JPH0372572A - Monoazo compound and dyeing and printing hydrophobic fiber material using it - Google Patents

Abstract

NEW MATERIAL:A monoazo compd. of formula I in the form of a free acid (wherein D is a phenylene or a naphthylene which may have a substituent; R is H or an alkyl which may have a substituent; A is a phenylene or a naphthylene which may have a substituent; V is O, or S; B is an alkyl, a cyclohexyl, an alkenyl, a phenyl) etc.; Z1 and Z2 are each formula II or III, Y is a group which can be eliminated by the action of an alkali). USE:A dye with a reactivity with a fiber and capable of dyeing or printing a material contg. hydroxyl groups or carbonamide groups such as cotton, flax, polyamide fiber, leather, etc., with excellent sunlight-fastness, wetfastness, friction-fastness, alkali resistance, etc. PREPARATION:A monoazo compd. of formula I is obtd. by reacting a compd. of formula IV and a compound of formula V (wherein W is Cl or F) in an aq. medium and reacting the reaction product with a compd. of formula VI.

Description

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

Conventional technology For example, in Japanese Patent Application Laid-open No. 58-204051, the following formula A reactive dye represented by is shown.

Problems to be Solved by the Invention Conventionally, various reactive dyes have been widely used in the fields of dyeing and printing textile materials. However, the current state of the art still does not fully satisfy the high requirements regarding suitability for specific dyeing methods and the increasing sophistication of requirements regarding the fastness of dyed products.

The known red reactive dyes mentioned above are insufficient in terms of solubility, dyeing performance (e.g. build-up properties, etc.) and fastness (e.g. acid hydrolysis fastness, chlorine fastness, etc.), and further improved dyes are needed. Provision is strongly requested.

The importance of having excellent solubility is explained by, for example, Adikshi Sonary of Soybean and Dying.
ionary of dyes and dyeing
).

As is clear from KG Ponting, p. 159 (1980), the first step is to correct the staining problem. Furthermore, in recent years, aqueous liquid compositions of dyes have been in the spotlight for reasons such as energy saving and automatic measurement, and are also an important element from their applicability.

The importance of having excellent build-up properties is an extremely important factor in today's world, where demands for economic efficiency of dyeing methods are becoming higher and higher.

In order to satisfy high requirements regarding the fastness of dyed products, it is necessary to ensure that the structure of the dye molecule itself and the bond between the fiber and the dye are stable under the conditions of use in dyeing, post-processing processes, and various uses of dyed products. This is required.

The present inventors completed the present invention as a result of extensive research aimed at finding a new compound that can improve the drawbacks of the above-mentioned known dyes and further satisfy a wide range of requirements for dyes.

Means for Solving the Problems The present invention provides a free acid having the following formula (1,) [wherein D is optionally substituted phenylene or naphthylene, R is hydrogen or optionally substituted alkyl,
A is optionally substituted phenylene or naphthylene,
■ represents 10 - or -S-, and B represents optionally substituted alkyl, cyclohexyl, alkenyl, optionally substituted phenyl, optionally substituted naphthyl, or optionally substituted benzyl. Representation, Zs and 2! are independently of each other -8OgCH=CHg or -SO
It represents CkhCkhY, and Y represents a group that is eliminated by the action of an alkali. 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 20), the substituted phenylene represented by D is preferably methyl, ethyl, methoxy, ethoxy, halogeno, acetylamino, propionylamino,
Nitro, sulfo, carboxy, vinylsulfonyl and β
- selected from the group consisting of sulfur-1-ethylsulfonyl, 1
゜Phenylene substituted with 2 or 8 substituents. Among them, the case where the number of substituents is 2 or less is preferable, and among them, sulfophenylene is particularly preferable from the viewpoint of dye properties.

The substituted naphthylene represented by D is preferably a naphthylene substituted with one or two substituents selected from the group of sulfo, vinylsulfonyl and β-sulf-1-toethylsulfonyl. Among these, the case where the number of substituents is one is preferable, and among them, sulfonaphthylene is particularly preferable from the viewpoint of dye properties. Among these, the most excellent one is the following formula: [In the formula, the bond indicated by an asterisk means that it is connected to an azo bond. ] It is indicated by.

