KR100346148B1 - The reactivated yellow disazo-compound - Google Patents

Abstract

The present invention relates to a reactive yellow disazo compound, which improves the time-dependent change and the lowering of the flame retardancy caused by easily decomposed in an alkaline salt bath during printing or continuous dyeing of cellulose fibers or rayon fibers, and also continuous dyeing in a blend. It is an object of the present invention to provide a reactive yellow disazo compound having a significantly improved degree of nylon contamination, and the present invention is characterized by the following formula (5) in the form of a free acid. It can be achieved by providing a reactive yellow disazo compound of.

<Formula 5>

In Formula 5, R ₁ and R ₂ each represent a hydrogen, methyl or methoxy group, X represents a substituent which is free by alkali, and A is a benzene-based or chemical formula represented by the following Formula 6 as a functional group having an aromatic ring. It is a naphthalene type compound represented by 7.

<Formula 6>

N is an integer of 0-3, R <_3> represents hydrogen, a methyl group, or a carboxy group.

<Formula 7>

M and n are integers of 0-3, R <_4> represents hydrogen, a methyl group, or a carboxy group.

Description

Reactive yellow disazo-compound

The present invention relates to a reactive yellow disazo compound, and more particularly, to improve the time-varying phenomenon and the lowering of the flame retardancy caused by easily decomposed in an alkaline salt bath during printing or continuous salts of conventional cellulose fibers or rayon fibers, The present invention also relates to a reactive yellow disazo compound with much improved nylon contamination during continuous dyeing in blends.

As reactive yellow dyes used in printing or continuous salts such as conventional cellulose fibers or rayon fibers, dyes having a vinyl sulfone ester group and a monochlorotriazine type are known.

As the reactive yellow dye having the vinyl sulfone ester group generally used, compounds represented by the following general formula (1) are known.

However, the reactive yellow dye having a vinyl sulfone ester group represented by the formula (1) has a disadvantage in that it is easily decomposed in alkaline salt solution while being excellent in the ignition state and poor in stability over time.

In addition, Japanese Patent Publication No. 39-2634 discloses a yellow monoazo dye having a monochlorotriazine group represented by the following formula (2).

In Formula 2, R ₁ is an alkyl group having 1 or more carbon atoms, and R ₂ represents an alkyl group or a phenyl group having a substituent.

However, the monochlorotriazine type yellow monoazo dye represented by Chemical Formula 2 generally has a disadvantage that the color changes to yellow, which is slightly red when the steaming time is long.

In order to improve the above problems, Japanese Patent Publication No. 59-8763 discloses a reactive monoazo dye represented by the following formula (3).

However, the monochlorotriazine type reactive yellow dye represented by Chemical Formula 3 has a disadvantage in that it is stable to changes over time, but has a low ignition state and becomes a nylon contamination.

Reactive azo dyes having a bifunctional group are known to improve the disadvantages of the reactive dye having the conventional vinyl sulfone ester group or monochlorotriazine group.

In particular, Japanese Patent Publication No. 60-215065 discloses a monoazo dye having a bifunctional group represented by the following general formula (4).

Where A is or In this case, R ₃ and R ₄ each represent hydrogen, methyl group and methoxy group, and R ₅ and R ₆ each represent hydrogen, methyl group, ethyl group, methoxy group, ethoxy group, acetylamine group or ureide group.

However, the dye having a bifunctional group of the type shown in the formula (4) is relatively stable and changes in color as the steaming time is longer and more stable in water fastness, while the dyeing state is higher than the dye having a vinyl sulfone ester group Falling and being polluted by nylon appear to be a disadvantage.

Accordingly, the present invention is to solve the above-mentioned problems of the prior art, and to improve the time-dependent change phenomenon and the lowering of the flame retardancy caused by easy decomposition in the alkaline salt bath during printing or continuous dyeing, such as cellulose fibers or rayon fibers, It is also an object of the present invention to provide a reactive yellow disazo compound with a significantly improved degree of nylon contamination caused by continuous dyeing in a blend.

