JPS5924755A - Monoazo compound and dyeing method using same - Google Patents

Abstract

NEW MATERIAL :Monoazo compounds of formula I wherein X is H, halogen, lower alkyl, nitro, lower alkoxy, lower alkylsulfonyl, cyano; Z is H, halogen, alkyl, acylamino, benzoylamino, alkylsulfonylamino; R1, R2, R3, R4 are each H, alkyl; R5 is H, alkyl, alkenyl, cycloalkyl, aralkyl, phenyl. USE:Dyes which can dye or print synthetic fibers such as polyester fiber or polyamide fiber blue with excellent fastness to water, washing, rubbing, sublimation, sunlight, etc. PREPARATION:An amine compd. of formula I is diazotized and then coupled with a compd. of formula III to produce the monoazo compd. of formula I .

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. The present invention relates to a water-insoluble monoazo compound and a method for dyeing or printing synthetic fibers such as polyester fibers 11 and polyamide fibers in blue using the water-insoluble monoazo compound.

In other words, the expression ψ is defined by the general formula (It (where X is a hydrogen atom, a halogen atom, a lower alkyl group, a nitro group, a lower alkoxy group, a lower alkylsulfonyl group, and -
cyano group, Z is a hydrogen atom, halogen Fj (child, alkyl group, anlylamino group, benzoylamino group or argylsulfonylamino group) each independently represents a hydrogen atom or an alkyl group, l(,
6 represents a hydrogen atom, an alkyl group, a substituted alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, or a phenyl group. ) and a method for dyeing or printing synthetic fibers using the same.

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

In compounds of the general formula tIl, advantageously X
is preferably a hydrogen atom, a methyl group, a methoxy group, a chlorine atom, or a bromine atom, and Z is a hydrogen atom, a halokun group, a methyl group,
Acylamino group having 4 or less carbon atoms, benzoylamino group,
An alkylsulfonylamino group having 4 or less carbon atoms is preferable, and lNlI+t2, rt3, and R4 are preferably hydrogen atoms and methyl groups. The rear ZL. It also did not show excellent performance in terms of fastness.

In the present invention, the monoazo compound represented by the general formula (I) is obtained by preparing an amine compound represented by the general formula (wherein,
Diazotization was carried out by the method described in Japanese Patent No. 5-80584, and the general formula (It4 It3 (where Z, IJ, R2, R3, It4,
It5 represents the meaning of the Book of Hari. ) by coupling with a compound represented by
J.J. , I can do blue.

The compound represented by the general formula (Machi) can be produced by a known method, for example, the method described in 11 of Japanese Patent Publication No. 47-84680. Specifically, the monoazo compound of the present invention can be produced by, for example, the following method. It can be manufactured by

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, preferably at 5°C when cooled.
Diazotization is performed using nitrosyl sulfate below. On the other hand, a compound represented by the general formula fllll is dissolved in a mineral acid such as sulfuric acid or hydrochloric acid, an organic acid such as acetic acid or propionic acid, an organic solvent such as methanol or ethanol, or a mixed solvent thereof, and the The diazonium compound is added cold, preferably below 10° C., and coupled. After the reaction is completed, the precipitated crystals are separated from each other to obtain a monoazo compound represented by the general formula 〇1. At this time, depending on the case, it is preferable to adjust the pH to 1 to 5 because coupling occurs quickly.

Specific examples of the amine compound represented by the general formula (11) include the following.

2-amino-ni-nitropenzothiazole 2--/'mi/-4-10-6-2]-lobensote'azole 2-amino-4-furomo-6-nitrobenzothiazole 2-amino-4-methyl-6 − Nitropenzothiazo・−
2-amino-4-methoxy-6-nitrobenzothiazole 2-amino-4-methylsulfonyl-6-nitrobenzothiazole 2-amine-4-cyano-6-nitrobenzothiazole 2-amino-4.6- Cinitropenzothiazole 2-amino-4-ethoxy-6-nitrobenzothiazole - The compound represented by the general formula (1) is specifically i
, can be given as follows.

1.2,8.4-Tetrahydroquinoline 2.2.4-
1-trimethyl-1,2,8,4-tetrahydroquinoline 1-ethyl-2,2,4-trimethyl-1,2,8,4
-Tetrahydroquinoline/ l-tutil-2.7-dimethyl-1.2,8゜4-tetrahydroquinoline 1-(2-hydroxyethyl)-2,2,4゜7-detramethyl-1.2,8.4 -Tetrahydrogynoline 1-(2-zooanoethyl)-2,2,4-trinotero-7-lyalo1,2,8.4-tetrahydroquinoline 1-bennyl72.7-dimethyl-1.2,3. 4-atrahydroquinoline 1-cyclohexyl-2,2,4-trimethyl-1,2
,8,4-tetrahydroquinoline 1-ethyl-2,2
,4-trimethyl-1,218,4-tetrahydro'
Quinoline 1-allyl-2,2,4-1-dimethyl-1,2,3+
4-tetrahydroquinoline 1-(2-acetoxyethyl)-2,2,4-trimethyl-7-acetylamino-1,2゜3.4-tetrahydroquinoline l-globil-2,2,4 -Trimethyl-7-methylsulfonylamino-1,2,8,4-tetrahydroquinoline 1-ethyl-2,2,4-1-dimethyl-7-penzoylamino-1,2,8,4-tetrahydroquinoline ■-7enethyl-2.4.8-1-limethyl-7-probionylamino-1,2,8,4-tetrahydroquinoline The synthetic fibers in the present invention include polyester,
Examples include polyamide fibers, polyolefin fibers, lerulose ester fibers, and blends of these fibers.

