JPS60221462A - Monoazo compound and method of dyeing using it - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I [X is H, halogen, lower alkyl, lower alkoxy, or (substituted)aryloxy; Z is halogen, alkyl, acylamino, benzoylamino, lower alkoxy, or alkylsulfonylamine; R<1> and R<2> are H, or alkyl]. EXAMPLE:A compound shown by the formula II. USE:Dye for dyeing or printing synthetic fibers such as polyester, polyamide, etc. in red in improved dyeability, pH stability, build-up properties, fastness to water, washing, sublimation, sunshine, etc. PREPARATION:An amine compound shown by the formula III is diazotized and coupled with a compound shown by the formula IV.

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. Specifically, the present invention provides a water-insoluble monoazo compound and its use,
This invention relates to a method for dyeing synthetic fibers such as polyester fibers and polyamide fibers in red to purple colors.

More specifically, the present invention relates to general formula (I) (wherein X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or an optionally substituted aryloxy group,
2 represents a halogen atom, an alkyl group, an acylamino group, a benzoylamino group, a lower alkoxy group, or an alkylsulfonylamino group; R1 and R2 each independently represent a hydrogen atom or an alkyl group. ) The method for dyeing synthetic fibers characterized by using the monoazo compound shown in the following is a printing method.

In the present invention, lower means preferably having 1 to 4 carbon atoms.

In the compound represented by the general formula (I), ordinarily,
X is preferably a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, or a phenoxy group, and 2 is a halogen group, a methyl group, an acylamino group having up to 4 carbon atoms, a benzoylamino group, or an alkylsulfonylamino group having up to 4 carbon atoms. A group is preferable, and R1 and R2 are preferably a hydrogen atom or a methyl 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 hilt stickiness, and is also resistant to water and washing. It also exhibits excellent fastness against friction, sublimation, and sunlight.

In the present invention, the monoazo compound represented by the general formula (I) is obtained by diazotizing the amine compound represented by the general formula (N) (wherein, X represents the above-mentioned meaning) by a known method. R1, R2, and Z represent the meanings described above, and can be produced by coupling with a compound represented by t).

Alternatively, cyano substitution of a compound represented by the general formula (IV), YZ (wherein, Y is a halogen atom, and X, Z, R1, and R2 represent the above meanings) with copper cyanide. It can also be manufactured by

The compound represented by the general formula (I[) can be produced by a known method, for example, the method described in Japanese Patent Publication No. 47-84680.

Specifically, the monoazo compound of the present invention can be produced, for example, as follows.

The amine compound represented by general formula (II) 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 nitrosyl Diazotize using sulfuric acid. On the other hand, a compound represented by general formula (III) 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 above-mentioned diazonium compound is added to the mixture in a cold state, preferably at a temperature of 10° C. or lower, and coupling is carried out. After the reaction is completed, the precipitated single crystal is separated and the general formula (
A monoazo compound represented by I) is obtained.

Specific examples of the heptamine compound represented by the general formula (2) include the following.

2.6-dicyazaniline 2.6-dicyano-4-chloroaniline 2.6-dicyano-4-bromoaniline 2.6-dicyano-4-methylaniline 2.6-dicyano-4-ethylaniline 2.6
-dicyano-4-methoxyaniline 2,6-dicyano-
4-Ethoxyaniline 2.6-dicyano-4-phenoxyaniline 2.6-dicyate-4-(4-nitrophenoxy)aniline 2.6-dicyate-4-(4-chlorophenoxy)aniline 2.6-dicyano-4-( 3-Methylphenoxy)aniline 2,6-dicyate-4-(2-methoxyphenoxy)aniline Specific examples of the compound represented by the general formula (I[I) include the following.

2.2,4.8-Tetramethyl-1,2,8,4-tetrahydroquinoline 2.2.4-trimethyl-8-chloro-12,8,4-
Tetrahydroquinoline 2.2.4-1-dimethyl-8-ethyl-1°2.8.
4-tetrahydroquinoline 2.2.4-trimethyl-8-acylamino 1.2
, 8.4-tetranodroquinoline 2.2.4-1-dimethyl-8-methylsulfonylamino-1,2,8,4-tetrahydroquinoline 2.2.4-trimethyl-8-benzoylamino-1,
2,3,4-tetrahydroquinoline 2.2.8-trimethyl-1,2,8,4-tetrahydroquinoline 2.2.4-trimethyl-8-methoxy-1°2.8.
The synthetic fibers in the 4-tetrahydroquinoline invention include polyester,
Polyamide-based fibers include alpha fibers, 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 monoazo compound of the present invention, first, one or more monoazo compounds represented by general formula (I) are ground into fine particles in an aqueous medium together with a suitable dispersant. , 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 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 dye is heated at 105°C or higher under pressure.
Preferably, the dyeing is carried out at 110-140°C, or in the presence of a carrier such as 0-phenylphenol or trichlorobenzene at a relatively high temperature, such as boiling water, or the dye dispersion is patched onto the fabric and Dyeing is done by the so-called thermosol dyeing method, which involves dry heat treatment at ~280°C for 80 to 120 seconds, or in the case of textile printing, the dye dispersion is kneaded with a suitable sizing agent, and this is padded onto the fabric.
Dyeing can be done 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.