In order to achieve the above object, the present invention can be achieved by providing a novel reactive yellow disazo compound represented by the following formula (5) in the form of a free acid.

In Formula 5, R ₁ and R ₂ each represent a hydrogen, methyl or methoxy group, X represents a substituent which is free by alkali, and A is a benzene-based or chemical formula represented by the following Formula 6 as a functional group having an aromatic ring. It is a naphthalene type compound represented by 7.

N is an integer of 0-3, R <_3> represents hydrogen, a methyl group, or a carboxy group.

M and n are integers of 0-3, R <_4> represents hydrogen, a methyl group, or a carboxy group.

Particularly preferred among the compounds of Formula 5 are compounds having the structure of Formula 8, wherein A is a benzene compound of Formula 6 and n is 1 and R ₃ is hydrogen.

In Formula 8, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali.

Among the compounds having the structure of Formula 8, R ₁ and R ₂ are each a methyl group, and x is -OSO ₃ H. The compound represented by the following Formula 9 is particularly preferable.

In the compound of Formula 5, a compound having the structure of Formula 10 wherein A is a benzene compound of Formula 6 and n is 1 and R ₃ is a methyl group is preferable.

In Formula 10, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali.

Among the compounds having the structure of Formula 10, R ₁ and R ₂ are each a methoxy group, and x is -OSO ₃ H. The compound represented by the following Formula 11 is more preferable.

In the compound of Formula 5, a compound having the structure of Formula 12 wherein A is a benzene compound of Formula 6 and n is 0 and R ₃ is a carboxy group is preferable.

In Formula 12, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali.

Among the compounds having the structure of Formula 12, R ₁ and R ₂ are each a methyl group, and x is -OSO ₃ H. The compound represented by the following Formula 13 is particularly preferable.

In the compound of Formula 5, A is a naphthalene compound of Formula 7, and m and n are each 1, and R ₄ is hydrogen.

In Formula 14, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali.

Among the compounds having the structure of Formula 14, R ₁ and R ₂ are each a methyl group, and x is -OSO ₃ H. The compound represented by the following Formula 15 is more preferable.

In the compound of Formula 5, A is a naphthalene compound of Formula 7, and m is 0, n is 1, and R ₄ is hydrogen.

In Formula 16, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali.

Among the compounds having the structure of Formula 16, R ₁ and R ₂ are each a methyl group, and x is -OSO ₃ H. The compound represented by the following Formula 17 is particularly preferable.

In the compound of Formula 5, A is a naphthalene compound of Formula 7, wherein m is 1, n is 0, and R ₄ is hydrogen.

In Formula 18, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali.

Among the compounds having the structure of Formula 18, R ₁ and R ₂ are each a methyl group, x is -OSO ₃ H, and the following Formula 19 and R ₁ , R ₂ are each hydrogen, x is -OSO ₃ H, The compound represented by is more preferable.

In the compound of Formula 5, A is a naphthalene compound of Formula 7, and m is 2, n is 1, and R ₄ is hydrogen.

In Formula 21, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali.

Among the compounds having the structure of Formula 21, R ₁ and R ₂ are each hydrogen, and x is -OSO ₃ H. The compound represented by the following Formula 22 is particularly preferable.

In addition, the present invention by the coupling reaction of the compound having the structure of the formula (23) below the benzene-based compound or naphthalene-based compound of the azo component in a neutral condition in order to more effectively prepare the compound defined by the formula (5) After obtaining the compound of Formula 25, the compound of Formula 24 or Formula 25 can be easily prepared by a coupling reaction under neutral conditions with a compound having the structure of Formula 26 having a reactor capable of liberation by alkali.

In Formula 24, n is an integer of 0 to 3, R ₃ represents hydrogen, a methyl group or a carboxy group

In Formula 25, m and n are integers of 0 to 3, and R ₄ represents hydrogen, a methyl group, or a carboxy group.

In Formula 26, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali.

Benzene-based compounds which can be used in preparing the compound defined by Chemical Formula 5 of the present invention include paratoluidine-2-sulfonic acid, aniline-4-sulfonic acid, 2-aminobenzoic acid, and the like. Amine-1,5-disulfonic acid, 1-naphthylamine-4-sulfonic acid, 1-naphthylamine-7-sulfonic acid, 2-naphthylamine-3,6,8-trisulfonic acid and the like.

In addition, azo components having a reactor capable of being liberated by alkali include 1-aminobenzene-4-β-sulfatoethylsulfonic acid and 2,5-dimethyl-1-aminobenzene-4-β-sulfatoethylsulfur. Phonic acid, 2,5-dimethoxy-1-aminobenzene-4-β-sulfatoethyl-sulfonic acid, 2-methyl-5-methoxy-1-aminobenzene-4-β-sulfatoethylsulfonic acid Etc.

As described above, the compound is not degradable or discolorable of dyes having general vinyl sulfone ester groups in printing or continuous dyeing to cellulose or rayon fibers, is stable to changes over time, and exhibits excellent flame retardancy, as well as nylon. There is little contamination in the mixture and it has the advantage of being suitable for dyeing blends.

Hereinafter, the reactive yellow disazo dye of the present invention will be described in more detail with reference to the following examples. However, the present invention is not limited to the following examples, and the following examples are merely described as examples of the present invention. Put it.

<Example 1>

173 g of aniline-4-sulfonic acid was dispersed in 500 g of water, cooled to 5 ° C. or less, 90 g of hydrochloric acid was added thereto, stirred for 1 hour, the stirred solution was cooled to 5 ° C., and 70 g of acetic acid was added to the solution. The solution dissolved completely in 200 g of water was added dropwise, and when the dropwise addition was completed, the mixture was kept stirred for 1.5 hours and excess acetic acid was removed to prepare a diazo solution.

Separately, 188 g of metaphenylenediamine-2-sulfonic acid was dispersed in 700 g of water, 60 g of soda ash was completely dissolved, and then cooled to 10 ° C., and the diazo solution prepared above was added dropwise to the solution. To the reaction solution was prepared by adding a solution in which 62 g of soda ash was completely dissolved in 350 g of water.

Apart from the above, 309 g of 2,5-dimethoxy-1-aminobenzene-4-β-sulfatoethylsulfonic acid was dispersed in 400 g of water, and 140 g of hydrochloric acid was added thereto, followed by cooling to 5 DEG C or lower. A solution obtained by adding 71 g of acetic acid to 200 g of water was added dropwise for 1 hour, and then the solution was added to the reaction solution prepared above, and 70 g of soda ash was added thereto to terminate the reaction. 330 g of disazo dye were obtained, and the UVλ max value and the observed physical properties of the prepared yellow disazo dye are shown in Table 1.

The yellow disazo dyes prepared above were used to measure the degree of outbreak, flame retardancy and nylon contamination by the following method, and visually observe the color change after 4 hours and 8 hours while performing continuous dyeing. 1 is shown.

-Nylon Pollution Degree-

100 g of urea, 10 g of sodium metanitrobenzenesulfonic acid, 20 g of sodium bicarbonate and 55 g of sodium alginate are mixed, printed on a rayon using a 100 mesh print screen, and then dried and steamed to fix the printed dye. After treatment for 10 minutes at 102 to 105 ℃, and the fixed dyes were washed three times or more alternately using cold water and hot water, and then prepared by soap and dried to measure the nylon contamination by the following method.

◎: Very good

○: Good

△: normal

×: bad

-Outbreak-

Dispersion of sodium alginate was added to 3% to 6% by volume (v / v) of water, and a small amount of longalite was added to prepare a mixture. The mixture was prepared in the dyeing solution through the printing process. After applying and drying at 100 ± 2 ℃ for 3 minutes, steamed at 100 ℃ to 105 ℃ for 10 minutes, washed with water and dried, and then showed a germination state by the following method.

◎: Very good

○: Good

△: normal

×: bad

-Flame Retardant-

Sodium alginate was dispersed in an amount of 3 to 6% by volume (v / v) with respect to water, and a small amount of Longalite was added to prepare a mixture. The salts were dyed using the printing method, dried at 100 ± 2 ° C. for 3 minutes, steamed at 100 ° C. to 105 ° C. for 10 minutes, washed with water and dried, and then exhibited a germination state by the following method.

◎: Very good

○: Good

△: normal

×: bad

-Continuous dyeing-

3 g of the dye composition, 0.4 g of sodium alginate, and 46.6 g of water were mixed and dissolved, and then continuous dyeing was tested by adding an appropriate amount of sodium hydroxide (32.5% aqueous solution) as an alkali to the solution. At this time, the temperature of the padding liquid is about 30 ℃, the bath ratio is 70%, dried the padded fibers for 5 minutes in a dryer at 60 ℃, saturated with steam for 40 seconds at 102 to 105 ℃ steam oven alternately cold water and hot water After washing three times or more with soaping and dried.

<Example 2>

187 g of paratoluidine-2-sulfonic acid and 220 g of hydrochloric acid were added to 500 g of water, cooled to 10 ° C. and stirred for 1 hour. The stirred solution was cooled to 5 ° C., and 70 g of acetic acid was added to 200 g of water. To the diazo solution was prepared by dropping the solution completely dissolved in the solution, and after the dropwise addition, the solution was stirred for 3 hours and excess acetic acid was removed.

Separately, 188 g of metaphenylenediamine-2-sulfonic acid was dispersed in 700 g of water, and 62 g of soda ash was completely dissolved, followed by cooling to 10 ° C., and the diazo solution prepared above was added dropwise to the solution. 55 g of soda ash was completely dissolved in 600 g of water, to which a reaction solution was prepared.

Apart from the above, 341 g of 2,5-dimethoxy-1-aminobenzene-4-β-sulfatoethylsulfonic acid was dispersed in 400 g of water, and 190 g of hydrochloric acid was added thereto, followed by cooling to 5 DEG C or lower. A solution obtained by adding 72 g of acetic acid to 200 g of water was added dropwise for 1 hour, and then the solution was added to the reaction solution prepared above, and 210 g of soda ash was added thereto to terminate the reaction. 3400 g of disazo dye were obtained, and the UVλ max value and the observed physical properties of the prepared yellow disazo dye are shown in Table 1.

The yellow disazo dyes prepared above were measured in the same manner as in Example 1, and the color change during the dyeing, flame retardant, nylon contamination, and continuous dyeing was shown in Table 1.

<Example 3>

137 g of 1-aminobenzoic acid was dispersed in 200 g of water, cooled to 5 ° C. or lower, 120 g of hydrochloric acid was added thereto, stirred for 2 hours, and 70 g of acetic acid completely dissolved in 200 g of water was added dropwise thereto. And, when the addition was completed, the stirring was maintained for 1.5 hours and excess acetic acid was removed to prepare a diazo solution.

Separately, 188 g of metaphenylenediamine-2-sulfonic acid was dispersed in 700 g of water, 60 g of soda ash was completely dissolved, and then cooled to 10 ° C., and the diazo solution prepared above was added dropwise to the solution. To the reaction solution was prepared by adding a solution of 80 g of soda ash completely dissolved in 450 g of water.

Apart from the above, 309 g of 2,5-dimethoxy-1-aminobenzene-4-β-sulfatoethylsulfonic acid was dispersed in 400 g of water, and 140 g of hydrochloric acid was added thereto, followed by cooling to 5 DEG C or lower. A solution obtained by adding 71 g of acetic acid to 200 g of water was added dropwise for 1 hour, and then the solution was added to the reaction solution prepared above, and 75 g of soda ash was added thereto to terminate the reaction. 3100 g of disazo dye was obtained, and the UVλ max value and the observed physical properties of the prepared yellow disazo dye are shown in Table 1.

The yellow disazo dyes prepared above were measured in the same manner as in Example 1, and the color change during the dyeing, flame retardant, nylon contamination, and continuous dyeing was shown in Table 1 below.