In the general formula (I), the alkyl group represented by R is preferably an alkyl group having 1 to 4 carbon atoms, and the optionally substituted groups include hydroxy, cyano, alkoxy, halogen, carboxy, Carbamoyl, alkoxycarbonyl, alkylcarbonyloxy, sulfo, and sulfamoyl are preferred.

Preferred examples of R include methyl, ethyl, n-
Propyl, 1so-propyl, n-butyl, 1so-butyl, 5ec-butyl, 2-hydroxyethyl, 2-hydroxypropyl, 8-hydroxypropyl, 2-hydroxybutyl, 8-hydroxybutyl, 4-hydroxybutyl, 2. 8-dihydroxypropyl, 8.4-dihydroxybutyl, cyanomethyl, 2-cyanoethyl, 8
-cyanopropyl, methoxymethyl, ethoxymethyl,
2-methoxyethyl, 2-ethoxyethyl, 8-methoxypropyl, 8-ethoxypropyl, 2-hydroxy-
8-methoxypropyl, chloromethyl, bromomethyl,
2-chloroethyl, 2-bromoethyl, 8-chloropropyl, 8-bromopropyl, 4-chlorobutyl, 4-bromobutyl, carboxymethyl, 2-carboxyethyl, 8-carboxypropyl, 4-carboxybutyl, 1
．． 2-dicarboxyethyl, carbamoylmethyl, 2-
Carbamoylethyl, 8-carbamoylpropyl, 4-
Carbamoylbutyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 8-methoxycarbonylpropyl, 8-ethoxycarbonylpropyl, 4-
Methoxycarbonylbutyl, 4-methoxycarbonylbutyl, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, 2-methylcarbonyloxyethyl,
2-ethylcarbonyloxyethyl, 8-methylcarbonyloxypropyl, 8-ethylcarbonyloxypropyl, 4-methylcarbonyloxybutyl, 4-ethylcarbonyloxybutyl, sulfomethyl, 2-sulfoether, 8-sulfopropyl, 4-sulfobutyl , sulfamoylmethyl, 2-sulfamoylethyl, 8-sulf 1 moylpropyl, 4-sulf 1 moylbutyl, and the like.

Among these, particularly preferable R is hydrogen, methyl or ethyl.

In general formula (I), A is preferably substituted with phenylene or sulfo optionally substituted with 1 or 2 substituents selected from the group of methyl, ethyl, methoxy, ethoxy, chloro, bromo and sulfo. For example, R (in the formula, the bond shown with an asterisk means a bond connected to the -N- group).

Zt and hee Z! bE -8OzCHgCHmYt'
In the case of h ;b (D
H, 0POaHz, 0COC) is, 5SOsH, C4
'etc. list 1. f 6 tL le.

Zl and he Zg,! -L, like t Lz < J! ,
-8OzCHxCH: tOE30sH and -8OsCH
=Ckh.

The optionally substituted alkyl represented by B is, for example, one or two selected from alkoxy, sulfo, carboxy, hydroxy, chloro, phenyl, cyano, and sulfate having 1 to 4 carbon atoms. Preference is given to alkyl having 1 to 4 carbon atoms which may be substituted by substituents.

Among them, methyl, ethyl, n-propyl, 1
so-propyl, n-butyl, 180-butyl, 8eC
-butyl, β-hydroxyethyl, β-sulfatoethyl, μm sulfoethyl, β-methoxyethyl, β-ethoxyethyl, β-chloroethyl, β-carboxyethyl, and the like.

Further, the alkenyl represented by B preferably has 8 or 4 carbon atoms, such as allyl and 8-butenyl.

Furthermore, the optionally substituted phenyl represented by B includes, for example, alkyl having 1 to 4 carbon atoms,
1 or 2 selected from alkoxy, sulfo, carboxy, chloro and pro-sulfone having 1 to 4 carbon atoms;
Individual i! Phenyl which may be substituted with a substituent is preferred.

