JPH01165A - Monoazo compound and method for dyeing or printing textile materials using the same - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a monoazo compound and a method for dyeing or printing textile materials using the same.

More specifically, the present invention relates to a monoazo compound, and a method for dyeing or printing using this as a fiber-opening reactive dye, covalently bonding the monoazo compound to an Arotoru fiber dye capable of forming a covalent bond.

Conventional technology Generally, phenylazobenzene-based reactive dyes are pyrazolone-based or pyridone-based reactive dyes of the same color! P! It is widely used because it is superior in terms of fastness and color value compared to other materials.

Problems to be Solved by the Invention However, it cannot be said that these reactive dyes have the performance to meet all the needs of the demanding industry. The development of reactive dyes is still desired.

Means for Solving the Problems For these reasons, the inventors of the present invention have made extensive studies and have found that a novel monoazo compound can satisfy the above-mentioned needs, and have completed the present invention.

The present invention solves the above problem by optimally combining a substituent on the phenylazobenzene or azonaphthalene skeleton that serves as a dye matrix, and a linking group that connects the so-called vinyl sulfone group, which is a fiber-reactive group, to the pigment matrix. This is an attempt to resolve the issue.

That is, the present invention provides the following general formula (1) [wherein,
RI is hydrogen, halogeno, C1-4 alkyl% CIMJ alkoxy, ureido or acylamino, Rx is hydrogen, or RI and R1 can form a benzene ring! tree,
and may have sulfo on the same ring, Rs is water i
, Cs~4 alkyl, C! ~4 alkoxy or sulfo,
R4 and Rs are independently hydrogen or optionally substituted alkyl, Bl and B, 1 are independently hydrogen, methyl, methoxy, ethyl, ethoxy, chloro, bromo,
Phenylene optionally substituted by sulfo or carboxy, or naphthylene optionally substituted by sulfo, Yl and Yl independently of each other -CH*CH
嘗L (L is a group that is eliminated by the action of an alkali) or vinyl, and A represents phenyl having at least one water-soluble group. ] The present invention provides a monoazo compound represented by the following and a method for dyeing or printing fiber materials using the monoazo compound.

In the general formula (I), when R1 is acylamino, the acyl is COCl~4alkyl or -COC*~4alkenyl (these alkyls and alkenyls are substituted with substituents such as sulfo, carboxy, and 'halogeno). benzoyl which may be substituted with a substituent such as sulfo, carboxy, methyl or halogeno. Preferred R1 is hydrogen, methyl, methoxy, ureido or acetyl, propionyl,
-COC is H4C0OH, C0CH=CHC0OH or amino substituted with benzoyl, or RI
and R1 form a benzene ring and have one sulfo group on the ring.

When R1 is C1-4 alkyl or alkoxy,
The carbon chain may be straight or branched, and may have a substituent such as chloro or hydroxy, but preferably has a small number of carbon atoms, particularly methyl and methoxy.

The best combination of R1, Rj and Rs is that R1 is hydrogen,
Chloro, methyl, methoxy, ureido or acetyl, propionyl, C0Cz Ha C0OH.

-C0CH=CHC0OH or amino substituted with benzoyl, and 9 is hydrogen, or forms a benzene ring with RIR* and has one sulfo on the ring, and 9 is hydrogen , methyl or methoxy.

When R4 or 2 are alkyl which may be substituted independently of each other, such a group is described, for example, in JP-A-59-1999.
The groups shown in JP 122549 are suitable, preferably methyl and ethyl.

It is preferred that at least one of R4 and Rs is hydrogen.

As for BS or By, examples of optionally substituted phenylene groups and naphthylene groups correspond to the groups shown in the same publication, of which B+ and BS are independently substituted with a methyl group or a methoxy group. A phenylene group, which may be an optional phenylene group, is preferable.

When Yl or Y2 is -CH5CHtL, groups known to be able to be eliminated by the action of an alkali are suitable, such as sulfate, thiosulfate, acetoxy and chloro. Preferred Yl
and Y2 are both β-sulf-1-toethyl, and some 'nyl may be mixed therein.