<Example 4>

303 g of 2-naphthylamine-1,5-disulfonic acid was dispersed in 1000 g of water, cooled to 10 ° C. or less, 152 g of hydrochloric acid was added and stirred for 1.5 hours. The stirred solution was cooled to 5 ° C., and then A solution in which 71 g of acetic acid was completely dissolved in 200 g of water was added dropwise, and after the dropwise addition, the solution was stirred for 2 hours to remove excess acetic acid to prepare a diazo solution.

Separately, 188 g of metaphenylenediamine-2-sulfonic acid was dispersed in 700 g of water, and 60 g of soda ash was added thereto to completely dissolve. The reaction solution was prepared by adding the diazo solution prepared above.

Apart from the above, 309 g of 2,5-dimethoxy-1-aminobenzene-4-β-sulfatoethylsulfonic acid was dispersed in 400 g of water, and 140 g of hydrochloric acid was added thereto, followed by cooling to 5 DEG C or lower. A solution obtained by adding 71 g of acetic acid to 200 g of water was added dropwise for 1 hour, and then the solution was added to the reaction solution prepared above, and 170 g of soda ash was added thereto to terminate the reaction. 3980 g of disazo dye were obtained, and the UVλ max value and the observed physical properties of the prepared yellow disazo dye are shown in Table 1.

The yellow disazo dyes prepared above were measured in the same manner as in Example 1, and the color change during the dyeing, flame retardant, nylon contamination, and continuous dyeing was shown in Table 1.

Example 5

223 g of 1-naphthylamine-4-sulfonic acid was dispersed in 500 g of water, cooled to 10 ° C. or lower, 102 g of hydrochloric acid was added thereto, stirred for 3 hours, the stirred solution was cooled to 5 ° C., and then 71 g of this solution was added thereto. A solution of completely dissolved acetic acid in 200 g of water was added dropwise, and after the dropwise addition, the solution was stirred for 3 hours to remove excess acetic acid to prepare a diazo solution.

Separately, 188 g of metaphenylenediamine-2-sulfonic acid was dispersed in 700 g of water, 60 g of soda ash was completely dissolved, and then cooled to 10 ° C., and the diazo solution prepared above was added dropwise to the solution. To the reaction solution was prepared by adding a solution of 50 g of soda ash completely dissolved in 300 g of water.

Apart from the above, 309 g of 2,5-dimethoxy-1-aminobenzene-4-β-sulfatoethylsulfonic acid was dispersed in 400 g of water, and 140 g of hydrochloric acid was added thereto, cooled to 5 DEG C, and 71 g of the dispersion. Was added dropwise to the reaction solution prepared in the above for 1 hour, and the solution was added to the reaction solution prepared above, and 155 g of soda ash was added thereto to terminate the reaction. 3400 g of azo dye was obtained, and the UVλ max value and the observed physical properties of the prepared yellow disazo dye are shown in Table 1.

The yellow disazo dyes prepared above were measured in the same manner as in Example 1, and the color change during the dyeing, flame retardant, nylon contamination, and continuous dyeing was shown in Table 1.

<Example 6>

Disperse 223 g of 1-naphthylamine-7-sulfonic acid in 3000 g of water, warm to 50 ° C, add 70 g of 25% caustic soda and 9 g of soda ash, completely dissolve, and cool again to 5 ° C to give 250 g of hydrochloric acid. The mixture was stirred for 3 hours, and a solution in which 71 g of acetic acid was completely dissolved in 200 g of water was added dropwise to the stirring solution. After the dropwise addition, the solution was stirred for 2 hours to remove excess acetic acid, thereby preparing a diazo solution.

Separately, 188 g of metaphenylenediamine-2-sulfonic acid was dispersed in 700 g of water, 60 g of soda ash was completely dissolved, and then cooled to 10 ° C., and the diazo solution prepared above was added dropwise to the solution. To the reaction solution was prepared by adding a solution in which 70 g of soda ash was completely dissolved in 300 g of water.