Particularly preferred among these are phenyl, 2-8-314-chlorophenyl, 2-8= or 4-methylphenyl, and 2-8- or 4-methoxyphenyl.

In addition, the optionally substituted naphthyl represented by B includes, for example, hydroxy, carboxy, sulfo, 1-
1. selected from the group of alkyl having 4 carbon atoms, alkoxy having 1 to 4 carbon atoms and chloro;
Naphthyl optionally substituted with 2 or 8 substituents is preferred.

Among them, particularly preferred are 2-8-4-5-6-7-
or 8-sulfo-1-naphthyl, 1-. 5-. 6-. 7
- or 8-sulfo-2-naphthyl, 5.7- 6.8-
4.8-4, 7-8, 8-4, 6-8
, 7- or 8.6-disulfo-2-naphthyl, 4.6.
82.4.7- or 8.6.8-) lisulfo 1-naphthyl, 1.5.7- 4.6.8- or 8.6.8-)
Examples include disulfo-2-naphthyl.

Furthermore, the optionally substituted benzyl represented by B includes, for example, alkyl having 1 to 4 carbon atoms,
Benzyl optionally substituted by one or two substituents selected from the group of alkoxy, sulfo and chloro having 1 to 4 carbon atoms is preferred.

Particularly preferred among these are benzyl, 2-8- or 4-sulfobenzyl, and the like.

(2) is preferably 10-.

The compounds of the present invention may exist in the form of free acids, but are preferably alkali metal salts or alkaline earth metal salts,
Examples include sodium and potassium salts.

The monoazo compound represented by the general formula (I) of the present invention can be produced, for example, as follows.

In the form of a free acid, it has the following general formula ([) [wherein D and Zl have the above-mentioned meanings]. ], a compound represented by the formula (mV) H-V-B (■) (wherein, ■ and B have the above-mentioned meanings), and cyanuric chloride or cyanuric fluoride, according to a conventional method. A compound represented by the formula (ma) (wherein W represents -C4 or -F, and ■ and B have the above-mentioned meanings) in an aqueous medium at 0 to 60°C, preferably 0 to 60°C. At 80°C, pH 1-7, preferably 1) H
Condensation is carried out while adjusting the concentration to 2 to 6.

Subsequently, the following general formula (■) kl -N-A-Zl (11) [wherein R, A and zl have the above-mentioned meanings. ] in an aqueous medium at 50 to 100°C, preferably 7
0-100°C, pH 2-9, preferably pH 8-7
A monoazo compound of the general formula α) can be obtained by condensing with C while adjusting.

Alternatively, compounds of formula (V) and formula (i) may be mixed in an aqueous medium at 0-60°C, preferably at 0-80°C, at a pH of 1.
After condensation to 1 G, preferably while adjusting the pH to 2 to 7, the compound of formula (ffl) is added to 0 to 1 G in an aqueous medium.
to pig~9 at 00°C, preferably at 80-80°C;
The monoazo compound represented by the general formula α) can also be obtained by condensation while preferably adjusting the pH to 8 to 7.

As a further alternative, H acid or dinic acid and a compound of formula (6) are condensed with a compound of formula ff) in any order, followed by the following general formula (■) Zl-D-NH! (■) (in the formula, Z
l, D have the meanings given above. ) can be coupled with a diazotized product by a conventional method to obtain a monoazo compound represented by general formula (I).

In this method, the condensation order is not particularly limited, but considering the reaction yield and quality of general formula (I), the compound with the lowest reactivity with respect to the compound of formula α) should be started first. Condensation is preferred.