At least 1 represented by A in the general formula (Il)
Phenyl having two water-soluble groups preferably has the following general formula [wherein R and R2 independently represent hydrogen, chloro, methyl or methoxy, m represents 0 or 1, n represents 1 or 2, and m+n is 1 or 2. ] It is phenyl represented by the above general formula (Il is preferably a monoazo compound of the following general formula aI in the form of a free acid) [in the formula I B! H&HR
1""RF," jn, Y+, Y! have the above-mentioned meanings.]

Furthermore, particularly preferred monoazo compounds include the following in the form of free acids:
u is hydrogen or R1 is methyl; t) Rh
is methoxy and Ru is hydrogen, methyl or ethyl. ] It is a monoazo compound shown by.

These monoazo compounds are preferably salts of alkali metals or alkaline earth metals, particularly sodium or potassium salts.

The compounds of the present invention have the following formulas (IT), (V), (VI
), and (IV) (V)
(■l) (■) [In the formula, A, B+, By, R+~Ra, Y+ and Y! has the meaning given above. ] It can be synthesized by a conventional method using the compound shown below and cyanuric chloride.

Examples of the compound of formula (■) include aniline-2,3 or 4-sulfonic acid, 2-amino-4 or 5-sulfobenzoic acid, 4-amino-2-sulfo-benzoic acid, 4-methyl- Aniline-2 or 3-snowonic acid, 2-methyl-7
Niline-4 or 5-sulfonic acid, 2 or 4-amino-benzoic acid, 2-methoxy-aniline-4 or 5-sulfonic acid, 4-methoxy-aniline-2 or 8-sulfonic acid,
2-Methyl-5 or 6-chloro-aniline-4-sulfonic acid, 2-methyl-4-chloro-aniline-5 or 6-
Sulfonic acid, 4-chloro-5-methylaniline-2-sulfonic acid, aniline-2,4,2,5 or 8.5-disulfonic acid, 2-methylaniline-8,5,4,5 or 4
．． Examples include 6-disulfonic acid and 4-methylaniline-2,5-disulfonic acid.

Compounds of formula M include, for example, m-anisidine, 8-methyl or ethylaniline, 2,5-xylidine, 2-ethyl-5-methylaniline, 2-methoxy-5-methyl or ethylaniline, 2-ethoxy-5 -Methyl or ethylaniline, 8-aminoacetanilide, 8-amino-4-methyl or ethylacetanilide, 8-amino-
4-Methoxy or ethoxyacetanilide, 8-succinylamino or maleylaminoaniline, 2-methyl-5-succinylamino or maleylamino, =phosphorus, 8-benzoylaminoaniline, 2-methyl-5-
Benzoylaminoaniline, or a compound having chloro, methyl, nitro, sulfo or carboxy as a substituent at the o-lm- or p-position on these benzoyls 2, 5 +-dimethoxyaniline, 8-7 minophenyl urea, 1 Mention may be made of -naphthylamine-6-17- or 8-sulfonic acid, 2-methoxy-1-naphthylamine-6-17- or 8-sulfonic acid.

The starting compounds described above can be used in reaction conditions such as acids and/or salts,
In particular they are used in the form of alkali metal or alkaline earth metal salts.

The monoazo compound produced according to the present invention can be made into a liquid product by removing the inorganic salt and adding a stabilizer or dyeability improver as necessary, or the monoazo compound or the reaction solution can be made into a liquid product. It can be made into a powder product by evaporation, for example by pressure drying, and it can also be made into a liquid or powder product through salting out separation by addition of wt silica using a generally known method.

The monoazo compounds according to the invention can be used as fiber-reactive dyes for dyeing textile materials, such as materials containing hydroxy groups or carboxylic acid amide groups.

Hydroxy group-containing materials are natural or synthetic hydroxy group-containing materials, such as cellulose fiber materials or their regenerated products and polyvinyl alcohol. Preferably, the cellulosic rutted silk material is cotton, but also other vegetable wefts such as linen, hemp, jute and ramie. Regenerated cellulose Pa fibers are, for example, viscose stable and filament viscose.

Carbonamide group-containing materials are, for example, synthetic and natural polyamides and polyurethanes, especially in the form of fibers, such as wool and other animal hairs, silk, leather, polyamide-6,6
, polyamide-6, polyamide-11 and polyamide-
It is 4.

For dyeing, methods depending on the reactive group of the fiber-reactive dye can be applied.

