KR100368990B1 - Antibacterial red dye - Google Patents

Abstract

The present invention relates to a red antibacterial dye represented by the following general formula (I).

(I)

In the formula, A is hydrogen, methyl group, vinyl sulfone group, methoxy group, n, m is an integer of 1-3.

Cotton fabrics dyed using the dyes of the present invention have the effect of exhibiting strong antimicrobial properties.

Description

Antibacterial red dye

The present invention relates to an antibacterial red dye represented by the following general formula (I).

(I)

In the formula, A is hydrogen, methyl group, vinyl sulfone group, methoxy group, n, m is an integer of 1-3.

The compound of general formula (I) contains a silver sulfadiazine group, which is a strong antimicrobial reactor, and shows a strong antimicrobial effect.

Substances that inhibit or sterilize pathogenic bacteria, such as penicillin, sulfonamides, and isonicotine, are called antimicrobial agents.

Recently, since it is known that silver has antitumor effect along with platinum, the dye industry has steadily attempted to introduce silver compounds into dye molecules in preparing antimicrobial dyes.

Conventional antimicrobial dyeing methods using silver include dyeing by adding silver powder to dyes, electrophoretic fractionation, and the use of an extremely diluted solution of silver nitrate (AgNO ₃ ). . The method of adding silver powder to a dye is limited in color selection such that it is limited to only a partial color such as brown, and there is a problem that the dyeing method is not only very difficult but also the fastness of washing is poor. The electrophoretic fractionation method is a dyeing method using fractions obtained by electrophoresis. As described in Japanese Patent Application Laid-Open No. 4-366765, the outline of the process is as follows.

-Fix the fraction by fixing the support that completed electrophoresis.

Consisting of three steps of combining silver or silver diaminoions [Ag (NH ₃ ) ₂ ] ⁺ with fractions and then reducing.

However, the electrophoretic fractionation method has a problem that the operation method is complicated and requires a long time for dyeing, and the method of using silver nitrate aqueous solution has very little storage stability because of this reagent (extreme dilute aqueous solution of silver nitrate). There is a problem that is very difficult.

SUMMARY OF THE INVENTION An object of the present invention is to provide a reactive azo dye having strong antimicrobial power by introducing a silver sulfadiazine group, which is an antimicrobial substance, in a reactive azo dye molecule in preparing a reactive azo dye.

The present invention relates to an antimicrobial dye represented by the following general formula (I).

(I)

In the formula, A is hydrogen, methyl group, vinyl sulfone group, methoxy group, n, m is an integer of 1-3.

The present invention will be described in detail with reference to the following Examples.

Example 1.

18.4 parts by weight of cyanuric chloride are dissolved in ice water, and 0.1 part of a dispersant is added thereto, followed by stirring to disperse uniformly.

31.9 parts by weight of 1-amino-8-naphthol-3,6-disulfonic acid was added thereto, followed by slowly adding an aqueous solution of soda ash while maintaining the temperature at 5 ° C. or lower, and adjusting the pH to 2.0 to 7.0. Let's do it.

In a separate reactor, 30.3 parts of 2-naphthylamine-1,5-sulfonic acid are neutrally dissolved in water, and the temperature is maintained at 5 ° C. or lower, and 27.1 parts of hydrochloric acid and 6.9 parts of acetic acid are added thereto for diazotization reaction.

When the first condensation is completed and the soda ash solution is slowly added to the solution in which the diazotization reaction is completed, the coupling is carried out while adjusting the pH to 6 to 8 to obtain a red dye represented by the following structural formula.

35.7 parts by weight of silver sulfadiazine was added to the obtained red dye and heated to 50-60 ° C., followed by secondary condensation at pH 7-8 to obtain a red antibacterial dye represented by the following structural formula.

Salt or potassium chloride was added thereto, followed by salting and filtering and drying to obtain 110 parts by weight of the final product.

Example 2

18.4 parts of cyanuric chloride are dissolved in ice water, and 0.1 part of a dispersant is added and stirred for about 1 hour to be sufficiently dispersed.

After adding 31.9 parts of 1-amino-8-naphthol-3,6-disulfonic acid dissolved in the above-mentioned phase separation solution, the soda ash solution was slowly added while maintaining the temperature below 5 ° C to adjust the pH to 2.0-7.0 as in Example 1. Proceed with the first condensation reaction.

In a separate reactor, 17.3 parts of aniline-2-sulfonic acid was neutrally dissolved in water, and then ice was added to adjust the temperature to 5 ° C or lower.

After adding 27.1 parts of hydrochloric acid, 6.9 parts of acetic acid was added to proceed with the diazotization reaction.

Add the above solution having completed the first condensation reaction to the completed diazotization reaction, and slowly add the soda ash solution to adjust the pH to 6-8 and proceed with coupling.

35.7 parts of silver sulfadiazine was added to the obtained red dye, and the temperature was raised to 50-60 ° C., followed by secondary condensation with a pH of 7-8 to obtain a red antimicrobial dye, followed by salting with salt or potassium chloride. Filtration, drying and pulverization gave 110 parts by weight of red dye as a final product.

Example 3.

18.4 parts of cyanuric chloride are dissolved in ice water, and 0.1 part of a dispersant is added and stirred for about 1 hour to be sufficiently dispersed.

39.1 parts of 1-amino-8-naphthol-3,6-disulfonic acid dissolved in the above dispersion solution was added, and the soda ash solution was slowly added while maintaining the temperature below 5 ° C. to adjust the pH to 2.0 to 7.0 as in Example 1. Proceed with the first condensation reaction.

In a separate reactor, 28.1 parts of aniline-4-sulfatoethylsulfonic acid were neutrally dissolved in water, and then ice was added to adjust the temperature to 5 ° C or lower.

After adding 27.1 parts of hydrochloric acid, 6.9 parts of acetic acid was added to proceed with the diazotization reaction.

Add the above-mentioned solution in which the first condensation reaction is completed to the completed diazo reaction, and slowly add the soda ash solution to adjust the pH to 6 to 8 to proceed with the coupling.

35.7 parts of silver sulfodiazine was added to the obtained red dye, and the temperature was raised to 50-60 ° C., followed by secondary condensation at a pH of 7-8 to obtain a red antimicrobial dye, followed by salting with salt or potassium chloride. Filtration, drying and pulverization gave 97 parts by weight of red dye as a final product.

The dyes obtained in the above examples can be dyed to cotton fabrics by the conventional dyeing method of reactive azo dyes.

Cotton fabrics dyed using the dyes of the present invention have the effect of exhibiting strong antimicrobial properties.

Claims (1)

The red antimicrobial dye represented by following General formula (I). (I) In the formula, A is hydrogen, methyl group, vinyl sulfone group, methoxy group, n, m is an integer of 1-3.