The compound of the present invention exhibits excellent J1/l1% color properties particularly for polyester fibers.

When dyeing synthetic fibers using the monoazo compound of the present invention, first, one or more monoazo compounds shown in the general formula are ground into fine particles in an aqueous medium with an appropriate dispersant, and then dispersed. to become The dispersed dye can be used as it is in liquid form or in powder form by spray drying or the like. Dyeing is done by a method known per se, in which the dispersed dye is separated into an aqueous medium, the dye bath is discarded, and synthetic fibers are produced. Dip and dye under pressure at 105° C. or higher, preferably 110 to 140° C., or dye at a relatively high temperature, for example, water at a relatively high temperature in the presence of a carrier such as ()-phenylphenol or trichlorobenzene. Dye it with or patten the dye separation solution on the cloth, 150 ~
Dyeing is done using the so-called Leemosol dyeing method, which involves drying f2 at 230°C for 30 to 120 seconds, or d1 in the case of textile printing.
Dyeing can be carried out by kneading the dyed PI-dispersion with a suitable glue, padding the cloth with a strainer, and subjecting it to steaming or thermosol treatment. Further, a solvent dyeing method using an organic solvent such as trichlorethylene or perk ethylene as a dyeing medium is also OJ' capable.

Next, the present invention will be explained in more detail based on Examples, but the present invention is not limited by these Examples.
do not have. In the text, parts and 96 mean parts by weight and mold set 96, respectively, unless otherwise specified.

Example 1 19.5 parts of 2-amino-6-nitrobenzothiazole was fractionated into 97.5 parts of 8596 phosphoric acid, and after cooling to 0°C, 7.0 parts of a bent nitric acid leader was added at 7.0 parts of 'tO'c or less, Diazotization is carried out by stirring at the same temperature for 8 hours. On the other hand, 1-ethyl-2,2,4-)limethyl-7-'acetylamino-
26.0 parts of 1,2,8,4-tetrahydroquinoline is dissolved in 100 parts of methanol, and the above-mentioned diazonium dissolution is added thereto while cooling to 5°C or less. After this, the pH
Discard coins on gold 4-5 and end the coupling. The precipitated crystals were separated, washed with water, and dried to obtain 32.7 parts of monoazo compound 113 represented by formula (1).

Yield 7096 1-Ethyl-2,2,4-trimethyl-7-ahitylamino-1.2.8.4-tetrahydroquinoline was produced by the method described in Japanese Patent Publication No. 47-t4aso. did.

Example 2 1 part of the monoazo compound of formula (1), 1 part of formalin condensate of 7talenes sulfonic acid, 1 part of lignin sulfonic acid sorter
Atomized with part, this and higher alcohol l+il
8 parts of E acid ester was mixed with water a, o o.

Make a dye bath of Jl by uniformly distributing one piece on each section. 100 parts of polyester processed yarn fabric was immersed in this dye bath and heated to 180°C.
After dyeing for 60 minutes, the dyed product was mixed with 3 parts of soda, 3 parts of hydrosulfite, 8 parts of betaine type surfactant, and water a, oo.

A photocleaning treatment was performed at 85° C. for 10 minutes using a treatment solution consisting of 100% of the total amount of water. After that, it was washed with water and dried to obtain a highly concentrated and clear green-blue dyed product.
It showed excellent fastness to water and washing.

Example 8 Example 1 and 2-amino-6-nitrobenzothiazole and l-benzo-2.2.4-t-limethyl-7-acetylamino-1,2,8.4-tetrahydroquinoline were used. Similarly, a monoazo compound of formula (2) was produced.

113 Yield 68% Example 4 1 part of the monoazo compound of formula (2) was atomized and dispersed with 2 parts of a formalin condensate of naphthalene sulfonic acid, and the obtained dye composition was added to 95 parts of a printing base paste having the following composition. Mix well and prepare colored paste.

(Material paste for printing) Sodium acid 0.6 parts Liquor Stone Acid 0.4 parts Total
100 parts of this colored paste was printed on a polyester-added two-thread fabric, and after drying, it was heated in a high-pressure steamer (temperature 180-185°C, gauge pressure 3-41) for 8 hours.
0 minute steamy/gu self. 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 fastness to vinegar, sunlight, water, and washing.

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 is the hue on polyester fiber Kanekosu 0.

Claims (2)

[Claims] (1) General formula (in the formula, group, acylamino group, benzoylamino group 1
Da is alkylsul small nylamino group + t1.112,
It3 and 11.4 each independently represent an alkyl group spanning a hydrogen atom, and 几5 represents a hydrogen atom, an alkyl group, a substituted alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, or a phenyl group. ) A monoazo compound shown at 8°. (2) General formula (in the formula, atom, alkyl group, acylamino group, benzoylamino group or alkylsulfonylami] group, river, IL2.It
3. n and each independently represent a hydrogen atom or an argyl group, and R5 represents a hydrogen atom, a pregyl group, a substituted alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group or a phenyl group. ) A method for dyeing or printing synthetic fibers, characterized by using a compound represented by: