. λmax (90% DMF) 544 nm Example 2 1 part of the monoazo compound of formula (2) is atomized and dispersed together with 1 part of formalin condensate of naphthalene sulfonic acid and 1 part of sodium lignin sulfonate, and this and 3 parts of higher alcohol sulfuric ester are dispersed. A dyebath is prepared by uniformly dispersing the mixture in 3000 parts of water. 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. Reduction treatment was carried out at 85°C for 10 minutes using a treatment solution consisting of Thereafter, the dyed product was washed with water and dried to obtain a highly concentrated and vivid red dyed product.
This dyeing showed excellent performance in sublimation, sunlight, water and washing fastness. Example 3 2-amino-4,5-dicyanoimidazole
Disperse 13.3 parts in water, 330 parts water and 32 parts concentrated hydrochloric acid. After cooling to 5°C, 7 parts of sodium nitrite are added at 0-5°C. Diazotization is completed by reacting at the same temperature for 1 hour. On the other hand, 1-(2-phenoxyethyl)-2,2,
30.9 parts of 4,7-tetramethyl-1,2,3,4-tetrahydroquinoline is dissolved in 200 parts of methanol, and the diazonium solution is added thereto at 0-5°C. After stirring at the same temperature for 3 hours, the precipitated crystals were separated, washed with water, and dried to form the formula (3). 38.5 parts (yield 85%) of the compound represented by was obtained. Next, 22.7 parts of the compound of formula (3) are dissolved in 300 parts of N-methylpyrrolidone, 5.2 parts of potassium carbonate are added, and then 5.7 parts of chloroacetonitrile is added dropwise at 80°C. After reacting at the same temperature for 10 hours, it was distilled into 1000 parts of water, and the precipitated crystals were separated, washed with water, dried, and the formula (4) was obtained. 17.2 parts (yield 70%) of the compound represented by was obtained. λmax (90% DMF) 515 nm Example 4 1 part of the compound of formula (4) was atomized and dispersed with 2 parts of a formalin condensate of naphthalene sulfonic acid, and the resulting dye composition was added to 95 parts of a printing base paste with the following composition. In addition,
Mix well to prepare colored glue. (Material printing paste) 12% Maypro Gum NP-60 (Locust Bean Gum) 63 parts Sodium chlorate 0.6 parts Tartaric acid 0.4 parts Water 36 parts 100 parts This color paste was printed on polyester processed thread 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, subjected to a reduction washing treatment in the same manner as in Example 2, washed with water, and dried to obtain a highly concentrated and vivid red dyed product. This dye is
It showed excellent performance in sublimation, sunlight, water 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. The hues in Table 1 are the hues on polyester fibers.

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Claims (1)

[Claims] 1 General formula () (In the formula, X is an alkyl group, cyano, hydroxy,
an alkyl group, an alkenyl group, an aralkyl group, or a tetrahydrofurfuryl group substituted with lower alkoxy, phenoxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylcarbonyloxy, or tetrahydrofurfuryloxy; Y is a hydrogen atom, a halogen atom, or a lower alkyl group; group, lower alkoxy group, acylamino group, benzoylamino group or alkylsulfonylamino group, Z is hydrogen atom, alkyl group, cyano, hydroxy, lower alkoxy, phenoxy, benzyloxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylcarbonyloxy , lower alkoxycarbonyloxy, phenoxycarbonyl, benzoyloxy, cyanoethyloxy,
It represents an alkyl group, alkenyl group, cycloalkyl group, aralkyl group or phenyl group substituted with lower alkylcarbonylamino, lower alkoxyalkoxy, phenylaminocarbonyloxy or benzylcarbonyloxy. ) A monoazo compound represented by 2 General formula () (In the formula, X is an alkyl group, cyano, hydroxy,
Alkyl group, alkenyl group, aralkyl group or tetrahydrofurfuryl group substituted with lower alkoxy, phenoxy, lower alkenyloxy, lower alkoxycarbonyl, lower alkylbonyloxy or tetrahydrofurfuryloxy, Y
is a hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group, acylamino group, benzoylamino group or alkylsulfonylamino group, Z is a hydrogen atom, alkyl group, cyano, hydroxy, lower alkoxy, phenoxy, benzyloxy, lower alkenyloxy , lower alkoxycarbonyl, lower alkylcarbonyloxy, lower alkoxycarbonyloxy, phenoxycarbonyl,
It represents an alkyl group, alkenyl group, cycloalkyl group, aralkyl group or phenyl group substituted with benzoyloxy, cyanoethyloxy, lower alkylcarbonylamino, lower alkoxyalkoxy, phenylaminocarbonyloxy or benzylcarbonyloxy. ) A dyeing or printing method for synthetic fibers, characterized by using a monoazo compound represented by: