Bis-azo compounds with 2,3-dichlorobenzoyl group

Details Bis-azo compounds with 2,3-dichlorobenzoyl group Bis-azo compounds with 2,3-dichlorobenzoyl group

1996-08-20

1998-02-10

Higel, Floyd D.

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

Organic compounds

Azo

534849, C09B 31057, C09B 31068, C09B 3310, C09B 35029

Patent

active

057170800

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a novel bis-azo compound.


BACKGROUND ART

It has been known that azo compounds have wide variety of uses in, for instance, dyes, dyestuffs for printing, food colors, liquid crystals and drugs. Among these, bis-azo compounds each having two azo bonds in the molecule are compounds which have generally been known as dyes, in particular, photographic light-sensitive materials used in the silver dye bleach process (see, for instance, U.S. Pat. Nos. 3,754,923 and 3,671,253). Bis-azo compounds used as photographic light-sensitive materials are characterized in that they have, in combination, hydrophilic groups (more specifically, a plurality of, for instance, sulfonate residues) for imparting moderate solubility in water to the molecules and hydrophobic groups and a molecular weight required for rendering the molecules uniformly dispersible in emulsions.
Such compounds should have toxicity as low as possible and should not have undesirable properties such as mutagenicity. However, the studies of the inventors of this invention and recent studies (Mutation Research, 1992, 277, p. 201) make it clear that most of the conventionally known bis-azo compounds show mutagenicity. For this reason, there has been desired for the development of compounds which are much safer and more useful in this regard.


DISCLOSURE OF THE INVENTION

Accordingly, an object of the present invention is to provide a novel bis-azo compound which is free of any undesirable effect such as mutagenicity.
The inventors of this invention have conducted various studies to achieve the foregoing object and as a result, have found out that bis-azo compounds represented by the following general formula (1) or (2) whose acyl group attached to an amino group on an aminonaphthalenesulfonate moiety present in the compounds is modified have low toxicity and are free of such undesirable effects as mutagenicity and thus have completed the present invention. ##STR2##
In Formula (1), R represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted heteroaryl group and X represents a substituted or unsubstituted phenylene group. In Formula (2), R represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted heteroaryl group and A and B may be the same or different and each represents a group selected from the group consisting of hydrogen atom, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms and halogen atoms.
The present invention relates to a bis-azo compound which is characterized in that the N-acyl group present on 8-amino-1-hydroxynaphthalene-3,6-disulfonic acid is 2,3-dichlorobenzoyl group. Bis-azo compounds whose N-acyl group is p-chlorobenzoyl, m-chlorobenzoyl, 2,4-dichlorobenzoyl or 3,4-dichlorobenzoyl group are disclosed in the U.S. Patents listed above, but most of these compounds show mutagenicity.
Contrary to this, the bis-azo compound substituted with a 2,3-dichlorobenzoyl group and represented by the foregoing general formula (1) or (2) has substantially reduced mutagenicity.
If R represents a substituted phenyl group, examples of preferred substituents thereof are halogen atoms, trifluoromethyl group, alkyl groups, alkoxy groups, alkylcarbonyl groups, aryl groups, aryloxy groups, arylcarbonyl groups, cyano group and hydroxyl group, with halogen atoms such as fluorine or chlorine atom, trifluoromethyl group, cyano group, alkyl groups having 1 to 4 carbon atoms or alkoxy groups having 1 to 4 carbon atoms being more preferred as such a substituent. Among these, particularly preferred are halogen atoms, in particular, chlorine atom. Moreover, an unsubstituted phenyl group is likewise preferred as the substituent R.
If R represents a chlorine atom-substituted phenyl group, the preferred number of chlorine atoms present on the phenyl group ranges from 1 to 3 and preferably 1 or 2. If R is a monochloro-substituted phenyl group, the chlorine atom may be on either of o-, m- or p-position, in particular, o-position. If R

REFERENCES:
patent: 3671253 (1972-06-01), Froelich et al.
patent: 3754923 (1973-08-01), Stauner et al.

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