Apart from the above, 325 g of 2-methyl-5-methoxy-1-aminobenzene-4-β-sulfatoethylsulfonic acid was dispersed in 400 g of water, and 130 g of hydrochloric acid was added to cool the solution to 5 ° C. To 71 g of acetic acid in 200 g of water was added dropwise for 1 hour, and this solution was added to the reaction solution prepared above, and 160 g of soda ash was added thereto to terminate the reaction, which is defined by Chemical Formula 19. 3500 g of a yellow disazo dye was obtained, and the UVλ max value and the observed physical properties of the prepared yellow disazo dye were shown in Table 1.

The yellow disazo dyes prepared above were measured in the same manner as in Example 1, and the color change during the dyeing, flame retardant, nylon contamination, and continuous dyeing was shown in Table 1.

<Example 7>

223 g of 1-naphthylamine-6-sulfonic acid was dispersed in 350 g of water, and the temperature was raised to 50 ° C. Then, 70 g of 25% caustic soda and 9 g of soda ash were added for complete dissolution. Then, the mixture was cooled to 5 ° C and 250 g of hydrochloric acid. To the mixture was stirred for 3 hours, and a solution in which 71 g of acetic acid was completely dissolved in 200 g of water was added dropwise to the stirring solution. After the dropwise addition, the solution was stirred for 2 hours to remove excess acetic acid, thereby preparing a diazo solution.

Separately, 188 g of metaphenylenediamine-2-sulfonic acid was dispersed in 700 g of water, 60 g of soda ash was completely dissolved, and then cooled to 10 ° C., and the diazo solution prepared above was added dropwise to the solution. To the reaction solution was prepared by adding a solution in which 70 g of soda ash was completely dissolved in 300 g of water.

Apart from the above, 281 g of 1 aminobenzene-4-β-sulfatoethylsulfonic acid was dispersed in 200 g of water, and 120 g of hydrochloric acid was added to cool the mixture to 5 ° C or lower, and 70 g of acetic acid was added to 200 g of water. The solution obtained in the above was added dropwise for 1 hour, and then the solution was added to the reaction solution prepared above, and 80 g of soda ash was added thereto to terminate the reaction, thereby obtaining 3310 g of yellow disazo dye defined by Chemical Formula 20. Table 1 shows the UVλ max values and the observed physical properties of the prepared yellow disazo dyes.

The yellow disazo dyes prepared above were measured in the same manner as in Example 1, and the color change during the dyeing, flame retardant, nylon contamination, and continuous dyeing was shown in Table 1.

<Example 8>

383 g of 2-taphthylamine-3,6,8-trisulfonic acid was dispersed in 700 g of water, and after 0.5 hour, 70 g of acetic acid was added and cooled to 5 ° C or less, followed by 100 g of hydrochloric acid, followed by stirring for 3 hours. The diazo solution was prepared by holding and removing excess acetic acid.

Separately, 188 g of metaphenylenediamine-2-sulfonic acid was dispersed in 700 g of water, 60 g of soda ash was completely dissolved, and then cooled to 10 ° C., and the diazo solution prepared above was added dropwise to the solution. 55 g of soda ash was completely dissolved in 300 g of water, to thereby prepare a reaction solution.

Apart from the above, 281 g of 1-aminobenzene-4-β-sulfatoethylsulfonic acid was dispersed in 200 g of water, 120 g of hydrochloric acid was added and cooled to 5 DEG C, and 70 g of acetic acid was added to 200 g of water. To this solution was added dropwise for 1 hour, and the solution was added to the reaction solution prepared above, and 50 g of soda ash was added thereto to terminate the reaction, thereby obtaining 4080 g of yellow disazo dye defined by Chemical Formula 22. Table 1 shows the UVλ max values and the observed physical properties of the prepared yellow disazo dyes.

The yellow disazo dyes prepared above were measured in the same manner as in Example 1, and the color change during the dyeing, flame retardant, nylon contamination, and continuous dyeing was shown in Table 1.

Comparative Example 1

In the same manner as in Example 1 using a yellow disazo dye defined by the conventional formula (1), the degree of outbreak, flame retardant and nylon contamination was measured, and the color change during continuous dyeing was also shown in Table 1.

