Reactive disazo compound

Details Reactive disazo compound Reactive disazo compound

1983-03-28

1986-04-22

Higel, Floyd D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

G09B 6209, D06P 1382, D06P 340, D06P 366

Patent

active

045843678

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a reactive disazo compound and process for dyeing cellulosic fibers by use of the compound.


BACKGROUND ART

Monohalotriazine dyes are well known to be generally useful for dyeing cellulosic fibers. However, these dyes have a drawback in that a considerable amount of the dye used is not fixed on the fiber because a side reaction occurs between the halotriazine reactive group and water instead of the reaction between the halotriazine reactive group and cellulose, thereby resulting in a low color value and poor build-up property of the dyed fiber. Besides such a loss of dye, the pollution on dyeing waste water containing the unfixed dye causes social problems such as environmental pollution.
It is also known that bis(monohalotriazine) dyes having an enforced affinity for cellulosic fibers are obtained by reacting two moles of a dihalotriazine with one mole of a diamine for the purpose of improving the fixing ratio of dye. This type of dye, however, generally exhibits a reverse relationship between the solubility of dye in water and the affinity of dye for cellulosic fibers, that is to say, the dye having the higher water-solubility tends to exhibit the lower affinity for cellulose fibers.
Consequently, the dye circles have been looking for a dye having a sufficient solubility in water as well as a strong affinity for cellulose fibers and high fixing ratio.


DISCLOSURE OF THE INVENTION

This invention provides a reactive disazo compound of which the free acid form is represented by the formula ##STR2## wherein R.sub.1 represents hydrogen or carboxyl, R.sub.2 and R.sub.3 represents hydrogen or sulfo, either one of the R.sub.2 and R.sub.3 being hydrogen and the other being sulfo, and when R.sub.1 is hydrogen, Y represents 2,5-dicarboxyl-1,4-phenylene, 5-carboxy-1,3-phenylene, or 2-carboxy-1,4-phenylene, and when R.sub.1 is carboxyl, Y represents 1,4-phenylene, 1,3-phenylene or 2-carboxyl-1,4-phenylene. This invention also provides a process for dyeing cellulosic fibers by use of the disazo compound.
As shown in the above formula (1), the number of carboxyl groups, which are water soluble substituents, in a molecule of the compound of this invention is defined to be in the range of 3 to 5 and the positions of the substitution are specified, whereby it becomes possible to obtain a reactive disazo dye satisfying both solubility in water and affinity for cellulose, and by using it, dyed products excellent in color value and build-up property are obtainable.
Furthermore, while the color fastness to chlorine water in home laundry has become important together with other kinds of color fastness such as the fastness to light, wet and perspiration because of residual chlorine in city water and the current wide use of chlorine-containing bleaching agents, it has been found that a carboxyl group ortho-positioned with respect to the azo group of a diazo component, as in the disazo compound of this invention, improves the color fastness to chlorine water more than does a carboxyl group meta- or para-positioned.
For example, a monochlorotriazine dye which is analogous to the reactive disazo dye of this invention and represented by the formula ##STR3## is described in Japanese Patent Kokai (Laid-Open) No. 25728/1973. It should be noted that the cellulosic fibers dyed with this dye exhibit a color fastness to chlorine water (ISO/R, 105/1V) of rating 2-3, while those dyed with the disazo dye of this invention are superior in the fastness, that is, as high as rating 4 to 5.


BEST MODE FOR CARRYING OUT THE INVENTION

The reactive disazo compound of the formula (1) of this invention can be prepared in various ways, for instance, by reacting two moles of cyanuric chloride, two moles of an aminoazo compound represented by the formula ##STR4## [R.sub.1, R.sub.2, and R.sub.3 are as defined in the formula (1)], and one mole of a diamine represented by the formula moles of cyanuric chloride, two moles of an aminonaphthol disulfonic acid represented by the formula ##STR5## [R.sub.2 and

REFERENCES:
patent: 3647778 (1972-03-01), Andrew et al.

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