Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2000-11-20
2001-10-23
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S637000
Reexamination Certificate
active
06307033
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a bifunctional blue reactive dye and more particularly, to the bifunctional blue reactive dye with monochlorotriazine and acetoxyethylsulfone as reactive groups expressed by the following formula 1, which provides excellent combination of properties in that 1) the introduction of aminophenyl-&bgr;-acetoxyethylsulfone group to the dye may minimize the loss of dye, since its low solubility to water lessens the amount of the remaining solution during filtration, 2) an easier salting-out process requires a smaller amount of salt during the process so that the costs for the treatment of waste water may be significantly reduced, and 3) a better dyeing yield with enhanced substantivity and better brightness in color.
wherein, M is alkaline metal atom.
2. Description of the Related Art
The salting-out process is being currently performed as a method of isolating a dye from the reaction mixture after a reactive dye is synthesized. However, in the case of synthesizing a dye with an aminophenyl-&bgr;-sulfatoethylsulfone compound as an intermediate for the manufacture of a vinylsulfone reactive dye, a method of isolating a dye from the reaction mixture is carried out based on a spray drying or in the presence of a large amount of salts owing to the fact that a higher solubility of the dye to water makes it difficult to perform the salting-out process. These methods have brought about the environmental pollution, and the cost for the treatment of waste water containing a very high concentration of residual dye becomes enormous.
In particular, a blue reactive dye containing an aminophenyl-&bgr;-sulfatoethylsulfone compound has a poor substantivity due to its high solubility to water.
Under the current situation where the developed countries such as Europe and U.S.A. has strictly regulated the amount of salt in waste water containing a dye, intensive researches have focused on the manufacture of a low-salt dye and thus, these dyes have been commercialized in a continual manner. There is an increasing trend in favor of the use of a liquid dye in an effort to protect an operator's health and to meet an accurate content of dye in keeping pace with the automatic dyeing process. Thus, the use of a high-concentration dye without any salt should be essential for the manufacture of a stable liquid dye.
Since the solubility of an aminophenyl-&bgr;-acetoxyethylsulfone compound, expressed by the following formula 2, is a relatively lower than that of an aminophenyl-&bgr;-sulfatoethylsulfone, the synthesis of a blue reactive dye using the former as a reacting group has an advantage in that the salting-out process may be easily available in most cases, except for special occasions.
The process of synthesizing a dye in the presence of an aminophenyl-&bgr;-acetoxyethylsulfone compound, expressed by the following formula 2, requires less amount of salt than the conventional dye during the salting-out process which may contribute to reduced salt concentration of waste water. The introduction of aminophenyl-&bgr;-acetoxyethylsulfone group to the dye may minimize the loss of dye, since its low solubility in water lessens the amount of the remaining solution during filtration, thus contributing to further reduction of treatment cost on waste water. Further, a dye, so obtained, has a very high purity and low concentration of salt so that the concentration of salt in waste water may be reduced and the desalting process for manufacturing a liquid dye is quite easy.
The well-known compound expressed by the formula 2 have been disclosed in several literatures. Among related compounds, an manufacturing example for 4-aminophenyl-&bgr;-acetoxyethylsulfone (Japanese Unexamined Publication No. 81-22354, German Patent No. 2,929,107) is shown in the following scheme 1:
Treatment of 98% sulfuric acid to 4-acetaminophenyl-&bgr;-hydroxyethylsulfone gives a compound where two compounds expressed by the formulae (2) and (3) are mixed in the ratio of 70:30. The dye containing the mixture, so synthesized, has been reported to show excellent properties of dye. However, if a dye is synthesized using a mixture obtained from the scheme 1, the presence of 4-aminophenyl-&bgr;-sulfatoethylsulfone is responsible for reduction of substantivity due to its a very high solubility to water.
Nonetheless, any efforts to synthesize a blue reactive dye expressed by the formula 1 has not been made using aminophenyl-&bgr;-acetoxyethylsulfone expressed by the formula 2.
SUMMARY OF THE INVENTION
The inventors have made intensive studies to generate a blue reactive dye with high yield and purity and as a result of this, have succeeded in synthesizing a blue reactive dye using aminophenyl-&bgr;-acetoxyethylsulfone and monochlorotriazine as reactive groups. Thus, this invention has been completed.
Therefore, an object of this invention is to provide a bifunctional blue reactive dye which has an excellent combination of properties such as reduced environmental pollution during the manufacture of a dye, more brightness in color, lower solubility to water, and higher dyeing yield.
DETAILED DESCRIPTION OF THE INVENTION
This invention relates to a bifunctional blue reactive dye expressed by the following formula 1:
wherein, M is alkaline metal atom
This invention is also characterized by a process for preparing a bifunctional blue reactive dye expressed in the formula 1, which comprises the steps of:
(a) diazotizing p-sulfanyl acid and then coupling with neutralized solution of 1-naphthol-8-amino-3,6-disulfonic acid at pH 1-2 and 0-5° C.;
(b) condensing both neutralized solution of m-phenylenediamine-4-sulfonic acid and cyanuric chloride at 0-5° C.;
(c) diazotizing the condensate resulted from (b) and then coupling through addition of the resulting solution to the reacting solution of (a) at a time at 0-5° C.; and
(d) coupling through addition of aminophenyl-&bgr;-acetoxyethylsulfone expressed by the following formula 2 to the resulting solution of (c).
wherein, M is alkaline metal atom.
The process for manufacturing a bifunctional blue reactive dye expressed by the formula I is explained in more detail as set forth hereunder.
The first step is to diazonate p-sulfanyl acid and then couple with neutralized solution of 1-naphthol-8-amino-3,6-disulfonic acid.
The diazotization is performed according to conventional method in such manner that p-sulfanyl acid is dispersed in water at 0-5° C. and then conc. hydrochloric acid and NaNO
2
are added to diazonate. The neutralized solution of 1-naphthol-8-amino-3,6-disulfonic acid is solution prepared in a manner that a base is added to 1-naphthol-8-amino-3,6-disulfonic acid, thereby transforming sulfonic acid group (—SO
3
H) of 1-naphthol-8-amino-3,6-disulfonic acid to sulfonic acid metal salt (—SO
3
M). The bases conventionally used in this reaction are alkaline metal hydroxide and alkaline metal carbonate salt and preferably NaOH, LiOH, Na
2
CO
3
and Li
2
CO
3
are used. The amount of base is determined by equivalent rate to the amount of 1-naphthol-8-amino-3,6-disulfonic acid. Following the diazotization, the diazotized compound is slowly added to the above neutralized solution for the purpose of coupling reaction at pH 1-2 and 0-10° C., preferably 0-5° C. If the pH is lower than 1, the coupling reaction tends to be extremely slow; in the case of exceeding pH 2, the side reaction is generated. In addition, if the reaction temperature is lower than 0° C., the coupling reaction tends to be extremely slow; in the case of exceeding 10° C., the side reaction is occurred.
Seconds step is the condensation of neutralized solution of m-phenylenediamine-4-sulfonic acid with cyanuric chloride. The neutralized solution of m-phenylenediamine-4-sulfonic acid is prepared by the treatment of base to m-phenylenediamine-4-sulfonic acid (—SO
3
H) to give sulfonic metal salt (—SO
3
M). Care of keeping temperature 0-5° C. has to be taken to avoid the (generation of side products.
Third step is the coupling of first reaction mixture and se
Kang Myeong Nyeo
Kim Tae Kyung
Oh Sea Wha
Finnegan Henderson Farabow Garrett & Dunner LLP
Korea Research Institute of Chemical Technology
Powers Fiona T.
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