Examples of the compound represented by general formula (1) include phenol, 1-hydroxy-2-8- or -4-methylbenzene, 1-hydroxy-8°4- or -8,6-simethylbenzene, l-hydroxy-2--8- or -4
-ethylbenzene, 1-hydroxy-2--8- or-
4-methoxybenzene, l-hydroxy-2--8- or -4-ethoxybenzene, 1-human o4cy2+, -
a- or -4-chlorobenzene, 8- or 4-hydroxy-phenylmethanesulfonic acid, 8-hydroxybenzenesulfonic acid, 4-hydroxybenzenesulfonic acid, 5
-Hydroxybenzene-1,8-disulfonic acid, 6-hydroxybenzene-1,4-disulfonic acid, 4-hydroxybenzene-1,2-disulfonic acid, 4-hydroxy-5-methylbenzene-1,2-disulfonic acid , 8- or 4-1 do04benzoin, 5-hydroxybenzene-1,8-dicarboxylic acid, 5-hydroxy-2-ethoxybenzenesulfonic acid, 2-hydroxynaphthalene-1
-sulfonic acid, 4-hydroxynaphthalene-1-sulfonic acid, 6-hydroxynaphthalene-1-sulfonic acid, 6
-Hydroxynaphthalene-1-sulfonic acid, 7-hydroxynaphthalene-1-sulfonic acid, 8-hydroxynaphthalene-1-sulfonic acid, 1-hydroxynaphthalene-
2-sulfonic acid, 4-hydroxynaphthalene-2-sulfonic acid, 6-hydroxynaphthalene-2-sulfonic acid,
6-hydroxynaphthalene-2-sulfonic acid, 7-hydroxynaphthalene-2-sulfonic acid, 8-hydroxynaphthalene-2-sulfonic acid, 4-hydroxynaphthalene-1,8-disulfonic acid, 5-hydroxynaphthalene-2-sulfonic acid
1,8-disulfonic acid, 6-hydroxynaphthalene-1
, 8-disulfonic acid, 7-hydroxynaphthalene-1,
8-disulfonic acid, 8-hydroxynaphthalene-1,8
-disulfonic acid, 2-hydroxynaphthalene-1,5-
Disulfonic acid, 8-hydroxynaphthalene-1,6-disulfonic acid, 4-hydroxynaphthalene-1,5-disulfonic acid, 4-hydroxynaphthalene-1,6-disulfonic acid, 8-hydroxynaphthalene-1,6-disulfonic acid , 4-hydroxynaphthalene-1,7-disulfonic acid, 8-hydroxynaphthalene-2,6-disulfonic acid, 4-hydroxynaphthalene-2,6-disulfonic acid,
8-Hydroxynaphthalene-2,7-disulfonic acid, 4
-Hydroxynaphthalene-2,7-disulfonic acid, 6-
hydroxynaphthalene-1,8,5-trisulfonic acid,
7-hydroxynaphthalene-1,8,5-trisulfonic acid, 4-hydroxynaphthalene-1,8,6-trisulfonic acid, 7-aminonaphthalene-1,8゜6-trisulfonic acid, 8-aminonaphthalene- Aromatic compounds such as 1,8゜6-trisulfonic acid and 4-aminonaphthalene-1゜8.7-)disulfonic acid, or methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, 5ec. -Butanol, allyl alcohol, allyl carbinol, 2-chloroethanol, 2-methoxyethanol, 2-ethoxyethanol, 8-methoxypropanol, 8-ethoxypropanol, 2-hydroxyethanesulfonic acid, 8-hydroxy-1-propane Sulfonic acid, 2-cyanoethanol,
2-sulfatoethanol, glycolic acid, 8-hydroxypropionic acid, benzyl alcohol, 2-. 8-
4-chlorobenzyl alcohol, 4-methylbenzyl alcohol, 2-. 8- or 4-sulfobenzyl alcohol, 2-phenylethanol, l-
Mention may be made of aliphatic compounds such as phenyl-2-propanol, and compounds in which droxy is mercapto.

The compound of the present invention has fiber reactivity and can be used for dyeing or printing hydroxy group-containing or carbonamide group-containing materials. Preferably, the material is used in the form of a fibrous material or a blend thereof.