Comparative Example 2

In the same manner as in Example 1 using a yellow disazo dye defined by the conventional formula (3), the degree of fouling, flame retardant and nylon contamination was measured, and the color change during continuous dyeing was also shown in Table 1.

division Properties λmax Color change Outbreak Flameproof Nylon pollution color Constellation 4 hours later 12 hours later Example 1 yellow Liquid 427 nm No discoloration No discoloration ◎ ◎ ○ Example 2 yellow Liquid 420nm No discoloration No discoloration ◎ ○ ◎ Example 3 yellow Liquid 430 nm No discoloration No discoloration ◎ ◎ ◎ Example 4 yellow Liquid 428nm No discoloration No discoloration ○ ◎ ○ Example 5 yellow Liquid 434 nm No discoloration No discoloration ◎ ○ ○ Example 6 yellow Liquid 427 nm No discoloration No discoloration ◎ ◎ ◎ Example 7 yellow Liquid 431 nm No discoloration No discoloration ◎ ◎ ◎ Example 8 yellow Liquid 425 nm No discoloration No discoloration ◎ ◎ ○ Comparative Example 1 yellow Liquid - No discoloration Discolored ○ ○ ○ Comparative Example 2 yellow Liquid - No discoloration No discoloration × × ×

As shown in Table 1, as a result of testing the stability of the aging with continuous dyeing using the compounds of Examples 1 to 8 according to the present invention, it can be confirmed that it does not discolor after 4 hours or after 12 hours. And it is confirmed that the flame retardant state is excellent and does not become a nylon contamination.

However, Comparative Example 1 using the conventional yellow dye represented by the formula (1) has the advantage of excellent flame and flame-retardant state, and does not become a nylon contamination, but it is easily decomposed in alkaline salt solution during continuous dyeing, the stability of the time stability is in Table 1 You can check it through

In addition, in the case of Comparative Example 2 using the conventional yellow dye represented by the formula (3) it can be confirmed that the discoloration does not change due to excellent cyanosis stability during continuous dyeing, but the outbreak of the flame and flame retardant, nylon contamination through Table 1 You can check it.

As described above, the present invention improves the time-varying phenomenon and the lowering of the flame retardancy caused by easily decomposed in an alkaline salt bath when printing or continuous salts such as cellulose fiber or rayon fiber, and also occurs when continuous dyeing in blends. It is a useful invention to provide reactive yellow disazo compounds with significantly improved contamination.

Claims (20)