For example, in the case of cellulose-based pigeon fiber, the dye of the present invention and W1 binder 1, such as caustic soda, sodium carbonate, phosphate,
Staining is carried out using silicates or sodium bicarbonate. The dyeing method is #! The method can be selected depending on the nature and physical shape of the material, and for example, an exhaust method, a printing method, a cold patch method, a taper method, etc. can be adopted.

In the case of exhaustion method, sodium carbonate, trisodium phosphate,
It is carried out at relatively low temperatures in a dye bath containing mirabilite or common salt in the presence of an acid binder such as caustic soda. In the case of P dyeing, thickening agents or emulsifying thickening agents such as sodium alginate or starch ether and sodium carbonate, sodium bicarbonate, caustic soda, sodium triphosphate, sodium trichloroacetate or corresponding potassium or alkaline earth compounds are used. with alkaline or alkali-releasing dyes, if desired with the addition of customary printing aids or dispersants, such as urea, on the fibers, drying and heat treatment, especially in the presence of water vapor. It can be dyed by applying it to. In the case of cold-pad-patch-up dyeing, caustic soda alone or in combination with sodium silicate, sodium carbonate or trisodium phosphate is used as the acid binder, optionally with the addition of Glauber's salt or common salt, and if desired with the addition of urea or the like. It is padded onto fibers at room temperature with the addition of solubilizers or penetrants, rolled up into rolls,
Dyeing can be done by leaving it for 3 hours or overnight, washing with water, and drying.

The compound of the present invention is characterized in that it exhibits excellent performance on m-line materials, and is particularly suitable for dyeing cellulose fibers. It exhibits high exhaustion and fixation rates, excellent build-up properties, level dyeing properties, and washability, and even slight fluctuations in dyeing conditions such as temperature, bath ratio, salt concentration, etc. have little effect on dyeability. In addition to having the characteristics of no lint, it also has excellent light resistance, sweat resistance, light resistance, perspiration resistance, acid hydrolysis resistance, washing resistance, chlorine resistance, etc.

Next, the present invention will be explained in more detail with reference to Examples. In the text, the part indicates 1Itffi part.

Example 1 Aniline-2,5-disulfonic acid 12.7
diazotized and coupled with 7.6 parts of 3-aminophenyl urea, followed by 9.28 parts of Schifnu A chloride;
Furthermore, 14.1 parts of 1-aminobenzene-4-β-sulfatoethyl sulfone was sequentially condensed, and finally 14 parts of 1-aminobenzene-3-β-sulfatoethyl sulfone
．． One part was reacted at pH 4-5.60-70°C. By salting out with sodium chloride, a monoazo compound represented by the following formula (%) was obtained in the form of free n-acid.

Add 0.8 parts of this monoazo compound to 200 parts of water, add 1 part of cotton
Add 0f and 8 parts of Glauber's salt, raise the temperature to 60℃, add 4 parts of sodium carbonate, dye at the same temperature for 1 hour, wash, and sow pink to obtain yellow dyeing with excellent fastness and dyeing performance as noted in frIr. I got something. Although the dyeing temperature, bath ratio, and salt concentration of this compound were slightly changed, the reproducibility was excellent. -Aminobenzene-
In place of 4-β-sulfatoethylsulfone and 1-aminobenzene-8-β-sulfatoethylsulfone, A411 (formula @) compound), Bm (formula ■ compound), CM (formula □□□ compound and D&(8■) compound)
Using the same method, a monoazo compound corresponding to the valley was obtained and dyed to obtain a dyed product having the tone shown in E-buttock. These compounds showed the performance described above.

Example 8 Aniline-2,5-disulfonic acid t2.7 was prepared by a conventional method.
part was diazotized and coupled with 11.5 parts of 8-aminoacetanilide-4-sulfonic acid, followed by 9.28 parts of cyanuric chloride and a further 14 parts of 1-aminobenzene-4-β-sulfatoethylsulfone. One part is sequentially condensed,
Finally, 14.1 parts of 1-aminobenzene-8-β-sulf-1-toethylsulfone was reacted at pH 4-5.60-70°C. By salting out with sodium chloride, a monoazo compound represented by the following formula (%) was obtained in the form of a free acid.