Hydroxy group-containing materials are natural or synthetic hydroxy group-containing materials, such as cellulose fiber materials or their regenerated products and polyvinyl alcohol. Cellulose fiber materials include cotton, as well as other plant materials such as linen,
Hemp, jute and ramie m fibers are preferred. Regenerated cellulose fibers are, for example, viscose stable and filament viscose.

Materials containing carbonamide groups 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-4.

The compounds of the present invention can be dyed or printed on the above-mentioned materials, in particular on the above-mentioned fiber materials, in a manner depending on their physical and chemical properties.

For example, in the case of exhaust dyeing on cellulose fibers, in the presence of an acid binder such as soda carbonate, tribasic sodium phosphate, caustic soda, etc., a neutral salt such as mirabilite or common salt is optionally added.
If desired, solubilizers, penetrants or leveling agents are used in combination and the process is carried out at relatively low temperatures. The neutral salts which accelerate the exhaustion of the dyestuff can be added only after the actual dyeing temperature has been reached, or even before then, optionally in portions.

When dyeing cellulose fibers according to the padding method, it can be padded at room temperature or at an elevated temperature and, after drying, fixed by steaming or dry heat.

When printing is carried out on cellulose fibers, it can be carried out either in one phase, e.g. by printing with a printing paste containing velcro or other acid binders and then steaming at 100-160°C, or in two phases, e.g. It can be printed with a neutral or weakly acidic printing paste, passed through a hot electrolyte-containing alkaline bath, or overpadded with an alkaline electrolyte-containing padding liquid, and subjected to steaming or dry heat treatment.

Thickening agents or emulsifiers, such as, for example, sodium alginate or starch ethers, are used in the printing pastes, if desired in combination with customary printing auxiliaries and/or dispersants, such as, for example, urea.

Suitable acid binders for fixing the compounds of the invention on cellulose fibers are, for example, water-soluble basic salts of alkali metals or alkaline earth metals with inorganic or organic acids or compounds which liberate alkali under heated conditions. Particular mention may be made of alkali metal hydroxides and alkali metal salts of weak to medium strength inorganic or organic acids, of which soda salts and potassium salts are particularly preferred. Examples of such acid binders include caustic soda, caustic potash, heavy d, sodium carbonate, sodium formate, potassium carbonate, secondary or tertiary sodium phosphate, sodium silicate, sodium trichloroacetate, and the like.

The dyeing of synthetic and natural polyamide and polyurethane fibers involves first exhaustion under pH control from an acidic or slightly acidic dye bath and then changing to a neutral or even alkaline pH value for fixation. This can be done by Dyeing can usually be carried out at a temperature of 60 to 120°C, but in order to achieve level dyeing properties, conventional leveling agents such as a condensation product of cyanuric chloride and 8 times the mole of aminobenzenesulfonic acid or aminonaphthalenesulfonic acid or For example, addition products of stearylamine and ethylene oxide can also be used.

The compound of the present invention is characterized in that it exhibits excellent performance in dyeing and printing textile materials. Particularly suitable for dyeing cellulose fiber materials, with excellent sunlight fastness, sweat sunlight fastness and formalin resistance, excellent wet fastness such as washing fastness, peroxide washing fastness, chlorine fastness, chlorine bleach fastness , sweat fastness, acid hydrolysis fastness and alkali resistance, as well as good rub fastness and iron fastness of 11. In addition, it has extremely excellent build-up properties, level dyeing properties, and wash-off properties, as well as good solubility, high exhaustion, and fixation properties, as well as dyeing temperature, alkali agent, and inorganic salt addition amount.
It is characterized by being less susceptible to fluctuations in dye bath ratio and producing dyed products of stable quality.

In addition, the compound of the present invention exhibits excellent build-up properties and excellent alkali stability in cold batch-up dyeing, and shows almost no difference in density or hue between fixation at low temperatures and fixation at 25°C, and also exhibits excellent alkali stability in cold batch-up dyeing. It has the ability to be resistant to hydrolysis by agents.

The present invention will be explained in detail below with reference to practical examples.

In the examples, parts and % mean parts by weight and % by weight, respectively.

