Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2001-04-09
2001-10-30
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
Reexamination Certificate
active
06310187
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a bifunctional red reactive dye and more particularly, to the bifunctional red 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 substantiality 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 in the presence of 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 red 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 red 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 red 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 red reactive dye with high yield and purity and as a result of this, have succeeded in synthesizing a red 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 red 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 red 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 red reactive dye expressed in the formula 1, which comprises the steps of:
(a) condensing both 1-naphthol-8-amino-3,6-disulfonic acid and cyanuric chloride;
(b) diazotizing 2-naphthylamine-1,5-disulfonic acid and then coupling with the condensation reaction mixture of step (a); and
(c) condensing both aminophenyl-&bgr;-acetoxyethylsulfone, expressed by the following formula 2 and the reaction mixture of step (b).
wherein, M is alkaline metal atom.
The process for manufacturing a bifunctional red reactive dye expressed by the formula 1 is explained in more detail as set forth hereunder.
The first step is to condense both 1-naphthol-8-amino-3,6-disulfonic acid and cyanuric chloride. The condensation is performed in the range of pH 1.0-3.0, preferably in the range of pH 1.5-2.5 at 0-5° C. If the reaction solution has less than pH 1, the reaction rate is extremely slow so that cyanuric chloride becomes hydrolyzed and in case of exceeding pH 3, cyanuric chloride becomes readily decomposed. Further, if the temperature is lower than 0° C., no reaction occurs and in case of exceeding 5° C., the yield of the reaction will be lowered due to generation of by-products.
The second step is to diazonate 2-naphthylamine-1,5-disulfonic acid, followed by its coupling with the first reaction mixture, so condensed. Hence, the diazotization is a commonly available method; for example 2-naphthylamine-1,5disulfonic acid is dissolved in water at 0-5° C. and with the addition of concentrated hydrochloric acid and NaNO
2
, the diazotization is carried out. Then the compound, so diazotized, as added to the condensed solution (1) at less than pH 7 and at 0-5° C. so as to avoid the generation of by-products.
The third step is to condense the aminophenyl-&bgr;-acetoxyethylsulfone compound expressed by the formula 2 and the coupling solution (2) at 35-40° C. to produce a bifunctional red reactive dye, expressed by the formula 1, having two groups of monochlorotriazine and acetoxyethylsulfone as a desired compound of this invention. Hence, the condensation is performed at 35-40° C. and when the condensation is completed, a final product is obtained by the salting-out process.
According to this inventions the aminophenyl-&bgr;-acetoxyethylsulfone compound as a raw material, expressed by the formula 2, is prepared by a simple reaction between acetaminophenyl-&bgr;-hydroxyethylsulfone with a mixture of hydrogen chloride and acetic acid.
As described above, the third-step condensation using the conventional aminophenyl-&bgr;-sulfatoethylsulfone requires 2.5-3 hours, while the use of aminophenyl-&bgr;-acetoxyethylsulfone expressed by the formula 2 completes the reaction
Kang Myeong Nyeo
Kim Tae Kyung
Oh Sea Wha
Shin Seung Rim
Song Mi Kyoung
Finnegan Henderson Farabow Garrett & Dunner LLP
Korea Research Institute of Chemical Technology
Powers Fiona T.
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