Next, the present invention will be explained in more detail with reference to actual examples, but the present invention is not limited by these examples. In the text, parts and 俤 mean parts by weight and % by weight, respectively, unless otherwise specified.

Example 1 22.2 parts of 2,6-dicyano-4-furomoaniline was dissolved in 100 parts of 98 sulfuric acid, and after cooling to 0°C,
Add 81.8 parts of tinitosyl sulfate at 5°C or below and add 3 parts at the same temperature.
Diazotize by stirring and keeping warm for a while.

On the other hand, 2,2.4.8-tetramethyl-1゜2.8.4-
18.9 parts of tetrahydroquinoline and 100 parts of methanol
The diazonium solution is added thereto while cooling to below 5°C. The precipitated crystals are separated, washed with water, and dried. 38 parts of the compound of formula (1) was obtained.

λmax: 525 parts m (in dimethylformamide)
Example 2 1 part of the monoazo compound of formula (I), 1 part of formalin condensate of naphthalenesulfonic acid, 1 part of sodium ligninsulfonate
A dye bath is prepared by uniformly dispersing this and 8 parts of higher alcohol sulfate in 8,000 parts of water. After immersing 100 parts of polyester processed yarn fabric in this dye bath and dyeing at 180°C for 60 minutes, the dyed product was mixed with 8 parts of caustic soda, 8 parts of hydrosulfide, 8 parts of betaine, an amphoteric surfactant, water a, ooo. 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 clear bluish red color. This dyed product shows excellent performance in sublimation, light, water and washing fastness.

Example 8 26.5 parts of 2,6-dipromo-4-methylalin are dispersed in 150 parts of 85% hydrochloric acid. After cooling to 0°C, 7 parts of nitrous acid sorter is added and stirred at 0 to 5°C for 8 hours to diazotize.

On the other hand, 2,2,4-1-limethyl-8-chloro-1,2,8
, 20.9 parts of 4-tetrahydroquinoline were dissolved in 100 parts of methanol, and 5 parts of the diazonium solution was added thereto.
Add while cooling to below 10°C. Separate the precipitated crystals, wash with water, and dry. 42.5 parts of a compound represented by formula (2) was obtained. Next, equation (2)
1 part and 7 parts of the monoazo compound were mixed with 50 parts of dimethylformamide.
Cyanide was added to 6 fJ of cupric cyanide and stirred at room temperature for 5 hours. The filtered T solution was diluted with methanol to precipitate crystals, separated, washed with water and dried. do.

Formula (3) 2.9 parts of the compound represented by 1 were obtained.

λmar: 514 parts m (in dimethylformamide) Practical example 4 1 part of the monoazo compound of formula (3) was co-dispersed into fine particles with 2 parts of a formalin condensate of naphthalene sulfonic acid, and the resulting dye composition was prepared as follows. Add to 95 parts of the original printing paste and mix well to prepare colored paste.

(Material paste for printing) Sodium chlorate 0.6 parts Liquor Stone acid 0.4 parts Water 36 parts Total 100 parts This color paste is printed on polyester processed yarn fabric, and after drying,
High pressure steamer (temperature 180~185℃, gauge pressure 8~
4) Steam for 80 minutes. After this,
After washing with water and drying, a reduction washing treatment was performed in the same manner as in Example 2, followed by washing with water and drying to obtain a highly concentrated and vivid red dyed product. This dyed product exhibits excellent fastness to sublimation, light, water, and washing.

Example 5 The monoazo compounds shown in Table 1 were synthesized in the same manner as in Example 1 or 8, and each was dyed in the same manner as in Example 2 to obtain the results shown in Table 1. In the table, the color tone indicates the hue on the polyester fiber.

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Claims (2)

[Claims] (1) General formula (I) (wherein, group, benzoylamino group, lower alkoxy group or 1
This represents an alkylsulfonylamino group, and R1 and R2 each independently represent a hydrogen atom or an alkyl group. ) A monoazo compound represented by (2) General formula (I) (wherein, Dyeing of synthetic fibers characterized by using a compound represented by a benzoylamino group, a lower alkoxy group or an alkylsulfonylamino group, R1 and R2 each independently represent a hydrogen atom, and d represents an alkyl group. Or the printing method.