Example 1 184.5 parts of cyanuric chloride and 82 parts of methanol were condensed by a conventional method, and 819 parts of 1-acuno-8-naphthol-8,6-disulfonic acid was reacted with this in water under weak acidity. A compound represented by the following formula (%) was obtained in the form of a free acid.

On the other hand, 411 parts of 2-1t nonaphthalene-6-β-sulf-1-toethylsulfone-1-sulfone was diazotized in a conventional manner and coupled with a compound represented by the above formula,
Next, 281.8 parts of l-aminobenzene-8-β-sulfatoethyl sulfone was condensed. The compound thus obtained was salted out with sodium chloride and isolated.
2-aminonaphthalene-6 used in the following formula Example 1 in the free acid form
-β-sulfatoethylsulfone-1-sulfonic acid,
1-amino-a-naphthol-8,6-disulfonic acid,
In place of methanol and l-aminobenzene-8-β-sulf-1-toethylsulfone, in order, the compound of No. 2w in the table below (diazo component), the compound of [881 (coupler)]
, lI compound in column 4 (condensation component) and compound in column 5 (
(reactive group component) in the same manner as in Example 1,
The corresponding monoazo compounds were obtained and dyed to give the following gsm
A dyed product having the color tone shown in was obtained.

(Margin below) (λmaw 555 copies m) A monoazo compound represented by was obtained.

Dyeing Example 1 0.8 parts of the monoazo compound obtained in Example 1 was dissolved in 200 parts of water, 20 parts of Glauber's salt was added, 10 parts of cotton was added, and 5 parts of the monoazo compound obtained in Example 1 were dissolved.
Raise the temperature to 0°C. Then, after 80 minutes had elapsed, 4 parts of soda carbonate was added and dyed at the same temperature for 1 hour. After dyeing, washing with water and soaping were performed to obtain a bluish-red, high-density dyed product with excellent build-up properties, particularly in various fastnesses, especially chlorine fastness, sunlight fastness, and sweat/sunlight fastness.

Dyeing Example 2 0.8 parts of each of the monoazo compounds obtained in Examples 1 and 2 were dissolved in 800 parts of water, 80 parts of Glauber's salt was added, 10 parts of cotton was added, and the temperature was raised to 60°C.

Then, after 20 minutes, add 5 parts of soda carbonate and boil at the same temperature.
Time staining. After dyeing, washing with water and soaping were carried out to obtain a dyed product with a high concentration of red color and excellent build-up properties, particularly in various fastnesses, especially chlorine fastness, sunlight fastness, and sweat/sunlight fastness.

Dyeing example 8 Color paste composition Urea 5 parts Sodium alginate (5%) Base paste 50 parts Heat
1! h 25 parts Baking soda 2 parts Balance 18 parts Color paste with the above composition was printed on mercerized cotton broadcloth, and after intermediate drying, steaming was performed at 100°C for 5 minutes, followed by hot water washing.
Finish by soaping, washing with hot water, and drying.

In this way, a red printed product was obtained which had a high fixation rate, was excellent in various fastnesses, especially chlorine fastness, sunlight fastness and perspiration/sunlight fastness, and had good build-up properties.

Staining Example 4 25 parts of each of the monoazo compounds obtained in Cell Examples 1 and 2 are dissolved in hot water and cooled to 25°C.

To this, 6.6 parts of 82.5% caustic soda aqueous solution and 5
Immediately after adding 150 parts of 0° Baume water glass and further adding water to bring the total volume to t,ooo parts at 25°C, this liquid was used as a padding liquid to roll up a cotton fabric and seal it with a polyethylene film. Store indoors at 20°C.

Cotton fabrics padded in a similar manner and rolled up and sealed with polyethylene film are stored indoors at 5°C. After each padding cloth has been left to stand for 20 hours, the dyeing is finished by washing in cold water, hot water, soaping in boiling detergent, washing in cold water and drying.

When the difference in density and hue between the dyed product left at 20°C for 20 hours and the dyed product left at 5°C for 20 hours was examined, almost no differences were observed.