A novel reactive yellow disazo compound represented by the following formula (5) in the form of a free acid. <Formula 5> In Formula 5, R ₁ and R ₂ each represent a hydrogen, methyl or methoxy group, X represents a substituent which is free by alkali, and A is a benzene-based or chemical formula represented by the following Formula 6 as a functional group having an aromatic ring. It is a naphthalene type compound represented by 7. <Formula 6> N is an integer of 0-3, R <_3> represents hydrogen, a methyl group, or a carboxy group. <Formula 7> M and n are integers of 0-3, R <_4> represents hydrogen, a methyl group, or a carboxy group. The reactive yellow disazo compound according to claim 1, wherein A is a benzene compound of Formula 6, wherein n is 1 and R ₃ is hydrogen. <Formula 8> In Formula 8, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali. The reactive yellow disazo compound according to claim 2, wherein R ₁ and R ₂ are each a methyl group, and x is -OSO ₃ H. <Formula 9> The reactive yellow disazo compound according to claim 1, wherein A is a benzene compound of Formula 6, wherein n is 1 and R ₃ is a methyl group. <Formula 10> In Formula 10, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali. The reactive yellow disazo compound according to claim 4, wherein R ₁ and R ₂ are each a methoxy group and x is -OSO ₃ H. <Formula 11> The reactive yellow disazo compound according to claim 1, wherein A is a benzene compound of Formula 6, wherein n is 0 and R ₃ is a carboxyl group. <Formula 12> In Formula 12, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali. 7. The reactive yellow disazo compound according to claim 6, wherein R ₁ and R ₂ are each a methyl group, and x is -OSO ₃ H. (13) The reactive yellow disazo compound according to claim 1, wherein A is a naphthalene compound of Formula 7, wherein m and n are each 1 and R ₄ is hydrogen. <Formula 14> In Formula 14, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali. 9. The reactive yellow disazo compound according to claim 8, wherein R ₁ and R ₂ are each a methyl group, and x is -OSO ₃ H. <Formula 15> The reactive yellow disazo compound according to claim 1, wherein A is a naphthalene compound of formula 7, wherein m is 0, n is 1, and R ₄ is hydrogen. <Formula 16> In Formula 16, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali. The reactive yellow disazo compound according to claim 10, wherein R ₁ and R ₂ are each a methyl group, and x is -OSO ₃ H. <Formula 17> The reactive yellow disazo compound according to claim 1, wherein A is a naphthalene compound of Formula 7 wherein m is 1, n is 0 and R ₄ is hydrogen. <Formula 18> In Formula 18, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali. 13. The reactive yellow disazo compound according to claim 12, wherein R ₁ and R ₂ are each a methyl group and x is -OSO ₃ H. <Formula 19> 13. The reactive yellow disazo compound according to claim 12, wherein R ₁ and R ₂ are each hydrogen and x is -OSO ₃ H. <Formula 20> The reactive yellow disazo compound according to claim 1, wherein A is a naphthalene compound of Formula 7 wherein m is 2, n is 1 and R ₄ is hydrogen. <Formula 21> In Formula 21, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali. 16. The reactive yellow disazo compound according to claim 15, wherein R ₁ and R ₂ are each hydrogen and x is -OSO ₃ H. <Formula 22> To prepare a reactive yellow disazo compound defined by Chemical Formula 5, a benzene-based compound or a naphthalene-based compound, which is an azo component, is subjected to a coupling reaction with a compound having the structure of Chemical Formula 23 under neutral conditions. Reactive yellow disazo compound, characterized in that the compound of formula (24) or (25) is subjected to a coupling reaction under neutral conditions with a compound having the structure of formula (26) having a reactor capable of being liberated by alkali after Manufacturing method. <Formula 5> In Formula 5, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, X represents a substituent which is free by alkali, and A is a benzene group represented by Formula 6 or a naphthalene system represented by Formula 7 Compound. <Formula 6> N is an integer of 0-3, R <_3> represents hydrogen, a methyl group, or a carboxy group. <Formula 7> M and n are integers of 0-3, R <_4> represents hydrogen, a methyl group, or a carboxy group. <Formula 23> <Formula 24> In Formula 24, n is an integer of 0 to 3, R ₃ represents hydrogen, a methyl group or a carboxy group <Formula 25> In Formula 25, m and n represent an integer of 0 to 3, and R ₄ represents hydrogen, a methyl group, or a carboxy group. <Formula 26> In Formula 26, R ₁ and R ₂ are each hydrogen, methyl or methoxy group, and X represents a substituent which is free by alkali. 18. The method for producing a reactive yellow disazo compound according to claim 17, wherein paratoluidine-2-sulfonic acid, aniline-4-sulfonic acid, 2-aminobenzoic acid, or the like is used as the benzene compound. 18. The method according to claim 17, wherein the naphthalene compound is 2-naphthylamine-1,5-disulfonic acid, 1-naphthylamine-4-sulfonic acid, 1-naphthylamine-7-sulfonic acid, 2-naphthylamine A process for producing a reactive yellow disazo compound characterized by using -3,6,8-trisulfonic acid. 18. Azo component according to claim 17, wherein the azo component has a reactor that is freed by alkali, 1-aminobenzene-4-β-sulfatoethylsulfonic acid, 2,5-dimethyl-1-aminobenzene-4-β-sulfur. Peytoethylsulfonic acid, 2,5-dimethoxy-1-aminobenzene-4-β-sulfatoethyl-sulfonic acid, 2-methyl-5-methoxy-1-aminobenzene-4-β-sulfate A method for producing a reactive yellow disazo compound characterized by using toethylsulfonic acid and the like.