Add 0.3 parts of this monoazo compound to 200 parts of water and add 10 parts of cotton.
1 part and 8 parts of Glauber's salt were added, the temperature was raised to 60°C, 4 parts of soda carbonate was added and dyed at the same temperature for 1 hour, washed with water and soaped to obtain a yellow dyed product with excellent fastness and dyeing performance as described above. Ta.

This compound showed excellent dyeing reproducibility even when the dyeing temperature, bath ratio, and salt concentration were slightly changed.

Example 4 Aniline-2゜5-disulfonic acid, 8-aminoacetanilide-4-sulfonic acid, l used in Example 8
-Aminobenzene-8-β-sulfatoethylsulfone and 1-aminobenzene-4-β-sulfatoethylsulfone are replaced in this order by Column A of the table below (compounds of formula (2))
, Column B (formula ■ compound), C41! (Formula related compounds and l1
Monoazo compounds corresponding to each were obtained in the same manner using Ell (compound of formula (Ell)) and dyed to obtain a dyed product having the color tone shown in Ell. These compounds showed the performance described above.

In the table, Q indicates -5Os CHtCH snow 05Os H.

Claims (8)

[Claims] (1) In the form of a free acid, the following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R_1 is hydrogen, halogeno, C_1_-_4 alkyl, C_1_-_4 alkoxy, ureido, or acylamino , R_2 may be hydrogen or R_1 and R_2 may form a benzene ring, and may have sulfo on the ring. R_3 is hydrogen, C_1_
~_4 alkyl, C_1_~_4 alkoxy or sulfo, R_4 and R_5 are each independently hydrogen or optionally substituted alkyl, B_1 and B_2 are each independently hydrogen, methyl, methoxy, ethyl, ethoxy, chloro, bromo, sulfo. or phenylene optionally substituted with carboxy, or naphthylene optionally substituted with sulfo, Y_1 and Y_2 are each independently -
CH_2CH_2L (L is a group that is eliminated by the action of an alkali) or vinyl, and A represents phenyl having at least one water-soluble group. ] A monoazo compound represented by (2) A is the following general formula ▲ Numerical formula, chemical formula, table, etc. , m+n is 1 or 2. ] The monoazo compound according to claim 1, which is represented by: (3) R_1 is hydrogen, chloro, methyl, methoxy, ureido, acetyl, propionyl, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or amino substituted with benzoyl, and R_2 is hydrogen, or R_1 and R_2 The monoazo compound according to claim 1 or 2, which forms a benzene ring with and has one sulfo group on the ring, and R_3 is hydrogen, methyl, or methoxy. (4) The monoazo compound according to any one of claims 1 to 3, wherein R_4 and R_5 are independently hydrogen, methyl, or ethyl. (5) The monoazo compound according to any one of claims 1 to 4, wherein B_1 and B_2 are phenylene which may be independently substituted with methyl or methoxy. (6) The monoazo compound according to any one of claims 1 to 5, wherein Y_1 and Y_2 are both β-sulfate ethyl. (7) In the form of free acid, there is the following general formula ▲ mathematical formula, chemical formula, table, etc. ▼ [In the formula, R_8 is ureido or acetylamino, and R
_9 is hydrogen or R_8 is methyl and R_9
is methoxy and R_1_0 is hydrogen, methyl or ethyl. ] The monoazo compound according to claim 1, which is represented by: (8) In the form of free acid, the following general formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (I) [In the formula, R_1 is hydrogen, halogeno, C_1_-_4 alkyl, C_1_-_4 alkoxy, ureido, or acylamino , R_3 is hydrogen, or R_1 and R_2 can form a benzene ring, and may have a sulfo group on the same ring, R_3 is hydrogen, C_1_-_4 alkyl,
C_1_-_4 alkoxy or sulfo, R_4 and R_
5 is independently hydrogen or optionally substituted alkyl, B_1 and B_2 are independently hydrogen, phenylene, or sulfo, optionally substituted with methyl, methoxy, ethyl, ethoxy, chloro, bromo, sulfo or carboxy. Naphthylene optionally substituted with Y
_1 and Y_2 are -CH_2CH_2L(
L represents a group that is eliminated by the action of an alkali) or vinyl, and A represents phenyl having at least one water-soluble group. ] A method for dyeing or printing a fiber material, characterized by using a monoazo compound shown in the following.