In addition, a dyed product with good build-up properties was obtained by cold patch-up dyeing.

Dyeing Example 6 25 parts of each of the monoazo compounds obtained in Practical Examples 1 and 2 were dissolved in hot water and cooled to 25°C.

Immediately after adding 82.5% caustic soda aqueous UIO parts and 80 parts of anhydrous sodium sulfate to this and further adding water to bring the total amount to 1.000 parts at 25°C, this liquid was used as a padding liquid and viscose was added. Padding rayon fabric. 4 padded viscose rayon fabrics
1. Seal with polyethylene film and store indoors at 20°C.

In a similar manner, viscose rayon fabrics sealed with a padded rolled polyethylene film are stored indoors at 6°C.

After each padding cloth has been left for 20 hours, the dyeing is washed in cold and then hot water, soaped in boiling detergent,
Finish by washing with cold water and drying.

When we investigated the difference in hue and density between dyed products left at 20°C for 20 hours and dyed products left at 6°C for 20 hours, we found that:
It was hardly recognized.

Dyeing Example 6 Dyeing was carried out in exactly the same manner as in Dyeing Example 2, except that the amount of soda carbonate used was changed from 6 parts to 8 parts, and for each of the monoazo compounds used, the dyed product was equivalent to that obtained in Dyeing Example 8. A dyed product with a quality of .

Dyeing Example 7 Dyeing was carried out in exactly the same manner as in Dyeing Example 2 except that the temperature was changed from 60°C to 50°C, and the dyeing had the same quality as the dyed product obtained in Dyeing Example 2 for each of the monoazo compounds used. I got something. The same thing happened when the temperature was set to 70°C.

Dyeing Example 8 Dyeing was carried out in exactly the same manner as in Dyeing Example 2, except that the amount of Glauber's salt used was changed from 80 parts to 15 parts, and for each of the monoazo compounds used, the same dyed product as that obtained in Dyeing Example 8 was obtained. A quality dyed product was obtained.

(Margin below)

Claims (1)

[Claims] 1) In the form of a free acid, the following formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, D is optionally substituted phenylene or naphthylene, R is hydrogen or optionally substituted alkyl,
A is optionally substituted phenylene or naphthylene,
V represents -O- or -S-, and B represents optionally substituted alkyl, cyclohexyl, alkenyl, optionally substituted phenyl, optionally substituted naphthyl, or optionally substituted benzyl. The expressions Z_1 and Z_2 are independently of each other −SO_2CH=CH_2 or −
SO_2CH_2CH_2Y is represented, and Y represents a group that is eliminated by the action of an alkali. ] A monoazo compound represented by 2) A claim where D is in the form of a free acid and is represented by the following formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, * means that it leads to an azo bond.) 1. The monoazo compound described in 1. 3) The monoazo compound according to claim 1 or 2, wherein Z_1 and Z_2 are independently vinylsulfonyl or β-sulfatoethylsulfonyl. 4) The monoazo compound according to any one of claims 1 to 3, wherein R is hydrogen, methyl or ethyl. 5) A claim in which A is phenylene optionally substituted with one or two groups selected from the group of methyl, ethyl, methoxy, ethoxy, sulfo, carboxy and halogen, or naphthylene optionally substituted with sulfo. 5. The monoazo compound according to any one of 1 to 4. 6) The monoazo compound according to any one of claims 1 to 5, wherein V is -O-. 7) The monoazo compound according to any one of claims 1 to 6, wherein B is alkyl which may have a substituent. 8) Claim 1 wherein B is C_3 or C_4 alkenyl.
7. The monoazo compound according to any one of . 9) Any one of claims 1 to 6, wherein B is phenyl optionally substituted with one or two groups selected from the group consisting of C_1_-_4 alkyl, C_1_-_4 alkoxy, sulfo, carboxy, chloro, and bromo. The monoazo compound described in . 10) A method for dyeing or printing fiber materials, characterized by using the monoazo compound according to any one of claims 1 to 9.